How to Find the Best Head of People
One of the most valuable ways we can maximize service to our portfolio companies is to help our founders hire strong people and operations leadership.
But how do we do that? What do we look for and how do we evaluate these candidates? Where do we find them? What makes someone good at this job versus outstanding at this job? Below you’ll find steps to consider when looking for (and hiring) your Head of People, whether it’s your first or one taking you through your next critical phase of growth.
Step 1: What to look for and where to find them.
I look for Heads of People who are good storytellers. Good storytellers can appeal to a wide range of audiences and understand where to add vibrance and when to move onto the next topic or chapter. They understand how to read the room, no matter how big or how small. Good storytellers also let the story speak for itself but up-level it each time they tell it and they know how to customize it as needed.
I started out working on the creative and technical side of advertising and production, then moved into assigning people on the creative and technical side of advertising and production to projects based on their skill sets (resource allocation) and eventually into recruiting them, then hopped over to the other side to build recruitment products, and ultimately moved into executive search for high-level companies and hyper-growth for startups. I tend to find that good storytellers did something else before they started recruiting, which adds value to them as a recruiter and as a human capital asset.
Look for people who are involved in multiple organizations, clubs, associations, etc. The best Heads of People are active in communities, ecosystems, and causes they believe in. This might not always be listed on their LinkedIn or resume but learn through conversation what substance there is in this arena, and if there isn’t any, pass on the candidate. What Heads of People do when no one is looking says a lot about who they are and who they will be for your organization. An exceptional Head of People isn’t going to prioritize diversity and inclusion the way they need to unless they do it when no one else is looking, the same way they will take extra steps to improve the candidate experience or the organizational structure of the company as it grows because they want to vs. have to.
The next set of criteria to prioritize is their experience working with companies going through different stages of growth. I tend to hire Heads of People who have been through and lead an organization through multiple phases of a company life cycle. Try to find someone who has been with a company when it was less than 10 employees, less than 100 employees, has been at one of the big four-ish types (Amazon, Apple, Google, Facebook, Tesla, etc) and someone who has been through some sort of exit so they understand these different experiences and how they affect teams and culture. I also look for candidates who have had to own recruiting across engineering, product, marketing, operations, and finance at many different types of companies. There is immense value in someone having experience directly with your market but also with surrounding markets as you have to reiterate on where you source candidates from as you grow.
Step 2: Get into the right mindset: You don’t get what you don’t ask for, so go big, and start early.
The Head of People ecosystem is very competitive this year. Because of that, spend more time proactively recruiting for this role than you may spend on others. The chances of the best person falling into your lap is rare right now, given the number of companies rebuilding as things begin to rebound and evolve from the pandemic. Spend time refining your pitch, making it relevant to each individual candidate you are speaking with and highlighting challenges and opportunities you are facing as you draw lines between their experiences and what your team is working on or preparing for.
Give yourself extra time, say 15–20 minutes, before your Head of People interviews to properly prepare for the conversation. Have a good base story script and leave room for customization throughout the conversation, so the candidate can feel you are present and well informed about what they’ve worked on previously and why you are talking to them about this role. Hiring the best Head of People possible requires you to be buttoned up and prepared, showing up yourself instead of telling them how you want them to show up for your company, and your candidate pipeline each time they meet with someone.
For this role, in particular, give yourself a healthy budget and aim high. This will be one of the most outwardly facing people at your company so really focus on finding the right Head of People –not just someone who can do the job. Find someone who lives and breathes the values. Again, not because you are asking them to do it, but because you’ve found alignment in it through targeted search and in-depth discussions about human needs.
Step 3: Create 3–5 questions that evaluate for value alignment before spending time on role-specifics. Here are some suggestions:
1. What do you want to do differently in your next role?
With this question, look for them to naturally highlight what they are running toward, rather than running away from, if they were to leave their current role.
2. For your last few roles, take me through: (i) Why you joined, (ii) why you left, and (iii) why you chose your next role after that.
You are looking for them to outline their own progression and growth plan throughout their career and aiming to understand what causes them to move onto their next endeavor.
3. What’s the difference between someone who’s great in your role versus someone who’s outstanding?
They should have many, many opinions about this if they are a strong Head of People leader. The best recruiters are the most particular of others in similar roles but with a ‘rising tides lift all boats’ mentality.
4. What is humankind’s greatest achievement?
This question is my favorite and I ask it in almost every interview. It helps you understand what someone’s natural motivations are in a setting that isn’t explicitly tied to work but is tied to their fulfillment at work. If you are interviewing a CTO and their answer is currency, that should be a red flag, as you do not want your CTO’s primary motivation to be monetarily driven. However, if you were interviewing a Head of Biz Dev and their answer was currency, that could be a great fit. With the Head of People, I’d be looking for an answer that falls in the realm of “toolmaking” or “written language.” Something that inherently brings people together or helps them communicate and collaborate to solve a key objective that benefits those around them.
After I ask this question, I tend to ask the candidate if they want to know my answer. My answer is the ability to harness and control fire, which is ironic as we continue to see wildfires rage all over our planet. But my reasoning is that when humans achieved the ability to harness and control fire, they created the ability to provide protection and warmth to our species during colder months or climates and throughout the night. It also gave us the ability to cook food which allowed us to derive more energy from meat. Fire allowed us to make items out of clay and sand that were hard enough for usage and helped us make materials like bricks. It helped us create different tools out of metal and brought people around hearths where language could further develop and spread. Fire advanced us as a species and has been foundational to building community.
When you are evaluating a Head of People on value alignment, look for stories that speak to you and the type of brand you want to build. My answer to this question is not just representative of my values, fire has always brought us together which is important when things get really hard, but that is also core to our value system here at Prime Movers Lab and we immediately found alignment in that. Not because our General Partners asked me to think that way but because we all already did, we simply found alignment in those values and in what creates and spreads that fire.
Step 4: Balance creativity with structure.
As mentioned earlier, the creative part comes into play when developing, updating, and curating the story about why someone should join the company or continue to grow with the company, but it also comes into play when having to continuously come up with new ways, places, and strategies to continuously generate strong leads. As companies scale, some of the most important qualities in your Head of People will be having enough experience to know what questions to ask along the way vs. always knowing the answers to those questions. Sometimes this person will have to come up with creative solutions to help achieve company goals while also adhering to legal structures and creating their own structures to support significant but functional growth while keeping company culture intact. When you’ve got five flaming plates in the air, you’ll need this person to find a way to juggle the extra ones without letting any hit the floor and without getting burned. The right person will find that thrilling and fulfilling but understand that they cannot do it alone or all at once.
Below are a few examples of questions that help address these areas.
1. Have you ever had an external recruiter walk away from a search you were leading? Why did they walk away? What role was it? How did the role end up being filled?
Strong Head of People candidates know how to manage both internal and external expectations at the same time, even while they are shifting in real time without a plan. With this question, you are looking for them to admit a few defeats or struggles, but hopefully, they ultimately solved the problem. If not, as long as helpful lessons were learned, then onwards.
2. What is your experience like with compensation and equity leveling? How do you like to set up these structures? How do you evolve them over time?
Again, looking for thoughts, feelings, and opinions about these structures with experience working through relevant work streams.
3. When was the last time you changed your mind about something important? What was it? What caused it? What would you like to do differently moving forward as a result?
Here you are looking for admission of the evolution of thinking or actions and what encourages them to think about outcomes from a different angle or perspective.
4. Have you ever had to fire someone you’ve hired? What do you wish you would have done differently to support that person in finding success within your organization?
This question is about exploring empathy and progression together.
5. How do you source for candidates? How do you generate new pipelines once you’ve exhausted your current ones?
It is really important that they have a well-balanced answer to this question. They may describe online events, offline events, university or alumni initiatives, podcasts, and social media strategies, using less obvious places to source like Reddit, referral network strategies, platforms and job sites they like to use, etc. When I used to do a lot of recruiting for B2B and B2C startups in Silicon Valley focused on app-based solutions, I would scour the top free and top paid apps on Google and Apple’s platforms, then work backwards to figure out who the key engineers were who helped build them. You don’t necessarily have to be looking for a right or wrong answer here, just something unique that opens up your mind about new ways to build relationships with and target relevant and interesting candidates for your team.
Step 5: The close should be easy.
The strongest Heads of People are honest and transparent about their wants and needs upfront, because they know that is the best way to recruit effectively and successfully, and ideally would desire this same transparency from the candidates they recruit. A strong candidate will interview you just as much as you interview them throughout the process, and if this is done effectively…the close should be easy.
Prime Movers Lab invests in breakthrough scientific startups founded by Prime Movers, the inventors who transform billions of lives. We invest in seed-stage companies reinventing energy, transportation, infrastructure, manufacturing, human augmentation and agriculture.
Sign up here if you are not already subscribed to our blog.
