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ARTICLE / Leadership & Teams

Greg Cleary: How Do You Turn 70 Problems Into 5 Priorities?

By Martin Piskoric · 2026-11-13 · 3 min read
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Greg Cleary, guest on episode 558

A leadership team in Dallas–Fort Worth put about 70 Post-it notes on the wall. Greg Cleary had asked them to write down everything that was getting in the way of growth. They had plenty of answers. What interested me was the question he asked next. Which of these notes belonged together?

Let the team sort the notes

Greg calls the exercise “the brutal facts.” He let the team group the notes before he named the categories. Comments about missing skills landed together. So did complaints about inconsistent processes. A group of notes about strategy raised a different question. Could the team explain why a customer would choose them?

Greg uses five headings for what emerged on that wall. People asks whether the right person is doing the work. Purpose asks where the business is going and why. Playbooks capture how to do repeatable work. Performance asks how well people deliver it. Profit gives the team feedback on what its choices are worth in the market.

How much detail belongs in a playbook?

Greg brings an unusual handout to these discussions. It’s a two-page checklist for a Boeing 737. One item reminds the crew to pressurize the cabin. The pilot already knows how to do that. The value of the line is that a trained person sees it at the moment it matters.

That example gives a founder a way to test a recurring complaint. Think of the last time a customer handoff went wrong. Could a trained colleague see, at a glance, what had to happen before the handoff was complete? If three people missed the same step on different days, one well-placed reminder might address three notes on the wall.

Find the gap behind the job title

Greg described a company promoting its best salesperson to sales manager while the leadership team still lacked someone who understood marketing. A promotion can look like a staffing problem solved. Asking who will actually do the missing work brings the gap back into view.

Try the exercise at your next leadership meeting. Give everyone a pad of notes and ask what keeps going wrong. Let them group the answers in their own words. Then choose one cluster and ask the people closest to it what change would make several of those notes disappear. That’s the decision I’d want to take out of the room.

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Greg Cleary shares the experience behind these ideas.

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By Martin Piskoric. Originally published on 21ce.biz.

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