Back when I owned Bobsled (the retail media agency that I sold in 2022), I got an email from the owner of a competing agency asking for an urgent call about an "HR matter." Since most of us agency owners were on friendly terms, I quickly scheduled a call with him and Bobsled's president, Julie Spear.

The bombshell: two star employees we had recently hired were simultaneously working full-time for my competitor. Julie and I were shocked. These weren't struggling junior staffers moonlighting for extra cash—these were star performers we'd hired after rigorous interviews, people producing excellent work that clients praised.

The cognitive dissonance was jarring. How had we missed this? More importantly, how had they managed to perform so well while essentially working two full-time jobs?

The experience planted a question that's only grown more relevant in today's AI-enhanced hiring landscape: How do you spot someone who's just really good at appearing competent versus someone who genuinely knows their stuff?

This isn't just theoretical anymore. Last week, a Retail Media Breakfast Club fan wrote in asking exactly this: "How do you spot someone who's a real expert versus someone who's, well, totally full of it?"

In a world where candidates can use AI tools to craft perfect responses, where "digital twins" can show up for interviews, and where even recruiters are asking candidates to wave their hands across their faces mid-Zoom call to prove they're not AI avatars, distinguishing authentic expertise from well-crafted imitation has never been more challenging.

I reached out to several agency-side retail media leaders who've developed their own techniques for separating the imposters from the experts. Agency-side, because these are the people who see the most volume of candidates, and their subsequent wins and misses.

The "One-Trick Pony" Problem

Ross Walker, Director of Retail Media at Acadia, has faced similar challenges identifying authentic expertise during the hiring process. In his experience, some of the trickiest cases aren't obvious underperformers, but rather candidates who present well in interviews before revealing their limitations on the job.

Ross has encountered people who sail through interviews with polished answers and all the right buzzwords, only to show limited capabilities once hired.

As Ross explains, "The cracks start to show when those one or two good ideas are exhausted and they've got nothing else in the tank. Or maybe worse, their long-term people management skills, communication, or relationship-building abilities are really lacking."

Ross has identified two common patterns in his experience:

First, there's what we might call the knowledge poacher. As Ross puts it, "I've had people come from other agencies who stayed for a short time, and in hindsight, it seemed like they came to get a crash course in our methodology or media approach before skipping to another agency with a better title." These candidates use job-hopping as a way to collect expertise without building it.

Then there's the shallow strategist. In Ross's words, "I've had people execute one plan well, but as soon as the client starts asking questions or they face challenges outside their immediate sphere of influence, they freeze up." These candidates lack the strategic depth and adaptability needed in retail media's constantly evolving landscape.

Ross's solution? Internal promotion whenever possible. "Starting with people early in their careers who are still hungry to learn...they fail at a level that's totally acceptable and grow more organically. A lot of our best hires have been with us for many years and grown into senior positions over time."

The Structured Approach to Interviewing

Mike Feldman, SVP and Global Head of Retail Media at VaynerMedia, brings a more systematic approach to spotting genuine talent.

Mike emphasizes situational interviews with specific structure. As he explains, "I am a big fan of situational interviews. I will often tell candidates I am going to ask more situational questions such as 'tell me about a time when' and that I am looking to see them answer in SBO format (Situation-Behavior-Outcome)."

Importantly, Mike notes that he's evaluating "more about their thought process and approach vs. the actual answer or example itself." This focus on how candidates think rather than the specific examples they share helps reveal authentic expertise.

Mike also is insistent on 'purposeful' interview panels. "I think interview panels are essential to get a rounded perspective but it's important to give everyone an assigned role," he explains. "For example, I would likely have someone access technical skills, another look at virtue/personal values fit for the organization, another to assess soft skills, etc."

Critically, he points out that "what's even more important is to have a calibration session with all interview panelists to compare notes." This collaborative approach helps catch discrepancies that might not be apparent to a single interviewer.

Mike also relies heavily on his professional network. "Working your network is essential," he says. "We work in an incredibly small world and if I have candidates that have been around the industry for a few years I will often check with people that have worked with them before."

He shares a telling example: "I have a very vivid example in my mind where I had a candidate that soared through the interview process and everyone loved them. I had asked a trusted colleague from another organization and they said they had heard not good things about them and their work. I chalked it up as environment but when we hired the person it was clear very early that it wasn't working out (and for all the reasons I was warned about)."

Mike also highlighted a broader industry challenge that contributes to the imposter problem: "There's a shortage of retail media talent overall. With retail media growing 20% year-over-year for the last decade plus, there hasn't been the same level of education or talent development." This talent gap creates pressure to hire quickly, sometimes prioritizing filling roles over finding optimal fits.

Mike agrees with Ross Walker's conclusion that the best route is to grow talent internally. "In most cases, agencies have the most success continuing to bring in junior level talent, train them on retail media and elevate from there. Finding quality external retail media talent at mid levels is incredibly competitive and at senior levels is rare to find transcendent talent (think about how many focus areas retail media has so its hard to find talent that can lead across all fronts)."

A Defense of the Accused "Imposters"

Jordan Witmer, Managing Director - Retail Media & Consulting at Nectar First, offers a refreshingly different perspective, challenging the very notion of "imposters" in retail media:

"I've been talking about Retail Media for years, and I can count on one hand the amount of people I'd legitimately call imposters," Jordan states. Drawing on baseball terminology, he adds, "The loudest boos come from the cheapest seats. Ninety-nine percent of people in this industry are doing what they believe is the right thing with their experience and constraints."

Jordan suggests that many so-called imposters are simply specialists with limited perspective: "People can get flagged as 'imposters' when really they've only seen one side of the ecosystem." He points to various "archetypes" that he has identified in retail media—like "The Amazon Truther" whose experience was shaped during Amazon's heyday when organic growth of 20-100% was common regardless of strategy, making them skeptical of other retail platforms. (I hope that Jordan shares these archetypes one day in his excellent monthly newsletter on LinkedIn!)

His practical advice? "Do your homework on someone's background—do they have the experience to back up what they're saying, and are they the right person to teach you what you're trying to learn?"

Recapping the Advice

Looking across these perspectives, several actionable strategies emerge for identifying genuine retail media expertise:

1. Look for learning agility, not just domain knowledge. The retail media landscape evolves too quickly for static expertise to remain relevant.
2. Implement structured interviews that reveal thought processes rather than just rehearsed answers.
3. Verify through networks, but be aware that even this approach has limitations.
4. Evaluate candidates' ability to see multiple perspectives rather than dogmatically pushing a single solution.
5. Consider development pathways for promising talent rather than expecting to hire fully-formed experts.

I still think back to those 2 employees and wonder what became of them. How long did they continue their moonlighting? Did they move on to deceive other companies, or did they eventually get caught elsewhere too? (By the way, "Overemployed" is the term for this practice – there's even a subreddit dedicated to it that will put any hiring manager on edge.)

Their ability to maintain two full-time jobs simultaneously while delivering quality work raises uncomfortable questions about work expectations, time management, and the metrics we use to evaluate performance. Were they exceptionally talented, allowing them to complete in 20 hours what takes others 40? Or were they cutting corners in ways we never detected, leaving landmines that would eventually explode after they left?

In the end, there's no perfect formula for identifying authentic expertise. Sometimes you hire someone who seems perfect only to discover they're working a second full-time job. Other times, the person who doesn't check all the boxes turns out to be your most valuable team member.

The challenge for hiring managers is distinguishing between candidates who can grow beyond their current limitations and those who are skilled primarily at creating the appearance of expertise.

The AI revolution has only made this more complicated. Today's tools can help candidates craft perfect responses or even create digital doppelgängers for interviews. But they can't replicate the flexible, adaptive thinking that defines true expertise — at least not yet.

Until then, maybe we need a metaphorical "wave your hand across your face" test for expertise: creating interview situations that reveal not just what candidates know, but how they approach what they don't know. Because in retail media's constantly evolving landscape, how you learn often matters more than what you've already learned.

The best we can do is combine rigorous assessment with a willingness to trust our instincts. And remember that in this industry, everyone is learning as they go.