The Introverted PM's Guide to Product Strategy: A Collaborative Approach

A 5-step workshop to building strategic pillars collaboratively

In my last post, I talked about setting product vision. Once you have that vision, the next step is strategizing how you're going to get there. I love framing product strategy around identifying strategic pillars—the 3-5 focus areas that will guide your team's decisions and roadmap.

But here's where most teams go wrong: They either skip the strategic planning process entirely (and wonder why their strategy feels disconnected from reality) or they run brainstorming sessions that favor the loudest voices in the room.

This guide outlines a structured process to craft a product strategy by identifying strategic pillars through a collaborative workshop. I’ve incorporated practices that levels the playing field - giving everyone, including the quiet voices, space to contribute.

Before You Start: Set Yourself Up for Success

Invite the right people. Include engineers, designers, and key stakeholders—but keep it to 8-10 people max. You want diverse perspectives without chaos.

Schedule ample time. I've seen this done over two intensive days or 3-5 sessions of 1-2 hours spread over a week. If it’s broken up into smaller sessions, don't let it drag too long or you'll lose momentum.

Prepare ahead. Set up a collaboration space with whiteboards and sticky notes, or use Mural/FigJam for virtual sessions.

Assign roles. Decide on a facilitator (often you) and a dedicated notetaker. As the facilitator, you play a critical role in making sure the discussions stay on course, and to level the playing field.

5 steps to building strategy collaboratively

Step 1: Brainstorm Customer Problems

Start by asking participants to brainstorm pain points or problems they've observed. These can come from customer feedback, data analysis, support tickets, or market research.

Use silent brainstorming first. Give everyone 15-20 minutes to independently write down problems without interference from others. This is where you level the playing field for diverse personality and working styles — it ensures the loudest voices or people with the highest titles don't immediately steer the conversation.

Encourage quantity over quality at this stage. You're looking for 50-150 problem statements covering user experience issues, operational inefficiencies, technical gaps, or market opportunities.

Step 2: Cluster Problems into Themes

Now comes the collaborative part. Group related problems into broader themes. For example, if you're seeing "onboarding drop-off" and "low offer take rate," these might cluster into "user activation."

Encourage everyone to participate. This is where introverts’ pattern-recognition skills may shine. Label each opportunity problem areas with a short description.

Aim for 8-10 problem clusters with short, clear names.

Step 3: Flip Problem Themes into Opportunities

Reframe each problem cluster into an opportunity statement. For example:

Problem: "Developers struggle to find relevant information."

Opportunity: "Make information discovery for developers seamless."

This shift is crucial—it moves the team from dwelling on what's wrong to envisioning what's possible.

Step 4: Prioritize the Opportunities

Evaluate opportunities using a prioritization framework. These become your strategic pillars. You can use whatever prioritization method your company prefers, but I've found a simple 2x2 framework works well when time is tight:

• High Impact, Low Effort: Quick wins

• High Impact, High Effort: Strategic investments

• Low Impact, Low Effort: Maybe later

• Low Impact, High Effort: Avoid

Do this as a group exercise. Create an area on the white board for opportunities that need debate. When debating, encourage the silent ones in the room to speak up.

Once this exercise is done, identify the top 3-5 areas your team should focus on - these will be Strategic Pillars. It’s typically a mix of the Quick Wins (High Impact, Low Effort) balanced with Strategic Investments (High Impact, High Effort).

Validate the choices with the group before moving on to the next step.

Step 5: Create "How Might We" Statements

For each strategic pillar, craft 2-3 "How Might We" (HMW) statements to guide ideation:

E.g. Pillar: "Increase user engagement (for a data API product)"

HMW: "How might we make our data more real-time?"
HMW: "How might we help users understand how to better use our data?"

These statements will guide your team as they brainstorm solutions and build your roadmap.

The Unexpected Edge of the Introverted Facilitator

I was a nervous wreck before I facilitated the first workshop like this. I've run these workshops quite a few times now, and here is something encouraging that I've learned: teams often respond well to facilitators who guide through structure and create space for everyone to contribute.

I’ve been told how such workshops can fail to deliver what it promises when the facilitators dominate the conversation or when they let a few people do that.

That's the introvert advantage in action.

There are so many Product Strategy frameworks out there. What have you found work well? I’d love to hear more.