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10 Things to Consider When Interviewing for a Head of People role

As a multi-time Chief People Officer and advisor, I have seen the approaches that set People leaders up for excellent CEO/founder relationships with our make-or-break function.

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Jan 17, 2024
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Last updated on Apr 17, 2023

We all know that it is never too early to invest in people, and a great Head of People is often the best bet for getting this important work done correctly.

In my time leading People teams, I’ve learned that my ability to make an impact and my interest in continuing to work at the company was inextricably linked to the company’s Founder /CEO. Looking back on my best moments and my most challenging ones, I’ve realized that other People leaders in recruiting processes for a Head of People roles may benefit from the lessons I’ve learned having personally been through the recruiting process many times.

During the recruiting process, ensure that the Founder/CEO is:

  1. Hiring for their needs: A common mistake is that companies bring on their Chief People Officer or senior people leader when the work that exists today is still highly tactical. The work they envision this leader to take on in the future might be to create groundbreaking employee programs and processes, but if today’s work is all blocking and tackling and very little strategic building, they should consider leveling the role down to a Manager or Director. 

  1. Not overselling: Founders are inherently charismatic sellers. They sell investors on their vision, customers and clients on their products and services (oftentimes even before they are built), and employees on the promise of outcomes and opportunities. When a founder sells a vision for a role that fundamentally doesn’t exist today, and won’t for quite some time, the people leader is likely to churn out. A Head of People leaving can send detrimental signals to the organization, even if the churn is healthy. This is avoidable if Founder/CEOs paint a realistic picture for the role, and find the candidate who is attracted to that role. Make sure you ask plenty of questions, and pressure test the answers with other leaders and employees around the company. Look for consistencies in storytelling.

  1. Seeking differentiation: Why is this culture or product dramatically different from all the others? If you are the right candidate, you will align with the CEO, their leaders and the quirks of the organization. Lean into these differences—what makes this role so different, so special, and specifically exciting? Make sure you can answer that for yourself.

  1. Being realistic: Great Heads of People are both operational and strategic, but they are not magicians. People are engaged in, retained by, and work for their managers and the company—not HR. Ask yourself why this company is hiring a Head of People. Are they looking to you to be a silver bullet and solve problems outside the scope of their role and the realm of possibility?

  1. Not overpromising: CEOs and Founders make promises every day that they work very hard to keep. However making those promises to a Head of People candidate and not being able to keep them could fatally damage the working relationship. For example, promises about the speed at which they plan to grow their employee population or about the size of the team that you will be able to hire, can fundamentally change the shape of this role. Overselling or mischaracterizing current challenges can lead to fast turnover in the Head of People position.

  1. Avoiding buzzwords: Every startup needs a ninja and thinks they are a disruptive rocketship. Real talk: A founder once told me that Sheryl Sandberg didn’t ask what seat she was going to sit in the rocket ship at Facebook when Mark Zuckerberg asked her to join, she just got on. Generic buzzwords and analogies are a huge turnoff to seasoned people leaders who are used to these words not being backed up by anything. Make sure the Founder/CEO shows you there is substance!

Be on the lookout for a Founder/CEO who will:

  1. Trust their People leader and listen: They are hiring for this role because they’ve  identified an area of opportunity, something that they are missing. The best partnership will be the Founder/CEO who trusts the expertise that comes in. As a new hire, you will have some feedback they might not love, but those things have validity even though they will be difficult to hear. 

  1. Be authentic: Look for a Founder/CEO who will lean into their weaknesses and be open about them. As their Head of People, you can help counterbalance or overcome them, but only if your leaders are open and honest. 

  1. Lead from the front: A common misconception is that a Head of People should be the one having all of the hard conversions around feedback, performance, compensation, and change. This will lead to failure to create important cultural change, burnout from the people leader, and a coercive culture. Look for a Founder/CEO who understands that their employees want them to lead from the front; they want to see that behavior modeled by the founders. 

  1. Doesn’t under invest in the People function: The best way to set this role up for success is to keep the people leader out of the day-to-day weeds. The Head of People should be the most senior HR business partner to the CEO and the leadership team and should manage people in the function running key processes, like recruiting, HR business partnering, performance management, leadership development, compensation, etc. If companies underinvest in the People team and the technology suite, the Head of People will inevitably be pulled into day-to-day firefighting and struggle to lead strategically. 

The right Head of People can be truly transformational for your business. They can help unlock your own potential and the potential of your fellow leaders, and can support the cultural change that your organization needs to take you into your future. However, they cannot do this alone. Choose your opportunity wisely! Best of luck on your search.

To discuss this or other career navigation topics, reach out to rebecca@primary.vc.

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