What makes a bad leader? – Part 1

Part 1 – Bad leaders listen from anxiety.

The first bad leaders I met were teachers. I was a precocious and challenging student. I would object to lessons, I would speak up in class, I would be deeply engaged, and then suddenly bored.

The best teachers understood the kind of student I was and used my curiosity to help deepen the topics we were learning and when it was time to move on they let me know. I would accept their guidance because they accepted me.

The other teachers, the less good ones, were threatened by me. They were anxious, insecure, and just wanted to get through the day. They would try to quiet me down and as a result, I would only speak up and push back more. Everything got worse for both of us.

Working with someone who is brilliant but wiley can be a double-edged sword. They do amazing work, but they also challenge you more. If you’re solid in your leadership you can harness this energy for good.

So what’s the key to success?

Learn to listen from confidence and curiosity.

When you listen to challenges and accept them, people feel seen and heard. And what’s amazing is that this is the main thing they need. You might think they need you to agree with them, or put their ideas into action, but often they don’t. They just want to be given a fair shot to make their case and once they are heard they will accept the decisions you make.

But so many leaders never learn this. They feel threatened when their worldview or choices are challenged. Then from insecurity, they tamp down innovation and new ideas and they squander the brilliance of their most innovative teammates.

If you’ve got a brilliant but wiley member of your team or you want to stop complaining about how people won’t drop things or that your team isn’t engaged enough. Try simply listening and accepting people’s ideas. Make sure they feel seen and heard.

You’ll be amazed at the team and energy it creates.


Should I hire a technical guide or a thinking partner?

Every kind of leader needs two kinds of support if they want to lead well and produce results. 

  1. Technical advice or mentorship 
  2. Thinking partnerships 

So why might you want technical advice?

We need technical advice when we don’t have experience in a certain area. It’s why boomer parents ask their kids (and grandkids) for help with their iPhones. It’s why new founders want the advice and counsel of former successful founders. 

Technical advice is helpful because it allows you to tap into the experience and wisdom of someone who’s gone before you. They’ve made some mistakes and learned some lessons that you can use for yourself. 

But technical advice has pitfalls, like survivorship bias

Yes, this person was successful but you usually don’t know that much about why they were successful. It could be that they were brilliant, savvy, and strategic, but they also could have gotten lucky. Usually, success is a mix of skill and luck and the challenge is that you don’t know how much of their success was based on luck vs skill. 

In the extreme, it’s like asking for advice on how to win the lottery from a lottery winner. The winner might have a method but that method doesn’t account for much. So when you seek out technical advice or mentorship this is something that you need to account for. 

Another challenge is the context gap problem

Different things tend to work in different contexts. And the likelihood of something (a strategy or a tactic) working again correlates to how close the new context is to the old one. 

That’s why you’re likely to get the best advice on how to build a table from someone who has built lots of tables. You could also get advice from someone who has built chairs and the advice will probably still be decent (because chairs and tables are pretty similar). But if you ask for advice on building a table from someone who carves small statues out of wood that advice may not be very helpful. It could even be harmful in some ways. And while this is obvious it becomes more subtle as your increase complexity. 

When it comes to businesses and startups the context can change in a lot of different ways. The market is never the same, the investor pool is different, the industry has matured, and government policies have shifted. 

So even when the context is similar you’ll always have to filter for these changes and adapt the advice based on your situation. Because while technical knowledge and mentorship are a total game changer for most people, they can also give you some bad data when you’re trying to chart a path forward. Especially if you over-rely on it. 

So that’s the power and challenges of technical advice and mentorships. 

Now let’s talk about thinking partnerships.

There are a bunch of ways to create thinking partnerships but the two most common are masterminds and coaching. 

Both of these work in a similar way. 

  • You bring a problem or challenge to the table
  • The person or group asks questions and reflects what they see
  • Through that process, you clarify your thinking
  • You come up with novel solutions or experiments
  • And you get access to blindspots and insights that are hidden in the process itself or your thinking about the problem or opportunity. 

The best thing about thinking partnerships is that they help you think better, be more creative, and they tend to help you grow more personally than mentorships. 

The big reason for this is that they push you to reflect on yourself and your thinking and as a result, you can’t help but begin to notice patterns of thinking that might be holding you back. 

The main downside to thinking partnerships is that they mostly rely on your previous knowledge and experience in order to help you make better decisions and gain better insights. 

If your assessment of the situation is wrong or there’s something obvious you’re missing, they can lead you down the wrong path. Then again thinking partnerships aren’t as subject to the cognitive biases of mentorships. 

Because the purpose is robust thinking and personal development you tend to base your decisions and strategies more on what’s happening in your situation rather than on some past model that no longer applies. 

So which one should I hire? 

If you want to be successful you tend to need both. 

You need someone with experience that can help you avoid making mistakes but you also need thinking partnerships that help you grow and develop your ways of thinking about the business or project you’re running. 

Here are the questions I usually have people ask when they aren’t sure whether to hire someone who is an excellent thinking partner but lacks subject area knowledge or if they should hire someone who is an expert in an area but may not be as good of a thinking partner. 

1. Right now how many of your challenges are technical in nature?

Let’s say you’ve got a software problem at your SASS or your code is bad and you don’t know how to fix it. 

If you primarily have technical challenges, working with a technical guide is better. But if your focus is on things like leading people well, enrolling key stakeholders, or clarifying a vision then a thinking partner would be better. 

2. Can you get technical guidance someplace else?

Ironically I’ve found it’s easier to get technical guidance (for free) then really good thinking partnerships. The internet is filled with advice and people love giving advice. As a result, you can usually find information about the industry or problem you’re working with. 

What I’ve seen is that growth is usually not stopped by a lack of experience but an inability or unwillingness to try various tactics and approaches to solving a problem. I’ve also found that finding someone that really helps you think better and who won’t just give you advice is much harder. 

If you can’t get technical advice easily on the challenges you’re facing then go hire someone to give it to you, but if you can get some advice or support from well-known sources or a trusted mentor you’re going to be better off working with a well trained thinking partner like a coach. 

3. Are you stuck on a lack of knowledge or a lack of action/enrollment?

If the big barrier to moving forward is knowledge or risk mitigation hire an expert. It will be worth the investment.

BUT if there are things you know you should try and you aren’t or can’t get your team onboard then you probably need a thinking partner. Because these kinds of challenges tend to be a result of approach or style rather than a lack of data or experience. 

4. Is it better to get the right answers or ask the right questions?

If you need answers to key problems this is when technical guidance can be a great shortcut, but if you’re not asking the right questions thought partnership tends to be better at framing problems in new ways. 

Another way to think about this is, Are you trying to learn the standard way or develop a new way? If you want to know how things have worked expertise is better, if your focus is innovation thinking partnerships are better. 

5. How important is short-term growth/results vs long-term growth/personal development? – 

If you want or need results in the short term experts are great! In fact, they are often much more reliable than thinking partners in the short term, because they know what will work the fastest (assuming the context is similar enough).

But if you want to grow yourself as a leader, hone a culture, or gain insight that your team can use for a long time, thinking partnerships tend to be better. 

The reason is simple. Thinking partnerships ask you to do the work of thinking, considering, experimenting, and learning. Because you don’t take a shortcut, you learn more about the journey and the territory you’re in. It may be harder in the short term, but there really isn’t any replacement for personal experience which is why thinking partnerships are so potent. 

Still, sometimes you need to make changes fast and adjust quickly so urgency is an important factor to consider. You can create fast results with a thinking partner, but an expert might be able to give you a guide to what’s worked before so you don’t have to reinvent the wheel.

Final Thoughts:

In reality, you need both of these things if you want to achieve your goals. You need to learn from others experiences and you also need to develop your own way of thinking. 

If you rely too much on experts your thinking isn’t as creative or innovative, but it may be easier to get started. And if you rely too much on thinking partnership and ignore the inputs of experience you might risk falling into common pitfalls. 

The bottom line is that you need to find a way to have both. Some founders use their investor networks to tap into experience and hire a coach to help them with their thinking and growth. Other founders, leaders, and entrepreneurs hire consultants to give them valuable expertise and then form informal coaching or mastering relationships with their peers to hone their thinking. 

No matter what you’re approach is it’s important to not neglect either side of this equation. A great coach or thinking partner is usually harder to find (though you can find ok thinking partners with more ease) and will help you grow much faster than you if you just work with experts or try things out yourself. But experts are incredibly valuable for solving specific problems and helping you learn without making mistakes yourself. 

So don’t settle. Get creative. Find amazing thinking partners AND get the advice you need. Don’t choose between the two simply find a way to experience them both. 




How fast can you let things change?

I’ve noticed that most people are unwilling to believe that things can change quickly. During times of prosperity, we tend to assume that they will continue indefinitely. Conversely, when facing difficulties or obstacles, we tend to believe that they will persist indefinitely.

But change often happens quickly and when we least expect it.

What does that look like? 

About 6 months ago, my partner and I were looking for a new place to move into in Salt Lake. We had viewed a dozen places and what we found was depressing. 

Most of the places in our budget were just alright. They ran the gambit between too small and in a good part of town or bigger but in a part of town we didn’t like that much. 

Some of the places were scary and yet somehow still quite expensive. We were about to give up and renew our Airbnb for another month, when I found a newly listed place with amazing views of the Salt Lake Valley. The owner wanted responsible renters and was willing to make a decision quickly. 

Later that day we went and looked at the place, and within 24 hours had signed the lease. Just like that everything shifted. We went from hopeless and discouraged, to excited and happy.  

And that’s how quickly change can happen. 

  • You’re alone and wish you had a partner, then you meet someone incredible at a party. 
  • You hate the way your meetings are going then you change the format and it’s like everything is in flow. 
  • You can’t think of anything to write about and then you respond to an email and you get a great idea for a post. (This one is autobiographical and happening right now 😉)

Things can change quickly. 

The question is, are you open to that? 

  • Are you open to the possibility of things changing swiftly? 
  • Are you willing to let things change fast? 
  • Are you ready to be flexible when change presents itself? 

To be a successful leader, creator, or entrepreneur, it’s important to be open to sudden changes and actively seek ways to adapt. If you’re resistant to the possibility of sudden change, you may feel like your problems are insurmountable and your work is constantly challenging.


Is God or the Buddha in the room with you? 

What is it that you want in the room with you when you’re making big choices about your business? 

For many leaders that I coach, the big things they want in the room with them are the right data or knowledge and their own instincts. 

They also love having me as a coach in the room with them because they see me as a sounding board. Someone who’s smart enough to get their ideas, but objective enough to challenge and push their thinking to a new level. 

But what they don’t always realize is that we’re not in the room alone. If I’m in the room, the Buddha is in the room too. Not that I’m the Buddha, far from it, but I try always to bring a bit of that stillness and Zen sensibility into the space with us. 

And I think that’s more vital than most people realize. Yes knowledge in the room, yes instincts, yes some crazy wisdom, but don’t we want God in the room with us? Don’t we want the one bright mind of the Buddha? Or the brilliance of Saraswati?

Our work may be of this world, but your calling is so much deeper. It’s a calling to serve and create something that matters. And even if all you have is a sliver of the divine don’t you want it in the room with you? Don’t you want it sitting with you as you decide which direction to go? 

So how do you do this? 


  • Create some space for silence when you’re making a big choice or contemplating your next move
  • Let go of thinking and sink into your body, feel the energy that flows through you
  • Offer a prayer or ask for guidance as you make a choice, even if you don’t know who or what you’re speaking to
  • Be open to the possibility of guidance from something outside of yourself as you chart your path
  • Imagine a mentor you value in the room with you sitting quietly in the corner listening

Maybe this feels too woo woo or maybe it speaks to something you’ve always felt, but it’s so simple to start bringing it in. And even if all it brings you is a little more peace and clarity of mind, isn’t that alone worth it? 

When you make big choices who do you want in the room with you? 

Think beyond the people in your life to the energy that helps you be as wise as possible. 




What if your best self made choices for your worst self? 

I once did a call with a client where he wanted to talk about signing a prenup. He was getting married again for the 2nd time and felt conflicted. Some people were telling him signing a prenup was a MUST-DO! and others said that signing one would doom his marriage to failure. 

As we explored the question a reframe came into view. 

What if a prenup was just a way to let his best self make choices for his worst self? 

Right now, he and his partner were deeply in love, generous, and open. Hopefully, it would stay that way, but what if one-day things shifted? 

What if the relationship struggled or changed and they fell out of love? 

If that happened they would both be full of grief and maybe even anger and frustration. Would they make the best choice on what was fair as they parted ways? Or would emotion and lawyers take over and turn a painful situation into something even worse? 

By choosing how to separate today from this loving place, they would be prepared should the worse arrive. 

From this perspective he began to see how signing a prenup could be a generous and loving act for both of them. 

Too often we think that planning is about defense or protection. But often knowing how things will fall apart and deciding how we want to handle that in advance can be a powerful practice. 

You can use this thinking to plan for 

  • Business partnerships that go south
  • Hires that don’t work out well
  • Choosing what do to when you’re very tired or worn out
  • Planning for moments of trigger or upset

It’s not that you can plan and sort out everything in advance. It’s simply that you can consider how to allow your best self to choose for a version of you that may not be fully ready for all the feelings and challenges that show up when life gets hard. 


Is This Relationship Serving You?

Relationships make up a big part of our experiences in life, but we rarely really address if a relationship is serving us or not. 

If we hire someone to do a job, we often assess whether or not they are performing up to our expectations. If they don’t we intervene. We offer more training, we communicate our desires more clearly, and we start to track their progress, but we rarely bring this kind of intention and clarity to our relationships. 

Am I satisfied with the depth of this connection? 
Does this relationship feel how I want it to feel? 
What do I even want to get and create in relationship? 

As a result, we tend to hold onto old relationships out of convenience and comfort and fail to invest in new relationships out of a fear of being uncomfortable or an uncertainty about how to deepen our connections. 

So what if we began to look at relationships and consider how we could improve them, deepen them, and create connections that give us the kind of deep satisfaction, challenge, and enjoyment we most crave? 



What’s the difference between an employee and a leader?

What’s the difference between an employee and a leader?

You might say it’s responsibility or scope of work, but very often the biggest difference is mindset. 

An employee thinks about their work as a series of tasks to get done. 

Those tasks are clearly defined and their job is to complete them to the satisfaction of their manager or boss. If something isn’t working they might do their best to fix it, but if it’s outside the scope of their job they might also just tell their boss and wait for a solution to be offered. 

A leader thinks about their work as a vision that needs to get created. 

They think about what they want to happen, they assume it’s possible, and then they work to figure out how to make that happen. They have conversations, invent new ways of doing and thinking, ask tough questions, and overcome obstacles in order to bring their vision into a reality. If something goes wrong they accept and adapt as needed. 

Most of us would prefer to lead teams of leaders. 

And yet so many leaders treat their teams as employees. Leaders want their team to do what they would do. So they direct, control, and limit. Worse still they treat their teams as obstacles that need to get fixed, falling into their own employee mindset. 

The world doesn’t need more workers. We need more leaders. And we need leaders who touch, move, and inspire others to lead. 


The Internet Is Like A Dorito

Have you ever looked up from your phone only to realize that you’ve spent 30 mins researching what causes a rash. Or 40 mins watching short videos that added little else than vague amusement to your life.

The internet is masterful at offering us easy to munch ideas, images, and experiences.

It’s like a Dorito, most of the magic is in the coating. Once that’s gone, you’re left with an inferior corn chip with little texture or nutritional value.

We almost never do this in real life. Spending time walking down a street, noticing the architecture of buildings, spending time chatting with a store clerk.

Real life is harder, it’s 3D, it’s complicated, it’s messy. But the payoff is real.

It’s why spending time in nature is so healing. And why spending hours in the digital forest is so exhausting.

So the next time you notice yourself lost in the woods of pages and ideas, you might try going outside and being with yourself for a change.

It may not be as easy or immediately satisfying, but I guarantee it will change your life.


My Whole Team QUIT! And How To Let Go

I’ve been thinking a lot about the choice to let go of something. Hope, people I care about, how I want things to be…


I recently took Facebook off of my phone and Ipad. I rarely go on to check it, just to post and share.

This didn’t feel that hard to let go. I notice an urge to go back and check it sometimes, but generally I just don’t, it’s that simple. If I can survive the urge I stay with letting go.


Recently my amazing assistant told me she wasn’t happy. At first, I tried to figure out a way to get her to stay but I don’t want someone to work for me if they aren’t happy. So we agreed to give it the weekend.

Over the weekend I stayed up SUPER LATE working really hard out of fear and panic. But I eventually saw what I was doing. I relaxed. I accepted. I let go.

So on Monday when my other assistant said she was quitting too it was fine. I felt some fear and I accepted it. I ended up talking to the last remaining member of my team on Wednesday of that week and we got clear it was time for him to move on as well.

I let them go. I was scared. I was sad. But it just felt like what wanted to happen. I relaxed and let go.


There are a few things in my life I continuously struggle to let go.

The need to try really hard.
Remembering my ex.
Dreaming about my future partner.

All of these feel impossible to let go of. Especially in the moment.

Pushing really hard is easy for me. Life has often felt like a bare knuckle boxing match and I just need to punch my way through.

Over and over I see myself doing this and I let go, but it comes back again and again.
I’ve sort of given up on the idea that this will ever go away completely.

Every time I feel resistance, I feel sadness. Part of me wants to reminisce, part of me wants to let go, part of me wants to feel grief.

Slowly I let go but there’s often pain. Even in the clarity of the path ahead.

Finally I often dream or fantasize about who I might be with next.
Having children.
Making love.
Laughing together.
The simple feeling of peace waking up next to someone.

Again and again, I try to let these go.

These are especially difficult because the fantasies often feel really good.
Sometimes they’re painful because it makes me feel even more lonely now.

But slowly I let them go.


Moment to moment these things seem like they never move at all.
At times I feel overwhelmed and hopeless.

But when I look back I see them slowly shift and melt.

I work less hard than I used to.
I go long stretches without thinking about my ex.
I forget about the fantasies and am just here in my life.

In these moments patience is the hardest thing for me to muster
I want to let go faster.
Which generally has me hold on harder.

But slowly, gently. I am learning to let go.


Devotion vs. Obsession

For a lot of my life, I was devoted to things that I couldn’t help but pay attention to. After college, I dated a girl who wasn’t a good fit for me. My roommates at the time took us canoeing and we fought the entire time. Years later they told me they could always tell how a relationship was going for the people they took on these trips. If they fought the relationship usually wouldn’t last.

Still, I couldn’t let her go. Even when she got engaged to someone else I found myself calling her and having these wistful conversations. I wasn’t good for her and she wasn’t good for me. But I was devoted. The devotion just wasn’t by choice.

If you pay attention to music, books, and music this is the kind of devotion you see a lot of. This feeling of not being able to stop thinking about someone, to stop pursuing some dream, to let go of a hunch. And obsession isn’t always bad. People who are obsessed with science and math have made incredible discoveries, but obsession isn’t the most powerful way to relate to devotion.

This is especially true in our relationships but it’s also true for our work.

No matter what it is, a beautiful partner, an amazing project, or a challenging problem to solve, obsession always runs out. It wanes and trembles in the face of reality.

True devotion is more solid than that. True devotion is a choice you make to give yourself to something, and that means giving all of yourself. Not just the self that always feels like showing up. It means giving the part of yourself that’s grumpy, unsure, full of doubt, and tired. It means offering yourself with all of your imperfections.

True devotion finds a way through obstacles and the ebb of energy.

This is the shift the Buddha made before he became enlightened. For years he was obsessed with waking up. He starved himself, stood on one leg for days, and sat with tremendous physical pain, but when he let go of his obsession and instead brought his devotion to practice everything shifted.

This lesson is one I’m still learning, because for me obsession feels more familiar. It feels easier to lose myself in my desire and passion for someone or for a project. And sometimes I let myself. But I don’t stay there.

As I let go of the emotional intoxication of obsession I either return to devotion or I let it go. Because I’m not really interested in living my life from the standpoint of a victim even if it gives some energy and excitement. What I’m interested in is living my life from the standpoint of a leader and giving my full devotion to those things that are truly worthy.