003. 3 interview questions to sniff out Heads of People who can’t deliver
You can thank me later.
[Prologue] A founder friend once asked me for some tips on evaluating some Head of People candidates, so I sent them a short version of the tips covered below. They came back a few weeks later, saying, “Your questions totally changed our interview process, and it was shocking how many ‘qualified’ candidates from well-known top companies first appeared to be super confident, but that facade fell apart quickly when they couldn’t answer a simple line of questioning. I think we definitely would have ended up accidentally hiring one of them if it wasn’t for your guidance.”
This is actually something that’s happened many times with startups I advise – but today, I’m making these tips accessible to non-friends and future friends :)
Bringing on a new executive at a startup is always exciting, but it’s also a gamble – and perhaps no other leadership role poses a higher risk and reward than a Head of People hire.
A great HoP is a game-changer for a startup, one who enables building an exceptionally strong organizational foundation, which allows the company to scale productivity and morale in the face of ever-growing complexity.
On the other hand, an awful People leader is the secret killer of companies. There’s a myriad of reasons why there are too many ineffective Heads of People out there, which I’ll detail in a future post (For now, a preview: the role’s true impact is hard to quantify and measure, it affects *every* part of the company, good People work takes *time*, etc.)
As a disclaimer: I don’t hate Heads of People, I’ve been one myself! Some of my best friends are HoPs! (💀) My problem is with the bad ones. Furthermore, some of these folks could be effective at larger companies, but simply aren’t the right fit for the startup context. Because People leaders are hard to assess, and few of us have even seen what a great one looks like, the cycle continues – But it’s time we raise our standards.
You might be thinking, “I really care about getting this right, how do I actually hire a good HoP?” It's not a question that can be answered in a single post – finding a good fit is a process, and this is why executive hiring firms exist and charge $. But below are some de-risking tactics to help you tell apart the smooth talking hucksters1 from actually qualified candidates. Read on, and let me know the result of implementing these strategies.
Are they a builder?
Can they balance business needs vs. employee needs?
Do they have integrity?
1. Are they a builder?
Perhaps the biggest problem with executive hiring is over-reliance on pedigree. Assuming that someone with X title at Y company will achieve the same results at your fledgling startup is a classic mistake – it’s easy to get blinded by shiny logos.
“Being in the room” or “optimizing established systems” is not the same thing as “understands strategy and problem-solving, adapts to new contexts, and can build the team to execute.”
Too many Heads of People are copy-pasters (“This is how I saw it done at X, so that’s what we’re implementing”), not builders.
This is especially important in a fast-growing startup, with far less resources and more pressure than larger companies. Sure, maybe some of the work, like compliance or very basic tooling won't require much strategic thinking, but beyond that, much of People strategy has to be built from the ground-up.
Take just Recruiting as one example: What kind of candidates are YOU the best fit for? What are your competitive advantages in the talent market? Employer brand? What’s your industry? Geography/remote status? Comp/equity strategy? etc. etc. Copy-pasting Google’s playbook will obviously not work here. This is what we mean by *strategy* – being able to think critically about the problem, making choices, and leading the organization through a set of coherent actions.2
How to evaluate: Copy-pasters tend to confidently speak in buzzwords that *sound* good to untrained ears, i.e. inexperienced founders. So in the interview process, get very specific and ask lots of follow up questions (provided below). If they mention an abstract concept or jargon that you don’t fully understand, don’t just gloss over it – ask them what they mean, and don’t let up until either 1) you understand it yourself, or 2) you realize they don’t either.
You can best do this with a dedicated interview step in the middle-stages of the hiring process. I call this The Project Interview – Ask the candidate to bring 2-3 examples of initiatives they led and be prepared to speak about each in detail.
Now, don’t be an asshole and grill them – having high standards does not require an antagonistic approach. Establish some rapport, then ask questions like: What was the catalyst for this initiative? How did you define the problem? Who was involved? Why? What solutions did you consider? Testing? Implementation? What was the feedback/iteration? What did you learn from it?
You should be able to tell when someone is trying to recall details by digging into their memory (because they want to be accurate) vs. silently panicking and trying to BS an answer in real time. That’s why follow-up questions around the *details* are so important. Copy-pasters will fumble or get flustered when pushed to go 1-2 levels deeper, because their answers aren’t grounded in previous thinking. If they’re smart enough, they might be able to pull out some high-level theory and make it sound plausible enough – so listen mindfully (try to relax – see tips from last week’s post!) and really press for details and substance.
How they answer these questions will be incredibly revealing. Builders will be able answer these questions easily – they may even enjoy it. Copy-pasters can’t.
2. Can they balance business needs vs. employee needs?
I was recently catching up with Ed Batista, a veteran executive coach, and he described a spectrum of startup People leaders he sees:
“On one end there’s the classic “corporate HR” – we all know the stereotype, someone who aligns themselves with management so tightly, no employee trusts them. But on the other end of the spectrum are People leaders who align with employees too much, and fuel the fire on creating more distrust in the company’s leadership, actively creating an Us vs. Them culture.”
This is a dynamic I also see often. It’s not easy to maintain a healthy balance in a role with so many “customers”, lack of clear metrics, and exponentially expanding problems. I have more thoughts and personal strategies for keeping that balance, but in the meantime – let’s examine this spectrum and understand the signs/red flags of each extreme.
Traditional HR:
Hierarchical. Primarily focused on maintaining power in proximity to the executives. “Yes men” stereotype. Corporate lackeys. Executes on top-down decisions without adequately pushing back. Often tells the CEO what they want to hear, avoiding surfacing any real People problems that might cost them an ounce of social capital.
Embodies the old-school term of Human Resources – Only looks at the bottom line, in lieu of a substantive Talent strategy that considers hard-to-quantify measures and choices (e.g. rushing to a layoff before considering alternatives, and then being surprised by the botched RIF process / reduced productivity / lower than expected cost-savings).
Initiatives tend to be rooted in antiquated tactics and lack creativity.
Their relationship with employees is characterized by “policing,” with general distrust. See the workforce as entitled children who must be put in place.
Insurgent HR:
Despite being part of the leadership team themselves, protests “The Man” and is quick to blame management for decisions, often in front of employees. Sees their job as Protester-in-Chief or internal labor organizer (Note: Political stances on unions aside, it’s not an appropriate for a Head of People at a 30-person startup to be so polarizing, when the job is to unite the team around a shared mission and culture).
Driven by passion that lacks an appropriate outlet. Often acts out of feelings and struggles to maintain healthy boundaries, whether it’s with other employees or in the greater socio-political context (e.g. We can acknowledge that white supremacy is a pressing problem and that a 30-person company will probably not be the vehicle to single-handedly solve the issue overnight).
Too reactive to employees’ needs, and overly-identifies with being a “Helper” or “Savior”. Often swayed by whoever is complaining the loudest.
Overly idealistic, preoccupied by initiatives that are impractical or irrelevant for the company’s context (e.g. announcing a big project in Corporate Social Responsibility even though the company is still struggling to find Product-Market Fit. Or, distracted by bringing on endless “DEI speakers” and neglecting the fundamentals, like improving the company’s performance/feedback processes).
Neither extremes are productive or sustainable. And while most startups tend to be wary of the Traditional HR type, it’s the Insurgent that’s often unrecognized and ends up doing some real damage. I’ve seen more than a few startups, with the best of intentions to be more Employee-centric, hire radical Insurgents to the People team, and watch helplessly as the culture devolves into an unexpected form of toxicity.
How to evaluate: First, a candidate being closer to one end of the spectrum or the other doesn’t mean they’re automatically a bad person – The Head of People job is tough, one that really does feel impossible sometimes. It’s worth recognizing that most people are trying their best.
From there, there’s no substitute for having direct conversations with the candidate! It’s impossible for anyone to maintain a perfect balance at all times. So ideally, they will be able to cite examples of pushing back on both management and employees:
“Has there ever been a time when your morals/ethics were in conflict in your role?”
“Tell me about a time when you really had to push back on a CEO/C-suite.”
“What’s your approach to employee relations? Building out a middle management layer?”
“What type of feedback on your HR leadership style have you heard from the broader company?”
“Have there been any passion projects you pursued within any of your past roles? Which ones?”
Listen carefully, and as always, ask follow up questions – it should be a dialogue, not an interrogation. Remember that you’re simulating what it would look like to actually work together and potentially have tough conversations.
3. Do they have integrity?
There are two aspects of integrity relevant in evaluating People leaders:
Having strong moral principles
The ability to tell difficult truths
These aren’t exactly “first date conversation topics” – ideally, this line of inquiry happens near the end of the interview process with only your top finalists, only after some real investment in relationship-building. If you try to discuss sensitive topics too early in the hiring process, you haven’t yet built adequate trust to get to the substance. Without a proper set-up, you can expect more feel-good buzzwords and not a lot of talk that’s grounded in real lived experience.
Integrity should be a critical trait for all of your future executive hires, but People leaders especially so, due to the unique types of challenges they face. I would go so far as to posit that the way roles are typically set up, Heads of People are not incentivized to perform at their best. A Head of People who’s looking out for their own interests (e.g. being a Copy-Paster) can obtain greater monetary rewards and status, at the cost of the teams and businesses they’re supposed to be helping build.
Again, an optimal Head of People search will take far more nuance and in-depth discovery/evaluation process (something that the Workflow team and I can help with). But here are some questions to get the ball rolling:
"Have you ever wanted to make a career switch? Any moments you’ve wanted to quit being a People leader altogether?” I don’t trust any Heads of People who haven’t been tempted to rage quit once or twice in their careers. That’s how bonkers the job really is (IYKYK). Try to understand the limits they’ve previously faced, and open up a supportive dialogue about how together, you would prevent that from happening again.
“Who was the most challenging leader you’ve ever worked with and why?" (Follow up Q: “How would you advise me to not become like that person as we grow?”) An excellent opportunity to be self-reflective on both sides! Heads of People should be collaborating *very* closely with the founders and leadership, and this is a great way to simulate a future dynamic.
“From all that you’ve gathered over the process of getting to know me and our team, what are your concerns/flags for us? In other words, what would be hard for you to give feedback on once you’re in the door, that you can share now?” Are you able to talk about sensitive truths together? Because spoiler alert: that’s a large part of the actual job. If they insist there’s nothing, that’s ok, but that's more information for you to consider.
Putting it all together
In addition to building, balance, and integrity, there’s also an underlying theme of self-awareness and emotional resilience to the above tips, because being a People leader will never not be difficult. Sometimes it's wild to me that anyone signs up for the job in the first place – you can get far greater rewards and respect in pretty much any other C-suite role.
But the great People leaders in my community prove it over and over again – we put up with the shit because we care. And we possess the skill sets to be good at our jobs, just as Heads of Sales and Product do. But the surrounding environment have long ways to go to catch up, and I believe setting great People leaders up for success comes back to hiring. When founders can hire excellent Heads of People, our collective standards will rise, and we could all see new possibilities in this space. I'm so ready for it.
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With the above 3 lines of questioning, you’re more prepared than ever to be able to filter out the mediocre and the incompetent from your applicant pool. They represent the most common archetypes of candidates that look good on paper but fail to deliver, which I've seen play out at too many startups.
Keep in mind that it’s not enough to just focus on preventing the mis-hires – your goal is still to hire the cream of the crop, a stellar leader who’s specifically that’s going to be a great fit for YOU.
And you don’t have to do that alone! This is the ✨segue✨ to how the Workflow team and I can help. We offer fractional Head of People consulting, which, in addition to laying down the foundation, is also a great way to get experience working with someone who can show you what great looks like. We can also help you screen Head of People candidates when it's time, and they'll see your engagement with Workflow as a positive sign (it means less of a mess for them to clean up Day 1 😉).
People leadership at startups has gone through major shifts in the last few years – and it’s been a grind for those of us hanging on. I was driven to the edge of quitting a few times myself, and didn’t think I could survive this career path. But I’m so glad I made it to the other side of it, where I can write to you, optimistic about the future.
If you learned something new from this post, please consider 1) subscribing and 2) sending it to a friend to continue the discussion.
Jennifer Kim is the CEO/Founder of Workflow, an education and consulting company that trains the next generation of startup leaders on all things Recruiting, People Ops, and DEI. Through its flagship program, the HireEd Accelerator, Jen and her team have taught hundreds of startup leaders to make hiring a competitive advantage. Previously, Jen was Head of People at Lever and was an advisor to dozens of top startups. She is also a Venture Partner at Symphonic Capital, and is known for her hot takes on tech industry and culture as @jenistyping.
Appendix / Past Discussions
https://twitter.com/jenistyping/status/1199764778975019009
https://www.linkedin.com/posts/jenistyping_hot-take-it-is-impossible-to-have-a-great-activity-7084922340572086272-JYRI
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