Curiosity Over Compliance: How to Build a Team That Solves, Not Just Delivers

You don’t scale by getting more done. You scale by solving more of the right problems—before they become fires.

Most operators think output is the path to growth. More calls. More meetings. More tasks completed. But if your team is just executing, they’re missing the point.

Growth comes when your team develops the ability to see around corners. To question the assignment. To ask: What are we really trying to solve?

The Problem: Task Completion Over Strategic Thinking

When a team member asks, “What do you want me to do?”—you’re in the wrong posture.

The best team members ask:

• "What outcome are we aiming for?"

• "What constraint are we trying to remove?"

• "What might we be overlooking?"

Leaders can’t afford to be the only ones solving. You need a team that can think beyond the to-do list.

Case in Point: From Spray & Pray to Strategic GTM

At Signpost, we recently rolled out a Metro Opportunity Index to focus our outbound GTM efforts. Instead of blindly targeting cities, we layered in:

• Population growth

• Permit volume

• Contractor density

• Digital maturity (CPC pressure)

The result? A clear, ranked list of 10 metros that make up our highest-likelihood wins.

This wasn't just a data exercise. It was a shift from delivering "go outbound" to solving for "where and why outbound will succeed."

The team now has confidence, clarity, and a smarter way to execute.

Tool: Train Your Team to Think Like You Do

Give them these 3 prompts:

1. What decision are we enabling?

2. Who depends on this?

3. What might we be missing?

Apply it to any initiative—product, GTM, operations—and you’ll start getting better questions, faster adjustments, and real ownership.

Action Step for the Week

Pick one area where your team is just delivering—not thinking.

• Reframe the problem.

• Give them context.

• Ask them to come back with options, not answers.

Then sit back and watch what happens when curiosity becomes a habit.

Let’s Crowdsource This

What’s one area in your business where your team is stuck doing instead of thinking?

Want my "Curious Team Framework"? Reply with "Team Thinking" and I’ll send you the 5-minute version we use internally