A few years ago, when I was leading a team through a particularly chaotic product period, I developed a habit I was genuinely proud of: I gave my managers everything. Every upstream signal, every exec conversation, every bit of company context I had access to. I told myself it was respect — treating them as partners, not just executors. And honestly, at the time, I believed that.
It took one of my managers sitting across from me and saying, almost apologetically, “I find it hard to make a call now without first talking to you” — for me to realise I had built something I didn’t intend to.
I had built dependency.
The instinct to share context isn’t wrong. It comes from a real place: you’ve watched leaders who hoarded information and created confusion, you’ve seen teams make bad calls because they didn’t know enough, so you overcompensate in the other direction. That’s a reasonable response to a real problem. The issue is when context-sharing becomes a substitute for trusting your team to reason through ambiguity — and when your managers start waiting for the full picture before they act.
In large orgs, the full picture never arrives. There’s always more context you could share. Another stakeholder conversation. Another upstream dependency. Another thing the VP mentioned in passing. If you’ve trained your team to expect completeness before deciding, you’ve inadvertently trained them to be slow, and to route everything back to you.
What I was doing — and I say this with some discomfort — was being generous in a way that was actually about my own need to feel useful and in control. If my managers had context, they’d make the right calls. If they made the right calls, I could feel like I’d done my job. The flaw in that thinking is obvious in retrospect: I was solving for the decision, not for the decision-maker.
Here’s what I noticed once I started paying attention. When I pre-loaded a situation with context, my managers would take what I gave them and solve for the exact parameters I’d laid out. They stopped interrogating assumptions. They stopped asking “wait, why is that constraint actually a constraint?” They trusted my framing because I was the one with the information — and that trust, while flattering, was the problem.
The managers who grow fastest are the ones who develop a nose for uncertainty. They get comfortable making a 70% call with the information available, communicating the assumptions clearly, and adjusting when new data arrives. That muscle only develops through practice — and it only gets practice if you let them operate in incomplete information.
What I started doing instead was reversing the flow. Rather than briefing my managers before they came to me, I started asking: what do you know, what do you think, and what would you do if you couldn’t reach me? Nine times out of ten, they had a reasonable answer. The tenth time revealed a genuine gap worth addressing — not with more context, but with coaching on how to reason through it.
There’s a real difference between giving someone information they need to do their job and briefing them so thoroughly that you’ve pre-solved the problem. The first is leadership. The second is subtle micromanagement wearing a generous face.
None of this means you stop communicating. Your managers still need to understand the direction you’re headed, the things that are genuinely fixed constraints versus the things that are open, and where the org is placing its bets. That’s not context-overload — that’s table stakes. The line I try to hold now is: share the what and the why at a strategic level, and let them figure out the how without a playbook from me.
The other shift — and this one is harder — is getting comfortable when your managers make a call you wouldn’t have made, and it turns out fine. That happens more than you’d expect once you stop front-loading everything. And when it does, the right move is not to say “here’s what I would have done” — the right move is to say nothing and let the confidence build.
Your job isn’t to be the smartest person in every room your managers walk into. Your job is to build managers who don’t need you in the room at all.