I've run positioning workshops that changed everything and positioning workshops that produced the phrase "innovative solution provider."
The difference wasn't the framework I used. It wasn't the quality of participants. It wasn't how much pre-work I assigned.
The difference was whether I controlled the room or let the room control me.
The best positioning workshop I ever facilitated took two hours. We walked in positioned as "workflow automation software." We walked out positioned as "compliance automation for regulated industries." Revenue grew 40% the next quarter because we finally knew who we were selling to and why they'd care.
The worst positioning workshop I ever facilitated took four hours and produced a positioning statement so generic we couldn't use it: "We help innovative companies transform their business processes with intelligent automation."
Both workshops had the same stakeholders. Both used similar exercises. The difference was that in the first workshop, I shut down the conversations that derailed positioning. In the second workshop, I let those conversations happen because I thought good facilitation meant letting everyone speak.
I was wrong. Good facilitation means protecting the goal from the distractions that sound productive but aren't.
The Three Conversations That Kill Positioning Workshops
Every positioning workshop has conversations that feel important but destroy your ability to reach a decision.
I've learned to identify these conversations in the first 15 minutes and shut them down immediately, or they'll consume the entire session.
Conversation 1: The Product Roadmap Debate
Someone will say: "We can't position ourselves as X because we're building Y next quarter."
This derails positioning workshops more than anything else. It shifts the conversation from "who are we today" to "who will we be in the future," which is unknowable and endlessly debatable.
I facilitated a workshop where this consumed 90 minutes. Product wanted to position around AI capabilities we were building. Sales wanted to position around the workflow automation we actually sold. We debated the roadmap instead of making a positioning decision.
The workshop produced nothing useful because we tried to position a future product instead of our current reality.
Now when someone raises the roadmap, I say: "We're positioning the product we can sell tomorrow, not the product we'll build next year. If the roadmap changes positioning, we'll update positioning then."
This sounds harsh. It's necessary. Positioning is about making a decision now, not hedging for every possible future.
Conversation 2: The "But We Also Do This" Tangent
Someone will say: "We can't say we're focused on X because we also do Y and Z."
This is the conversation that makes positioning statements balloon into paragraphs covering every capability and use case.
I watched a workshop try to incorporate five different use cases into one positioning statement because each stakeholder advocated for their favorite customer. The resulting statement was: "We help companies improve efficiency, reduce costs, ensure compliance, accelerate innovation, and enhance customer experience."
That's not positioning. That's a list of generic benefits.
The breakthrough came when I asked: "If we could only keep one of these, which one actually differentiates us from alternatives?"
The room went silent. Then someone said: "Honestly, probably compliance. That's the pain point where customers say we're uniquely good."
Boom. Positioning clarity.
Now when someone says "but we also do this," I ask: "Yes, but which one creates urgency? Which one makes prospects say 'I need this now' instead of 'that's nice to have'?"
This forces the conversation from capabilities (what we do) to differentiation (what we do better than alternatives in a way that matters).
Conversation 3: The Wordsmithing Death Spiral
Someone will say: "I don't love the word 'transform.' Can we use 'optimize' instead?"
Then someone else will say: "Actually, 'revolutionize' is stronger."
Now you're debating synonyms instead of making positioning decisions.
I've been in workshops where we spent 40 minutes debating whether to say "enterprise companies" or "large organizations" or "global businesses."
The participants felt productive because we were refining language. We were actually avoiding the hard decision: who is our customer and why do they care?
I now ban wordsmithing during positioning workshops. I literally say: "We're making positioning decisions today. We'll wordsmith next week. If the concept is right, the exact words don't matter yet."
This creates discomfort. Stakeholders want to contribute, and wordsmithing feels like contributing without requiring them to make hard strategic choices.
But positioning workshops aren't about making everyone feel useful. They're about making decisions that have been too hard to make in normal meetings.
The Workshop Structure That Actually Works
After running dozens of positioning workshops, I've landed on a structure that forces decisions instead of facilitating endless discussion.
The entire workshop is 90 minutes. Not two hours. Not a half-day. Exactly 90 minutes.
Why? Because positioning decisions don't require more time—they require forcing mechanisms. When you have two hours, people fill two hours with discussion. When you have 90 minutes and a clear sequence, they make decisions.
Pre-Work (Assigned One Week Before)
I send three questions to every participant:
- "Write down the exact words a customer used in the last month to describe the problem we solve."
- "Name one competitor we lose to and why we lose."
- "If you had to explain what we do to someone at a cocktail party in one sentence, what would you say?"
These questions do two things. First, they surface the disconnects before the workshop. If Product describes the problem as "inefficient workflows" and Sales describes it as "compliance risk," I know we have a fundamental disagreement to resolve.
Second, they force stakeholders to think concretely instead of abstractly. "What would you say at a cocktail party" generates better positioning than "how would you describe our value proposition" because it requires normal human language.
I compile the answers into a one-page pre-read showing where we're aligned and where we're disconnected. This doc becomes the agenda.
Exercise 1: The Customer Problem (30 Minutes)
I start every workshop with: "What problem do customers have right before they start looking for our product?"
Not "what problem do we solve"—what problem do they have. This distinction matters.
I put stakeholders in breakout groups of 3-4 and give them 15 minutes to write down:
- The trigger event that creates urgency
- What the customer tried before finding us
- Why those alternatives didn't work
Then we reconvene and I force convergence. Each group shares. I write the common threads on a whiteboard. I ask: "Where do we agree? Where do we disagree?"
Usually we agree on the symptoms but disagree on the underlying problem.
In one workshop, everyone agreed customers struggled with "too much manual work." But when we dug deeper, Product thought the underlying problem was "inefficient processes." Sales thought it was "compliance risk from human error."
Those are different problems requiring different positioning.
I forced the decision: "Which problem creates budget urgency? Which one makes customers buy in 30 days instead of 6 months?"
Sales said: "Compliance risk. When they think it's an efficiency problem, they wait. When they think it's a compliance problem, they buy immediately because they're scared."
That became our positioning focus: compliance risk reduction, not efficiency improvement.
The key is moving from divergent discussion to convergent decision in 30 minutes. We're not seeking perfect consensus—we're seeking enough clarity to make a positioning choice.
Exercise 2: The Competitive Alternative (20 Minutes)
Next I ask: "If a customer decides not to buy us, what do they do instead?"
This is different from "who are our competitors." It's about understanding the actual alternatives customers consider.
In one workshop, we thought our competitors were other software vendors. When we asked what customers did if they didn't buy us, the answer was: "They hire more people."
That changed everything. We weren't competing against other software. We were competing against headcount. Our positioning needed to emphasize not just ROI, but ROI that's better than hiring.
I split the room into pairs and give them 10 minutes to map:
- What customers do if they don't buy us (status quo, competitor, hire, build internal)
- Why that alternative is appealing
- Where that alternative fails
Then we reconvene and I force the hard question: "What do we do that none of these alternatives do well?"
This is where positioning crystallizes. You're not positioning against your entire market—you're positioning against the specific alternatives your customers actually consider.
In one workshop, we realized every alternative (build internal, hire consultants, use competitor software) required deep technical expertise to implement. We were the only option that worked out-of-the-box for non-technical teams.
That became our differentiator: "Compliance automation for teams without compliance engineers."
Exercise 3: The Positioning Statement (40 Minutes)
The final exercise is filling in this template:
For [target customer] Who [have this problem] Our product is [category] That [key benefit] Unlike [competitive alternative] We [unique differentiator]
I break stakeholders into two groups and give them 20 minutes to complete the template based on what we've decided in exercises 1 and 2.
Then each group presents. We don't debate which is better—we identify where they diverge and why.
Usually the divergence is on category or target customer.
In one workshop, one group said "compliance software for healthcare companies." The other said "workflow automation for regulated industries."
These are fundamentally different positions. Healthcare compliance software is a narrow category with clear competitors. Workflow automation for regulated industries is broader but less specific.
I forced the decision by asking: "Which one do customers immediately understand? Which one makes them say 'that's for me'?"
The healthcare team said that when they said "workflow automation," healthcare customers didn't immediately see relevance. When they said "healthcare compliance," customers immediately understood.
We positioned as healthcare compliance software, not workflow automation.
The key is that I'm not seeking consensus—I'm forcing a decision by making the tradeoffs explicit. You can be broad or specific. You can be category-creating or category-conforming. But you have to choose.
The Facilitation Tactics That Make It Work
The structure matters, but execution determines whether you actually get decisions.
Tactic 1: Designate a Decider
At the start of every workshop, I ask: "Who makes the final call if we can't reach consensus?"
Usually it's the VP Product Marketing or the CEO. Sometimes it's the CRO if positioning is primarily a sales problem.
Identifying the decider upfront changes the dynamic. Stakeholders know their job is to inform the decision, not negotiate until everyone's happy.
I facilitated a workshop where we couldn't agree whether to position for enterprise or mid-market. The debate was circular.
I stopped the conversation and said: "We have 10 minutes left. [CRO name], you're the decider. Based on what you've heard, which positioning creates more pipeline?"
She said: "Mid-market. Our enterprise deals take 18 months. Our mid-market deals close in 60 days. Let's position for velocity."
Decision made. Workshop complete.
Without a designated decider, workshops devolve into consensus-seeking, which produces generic positioning.
Tactic 2: Use a Timer
I run every exercise with a visible countdown timer.
When I say "you have 15 minutes," I project a timer on the screen. When it hits zero, we move on.
This sounds aggressive. It's essential.
Without a timer, discussions expand to fill available time. With a timer, people make decisions because they know time is finite.
I facilitated a workshop where we were stuck debating target customer. I said: "You have 5 minutes to make a decision. If you can't decide, I'll decide for you based on revenue data."
They decided in 3 minutes.
The timer creates urgency that's otherwise missing from positioning discussions.
Tactic 3: Document Live
I type the positioning statement live during the workshop on a shared screen.
As stakeholders talk, I translate their discussion into positioning language. "So what I'm hearing is: For mid-market healthcare companies who struggle with manual compliance documentation..."
This does two things. First, it forces clarity. When people see their abstract discussion turned into concrete positioning language, they realize whether it actually makes sense.
Second, it prevents the "wait, what did we decide?" problem. By the end of the workshop, we have a documented positioning statement, not just a conversation.
Tactic 4: Schedule the Follow-Up Before You Leave
The last thing I do in every positioning workshop is schedule a 30-minute follow-up meeting one week later.
This meeting has one agenda item: review the positioning statement with fresh eyes and make final edits.
Why? Because positioning that sounds great in a 90-minute workshop sometimes sounds terrible when you read it cold the next week.
The one-week gap gives stakeholders time to reality-test the positioning with customers or sales teams before we finalize it.
I've had workshops where the positioning we agreed on sounded perfect, then someone tested it with a customer and the customer looked confused. We adjusted before launching it broadly.
The follow-up meeting is also where we handle wordsmithing. I banned it during the workshop—now it's welcome.
When Workshops Fail (And What To Do Instead)
Not every positioning decision should happen in a workshop.
I've facilitated workshops that failed because the real blocker wasn't lack of alignment—it was lack of data.
If you don't know who your best customers are, a positioning workshop won't help. You need customer segmentation analysis first.
If you don't know why you win or lose against competitors, a positioning workshop won't help. You need win/loss interviews first.
If you don't have product-market fit, a positioning workshop won't help. You need customer discovery first.
Positioning workshops work when you have data but lack decision-making clarity. They fail when you lack the data to make informed decisions.
I've also learned that some positioning decisions can't happen in a group setting because the political dynamics are too fraught.
I worked with a company where Product and Sales had fundamentally incompatible views of the product strategy. Product wanted to position for a future vision. Sales wanted to position for current capabilities.
I tried to run a workshop. It turned into a two-hour argument that resolved nothing.
I killed the workshop and instead interviewed the CEO privately. I laid out the options: position for current state or position for future state. I explained the tradeoffs of each.
The CEO made the call: position for current state, sell what we can sell today.
I documented the decision and sent it to the team. Some people were unhappy. But we had positioning clarity, which we didn't have before.
Sometimes the facilitator's job isn't to build consensus—it's to escalate the decision to someone who can make it without consensus.
What Good Positioning Feels Like
You'll know the workshop worked when:
Sales can explain your positioning to a prospect in one sentence. If they need three sentences, it's too complicated.
Customers immediately understand what category you're in. If they ask "so what is it?" your category isn't clear.
You can articulate why prospects choose you over specific alternatives. If you can only say "we're better," your differentiation isn't defensible.
Stakeholders stop arguing about positioning after the workshop. If the debate continues, you didn't actually make a decision.
The two-hour workshop that changed our category produced all of these outcomes. We walked out knowing exactly who we were, who we served, and why they'd choose us.
The four-hour workshop that produced "innovative solution provider" produced none of them. We walked out with words on a page and continued disagreement about what we actually did.
The difference wasn't the time invested. It was whether I forced decisions or facilitated endless discussion.
Positioning workshops aren't therapy sessions where everyone gets to share. They're decision-making sessions where you resolve the strategic ambiguity that's been paralyzing your go-to-market.
When you treat them that way, two hours is plenty.