When was the last time you asked: “Is this still the right problem to solve?”

Many change efforts stall not because of bad execution, but because no one asked if the context had shifted.

Context-Setting Agility is the leadership skill that helps teams move with purpose, not just momentum.

Years ago, I was co-leading an initiative with a tight deadline, high visibility, and a ton of moving parts. On the surface, everything was going really well. You know the situation, right?

The team was executing hard:

  • Daily stand-ups, Sprints on track, Metrics looking solid
  • Timeline: on track, Deliverables: on point, Team: engaged

And yet… something felt off.

Stakeholders were getting quieter. Mid-level leaders were disengaging. And I was starting to feel that gnawing “we’re missing something” sensation. I kept hearing a quiet disconnect in conversations: “I’m not sure how this ties into where we’re going...” “This is solid work, but does it solve the real problem?” “Feels like we’re just checking boxes.”

I brushed it off at first and told myself, “Just push through. We’ve got a plan.”

But then a team member said to me: “I know we’re moving fast, but… are we still solving the right problem?” That stopped me cold. Because the honest answer? I wasn’t sure.

The project was succeeding… but not progressing. So we paused. Stepped back.

What I saw shocked me. In our eagerness to execute the plan, we had stopped questioning the context in which the plan was made. And that context had shifted, quietly but significantly.

We had been so focused on delivery that we hadn’t stepped back to reassess the context. Customer expectations had shifted. Leadership priorities had changed. And we were still chasing the original brief.

That was the moment I fully understood what Context-Setting Agility really means. It’s the leadership capacity to:

  • Zoom out before you zoom in.
  • Reframe your priorities
  • Realign your team as the ground moves beneath you
  • The courage to question your assumptions, even mid-flight.
  • And the humility to say: “Maybe we need to reframe.”

It’s not about being indecisive. It’s about being adaptive without losing direction.

After that realization, we gathered key voices, re-examined assumptions, and reframed our core goal. The shift wasn’t dramatic on the outside. But on the inside?

  • Clarity returned
  • Energy came back
  • The work had meaning again

Because now, we were solving the right problem in the right way.

Since then, I’ve made regular reflection part of how I lead and coach others. Even simple questions will initiate a good discussion and lead toward the right goal(s).

  • Why are we doing this right now?
  • Are we solving the right problem?
  • What’s changed since we made this plan?
  • How might we need to reset our direction?

Because strategy isn’t one-and-done. It’s a living conversation.

Have you ever realized you were executing the wrong plan, just a little too well?

Let’s normalize stepping back, not just stepping up.

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