I’ve made about a dozen hires over the last few years. Some for PipelineRoad, some for previous ventures, a few advisory hires for clients. That’s not a huge sample size. I’m not going to pretend I’ve cracked some universal hiring code.
But I’ve developed a set of instincts about what to look for — and what to ignore — that has served me well. And almost none of it has to do with resumes.
The Resume Problem
Let me get this out of the way: I read resumes. I don’t throw them out or make a show of ignoring them. They contain useful information — career trajectory, tenure patterns, the kinds of companies someone has worked at. These things matter.
But a resume is a marketing document. It’s the highlight reel. Nobody puts “managed a project that went sideways because I couldn’t prioritize” on their LinkedIn. So while I read resumes, I hold them loosely. They tell me what someone did. They tell me almost nothing about how they think.
The best hire I ever made had a resume that would have been filtered out by most ATS systems. No degree from a name-brand school. Job titles that didn’t map cleanly to the role I was filling. A two-year gap that turned out to be time spent traveling through Central and South America, during which she’d taught herself to code, started a small freelance business, and learned conversational Spanish and Portuguese.
The worst hire I ever made had a perfect resume. Blue-chip companies, progressive titles, all the right keywords. He interviewed beautifully. He also turned out to be someone who could articulate strategy brilliantly and execute almost none of it.
Resumes measure credentials. I’m looking for something else entirely.
Curiosity Over Credentials
The single trait I weight most heavily is curiosity. Not the “I’m a lifelong learner” kind that people put in their LinkedIn summary. Real curiosity — the kind that makes someone dig into a topic because they can’t help themselves.
I test for this in interviews by asking people what they’ve been reading, watching, or thinking about lately. Not professionally — just generally. I want to know what pulls their attention when nobody’s assigning them work.
The answers are revealing. Some people light up. They’ll tell you about a podcast episode that changed how they think about urban planning, or a rabbit hole they went down about the history of typography, or a side project they started because they wanted to understand how recommendation algorithms work.
Other people go blank. Or they give the “right” answer — some business book they think I want to hear about. That’s not a disqualifier, but it’s a signal.
Curious people learn faster. They make unexpected connections between domains. They ask better questions. They’re less likely to get stuck because they genuinely enjoy the process of figuring things out. In a small agency where everyone needs to wear multiple hats, curiosity is the closest thing to a universal skill.
Writing as a Proxy
I ask every candidate to write something as part of the hiring process. Not a formal writing test — just a short piece. Sometimes I give a prompt. Sometimes I ask them to send me something they’ve already written that they’re proud of.
I’m not hiring for a writing role (usually). But writing ability is the best proxy I’ve found for clear thinking. If someone can take a complex idea and communicate it simply, in writing, they can probably do the same thing in a client meeting, a strategy document, or a Slack message at 9 PM when something’s on fire.
Bad writing — and I mean structurally bad, not grammatically imperfect — usually indicates muddled thinking. Long, meandering paragraphs that never arrive at a point. Jargon used as a substitute for specificity. Passive voice everywhere, which often signals someone who doesn’t want to commit to a position.
I’ve hired people whose writing was rough but clear over people whose writing was polished but empty. The rough-but-clear writer can improve with editing. The polished-but-empty writer has a thinking problem, not a writing problem. That’s much harder to fix.
The Travel Instinct
I travel a lot. Forty-plus countries at this point. And one of the things extensive travel teaches you is how to read people quickly — across cultures, across languages, across contexts where your normal social cues don’t apply.
In a hostel in Vietnam, you learn to assess a stranger’s character within minutes. Not because you’re paranoid, but because you’re making practical decisions: is this person reliable enough to split a taxi with? Interesting enough to spend a day exploring with? Trustworthy enough to watch your bag?
These micro-assessments train a muscle that translates directly to hiring. I pay attention to how candidates behave in unstructured moments — the small talk before the interview starts, the way they interact with other people in the room, what they do when I deliberately leave a silence in the conversation.
Do they fill the silence with nervous chatter, or are they comfortable sitting in it? Do they ask me questions, or do they only answer mine? When I say something they disagree with, do they push back, or do they nod along?
I’m not looking for a specific behavior. I’m looking for authenticity. People who are performing a version of themselves are usually easy to spot if you’re paying attention. People who are genuinely themselves — with all the imperfections that implies — tend to be the ones who thrive in the messy reality of agency work.
Cultural Add, Not Cultural Fit
I stopped using the phrase “cultural fit” a few years ago. Not because the concept is wrong, but because it’s been co-opted to mean “someone who looks and thinks like us.” That’s how you build a team that’s comfortable and mediocre.
I think about “cultural add” instead. What does this person bring that we don’t already have? A different perspective, a different background, a different way of approaching problems?
At PipelineRoad, our team spans multiple countries. Bruno is Brazilian. Alfredo brings a European sensibility. Andre and Mikael each have their own creative orientations. The diversity isn’t performative — it’s practical. When you’re marketing to different audiences in different industries, having a team that only sees the world one way is a liability.
So when I’m evaluating a candidate, I’m not asking “will they fit in?” I’m asking “will they expand what we’re capable of?” That’s a fundamentally different question, and it leads to fundamentally different hiring decisions.
Red Flags I’ve Learned to Trust
A few things that consistently predict a bad hire, in my experience:
Blame patterns. When someone describes past failures, listen to the pronouns. If every failure was someone else’s fault — the company, the manager, the market — that’s a red flag. I want people who can say “I made this mistake, here’s what I learned” without flinching.
Over-optimization for title and compensation. People who lead with “what’s the growth path to VP?” in the first interview are usually more interested in the packaging than the work. I’ve had great hires who never once asked about their title.
Inability to say “I don’t know.” In interviews, I sometimes ask questions that are genuinely hard or outside the candidate’s expertise. The best candidates say “I don’t know, but here’s how I’d figure it out.” The worst candidates bluff. Bluffing in an interview is a preview of bluffing in front of a client.
Perfect polish. This sounds counterintuitive, but candidates who are too smooth — too rehearsed, too polished, too perfectly on-message — make me nervous. Real competence has rough edges. People who are genuinely good at what they do can talk about it naturally, including the parts that didn’t work.
Green Flags That Get Me Excited
Side projects. Someone who’s built something on their own — a blog, a small app, a community, a creative project — has demonstrated initiative, follow-through, and the ability to work without external structure. Those three things are gold in a small team.
Thoughtful questions. When a candidate asks me something that shows they’ve actually thought about our business — not a generic “what’s your company culture like?” but something specific and incisive — I take notice. Good questions reveal good thinking.
Comfort with ambiguity. Agency work is inherently messy. Client needs change. Strategies evolve. Someone who needs perfect clarity before they can start working will struggle. Someone who can say “here’s what I think we should do given what we know, and I’ll adjust as we learn more” — that’s who I want.
Genuine enthusiasm for craft. Not enthusiasm for the industry or the company specifically — enthusiasm for doing their particular thing well. A designer who geeks out about type spacing. A strategist who gets excited about competitive analysis. A writer who cares about sentence rhythm. People who love their craft don’t need to be managed toward quality. They get there on their own.
The Decision
At the end of every hiring process, I ask myself one question: would I want to be stuck in an airport with this person for six hours?
It sounds frivolous. It’s not. An airport delay strips away all the professional veneer. You find out if someone is interesting, adaptable, good-humored, and capable of genuine conversation. Those are the same qualities that matter when a client deliverable falls apart at 4 PM on a Friday and the whole team needs to rally.
Hiring is ultimately a bet on a person. Not their resume, not their references, not their carefully prepared case study. A bet on who they are when the structure falls away and they have to operate as themselves.
I’ve gotten better at reading that over time. Travel helped. Experience helped. But mostly, I just learned to pay attention to the things that credentials were designed to distract from.