5 Questions That Reveal If Your Strategy Is Working | Ep 209
whatshot 7 snips
Jan 29, 2026
Quick-fire questions that expose whether a strategy is real or just talk. How to pinpoint the single constraint slowing growth. Why narrowing to two or three initiatives matters. Simple checks on gross margin, ROIC, and free cash flow. A fast way to compare team answers and spot misalignment and hidden cash leaks.
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volunteer_activism ADVICE
Focus On One Strategic Constraint
Ask your team: what is the single biggest constraint blocking growth and the 2–3 initiatives you're focusing on to fix it.
Align initiatives to that strategic problem and avoid working on easy distractions that don't solve the constraint.
question_answer ANECDOTE
Offsite That Missed The Point
Steve recounts a strategic offsite where a leadership team spent five days and avoided the revenue constraint entirely.
The example shows how teams distract themselves with easier topics instead of fixing the core problem.
volunteer_activism ADVICE
Make Everyone Recall Gross Margin
Know your gross margin (revenue minus cost of goods sold) for the last 12 months and have your team estimate it off the top of their head.
Use this to test whether people actually track and understand the core financial levers of the business.
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Most business owners are confident their strategy is solid. Then they get asked a few simple questions and everything gets uncomfortable.
In this episode, Steve shares five questions that quickly expose whether your strategy is actually working or just sounds good in meetings. These questions reveal where teams are misaligned, where money is leaking, and why results often stall even when everyone is working hard.
If your business feels busy but progress feels slower than it should, this episode will make that clear fast.
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Strategy Meets Finance