A quick test for whether an organization's strategy is actually clear: interview members of the executive team individually and ask them to state the strategy. Getting a materially different answer from almost everyone is itself the diagnosis — the The Decision Stack (Eriksson)'s strategy layer isn't real yet, it's aspirational language each leader is filling in differently. Cited alongside the finding that roughly 95% of employees can't name their organization's strategy (HBR).
Related: Optionality Avoidance as a Strategy Failure Mode, Laddering (Strategy-Alignment Diagnostic), Vision Vacuum: No Vision, Not Bad Vision, Is the Real Failure Mode.
Eriksson's closing recommendation extends the exec-interview diagnostic past the leadership team: ask people across the whole company, not just executives, what they think the strategy is. The value is the same mechanism as the exec-only version — a group setting lets people nod along without actually holding the same mental model, so individual answers reveal real divergence — but broadened to all-hands scale, the resulting spread of answers becomes visible, legible proof to the rest of the organization that action on strategic clarity is actually needed, rather than a diagnosis only leadership sees.
A specific version of this diagnostic: ask a prospective employer how the roadmap gets built and where the dates on it come from. Cagan says the difference between feature-team and product-team cultures 'is not subtle' — it shows up immediately in how someone answers this question, without needing to ask about strategy directly.
'The thing about a feature team and a product team is there are not subtle differences — there are big differences.'
Job-seekers can ask these specific questions in interviews to quickly diagnose which operating model a company actually runs.
Janakiraman's Present Forward: A Five-Phase Process for Problem-Focused Strategy treats leadership interviews as a required Preparation-phase input, run before the strategy working group builds anything. Beyond gathering context, he argues the PM should directly ask each leader about their pet ideas — the things they personally want to see built — rather than avoiding the topic to look independent. He frames this as a sign of strength and humility rather than weakness: surfacing a leader's pet idea early lets the working group evaluate it on the same footing as everything else, instead of having it resurface as a surprise veto during rollout. He illustrates the risk of skipping this with a "fruit story" anecdote about an unaired leader preference derailing a plan late in the process.
An analogy for the cost of skipping stakeholder interviews before proposing a strategy: bringing a reviewer a mango, then an apple, then a banana — each rejected — because the reviewer's specific preference was never asked about first. A sound strategy can still get shot down on preference grounds rather than substance if leadership's preferences weren't surfaced beforehand.
A repeatable set of questions for leadership interviews during Present Forward: A Five-Phase Process for Problem-Focused Strategy prep:
Leaders to interview are divided among Strategy Working Group (Cross-Functional Strategy Co-Creation Team) members for 1:1 sessions rather than one person interviewing everyone. The same question set is reused informally throughout the process to keep the PM's own manager aligned, not just at kickoff.