Seven Self-Coaching Questions Every Leader Should Ask Themselves

Performance vs. Preparation

Even the best actors spend more time rehearsing than performing. The same is true for athletes. For Olympic athletes, they train a whole year for just a few days of all-out performance! In general, no athlete trains 8 hours a day, five days a week. And coaches are always on hand in both cases to help guide top performers through their training and preparation and help them reflect on past performance.

For CEOs, it’s flipped - most of their time is spent “on stage” - in calls with investors, meeting with team members, having one high-stakes conversation after another. And leadership can feel lonely - often, they are doing it with less support than they need. Everyone needs to go backstage to recover and prepare for the next act from time to time, and leaders in particular can significantly benefit from an intentional approach to their development and performance.

As an executive coach to CEOs and their C-suite teams, I help leaders actively and intentionally practice for high-stakes scenarios - tough negotiations, sensitive one-on-ones, or a strategic conversation about pivoting with investors. Together, we reflect on past performance and clarify strategic intentions for the future. Just like in the gym, doing all of this with a supportive coach can make the process more focused, accountable, and effective. 

I often tell my clients that they are their best coach. In fact, they are the head coach. I’m just the assistant coach. And wouldn’t you know it? Most of their self-coaching happens in their heads: after all, our toughest conversations are usually with ourselves. Our inner conversations either help us or hold us back. The following seven questions are starting points for worthwhile conversations to have with yourself. Asking yourself these seven questions can help you clarify and solidify your leadership stance. 

Using these questions can help you find clarity in the chaos, be more purposeful in your leadership, and keep an eye on your strategic intentions…all of which will help you accelerate your growth and the growth of your company and team. Think of every minute spent with these questions as training your most crucial leadership muscles.

The Seven Self-Coaching Questions

Here’s the TL;DR:

Spend 10 minutes journaling with a pen and paper on any of these questions the next time you feel stuck or turned around, and notice what shifts.

1. How am I spending my time?

2. What gives me energy?

3. Who are my heroes and teachers?

4. What will happen if…?

5. What will having that make possible? 

6. What do I really, really want?

7. How have I been complicit in creating what I say I don’t want?

If you like knowing the why behind the how, here’s a deeper dive:

The Power of Self-Coaching Questions

The basic function of an executive coach is to ask questions, to listen, and to help create clarity. A coach is not there to give answers or advice (that’s a mentor or a consultant), but I will often ask as many questions as needed to help you get to the heart of the matter.

You have that same power to ask yourself impactful questions, too.

The questions that I return to again and again are ones that help leaders with the perennial challenges of leadership:

Making high-stakes decisions in high-ambiguity situations
Spending time on high-impact, high joy work
Clarifying goals
Reframing challenges as opportunities
Making Leadership Values crystal clear

Questions are like portals - they open up new doors, new pathways of thinking. “Question” has the word “Quest” in it…and Questions are like that - they can be journeys or adventures. Leadership is a Quest after all - a quest to create something great. 

So it’s a simple equation - ask yourself better questions, get better answers.

How to Use These Questions

First, I highly encourage you to use pen and paper, set a timer, and write your response to one question.

Writing slows down thought, from thousands of words per minute circling in your head to twenty clear, coherent words per minute on paper.

Going for a walk and talking to yourself (150 words per minute) can also help slow down and clarify your thinking - especially if you transcribe the audio and read it later. 

But handwriting is almost like biofeedback. Seeing and hearing your words form on paper as you write can be grounding and meditative, and helps shift your brain functions in similarly positive ways.

Many of my clients make journaling a regular practice because it reliably shifts them from chaos to clarity.

The Why Behind the Seven Self-Coaching Questions

1. How am I spending my time?

It’s the job of a CEO to spend (ideally) 80% of their time on strategic efforts that create impact. As per the Pareto Principle, that time ought to be focused on the 20% of activities that will create an outsized impact. If you’re spending all of your time chasing waterfalls or shiny objects, you might not get as much traction or impact.

Conducting a time audit by looking at data from a few actual weeks is best. 

Look at that data and ask yourself: 

Which of these hours is aligned with the impact I intended? 
Which of these hours were not aligned with creating outsized impact?
How am I using my time to actively care for and support myself?

Looking at the real data can be sobering because there is usually a mismatch between our intentions, plans, and reality. That last question about self-care is key, because there’s no way you can do the job you need to do without making time for sleep or support. Every top athlete spends a shocking amount of time stretching and icing, and resting.

2. What gives me energy?

And it’s worth going a layer deeper - which activities are giving me energy and which are draining my energy? Leaders who learn to eliminate, automate, delegate, or redesign draining tasks free up extraordinary capacity. If we’re spending our time on activities that create joy or energy for us, we can do more in a day.

• How are you spending your time? 

• Right now, set a timer for 3 minutes and list everything you did yesterday. Maybe even open up your calendar if you can’t remember. 

• Circle the top 2 things that gave you energy. 

• What’s one thing you could eliminate, automate, or delegate?

These questions actually take a bit more homework than a 3 or 10-minute journaling sprint. Use this Time & Energy Audit document to get started. Doing this with a coach can add a layer of accountability and clarity, but I always ask my clients to do their own audit first.

3. Who are my heroes and teachers?

Marcus Aurelius starts his 167AD classic Meditations with a list of his teachers and what he learned from them. Making a list of your heroes and teachers can be a powerful exercise. 

(Stop for a moment and write them down now! I bet a few folks have already appeared in your mind.) 

Who do you admire in your field, in your life, in history? These don’t need to be people you’ve met - I’ve never met Socrates, but he’s been one of my heroes and teachers since I was 13.

Now…ask yourself: why? What qualities do they express naturally that you admire? This list is a set of characteristics that you value. And you need to know your values as a leader - those qualities guide you in difficult times.

Don’t forget the essential truth - if you spot it, you got it. You admire these qualities, these values, not because they are out of your reach, but because they are inside of you. Narrow those values down to 3-5, make sure you write them down somewhere visible, and make sure you reflect back on them regularly.  (Many thanks to Ayse Birsel for reminding me of the power of this question.)

4. What will happen if…?

Often, when people have a tough decision, they arrive at one or two options quickly and then circle around the pros and cons until time runs out. 

Instead, try this four-part reframe to expand your vision.

What will happen if…I do X?
What will happen if… I don’t do X?
What won’t happen if… I don’t do X?
What won’t happen if… I do X?

Most leaders making difficult decisions need to weigh the outcomes of action or inaction. And they do this in situations of high ambiguity - there’s no clear, easy answer. Scenario planning is a core leadership skill…and it’s invaluable to consider several opposing scenarios. These questions present four unique ways of looking at your choices and their outcomes.

One CEO I was working with was really tired. After more than a decade and millions of dollars raised, the company hadn’t really found true traction, even with celebrity backing and doing all the right things. He was ready to quit. When he found a potential acqui-hire that would allow him time with his family and time to tinker with other ideas, he still felt stuck - what would his investors think? What about his relationships with his investors? Was he failing as a CEO if he quit before his IPO? These four questions helped him feel fully aligned on his next step - All in.

Try out this question set the next time you’re weighing a key hire or a strategic pivot, or even considering how to spend your time - going to an event, or on a trip.

5. What will having that make possible?

As we weigh a course of action, we’re often fixated on the near-term result - the goal or objective.

It’s good to step back from our goals and ask…and then what? Look at the bigger picture, the longer arc: What will having that goal mean? What’s the goal after the goal? As my wise mother likes to say, “the ceiling becomes the floor.” That is, when we grow and evolve, each achievement resets the baseline. Looking from the vantage point of the future, where our goal is achieved, what is true? Who do we get to be? What is next? 

This question helps align goals with a larger vision, not just short-term milestones.

6. What do I really, really want?

I call this “The Spice Girls Question”. Akin to the activity 9 Whys, I often take time to peel back the layers of the onion on a goal a client has. 

Why do you want what you say you want? And why that? 

Keep asking until you reach the deepest desire.

We’re trying to get to the biggest goal, following the ladder of abstraction to the top. 

I want to learn: Is the goal theirs? Or is it based on an idea of the kind of person someone else wants them to be, borrowed from someone else’s expectations?

What goal is aligned with their essence? Their values? The kind of life they really want to live? 

Real leadership comes from pursuing goals aligned with your essence and values, not external pressure.

7. How have I been complicit in creating what I say I don’t want?

I learned this question from Master Coach Jerry Colonna during our podcast conversation.

When we’re in the thick of a challenge, this question is a powerful one to slow the conversation down and look at what’s in our zone of control. 

In these moments, it’s easy to look outwards. When sales are stalling, when the team is going off the rails, it’s common to look for “one neck to wring” - the source of all the problems.

Making a list of everything that’s getting between us and what we want to create might include external factors - the market, the funding environment, or someone else’s attitudes and prejudices. But that puts the locus of control outside of us. When everything is someone else’s fault, there’s nothing we can do on our own about the situation. We can try to fix others, but there’s a limit to what’s in our direct control.

Step back and ask:

What am I doing to make this happen? Or to keep it happening? 
What is in my power that can make a difference?
How have I been complicit in creating, allowing, or promoting this situation that I say I don’t want?

If you’re not part of the problem, you can’t be part of the solution, as I learned from my podcast conversation with author Adam Kahane. Most problems are systems problems - rooted in complex contexts. A simple solution is usually hard to find. If you have one, guess again. You, dear reader, are part of the system. So, you can find something, however small, that you can do to make a shift in the situation. And sometimes that shift happens inside - not what you do, but how you think or feel about the situation.

A COO I worked with realized they were caught in a “hero” role—constantly rescuing the team from a CEO they saw as problematic. They were caught in a drama triangle.

Wherever there is heroic behavior, there is a villain and a victim. The cycle always repeated: avoidance, then confrontation, then back to rescuing. With some deeper reflection, we uncovered how good it felt to be the hero, and they were able to see their complicity in the pattern. Looking at their complicity helped them step back and have a cool and clear conversation with the CEO about the facts and impacts of the situation before a flare-up.

Take a quick scan for a stuck conflict in your work or life. If you’re pointing a finger in blame at the other person or party, pause and ask: ‘How might I be contributing to this?’ 

Point the finger fully back at yourself, just for a moment. If the situation were 100% your fault, what would that make possible for you? It can feel uncomfortable assuming 100% responsibility. More likely it’s a combination of factors netting out to some ratio or another…but there’s always a gift to be found in assuming 100%. After all, if the situation is 100% your fault, the solution is 100% in your power!

The Power of Telling Someone

Speaking or writing your answers to these questions will absolutely have an impact. Spending time with them can unlock new levels of clarity, purpose, and resilience in your leadership. You could even tell an AI your answers and ask for feedback. But there is something powerful about telling your responses to a real human who cares about you and what you are trying to create and accomplish in the world and in your life. 

There’s a reason leadership can be lonely - it’s hard to find someone you can really tell everything and anything to. You can’t complain about your co-founder to your romantic partner indefinitely. You can’t vent about your CTO to your VC without it having potential impacts. 

Working with a coach can make space for deeper conversations; I don’t accept easy answers and hold my clients accountable to their biggest dreams. What could you accomplish with someone in your corner who was 100% dedicated to your success? When you’re ready to invest in a partner in your growth journey, please reach out here. While I only serve a few clients at a time, I’d love the opportunity to explore if working together would be a good fit.

PS - For the nerds

I did some digging to find actual numbers on training volume for top athletes and found this fun small study from High North, a sports coaching firm.

I particularly enjoyed this chart, which maps training time per month for Olympic athletes. Notice the shift from general conditioning towards more specific sport-related training as the competition approaches…and that total training volume decreases as competition approaches! 

Also, 80 hours PER MONTH is the max amount of training volume. With 480 waking hours a month, that’s spending LESS than 20% of their time a month in training - around 3 hours a day on average.

So here’s a bonus couple of questions for your time audit: 

What would your day look like with 3 hours of solid impact? 

What would you do with the rest of your time?

Why Urgency Kills Growth (And How Commitment Changes Everything)

Are you fighting fires, sitting on calls, or creating the next iteration of your business?

Every morning, noon and night is a flurry of notifications - dings on your phone, pings from people putting something back at the top of your inbox. You can silence the notifications, but that doesn’t hide the reality - there's no lack of things to do - things people need from us, things we planned to work on. There's an infinite tension between the two - what we planned, and what’s popping up.

And that's just the start. If you’re like most leaders I coach, you’re sitting in on a lot of calls. Those calls stack up, crowding your calendar. Keeping you from paying those pings their due. And from giving time to the things you really know you need to get to, dammit.

While some folks think meetings are a waste of time, I believe that they can be time well spent, if the leader hosting the meetings has taken time to master one of the core mindsets and skillsets I coach CEOs and senior leaders on: Facilitative Leadership. Facilitative Leaders know how to manage turn taking, ask powerful questions, and plan meetings better with the 5Es of experience design …and they even host silent meetings where appropriate. Leaders who think their meetings aren’t creating value might even want to have a meeting about meetings, to make sure more of them create value! Collaboration, when done well, can create outsized impact. 

A huge source of impact as a leader? Making sure you have time to spend thinking, reflecting and planning - something I find most leaders struggle to carve out time for. There’s always another email, another meeting. And it’s all due yesterday. 

This constant drumbeat of false urgency saps our energy and keeps leaders in the swirl of today and away from investing their time and energy in forward-looking strategic thinking. In my experience, the most successful leaders are looking past the next quarter, and spending as much time as possible considering what future they want to see three, five and even ten years out - and working to create that future. I always coach my clients to work within the largest vision possible. I’ve got a post-it on my monitor with the word “decades” to remind me of this.

Committing to creating that time and space to reflect, dream and plan can be hard. Setting a standing meeting with yourself is a start, but it can be a struggle to maintain momentum without support. Executive coaching is one way to create an anchor in your calendar for strategic thinking - and that is one reason leaders hire me -  but Executive Leadership Forums are another powerful way to step back from the every day and make time for deep thinking. 

Used in conjunction with coaching, Forums are extremely effective: Coaching is highly personalized and targeted to the needs of the individual leader, while Forums help leaders help each other. Often just seeing that some of their challenges are not unique, but shared, can be extremely helpful.

But still, some folks struggle to make the commitment to Forums. Recently, right before the start of a drop-in forum I host, one founder pulled me aside to tell me:

“We have a call that’s popped up - it’s halfway through the forum. We’re going to miss the second half. I hope that’s okay...”

she said, on behalf of herself and her co-founder.

“Actually, it’s not okay,” I responded. Then explained that in the first half of the forum they would be in small groups to share some of their wins and challenges providing the foundation for the second half - which would be the “payoff” for the work of the first half. I also explained that being part of the forum meant being fully present, all in, to listen and participate 100%. Leaving early wouldn’t just reduce their overall experience - it would diminish the experience of the rest of the group. So, no, they couldn’t come for just half the session. 

I apologized, since they had come all this way to be at the session in person, but that they were welcome to use the adjoining space to prepare for and to take their call.

They were disappointed but considered my pushback. Realizing the value of having this rare time to be in deep conversation with other founders, they said they’d take a moment to consider if they could move that client call and make space for the whole Forum.

In the demanding world of startup leadership and executive management, making time for your own growth, taking time to think and reflect often takes a backseat to the relentless pressures of immediate urgency - the tyranny of the now. 

At these moments it’s helpful to recall former US President Eisenhower saying:

““I have two kinds of problems, the urgent and the important.
The urgent are not important, and the important are never urgent.””

It’s a good reminder that urgency is a signal - a signal that the thing knocking on your door might be less important than you think. If you’re familiar with the Eisenhower Matrix (or it’s new for you), I recommend that you revisit it - mainly because the way it’s traditionally drawn is totally wrong (you can read more about that here). One way to re-draw the Matrix from its traditional visualization is like so:

Most ways of sketching the matrix have the urgent/important as something to do. But I think another way to frame it is as something to doubt - is it *really* that important?! (many thanks to my friend Jon West for pushing back on my previous sketches of a re-imagined Eisenhower Matrix.)

I did consider giving the co-founders a pass. After all, life does happen - folks have had to leave in the middle of a Forum due to a real emergency and the group and the facilitator (me!) were able to adjust and make it work. But I held firm.

The co-founders had a quick huddle, and fired off an email to their client - they would need to reschedule the meeting. With nervous grins they told me that even though they hadn’t heard back from the client yet,  they were all in and would be with the Forum for the full session.

At the break they came up to me and expressed their gratitude that I had said “No.” They related that it was such a relief and a joy to be able to slow down, step back and look at the big picture with other founders. They had already learned a lot from thinking about their challenges, and from hearing other Founders reflect on what was going on for them. They also pointed out that clients reschedule meetings at the last minute all the time and they just have to roll with it. Even at the halfway point, this was a much better use of their focused thinking than going to a call that could happen at any other time.

Urgency is Reactive. Strategy takes slowing down.

My coaching mentor Robert Ellis used a model he called the Futurosity Continuum to help leaders see how effectively they were distributing their time and attention between solving the problems of today vs creating the future they wanted to see.

The y-axis represents all your time, all your energy and all your resources. The x-axis is where you invest your attention. The red curve is a leader who is focused largely on reactive or proactive thinking leaving little time to take advantage of opportunities that pop up and even less time for deep dives, strategic thinking and action. Being proactive does sound better than being reactive, except that we're still solving the problems of the past. Being proactive just means getting ahead of those problems - not creating the next iteration of the business or building the future we want to see. 

The blue curve is the common distribution for scaling and growing founders - mostly chasing opportunities with a little bit of time left over for strategic leadership. 

The green curve is the leader who invests most of their time, energy and resources to strategic thinking, action and emergent listening - paying attention to what the universe is telling them about their strategic intent. The universe in this case can take the form of market signals, community or customer feedback or even the leader’s own inner voice. It takes real intention to slow down and push back against the Tyranny of Urgency and to invest in strategic reflection. 

In this way, urgency kills growth, because the leader who spends all their time putting out fires, or wetting down the areas that may catch fire soon, rarely has the time to think about why there are so many fires all the time?! There’s never time to think about how to build the ideal future, to create unexpected growth opportunities, and to listen carefully to what’s really working.

Firefighting leadership can be effective in the short term, but in the long term rarely delivers dividends without a balanced attention investment curve. Committing to a Leadership Forum is one way of creating reliable accountability for investing in your strategic leadership.

The Compounding returns of Leadership Forums

If you’re unfamiliar, Forums are structured conversational spaces, where people share vulnerably and confidentially with other people. Participants both give and receive support. Companies like Vistage, YPO and EO pioneered the commercialization and democratization of the leadership Forum in the last several decades. But the Forum is based on much older “conversational technology” like T-Groups from the early 1900s, the Quaker religion’s Clearness Committee from the 1800s or even the deliberative listening styles of the Free Masons that reaches back to the 1500s and even earlier. The word “Forum” itself is taken from the Greek word for the space at the center of town dedicated to the real conversations of the day. I remember visiting Athens and standing in the Forum where Socrates stood in 390BC, having some of the most important conversations in the history of western civilization - it was spine tingling! 

Sitting in a community circle and having a real talk is a tradition older than our ability to reckon.

The ROI of a long-term commitment to a leadership forum can’t be overstated. It’s like putting money in an IRA - the returns compound over time. My Forum has been meeting for nearly 5 years. One member of that Forum has been in another forum for almost 15 years! Treating the commitment as inviolable almost turns it into a sacred space, a real necessity for all leaders.

The transformative power of Forums is in two key aspects - in the reciprocal exchange (to listen and share deeply) and in the commitment to come, again and again. Each month is an opportunity to check back in - did your Forum-mate do anything about the challenge they shared about last time? The accountability and shared context is impactful.

In New York City, I host a “drop in” Forum for Founders monthly, and there’s a lot of value to be had in coming on any given month and seeing some old friends and making new ones. It mixes things up. But each time we meet, I need to re-create the container - making the rules about confidentiality clear, getting folks up to speed on the structure and format. Time given to that ramp-up is used to dive deeper in a longer-term committed Forum.

I’ve been part of and led two key types of Forums - Facilitated Forums and Peer-Led Forums. Some companies, like Vistage, will fully host and lead the Forum for you, so you can lean in and focus 100% on being fully present. On the other hand, peer-led Forums rotate leadership and facilitation responsibilities - notably, YPO does this. The peer-led forums give members the opportunity to practice the facilitative leadership skills that are essential to modern collaborative teams. One type of forum isn’t better than the other…both will deliver value over time, and just like investing, the best time to start is now.

At the end of the Forum, I checked back in with the co-founders. How did they feel about their choice? Had the client been okay with pushing back the meeting?

They shared that the client was actually *glad* to push the meeting to next week - my in-person forum meets on a Friday, and who isn’t glad to cancel a Friday meeting?! And the co-Founders shared that they are very rarely in the same place at the same time. I put them in separate break-out groups, and each founder had gotten a uniquely helpful perspective on some core challenges they’d been facing. The ROI of investing in longer-term thinking vs being pulled into the day-to-day was immediate.

What to do next:

1. Commit to yourself. Take some time to do a Time and Energy audit to give you a clear picture of what your current calendar is like. Link here to get you started. 

2. If you’re in NYC, consider applying to my monthly drop in Forum.

3. Join a Forum or start your own. Making that monthly commitment to other people can help you prioritize strategic thinking over replying to those pings.

4. If you think one-on-one support to focus on your most important challenges can help accelerate your growth, you may be ready for coaching. Learn more here.

How to Maximize Your Most Scarce Resources as a Business Leader: Time, Energy and Talent

What are today’s most scarce resources?

While money can be found, borrowed, printed or even invented, we all know that no amount of money can buy a 25th hour in the day. Time is limited, tomorrow is not guaranteed. And no amount of money can make someone really care. No amount of money can motivate someone to give every ounce of their energy and talent. You can’t buy real enthusiasm! The only way to get the best work from someone is to inspire them and then get out of their way.

For most companies, the most scarce resources are the time, energy and talent of their people, and the insights, ideas and wisdom those people generate. As Michael Mankins and Eric Garton write in Time, Talent, Energy:

““Ideas don’t just materialize; they are the product of individuals and teams who have the time to work productively, who have the skills they need to make a difference, and who bring creativity and enthusiasm to their jobs…what separates the best from the rest is leaders’ ability to manage human capital in the broadest sense.””

It can feel like we never have enough time. Our energy doesn’t feel unlimited. And world-class talent is hard to find and afford. But without these three elements, time, energy and talent, it’s nearly impossible for  innovation-and-profit-driving ideas to be uncovered, refined, and brought to life.

Step Zero: Start with yourself

As a leader of people, it's your job to unlock and maximize the energy and talent of your team by helping them use their time well. While it’s tempting to start with your team, I recommend starting with yourself: be the change! Start by using your own time, energy and talent well. Then, coach your team to do it, too. Leaders can do this by:

• Modeling the intentional use of time - by focusing on the important over the urgent (bullet point #4 below)

• Modeling the intentional use of talent- by focusing ONLY on things that are great uses of your unique skills, your Zone of Genius (bullet point #3 below)

Once you start intentionally focusing your time and talent, and coaching and encouraging your team to do the same, the creative energy in your organization will start to be unleashed on an individual basis. But to scale your team’s impact, you need to have the facilitation skills to ensure that the meetings you host don’t waste anyone’s time or suck anyone’s energy. This is the magic key to unleashing the time, energy and talent of your team: creating moments of impact with your team by bringing folks together to solve problems in effective ways that wouldn’t have happened without that meeting. Without the key ingredient of Facilitative Leadership your meetings will waste your team's resources, rather than unleashing them.

Facilitative Leadership is rare, but leaders who master it can intentionally create spaces and places where people are empowered to do the best work of their lives. It’s a topic too big for this essay. But you can read more about Facilitative Leadership skills like mastering turn taking, asking powerful questions, the 5Es of meeting experience design and even leading silent meetings at the links embedded here. You might even need to lead a meeting about meetings with your team or work to make your meetings less “leaky". 

There’s another way to describe the outcome of this approach, the real goal: creating a platform for human flourishing. (Those words are from Ashley Goodall, former Cisco Exec and currently a leadership expert and author of the Bestselling books, Nine Lies about Work and The Problem with Change, AND a wonderful guest on my podcast.)

1. Ask for their best and create a platform for human flourishing

I love this phrase, “a platform for human flourishing”.

It’s a reminder that the real job of a company is not *just* to maximize shareholder value, which it must do - that’s table stakes! A company exists to serve a customer, to make their lives better. But that’s just one side of the platform. On the other side are all the people who come together to make that happen. Employees are customers of another sort, and creating a place to work that’s a drag for employees while creating value for your external customers is not just a missed opportunity, it's unsustainable.

Recently, a coaching client of mine complained about the quality of work coming from their team. They wanted to communicate clearly what the “minimum standard” looked like—and make it crystal clear that nothing should get out the door without meeting that standard.

I pushed back with a question:

“Are you trying to create a minimum standard company? A minimum standard culture? Or do you want a company where people know they have an opportunity to do the best work of their lives?”

“The best work of their lives?!” my client asked.

I asked them—and I’ll ask you to consider this as well—when were you first on a team where everything hummed? A place where you look back and think, “Wow, we did some great stuff”? A place where you were proud of the output, even though it was a lot of work? And that you still feel pride about?

Now, think about the team you lead today. What are you inviting them to do? Just “good” work? Or work that they will continue to be proud of in 10 years? As a leader, you can create that opportunity. Setting the expectation that people can do “the best work of their lives” under your leadership is a bar that people can be excited to meet. And when your talented team members are excited about their work, you’ll get the best energy and application of talent from the time they spend.

2. Architect moments of efficient collaboration through Facilitative Leadership.

Remember the quote from Mankins and Garton that we started with:

““Ideas don’t just materialize; they are the product of individuals and teams who have the time to work productively””

That work never happens 100% alone - we have to come together to talk, to coordinate, to collaborate. And… We’ve all been in meetings that intend to help us do just that, but instead waste people’s time by not delivering on real value. It’s exhausting for everyone. In fact, it’s a real drag.

The more intentional you can be about the time your team spends together, the higher the chances are that you will get the most out of that time. Intentionally designing the time people spend together is the heart of Facilitative Leadership. In order to unleash the time and talent of your organization, you need to be able to facilitate these moments of impact. Otherwise, you create what Mankins and Garton call "Organizational Drag”: friction that drains people’s energy and wastes people’s time. 

Many organizations, even at small sizes, create organizational drag. For example, one founder I worked with had a senior team of only five people, plus another 15 or so in the rest of the org. They were very early in their product-market fit iteration, but challenges were already emerging from the way they ran leadership team meetings. When I hosted 360-degree review interviews with the leadership team, I heard again and again that they felt several of their meetings duplicated or overlapped efforts and that they didn’t feel that their time was being well spent. Many of the team members also commented in the interviews that the CEO took up the most airtime in the meetings. While it was critical to the team that the CEO share what they felt were the biggest challenges facing the young company, the C-suite wanted the opportunity to contribute more, not just listen to the CEO.

Facilitative leadership creates opportunities to unleash the energy and talent of your team, and this is a mindset and skillset I had to start coaching this leader on - how to make sure they were making sure the entire leadership team felt like they were contributing their time, energy and talent in every meeting.

Every meeting is a potential moment of impact. In our podcast conversation, Lisa Kay Solomon and Chris Ertel, co-authors of Moments of Impact, made this idea clear: “At these critical moments, everyone will be looking at you—not for all the answers, but to help them unearth the answers together.”

Solomon pointed out that what she and I call “Conversation Design” is one of the most impactful leadership skills—and one of the hardest to teach. The ability to architect efficient, collaborative conversations is an impact-multiplier skill, because doing so enables people to leave meetings with a sense of momentum rather than feeling like it could have been an email. Refreshing your facilitative skills is one way to make sure you're creating opportunities for your team’s best work to be unleashed and connecting their diverse talents to drive creative thinking.

In Solomon’s definition, the basics of facilitation are simply about the non-negotiable, essential mechanics of leading a conversation, like starting and ending on time and being able to run different modalities of participation effectively. Conversation Design is about the questions leaders need to ask themselves in shaping strategic conversations to make sure they don’t run efficient but ineffective gatherings.

Questions leaders can ask themselves before hosting a meeting
(after asking the all-important question, is this meeting necessary?):

• "What do I want this conversation to advance?"

• "What do I want people to know, feel and do long after this conversation?"

• "What is the culture I want to build by the choices that I make in this session?" 

• How will this gathering unlock the time, energy and talent of my team?!

3. Optimize time and talent. More Energy follows.

Physics teaches us that Energy can’t be created or destroyed - we can only use one type of energy to create another. Like how our bodies change the chemical energy in the food we eat into mechanical energy when we move things around. Or when a roller coaster’s potential energy at the top of a hill turns into fun kinetic energy as we roll down the hill. In other words, you can’t “make energy”. But when you let your team know that you’re all about creating a platform for their flourishing by inviting the best work of their lives, and intentionally creating moments of collaboration that reduce drag, you can start to get the energy in your team moving.

But what are they going to apply their best energy to? What’s the best use of their time and talent? Once you start focusing on the ideal use of your time and talent, and then your team’s, you start to create a powerful feedback loop of energy creation.

The intersection of time and talent: The Zone of Genius

One of my favorite diagrams to draw for my clients is the Zone of Genius map adapted from Gay Hendricks’s book The Big Leap: Conquer Your Hidden Fear and Take Life to the Next Level. The Zone of Genius map plots the best uses of your time on one axis against the best uses of your talent on the other, to create four zones: the zone of incompetence, the zone of competence, the zone of excellence, and the zone of genius.

The zone of incompetence encompasses tasks that are the worst use of your time and talent—others can do these things better than you can. The zone of competence are those tasks that are a good use of your talent but not a good use of your time— because others can do these things just as well as you can. The zone of excellence includes those tasks that maybe aren’t the best use of your talent but they are a good use of your time - these tasks create value and you're good at them. But the highest value you can deliver is in the top-tier quadrant, the Zone of Genius. These tasks are the best and highest use of both your time and your talent, leveraging your unique genius.

Before using the Zone of Genius map as a tool to figure out where leaders should spend their time, it’s important to first ask: What is the job of a CEO or CXO? Some use the metaphors of a firefighter, or a visionary, or a cheerleader. I worked with a CEO who decided to make sure he spent one day a week being a cheerleader, going around the company telling people what they were doing well. The impact was awesome: his team felt seen for their hard work and efforts, and as a result, morale, engagement and retention in the company went up. 

Some leadership theorists advocate that, especially for early-stage founders, keeping wide swaths of time open is ideal - so that these leaders can step in to be the firefighter, generating solutions to emergent problems that have no standard procedure or dedicated employee to resolve them. Others suggest that the real job of a CEO is creating the next iteration of the org by getting clear on the biggest vision possible, and communicating it relentlessly.

I say, the CEO should do only those things that fall into their Zone of Genius, —work that doesn’t feel like work, work that gets you in a flow state, work that you can have an outsized impact on, work that creates energy.

For anything that doesn’t fall into this zone, CEOs should hire and delegate to people for whom the tasks do fall into their Zone of Genius (or make a specific plan for doing so when funds are available). Developing a platform for human flourishing means finding talent that loves to solve the challenges that you can’t or don’t get juice from solving. And by “juice” I mean the inner satisfaction that comes from working in your Zone of Genius in order to make a difference on a problem you care about.

I’ve found that when my clients start focusing on their zone of genius they start to notice and appreciate the zone of genius of their team and are able to help their team members redirect their focus towards activities in this zone. 

ZOG-obsessed leaders can proactively build a culture of genius—a place where every team member from the CEO on down is expected to understand and operate in their ZOG as much as possible. When people are working in their Zone of Genius, their time is always well spent, and their talent is always well used.

If you want to start uncovering your ZOG, start by doing a time and energy audit. You can find some instructions and guidelines for doing that here. That audit can help you start to zoom in on where your ZOG might be.

4. Focus on the important and not the urgent

Identifying your ZOG is just the start; actually executing wise time management, learning to delegate, and practicing saying no are an iterative learning process. The truth about time management is that it is, in and of itself, work that we all must learn to do competently. We all have a million things coming at us at once. And our brains are uniquely suited to focus on NOW. It’s a fundamental cognitive bias that has helped us to survive for millions of years. For millennia, if there was food in front of you, you ate it, while you could! Delayed gratification is not a gut instinct for most of us. Learning to focus on what is really important, rather than merely urgent, is why I nearly always introduce my coaching clients to the Eisenhower Matrix, a classic time management framework, because it takes the idea of a “to do” list and makes it much, much more impactful.

Former US President Eisenhower is quoted as saying, “I have two kinds of problems, the urgent and the important. The urgent are not important, and the important are never urgent.” The Eisenhower Matrix plots these binaries (the urgent and the important) on two axes, resulting in four quadrants.

The “Classic” Eisenhower Matrix:

Usually, people rank the priority of the quadrants thusly:

• Quadrant 1: DO IT. These tasks are both urgent and important. And you just do them, asap.

• Quadrant 2: Schedule it! These tasks are really important but not breathing down your neck. So, put them on your calendar, and do them in a timely manner.

• Quadrant 3: Delegate. If the tasks are not important but persistently urgent, or not in your ZOG, get someone else to put it on their DO quadrant going forward.

• Quadrant 4: Delete it. As I learned from Randy Paush’s EPIC time management lecture, it’s amazing how much better your life can be if you just patiently and consistently ignore things that are neither urgent nor important. (watch that video. Listening to a person that is rapidly dying of cancer talk about time management is humbling, to say the least. And the fact that the talk is nearly the same as one he delivered using OVERHEARD PROJECTION SLIDES nearly a decade earlier speaks volumes about dying the way you lived.)

Again, because of our millennia-old lizard brains, it’s fundamentally hard to pull away from the DO quadrant, and the tyranny and the urgency of NOW, to focus on the “Schedule It” orange quadrant. These “Not urgent and important” things are exactly those things that will create an outsized impact tomorrow. Focusing further out than today is how you create the most impact. It’s also how you start to tame the tyranny of the urgent and how you inspire your team to get the best from themselves.

It is hard to think clearly, strategically, to focus on our zone of genius, when we are always pulled into the swirl of the DO quadrant. Unfortunately, the way the Eisenhower Matrix is drawn traditionally is deceptive and wrong…each area is not equal, or rather, SHOULD not be equal, in terms of time spent daily, nor is the DO quadrant the one that should be in green signifying “go do it”!

“The urgent are not important, and the important are never urgent”

Remember the quote the Eisenhower matrix is based on. The Important/Urgent quadrant, according to Eisenhower, doesn’t actually EXIST. And it should not be green-quadrant-priority #1…at least not according to the person the idea is attributed to!

I coach my clients and their teams that their IDEAL Eisenhower Matrix should have very, very little seemingly Important/Urgent work and instead focus mostly on non-urgent but important work, because that is how you stay focused on strategy—on creating the future you want, not treading water today. Maybe the ideal Eisenhower matrix actually looks like this: Almost ALL important, non-urgent work (in green, upper right), and some thoughtful delegation work (non-critical and urgent, in blue, lower left). Since the important is never urgent, and it’s a trap, let’s make it a dark, tiny square in the upper left.

Time, talent, and energy unlocked

Maximizing time, energy, and talent is the cornerstone of a flourishing company. Leaders have to start with themselves - by knowing what their Zone of Genius is before coaching their team members to help them do the same.

Unlocking people’s TIME means everyone plays a vital role in driving success by working on the right problem for the organization, but it also means working on the non-urgent problems that help the team stay ahead of the curve - working on tomorrow’s challenges before they become urgent headaches.

Unleashing people’s TALENT happens when leaders hire and delegate effectively, empowering team members to operate in their own Zones of Genius and contribute at their highest potential. 

Leaders can unlock the ENERGY of the team through moments of intentional collaboration, facilitative leadership, and the elimination of organizational drag. When the time, talent and energy of your team are aligned in well-facilitated moments of impact, unlocking innovation through sustained creativity is the natural result: a thriving, high-performing organization, where people feel inspired, valued, and supported to do the best work of their lives.

Goals Won’t Lead You to Greatness

One of my favorite ideas is expressed in an oft-mis-quoted F. Scott Fitzgerald essay titled, “The Crack-Up,” published in Esquire in the 1930s:

“The test of a first-rate intelligence is the ability to hold two opposed ideas in the mind at the same time, and still retain the ability to function.”

Usually, people stop the quote after this first sentence, but the rest of the passage gives useful context:

“One should, for example, be able to see that things are hopeless and yet be determined to make them otherwise. This philosophy fitted on to my early adult life, when I saw the improbable, the implausible, often the ‘impossible,’ come true.”

I’m holding two opposed ideas in tension right now:

1. Having clear goals and making bold choices create powerful results.

2. Clear goals inhibit the achievement of greatness.

As an executive coach, my clients invest significant time, energy and resources into creating what they want in their lives, and into working with me to help them get to their next level of greatness. They have big, transformational goals: They want to transform industries. They want to create their next big dream after a successful exit. They want to lead their companies 100% authentically and powerfully as their companies grow at an improbable rate. To achieve these sometimes nigh-impossible goals, they need to make bold choices.

Often, potential clients say they want to work with a coach, like me, to ensure they remain accountable and diligent in reaching their goals and creating the life that they choose. 

The goal math is simple:

Big Goals + Accountability = Success!

But the reality is more complex. 

Sometimes these transformational changes take more than goals and accountability, clarity and dedication. Transformational changes in our life often entail transformational shifts in how we think, what we value and how we see ourselves.

And sometimes, real transformational change requires us to give up our goals and objectives entirely.

(Insert record needle scratch here.)

Wait…what?!

You read that correctly. I hear your skepticism and simply ask that you join me on this thought experiment for a few minutes and see if we can pass the Fitzgerald test and think differently without breaking our brains. At the end, you may be willing to free yourself of the need for specific goals for everything and leave open the possibility that curiosity, wandering and dreaming might be the key to a life worth living, and yes, greatness.

Truth One: We need bold choices to get anywhere

I was reminded recently of this amazing moment in Viola Davis’s interview on Hot Ones, a super fun web series where guests eat progressively spicier hot wings while answering questions from host Sean Evans. Evans had asked Davis (who is one of only three actors in history to earn both the Triple Crown of Acting and an EGOT!) about her Oscar-nominated performance opposite Meryl Streep in Doubt, in which her character appears for only about 10 minutes but is, as film critic Roger Ebert wrote, “the emotional heart and soul of the film.” Specifically, Evans asked about Davis’s perspective on the opportunity an actor has when their performance is limited to a single, and in this case pivotal, scene.

Davis’s response? Prepare everything you need to, and then take a risk.

“Whatever you're thinking in your mind, make a bold choice.

“Even if you think you're running in the wrong direction, make a choice so bold and so out there, and maybe it'll stick. Or maybe you'll fail—which I've done a lot—but maybe it'll stick.”

As Davis points out, when we’re given a rare opportunity, or a chance to go after a dream, it’s worth it to make a bolder choice and turn the wheel of chance rather than playing small. Those bold choices can transform our trajectories in big ways. Without taking these bold choices, we risk relegating ourselves to smaller, meeker paths, scant achievements, and paltry dreams. Or worse: we drift—we just go with the flow of life and never really get anywhere. 

Or at least, that’s how the “bold choices” narrative goes. The implication is that without clear objectives and bold choices, we can’t really get anywhere at all. Inverting this truth, we can get another truth: Getting anywhere is better than drifting.

That idea is from Richard Hamming in The Art of Doing Science and Engineering:

“The accuracy of the vision matters less than you might suppose, getting anywhere is better than drifting, there are potentially many paths to greatness for you, and just which path you go on, so long as it takes you to greatness, is none of my business.”

So far, Davis and Hamming are lining up in the bold goals and choices camp! Making a big choice is better than making a small choice. Having a big goal is better than an itty bitty goal - because you might hit it big. Aim for the stars and you’ll reach the moon. Just reach for the moon…and that’s as far as you’ll get.

But Hamming’s ideas seem to open up a crack in the simplicity of goal math - maybe goals are less important than we think? He is proposing that vision and goals matter less than making a choice to keep moving forward, to never drift. And to stay open to the many paths before us. Davis says “the bolder the better" since maybe it’ll stick…Hamming seems to imply that boldness is only important in that boldness is a way of moving forward.

Truth Two: Objectives help us move in the right direction

Books like Radical Focus by Christina Wodtke popularized and clarified the “Management by Objectives” approach used at Google and other vanguard tech companies, underpinned by the Objectives and Key Results (OKRs) framework. In her book, Wodtke tells the novelized story of a young company that spreads itself too thin, spending too much time and energy focused on non-strategic initiatives instead of those that could create more profound business impact. The characters in Wodtke’s story make a lot of Davis-like bold choices but ones that are always running in the wrong direction, or just too many directions at once. Eventually, Wodtke argues, companies operating in this way run out of time, energy and resources and cease to be.

Instead, Wodtke suggests that teams align on what their objective is (a.k.a. what they define as greatness) and what it would look like when they achieve it—in other words, how could they measure that greatness? These measurements are the “key results” that help them to stay on track and even shift tracks, when necessary, to stay on course for greatness.

Hamming’s view aligns with the OKR approach: There are many paths to greatness, but we can’t try them all out at once, so let’s just pick one to start and see how we go for the next three or four months! We can change course if we need to after seeing the data. 

These regular periods of setting OKRs and checking in on them are meant to keep organizations and teams on a path to greatness.

Defining what greatness is, for ourselves in our lives, and for our businesses, is no small task. This is something that I regularly help my coaching clients with, what I call “The Spice Girls Question”: What do you really really want? It’s essential to question our goals and ask why we want them. Is it because of cultural programming or parental wounds? Is what we want to create really, really aligned with our core values, beliefs and identity? After all, following a great goal for the wrong reasons is not likely to satisfy us once we get there.

It’s worth questioning the motivations behind our objectives and goals regularly, to make sure they are really really our own and will move us in the right direction.

Truth Three: Objectives rarely lead to breakthroughs

I apologize, since we’re now going to try to hold a few more than two ideas in our mind simultaneously

I’ve been reading Kenneth O. Stanley and Joel Lehman’s 2015 book, Why Greatness Cannot Be Planned, which picks apart what they call “The Myth of the Objective”. Reading this book, I found it surprising to hear the authors point out the deep flaws and contradictions they see in the notion of objectives, since they both have deep technology backgrounds, and the OKR framework is often deeply embedded in many modern tech companies and with folks of a technological bent. 

Maybe there is no Fitzgeraldean paradox here. Stanley and Lehman suggest that objectives are useful for near-term, modest and conventional goals. And indeed, OKRs are often used for that specific purpose - near term goals, looking 3-4 months out.

But objectives fall apart (in their view) when we want to create something truly BOLD: shockingly, world-changingly, innovative.

Why? History is one guide.

The authors point out that in most significant technological advances in history, the “stepping stones” towards the breakthrough were usually unexpected. These breakthroughs didn’t come about by keeping a laser focus on one initial objective; finding these outcomes came from winding down unforeseen paths, sometimes completely unrelated to the initial objectives. Even the scientists who invented the laser were working on solving another problem entirely!

Stanley and Lehman give the example of vacuum tubes and computers:

The first computer, called ENIAC, was built in 1945 as a result of a two-year government contract. At 8 feet tall and over 100 feet long, it was 1,000 times faster than existing electro-mechanical computing machines at the time. Vacuum tubes made the innovation of this first computer possible. However, vacuum tubes weren’t created as part of the process of building a computer. They’d been invented 50 years earlier by people who did not have the invention of computers in mind at all; they were solving a set of very different problems.

Stanley and Lehman posit that, even with Viola Davis levels of boldness, if a scientist in 1943 had chosen to build a computer as fast as ENIAC the size of a coin—a capability we achieved decades ago – they wouldn’t have been able to. The stepping stones to get there weren’t at all obvious and were all arrived at serendipitously. They would have boldly and diligently sweated out the two years of the contract fruitlessly—which leads to the author’s broader point about objectives:

“Objectives are well and good when they are sufficiently modest, but things get a lot more complicated when they’re more ambitious. In fact, objectives actually become obstacles towards more exciting achievements, like those involving discovery, creativity, invention, or innovation—or even achieving true happiness.

“In other words (and here is the paradox), the greatest achievements become less likely when they are made objectives. Not only that, but this paradox leads to a very strange conclusion—if the paradox is really true then the best way to achieve greatness, the truest path to ‘blue sky’ discovery or to fulfill boundless ambition, is to have no objective at all.”

As the authors point out, the structure of human progress is complex: the only possible pathways to many discoveries are counterintuitive and cannot be planned ahead.

Remember the Adjacent Possible!

Transformation and innovation following these possible pathways are sometimes called “the adjacent possible,” an idea coined by Steven Johnson, who summed it up in a 2010 Wall Street Journal essay, “The Genius of the Tinkerer,” this way:

“The adjacent possible is a kind of shadow future, hovering on the edges of the present state of things, a map of all the ways in which the present can reinvent itself…

"The strange and beautiful truth about the adjacent possible is that its boundaries grow as you explore them. Each new combination opens up the possibility of other new combinations.”

If we become laser-focused on our goals, as many folks in the hustle-culture-sphere assert, we ignore all the potentially interesting possibilities that hover outside of our tunnel vision. And it is these adjacent possibilities that can unlock amazing potential.

There are so many stories of companies that pivoted into something much more interesting and much more successful than their original idea, often leveraging some forgotten side project. Just google the stories of Odeo, a podcast tool that turned into Twitter, or the tale of Flickr rising from the ashes an online RPG called Game Neverending…or Wrigley Gum, which started as a giveaway for a home goods company. The gum was more popular than the actual product and once Wrigley focused on that, he eventually unlocked a billion-dollar industry. If any of the folks behind these pivots had persisted in their objectives relentlessly, they might have missed the real opportunity.

It turns out that being laser focused on our goals can cause us to lose sight of some alternative, magical futures hovering just outside our field of vision, in the adjacent possible. And worse: goals can seriously backfire. Stanley and Lehman’s big take home is that greatness is often the result of serendipity - looking for a needle in a haystack and finding something better than you can imagine, something you weren’t looking for at all - like a magnet to find a million needles, or a pot of gold.

Truth Four: Goals can backfire

A goal or objective is the end towards which all our efforts are aimed. Stanley and Lehman point out that with an OKR framework, we’re always working towards better numbers for our key results. It’s like the childhood game of “Hot and Cold”—we all figured out how to move closer and closer to our goal as we got “hotter, colder, hotter!!”

Yet, goals and objectives are only about what we can measure. And much of life, including its ultimate purpose, can’t be well-measured. Viktor Frankl wrote about this in Man’s Search for Meaning:

“Don’t aim at success — the more you aim at it and make it a target, the more you are going to miss it. For success, like happiness, cannot be pursued; it must ensue, and it only does so as the unintended side-effect of one’s dedication to a cause greater than oneself or as the by-product of one’s surrender to a person other than oneself. Happiness must happen, and the same holds for success: you have to let it happen by not caring about it…success will follow you precisely because you had forgotten to think of it.” (emphasis mine)

Frankl lived through the holocaust in Nazi Germany. His philosophy of meaning would be striking in anyone, and is only more striking because he was able to persist in finding meaning through his horrific experiences.

So, what do we ultimately want? In other words, what’s our real goal in life? For many of us, it’s likely things that have no limitations and can’t be measured—“to live well” or what the Greeks call eudaimonia, flourishing. And yet, we often sacrifice flourishing for a smaller or more temporary goal, due to our relentless pursuit of a single-minded goal.

Emmanuel Acho knows this all too well. Acho is a former NFL player and current TV sports analyst and author. In 2023, he delivered a TED Talk entitled “Why You Should Stop Setting Goals (Yes, Really)” in which he asserts that “the surest way to fail in life is to set a goal.”

He tells his story of wanting to get into the NFL as a first, second or third round pick, but his Big Hairy Audacious Goal was *actually* to be a millionaire by 21; getting into the NFL was, he resolved, his surest path. So, he trained relentlessly in his senior year of college, bulking up and getting stronger and stronger. Two days before the NFL Combine (the “job interview” for the NFL, where potential recruits literally get put through their paces), Acho realized he had bulked up too much and needed to drop 10 pounds, which he did through ruthless fasting and sweating out water weight. 

Dehydrated and stressed, he got on the starting line on the day of the Combine to do a 40-yard dash as all 32 NFL team owners looked on. In Acho’s words:

“The 40-yard dash is one of the testing metrics you use at the NFL Combine with millions of dollars on the line. The faster you run, the higher you get drafted. 

“I take my mark. 

“I proceed to run. I hear pop, pop, pop. I keep running. I think my heels are clicking. Pop, pop. I clutch my quad. I fall to the ground. 

“It was my quad being torn off the bone. I rip my quad off the bone. I'm falling to the ground in agony in front of these 32 billionaires. I didn't get drafted in the first three rounds of the NFL draft. I made a decision that day, in that moment, to stop setting goals.”

It’s a horrifying story. Acho was so focused on his near-term goals (getting into the NFL) that he caused harm to himself and to his larger, longer-term goals.

Acho goes on to point out other ways our goals can harm us. If we fall short of a goal—for example, to read a book a month or grow your business 20%—we’re often very hard on ourselves. While we may have learned a lot from the seven, eight or even nine books we read in the year, we punish ourselves for not reading the additional three, four or five. While we may have restructured our business thoughtfully to be well-positioned to achieve rapid growth in the future, we easily dismiss or feel disappointed by the modest growth we wrangled so far.

Falling short of our goals often puts our focus on what’s missing, not what we’ve achieved.

Instead, Acho suggests picking goals that are more open-ended, like the Metallica guitarist Kirk Hammett whose goal is simply “to play my guitar a little better every day.”Such a goal doesn’t have much of a downside and has exponential upside. A little better every day compounds quickly.

Use Four layers of goals

I recently watched a video from Cassie Kozyrkov, who served as Google’s first Chief Decision Scientist, advising leadership on decision process design, AI strategy, and building data-driven organizations. She suggests setting a structured pattern of goals in three layers:

1. Outcome Goal: This is your North Star—something you really want to achieve that keeps you moving forward. This goal is not in your control (Acho can’t hire himself to the NFL, for example.)

2. Performance Goal: A way to measure success (that is ALSO not in your full control, but you can track how much stronger or faster you’re getting. For Acho, performance in the Combine was key.)

3. Process Goal: Something that you CAN put into your control that will help you achieve Goals 1 and 2. (For example, following a good training plan, which Acho did.)

Kozyrkrov points out that we ought to NEVER let a Process Goal take precedence over an Outcome Goal. Stubbornly running too much too fast, or running on an injured knee, according to the process plan, isn’t going to help your outcome goal. Trust the process, sure, but make sure you verify that the process isn’t moving you in the wrong direction from your North Star from time to time. Acho attempted to sacrifice short-term physical wellbeing for long-term financial wellbeing, and his gamble backfired. 

In fact, we might need to add a FOURTH goal layer: anti-goals. Anti-goals would clearly describe the signs to watch out for that indicate you’re moving away from your ultimate Outcome Goal. In Acho’s case, he certainly did not want to tear his quads off the bone and spend months in rehab. It might have helped to have set an anti-goal around injury or markers of worsening physical health.

Truth Five: Goals can miss the bigger picture

Acho learned a hard lesson: goals can cost us, and sometimes more than we realize. We set goals as our current, present-day selves. Our present-day self knows only what we know now, and our vision for our specific goals is limited by that.

The 1985 classic Weird Science illustrates this point well (if bizarrely). Two computer nerds hack into the government mainframe and build “the perfect woman” inside their computer. A freak electrical accident brings their design to life. They name her Lisa.

Hijinks ensue, and Lisa helps the boys enjoy life a lot more. The boys get more mature, cooler, learn a lot, and eventually meet some real, live girls. Explaining Lisa to his new girlfriend, Deb, one of the boys says: “Deb, Lisa is everything I ever wanted in a girl—before I knew what I wanted. I know that if I could do it again, I'd make her just like you. Honest.”

The local maximum problem

Like Acho and the Weird Science boys, in setting goals with our current levels of thinking and being, we can easily choose a goal that is a local maximum. A local maximum is climbing a hill and ignoring the mountain beyond it. The builders of ENIAC didn’t know they were building a local maximum computer. For 1943, it was the top of the mountain, the best they could do…but there are always other mountains to climb.

In setting a goal we should slow down and take a look around…and ask if we’re setting the bar too low.

Goals are a Continuous conversation

Not surprisingly for someone who wrote a whole book on how conversations are the fundamental unit of change, and how conversations can and should be designed, I think goals and objectives are a conversation.

Normally, they are a one way conversation - present us, telling future us what we will accomplish. 

It’s clear that we need to have a continuous conversation along the way to check in:

Are we achieving what we really, really want? Is our process of achieving our goal working for or against our real objective? Are we achieving our anti-goals by being single-minded in our approach?

The Weird Science example makes me pause - and ask a weirder question. What if goals were a conversation between my present and future self? Rather than a top-down process of goal-setting, what if we had a deep-dive conversation between our present-day self, the person setting the goal, and our future selves, the person who can see what the next mountain might be?

It’s worth pausing to ask some of these questions before setting any goals:

What does future me know that I don’t? 

What does future me believe in their bones, or see clearly, that I simply can’t? 

What are the BHAGS of my future self?

Fitzgerald's test of first-rate intelligence - holding opposing ideas while still functioning - offers us a framework for approaching goals: We ought to always hold our goals loosely, since we can’t always see around them to the next mountain. Goals are not just about what we want to achieve, but about who we want to become, to live a life we love. Viewing goals as an ongoing conversation between our present and future selves, rather than as fixed destinations, frees us to grow beyond our current vision. The true art lies not in setting perfect objectives and following plans with diligence, but in weaving a delicate balance between determined action and open-minded exploration. By leaving space for serendipity - those unexpected discoveries and adjacent possibilities - we might reach heights our present selves can't even imagine. Greatness emerges not from achieving our carefully planned goals, but from growing beyond them in ways we never could have predicted.

Handle Holiday Conflicts with GRACE: A Framework for Navigating Tough Conversations

The Holidays are upon us! These times can be opportunities for family, food, and heartfelt connections—but let’s be real, they’re also ripe arenas for tense conversations that can derail the best of gatherings. Before you dive into a battle over politics or who gets to carve the turkey, consider using the G.R.A.C.E. model. It’s five easy steps to help you navigate any sticky conversations with more grace and ease.

If you really want to dive into conversation mastery, get some free chapters from my book Good Talk: it’s all about how to design conversations that matter.

The G.R.A.C.E. model stands for:

Ground Yourself and the Conversation

Right Channel

Attend to Their Perspective

Co-Create Solutions

End With Commitments

Let’s say you're at Thanksgiving dinner, and a family member expresses a strong political opinion you deeply disagree with. Or vice versa - you say something you feel any sane person would agree with, and they disagree with you, strongly and loudly. The conversation gets heated and you want to approach it constructively instead of escalating the conflict.

Ground Yourself and the Conversation

In any conversation, at any moment, we have choices: We can react, or we can pause. Before heading into a conversation that we know might be difficult, it’s a good idea to ground yourself: Why are you engaging in this conversation? What are your goals, needs and objectives? Can you align with your conversational partners on shared goals and objectives of the conversation?

Applying Grace:

Try to reset the tone by shifting the ground (or the why) of the conversation from winning the argument to maintaining respect.

"I can see this is an issue we both care deeply about. I’d like us to talk about it in a way that helps us understand each other better."

Establish shared values if possible:

"We’re all here because we care about family and spending time together."

Right Channel

Often, I find that arguments can get heated if they are happening in the wrong place - text messaging, emails, slack - are all places where reduced context can get conversations off track and spiraling out. But the dinner table, with the whole family watching? That might not be the best venue for a full-on political debate. That venue is on the PBS News hour!

Applying Grace: Ask to change the channel

Suggest a calmer, lower-stakes one-on-one conversation later, if you really want to get to the bottom of things and do some deep canvassing:

"I think this topic deserves more attention than we can give it over dinner. Can we talk more about this after dessert or on a walk after the meal?"

If they refuse to shift the conversation to later, think of “channel” in an even broader way - change the channel from the “facts” channel to the “feelings and stories” channel. Research shows that, unfortunately, facts don’t change minds, so get them to share some stories instead.

"Maybe we can both share why this issue matters to us without trying to change anyone’s mind right now…

When did you first start thinking about this issue in this way?”

Using a “time shift” question like this is a great approach to get out of the present-moment conflict and into their backstory.

Attend to Their Perspective

Deeply listen to whoever you’re having the friction with. Attend to their perspective. It will de-escalate the conversation and help you empathize with them more completely. 

Applying Grace: Seek to understand first. Ask curious, non-confrontational questions to draw out their reasoning:

"What makes you feel so strongly about this issue?"

"How has this impacted you personally?"

Acknowledge their feelings, even if you don’t agree with their conclusions:

"It sounds like this is something that’s really important to you, and I respect that. Thanks for sharing your thoughts. Pass the cranberry sauce, please.”

Co-Create Solutions

In a complex, difficult conversation, once you’ve understood their perspective from deeply attending to it, it’s possible to find common ground or ways to move forward without division. This is also an opportunity to reconnect with step one: Grounding yourself and the Conversation in a shared Why. Reconnect to that why in any solutions you propose, or invite your partner to propose solutions that align with what they see as your shared why.

Applying Grace: Offer options grounded in a shared why, together

"I think we both want what’s best for [the country/our community]. We might have different ideas about how to get there, but that’s something we share."

“What do you think is the best way forward for us today, given that we agreed we don’t want to win this argument, and that we all want to have a great time as a family together?”

If it’s clear that agreement on the issues isn’t possible, suggest shifting the focus of alignment to something you both can value, like enjoying dinner together:

"I’d rather not let this issue get in the way of enjoying our time together today. How does that land with you?"

End With Commitments

The best movies have great endings that satisfy us deeply. Ending a conversation with “Well, let’s just agree to disagree.” or “well, it is what it is” doesn’t give us a very satisfying ending. Such endings are 

“Thought-terminating clichés” which are part of the language of totalism. This kind of language ends thinking, feeling and humanity. It’s the opposite of a GRACEful ending.

Applying Grace: Find something, even something tiny, you can both align on.

Ending with commitments keeps the conversation grounded and meaningful. It’s how you make sure all that talking wasn’t for nothing—by agreeing on next steps, even if it’s just agreeing to revisit the topic later or agreeing that you both think differently. It leaves both participants feeling heard and respected, with a clear sense of where things go from here.

Saying:

"I’d love to understand your perspective more deeply when we’re both in a calmer setting. For now, let’s focus on enjoying dinner and catching up as a family.”

Such language connects us, and allows positive conversations in the future, rather than freezing it out.

Handling a Challenging Conversation with G.R.A.C.E. in a nutshell

If you’re feeling up to it, you can even use all five elements of GRACE in one elegant swoop:

Ground: "I know we both have strong feelings about [political issue], but I don’t want this to overshadow the holiday."

Right Channel: "This might be a better conversation for another time when we can really dive into it."

Attend: "When we have more time, I’d love for you to tell me more about why you feel this way—I want to understand your perspective."

Co-Create: "I think we both care about making the world better, even if we have different views on how to get there."

End: "For now, let’s focus on enjoying dinner and catching up as a family. Pass the cranberry sauce.”

Holiday dinners don’t have to end in frustration or silence!

Navigating difficult conversations doesn’t have to mean avoiding them or letting them escalate. With the G.R.A.C.E. framework, you can approach challenging conversations with thoughtfulness and empathy. When you slow down, choose your words carefully, and truly listen, you create space for understanding—even when you disagree. The goal isn’t to win an argument but to honor the relationships that matter most. With a little effort, you can keep the peace and keep the holiday spirit alive. Remember, the goal isn’t to win but to connect—and to leave the table with relationships intact and tupperware filled with leftovers.

If you’re still hungry for more tips, check out my 2022 essay on this same crucial question or check out my book, Good Talk.

11 Ways CEOs can use one-on-ones to scale excellence in their leadership teams

Founders often want to stay involved in many or even most aspects of their businesses (see the conversations over “founder mode”). However, most soon realize that if they ever want a vacation, a sustainable romantic relationship, or a sustainable, scalable business, they need to scale the capacity of the people on their leadership team to lead the organization without them.

Instead, CEOs are using this precious time to manage projects and run through a to-do list with their most senior leaders.

One-on-ones are an extraordinary opportunity to unlock the potential of your team to think more clearly, lead more effectively and to unlock growth for your company. 1:1s are an opportunity for a creative conversation (see item 10)

I know you’re busy, so here are the 11 ways you can use one-on-ones to scale excellence in your leadership teams:

1. Have them regularly. (read why below)

2. Limit the number of agenda items.

3. Get more feedback than you give.

4. Start with wins and increase your positive to negative feedback ratio.

5. Use 1:1s to coach your team to solve their own problems, not to solve problems for them.

6. Align on a time horizon to focus each conversation on.

7. Listen actively and deeply before responding.

8. Follow up on past conversations.

9. Flip who runs the show

10. Create a standard agenda with each direct report.

11. Get feedback on the meeting format.

I just saved you a few minutes!

The first four easy pieces are crucial to making your 1:1s better. If you want to know the reasons why and some research that proves the point, read on.

The real, outsized impact is in items 5, 6, and 7. These are deeper mindset shifts backed by powerful frameworks. Putting them into practice will take time, effort, and feedback to realize the real value and potential, but the possible gains are enormous.

Items 8-11 are ways to lock in the gains from items 1-7. Use these moves to make sure your 1:1s are continuously improving.

1. Have them!

Many leaders cancel or reschedule 1:1s when more urgent issues come up. But a big part of leadership is about creating stability, and keeping your 1:1s at a steady cadence is one great way to build stability. Plus, it bears fruit: research from Gallup found that employees who have regular one-on-one meetings with their managers are almost three times more likely to be engaged than those who don’t. We can guess why just having them is better than not having them - keeping the meeting as planned sends a signal that the meeting matters and that the employee matters.

Set the example for your direct reports by holding regular 1:1s with them, and ensure they do the same with their teams. 

(For more on why great leadership creates stability in the midst of change, listen to this episode of the Conversation Factory with author Ashley Goodall. He co-wrote the blockbuster Nine Lies About Work, and most recently, The Problem with Change).

2. Limit the number of agenda items so you can make meaningful progress.

If you try to talk about everything, you can’t go into depth about anything. Boil it down to a handful of items to dive into - 3-5 tops. Don’t run through the whole To-Do list!

3.  Get more feedback than you give.

A positive side-effect of asking questions to get feedback is that you’ve demonstrated you seek and can process challenging feedback. Over time, this creates trust and allows you to offer more challenging feedback to your reports.

During your 1:1s, ask questions that help you be a more effective leader for them:

• “Is there anything I can stop/start doing that would make your life easier?” 

This is a good place to start. When you’re ready, ask this varsity-level question:

• “What’s one thing you think would be really hard for me to hear, but that I really need to? I’d like to hear that feedback.”

Set the example of being radically open to feedback and make sure your FQ (Festering Quotient) is low in your relationship. Simply put, the longer you wait to talk about an issue, the more stinky it gets, for everyone involved.

(For more on the FQ and the SBIO model of giving situational feedback, listen to this podcast about The Intentional Conversations That Build Powerful Co-founder Relationships, with Rei Wang and Anita Hossain, co-founders of coaching platform The Grand.)

4. Start with wins and increase your positive-to-negative feedback ratio

Top performing teams maintain a nearly 6:1 ratio of positive to negative comments, according to HBR. It is likely that the abundance of positive comments helps create a deeply felt sense of psychological safety and the connective tissue that allows feedback to be heard as constructive rather than negative…and to be acted on, all while driving performance.

You can leave this ratio to chance, or you can choose, as the leader, to create a culture of celebrating wins. One-on-ones are the perfect opportunity to plant the seeds of that culture. Too often, I see 1:1s getting bogged down in project management and troubleshooting. Start with wins, and start creating a better feedback ratio early.

Also note: the more specific your feedback is, the better. 

Think about feedback as four quadrants, represented by the suits of a deck of cards: Hearts, Diamonds, Clubs and Spades. Feedback can be Warm (positive) or Cool (negative), and Sharp (clear) or Fuzzy (vague). Note this is not my framework! I first learned it from my friend Peter Haasz.

Giving people “Warm and Fuzzy” feedback in your one-on-ones is nice, like the Heart that represents it, but giving pieces of Sharp and Warm feedback, like little Diamonds, makes people feel really seen. An additional positive side-effect is that the more you notice and name their excellence, the more excellence you can evoke in them over time.

For example, compare these two pieces of feedback:

“Great job on that client presentation.”

vs. 

“The way you reframed the client’s objections to the roadmap shift as a natural evolution that would be a win-win took a lot of presence of mind. You really commanded the room in that moment. Great job.” 

Spend more time in the Warm-and-Sharp Quadrant than you do in the Warm-and-Fuzzy Quadrant of The Feedback Matrix, and spend time between your 1:1s collecting diamonds to share with your direct reports.

It’s best practice to give your direct reports cool-and-sharp feedback in the moment or as close as possible to whatever happened to evoke the feedback. Don’t wait for a 1:1. The Feedback Matrix above classifies cool-and-sharp feedback as the playing card suit “spades.” (Spades are what the British call a shovel). Just as a spade is a handy garden tool, think of cool-and-sharp feedback as a tool to help folks get better. Share that feedback with them when you can be cool and calm about giving them the feedback—, i.e., when you can share the feedback in a helpful, non-clubbing- them-over-the-head kind of way

5. Use 1:1s to coach your team to solve their own problems, not to solve their problems for them.

After working with me for a few months, many of the CEOs I coach ask me, “How can I work with my team the way you work with me?” These leaders see how our coaching conversations make space for their own deep thinking and strategic problem solving and they want to do the same for their teams. But these CEOs are all smart and effective problem solvers; it’s easy for them to slip back into their problem-solving habits. But, “what got you here won’t get you there.” 

In order to scale your leadership impact, you need to scale your team’s impact. That scale will happen more rapidly if you slow down and learn to coach their thinking, instead of doing it all for them. 

Slowing down and leveraging a coaching approach can feel frustrating at first. The best way to make progress with anything is to put it on your calendar and stick with it. Developing a coaching habit with your team is no different. Insert a regular coaching conversation agenda item in your standard 1:1 agenda in collaboration with your direct reports.

In short, remove the option to NOT coach by telling them you will be coaching them, not solving problems for them. Ask them to come to the conversation with the key priorities they feel blocked on and what they think their best solution options for each one are. 

Then, to help coach them to think through problems, leverage the SSOON Model of Coaching Conversations.  The SSOON model helps make their implicit thinking explicit in five simple steps so you can understand their thinking process.

1. Situation: What’s the context around the challenge the coachee is facing? A coaching stance here is to just ask more questions to uncover what’s really going on and encourage the coachee to share their thoughts and experiences fully.

2. Success: Here, the focus shifts to envisioning the desired future. The coach helps the coachee articulate what success looks like and explores possibilities that may exceed their initial expectations, often using imaginative questions to clarify their vision. 

3. Obstacles: In this step, the coach encourages the coachee to identify any barriers preventing them from achieving success. By reflecting on these obstacles, the coachee can gain clarity on what stands in their way.

4. Options: Once success is clearly defined and obstacles are acknowledged, the conversation moves to exploring potential actions. The coach facilitates brainstorming and may offer gentle suggestions to help the coachee consider various paths forward that they haven’t considered.

5. Next Steps: Finally, the coach guides the coachee to commit to specific actions they will take moving forward. This involves selecting manageable and impactful steps that can lead to the desired outcome, reinforcing a sense of accountability and momentum.

Together, these five elements help create a structured and reflective coaching dialogue, empowering the coachee to navigate their challenges and achieve their goals through clearer thinking, guided by you.

6. Create a standard agenda together, but follow the structure of creative conversations.

I talk about these phases in more depth here, but you can also read one of my favorite books, Gamestorming: A Playbook for Innovators, Rulebreakers, and Changemakers, which is the source of the delightful diagram above. 

(See below for 22 questions to use across these three phases to create your own ideal 1:1 agenda with your direct reports.)

7. Listen deeply and actively before responding.

Remember the Talking and Thinking Gap, which captures the fact that while people can think at up to 4,000 words a minute, most of us can only speak at 125 words per minute. So, in every interaction, people always have more to say than they can ever express.

For leaders, this means that in your meetings, you don’t hear everything your direct reports want to say. Plus, you’re often likely thinking a bit about what you might say in response, or something else entirely! Don’t forget this classic quote from the late U.S. ambassador Robert J. McCloskey:

““I know that you believe you understand what you think I said, but I am not sure that you realize that what you heard is not what I meant.” ”

— Robert J. McCloskey

Assume that you did not fully understand everything your teammate meant to convey.

Active listening is usually defined as making sure you heard what you thought you heard by repeating it back and getting confirmation.

To listen more deeply, try leveraging the Listening Triangle to get to the heart of what’s being said.

When you get confirmation that you heard them right (by sharing your active-listening paraphrase), ask another question from a slightly different angle to deeper into their response. The listening triangle helps you get to the heart of what someone is really saying.

Re-asking also helps create the kind of psychological safety essential for an effective leadership relationship, confirming that you really want to understand their perspective.

8. Flip who runs the show.

Share your plan to coach more, and share this article with them so they know the game plan you’ll be sourcing from. Sketch out an agenda together (Item #6!) then hand the agenda over to them and let them take the reins. This eliminates almost entirely the possibility of backsliding on your intentions!

9. Align on a time horizon to focus each conversation on.

Often, 1:1s can get stuck in the now—the immediate challenges of a company’s day-to-day survival and growth—which is natural. 

In fact, most people are encouraged to focus on the most urgent and important items on their to-do list. This is a trap! The idea of focusing on the urgent and important is a mis-application of a speech by former president Dwight Eisenhower in 1954. In the speech, Eisenhower was quoting Dr. J. Roscoe Miller, President of Northwestern University, as saying:

““I have two kinds of problems, the urgent and the important.
The urgent are not important, and the important are never urgent.”
”

— Dr. J. Roscoe Miller

This "Eisenhower Principle" is said to be how he organized his workload and priorities. For years, I was told to focus on the Important/Urgent quadrant (in red, far left) as a first priority and to delegate or ignore the Not Urgent/Not important (in blue, lower right on both matrices below). But the quote is actually pointing us to the upper right yellow-green quadrant - the NOT urgent YET Important quadrant. 

These NOT urgent YET Important items are the ones that easily fall off a to-do list filled with urgency but lacking items that address longer-term or even medium-term strategic impact.

Working with your leadership team to focus weekly or bi-weekly conversations on the non-urgent but important items will slowly create a buffer against the tyranny of urgency. The matrix on the right is the ideal Eisenhower matrix - intentionally making ample time for the non-urgent as the lion’s share of our focus.

Make sure you use periodic conversations to look even further ahead - where does this person want to be in 10 years? In five? Where do you both see the company in three years? Shift the time horizon for each conversation intentionally.

10. Follow up on past conversations.

Make sure topics and issues don’t dangle. Following up on past issues with your direct reports will remind them not only to stay accountable to you, but also to follow up with their direct reports so that they remain accountable too. All of it trickles down to create a culture of accountability organization-wide. I hosted a lovely podcast conversation with the co-founders of Huddle who called this shift "building an Integrity Culture" - a culture where you expect yourself and others to do what they say they will. Listen here.

11. Get feedback on the meeting format.

Regularly check in with your direct reports and ask them: Are you getting what you need from these conversations? What’s working? What could be improved? 

As mentioned above, you will find that the unique needs of each member of your team will shape the 1:1s over time, even though they will all follow the same open-explore-close architecture.

22 questions to try out in your 1:1s

Questions are the rocket fuel of conversations, and 1:1s are no exception. Here are some tried-and-true questions to take for a test drive on your next one-on-one, organized according to the open-explore-close pattern of powerful, creative conversations:

Opening:

1. The “Traffic Light” check in. 🚥 Are you Green (all systems go, full speed ahead), in the Red zone (ie, having some significant challenges you’re managing that are stopping you in your tracks) or yellow (ie, you need to slow down to stay safe)

2. What has your attention right now?

3. What's driving you crazy these days? 

4. What's making you happy to come to work these days? 

5. What is the general mood and morale of the team(s) you're on? 

6. How are things outside of work?

7. How is stress at work?

8. How is your workload at work?

Exploring Key Topics:

1. Progress towards goals:

a. What Victories do we need to celebrate? 

b. What are some important Roadblocks we need to remove?

2. Career development:

a. Where do you want to go? How are we going to get you there?

3. Coaching questions:

a. How can I help (with challenge X)?

b. What does “good” look like? What’s your real goal?

c. What’s the real challenge for you here?

d. If you're saying yes to this, what are you saying no to? (nod to Michael Bungay Stanier for this powerful question)

e. Check out the SSOON model of coaching to make sure you lead a coaching conversation effectively.

4. Feedback for the leader:

a. What’s one thing you think would be really hard for me to hear?

b. Anything I'm doing that I need to stop? 

c. Anything I should be doing that I'm not? 

d. Anything I'm doing that I should keep doing?

e. What should I be doing more of, or less of, to make your experience at ___ the best it can be?

Closing:

1. What's your next step?

2. What was most useful to you?