When I talk to founders, CTOs, or product leaders about strengthening their product teams, they often jump straight to process frameworks or the latest productivity hack. Case studies rarely get a mention outside of marketing pitches, yet the case method is one of the most effective ways to develop practical product judgment on a team. This post is a deeper dive into why I’ve been using cases to grow product managers. It builds on some of my original thoughts with real‑world examples, and suggestions on how to make case sessions rewarding for your team.

What do we mean by “case study”?

In product circles, “case study” usually conjures up a glossy PDF about how a customer increased conversions with your SaaS tool. That’s not what I’m talking about. The case method comes from business schools (I know I can already feel the eyes rolling back in your head). These cases refer to taking a narrative description of a real situation, dissecting it, and deciding what you would do in the protagonist’s shoes. It simulates the messy reality of business scenarios without the risk of burning real money or failing on the job. As a note on the case method points out from a Stanford course, we can’t drop ourselves into another company’s decision‑making process, but we can “read descriptions of particular business situations and make decisions based upon the data we find there”. Each case sets up a complex situation with multiple problems and incomplete information, forcing participants to identify issues, weigh trade‑offs, and commit to a decision¹.

Unlike a tidy “problem set,” a case contains irrelevant details and ambiguous data to mimic real life. There’s no single right answer. What matters is the reasoning and the willingness to defend it. The instructor becomes a facilitator rather than a lecturer, and the classroom becomes a safe place to take risks. This low‑risk environment is exactly what product managers, at any level, lack in their day jobs. Unlike engineers, who can pop open a text editor and start experimenting, product managers don’t have a low risk place to roll back any changes.

Why case work pays off

Practice decision‑making in a safe space

Most folks learn by doing. They’ll ship features, handle incidents, and negotiate roadmaps. But on‑the‑job practice comes with consequences. Cases create a practice arena. Harvard Business School highlights how cases hone the ability to make decisions with limited information—just like in the real world. When you consistently work through ambiguous scenarios and defend your choices to peers, you build confidence and speed in your judgment².

Case sessions also develop higher‑order reasoning. Case studies engage participants in reflective discussion, encourage clinical and professional reasoning in a safe environment, and foster creative problem‑solving without putting real customers at risk. Because the problems are complex and the solutions uncertain, teams must share experiences and learn by doing to solve them.³

Build empathy and open‑mindedness

Good product managers step into their users’ shoes. The case method forces you to do this over and over. Harvard’s online program notes² that cases prompt you to consider scenarios from another person’s perspective and to think through circumstances, stakeholders and consequences. Collaborating with peers exposes you to different approaches and helps you become more open‑minded. For a PM, this translates into better stakeholder management and more thoughtful product decisions.

Improve long‑term recall and judgment

An academic review of the case‑method teaching (CMT) in organizational training concludes that participants get involved with real‑world challenges rather than analysing them from a distance. The authors found that CMT improves long‑term memory, enhances the quality of decision making and helps instructors understand individual differences between trainees⁴. That’s a trifecta for product teams: stronger recall of patterns, better decisions, and insight into how each PM thinks under pressure. That same research paper, identifies that one of the major benefits is teaching others the tacit knowledge needed around making effective decisions within your organization. That tacit knowledge only comes with observation and time within an organization but the case method can speed this up.

Encourage critical thinking and problem identification

One of the hidden benefits of working through cases is that they train your team to find the real problem. Stanford’s note emphasises that a “real asset” of the case method is that it forces you to identify problems rather than accept predefined questions. Similarly, UNSW’s teaching guidance lists the ability to identify critical versus extraneous factors as a key outcome.³ For PMs who often jump straight to solutions, this discipline of problem framing is priceless.

Running a case session with your team

You don’t need to be a professor to run a case exercise. Here’s how I’ve approached it:

1. Choose the right case. Pick a situation that resembles challenges your team faces, market entry decisions, platform migrations, ethical trade‑offs, or customer churn. A good case includes enough data to be credible but leaves gaps that require judgment. You can find public cases from business schools or write your own based on past projects (scrub the sensitive details).

2. Set the stage. I like to treat case reviews like case competitions where you have a set of time to assess the situation before discussion. Typically, I’ve let my teams take 15 - 30 minutes to review the case before the discussion begins. I’ve found timeboxing forces PMs to understand the problem as quickly as possible. Encourage them to outline the core problem, stakeholders, and at least one decision they’d make. Remind them that there’s no single correct answer and that the goal is to defend their reasoning. At the end of the timebox, the general discussion begins.

3. Facilitate, don’t lecture. During the session, resist the urge to give your solution right away. The case method works because participants wrestle with ambiguity and debate alternatives. Play the role of discussion leader, probing with questions like “What’s the real problem here?”, “Why do you think that’s the right choice?”, and “What information would change your mind?”. The UNSW case assessment guidelines suggests moving through stages of What? (clarification), Why? (analysis), What now? (recommendation), How? (implementation), and So what? (reflection). The UNSW guide also goes into more detail about effective Questioning during a case discussion.

4. Involve customers or cross‑functional partners. Cases don’t have to be purely theoretical. Invite a customer or a sales rep to play the role of stakeholder so your PMs can practise customer development questions. The point is to create a diverse set of perspectives.

5. Encourage reflection. After the discussion, have each participant summarise what they learned and how they might apply it to their current projects. Reflection cements the learning and surfaces differences between what people think they should do and what they actually do.

Dealing with common objections

“We don’t have time.” I hear this a lot. Carving out two hours for a case exercise once a quarter is a small investment compared with the cost of poor decisions. The time you spend practising in a safe environment pays dividends when you’re facing high‑stakes product choices. Remember that research shows case work improves long‑term memory and decision quality. Now that same study says that there’s also the added time of finding cases and evaluating them for suitability in your situation. In practice, I find I spend approximately one to two hours to find an appropriate case for my team.

“Aren’t we already learning on the job?” On‑the‑job experience is valuable, but it’s reactive and often punishes mistakes. Cases give PMs the space to experiment, take risks, and even “defend risky positions” without consequences. That kind of sandbox is hard to replicate in production.

“I’m worried about giving the answers.” Don’t. Your job as a product leader isn’t to monologue but to guide. By asking “why?” first and listening to your team’s reasoning, you may discover blind spots or creative solutions you hadn’t considered. The case method is as much about learning from your team as it is about teaching them.

Final thoughts

Cultivating product managers isn’t just about shipping more features or reading more blogs. It’s about building the muscle of judgment, empathy, and critical thinking. The case method offers a structured yet flexible way to practise those muscles. Studies show that case work improves decision‑making, fosters open‑mindedness, and provides a low‑risk environment for exploring alternative solutions. When you regularly expose your team to complex scenarios and ask them to justify their decisions, you raise the bar for product thinking across the board.

So the next time you’re planning a quarterly offsite or wondering how to level up your PMs, don’t default to another roadmap grooming session. Pull out a case, make some coffee, and practise making the hard calls before they matter. Your future products, and your team, will thank you.

Footnotes

1. https://web.stanford.edu/class/e145/2007_fall/materials/case_davis.htm ↩

2. https://online.hbs.edu/blog/post/case-study-method ↩ ↩²

3. https://www.teaching.unsw.edu.au/assessment-case-studies-and-scenarios ↩ ↩²

4. https://www.researchgate.net/publication/327807349_Case-method_teaching_advantages_and_disadvantages_in_organizational_training ↩