Why We Built the Planning Power Quiz (and What It Can Tell You About Your Business)
Over the past few years, we kept noticing the same thing in our conversations with business owners: almost everyone knew they needed a stronger planning rhythm, but very few actually knew what kind of help they needed next. Some thought they were “behind,” when really they were just in the early stage. Others thought they needed a brand-new system, when what they actually needed was a small refinement to one they already had.
What we realized is:
Planning maturity has stages… but most leaders don’t know which stage they’re in.
And when you don’t know your stage, it’s easy to either:
expect too much, too fast (and burn out), or
stay too small, too long (and stall out), or
repeat cycles that keep you from getting traction
So we built the Planning Power Quiz to give leaders clarity before commitment. Instead of guessing where the breakdown is, you can quickly see what kind of planning structure your business is actually ready for.
The four stages the quiz measures
Pathfinder
You haven’t really had a planning rhythm before, or if you’ve tried it, it never fully took shape. The business is now at a size or pace where instinct isn’t enough anymore, and you’re realizing that structure would give you relief, clarity, and direction.
Builder
You’ve done some planning — maybe even a few annual plans or offsites — but you’ve struggled to keep the plan alive throughout the quarter. The issue isn’t belief in planning, it’s confidence. You’ve seen it fade before, and you’re trying to rebuild trust in the process.
Optimizer
You already have a planning system in place (EOS, Scaling Up, OKRs, etc.), and it works… but you know there’s another level of impact you haven’t reached yet. You’re looking for stronger alignment, deeper accountability, and more results from the rhythm you’ve built.
Strategist
Your planning discipline is strong. The next questions aren’t about running the current year — they’re about the horizon: second-level leadership, succession, valuation, or exit readiness. You’re no longer just guiding the business — you’re preparing it for the future.
Why take the quiz?
Because the planning stage you’re in determines the planning support you actually need.
Pathfinders need a gentle, confidence-building start.
Builders need structure that sticks through the quarter.
Optimizers need more value from the system they already use.
Strategists need altitude — not another checklist.
The wrong approach at the wrong stage creates friction. The right approach at the right stage creates momentum.
This quiz is a simple way to figure out what stage you’re operating in — so your next step in planning is the one that actually fits where your business is today.
