A few years into doing this work, I’ve realized something simple:

My best work always happens with people who want a very collaborative or transformative partnership. People who want pushback, context, honesty, directness, and clarity -- but they also want compassion, empathy, and kindness. 

They want someone they can relate to, but who maybe has more (or different) experience, or more years notched on the belt. 

This isn’t new. It’s how I’ve always led. It’s why I still hear from people I managed ten years ago. We had shared goals. If they wanted to get promoted, I wanted them promoted. If they needed a tough conversation, I gave it to them. If they were stuck, I got in the trenches with them.

The deeper I go into advisory work, the clearer this becomes.

Some relationships compound. Others don’t.

Here’s a simple framework for telling the difference.

This is very necessary but also shallow by nature. It’s efficient, but also, forgettable. 

Transactional relationships are the entry point for most interactions, especially in business. You hire a designer, a consultant, a growth marketer. You pay an invoice. You get a deliverable. Clean, simple, emotion-free.

A Level 1 relationship is a vending machine full of great snacks. Useful. Reliable. Get you where you going. Maybe not the most depth.

And zero massive outcomes.

This level is trickier because it feels better than Level 1 - a bit more warm. Some camaraderie involved. A holiday card? Sure, why the hell not. 

Adam Grant calls this the “likability illusion,” where many leaders mistake friendliness for effectiveness. You can be adored and still be mediocre. Worse: people can like you so much that they avoid telling you what you need to hear.

This level can be especially challenging because you’re not transactional, but not yet Level 3, either. 

I once had an investor ask me if I was worried “the team didn’t like me” at that particular moment. I laughed. No, I wasn’t worried - they respected me, and that’s all that mattered. 

Most leaders spend their whole careers thinking Level 2 is the promised land.

It’s not though. 

Level 2 is necessary for trust, but it doesn’t create breakthroughs. You don’t build $100M companies or strong leadership teams off of just vibes.

This is where the real relationships really begins.

Level 3 relationships are about comfort, and trust, sure, but they’re also about creation. About solving real problems together. It’s about having a historical context, background on ambitions, fears, goals; and being in it together in a way that truly feels like a team. 

In level 3, you can disagree without it becoming a massive deal. You’re rowing in the same direction, at the same cadence, for the same reason.

This is the level Pixar co-founder Ed Catmull writes about when he describes the Braintrust, a sacred, no-ego table where peers tell one another the truth because the work matters more than anyone’s feelings. 

It’s about two things: expertise, and empathy. 

This is where I always want to live with my clients.

Their goals are my goals; their urgency is mine; their failures resonate in a deeper way. 

We have radical honestly, and none of the drama. 

When a CEO hires me, I’m not there to pontificate, I’m there to help them build, fix, improve, expand.

Level 3 is the operating system for that work.

This is obviously much more rare, but, it’s the the ceiling for true leadership impact.

Level 4 relationships can alter your trajectory, force you upward, confront your blindspots, demand something better, and in return, they impact you, too.  

Think of people like Bill Campbell, the man who could coach Steve Jobs, Sergey and Larry, and an entire generation of Silicon Valley greats because his relationships were rooted in deep trust and shared purpose. 

Campbell wasn’t playing at Level 1. Or 2. Or even 3. He lived almost exclusively in Level 4.

Farnam Street describes this as the zone where “relationships produce compounded returns.”

This level requires:

This is the level where the right advisor or mentor can unlock entire seasons of growth for anyone - a direct report, a peer, a friend, a founder - not because the person is some magical hero or something, but because the relationship is.

Level 4 takes time. 

Because Level 3 and 4 relationships require both people to show up fully, I am trying, personally, to be as selective as possible about who I work with. 

If someone wants a transactional advisor, there are thousands of people who will do that. And occasionally, I like doing ‘quick’ Level 1 or 2 work - you get to learn about new people, new companies, new things. It can serve a short purpose. 

But for the most part, I get more excited about the long-run, helping people build and push and investing in their business together. I also think that’s where I’m at my best. 

I’ve led teams this way my whole career. I coach this way. I advise this way.

And the CEOs who get the most from me are the ones who want to operate here too.

Whether you’re an advisor or you’re a startup founder or a manager at a big org, if you want to build something that really lasts, and that’s truly meaningful, you can’t live in Levels 1 and 2 alone. 

Sure, they’re safe, polite, easy, fast. 

But, I really do believe that Level 3 and 4 are where the most meaningful relationships live, and where you find the most personal satisfaction.

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