7 Strategic Questions Your Team Should Be Able to Answer

How to Help Your Team Think More Strategically With 7 Strategic Questions

I’ve never met a leader who said, “My team is just too strategic. I wish they’d focus more on the TPS reports and less on big-picture thinking.” Nope. More often, it’s the opposite:

“How do I get my team to think more strategically?”

Followed by:
“Karin, I can’t get promoted until I find a successor, but no one on my team seems ready to step up.”

And the classic, “These Gen Zs just don’t seem to care about the long game.”

Before you write off your team’s strategic potential, take a moment to reflect. Are they not strategic—or have they never been invited to think that way?

If you’re only giving your team a peek at the finished puzzle, it’s no wonder they can’t see how the pieces fit. Strategy isn’t a big reveal moment. It’s a conversation.

Let’s dive into how you can open up that conversation and teach your team to connect the dots—even the ones they can’t yet see.

Why Your Team Might Not Be Thinking Strategically (Yet)

It’s tough to think long-term when all you see is today’s fire drill. Strategic thinking requires context, clarity, and—most importantly—access. If your team is busy grinding out tasks without understanding how they ladder up to something meaningful, they won’t magically become strategic thinkers. They’ll stay really efficient executors.

Also worth noting: if you always wait until your ideas are fully baked before looping them in, your team never learns how to be bakers. They’re just the icing squad.

7 Strategic Questions Every Team Member Should Be Able to Answer

If you’re looking for a way to gently nudge your team toward strategic thinking, start with these questions. Think of them as your GPS: Guiding People Strategically.

1. Why do we do what we do?

And no, “to make money” doesn’t count. Dig deeper. What problem are we solving? For whom? Why does it matter?

Want to spark a discussion? Ask your team this question during your next meeting. Don’t be surprised if there’s a long pause—this one hits deeper than it looks.

2. How does our work contribute to the bigger picture?

When your team can connect their daily efforts to the organization’s mission, motivation skyrockets. Bonus: they’ll stop chasing shiny objects that don’t align.

See Also: How to Stay Focused at Work and Avoid the Rabbit Hole

3. What do our customers really want?

Your team knows. You know they know. So ask them. Then double-check: are your processes, policies, and priorities aligned with those customer needs?

4. Who are our major competitors and what makes us different?

This question can reveal a lot—not just about the market, but about what your team thinks makes you special. That’s important strategic data right there.

5. How does the way we work impact other teams?

Spoiler alert: if your process creates a bottleneck downstream, your coworkers aren’t just annoyed—they’re probably building workarounds. Strategic teams consider the ripple effect.

6. How can we better communicate with the teams we rely on?

This one often leads to a gold mine of “Why didn’t we do this sooner?” moments. Make a wishlist. Then build a bridge.

7. What’s the most important thing we’re working on—and why?

This question surfaces hidden priorities and disconnects. If your team’s answers vary wildly, it’s time for a realignment conversation. (Gently.)

BONUS STRATEGIC MOVE: Dig Into the “How”

In the SynergyStack habit “Investigate How Things Work”, we encourage people to relentlessly ask “Why?” Not just for the sake of curiosity—but to truly understand the mechanisms behind your operations.

Here’s how to help your team peel back the “how” layer:

• Ask them to explain a process backwards. Reverse-engineering forces people to think beyond muscle memory.

• Encourage them to challenge assumptions. “Why do we do it this way?” is not insubordination. It’s innovation trying to be born.

• Assign curiosity homework. Have one team member each week present a 5-minute “How It Works” spotlight—whether it’s a system, a report, or even your invoicing flow.

This level of exploration helps your team go from doing the work to understanding the work. And when they understand the work, they’re more equipped to improve it. That’s strategy in action.

Be the Baker, Not the Icer

Helping your team think more strategically isn’t about handing them a binder full of buzzwords. It’s about opening up your thinking, asking better questions, and creating safe spaces for ideas to breathe.

Invite them into the strategy. Let them mess with the dough a little. You might just discover they’re more ready than you thought.

Want to go even further?

Help them ask:

• What problem is this solving?

• Who is affected and how?

• What could we do differently if we had 10% more budget? Or 10% less?

And if that doesn’t work? Well, you can always start with, “Tell me more.” That G.O.A.T. Powerful Phrase works wonders.

Related Articles:

Byeon Magical Thinking: How to Ensure Your Team “Gets It”

No More Bad Reports: how to Get Your Team to Bring You More Useful Information

Your turn. What would you add as strategic question number 8?