Strategic thinking & vision
For: Anyone whose work shapes where their team or company is going
"Strategic" is the most-claimed and least-tested manager attribute. A 10-question check on whether you actually see the bigger picture, communicate where things are going, and choose what to skip.
- 10 questions
- 3 dimensions
- ~3-4 min
- Self · Peer · Both
Strategic thinking is one of the most over-claimed leadership attributes — and the gap between claim and reality is huge. The actual signal isn't whether you can talk about strategy in big meetings; it's whether the people around you can articulate where you're going, whether your daily decisions reflect it, and whether you're honest about what you're not chasing. This template surfaces all three. 10 questions across three dimensions, calibrated for the receiving side because strategic clarity is something the audience experiences, not something the strategist can grade themselves.
How it works
Run it on yourself first — try to articulate your own strategic direction in 1-2 sentences. Then send it to the people who depend on that direction: direct reports, peers, your manager. The most useful gap is whether they can repeat your strategy back in a form you'd recognise as correct.
What's inside — 10 questions across 3 dimensions
Seeing the bigger picture
whether you step back from immediate work, notice external change, and connect dots others miss
Communicating direction
whether your strategic message is clear, consistent, and connected to daily decisions
Trade-offs
whether you say no to good things that don't fit, and whether you're honest about what's being given up
The questions, in full
Every question is included below. You answer them yourself first, then send the same set to the people who've seen you work.
Seeing the bigger picture
- Q1Rating (1-5)
This person can step back from immediate work and ask whether we're solving the right problem.
- Q2Rating (1-5)
When something changes externally — market, customer, competitor — this person notices, and adjusts accordingly.
- Q3Open answer
What's a connection or pattern this person has spotted that others on the team missed? What signaled it to them?
Communicating direction
- Q4Rating (1-5)
I can articulate where this person/team is going in 1-2 sentences — and they'd recognize my version as correct.
- Q5Rating (1-5)
This person's strategic message stays consistent over time — they don't change direction every quarter.
- Q6Rating (1-5)
This person connects daily decisions to the strategic direction — they don't just announce strategy and disappear.
- Q7Multiple choice
How would you describe this person's strategic direction?
- — Clear and stable — I can articulate it without thinking
- — Clear most of the time — occasionally drifts
- — Clear in big meetings, fuzzy day-to-day
- — More aspirational than concrete — "win" but no path
- — I'm not sure what the strategy is
Trade-offs
- Q8Rating (1-5)
This person is willing to say no to good opportunities that don't fit the strategy.
- Q9Rating (1-5)
When this person makes a strategic choice, they're honest about what we're giving up — not just what we're chasing.
- Q10Open answer
If you could ask this person to refocus on one thing and let go of one other thing, what would it be?
The research behind these questions
Drawn from Roger Martin's Playing to Win on strategy as a cascade of choices, Michael Porter's foundational HBR work on strategic positioning and trade-offs, Rita McGrath's End of Competitive Advantage on continuous strategy in volatile contexts, Cynthia Montgomery's The Strategist on the leader's strategic role, and McKinsey's strategic-execution research. Each question targets a specific behavior the audience can observe — not vague 'strategic vision' rating.
References
- — Roger Martin & A.G. Lafley — Playing to Win
- — Michael Porter — competitive strategy work (HBR)
- — Rita McGrath — The End of Competitive Advantage (Columbia Business School)
- — Cynthia Montgomery — The Strategist (Harvard Business School)
- — McKinsey & Company — strategy execution research
Ready to run this round on yourself?
Sign up, pick this template, answer it about yourself, and send the same questions to the people who've been in the room with you. The gap between your view and theirs is where the actual learning lives.