What Makes A Good Head Of Talent—Beyond "People Skills"

Talent is the lifeblood of your startup.

Put aside funding, market conditions, and business models—if you don't have the right people working on the right problems, you will fail. This makes talent acquisition one of the most critical functions of your business, and by extension, makes your talent department the core of your success.

Put more simply, to build a world-class company, you have to build a world-class talent team, starting with your first hire: your head of talent.

Some founders will disagree with hiring a department head before building the department. They believe you should build your team from the bottom up, hiring recruiters before bringing on managers. This approach is appealing because it's fast and emphasizes immediate results. Some founders even refer to it as building a “hiring MVP" (minimum viable product).

The truth is, the way you hire in the early days of your company—delegating hiring to a team member or job-sharing it across your company—is your hiring MVP. To grow, you need to take that MVP and build it out into a scalable, powerful solution. To pull it off, you're going to need a team, and to build that team, you need a leader.

In this guide, we're going to profile the three key attributes of your future head of talent. You should be able to describe the right person as:

1. A Process-Oriented Architect

Momentum is one of your biggest assets. Your head of talent's job is to design processes that sustain that momentum without letting the train run off the tracks. For a person to take on that responsibility and succeed, they need to have experience building things from the ground up.

Your head of talent's experience as a process-driven builder, however, doesn't necessarily have to be gained through recruiting. Based on an analysis of our AngelList data, we found nearly 50% of people leading talent departments were not working in recruiting immediately before leading their first talent team:

Previous Roles of Talent Leads By %

Source: AngelList Data

Often, these people worked in process-oriented roles, like operations, HR, consulting, or even as founders. If the person shows passion and intelligence for leading your talent team, and they have a track record of process excellence, they're worth considering.

At the same time, this process-inclination needs to be balanced with a “get results now” mindset. Otherwise, growth will stall. Chris Middlemass, director of talent at user-centric ad network Gladly, described the dangers of prescribing process for process' sake:

“If you put too much structure in place, you'll get resistance from the team. (You also) can't work as nimbly, and things are not going to be done as quickly. Make sure structure is added where it's needed, but that you don't over-structure and over-organize things.”

Your head of talent needs to be able to balance their process expertise with your startup's need for agility.

To Test For Process Excellence, Consider Asking:

“If we needed you to hire five engineers in the next thirty days, explain to me how you would approach the problem.”

The goal here isn't to discover a hiring growth hack, it's to see how they think. What you want to see is if they naturally dissect bigger problems into smaller processes. A great answer would begin by asking you for more context—what systems are already in place, what resources they have access to, etc.—and would then attempt to break the engineer hiring funnel into pieces, suggesting processes that will move you toward the hiring goal.

2. A High-Level Business Strategist

Talent sits at the intersection of every department, every goal, and every strategic decision a company makes. Your head of talent, as a result, needs to be able to make decisions that take into account a variety of factors—your business model, the personalities of different stakeholders, and your current financial state, to name a few.

Keith Rabois, executive at PayPal, Square, and Opendoor, has a simple way of evaluating someone's ability to think at this level. He invites them to ask him any question at all about his business. If a candidate's questions get at something fundamental—something Rabois and his team grapple with themselves—then he knows they likely have that ability.

A great example of a talent-specific question would be one around attrition. As Brenley Brotman, senior director of global recruiting at mobile security startup Lookout, told us:

“Startups have 25% to 30% attrition minimum per year. So, if they want to grow at 10% to 20% to 25%, they have to bolt on another 25% for attrition... That's why recruiting generally misses their metrics. Leadership isn't thinking about attrition and how that factors in to the overall demand gen of the recruiting function.”

To Test For Strategic Thinking, Consider Asking:

“Pretend we hired you as a consultant to evaluate our talent function. What questions would you ask?”

If a candidate asks you a question about attrition, or another metric that shows they're thinking about recruiting in the greater financial context of your business, that's a good sign.

3. A Strong-Willed, But Collaborative, Owner

A head of talent, especially in the early days, will likely recommend changes that could cause friction among company stakeholders. The ability to act like an owner and advocate for ideas is crucial to this person's success.

Brandon Sligh, recruiting lead at digital trust platform Sift Science, described this particular challenge. Shortly after joining Sift Science, he noticed the company's phonecalls to screen engineering candidates worked well for junior hires, but converted poorly for more senior roles. It was a huge problem, as hiring senior engineers is a key priority for many talent departments.

Sligh's working theory was Sift Science's interview process overly-optimized for junior candidates, making it harder to attract more senior engineers. “This was something that was not easy to prove," he says. "It was not believed initially by our head of engineering or our CTO.”

So Sligh surveyed senior candidates who had turned Sift Science down to find out why. It turned out, their phone screens relied heavily on technical questions better suited for someone fresh out of college. “Senior engineers just aren't going to have them memorized anymore,” Sligh says.

So he pushed for a new screening process that included questions more senior candidates could engage with. Since then, Sift Science has more than doubled its conversion rate with senior engineers.

This improvement was only possible because Sligh had both the ability to analyze the startup's inner workings and the tenacity to go back its stakeholders with the data that proved it, again and again, until they were bought in.

To Test For An Owner's Mindset, Consider Asking:

“Tell me about a time you convinced your team members to buy into an idea they were initially resistant to.”

What you're looking for here is a firm but mindful approach. A great answer will show that the person didn't immediately wilt in the face of disagreement; instead, they pushed their team in a collaborative way.

Don't Expect Overnight Results

The person described above is someone who will collect data, set goals, and design processes to achieve them. This will take time.

Spencer Hoffman, head of recruitment at education startup ClassDojo, recommends that a new head of talent spend “100% of your time for the first two-to-four weeks on really understanding what's going on.” Hoffman spent his first couple weeks at ClassDojo manually reviewing every offer the company had ever made to analyze trends in its hiring.

You want a head of talent who takes the time to understand your business that thoroughly before they design the department that will ultimately hire the rest of your talent. As hard as it can be to move slowly when your startup is in a rapid growth phase, you have to give your new head of talent at least three months before you can truly evaluate whether or not the person has been successful.

This ramp-up period is another important reason to hire your head of talent first. Operating in the reverse order—bringing on recruiters on an as-need basis, until you reach critical mass and desperately need someone to lead the department—is like hiring someone to build you a plane moments before take off. Things are going to be chaotic, stressful, and most likely end in a crash.

Avoid it by hiring your head of talent sooner, rather than later.

More Hiring Questions?

Have more questions about hiring? Check out some of our other guides:

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