Three Questions that Reshaped Our Leadership Meetings

Borrowed

“The skill of the coach is the art of questioning. Asking incisive questions forces people to think, to discover, to search.”

From “Execution: The Discipline of Getting Things Done” by Larry Bossidy, Ram Charan, and Charles Burck [Book]

Learned

Some months ago, I decided to revisit the agenda for my weekly leadership meeting, or “Pulse,” just before kicking off a new weekly Growth team meeting. Pulse has been a Wednesday ritual for years, but I introduced Growth meetings after establishing lead roles across new business, partnerships, and marketing.

Given the different groups, each meeting serves its own purpose but follows a tight agenda, covering topics such as new business progress, financial performance, team resourcing, weekly outreach, and the health of our client engagements.

During Pulse, I often noticed that the most timely, critical discussions seemed to happen by chance. We had an “issues” list meant to capture what needed attention, but we didn’t always fill it out, and even when we did, we sometimes ran out of time to address it.

My goal was to create a more intentional space for reflection. A way to prompt everyone to think about how they were contributing each week, what might be getting in the way, and how we could work together to remove blockers and keep things moving forward.

In August, I introduced two questions to both meetings:

What’s something you led or pushed forward this week that helped the team or business make progress?

• Could be a decision made, a project unblocked, a new insight, or a win for the team.

What’s a blocker or setback you ran into this week? What’s the next step to turn it around?

• Could be a misalignment, a delay, something that caused confusion, or a missed opportunity.

The team embraced these questions immediately. Everyone appreciated how the meeting maintained a clear structure while leaving a designated room for open and honest conversation.

These questions have since surfaced all kinds of challenges and opportunities across the agency (that may have gone unnoticed in the past). Everything, from process improvements to concerns about an individual’s performance and early signs of complex client dynamics.

All in all, they’ve opened up some fruitful, sometimes intense, discussions and have helped the leadership team stay aligned, celebrate wins, and hone in on important topics every week.

A couple of weeks ago, I decided to add a third question:

What do I know I should be doing but not doing?

• What might happen if I keep avoiding it?
• If I had just one day to move it forward, how would I start?

My intention by asking this was to encourage everyone to think more creatively about what they might be putting off and why. Sometimes it’s a tough conversation that needs to happen. Other times, it’s a big project that requires breaking down into smaller steps.

So far, it’s been interesting to see how answering this question has inspired small team brainstorms. While I tend to guide the discussion, it’s fun to see others jump in to help unpack it. It feels a bit like a coaching session. My hope is it helps each person move something forward, even if it’s only 1% further than they were the week before.

What I’ve also loved about this question is how it brings together short-term and long-term thinking. The short term often feels the most urgent and is where progress is easiest to see. It’s satisfying to check things off and know something moved forward. However, that doesn’t make the long-term impact any less critical. The long term shapes where we’re going and whether our short-term efforts actually matter. This question helps bridge the two by creating a pause to reflect on what’s right in front of us while keeping sight of what will matter most over time.

Some weeks, the answers to all of these questions take over the agenda; I’ve learned to see that as a positive sign. It usually means we’ve uncovered a meaty topic or an unresolved issue, and it deserves the time and attention. While having an agenda keeps us on track, the goal isn’t to mindlessly rush through it, but to create a space where the conversation moves the work forward.

I plan to keep experimenting with this. The questions will likely evolve, but my focus is always on continued learning, curiosity, and creating space for conversations that move us closer to where we want to be.

Thought

Where might adding a question be more effective than adding another agenda item?