The Questions That Change Everything

When teams or individuals hit a wall, the instinct is to hunt for answers.
But in my experience—advising GTM leaders, coaching sales teams, and working with professionals at career crossroads—the answers usually aren’t the problem. The questions are.

The right question can shift perspective, cut through noise, and create clarity faster than any outside advice. Here are five that I’ve seen unlock progress again and again.

1. What problem are we really trying to solve?

Pipeline is slowing. Deals are stuck. Quota is missed. The obvious reaction is to “fix” the visible issue. But often, that’s just a symptom.
The same is true in careers—chasing the next job, the next certification, or the next title, without pausing to ask what’s truly missing. Naming the real problem changes everything.

2. What would success look like three months from now?

Big goals are important, but they’re hard to act on. Compressing the timeline forces clarity.
For GTM leaders, this might mean identifying one leading indicator that will matter most in the next quarter. For individuals, it might be asking: “How would I know my work felt better by summer?”

3. If I already knew the answer, what would it be?

This ReflectPath favorite works because it bypasses overthinking.
More often than not, people do know the answer—they’ve just buried it under noise, fear, or other people’s expectations. Asking this question makes the instinctive truth harder to ignore.

4. What’s one thing we can remove to make this simpler?

Revenue organizations (and careers) get bloated with initiatives, processes, and “shoulds.” Subtraction is often the fastest path to clarity.
One GTM team I worked with simplified their forecasting process by eliminating duplicate data entry—freeing reps to sell more and managers to coach more. The same principle applies when individuals remove unnecessary obligations or outdated goals.

5. What’s the cost of doing nothing?

Standing still has a price.
For leaders, inaction can mean losing market share, burning out a team, or letting competitors define the category. For individuals, it can mean months—or years—of frustration, stagnation, or missed opportunities. Sometimes, naming the cost of inertia is the nudge that makes change inevitable.

The Takeaway

The best leaders and the most fulfilled professionals aren’t those who collect the most answers—they’re the ones who ask the best questions.

So here’s my challenge to you: pick one of these five questions and actually sit with it this week. Write it down. Ask it in your next team meeting. Or use it as a journal prompt.

The shift you’re looking for may already be waiting on the other side.

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