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Are You Learning to Lead The Hard Way?

There are two ways to learn:

  1. Painful trial and error.

  2. Borrowing someone else’s hard earned wisdom.

The problem with the second way if that you still have to implement the lessons. That takes time and effort. And most leaders are already overstretched.

What if there was a third way? To build a system that learns alongside you. That knows you people and your numbers. That can listen in on every meeting you don’t attend. That applies that lessons you learned in training for you, so you can focus on doing what it can’t: making calls, applying judgment, and leading people.

AI makes it possible. If you set it up to be Your MGMT Second Brain.

Join our 3-hour workshop on July 15th to build yours. See why 1,500+ leaders have said our programs are worth 25x what they paid.

I was on a call last week with a leader who'd just taken over a large, complicated business.

New city. New team. New stakeholders.

Inherited staff. Inherited goals. Inherited culture.

The company’s performance is solid, but his mandate is to make it even better.

As he examined all aspects of this business, he kept circling back to the same question, the same question that keeps most leaders up at night:

"Do I have the right people?"

I’ll tell you what I told him:

It's the wrong question. Or at least, it's not the first question.

There are three others you need to answer. And getting them right makes the impossible question about your people possible to finally answer.

Level 1: What Culture Are You Actually Building?

Before you assess anyone, you need to answer a question most leaders skip entirely:

What kind of team are you trying to build?

What are the non-negotiable behaviors you believe give your team an outsized chance of winning?

Netflix famously said: adequate performance gets generous severance. Professional sports team, not a family. Only keep people you'd fight to keep.

Being clear about this will attract the right people and repel the wrong ones. It will also inform what type of system you want to build to support people who operate this way.

Most organizations don't want to operate like Netflix. And that's fine. But you need your version.

  • Are you building a high-accountability, high-care culture where people are expected to own their area and grow into it?

  • A collaborative culture where the team's output matters more than individual brilliance?

  • A culture where effort and alignment matter as much as raw capability?

There's no right answer. But there's your answer. And without it, every people decision you make is arbitrary.

Two questions to get there:

  1. Would you pass over a qualified candidate who didn't fit this culture?

  2. Would you let go of a top performer who actively undermined it?

If the answer to both is yes, you've found your non-negotiables.

If not, keep going until you do.

Level 2: Design the Team You Need

Now put the people out of your mind entirely.

If you had a blank org chart and were building this team from scratch to win, what would it look like? What boxes exist? What does each one own? What does winning look like in each seat? How do they fit together?

Most leaders skip this step because they constrain their thinking to the existing roles and existing people.

That's backwards. Literally. That approach optimizes for the past.

Design first. Assess second. If you design around your current people, you'll rationalize the wrong structure to protect the wrong people.

In the call with my client, we worked through his team box by box. Unsurprisingly, most of them still made sense. Operations. Research. HR. Accounting. Marketing.

Halfway through, he realized he had couple of hybrid roles that no longer served the company at their scale. And as you might expect, the people filling these roles we’re struggling to deliver valuable work.

That's a design problem, not a people problem.

Training, developing or even replacing the people in a poorly designed role won’t fix the issue. If you can’t make a case for how that role can deliver 3-5x what it costs to fill it, you should question if it’s even a real job.

It’s probably not.

Level 3: People vs. Design

Now you can assess the people. Put the people you have into your target design.

Don’t ask: "Are they good?" This is too general.
Ask: “Are they the right fit for the system you're trying to run?”

For each person in each seat, you have three possible outcomes:

Strong fit. They're proven capable of doing the job you need in the culture you're building. Invest in them. Develop them. Give them more.

Developmental fit. They're close but not there yet. The gap is closeable in a reasonable timeframe. And they want to close it. Reset expectations, give them the resources, set a clear timeline. Three to six months to see meaningful movement.

Not a fit. The gap is too wide, the timeline is too long, or the culture fit isn't there. Or the hardest yet: they don’t have the will to operate in the design you’re building. The move is to develop them out or replace them. Neither is easy. Both are necessary.

Be precise. One category per person. One plan per category.

It may take you months (or even years) to go from the current state to the target design. That’s ok. What’s important is that you know what you’re building and you’re bringing along your stakeholders on that journey.

Level 4: Bring Your Stakeholders Along

You've defined the culture. You've designed the team. You've assessed the people.

Now you have to bring the people who care about the outcome along with you.

Your CEO. Your board. Your key stakeholders. They have opinions. They've known some of these people for years. They'll resist changes they don't understand and support the changes they helped shape.

Your job isn't to ask for permission. It's to bring them along on the journey.

  • Here's the culture I'm building and why.

  • Here's the design I've chosen and what it optimizes for.

  • Here's where we are against that design.

  • Here's the plan and the timeline.

Ten minutes. Clear. Confident. No surprises.

The leaders who skip this step spend months reacting to stakeholder anxiety instead of building the team. The ones who do it early get the room they need to make the moves they need to make.

The Bottom Line

"Do I have the right people?" is the critical question.

But it’s not a question that can be answered on it’s own.

The first is: what culture am I building?
The second is: what design sets us up to win?
The third is: who fits that design, who's developing into it, and who needs to go?
The fourth is: have I brought my key stakeholders along?

Answer them in order. The people decisions get easier every time.

The best coaches in the world don't assess players before they've chosen the system.

Neither should you.

Lead on,
Dave & Mar

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