For years I delegated by gut. "Can I trust them with this?" If yes, hands off. If no, hover close. Both were wrong. I smothered good people and abandoned people who needed help. Trust wasn't the right lens. Here how to get your oversight right: 1. Score the work on two things:

How capable is the person at getting it right?
How risky is the work if it goes wrong?

Vary your distance by your confidence and the consequences.

An executive I worked with got fired unexpectedly. The signs that he wasn't trusted were there for months. No matter what I did, he didn't want to see them. "If only I'd really listened to you."

Here are the 4 tests he was failing: Test #1: The Front Foot Test

Is your boss asking you for updates?

If Yes...you're being reactive.

Trusted managers answer the questions before they're asked. Better yet, they answer the questions their boss should be asking.

Confidence conveys competence.

I've trained 1500+ managers. Two skills make or break them: setting expectations and holding people accountable. But both take hours to get right, so they rationalize skipping them. AI removes the friction, not the conversation. Here's the old way vs the new way: 1. Setting expectations, old way:

90 minutes drafting a role scorecard, sent Friday, read Monday. By Wednesday you're aligned on 60% and "circling back" on the rest.

It felt like a good start. But it created three weeks of clarifying meetings instead of actual clarity.

You need to develop more "executive presence." Well-intentioned feedback that's utterly useless. The problem: It's the visible symptom not the deeper cause. If someone tells you this, your first job is to figure out which of these five things they actually mean... Problem 1: Quality of Thinking

The tell: People leave your meetings with worse questions than they arrived with.

The fix: Write your calls down. Grade them quarterly. Figure out where your judgment is strong and where it's lacking.

Nothing teaches like unfiltered data.

You are not rewarded for hard work. You are rewarded for being hard to replace. Outcomes, not effort. True for every employee. Even more acute for managers. Here are 7 skills that make a manager irreplaceable: 1. Relentlessly Resourceful

Constraints stop average performers but inspire exceptional ones.

- Generate options for every obstacle
- Build a cross-functional solution network
- Document your wins to reinforce the mindset

Teams never let go of people who find a way forward.

The last thing I wanted to do every Friday was send my team an update. I knew it was important and the highest leverage way to keep the team connected. But doing it well took a ton of effort. Now AI writes a script I edit and record in 10 minutes. Here's my 5-step system: Step 1: Dump the raw week.

Paste your notes, wins, losses, updated numbers and shipped work. Don't organize it. Don't filter it. That's AI's job.

Bonus: use connectors and let AI do the data-gathering.

Successful leaders rely on two things: judgment and courage. Judgment to separate big from small. Important from unimportant. And the courage to apply that judgment. To maintain high standards. To defend their team's focus. Anyone can build both. Start here: Give them CLARITY

Vision: everyone knows where we're going and why it matters

Roles: crystal clear who does what, owns what, decides what

Standards: non-negotiable behaviors and quality expectations

It was 10pm. I was alone in my office. My whole team had gone home hours ago. Not because the work was done. Because they were waiting on me. That's when it hit me: I wasn't the expert saving the team. I was the bottleneck. Here are 4 tests to find out if you are too: Test #1: The Inbox Test

How many requests are sitting with you?
How long have they been there?

More than a handful?
More than a day?

That's not a busy manager.
That's a team stuck on you.

I've hired hundreds of people. My worst hires didn't fail on skill. They failed on things I could have caught in the interview. Here are 5 hiring mistakes that cost me the most (and how I catch them now): 1. Hiring for the job, not their judgment.

A great resume tells you what they did. It says nothing about how they think. Ask them to walk through a real decision, messy middle and all.

"What got you here won't get you there." It's cliche, but it's true. The best individual contributors often make the worst first-time managers. I was one of them. Here are 5 things I had to quickly unlearn: 1. You don't have all the answers.

As an IC, knowing got you praised. It made you valuable and impactful.

As a manager, jumping in with the answer just trains your team to wait for you. You build yourself into the team's bottleneck.

Seek to understand before you direct.

The fastest way to accelerate your career:

Work exclusively with exceptional managers.

Here are 7 questions to ask when you're interviewing them: 1. Who have you recently promoted (and Why)?

What I'm listening for:
- Are promotions merit-based?
- Can they get people promoted?

Anyone who survived more than 10 minutes at Bridgewater was excellent at taking feedback. It was daily. It was public. It was all recorded in a system. It overwhelmed a lot of talented people. Here's the system I used to make the most of 11,358 pieces of feedback: Step 1 - Welcome it.

Your first job is to make it safe to tell you the truth. If you deflect, argue, or explain, you teach people to stop.

The most dangerous place to lead from is a spot where nobody is willing to tell you the truth.

When someone gets fired for not being a culture fit, it usually means one thing is missing: high agency. They crave direction. The require permission. They might meet your expectations, but they'll never beat them. Here are 4 ways I screen for people who act like owners: 1. The pronoun test.

Ask about a past win. Listen for 'I' vs 'we' vs 'they.' High-agency people own the mess: I noticed, I pushed, I figured it out. Low-agency people narrate: the project happened, then it shipped.

How they think = How they speak

I've trained 1500+ managers. They all struggle with delegation. The issue isn't assigning work. It's ensuring the work gets done well without micromanaging. Here's a simple 5-step system for helping your team succeed: 1. Create Clarity

Establish 5 parameters upfront:

• Outcome: What success looks like
• Quality: What signals done
• Method: Agree on how the work gets done
• Timeline: Set clear milestones and deadlines
• Risk: The boundaries for autonomy

When I was an MD, our CEO killed a new product launch. My team asked me to fight. I made a pitch instead. 9 months later we acquired a competitor 10x bigger. Knowing when to push back is one of the hardest leadership skills. Most never do it. Or do it wrong. Here are my 4 tests: Test #1: The Asymmetric Info Test

Do you have data that would change your boss's mind?

If No... you don't have reason to pushback.
You have a preference.

Your job is to surface what they don't know.

Not just to disagree to disagree.

There is no recipe for becoming a great leader.
But this checklist will get you close: CLARITY

🔳Vision: everyone knows where we're going and why it matters

🔳Roles: crystal clear who does what, owns what, decides what

🔳Standards: non-negotiable behaviors and quality expectations

95% of work problems are caused by one thing: unclear expectations. The manager is frustrated. The employee is confused. Everyone's stuck. Here's my simple playbook you can run to get (and stay) on the same page in 15 minutes: If you're the manager:

Setting expectations is your primary job. If your team doesn't know what you expect, you're failing them. And despite great effort, chances are they're letting you down.

The vicious cycle of frustration builds.

I used to think setting goals for my team was just picking targets. Numbers. Deadlines. Milestones. Then I learned the target matters less than the right mix of goals. Choose poorly and your team's excellent work is wasted. Here are the 3 kinds of goals that actually move teams: 1. Run Goals

These keep the lights on. Ship the release. Hit the quota. Close the tickets.

Teams need them. They're not always inspiring, but they're your Why.

But ff you only set Run goals, you factory is falling behind. And your best people will get bored and leave.

Good intentions don't make great leaders.

Your target week: 10% strategy, 25% talent, 65% ops. Your reality: 2% strategy, 8% talent, 90% ops.

Too many leaders let ops crowd out everything. Here's my ideal leadership week, and how I make it a reality: 10% on strategy.

This is NOT "think strategically" when there's time.

It's scheduled. Blocked. Protected. No phone. Where is the market heading? What's changing? Where do we win?

Realty is coming fast these days. Make the space to see it and adjust.

The leaders I work with are drowning. Too many 1:1s. Too many memos. Too many decisions they're not ready for. I used to be one of them. Then I built a second brain. Now I prep in minutes, not hours. Here are 5 painful parts of managing that got 10x easier: 1. Prepping for 1:1s.

Used to take me 15 minutes per report, if I bothered. Now my AI Chief of Staff reviews last week's transcript, the project status, and the patterns from the last 3 months.

I walk in with a V1 agenda in 90 seconds. My reports actually feel supported.

Senior execs have Chiefs of Staff. Founders have EAs. Partners have associates. Managers have nothing. That's why you're drowning. Last month I built myself one using Claude Cowork. Here are 3 ways an AI Chief of Staff changed how I lead: 1. It skips years of trial-and-error.

Most managers learn by doing. 8 years of bad 1:1s to find a format. 40 memos to find your voice.

Your AI Chief of Staff starts with proven playbooks on day one. EOS Rocks? SBI feedback? Amazon 6-pager?

Your V1 is most managers' V10.