10 Questions This Former Apple Recruiter Asks Before Hiring Leaders

Don’t immediately start combing LinkedIn for executive-level candidates. Here’s what one recruiting expert suggests doing instead.

10 Questions This Former Apple Recruiter Asks Before Hiring Leaders
[Photo: William Iven/Unsplash]

Jennifer Rettig became an expert at recruiting before LinkedIn existed. As anyone who’s gone searching for candidates recently knows, this is an unthinkable level of badassery. Just as Google made finding information any other way a bizarre notion, LinkedIn has done the same for recruiting. And while Rettig is of course a power user now, she brings the creativity, wit, and resourcefulness of someone who cut her teeth without it.


She started her recruiting career at Apple–first in retail and then marketing–where she was tasked with helping build the iPod product team when no such technology had ever existed. Since then, she’s deepened her expertise in executive searches at Yahoo and JCPenney (reuniting with famed Apple Store creator Ron Johnson), and has now joined business intelligence leader Looker as Head of Recruiting.

That’s all to say, Rettig has found candidates for every manner of role at every level of big, challenging organizations demanding nothing less than perfection. Now, she wants to share what she’s learned with the startup community–where executive hires can truly make or break a company’s fate. Her main thesis: You don’t have to shell out for costly recruiting agency help to find the right executives for you. Instead Rettig suggests, among other things, investing your time doing a different type of research–and go deep.

Answer These Questions Before Sourcing Talent

Doing research into the type of candidate you might want for an executive role sounds obvious, but Rettig suggests a deeper variety of investigation before you even get started sourcing.


If your company has a head of recruiting or recruiting team, they should do the research you need to both fully understand the role and the profile of people who would be successful in it. The recruiter with the most business acumen should lead the charge here. Many recruiters are good at transacting and closing deals but may not have full comprehension of the ins and outs of the business itself (this happens on larger teams). For executive searches, you need this level of understanding.

That’s not to say that only senior or heads of recruiting are right for the job. Driving and directing research can be a great developmental opportunity for more junior team members to learn and gain visibility with top leadership. In the past, Rettig has had a lot of success entrusting research to junior team members fresh out of school, because their skills are sharp. What’s required is more akin to academic research than straight sourcing. (If you don’t have a recruiting team, then once again, this falls to the hiring manager.)

So when there’s an executive opening, you need to ask more than, “Who’s right for this role?” First, the existing leadership team needs to ask and answer these initial questions together:

  1. Why are we adding this role?
  2. What direction do we hope this role will take the company?
  3. Why is it mission-critical for us at this moment in time?
  4. How will the person in this role interact with existing leadership?
  5. What does it mean to be a great X role? A great VP product, COO, general counsel etc.?
  6. What will their success look like in the first six months? The first year?
  7. Who are the people doing this job really well right now? Who is in the press?
  8. What companies do we admire? How have they done what they’ve done?
  9. What companies clearly have someone very talented in this role?
  10. What does the ideal candidate need to have done before in their career?

Get answers to these questions down on paper. They’ll give you an entry point into your search, what type of candidates you go after first, how you gain buy-in from stakeholders you’re asking for help, and how you set expectations with prospects.

“When you ask people on your team to think of the ideal candidate for a role, their mind will probably jump to a real person they actually know,” Rettig says. “That can be super helpful, but it can also be very limiting, and you want to avoid that early in your process.”

Answering the questions above can help you think more broadly and conceptually. Maybe you need someone who has experience taking a company public. Maybe they need to have launched a consumer product–or beyond that, a consumer product in the music space. This helps guide your search and take your candidate pool from infinite to manageable. “For example, I might only look at people who hail from companies that have gone public in the last five years,” she says.


Then Build An Ecosystem

The first goal of any recruiting research effort should be to develop and define an ecosystem for your search–i.e., the industries, companies, brands, organizations, associations, publications, conferences, certifications, job titles, degrees, locations, and other indicators associated with the type of role you’re looking to fill. These will help you create the parameters for your potential talent pool.

For example, for any executive role that focuses on product, you might want to create an ecosystem that includes a broad number of consumer, enterprise, software, and hardware companies. You may even expand that to include automobile companies, media companies, retailers, or large brands whose digital presence is impressive.

“Some of the best product leaders I’ve hired in the past majored in music, foreign language, or classical civilizations–not necessarily computer science,” says Rettig. “So don’t limit yourself too early. I even suggest that you look at the apps on your phone–what do you use the most often? Include those companies and explore who is leading product for them.”


Also, is the role based in the Bay Area? If so, be sure to include Seattle, Austin, Boulder, New York, and other cities in your search that people often relocate from. Candidates who went to school in the Bay Area or have worked in the Bay may be more inclined to move back.

When searching for an executive with privacy or corporate social responsibility expertise, you could even expand your ecosystem to include organizations and NGOs, as well as the public sector–academia and governmental agencies. Look at the people leading or sitting on the boards of industry groups like the International Association of Privacy Professionals (IAPP) or speaking at conferences on responsible business.

Creating this ecosystem requires some thorough digging, but should enable you to cast a wide net you can then hone. “You might start with the idea that the best candidate will come from a direct competitor, but knowing the full ecosystem can open doors to better sources of candidates you didn’t even know existed,” says Rettig.


This step is even more important when you’re recruiting someone to do something that’s never been done before. “Think about it: I was a recruiter for Target when e-commerce came into being. It didn’t exist before. Then all of a sudden, I had to hire someone who could lead e-commerce efforts, when there was no talent pool with that experience,” she says. “The same thing happened at Apple–we needed to help build a product team for the iPod when no one had ever seen anything like it.”

Her team’s first impulse at Apple was to look for people at Sony, Microsoft, and the like. But no one cleared the bar. “It was only when we said, ‘Okay, let’s get out of our own world and list brands we actually admire and aspire to be like’ that we made progress.” Nike and Range Rover topped this particular list–and the right candidate ultimately came from the latter.

When you’re running a startup, there’s a good chance you’re breaking new ground like this. There won’t be any perfect templates out there for the executives you need. And candidates at competitors won’t be exactly right. Building an ecosystem empowers you to be creative, and to see further into the pool of people who might be capable of what you need.


Rettig suggests going LinkedIn-free for a while as you assemble this map of organizations and affiliations. “When you jump right into LinkedIn, you get sucked into a very defined and closed universe, and it can constrain your thinking and what you look for. You might not discover whole professional organizations or academic programs that could yield candidates,” she says. “Make sure you don’t miss anything, and give yourself a LinkedIn detox for a week during your research phase. Google. Go down rabbit holes. See where breadcrumb trails lead. You might end up talking to someone you never would have otherwise, who introduces you to the exact right candidates.”

Nurture New Relationships

As you build out your ecosystem, you’ll come across people who are clearly very knowledgeable in the space–professors, other CEOs, investors, advisers, etc.–and you’ll want to talk to them. Not because they’re good candidates, but because they may know one, or someone else who will know one. Relationships are instrumental to this research, and may help you expand your ecosystem even more.

For example, when Rettig was looking for a privacy leader at Yahoo, she started by having her team map out all of the organizations and associations in the privacy and security world. She had them look up all of the certifications this type of leader might have. They discovered one industry organization, IAPP, that had a lot of members across several industries. She picked up the phone and called the president.


“I didn’t just start with, ‘Do you know anyone for this job?'” says Rettig. “I asked him about the big issues impacting the industry. What was everyone talking about? What were people concerned about? What kind of jobs seemed to be grabbing attention? What challenges really interested people? Could someone transition from a governmental role into a tech role? He was tremendously helpful. People love to help, and they love to talk about things they know well.” She ended up adjusting the profile they were looking for based on his comments.

Forging these relationships doesn’t just yield information, it also enhances your credibility with prospective candidates. If you’re suddenly affiliated with, referred by, or introduced by a bona fide member of a known industry organization or leader, a candidate is going to pay more attention to you and the job opportunity. At the very least, talking to a lot of knowledgeable people in the space equips you with the language to sound credible and informed when you talk to prospects–like what’s hot in the industry right now, or mentioning an upcoming conference everyone’s going to. They can have faith you’re not just repeating buzzwords, and actually understand the value of their work.

Be sure to take care of these relationships as your search progresses. If you’ve asked people for introductions or for information, keep in touch with them. Let them know how things panned out. Be prompt and responsive when they reach out to you. Ask if you can be helpful to them. You want good word of mouth in their industry, and people love knowing that their help or small contribution led to something great.


No Talent Pool Is Infinite

When you start a search, it can feel like an impossible quest for a needle in a haystack. Doing your research and building an ecosystem brings this into focus, and turns recruiting into a more orderly and systematic process of elimination.

“You want to inventory all the places this person could be, and then narrow down more and more and more,” says Rettig. “As a recruiter, I often have hiring managers ask me things like, ‘Have you tried looking at Netflix, or what about Facebook?’ My goal is to have done enough research that I can say, ‘Yup, here’s all five people capable of this job at Netflix and Facebook, we’ve already reached out to top three. Now let’s talk about how we would present this opportunity to those leaders or why they should leave those great companies to come here . . . ”

At the end of your research, you want to basically have created a checklist of places and people for the role. As you reach out and hear back, this list gets smaller and smaller until you’re left with the best possible outcome.


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