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.


High integrity vs High expertise

Are you looking for integrity or expertise? 

If you’re trying to hire someone on a tight budget or in a competitive market you’re going to end up with a lot of candidates that fall into one of two categories:

  1. High expertise / low integrity – These people know a lot about the subject you need help with, but they aren’t very reliable. Either they have a long turnaround time, some character flaws or their work is uneven. 
  2. High integrity / low expertise – These people are hard workers, they strive to meet deadlines, and will be honest, but often they don’t know a lot about the job you need done. 

Choosing between these people can be super challenging because you really want both. You want someone who knows a lot and is reliable, but very often these people are is short supply or very expensive to hire. 

So If you can’t have both which one do you choose? 

In most cases, the best answer is to hire the High integrity low expertise person. The reason is simple. Knowledge can be learned but integrity is hard to change. Some people will get better with the right incentives or the right coaching but people with character flaws and challenges are often reluctant to change. 

But high integrity people, people who do what they say they’re going to do, those people are pretty amazing. Because they can use that integrity to learn, grow, and become better. 

The only place where you should choose a high expertise low integrity person is when either:

  1. The role demands expertise and it demands it now
  2. You only need them for their expertise and not their execution

For example, let’s say you need someone to give you feedback on your speech. Working with a skilled speaker will make your speech much better, but if the only person you can find to help is a little flaky that’s ok. Make sure you figure out a fast and simple way to get their feedback and give yourself enough time that they can cancel or delay. 

You can do something similar with programming. If you need really good code written it might be better to hire someone like them to start the code (create the framework) and then hire someone else to finish it in their style. 

Again this isn’t ideal but often if you think and strategize you can limit or compress your need for expertise instead of doing what I see a lot of people do, which is hire brilliant people and then try to wrangle and deal with their difficult personalities. 

I know it may take longer, but generally, it will still be faster and less stressful if you limit your exposure to low-integrity people and only rely on them when you absolutely need to. 

It’s a simple lesson, but one that I’ve seen a lot of founders and entrepreneurs have to make again and again.


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? 



The Temptation to Overuse New Strengths

Maybe we want to develop more patience. Maybe we want to be less judgmental. Whatever it is, we have a specific thing in mind that we want to improve, one of our weaknesses that we want to become our strengths.

It starts as an altruistic spiritual pursuit, and then as we become more aware of how to change it, we launch wholeheartedly into the process. 

Once out on the other side–once we’ve done the work to develop this skill, ability, capacity, or trait–something interesting happens. We develop a sense of pride in our new power. Our change feels like a hard-won victory and as a result, we can begin to overuse this new way of being.

The signs of this happening are often hard to notice. They are much more subtle than our original wake up call. But it’s important to be able to recognize this in ourselves, so we don’t let the pendulum swing too far in the other direction and thus begin to create a new set of problems when we change.


Are Your Strengths Destroying You?

Nobody is perfect; we all have ways in which we want and need to grow, or to improve our strengths. However, these desires aren’t always at the forefront of our brains. Sometimes we don’t even recognize the areas where growth is most needed until something drastic forces us to look at them.

We often realize where our weaknesses are in moments of vulnerability. For example, after a person we care about leaves, or when we get difficult feedback, or when a project we are working on falls apart. 

When these moments hit, we may suddenly realize that something about ourselves needs to shift, that our strengths need improving.

The breakdown or crisis that leads to this moment of clarity is usually so deep and powerful that it’s impossible to ignore. Thus, it compels our system into action towards growth. 

So, we set off on our personal improvement journey. 

And it works at least for a while . . .


Why older men want to date women half their age?

When an older man dates a younger woman, he steps into a time machine. He feels like he still has youth and vigor.

He trades the problems of aging, of a certain stage of life, for younger problems. It allows him to avoid the truth that his life has moved on or should have moved on from concerns and hopes and excitements he had or skipped over years before.

​​But this doesn’t just happen with younger women. This happens with new ideas. Fast cars. Extravagant vacations. New companies. And all sorts of other things.

It is a truly self possessed leader who chooses to be where he is. Who chooses to be with the problems of this stage of life. Who deals with the old problems, the ones that are really challenging and rises to the cause.

There are no time machines. And even though you may be able to step into a younger relationship or stage through the power of money or mind doesn’t mean your life will be richer for it.