How Do You Screen for Scrappiness?
My wife and I are both actively involved in interviewing candidates, and one of our favorite post-interview rituals is debriefing the trends we’re noticing. Were they memorable? Did they feel overly buttoned up? Did they rely too heavily on “strategy” talk—throwing around frameworks, systems, and impressive jargon—without really showing us what they’re capable of? Were they lost in marginal details, missing the forest for the trees?
All of this has had me thinking: how do you actually screen for scrappiness?
Scrappiness is tricky to define. It’s not just hustle. It’s not just resourcefulness. It’s something in between and beyond—a “builder’s mindset” that combines action with creativity. Yes, hustle and resourcefulness are ingredients in the scrappiness pie, but there’s a “mama’s secret sauce” element too—something harder to articulate but unmistakable when you see it.
Scrappy people have a bias for action. They carry a curious, kinetic energy. They communicate creatively and move with purpose. You can describe these traits, but there’s often a magic in the moment when a scrappy person takes hold of a problem and just makes something happen.
Here are a few examples that help me distinguish between someone who's scrappy vs. someone who's just strategically polished:
GETTING THEIR ATTENTION
Me: Talk to me about how you’d target our top net-new accounts.
Strategic (Yawn) Response:
“If I joined the team, I’d account map, identify key stakeholders, and begin building an outreach execution plan.”
Scrappy (Smile) Response:
“I already looked at a few companies I don’t think you’re working with today. I sent personalized notes to VP-level execs about how your company is changing the mobility landscape and why they should know about you. If I join Metropolis, I’ll follow up, let them know I’ve come aboard, and tell them they’re one of the first accounts our leadership asked me to pursue. I’ll layer in warm intros from the company network, but I’ll never wait to get started—I’ll build momentum from day one.”
NAVIGATING CHALLENGING SALES
Me: What’s one deal you’re most proud of, and how did you execute it?
Strategic Response:
“We engaged stakeholders across the org, built a cross-functional team to address concerns, negotiated over nine months, and ultimately closed the deal.”
Scrappy Response:
“The client wasn’t originally interested. I gained their trust, convinced them to take another look, and flew them to Boston to tour a similar operation. We even got some of our top customers to send personal notes. During negotiation, we structured the deal so they felt they’d won some serious concessions. But it was worth it—we’ll over-deliver and use this as a springboard to expand.”
CREATIVE COMMUNICATOR
Me: Why you?
Traditional Response:
“I thrive in complex environments. I’ve led enterprise sales motions, built strategic partnerships, and consistently exceeded my goals. I’m confident I can create and execute the strategy to help us succeed.”
Scrappy Response:
“I obsess over winning. I want our prospects to wake up thinking about us. When a new partner enters the market or a seismic shift happens in the industry, I’ll make sure our customers know we’re the team to lead them through it. I won’t just build a strategy—I’ll make sure it gets done. Oh, and by the way, check your front door—I left you a Doordash. It’s a spongecake, so you’ll remember me.” 😄
SCRAPPINESS IS MEMORABLE
When I think about the people I’d call “scrappy,” a few traits always stand out:
They’re memorable. They leave a mark—usually a positive one. But they’re often polarizing. Some people love them. Some people don’t.
They’re accountable. They do what they say they’ll do. They might move fast and may make a few missteps, but their bias for action usually moves the ball forward.
They take calculated risks. And that’s the key. The biggest risk in life is taking no risks. Take too many and miss, and you’re buried. Take too few, and you’re stuck. But take just the right amount—and nail it? That’s where the magic happens.
Love the "yawn" and "smile" between parantheses!