Why? They want a promo code
Why? They think your price is too high
Why? We didn't do market research
Why? We're understaffed
Why? I haven't filled the position
Magic, right?
Well, almost.
7/ The 6th Why
Do you notice what happens as we move through the Whys?
💡 They get specific -> We progress from what happened to what caused it.
💡 And more personal -> Groups narrow to individuals.
There's one more Why & it's uncomfortable.
But that's where the growth is.
8/ Back to our example
Why haven't you filled the position?
❌ Maybe you designed an unattractive role
❌ Perhaps you didn't see the demand coming
❌ Or you are losing people faster than you can hire
These answers are raw & imply something about YOU is causing the issue.
9/ This isn't just about work
I can't get in shape
Why? No time to workout
Why? Day is packed with work
Why? My boss keeps piling on more
Why? B/c I haven't told her no
Why? B/c I can't disappoint her
Why? B/c I need the money
Wait, it's a money issue not a fitness problem?
10/ Now what?
Don't overreact to one mistake. We all make them.
Do watch for patterns of mistakes. These tend to reveal true weaknesses.
Every CEO I coach asks me some version of the same question.
"How do I find A-players who make sh!t happen?"
At Bridgewater, I ran hundreds of interviews looking for this exact thing. We called it "acting like an owner." Others call it high agency. Here are 5 tests to find it:
Test #1: The Conviction Test
Have they taken a contrarian stance that was later proven correct?
If No... you're hiring someone who requires direction and waits for consensus.
The best people see something before everyone else agrees it's true. And they act on it anyway.
Test #2: The (Un)popularity Contest
Have they walked away from something safe for something risky?
If No... they've never actually bet on themselves. And it's not just belief. It requires moving past others' disbelief.
You want someone who's survived feeling alone before.
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.
2. High skill, low risk: get out of the way.
Give the outcome and a deadline, then leave. Checking in here isn't diligence. It's you telling your best people you don't trust what you already know they can do.
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.
Test #2: The Surprise Test
How often does your boss learn bad news about your team from someone other than you?
If it's happening at all, you won't have their trust.
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.
2. Setting expectations, new way:
Paste in the JD, last two reviews, and team OKRs into AI. 'Draft 5 outcomes this person owns this quarter and the 3 behaviors that produce them.'
You're making final edits in 5 minutes, and the doc lands cleanly. You still own the final call.
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.
Problem 2: Clear Communication
The tell: Your ideas get restated by someone else and land better.
The fix: Lead with the answer. Pyramid Principle in one line: answer first, three reasons, evidence under each.
If the "so what?" isn't obvious to an outsider, it's not ready.
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.
2. Coveted Coach
Your impact multiplies when you develop others.
- Spot strengths people don't see in themselves
- Connect development to real work
- Encourage good mistakes
Great leaders don't create followers.
They create more leaders.