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This Tech CEO’s Top Two Tips For Hiring A Great Leadership Team

Thumbtack cofounder Marco Zappacosta has hired leaders from Google, YouTube, and Bain. Here’s how that taught him to rethink the executive search.

This Tech CEO’s Top Two Tips For Hiring A Great Leadership Team
[Photo: U.S. Air Force photo/Senior Airman Jason Couillard]

Marco Zappacosta launched Thumbtack after graduating from college in 2008. Like most first-time founders, he wanted to reinvent everything. Since then, Zappacosta’s company has changed how consumers connect to local professionals, with millions of projects completed across the U.S.

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One of his proudest accomplishments, however, was not an innovation, but a realization–one that took nine years to fulfill. “We’ve recruited heads of engineering, product, marketplace, finance, HR, operations, marketing, and general counsel. For the first time in our history, we’ve filled all the seats. They’re incredible in their own ways and work well together,” says Zappacosta. “It took a bit, but I’ve learned to leave reinvention to our product, not its guardians. I’ve realized how immensely valuable it is to have an experienced executive team.”

Senior engineering director at Google. Director of product management at YouTube. Principal at Bain. When Zappacosta looks at the pedigree of his executive team members, they’re both impressive and far more senior in their careers than he is. For first-time and early-stage founders like Zappacosta, it can be daunting to recruit and hire such high-caliber executives, especially when you don’t have enough knowledge to test for skill level in their areas of expertise. As a result, Zappacosta notes that “hiring execs is extremely high beta. When it goes well, it can be an enormous force multiplier, accelerating your company in ways that you won’t appreciate right away. The flip is that a high-upside hire is also a high-stakes hire. It can take four quarters before you can really know if it’s going to work out.”

With that in mind, the Thumbtack CEO shares two of his best tips for identifying and vetting C-level leaders, from job descriptions to the interview stage.

1. Rein In Your Job Descriptions

A big mistake Zappacosta sees with with exec searches are the extensive job descriptions (or “JDs” for short). “How many times have you seen a JD that defines the position by listing a dozen different skills?” he asks.

“Don’t describe the entire position in exquisite form, even though all those skills may be useful. That laundry list of requirements won’t exist in a human,” Zappacosta says. “Invariably, you end up with someone who’s mediocre at all of them, but not exceptional at the ones at which you truly need them to be exceptional. You hire for lack of weakness rather than for an explicit strength.”

At Thumbtack, hiring plans–from executives to entry-level hires–are focused around identifying and evaluating the three most essential skills to the role. “That practice forces a few things,” Zappacosta explains. “First, a hiring manager must think more critically about what she needs at that juncture on her team. Second, it keeps her from optimizing for every desirable attribute,” he says.

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“So for an executive, here’s how this might look in practice as a summary: ‘This role will be expected to grow the team from 20 to 200–so they must spike high on team building, recruiting, and mentorship.’ That may mean that they’re less technically deep in another domain. But we can live with that. And we’ll solve for it by hiring other great people.”

This level of focus also serves the reference-check process. “Instead of saying, ‘Hey, tell me about this person and what they’re good at,’ you can orient it strictly around the attributes you’re evaluating,” says Zappacosta. “The line of questioning becomes more specific: ‘Hey, I’m looking for a team builder. I’m trying to find someone who could help us grow from 20 to 200. Can you talk to me about what you saw in her as a team builder?’ This elicits more concrete, targeted feedback.”

2. Interview Separately For Skills And Fit

After a recruiter does an initial screen for those specific attributes, the candidate is introduced to Zappacosta. Here he’s also made some changes to the executive-search process in order to make it more productive–which starts by splitting what is typically one interview with the candidate into two sessions.

“The first conversation is just to get to know the person,” Zappacosta explains. “The candidate typically has lots of questions about us, and she’s asking me many questions about Thumbtack and me. There’s ‘selling’ both directions to see if there’s interest,” he says. “The second conversation tends to be more substantive. We start to unpack some of the experiences they’ve had. We get down to brass tacks on the position, including its challenges and opportunities.”

Interview questions for that first meeting are more specific to the company, the role, and the candidate, so those are more general informational sessions to get a lay of the land. But Zappacosta has tested out a number of questions to get at “fit” during the second interview. “I take a broad view of fit. It certainly means aligning on values–but also on ambition, how they like to work, how they view leadership and building teams,” says Zappacosta. Here are a few interview techniques and questions Zappacosta has used to evaluate executive candidates.

Name the job that comes after this job. “A big one is ambition. How ambitious are they–and does that ambition map to that of the business? You need to know how that will connect with your personal ambition and what the company can offer,” says Zappacosta. “Ask candidates, ‘What do you want to have happen to the business?’ If the candidate’s ambition is to sell to Google and mine is to go public, then we’ll be at loggerheads at some point–and in tension until then. It’s not about one person being right or wrong, but having two futures of the company,” he continues. “Plus, execs recognize that the reality is that it’s not going to be the only job they ever have. So you want to know how this factors into the career that they’re building toward.”

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Find the invisible hand. “It’s critical to know what drives people. Some execs are motivated by money. Others by impact. Or the desire to lead high-performance teams,” says Zappacosta. “If you ask someone what motivates them, you get spoon-fed a pat answer. Ask, ‘What accomplishment are you most proud of in your career?’ Answers to this question surface value systems. I might hear: ‘We had this huge stretch revenue goal. Nobody thought we’d hit it–and we did hit it.’ But I’d rather hear, ‘We were given this tough challenge. I rallied this team. We worked super hard. It actually failed, but we all looked back on it as an inspiring and motivating time.’ Again, one of these is not right or wrong,” he says, “but it shows me a source of pride.”

Show me a “worst.” “Anybody who has worked for decades has failed immensely at some point. And if they haven’t, I wonder: Have you been through enough? Or are you not willing to be raw with me? Or are you not self-aware? It’s typically not a good sign if they can’t talk about big missteps,” says Zappacosta. “Because talking about failure gets into the question of how vulnerable they’re willing to be, and if they’ve had transformative, firsthand learning, which happens after mistakes. So ask, ‘What failure are you most proud of?’ I want to work with leaders who are willing to be vulnerable quickly.”

Finally, Zappacosta adds, this second interview is the one that carries more weight. As he puts it, “A misevaluation of fit, much more than talent, is usually the reason executive hires don’t work out.”


A version of this article originally appeared on First Round Review. It is adapted with permission.

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