Every Friday, I’m answering one real question from a real leader. No theory. No fluff. Just the stuff you’re actually dealing with.

If you’ve got a question you’d like me to tackle, just hit reply. I read every one.

William, I felt this one.

That phrase, “think more strategically,” is one of the laziest pieces of feedback in corporate America.

It sounds important. It sounds like they’re coaching you. But most of the time, they can’t even define what they mean by it.

And you’re right, it is a catch-22. You need strategic experience to get promoted. But you can’t get strategic experience without being promoted.

I know the feeling. Personally.

I spent 16 years at an engineering firm. I’m not an engineer.

My boss, a division president, saw something in me. He promoted me twice in 2 years. Mentored me. Gave me opportunities I hadn’t earned on paper but delivered on every time.

Then one day he got a call from his boss.

“Justin is not an engineer. We need engineers in that role.”

Just like that, it was over. Even though I was exceeding every goal they’d set. Even though the results were right there on the board.

Didn’t matter. I was out.

I seriously thought about leaving the company. The kind of thinking where you’re drafting resignation letters in your head at 2am.

But I didn’t leave. I took on a less prestigious role. One that could’ve been a dead end.

And I gave it everything I had.

I used the frustration as fuel. I lost weight. Got in shape. Sharpened my skills. Built relationships outside my comfort zone with influential people.

A year later, the person who replaced me left the company.

Guess who got the call.

But that’s not even the real win. The way I handled that setback, the discipline, the relationships, the refusal to shrink… it opened doors I didn’t even know existed. Within a few years, I was in the C-Suite.

William, the room you want into? Sometimes the fastest way in is to become so undeniable they come find you.

But you can’t just wait. You have to play the game with intention.

"Think more strategically" really means: stop talking about tasks and start talking about outcomes. Connect your work to what leadership actually cares about.

I created a cheat sheet on managing up that covers this in detail. But here are the actions that matter most for someone in your position.

This is the A in my ALIGN framework: Anticipate. Understand their priorities, pressures, and KPIs. When you speak their language, you sound strategic instantly. Because you’re connecting your work to their problems.

Every Friday, send your boss a short update with 5 things:

This is strategic communication. You’re not asking for permission. You’re showing that you see the bigger picture. Most senior managers never do this. That’s your edge.

When you raise an issue, come with 2-3 options. Your boss wants to know you can think through tradeoffs. That’s what “strategic” looks like in practice.

Prep them before big meetings. Give them the data, the context, the talking points. When they succeed because of you, your name comes up in rooms you’re not in yet. That’s how the door opens.

Flag problems early. Even before you have the solution ready. Leaders hate being blindsided. The person who gives them advance warning? That’s the person they trust. And trust is how you get into the room.

William, nobody is going to tap you on the shoulder and say “okay, now you’re allowed to be strategic.”

You have to start acting like you already belong at that level. Not with arrogance. With preparation. Perspective. And the discipline to connect every conversation to what matters most.

The catch-22 is real. But it breaks the moment you stop waiting for an invitation and start showing up like you don’t need one.

That’s what got me to the C-Suite. Not a title. Not permission. Just a decision to show up differently. Especially when nobody was watching.

Keep leading forward,
Justin