As a team of People Ops pros, we’re often giving advice to people finding their first full time HR leader. Most of us have also been a first “Head of People” ourselves, joining early stage companies to build the HR function from scratch. Many founders are confused who to hire for this role (we’ve seen everything from “my niece who needs a job” to “VP I lured from big tech”), yet it has an outsized impact on the company’s culture and output. A great HR hire can attract an incredible team, be one of your most trusted advisors during rough times, and build custom programs that act as a magnet for top performers. A bad hire can weigh you down with big company process, take a copy/paste approach to culture, or even cause a mutiny. Here’s how to beware the smooth talkers and pick a good one.
Get on the right level.
A common mistake first-time founders make is to hire or promote someone inexperienced into a Head of People role. Seeing the job as more administrative, they hire a friend or enthusiastic recent grad and let them run with it. As the company’s sole HR resource, they’ll be great culture builders and helpful in setting up and running basic processes like benefits administration, but will struggle to be helpful in times of change, conflict, or with more complex strategy work like organizational design or compensation. Though there are exceptions, the startup burnout graveyard is littered with well-intended first time HR leaders.
That said, the big-tech VP who is used to having a large team might not be the best fit for an early stage company either. They may not want to get in the weeds of day-to-day admin, but there just isn’t 5 days of strategy work for them to do either. A fractional HR resource (👋), combined with an enthusiastic junior can be a great solution when you’re small.
Some sample candidate questions:
- Tell me about your last team. How big was it, and what was everyone’s role?
- What was your leader’s management style like? Did they work very closely with you?
- How will you know when you need to hire and scale up your team?
Evaluate their skillset.
HR is a broad role that covers a wide range of tasks spanning soft skills and technical how-to. For founders that are completely new to working with HR (and the folks who have been dropped into the role and are trying to learn quickly), we made this Guide to Working in HR as a 101.
At this stage, you’re looking for a generalist. Here are just a few things they’ll touch on:
- Building ways for employees to grow their careers and receive feedback. This includes defining career paths, setting written expectations for different jobs, and designing the mechanisms that measure if people are doing them well.
- Compensation. Though this is often in partnership with finance, HR should be involved in designing your compensation philosophy, and designing and rolling out salary and equity bands.
- Policies. Here, you’ll want to dig in and see if your candidate relies on legal (or google) or can advise on various options and what will and won’t work for your culture.
- Experience with accessibility, health and safety, and employment laws. This is an area where a lack of knowledge can quickly go wrong when an issue pops up.
- Coaching and employee relations. They’ll need the confidence to coach senior leaders, and the empathy and relatability to build employee trust.
- Designing and running hiring and onboarding systems that feel on brand for you, get you the right people, and save your team time. One caveat here; HR and recruitment is not one and the same. While a lot of first time founders combine the role, most people are good at one or the other, and/or won’t have time to do both. Filling 5+ open roles at a time and doing everything else listed above is one of the most common failure traps.
- How do you support employee growth? Tell me about your experience designing career paths/employee growth plans/performance management systems
- How have you partnered with leaders when it comes to compensation?
- What’s your approach to writing policies?
- Tell me about a time you helped coach an employee who was having a difficult time.
- Tell me about a time you coached a leader through a tough team issue.
Think experience, not education.
This may be a controversial take, but we don’t believe that the HR designations many companies automatically add to their job postings are any indication of quality. Many Human Resources degree programs and designations (which are often run by separate, for-profit organizations) focus on large, corporate HR practices and can be quite out of date with modern thinking in the field. While having these designations isn’t a disqualifier by any means (and they can provide a good base level education for juniors), we don’t recommend you include them as a must-have. Focus on your candidate’s experience, approach, and understanding of your business.
Evaluate Their Mindset.
Good HR is a balancing act between supporting the company and its team, and occasionally, those interests will have to diverge. Your Head of People needs to be strong enough to bring you tough issues and push back when they know a decision will impact morale, but also have a strong enough business sense to understand why unpopular decisions sometimes need to be made. In other words, they’re not there to be your yes-person, nor are they there to be a protesting, authority-fighting employee figurehead. The former will lose employee trust and breed a culture of fear; the latter will war with leadership and encourage a toxic “us vs. them” mentality. Having balance here takes experience and maturity.
- Tell me about a time you changed leadership’s mind about something.
- Tell me about a time when you had to roll out a decision that wasn’t popular with employees.
- How do you build trust with different levels of the team?
- In your view, what is HR’s role in an organization?
Evaluate their alignment.
When hiring any leader, you need to understand yourself and your company’s DNA to get perfect alignment. Are you a “move fast and break things” kind of place, or does slow and steady win the race? Be sure to make sure you’re philosophically on the same page with your hire on the type of workplace culture you’re going to build together. A lack of alignment here is a recipe for frustration. When building an inclusive culture, you’ll also want to ensure your hire has a deep awareness of modern diversity and inclusion theory and practices.
- What cultures or companies do you most admire?
- How would you ensure you’re creating an inclusive culture? What other companies do you think do a good job of this and why?
Make sure they’re a builder.
Some HR leaders are great at inspiring teams, growing relationships, and strategic thinking, but struggle with the most important thing a startup needs; hands-on building. If you're in the startup or scaleup phase, this is not the leader for you. Here, you want to look for evidence that they can roll up their sleeves, work alone, and have the confidence to make strong recommendations and/or just do things. At the same time, they need to be thinking of the big picture. After all, they’ll be both creating the roadmap and driving down it.
- In your previous roles, what were some of the areas or programs you tackled in the first year? What led you to choose these programs and why did you tackle them in the order that you did?
- How do you know and measure how your programs are working?
- What program did you build that you are most proud of? Dig in here on how involved they were, and look for evidence that they can come up with customized solutions vs copy and pasting things that worked elsewhere.
Riff on a real problem.
While you shouldn’t ask for a full HR strategy as part of your interview process (unless you’re paying), do take the opportunity to fill them in on a current, real challenge you’re having and see how they’d approach it. While they won’t have the full context, this will give you a good idea of how you might work together. Is this someone you'd want to take advice from? Green flags include asking thoughtful questions, presenting pros and cons, having an opinion, and having the confidence to tell you how you could do better.
Finally, once you make your hire, give them a bit of time to shine. A great HR leader doesn't rush into implementing a massive project wishlist. Instead, they start by actively listening, learning from what's been working and what hasn't, and taking the time to understand the values they'll be building upon. The future of your team’s culture is in their hands, and the job shouldn’t be taken lightly.