How to Run a Quarterly Planning Workshop

By Kevin Brent · 4 March 2026

Every 90 days, your business needs a reset. Not a vague “let’s think about next quarter” conversation over coffee, but a structured half-day session that reviews where you have been and sets clear priorities for where you are going.

Here is how to run one properly.

Before the Session

Preparation makes the difference between a productive planning day and a talking shop. In The Entrepreneurial ScaleUp System, Kevin Brent recommends:

• Complete an InFlight Check — a diagnostic scorecard covering your four pillars (Strategy, People, Execution, Cash). Score each area 1 to 5. This highlights where the gaps are before you start planning.
• Gather your data — last quarter’s Critical Number (did you hit it?), rock completion rates, financial performance, customer feedback.
• Block half a day — morning works best. Get out of the office if you can. Remove the temptation to “just pop back for a quick call.”

Part 1: Review the Last 90 Days (60 minutes)

Start by looking back before you look forward:

1. Critical Number review — did you achieve the one metric that defined success last quarter? Why or why not?
2. Rock review — go round the table. Each person shares which rocks they completed, which are in progress and which they dropped. No judgement — just honest reporting.
3. Stop, Start, Continue — this simple exercise surfaces what to stop doing (things not working or preventing something else), what to start (things not being done that should be), and what to continue (things working well or showing promise).
4. Key learnings — what did you learn about your customers, your market, or your team this quarter?

Part 2: Set the Next 90 Days (90 minutes)

Now look forward:

1. Check alignment with your longer-term plan — do your 1-year critical paths and 3-year base camp still hold? Any external changes to factor in?
2. Set the Critical Number — the ONE metric that will define success for this quarter. “The business needs to achieve x as measured by...”
3. Define business priorities — no more than 7, typically 5. These are the initiatives that will drive the Critical Number.
4. Create a Theme — make the quarter’s priority engaging for the whole team. Something memorable that people can rally around.
5. Set individual rocks — each person identifies their 3 to 5 rocks for the quarter, linked to business priorities. Format: “I will achieve x as measured by y.”
6. Define SMART actions — break each rock into specific, measurable steps with deadlines.

Part 3: Commit and Close (30 minutes)

1. Share rocks publicly — each person states their rocks to the group. Public commitment increases follow-through.
2. Confirm the weekly rhythm — when is the Smart7 meeting? Who facilitates? Is the daily check-in agreed?
3. Set the next planning date — book it now, 90 days from today.

The Smart7 Weekly Meeting

The quarterly plan only works if you review it weekly. The Smart7 is a 60-minute agenda that keeps the rhythm alive:

1. What went well? (30 seconds each)
2. What did not go well? (30 seconds each)
3. Progress against rocks — on track or off track (30 seconds each)
4. Customer and employee feedback (10 minutes)
5. Focused work on off-track rocks or issues (30 minutes)
6. Actions — What, Who, When (5 minutes)
7. Key takeaways and priorities for the week (1 minute each)

Getting Started

If you have never run a quarterly planning session, the G90 Summit is a guided half-day virtual workshop that walks you through the entire process. You will leave with your Critical Number, business priorities and individual rocks set for the quarter.

Once you have your plan, Smart90 gives you the daily and weekly tools to execute it — check-ins, rock tracking and the Smart7 meeting format all built in.