Bootstrapped Giants

McKinsey & Co's secret for building million dollar teams

Published 3 months ago • 7 min read

At 22, I landed my dream job.

Business Analyst at McKinsey & Company. I was told there is no better place to start your career out of college and I was stoked. Within 6 months, I got staffed on a HUGE project.

The largest (at the time) private equity deal in HISTORY: KKR was buying Bell Canada for $45 BILLION.

I got my assignment and was hopping on a flight to Toronto, immediately.

There were 12 total team members and we had 6 weeks to diligence this business for a sophisticated and demanding client.

It was fast paced and intense...but it was also something I didn’t expect: fun.

And beyond fun, it was a life bonding experience where I still can text and call my teammates from that project 17 years later!

While most people in startup circles poo poo McKinsey and consulting, you have to respect how they hire newbie undergrads + MBAs and within months turn them into teams F500 CEOs are willing to pay MILLIONS for.

Think about it: they're pulling together small teams of SUPER bright, capable people to work on a HUGE problem in a SHORT period of time with an expectation of HIGH QUALITY work.

Oh, and by the way, these people are OFTEN working with each other for the FIRST TIME.

That sounds…well, exactly like a startup!

The key is they focus on the most important 5 letter word in business: TRUST.

If you’re like me, your first reaction may be to roll your eyes and get back to your spreadsheets.

But humor me. We’ve all seen the teams that seem to have fun, give each other candid feedback and jump to help each other. We’ve also seen teams that blame each other, stare at the train crashing and trash talk each other.

So I would argue TEAMWORK is more important than the PLAN. And TRUST is the key ingredient.

So what are my steps to building trust? Here’s how I approach it.

This is actually where most leaders are stuck. Jesse, I’ve got a million things going on. I have to hire, fire, look at reports, close clients. And you want me to make time for TRUST?

Whether you like it or not, you have a certain amount of trust with each person you work with and they have a certain amount of trust with you. Now I’m not talking about trust like: if I turn my back, will they steal my wallet. That’s a pretty low bar. That’s a 5/10. I’m talking about do they believe you have their back? You’re there to support? Or does a team member simply feel like they're a cog in your machine? Again, whether you make time for it or not, it's there.

To start making time and naming it, I like the “trust battery” analogy. Between any two people is a battery. Every interaction either charges up the battery or uses a charge. If you never charge the battery, there’s very little charge you can use from it. Once there’s no more charge, the relationship likely won’t work.

Anytime you’re moving fast, working on high stakes NEED trust to succeed.

Some ways to charge up your trust:

  • Open yourself up by sharing personal and professional news. Going first will encourage everyone else to open up too.
  • Come out and say it explicitly: "I want you to know I trust you."
  • Send texts to share what's going on in your life and check in on people. It lets them know you care and that they're in your inner circle.

If they trust you, they say yes and go the extra mile. If they don’t, they feel the need to protect themselves...which makes it hard to work well.

The best part about step 1 is just making time to talk about it 1x1 and in a team setting and naming it...BUILDS TRUST. When you name what’s going on in peoples’ minds anyway, they immediately trust you as a more capable leader.

A user guide explains YOU as the product. What are your preferences, how do you like to communicate, what are your development areas (err weaknesses), what are your strengths?

Mine includes:

  • I like texting people when I have ideas. I used to stress everyone out. Until I told people, "I want to text you, but you are not obligated to respond." Win win.
  • I am very numbery. If you put numbers in front of me I will dig in. That doesn’t mean I’m being critical or don’t trust you, it's just how I learn/understand.
  • I communicate in fragments and haiku sometimes, if something isn't clear don’t be afraid to ask
  • Over communicate - I have NEVER once in my career told someone they are communicating too much. Err on the side of 2-3x the communication you think is reasonable.

You can read my full User Guide here.

This article by First Round is the best one I’ve come across on how you should write yours: The Indispensable Document for the Modern Manager

The value should be obvious: instead of taking 6-12 months for someone to decipher these things about me...they learn them IMMEDIATELY. And that builds trust!

As a bonus, ask your team to write their own for you to read. Watch your speed and fun SOAR!

For most of my first few years of CEOing, I asked people to trust me with their concerns or deep dark secrets. Nobody did and I was always frustrated. Then one day my head of HR said: “You never share any of your own secrets or challenges, why would anyone share with you?” Now I routinely say things like, "I don't know how to grow this part of the business," and my team says things like, "I feel distracted today because my wife and I got into a fight."

There’s a reason I said to write your own user guide first. In conversations, team meetings and everything else: start by sharing first. Not just what you did over the weekend. Share what you’re excited about but even more important: share what scares you. Share your growth areas.

Normalize a level of vulnerability that makes you slightly uncomfortable. Not nauseous, but butterflies in your stomach.

As you do that, start asking my favorite question: “What is the one thing you are most afraid to tell me?

With the right foundation, your team will share and rapidly build trust (assuming you listen and acknowledge vs defend).

Get everyone together!

Zoom if you must, but ideally in person, in the same room. You can share your plan, goals, initiatives etc of course. That’s valuable. But the real value is in steps 5 and 6 and simply the natural bonding that takes place in between. This is even more critical in a post-covid era where hybrid/remote work is the norm.

But make time every quarter to get everyone together, for at least 1 day. Reply to this email if you want offsite agendas I’ve done for Gateway X companies!

This is so valuable, I was originally going to write the whole email on this part alone.

The team learning is something I stole straight from McKinsey. It's one of the big answers to how they form small teams who work together quickly, on high impact projects.

Get the whole team together in a room. Have an open and explicit conversation about workstyle preferences.

Example questions are:

  • Are you a morning or evening person? (I am NOT a morning person)
  • What are 1-2 areas you wish to grow in the next few months?
  • How well do you understand this problem?
  • What is your Enneagram or MBTI type? (I love these.)
  • How do you like feedback? Real time? Or batched?

There are two extremely powerful benefits to the team learning:

1) Everyone learns a TON about each other in a very short period of time. Like the user guide, in 1 hour you can learn things that would take you months of working together to glean.


2) and most importantly: You normalize talking about the “HOW” around work. You make it okay to say out loud: “I prefer we don’t schedule meetings at 6pm, I work out then” or “I didn’t love how that feedback came across.”

This sets the foundation for more intimate, high trust teams.

Here is the format for the Team Learning.

Then going forward, I’d recommend regularly discussing the “HOW” of teamwork is going. Engineers have been doing this forever with “agile” sprints. They talk plenty about the work, but they also do a “retro,” looking back on how the team worked together and could improve on the next sprint.

I think every other week is the right cadence.

My coach Dave Kashen curated a ton of great bonding games, which I put in this doc: Team Building Exercises

What he taught me is: Play, Touch and Vulnerability is what creates team bonding and intimacy.

These may seem corny but my favorite games are:

1) “If you really knew me…”

End the sentence with something personal...could be “I ate pizza for lunch”, could also be “I’m scared about my new assignment.

Everyone chooses their own level of vulnerability. Then go deeper with “if you really really knew me..” Then 2-3 more rounds, going deeper with each one! You’ll be amazed at what people share and how you feel afterwards.

2) Personal histories

I like to write up a handful of questions at different levels of depth and have the team go around and ask them over dinner.

How many siblings do you have? And “What's a difficult experience that shaped you?” are examples, let other people ask them and go around and answer.

3) Ways of being

Have the group form two lines, facing each other.

Each side says to the person facing them, "What I’m curious about you is…" "What I appreciate about you is…" and "What I want for you is…"

So there you have it.

You may have the best strategy and plan in the world roaring into the year.

But it won’t matter if the team doesn’t execute it. Trust and Teamwork are the secret to amazing execution.

And most startup leaders are underinvesting in it...Change that today!


Bootstrapped Giants

Jesse Pujji

Bootstrapped to an 8 figure exit @ampush. Now building a $1B+ bootstrapped venture studio @GatewayX and sharing everything I learn along the way.

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