In the fast-moving world of product management, crafting and executing a solid strategy is often more complex than simply delivering features. Bandan Jot Singh’s recent article, “The 3 Roles That Build Great Strategy Talent,” offers a fresh and practical framework that product managers and leaders can adopt to navigate this complexity more effectively.

Singh identifies three critical roles that shape strong strategy talent: The Realist, The Investor, and The Challenger. These aren’t formal job titles but behavioral stances that individuals can embody at different points in the strategy process to ensure it’s robust, well-supported, and adaptable.

Why These Roles Matter

Much like mapping customer journeys involves planning for “unhappy paths” or edge cases, product strategy requires anticipating risks, securing resources, and revisiting assumptions continuously. Singh highlights how many teams neglect these “unhappy paths” in strategy, leaving their plans vulnerable to market shifts, stakeholder dynamics, and operational realities.

Breaking Down the Roles

• The Realist: This role is about spotting cracks early — the misalignments between what’s planned and what’s happening on the ground. For junior PMs especially, who are close to customer feedback and delivery challenges, raising early red flags backed by data builds trust and prevents costly surprises.
• The Investor: Getting buy-in and resources isn’t just about asking; it’s about making a persuasive business case. Framing requests in terms of impact, ROI, and alignment with company goals can move leadership to commit people, budget, and support.
• The Challenger: Strategy should never be set in stone. When priorities or market realities shift, challenging assumptions and advocating for pivots keeps the strategy alive and relevant. This role requires courage and a culture that welcomes questioning without fear.

Leadership’s Role

Singh also emphasizes how product leaders must embody these roles with greater finesse. They set the tone by encouraging dissent, packaging strategy in business language for executives, and demonstrating that revisiting strategy is a sign of strength, not failure.

What’s Missing?

While Singh’s framework is clear and actionable, the article doesn’t deeply address how organizational culture or hierarchy can impede these roles, especially the Challenger. Psychological safety and navigating internal politics are crucial elements for enabling these behaviors in practice.

Why You Should Read the Original

If you’re a product manager, leader, or anyone involved in strategic planning, Singh’s article offers a valuable lens to rethink how you engage with product strategy. It reminds us that strategy isn’t a static plan but a living, breathing process that requires a balance of realism, investment, and challenge — and that each of us can step into these roles to drive better outcomes.

You can read the full article here: The 3 Roles That Build Great Strategy Talent by Bandan Jot Singh

If you’re a product manager constantly juggling delivery deadlines and leadership expectations, Amy Mitchell’s recent article, “Make Strategy Your Side Project,” is a must-read. Rather than treating strategy as a distant, high-level exercise, Mitchell offers a fresh and practical take: strategy is something you build right alongside your day-to-day product work.

What Sets This Article Apart

Most advice on strategic thinking can feel overwhelming or disconnected from the reality of busy product teams. But Mitchell cuts through that noise by emphasizing small, solution-level strategy — the kind that solves recurring patterns or friction points within your product or team.

She debunks the myth that strategic projects come fully formed on your plate. Instead, you need to spot opportunities in customer feedback, cross-team friction, or delivery bottlenecks — and then build a case for them carefully, framing these projects as hypotheses rather than “big strategies” to manage skepticism and risk.

The Power of Starting Small and Following Through

One of the most compelling insights is how starting small and staying close to delivery work can set you apart. Mitchell points out that many product managers have ideas or decks, but few follow through when the work gets messy or unrewarded in the short term. This follow-through — involving stakeholders, tracking progress, and closing the loop — is what builds trust and influence.

Her “Billboard Test” is a simple but effective tool: Would your team be proud to say, “We figured that out. That changed how we operate”? If yes, you’re on the right track.

Why This Matters for Product Managers Today

In today’s fast-paced environments, leadership demands both immediate results and strategic thinking. Mitchell’s approach offers a way to reconcile those pressures, making strategy less of a distant moonshot and more of a continuous, manageable side effort.

Whether you’re trying to stand out in a crowded product team or earn more visibility with senior leaders, the article provides actionable advice for embedding strategy work into your routine without losing focus on delivery.

Final Thoughts

“Make Strategy Your Side Project” is a timely and practical guide for product managers who want to grow their strategic impact organically. By focusing on small, product-rooted projects and following through with rigor, you can earn the influence and visibility leadership is looking for.

If you’re ready to rethink how you approach strategy and want actionable steps to start today, I highly recommend reading Amy Mitchell’s full article.