Experience Isn’t Everything: The Hidden Risks of Hiring ‘Been There, Done That’ Project Managers

In many ads for Project Managers, there’s a request for someone who has "done it before." Whether it’s implementing a particular ERP system in a specific industry, moving a system to the cloud, or leading a large-scale transformation, the demand is often for someone with that particular experience under their belt. The more experience, the better. But when did the "topic" become more important than project management skill? Why do people focus on this, and what are the risks of this approach?

Why ask for someone who has done it before

Hiring a Project Manager to run your project is inherently risky, and it’s sensible to minimize that risk.

Buying a service is hard. As the buyer, what you’re purchasing is invisible. If I’m buying a new TV, I can see it, touch it, try it out. But if I’m buying a Project Manager, I can’t see the service they will deliver. How do I know it’s what I need? Credibility becomes a key factor in reducing the risk. Hiring someone who has delivered the exact same service before adds to their credibility. The buyer looks for visible clues to mitigate the risk of the invisible. Asking for someone who has "done it before" makes sense.

Except sometimes, it doesn’t.

The reality

Let me share an example from my own experience.

I have run technology modernization programs before. These are complex, challenging, long-running projects. This is something I have experience with—something I have done before. And having managed this type of work, I’ve learned lessons that will certainly help me and make me more effective if I were to lead a similar program again. But here’s the kicker: I can share those lessons with other organizations on a modernization journey in just an hour, using a dozen slides.

The benefit of having "done it before" can be shared in 12 slides, in one hour.

The risk

While hiring someone who has "done it before" may seem like a way to de-risk your project, there are also significant risks that must be mitigated.

• Have you ever driven to work and arrived without remembering the journey? You were on autopilot. That’s why, when a road layout changes, there are signs everywhere warning you. We go into autopilot and can miss important details unless someone alerts us. The same is true on projects. It’s easier to miss nuances and new warnings when I’m simply following a "tried and tested" formula that worked for me last time. That adds risk to your project.

• "Done it before" is not the same as "done it here before." No two places are the same. Your company’s culture and ways of working are different—what if the approach used before doesn’t align with how you do things? The value you seek from the project is likely different. This may not just be a "move to the cloud" project. It could be a "remove technology risk" project, a "reduce technology operating costs" project, or a "reduce operational headcount" project. All of these involve moving workloads to the cloud, but each requires a different approach based on the specific outcome. If you’ve asked for "what" experience instead of "why" experience, don’t be surprised if the result doesn’t deliver the outcome you need.

• Finally, "done it before" doesn’t mean "done it well before." The outcome might have been achieved, but the road to that outcome could have been rocky and difficult. You can’t rely solely on the "done it before" criterion. You still need to evaluate credibility across other dimensions, not just this one.

What to look for instead

I’m not saying that all Project Managers who have "done it before" are bad or that you should avoid them—far from it. But I advocate for a broader view in your search, which could lead to better results for you and your project.

• Look for someone who fits your culture and ways of working.

• Look for someone whose quality of work can be validated through your network, referrals, or references.

• Look for someone who understands the outcome you’re trying to achieve, not just someone who has walked a similar path in the past.

• Look for someone with deep project management skill. If I drive the same racetrack 1,000 times and then race against Lewis Hamilton, who has never driven it before, he’ll still beat me. Skill can trump experience.

• Look for someone you connect with and get along with. You’ll be in the trenches together for a while, and you want to enjoy the experience.

Someone who has "done it before" may have a small advantage over other candidates, but don’t focus on this exclusively at the expense of other important criteria.