Overview
Most strategy misalignment does not come from disagreement. It comes from people using the same words to mean different things. Your VP of Engineering says "scalability" and means infrastructure. Your Head of Sales says "scalability" and means enterprise features. Your CPO says "scalability" and means expanding to a new market segment. Everyone nods in the meeting, then goes and builds different things.
This workshop forces those invisible misalignments into the open. By the end of 90 minutes, your leadership team will have a shared strategy canvas, a stack-ranked list of priorities, and documented commitments they can point back to when trade-offs arise.
Who this is for: Product leaders facilitating alignment across a cross-functional leadership team (VP/Director level). Works for teams of 5-10 people.
Time required: 90 minutes (with a 5-minute break between Parts 2 and 3)
What participants will walk away with:
Materials Needed
Before the workshop:
Tools to reference during the session:
Facilitator prep (30 minutes before):
Pre-work email (send 48 hours before):
Subject: Strategy Alignment Workshop — Wednesday at 2pm
>
Attached is a one-pager summarizing our current product strategy. Please review it before the session.
>
Come prepared with your top 3 strategic priorities for the next 6-12 months, written down. Do not share these with anyone before the workshop — we need unbiased inputs.
>
The session runs 90 minutes with a 5-minute break. Please block your calendar for the full time — arriving late or leaving early significantly reduces the quality of the output.
>
If you have questions about the format, ask me directly rather than discussing with other participants.
Part 1: Strategy Canvas — Making the Invisible Visible (25 minutes)
What this accomplishes
The strategy canvas forces leadership to articulate what the company is actually competing on — not what the pitch deck says, but what the team genuinely believes drives customer value. It consistently reveals that leaders carry different mental models of the product's strategic position.
Facilitator instructions
Set up (2 minutes):
Draw a grid on the board with the following columns across the top:
And these rows down the left side:
Silent fill (8 minutes):
Give each participant a stack of sticky notes. Ask them to write one sticky note per cell for the "Our Product" column — their honest, personal answer. No discussion. No looking at neighbors.
This silence is critical. The moment someone speaks, anchoring bias takes over and you lose the diversity of perspectives that makes this exercise valuable.
Reveal and discuss (15 minutes):
Go row by row. Have everyone place their sticky notes on the board simultaneously.
For each row, use this facilitation script:
"Let's look at the spread. Where do we agree? Where do we diverge? I want to hear from someone whose answer is different from the majority — what information are you drawing on?"
What to watch for:
Document: Photograph the board. Highlight the 2-3 biggest divergences — these become inputs for Part 2.
Part 2: "What Would Have to Be True" (25 minutes)
What this accomplishes
This framework, originally from Roger Martin's strategy work, converts abstract strategic debates into testable hypotheses. Instead of arguing whether Priority A or Priority B is more important, you ask: "What would have to be true about the market, our capabilities, and our customers for Priority A to be the right bet?"
This depersonalizes strategic disagreements. People stop defending positions and start evaluating assumptions.
Facilitator instructions
Frame the exercise (3 minutes):
Take the top 3-4 strategic priorities from the pre-work. Write each on the board. If the strategy canvas surfaced a major disagreement, add that as a priority to evaluate.
Say to the room:
"We are not going to debate which of these is most important yet. First, we need to understand what each priority is actually betting on. For each one, we will answer: What would have to be true about our customers, our capabilities, and our market for this to be the right priority?"
Small group work (12 minutes):
Split into groups of 2-3. Assign each group one priority. Give them a template with three columns:
| Customer assumptions | Capability assumptions | Market assumptions |
|---|---|---|
| (What must customers want or do?) | (What must we be able to build or deliver?) | (What must the market look like?) |
Each group fills in the assumptions for their assigned priority. Encourage specificity: "Enterprise customers want self-serve onboarding" is better than "customers want a good experience."
Share-out and stress test (10 minutes):
Each group presents their assumptions in 2 minutes. After each presentation, the rest of the room has 1 minute to challenge:
"Which of these assumptions are we most uncertain about? Which ones can we test in the next 30 days?"
Mark each assumption as: Known (we have data), Believed (strong intuition, no data), or Unknown (we are guessing).
Key facilitation tip: If a priority has mostly "Unknown" assumptions, it is a higher-risk bet. That does not mean it is wrong — but the team should acknowledge the risk explicitly.
Example output from this exercise:
| Priority: "Expand into mid-market" | Status |
|---|---|
| Customer: Mid-market companies (50-500 employees) need our product category | Believed |
| Customer: They will pay $500-2000/month for our tier of solution | Unknown |
| Capability: We can build a self-serve onboarding flow in Q2 | Believed |
| Capability: Our infrastructure can handle 10x the account volume | Known |
| Market: The mid-market PM tools segment is growing, not consolidating | Unknown |
In this example, the two "Unknown" assumptions — willingness to pay and market direction — become immediate research priorities. The team should not commit to this priority until those assumptions move to "Believed" or "Known."
Take a 5-minute break here. People need to reset before the ranking exercise.
Part 3: Priority Stack Ranking (25 minutes)
What this accomplishes
This exercise produces a single, ordered list of strategic priorities that the room has agreed to. Not a 2x2 matrix. Not a tier list. A stack rank — because in practice, when two priorities compete for the same engineering team or the same quarter, you need to know which one wins.
Facilitator instructions
Individual ranking (5 minutes):
Give each participant a card or sheet listing all the priorities discussed. Ask them to rank from #1 (most important) to last, privately. They should consider:
If participants want a more structured approach, point them to the RICE framework as a mental model for evaluating Reach, Impact, Confidence, and Effort — though for this exercise, gut ranking followed by discussion is usually more productive than scoring.
Dot voting (5 minutes):
Each person gets 3 dots (or digital votes). Place them on their top 3 priorities. Dots can be stacked (all 3 on one priority is valid).
Tally the results visibly.
Debate round (10 minutes):
If the top 2 are clear, move to commitment. If there is a close call:
"We have a near-tie between [X] and [Y]. I want to hear one argument for X from someone who voted for Y, and one argument for Y from someone who voted for X."
This cross-advocacy technique prevents people from digging into positions. It forces the room to genuinely consider the other side.
Final ranking (5 minutes):
After the debate, do one final show-of-hands vote on the order. If consensus emerges, great. If not, the most senior decision-maker in the room makes the call — but now they are making it with full visibility into the trade-offs.
Write the final stack rank on the board. Number each item clearly.
Part 4: Commitment Documentation (15 minutes)
What this accomplishes
The most common failure mode of strategy workshops is that people leave aligned but write nothing down. Two weeks later, everyone remembers the workshop slightly differently. This section prevents that.
Facilitator instructions
Document the following on a shared doc (screen-shared or projected):
For each priority in the stack rank, record:
Facilitator script for kill criteria:
"This is the most important and most uncomfortable field. I need each priority owner to answer: what would you see in the next 30-60 days that would make you say 'we should stop investing here'? If nothing could change your mind, we are not making a strategic decision — we are making a commitment of faith."
Close the workshop (5 minutes):
Read back the full stack rank with owners and first actions. Ask for explicit confirmation:
"Does everyone in this room agree that this is our priority order, and that they will support these priorities even when their own team's backlog competes with them?"
Get verbal yes from every person. Note any explicit disagreements — these are not failures, they are honest signals to track.
Adapting This Workshop for Different Contexts
For early-stage startups (seed to Series A)
Skip Part 3 (Priority Stack Ranking). At this stage, you likely have 1-2 strategic bets, not 5. Instead, spend the extra 25 minutes going deeper in Part 2 — test every assumption in the "What Would Have to Be True" framework and assign someone to validate the riskiest ones within 2 weeks. Startups fail more often from unvalidated assumptions than from wrong priorities.
For large organizations (100+ people in the product org)
Run this workshop at each level of the org separately — first with VPs, then with Directors using the VP output as input, then with individual team leads. Each level translates the priorities from the level above into their own stack rank. The commitment document from each level feeds into the next. Budget a full week for the cascade.
For remote-first teams across time zones
Split the workshop into two 60-minute async+sync sessions. Session 1 (async): participants complete Parts 1 and 2 independently using a shared Miro board with a 48-hour deadline. Session 2 (sync): the group convenes for Parts 3 and 4, using the async outputs as inputs. This requires more facilitator setup but produces equally strong results.
For teams that have never done strategy alignment
Add a 15-minute "Strategy 101" preamble before Part 1 where you define what product strategy means for your organization. Without this shared vocabulary, Part 1 will stall on definitional debates. Use a simple frame: strategy is the set of choices about where to play, how to win, and what to build — and equally important, what not to build.
Next Steps for the Facilitator
Within 24 hours of the workshop:
For teams that want to translate priorities into a scored backlog, the RICE calculator is useful for converting strategic priorities into actionable ranking at the feature level.
Facilitator Tips
On managing the room:
On timing:
On remote facilitation:
On follow-through:
Common pitfalls: