Leadership Design: How To Design a Better Boss

I’ve had over 30 jobs in my life and that means I’ve had 30+ bosses, leaders, and managers to deal with. I’ve worked for almost every kind of boss you can imagine: the boss who shouts orders, the boss who seems to care but fails to back you up, and the boss who is a genuinely compassionate person. 

Over time I began to realize that all leaders, like apps or buildings, have a certain design. Some of the ones I worked for had a leadership design that made doing work easier and my office life enjoyable. While others had such bad leadership design that not only was it hard to do good work, it made me not want to work at all. 

When I became a coach and started coaching the kind of people I used to work for, I started to wonder what might happen if you applied design principles to leadership. 

Could you design a better boss?

Here’s what I found:

Leadership as a Function of Design

Adobe identifies 4 golden rules of User Design¹:

  1. Place users in control of the interaction
  2. Make it comfortable to interact with 
  3. Reduce excess guessing and thinking
  4. Make the experience consistent

These are all great standards to create a positive user experience. But they are also great standards for good leadership design. 

1. Place users in control of the interactions:

Most founders, CEOs, and Senior managers I coach try to control the people around them. 

They think, “if I can just get them to do what I want them to do then I’m a good leader”. The result is that they end up bullying or pressuring their teams to work as they do. But great leadership isn’t about creating clones, it’s about inspiring people to bring their best selves to work.

If you want to create a good user experience, you must work to let the users have enough control so they can do what they want while also creating the right kind of boundaries so they don’t get lost or confused. This is exactly the same for great leadership.  

If you give your team clear boundaries, goals, and expectations while encouraging them to do their best work, come up with creative solutions, and feel responsible for what they contribute, you’ll have a team that is committed, focused, and inspired. 

2. Make it comfortable to interact with.

If you were scared to use an app, you would never open it, if you were afraid that your coffee maker would kill you, you’d buy a new coffee maker. Good design means a design that is helpful, unobtrusive, and comfortable. 

But most leaders don’t get this. They don’t understand that fear is the #1 motivation that exists in the workplace. They don’t get that people are afraid to be honest because they might get yelled at or fired. They don’t get that people are afraid to take risks because they’re worried their boss won’t have their backs. 

Great leaders understand what’s at stake for their teams and work to make their teams comfortable in working through challenges together. 

They demand respect by setting clear expectations and standards, but they are also open to challenges to their thinking, direct feedback, and radical candor. These leaders understand that if the team trusts their leadership they will work better together especially when hard choices have to be made. 

They don’t let fear go unchecked, instead, they choose to be responsible for the impact of their leadership and they use that responsibility to inspire the team to work together. 

3. Reduce excess guessing and thinking

I’ve worked with leaders that think out loud so often that their teams don’t know what strategy to follow. I’ve also worked with leaders who keep everything so close to the vest their teams are shocked when they suddenly change directions or tell them they’re very disappointed in the work they produced. 

The problem is the same in both cases, the team doesn’t understand what the leader wants. 

Great design might challenge the user to think harder or come up with a creative solution, but they never ask the user to do more guessing or thinking than they need to. 

Great leaders also challenge their teams to come up with creative solutions and do inspiring work. 

4. Make the experience consistent

The last principle of both user design and leadership design is consistency. Great leaders have to ensure that the consistency is both inward and outward. The company culture is being reflected in a way that individuals feel comfortable and at ease (rather than walking on eggshells) and the mission is being consistently utilized.

When leaders are all over the place, it makes for a bumpy ride for the team members. One that prohibits successful work and instead projects the leader’s needs over the company’s.

I’m not saying that the environment has to be cold and heartless, or that the leader should act without emotion. I’m saying that the general goal of both the business and the company culture should be at the forefront of the decision-making and execution within the business.


The goal for leaders today is to get results. However poor leadership design leads to poor morale and experience for the do-ers in the company. As a company continues to grow, the leadership should do so as well. I have no doubt that the design elements listed in this article will continue to play a role in a good leadership design. Placing the user at the front, making it comfortable, reducing guesswork, and being consistent are the ways to design a good boss.



5 Hustle Questions That Could Save Your Life

To be successful you’ve got to hustle right? I mean that what separates the truly dynamic and successful people in any industry, Musk, Bezos, Zuckerberg, Gary V, Tim Ferris, etc., etc. they ALL HUSTLE.

So if you want to know if you’ve got what it takes to be successful answer the short 5 question quiz below

Are you more committed to working and making it happen than close relationships, rest, etc?
Do you take work to bed? Work on the weekends? Do you find time to hustle on vacation?
Do you prefer to talk about your hustle more than any other topic?
Do you get impatient with people who don’t get why you’re so focused on hustling?
Do you think about hustling while driving, conversing, falling asleep, or sleeping?

If you answered yes to most or all of these questions then you are truly aligned with hustle culture. But you might also be a workaholic.

That’s because these questions are actually adapted from the workaholic’s anonymous website. They’re 20 questions to help you see how you might be using work as a way to avoid your feelings, fill a vast and empty hole inside of you, and generally give you a sense of self or worth.

But Hustle culture isn’t all bad.

It’s based on a simple idea: Anything is possible with hard work and determination.

And this idea at its core is a good idea. Too many people believe that they can’t create the lives they want because they lack the education, connection, skills, or background to create what they want. This fundamentally isn’t true. In fact, it’s something that I work with clients on regularly.

But hustle culture also ignores the fact that being white, male, having a good education, and access to good credit or sources of funding all have an outsized effect on your ability to make hard work, work for you.

It also ignores the fact that overworking as a way to create identity is dangerous, because if your identity is all about hustling then you can never stop hustling even after you’ve achieved success.

The danger of endless work.

About 3 years ago I identified myself as a workaholic. Of the 20 questions on the WA website, I answered yes to 12-15 of them. It was a wake-up call; it helped me see that work had not only become problematic for my health and well-being, but it had also become the center of my identity.

I realized that life wasn’t supposed to be just about work for work’s sake. I also realized that my health, especially my mental health, wasn’t worth the rewards of overwork. Yes, I liked making good money as a coach, but I didn’t love the hours of stress, the outbursts of emotion, the fights with my cofounder, and the endless sense of anxiety and pressure I felt.

I realized that life isn’t worth overworking through. So I changed my business. I slowed down. I took more time off. I figured out how to be more effective while working fewer hours. And now I work 4 days a week and make the same amount of money.

I sometimes still feel left behind by hustle culture. I feel like I should be working harder, especially when my partner stays up till 7 pm finishing her own work, or when a friend of mine completes a big project after working long hours and nights… I wonder if I should go back.

But then I remember that it isn’t worth it.
YES, I need to work hard.
YES, I need to serve my clients.
YES, I need to be on purpose and generous with my time and efforts.

But that doesn’t mean I need to go back to hustling so much that I lose myself.

You can be successful by applying yourself, working hard, and being persistent as all get out. You do need discipline and endurance to be a successful entrepreneur.

What you don’t need is to be shamed for taking care of yourself. It’s why I always have a coach that pushes me to work harder when I slack off or I’m avoiding what needs to be done, but who also advises me to get rest when I push too hard.

So get supported, stay focused, and when the noise that you should be working harder enters your head, check to see where it might be right, and let the rest of it go.


Solve Conflict In 1 Conversation By Following These 7 Steps

I lead teams, leaders, and cofounders through difficult conversations. Issues that they’ve left festering for years, elephants so big hardly anything else can fit in the room, and grudges older than the movie ‘the grudge’ are my jam.

You learn a thing or two about how to deal with conflict when you seek it out for a living. And the #1 thing I’ve learned is so simple that I still can’t believe how much like a Jedi Mind Trick it clearly is.

Here it is: Listening and reflecting back on what you heard

I know you think you know this trick.

But you don’t.

Even though it is the most basic communication concept almost anyone has heard, nearly every leader, cofounder, and team I’ve worked with fails to do this.

The result is that people don’t feel heard. And when people don’t feel heard they repeat themselves. They get defensive. They bring meetings to a standstill. They fight back. They get frustrated. THINGS STOP WORKING!!!!

And when I teach my clients (executives, entrepreneurs, team leads, and team members) how to do this AND they actually do it regularly. EVERYTHING GET’S EASIER!!!

So here it is.

Step 1) Listen to what someone is saying.

DO NOT LISTEN TO YOUR INTERPRETATION!!!! You will have judgments, assumptions, feelings, responses, and so much more. Set those aside. Just listen to their words. If taking notes helps, take notes.

I know there’s context and subtext. Your mind will hear those and add them. You don’t need to add extra work to them. Let that be and listen to the words.

Step 2) When they’ve said a good chunk of something, pause them.

What’s a good chunk?
Well, it really depends on your memory, but it’s no more than one subject. If they have a complaint about the sales team and about the customer success team, pause them after the first point of their sales team complaint.

You can do more but really less is better. Again take notes if it helps and it usually does.

Step 3) Reflect back what they said.

“So what I’m hearing you say Brenda is that when John changed his mind quickly about the marketing budget you felt confused and uncertain and weren’t sure how to proceed.”

Repeating is not agreeing.

Repeat it with me now. Repeating is not agreeing.
You can repeat for clarity without agreeing. Trust me. It works.

Step 4) Ask, “Did I get it?”

This gives the person you’re listening to a chance to say yes or no. They might say no even if you said it VERBATIM! That’s because people often don’t really know what they are saying until they’ve said it.

So brush it off and listen again.

Repeat steps 3 and 4 until they say YES you got it!
And very often they will feel incredibly relieved just to have you hear them.

Step 5) Ask “What else?”

Since you paused them they might have more to say. So ask them what else they have to say.

Then go back to steps 1-4 after each chunk you will ask Did I get it? They will say YES!

Ideally, this will go on for 3-4 chunks. If you need you can set a time limit or subject limit for what you can hold (it’s ok to not try to listen to everything at once)

But at some point they’ll say, nope that’s everything.

Then you move on to step six.

Step 6) Summarize and Empathize

Now you’re going to give a brief summary of what you hear and imagine how it felt for them.

Ok so Brenda what I’m hearing is that
You felt frustrated and confused when John changed the budget
You tried to talk to him about it but he didn’t seem receptive
So you tried to fix it on your own but you got stuck.

Is that right?


Yeah, I totally get that. I can see why if you felt confused to start and didn’t feel like you could reach out for support why you’d feel frustrated and unsure. It makes a lot of sense why you’d feel that way.

Here’s the KEY to this step. You don’t have to agree with the facts. All you have to do is say, from the way you saw the world. I understand why you would feel the way you do.

This is a form of validation.

We can argue over facts. Maybe John did respond to Brenda but she missed his message. Maybe the budget was clear but wasn’t communicated well. None of that matters.

Brenda had feelings about all of this. And those feelings are real and valid. When you validate Brenda’s feelings Brenda feels human and appreciated. Any problem you now need to work through becomes easier when people feel this way.

After that, you are ready to move on to step seven.

Step 7) Now Deal with the Challenge or Problem at Hand.

Make a place of action. Make a final decision. Move the ball forward. Come up with a solution that works for everyone involved.

Listening in and of itself may not solve everything, but it creates an incredible foundation of trust for solving things.

When I lead cofounders through this 55% – 60% of the problems seem to vanish. Yes, there are still 40% of the problems left, but they can be worked through.

When I use this with team members that are resisting a decision a company needs to make, they almost always go along with the group on moving forward. And when I have team members do this to their bosses, their bosses almost always become more open to hearing new points of view.


It’s magic because deep down we all want to be seen and loved. It’s cheesy but it’s also fundamentally true. When people feel seen and appreciated they behave more generously and kindly. Making people feel valued is a hallmark of great leadership.

So practice it. Learn to listen and reflect. It’s simple though not always easy but if you learn to do it well I assure you it will become a superpower that you can use almost everywhere you go.


Entrepreneurs, You Are Your Own Two Person Team

One of the biggest challenges when you run your own business or even when you’re the leader of a larger team, is that very often you have two roles or ways of being. Each role is different and vital, but because they function so differently if you start to mix the two you’ll likely find yourself paralyzed with doubt and uncertainty. Here’s the make up of your two person team.

Role #1 – The leader or CEO

The job of the leader is to figure out a clear and compelling vision. The leader might generate the vision from themselves or source it from the team. How you get there doesn’t matter. What matters is that you see something that you want to create and it’s clear, compelling and meaningful to you (and your team if you have one).

Once the vision is set, the leader stands for that vision, plans for that vision, and enrolls others into that vision.

As time passes they need to notice what is and isn’t working, uncover the breakdowns, and shift the plan.

Role #2 – The doer or executer

Even if you’re fully a CEO, some of the work you do will be as a doer or executer

The job of the executor is to do the best job they can, based on their current understanding of the strategy and requirements that have been set forth by the vision.

If they run into problems they need to note and report them. They might come up with creative solutions, ideas for trying new things, and even lead their own efforts inside the context of doing.

They can still have the being of a leader and be standing for something, but their focus in this role is on executing based on what has been decided by the leader or the group.

Two Person Team: Final Thoughts

The problem SO many CEOs, start-up founders, freelancers, small business owners, and coaches face is that they try to do both of these at the same time.

They decide to try a strategy of reaching out to potential clients who might want big projects to boost revenues.

They do a few phone calls, ask for referrals, and they get a couple of no’s. Because it’s hard to hear No’s they start to doubt the strategy. They think well maybe I should just go after some smaller clients instead, so they switch to that, maybe they get a few jobs, but there’s not enough money and they realize that isn’t working. So they think about the bigger job clients again.

Pretty soon they feel discouraged, trapped, and uncertain.
But if they were two people or if they better understood the two roles (Leader and Do-er), this wouldn’t happen.

The salesperson might tell the CEO that they were getting some no’s and the CEO might ask about the number of calls or what kind of response they had gotten. They probably would tell the salesperson to keep going until they made 25 or 50 calls so they have enough information to see if the strategy was or wasn’t working.

The salesperson would keep going because they had the support of the CEO who was standing for the vision and focused on the information and feedback needed to make a good call.

The CEO may start to think of other strategies but would trust the salesperson to do the best job they could and learn as they went along, knowing that it takes time to test out any strategy.

The challenge is that we are NOT two people.

The doubts of the salesperson can become the doubts of the CEO and vice versa.
The critical eye of the writer can become paralyzing to the writer.
The fears of the coach can undermine the trust of the marketing manager.

This is why if you’ve got a job where you have to be in both roles, YOU’VE GOT TO LEARN TO SEPARATE THEM!!!

You can do this by trading off days.

On Monday I’m just a salesperson for my company. I’m going to get on the phone, or on my email and try to make it rain.
Then on Tuesday morning I’ll sit down with myself and do my best work.

You can do this by having different spaces.

I do my writing in my living room chair and I DO NOT EDIT.
I do my editing at my desk where I do my other admin tasks.

You can even try different outfits or hats (physical or energetic).

When I put on my dress pants I’m the CEO of my company and I’m setting the strategy.
The rest of the time I’m a worker on my team and I’m focused on getting the day-to-day done.

And YES I’m fully aware the two will bleed into each other in certain places.

That’s ok. The key here is to do your best to notice where your head is at and ask if it’s where it needs to be.

To do anything well you need both the vision and the courage to execute that vision.
But you have to remember that courage sometimes means staying the course even when it’s hard. And sometimes it means taking a hard look at the strategy even when you don’t want to admit it isn’t working.


How To Be Free: The Three Types of Freedom

We all want a sense of freedom. The ability to do what we want, pursue our dreams and feel present to a life full of adventure and possibility.

But most of us have no idea what being really free actually means.

When I was a teenager being free meant doing what I wanted.

Freedom to stay out late, to date who I wanted to date, to keep my door closed, to drive faster than the speed limit, to skip the homework assignments I thought were stupid or that I just didn’t want to do.

For some people, freedom is just that. Not wearing a mask. Buying a fake vaccine card to get into a restaurant. Cheating on their partners and hitting on servers.

Sometimes their justifications are more complex but the desire to be free is the same. It seems juvenile because it is. It’s a juvenile idea of freedom dressed up in politics and business suits.

Most people who have developed some maturity and empathy see that this form of freedom is limited. The joy of doing what you want doesn’t last long and the pain you cause others isn’t worth it. But not all of us learn this.

When I got out of college and started paying my own way, freedom meant being able to live the kind of life I wanted.

It meant I could pay my bills, I could choose where to go to dinner, or where to go on vacation.

Part of why I started my own business was because I wanted more of this freedom. The freedom to choose when I worked and who I worked with. The freedom to change my location or to do list at will.

I sought the freedom of a particular kind of lifestyle, which while motivating also ended up feeling a bit empty.

But many people stay focused on this kind of freedom as long as their alive.

Part of the reason the great resignation has happened is that the corona virus destroyed the false trappings of this kind of freedom.

Without boozy brunches and business trips many of us started seeing that lifestyle freedom didn’t mean much unless we had constant freedom of movement and an endless supply of distractions.

Working a crappy job to pay for a decent vacation isn’t worth it. Sure losing the vacation made that become clear, but even when we could take the vacations it still isn’t worth it.

I came to realize how empty this kind of freedom was when I achieved more than most people do as a business owner. I consistently earn multiple six figures a year and live on a portion of that with ease. But I still wasn’t really enjoying life that much.

Which is how I stumbled on the third kind of freedom. What I call spiritual or energetic freedom.

It’s the freedom to be or become anyone I want. And I’m not talking about becoming an astronaut.

This isn’t about achieving some title or some state of mind. It’s about the ability to embody any energy the moment calls for. It’s about being able to be my darkness fully. It’s about being able to fully embody my sexuality and desire. It’s about being able to fully embody deep wisdom or deep foolishness.

This is the next level of freedom.

I touched this kind of freedom when I lived at a zen monastery for two years, but without the kind of lifestyle freedom, I craved.

It was only after achieving some of the lifestyle that I wanted that I was able to really see how meaningful energetic freedom really was.

Energetic freedom doesn’t depend on roles or status. It doesn’t depend on age or attractiveness. It’s the most generous kind of freedom, because it’s a freedom that allows you to respond moment to moment in whatever way serves the most.

And yet it’s a kind of freedom very few people talk about because it’s so hard to understand.

So many of the CEOs I’ve coached have achieved full lifestyle freedom but feel trapped in themselves.

So many celebrities live lives of glamour and wealth but seemed hemmed in by their own personalities and habitual ways of being.

At a time when so many of us still can’t go on vacation or return to our normal lives how are we supposed to continue to pursue freedom?

It’s time for us to pursue a freedom of being, a freedom that is accessible to everyone and helps improve the lives of everyone we meet. It’s a freedom that demands humility and practice, but rewards us with a flexibility of thinking and responding, unlike anything we’ve ever known.

If you’re ready for something new consider exploring what it would mean to let go of a fixed idea of who you are and embrace more of yourself not only to experience greater personal freedom and joy, but also so you can give more of what the world currently needs.

Which is people who are brave enough to stand up for something that comes from an authentic care for others and a willingness to not take things personally and instead do what most needs to be done.


You Don’t Know What You Want: Strategies for Uncovering Desire Hidden in Plain Sight

When I met Madeline she was already incredibly successful. She made more money than most of her friends, had a position with a decent amount of power, and had left a busy life in Paris to live in her dream city by the coast. But she was unsettled.

We were talking because she wanted to become a coach. Or at least that’s what she thought. As we spoke I learned a lot about her. Failed relationships. Boredom with her career. A pent up desire for adventure.

No matter what she tried, something was missing. She had just had her heartbroken by a gorgeous man and it left her questioning everything.

Again and again, we returned to a singular question. A question she struggled to answer.

What do you want?

In a world where our desires seem rampant, many of us still don’t know what we want. We look through pictures on social media and develop an anxiety that we’re missing out on life, but we forget to ask ourselves if what we think we’re missing out on is what we actually want.

Working full time as a coach over the last five years I’ve met all kinds of people. I’ve worked with a CFO from Nokia, the founder of a Marketing Agency in Peru, and a single mother in the UK.

Despite their diverse backgrounds, educations, and experiences they all had the same problem: none of them knew what they wanted. They had goals, ideas, and dreams. But as soon as I pushed them, as soon as I asked, what do you want?, I was met with a familiar look that conveyed a hidden confusion and doubt.

We’re out of touch with our desires.

Maybe it’s the endless opportunities we have. Maybe it’s the constant competition for attention. Most of us are out of touch with what we desire.

For a while, from secondary school to a few years after college graduation some of us are lucky enough to live out a parental script that offers a level of certainty. Get this degree. Apply for that job. Marry this person.

Before long though each of us wakes up wondering if it’s really what we’ve been working towards.

And the pandemic and economic crisis have only sped up this process. Over the past two years a lot of us have been questioning the point of our lives as we watch Netflix in our parent’s basement or zoom into another pointless meeting. And outside of work many of us are wondering why we pay high rent in a shut down city or why we’ve chosen friends who we struggle to connect with when we can’t go out for drinks like we usually do.

But even before the pandemic, this was an issue.

Chasing our desires is born of privilege

Desire chasing is almost entirely a first-world problem. Your perceived options in life are often dictated by your class, race, gender, and education. But the problem of limitation exists for all of us. We all limit what we want to what we think we can have. So much so that many of us never really ask unbounded questions about desire. And when we do, the answers scare us.

You can begin to find out what you want.

But it doesn’t have to be like this. It takes courage. It takes patience. It takes humility. But you can begin to discover your true desires by asking yourself, What do I want? If I could have anything, what would that be?

And while you may have to ask a few times before you get down to what you really want, here are some things you can pay attention to as you begin to explore. ​

1) Ignore the status and wish lists

Often when I ask my client what they want, I get a Christmas list of desires.

A partner with six-pack abs, a seven-figure job, a penthouse overlooking central park, a Ferrari. There’s nothing wrong with these desires. Having them as goals can be motivating. But I’ve coached people who have some of these things. Most of them aren’t happier than you already are.

We think things, status, money, and power will make us happy. And up to a point, they can increase our satisfaction in life. It’s harder to enjoy life with few resources and options, but they rarely lead to the deep satisfaction you’re looking for. ​

2) Focus on the experience

What is the experience of life you want to be having? If you desire wealth is it because it gives you a sense of security? Freedom? An ability to say no? Or maybe the ability to explore the world?

Hidden behind most of our desires is an experience we’re craving. All the ‘stuff’ we focus on is really just a strategy for having that experience.

Sometimes this strategy works, but often it doesn’t. If you can get down to the experience you’re craving, usually, you can think of a variety of ways to create it, which gives you a lot more options as you move forward.

3) Let go of old scripts

We’re taught to listen to what other people want first and then decide what we want.

That’s basically what school is. Choose from these five books. Take one of these two classes. Most of our lives we’re told to achieve based on the standards of others. But those standards often leave us extrinsically motivated and unsatisfied with life.

This is why I often help clients look at and examine what things they were told to desire growing up. These stories of scripts of success can give us clues to how we originally formed our ideas of happiness and satisfaction.

Sometimes these scripts are helpful in guiding us towards better choices, but just as often they trap us in a set of standards and ideas of success that don’t really resonate.

By looking at these scripts closely you can decide which ones to honor and which ones to sidestep so you can focus on what’s truly satisfying.

For our grandparents finding steady work and a reliable paycheck may have brought safety and satisfaction, but that may not be true for you today.

For our parents finding a partner and settling down to have kids may have given them a sense of purpose and home, but that may not be what gives us that same sense.

The purpose in examining these scripts isn’t to discard them, it’s to better understand the ideas and beliefs that informed our earliest life choices so we can either choose back into them consciously or discard them altogether.

4) Accept some level of complexity and suffering

On a fundamental level, we all want to avoid suffering. This is a truth so old the Buddha and many other sages called it out millennia ago.

The thing we seek to be free from suffering varies for each person and even for different phases in life. When you’re young you might be certain that getting into your first choice college will guarantee your happiness. As you get older it may be finding the right partner. If you run a business it could be finding product/market fit, or even hiring the right team.

But it seems no matter what you do and regardless of what you get or don’t get things don’t ever seem quite right.

That’s because life is complicated. Things are always changing and even getting what you want may not bring you the deep satisfaction you’re craving.

This is why even as you seek to create what you want, it’s important to remember that your desires and your receiving are incredibly complex.

Honor the complexity of you and your life and learn to appreciate that while understanding what you want can help you feel a sense of deep satisfaction and fulfillment, it’s not a panacea. It’s simply a guide post for living a life full of purpose and joy.