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Get Unstuck

Living in the question: How intentional decision-making and strategic thinking lead to better answers

Anne Machesky

Not every question is asking for an immediate answer.

We live in a culture that rewards speed. As leaders, we’re expected to make decisions quickly, keep things moving and reduce uncertainty for everyone around us. Over time, that expectation can create pressure to have an answer before we’ve fully understood the situation.

That’s often the moment we start to feel stuck. The pressure to move forward is there, but the right answer isn’t obvious. So we reach for the first workable solution.

In doing that, we often settle on an answer before the problem has fully taken shape. What gets lost is the ability for the situation to develop more dimensions before we define it. That’s often where early certainty becomes a constraint.

Breaking that loop requires a specific kind of reflective skill: actively living in the question.

What does it mean to live in the question?

Living in the question is the practice of not collapsing meaning too quickly. It asks for enough space between the challenge and our response so that something more accurate has room to emerge.

In leadership environments, the pattern is familiar. When a problem surfaces, our default instinct is to rush straight into timelines and execution. It feels disciplined and efficient. But when the definition of the problem hasn’t caught up to the speed of the response, what looks like momentum eventually becomes repetition.

The more we slow down, the more we actually speed up. It’s less about patience than it is about accuracy.

How do you practice living in the question?

In my work with executives and teams, I encourage them to anchor their introspection by asking two baseline questions:

  • What is present? This brings attention back to what is actually in front of us — the objective facts and pressures — rather than our interpretation of it.
  • What needs to be? This shifts attention forward to the actual outcome required, creating space to define direction before action takes shape.

How do I make space for that insight and alignment?

The way people create space for living in the question is rarely the same. For some, it’s taking a walk. For others, it’s stepping away from a screen. The form doesn’t matter as much as the internal pivot it creates when our attention is no longer locked on the problem. That break in focus allows our thinking to reset.

When the shift happens, the problem doesn’t disappear. It becomes more dimensional. We start to see what’s shaping our response to it, not just the surface issue in front of us.

That’s often where something more personal shows up. The situation may connect back to experience or an expectation in a way that wasn’t obvious at the start. Once that connection is visible, the problem is no longer interpreted the same way. That realignment ultimately changes the quality of our thinking, and new options begin to surface.

The next time there’s pressure to answer quickly, stay with it a little longer. Keep the question open for business. Sometimes the answer isn’t delayed. It arrives once there is finally enough room for it to be seen.

In practice

  • Resist the urge to answer before the problem is fully understood.
  • Ask yourself to define what is present and what needs to be.
  • Keep the question open for business long enough for more than one possibility to emerge.
  • Remember, your goal is not to delay, but to achieve better alignment between urgency and understanding.
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