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The Three Questions That Matter for 2026

Business planning season is here. Again.

Leadership teams often approach it with a mix of optimism and dread—optimism about what’s possible, dread about the three-hour meetings that produce 47-slide decks nobody follows.

Here’s a better way: three questions that force the hard decisions your company actually needs to make.

The Start-Stop-Keep Framework

Before your planning session, ask every leadership team member to answer three deceptively simple questions:

1. What should we START doing?
These are opportunities you’re missing. New capabilities, initiatives, or approaches that could move the needle but aren’t happening yet.

2. What should we STOP doing?
Programs, processes, or activities draining time and money without real return. This is where courage matters—stopping feels risky, but it frees capacity for what actually works.

3. What should we KEEP doing?
What’s working that you need to protect, double down on, or replicate across the organization.

Why This Works

This framework forces clarity. It’s hard to hide behind vague aspirations when you have to name specific starts and stops. Your CFO can’t just say “improve efficiency”—they have to identify what stops to make that happen.

The magic happens when you compile responses before the meeting. Suddenly patterns emerge:

• Four people independently say “stop the weekly status meeting”

• Three leaders identify the same opportunity you’re ignoring

• Everyone agrees on protecting customer on-boarding, but nobody’s resourcing it properly

You get alignment before the debate even starts.

Strategic Planning Applications

Use Start-Stop-Keep to examine:

• Strategy: Market positioning, competitive moves, growth initiatives

• Operations: Processes eating bandwidth, automation opportunities

• People: Hiring priorities, development programs, team structure

• Products: Feature development, sunset decisions, support levels

• Customers: Segments to pursue or exit, relationship investments

The questions work at every level. Your leadership team completes them for the company. Department heads do them for their functions. You can even cascade it to key contributors.

The Prep That Matters

Here’s the best way to run it:

1. Send the three questions two weeks before your planning session

2. Ask for specific, actionable answers (not vague wishes)

3. Have someone compile responses with duplicates consolidated

4. Share the compiled list a few days before the meeting

5. Use it as your planning agenda—the patterns tell you where to focus

6. Download the Start-Stop-Keep Framework here. It’s free.

What You’ll Discover

Two things will surprise you:

First, your team sees opportunities and problems you’ve missed. The VP of Operations knows exactly what’s broken. Your sales leader has been watching a market shift for months. Start-Stop-Keep surfaces this hidden knowledge.

Second, you’ll find more agreement than you expected. When five people independently identify the same stop, the decision becomes obvious. Political debates give way to shared reality.

The Hard Part

Stops are where most teams fail. Starting feels productive. Keeping feels safe. Stopping feels like admitting failure.

But your capacity is finite. Every minute spent on what doesn’t work is a minute stolen from what does. The companies that win in 2026 will be the ones brave enough to stop what’s not working—even if it worked last year.

Here’s My Take

As you head into planning season, try this: What would happen if you only had time for three strategic stops this year? Not five. Not ten. Three.

Which activities are consuming resources without delivering results? What would you eliminate if you had to choose?

Start there. The rest gets easier.

If you’re planning for 2026, The Execution Canvas can help you translate your strategy into clear, actionable choices that your team can actually execute.