Hiring Irreplaceable PMs: How to Hire the Talent AI Can't Replace (Part 1)

A 5-Part Series to Future-Proof Your Product Org

Welcome back to the Irreplaceable PM! In my last piece I discussed how AI is reshaping the role of Product Managers by making adaptability, strategic thinking, and systems thinking more essential than ever. Expertise and execution alone aren't sufficient anymore. To thrive now, PMs need to become high-agency generalists capable of leading not only without a playbook, but in areas no one has ever navigated before.

This follow-up turns the lens to you, the product leaders making critical hiring decisions. I'm advocating for a shift in your hiring strategy, moving away from narrowly-focused specialists with X-teen years of experience in "this industry" or with "that technology" or with “this business model”, and instead toward strategic, adaptable, high agency generalists. The PMs you hire today won't just ship features or own roadmaps. They'll determine how your company navigates ambiguity, how quickly it learns, and whether it builds the right thing at the right time. They'll either unlock new markets or miss the signals because they're following static playbooks or leveraging the same tactics that got them through "last time." They'll either challenge assumptions or perpetuate outdated ones. That's the difference between a generalist with range and a specialist stuck in a lane. Unfortunately, your job posting is requesting the wrong kind of person. This 5-pat series outlines exactly how to identify, attract, interview, and retain these irreplaceable PMs—and why high agency, learning mindset generalists are the most critical hire you can make right now.

Part 1: Why High Agency, Strategic Generalists Matter

AI is increasingly capable of doing the obvious work: executing tasks, synthesizing data, and replicating expertise. What it can’t do is navigate uncertainty, frame the right problem, or connect dots across seemingly unrelated domains. That’s where generalists thrive.

Strategic generalists are built for ambiguity. They move fluidly between contexts, learn on the fly, and orient quickly in unfamiliar territory. They don’t need a map; they build one. These are the people you want in the room when no playbook exists.

And let’s be honest. That’s the room we're all in these days.

The future has never felt more unpredictable—AI is evolving daily, reshaping our industries, our workflows, and our expectations. And yet, the pace of execution isn’t slowing down. We’re being asked to move faster, decide faster, build faster—often without clear precedent or reliable roadmaps. That’s why these kinds of people matter more than ever, right now. You need individuals who can lead without certainty, move forward in ambiguity, and build clarity where there is none.

In my own experience, the biggest product wins I’ve led—entering new markets, developing net-new products, or scoping acquisition opportunities—didn’t happen because I had a decade of domain knowledge. They happened because I could ask better questions, figure out how to find the answers, spot patterns across industries and customer pain points, and learn faster than the environment was changing. I’ve seen that same superpower in the people I hire when I prioritize mindset over résumé. They punch above their weight because they’re wired for learning, not just doing.

The specialist might know all the right answers. The generalist is asking the questions no one else thought to ask.

In a world where AI gives every team access to expertise, your edge is no longer what you know. It’s how you think.

And there’s more. In addition to their ability to think strategically and operate in ambiguity, generalists bring something else: distance from the status quo. That distance is an asset. A critical one.

Too often, companies default to hiring based on industry experience, assuming it signals readiness. But when someone has spent the last 10 or 20 years hopping between similar roles in the same industry, they don’t just bring experience—they bring baggage. They bring assumptions, habits, and mental models that have calcified over time. Instead of asking new questions, they default to old answers.

Hiring from the same pond gets you the same fish. And if your market is stagnant or ripe for disruption, that’s the last thing you want. (Paradoxically, I find the most stagnant, ripe for disruption markets digging in their heels and demanding candidates from the same tired talent pool.)

Likewise, beware of roles and tenure as proxies for growth. Someone who’s spent 15 years in a narrow role—project manager, product owner, business analyst—might be deeply competent in that niche, but untested outside of it. Look instead for signs of growth and flexibility: role changes, step-function challenges, new domains, or company shifts every few years. Again, paradoxically, the companies with the "no job hoppers" mentality are the ones that need those mindsets the most.

Long tenure at a single company can pose the same issue. It often means a person has only operated within one cultural context, one business model, one customer profile, and one stack of operational assumptions. They've only been successful with one playbook, with one way of working. They may be great at navigating that environment, but not necessarily adaptable to yours. Or to the wildly changing future careening straight at us.

Generalists break that mold. Their careers tend to show range—different roles, industries, technologies, business models, customers, challenges. And that range translates into one of the most important traits a PM can have today: perspective.

They're not just adaptable or strategic. They're high-agency—able to drive outcomes without needing hand-holding, structure, or perfect clarity. You're looking for PMs who are both self-directed explorers and intentional system thinkers. That’s the combination that lets them thrive in those critical situations where most others stall.

Of course, none of these signals—long tenure, niche roles, or deep industry experience—should be treated as automatic disqualifiers. They're yellow flags, not red ones. What matters is the context around them. Did the person show upward growth or seek out new challenges? Did they evolve within their role or company? Were they agents of change or guardians of the status quo? These are the questions that matter more than any single line item on a résumé.

This is just the beginning. If we want to build product teams that can thrive in the age of AI—not just operate, but lead—we need to get serious about how we identify and hire these adaptable, high agency, irreplaceable systems thinkers. Because they’re not always the ones with the longest résumés, the flashiest credentials, or the exact keyword match. But they are the ones who will shape the future.

That’s all for now. In Part 2, we’ll shift from mindset to mechanics—how to spot these high-agency, strategic generalists before they ever step into the interview.

Until next time, keep building boldly—and keep being irreplaceable.

In the next four parts of this series, we’ll get specific:

Part 2: Spotting High-Agency Talent Before the Interview
How to read between the lines of résumés and LinkedIn profiles to spot the signals of strategic generalists—and filter out false positives.

Part 3: Attracting the Right PMs (and Repelling the Wrong Ones)
Why your job post is probably targeting the wrong person—and how to rewrite it to appeal to high-agency, strategic thinkers.

Part 4: Interviewing for the Intangibles
The questions, signals, and frameworks that help you surface creativity, critical thinking, systems-level reasoning, and growth mindset.

Part 5: Developing and Retaining Irreplaceable Talent
Once you’ve got them, how do you keep them? Create an environment that keeps generalists engaged, challenged, and evolving.