So You Want to Hire a Digital Project Manager

Time consuming. Frustrating. It’s kind of a drag.

Close-up image of a woman's hands holding a job application package for a telephone company.

Hiring people when you work at a smallish company: always time consuming, often frustrating, generally ill-defined. It's kind of a drag. And yet the outcome holds so much promise—a stronger team, more time to focus on priorities, an influx of other-ways-of-doing-things that helps inoculate your work culture against stagnation.

This is no small decision that you're about to make. Not only are you about to alter the fabric of your organization, you're about to change the course of someone's life.

As if that isn't enough pressure, I believe that hiring a digital project manager for agency work is especially difficult because DPMs generally need to weave together a broad range of perspectives and expectations from technical people, artistic people, business people, and clients. These skills can't be learned from a certification process. When looking for a digital project manager, I'm hiring for temperament.

The process

There are no short cuts, and no matter how carefully we craft our ranking spreadsheets and Kanban boards, the hiring process will never be objective. Don't be fooled by the promise of automated, "bias-free", AI-enabled hiring—it's modern-day phrenology. Hiring people is—and should be—hard work, and if all goes well, the potential payoff is so much more than the sum of its parts. Despite the challenges, hiring a DPM is like any other project: first figure out what success looks like, then figure out how to get there.

Defining success can be tricky. Aside from the basic table stakes required to work productively as a DPM in an agency environment—client-facing experience, professionalism, attention to detail—for me, success looks like finding candidates who are:

  • Engaging communicators. Candidates should be able to tell a concise narrative about their career and how life led them to applying for this job. Real life is messy, but a good PM must be able to extract a cohesive story from a jumble of facts.
  • Competent negotiators. Everyone wants something from a PM—time, people, flexibility, favours. Candidates should have experience standing their ground while working toward a win-win outcome.
  • Humble. We all make mistakes. We don't always have the right answers. We all get nervous sometimes. It's more effective to acknowledge awkwardness directly and with humility than to willfully ignore an elephant that just walked into the room.
  • Curious. Successful DPMs are part-time students, part-time sleuths, part-time journalists, and part-time social scientists.
  • Kind. Because I just finished watching season one of The Mandalorian, I now believe there are two kinds of PMs—those who immediately try to assert their primacy when stepping into the cantina, and those who understand the difference between aggression and strength. Aggressive PMs are toxic and fizzle out fast. Strong PMs understand the power of kindness, which engenders trust and yields great work over the long term.

Your list might be different than mine, but defining the broad intangibles you're most interested in shines a light on the kind of filter you should be using in your deliberations while you review resumes and speak with candidates.

The resume review

Does an applicant's resume look like an exercise in keyword stuffing, or have they painted a clear picture of who they are and what they've achieved? Are their accomplishments grounded in enough context to mean something to you, or is it all "in my role at GeneriCorp I increased operational efficiency by 5000%". If an applicant for a project management position can't communicate an easy to follow, meaningful narrative about their own lived experience when employment is on the line, they're probably not going to meet your expectations when trying to communicate the nuances of project challenges to clients.

The one-on-one call

After shortlisting applicants at the resume review stage, I reach out to each individual to schedule a 20 minute, one-on-one call. My approach to these conversations is that if a basic human connection can't be formed over those 20 minutes, we're probably not a great match for each other. I usually start with some softball questions—tell me more about: your experience, a situation where you handled conflict, etc—but these are just ice breakers. If an applicant says something unexpected and interesting, I'll ask follow-up questions. There's a school of thought that says every candidate should be asked the same questions to standardize the evaluation process. But for me, and in the context of hiring a DPM, that produces a series of super-boring Q&A sessions that don't give applicants an opportunity to shine.

By facilitating a free(r)-flowing conversation, both sides can let their guard down (at least a bit) to hopefully learn more about the human on the other end of the line—their motivations, their aspirations, what they feel is important to bring up in this moment. It makes room for unexpected and interesting things to happen, and hopefully they will. A conversational approach can be an effective way to get insight into a candidate's comfort with communication, negotiation, kindness, curiosity, and humility (or whatever's on your list), and to get a sense of whether or not you think your organization will be the right move for this person.

The team interview

I wish I could say that if a candidate scores at least 7.3 on the kindness-o-scope they'll be selected for a team interview. But your decision about who you'll speak with at this stage will come down to your instincts and the type of position you're hiring for—a seasoned leader who will shape your organization from a high-level, a strong tactician with new (to you) ideas, a junior-level PM who's hungry for experience, etc. From the one-on-one interview, can this person communicate well? Does it seem like they could negotiate effectively? From the stories they tell, do they seem kind, curious, humble? Do you think they'd add a new perspective to the work your organization performs?

The team interview is your chance to fill in the blanks and gauge whether the person you spoke with earlier matches up with the person who's sitting in front of you now. Bring in at least two other colleagues for the team interview to get their perspectives and to see how the candidate communicates with them—does the candidate address everyone in your group equally? Is the candidate exhibiting the same qualities that piqued your interest in the one-on-one? If not, why might that be?

After the interview, does your team think the candidate meets the definition of success that you mapped out at the start? If you're not sure, this doesn't have to be the end of the road. Everyone has off days. If it's not clear whether a candidate should be selected or not, why not reach out to them to meet up for an informal (remote) chat and discuss the position further over coffee?

The final cut

I admit that the process I've laid out in this post is vague and entirely subjective. I don't believe the process of hiring a DPM can be fully quantified. After all, it's a very human process—messy, biased, and unpredictable. And I believe that's what drives our desire to control it. We're afraid of the unknown and of making a mistake. Based on the incomplete and probably inaccurate data that we have, how do we know that we're making the right decision to hire someone (or not)?

We don't.

In this moment, before you make a hiring decision, you can never be entirely free of unknowns. And, in a way, it's freeing to understand that the unknowns can never be eliminated. No one knows more than you about the candidates you've reviewed. There is no one more expert in this moment that can make a better decision than you based on the information you've collected.

You might end up rejecting an excellent DPM. That's ok. Stay connected with your standout candidates on LinkedIn in case an opportunity to work together presents itself in the future.

You might hire someone who ends up not working out. That's ok, too. Talk to your colleagues about it and learn as much as you can from that experience.

What matters most throughout this ambiguous, human journey toward hiring a digital project manager, is that you don't forget your own humanity along the way.