The 3 Roles That Build Great Strategy Talent
Playing The Realist, The Investor, and The Challenger as a Product Manager and a Product Leader.
If you have read my last post The Unhappy Path of Product Strategy, you would know that I am a big supporter of Product Managers (and other builders/operators of the company) to map out the (if not all, some of the) unhappy paths the strategic execution can take, rather than work it out later on the go.
The parallel I take is : Customer Journeys. You would most probably never execute and take into production a happy path journey of a product. You will map out some ifs and buts (if not all), some boundary conditions, some error states and more - and plan around them/build around them before rolling out a version of your product.
Now if you extrapolate it to Product Strategy - the number of variables just go up. You’re not only dealing with engineers/designers/internal stakeholders on one side and users on other side, but you’re also dealing with all that can change - markets, economy, user preference, competition and more. Unhappy paths in strategy are more likely than unhappy paths in a product/feature - yet they are most under-addressed in product strategy.
(Below survey result is for the question: Which of the below is well covered in your product strategy exercise?)
Why dealing with Unhappy Path is tough?
I recently presented The Unhappy Path of Product Strategy at Product Academy Summit in Zurich and had the opportunity to interact with the local product community.
The questions ranged from:
Do you protect your happy path (the OG Product Strategy), or continue to evolve it (like at 6 months/1 year cycles)? What comes first?
As a PM, How do I get commitment on resources and support needed to execute on product Strategy?
What is the role of separate Product Strategy Unit in such a case?
and so on.
What I realized more and more is the human side of Product Management.
The complex part is writing a good product strategy down, but even tougher is dealing with the three human aspects of creating and executing on it:
The Realist: Being that person in your company who raises concerns about what can go wrong
The Investor: The Being that person in your company who asks commitment on resources, people and stakeholder buy-ins
The Challenger: Being that person in your company who challenges the strategy as it is and wants to revisit it
As a Product Leader or a Product Manager, taking these roles at different points in product strategy cycle can be challenging, because you default human tendency is just to execute on it and assume “strategy is someone else’s problem” or even worse, let’s not touch strategy until the next planning cycle.
But nothing in the world moves as per your company’s planning cycle - the markets don’t, customers don’t and your competitor doesn’t.
How to deal with it as a Product Manager?
Hence, if you’re a Product Manager - the brave choice you can take and practice early in your career is that you’re The Realist in your product’s strategy, The Investor when getting commitment from the company, and The Challenger when you see core strategy assumptions changing.
🔍 The Realist: Spotting the Cracks Before They Widen
As a junior PM, you're closest to the ground — customer feedback, delivery risks, design trade-offs, edge cases. You’re in the weeds.
How to be The Realist:
Raise red flags early when something doesn’t line up between what’s in the strategy deck and what you’re hearing from the market or your dev/design team.
Use data + anecdotes to articulate risk: “Here’s what the dashboard says, and here’s what that client told us last week.”
Don’t fear being the voice of caution — it’s a muscle that builds trust, not hesitation.
🧠 Strategy isn’t just about aspiration. It's about making good bets — and Realists challenge bad odds before others even see them.
🤝 The Investor: Earning the Right to Resources
You may not have budget control, but you can influence resourcing by making strong business cases.
How to be The Investor:
Frame product ideas in terms of impact: “This feature can unlock X% retention lift for Segment A.”
Align with company objectives: “This aligns with our Q3 growth targets in the mid-market space.”
Use rough ROI models or simple effort/impact maps to show the why behind your ask.
Don’t wait for someone else to ask leadership for help. If you need design bandwidth or help from marketing — advocate for it.
💡 The best early PMs don’t just request resources — they articulate the return.
❓ The Challenger: Product Strategy Is Not Sacred
Even as a junior, you’re allowed — expected, actually — to question things when they stop making sense.
How to be The Challenger:
If priorities shift or market realities change, raise the strategic implications.
Ask questions like, “If this assumption was wrong, what would we need to rethink?”
Be respectful, but don’t defer to hierarchy blindly. Sometimes your fresh perspective is the one least trapped by past decisions.
🛠️ Strategy is a living document, not a fossil. Challengers help keep it alive.
How to deal with it as a Product Leader?
As a Product Leader, you should be a good example for your Product Managers. You’re not just a participant in the strategy — you’re shaping it, advocating for it, defending it, and evolving it - and setting a good mentorship for others.
But here's the catch: everyone’s watching a Product Leader. So these roles take more finesse as you grow senior.
🔍 The Realist: Stress-Testing the Story
You’re setting the direction. But more than that, you’re the one responsible for saying “this won’t scale” or “we’re not ready.”
How to Lead as The Realist:
Build in review moments to validate assumptions, not just milestones.
Encourage dissent in strategy sessions — realism thrives where people feel safe to say “this part doesn’t work.”
Model realism as a strength, not skepticism. When you surface risks, you’re protecting the team from false confidence.
🤝 The Investor: Making the Bet and Defending It
You are the one asking for and justifying the resources now — headcount, budget, cross-functional buy-in.
How to Lead as The Investor:
Package strategy in business terms for your execs. Tie product outcomes to revenue, cost, retention, or strategic leverage.
Build cross-functional coalitions early: engage sales, marketing, ops, and customer success as co-owners of the vision.
Set clear priorities — investment isn’t just money, it’s what not to do.
💼 The best product leaders don’t ask for more. They show how more unlocks greater.
❓ The Challenger: Be Willing to Unwrite Your Own Strategy
Ironically, the hardest person to challenge might be... yourself. You created the strategy — can you admit when it's time to pivot?
How to Lead as The Challenger:
Set a cadence for intentional reflection: what’s changed externally? Which hypotheses no longer hold?
Encourage your team to bring uncomfortable truths — and actually act on them.
Show that revisiting strategy isn’t a sign of weakness, it’s a signal of maturity.
🔁 Strong strategies are flexible. And strong leaders are too.
💬 Closing Thought
Whether you're just starting out or leading the product function, the strategy process isn’t a solo performance — it’s a rhythm of realism, investment, and challenge. The earlier you build fluency in these roles, the better you’ll navigate the messy middle of product work.
Be The Realist when things feel too easy.
Be The Investor when things get ambitious.
Be The Challenger when things no longer add up.
That’s how you stay close to the truth, the team, and the trajectory.
Well-researched and beautifully synthesized, Bandan
I only had one small question for this bullet point:
"• Build in review moments to validate assumptions, not just milestones."
I'm probably reading too closely, but whenever I see "validate," it means "prove that we were right," instead of what I understand the point of Discovery to be as "look for the weaknesses in our assumptions so we can disprove them and make a better hypothesis."
This next point allows for alternative points of view:
"Encourage dissent in strategy sessions — realism thrives where people feel safe to say “this part doesn’t work.”"
I.e., on't look to be right, or rubber-stamp something, but to look for ways the ideas can be challenged and improved.