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. 




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. 




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.


What you aren’t listening to? 

It is very likely that the people around you are saying something you’re not listening to. They are telling you what’s wrong with your leadership. They are telling you what you don’t want to hear. They are telling you what they want more of from you. 

But you aren’t hearing it. 

You aren’t hearing it because you are sure it isn’t true. 

Or if it is true it’s not your fault. 

Or if it is your fault it’s not your fault that it’s your fault. 

I see this in almost every single client I’ve worked with. 

Start up founders ESPECIALLY!!!!!

They love to talk about the reality distortion fields of Jobs, Musk, and Bezos. 

They don’t love to talk about the reality filters they all have. 

The filters that hide what could make them even better leaders and people. 

If you want to hear what you’re not listening to start here:

  1. Whatever the most common complaint people have about you, where are they right? Where could you show up more in that space? What’s missing? 
  2. What feedback do you dismiss, deflect, defend, or dissect regularly? Reflect on it and you’ll very likely find something there. 
  3. Find a quiet morning and ask yourself. What am I avoiding hearing? Write down anything that comes up. 
  4. Ask people, What have you been saying that I haven’t been hearing? What have you tried to tell me repeatedly that just doesn’t seem to be getting through? 

You don’t have to keep not listening. You can hear. You can become more. It won’t mean losing your power, it will mean becoming more powerful. 


Hope is not leadership

If you run a startup you are familiar with the language of hope. You sell it to investors, you pitch it to your team, you whisper it to yourself at night to help you sleep when things aren’t going very well. 

Hope is a powerful. It can help you generate a lot of interest in what you’re creating. 

But hope is not leadership. 

Hiring someone and hoping they will do a great job is not the same as supporting them to do a great job. It’s not the same as inspiring them and getting the best work out of them. 

Starting a project and hoping it will get completed on time and with excellence isn’t the same as planning it well, giving it the resources it needs, indetifying the pitfalls and blocks and moving them out of the way. 

Hoping you’ll get enough sleep, or that work will ease up, or that your relationship will get better is not the same as creating time to rest and recover, getting clear on what you should and shouldn’t be doing, and being really present with the people you love. 

Hope is a powerful companion to leadership but you, your team, your company, your investors, your dreams, and your vision need more than hope. They need you to be a leader in a world where it’s much easier to act like a leader than actually show up as one. 


4 questions to ask when someone is upset

When someone in your life is upset a partner, a team member, or a coworker it can be hard to know how to handle it. There might be a desire to fix or solve the problem that caused the upset. You might feel defensive or scared based on their emotional state. You might even want to avoid the person or situation entirely hoping it will resolve itself. But few of these responses create the space to hear someone who’s upset or get to a place of repair that will help you and them move forward. 

So here are the steps I try to follow when I’m being with someone who is upset. 

1) Do I have space for this and do I want to hold space for this? 

Just because someone is upset doesn’t mean you HAVE to make them feel better, try and fix their problem, or even be upset too. 

You might feel a natural sense of empathy or a desire to help the person who is upset. But even if this is your initial impulse it helps to check in and see how you’re doing. If you’ve got space and want to hear or help the person go for it. But it’s also totally ok if you don’t have space. 

You can lovingly start by saying, “I’m really sorry you’re upset right now, I don’t have the space right now to hold you in your upset.” 

Then you can offer to be with them at a later time OR you can simply decline to hold space. 

You might say, “I’d be happy to talk to you about this once I’m off of work.” 

Or “I’d be happy to talk to you about this once you’ve calmed down a bit.” 

Or “I hope you can find someone else to talk to about this.”

Or “I hope you can find someone else to talk to about this, but if you can’t you can check in with me later.”

This kind of loving boundary might be hard for people to hear, but it’s better than trying to be there for someone when you simply don’t have the space. 

2) Is this about me? 

When someone is upset about someone or something there can be an instinct to either try to calm them down or fix what’s wrong, which is why it’s first important to discern if the upset is about you. 

If someone is upset about someone else or something that’s happening in their lives it’s very likely they just want to express themselves and be heard. They may want a solution at some point but only after they’ve cleared out some emotional space. 

If the upset isn’t about you, the best space to start is to just listen to them and reflect on what you’ve heard. This is also true if it’s about you, but because it’s so easy to make other people’s upset about you I think this is an excellent place to start. 

If it’s about you, you can hold space and reflect on what you hear while trying not to get defensive or combative. If it isn’t about you, don’t make it about you. Let them be upset. It might be hard, but as much as possible don’t try to fix them or their problem. Remember it’s not even about you. They just need a space to be upset. 

3) It’s about me, now what do I do? 

If it’s about you, the best thing to do is to start by hearing the other person. It’s possible they’re going to say things you disagree with, feel unfair to you, or that you think are wrong or upsetting. While it’s important you don’t let someone verbally abuse you, short of that you’re going to be better off if you can avoid taking things personally and just listen to the person. 

Take a deep breath and see if you can simply listen to what they are saying and from time to time reflect back to them what you’ve heard. 

This is KEY! Just because you’re reflecting back to someone what they heard, doesn’t mean you’re agreeing with them, or that you’re saying what they are thinking is true. 

The first need most people have when they are upset is to be heard and to have their feelings validated. Even if what they think you said or did isn’t what you said or did, it’s often better to just honor them and their feelings. 

Whether or not you agree with what they thought happened their feelings are real, so simply reflect what you’re hearing as closely as you can. 

“So when I showed up at 9:05 you were upset because you thought I was late and you hate having to wait on me.”

“So when I went to class without you, you were mad because you felt like I didn’t care if you were with me or not.”

Bonus points if you can tell them their feelings made sense. Remembering that someone’s feelings can make sense based on what they experienced even if what they experienced was different from what you thought or experienced. 

4) What do I have to apologize for or own here? 

The final question to ask yourself is what do you have to apologize for or own. It’s very likely that if someone is upset with you, something you did play a part in it. You may not have intended to hurt them, to say something unkind, or to do something they didn’t like. But your intentions only matter in part, what ultimately matters is your impact on people, so if you can apologize for the impact you had on them or any mistake you made. 

“I’m sorry I was late and didn’t text you. I was trying to text you and it didn’t go through, but that doesn’t really matter, what matters is that you felt dropped by me.”

Bonus points if you add what you’ll shift next time and thank them for sharing themselves with you. 

“Next time I’ll pause as soon as I know I’m going to be late and send you a message. Thanks for helping me better”


You need time apart

No matter who it is. Your romantic partner, your business partner, your work wife, your closest friends, or even your kids you need time apart. And this can be hard. You get into a groove, a routine, a rhythm, and you don’t want to step away. 

The thing you need space from might be a person, an activity, even a way of thinking. But no matter the category all grooves become ruts without time away from them. 

So take a moment to reflect on your life and see what you’re stuck on or with. And consider taking some space. For 30 mins, for a day, or even a week. Usually when you return you come back with greater appreciation, love, and a deeper understanding of what does and doesn’t work for you about that relationship, task, or way of life.