New Team. New Boss. The #1 Success Factor.

5 Questions to Align With Your Boss

Imagine this.

You’re in your first 90 days managing a new team. You’re sitting in a one-on-one with your boss, walking them through an update you feel great about. You and your team have been working hard. You’ve been putting in long hours. You’ve made what feels like real progress.

And your boss responds with something like, “Okay… but that’s not really what I was looking for.”

What a terrible feeling.

Because in that moment, you realize something important. You’re not just behind. You’ve been working on the wrong thing.

And if you’re managing a new team right now, this matters more than almost anything else. The number one success factor in your role is not your leadership style. It’s not your years of technical experience. It’s not whether you inherited a strong team or one that needs a lot of help.

It’s alignment with your new boss.

This is one of the most common challenges I hear from tech industry managers.

They feel like they’re doing everything they’re supposed to do. They’re working hard. They’re trying to support their team. They’re making decisions, moving things forward, staying busy.

But there’s this underlying tension. Feedback from their boss feels unclear. Priorities seem to shift. Expectations don’t quite line up with the work that’s getting done.

And over time, that creates friction. Not because the manager isn’t capable. Not because the team isn’t working hard. But because there’s a lack of clarity from above.

Alignment doesn’t happen automatically. You have to proactively take the steps to make it happen. 

So here’s what you’re going to do. You are going to set up a deliberate, dedicated alignment conversation with your new boss. Thirty minutes if you can get it. The goal is to walk out of that conversation with a shared picture of reality and a shared view of what winning looks like.

There are five topics you want to cover in that conversation.

• First, the situation. How does your boss see the current state of the business and your team? What challenges, pressures, or opportunities are top of mind right now?

• Second, expectations. What specific outcomes will define success in the next 90 days and beyond?

• Third, style. How do they prefer to communicate and make decisions? Do they prefer frequent updates via Slack, or hold everything till your next 1:1? Which decisions are you empowered to make and which need to be escalated? 

• Fourth, resources. What support is available to you and your team? Budget, headcount, executive sponsorship. And just as important, where are the constraints? Any headwinds or landmines you need to know about? 

• Fifth, early wins. Which outcomes would build credibility and show momentum fastest, both for your boss and for the team?

When you have clarity across those five areas, everything changes. Your decisions get easier. Your priorities stabilize. Your team stops spinning. And your work starts to land the way you expect it to.

You’re no longer guessing. You’re aligned.

And once you have clarity, don’t hoard this information. Share what you’ve learned with your team. Translate it into simple, repeatable language so they understand what matters, how success will be judged, and how their work connects to the larger mission.

Final thought, don’t think of this as a one-and-done event. Priorities change. Even style can change. Regularly check back in with your boss on these critical topics to make sure you are still aligned. 

Remember, when you’re leading a new team and you’ve got a new boss, this is the most important single factor in determining your success or failure in the role. 

You got this. I’m rooting for you!

Best,

Jeff

P.S. If you’re a tech industry manager who has recently taken on a new team, I built something you might want to check out. It’s a free 5-day email course called: The 5 Mistakes Tech Managers Make When Taking on New Teams.

I’m wishing you the best. Reply to this email and let me know how it’s going in the new role. I love hearing from you!