010. Hiring as Gambling: The role of risk in remarkable recruiting
Welcome to the 10th Edition of Safe For Work! When I decided to start this newsletter, I’d only committed to 10 weekly posts as an experiment, to see what writing regularly again would feel like. So far, the experience has been wonderful (even if it means every Monday, tearing my hair out because I don’t feel like I have a usable post, only to realize by Tuesday evening, the draft is looking pretty good 😝), and the reader feedback even more gratifying. I’m taking next week off, but if you want to see this newsletter continue, please help Safe For Work grow by sharing it with your communities. (No motivator like social pressure!)
I spend much of my time talking with founders, and I tend to meet them at a pivotal time in their leadership transition.
Sometimes, it’s the moment that they realize they’re going to have to take hiring more seriously, beyond just relying on referrals. Or, it’s realizing that the team they hired is not set up for success, and most of their day is spent feeling like a babysitter – a job that no one intended to sign up for, but too many founders find themselves in anyway.
First-time founders and managers are rarely fully prepared for the people challenges of their roles. Part of it is due to the irresponsibility of the system that does not adequately equip them (especially VCs – another spicy post for another day). But another key factor is lack of discussion about the psychological challenges of leadership development, not just tactics. Here’s a story about that.
I was talking with a startup founder who recently had to fire a new employee. The transition entailed cleaning up a big mess. The new hire, despite having been at the company for only a couple of months, was quite damaging to the team’s productivity and morale both, and had been quite combative on their way out.
The founder herself was struggling with the loss of confidence and clarity, which I was helping her process. Cycling through her head were unproductive loops of “How could I let this happen?” and “Why didn’t I see the signs?” And when we really got deep into it, she admitted that self-doubt was kicking in, and wondered if her team’s trust in her as a leader was permanently damaged.
All of this is very understandable. Leaders feel the pressure around hiring, as there’s no shortage of messaging from industry leaders, investors, and peers around how you HAVE to nail it. But there is a perspective that I don’t think most people have heard, that I like to share when leaders get in their head:
Hiring at its core, is about trying to make decisions about other humans, based on incomplete data.
Every candidate is a complex individual with a unique set of skills, motivations, experiences. One of the things that makes People work hard is that it’s impossible to guarantee outcomes. The concrete types of goals that are standard in Product or Growth (e.g. 99.99% uptime) are impractical in this area. In fact, 100% certainty and rationality in hiring is actually impossible.
“Wait, what is the goal then?” you might wonder. Skilled hiring is not about perfection, but the ability to continually learn and improve your process — attracting a quality top-of-funnel, surfacing relevant data through interviews, and then making decisions with reasonable risk. All the while, continually being throw curveballs with new candidates, evolving hiring team dynamics and markets. That’s why you can never be “done” with your hiring process, and being good at it starts with accepting that. And you should allow room for experimentation and growth – which yes, does entail sometimes making a mishire or two. It’s gambling, but being smart about it.
The key is to discern Stupid Mistakes vs Learning Mistakes in hiring.
Stupid Mistake: Easily preventable mistake caused by negligence, e.g. losing a great candidate after dropping the ball on scheduling. There’s no excuse or lesson to be learned there, except to Get It Together.
Learning Mistakes: A part of startup growing pains, that come down to human factors that teach you how to do better next time, e.g. an executive that came recommended by a VC, but the exec felt rushed, and ends up being an ineffective leader and eventually returns to a big company. While painful, this mis-hire led to a valuable lesson about the importance of Motivation Fit, and an opportunity to do better next time. (Beware, ignoring a Learning mistake will turn it into a Stupid Mistake.)
Hiring mistakes that come down to human factors are part of the deal. I can’t tell you the number of times I’ve seen founders and Hiring Managers kicking themselves for a bad hire. Taking responsibility as a leader is a good thing, but that energy should be channeled into making improvements and renewed commitment to take People work seriously, instead of into self-doubt and punishment. “Oh. That actually makes me feel a lot better,” said the founder from the beginning of this story.
Remember: risk is part of hiring.
If an experienced Hiring Manager claims to make no mistakes ever, and boasts a 100% offer acceptance rate, this isn’t actually impressive to me, it’s a flag. They’re likely playing it too safe, only sending out offers to “tried and true” profiles, thus not actually building the best possible team. (Or they could be neglecting performance problems, or overpaying, which pose different business risks). In startups, where the train is being built as you go along, perfection is impossible. Even the best leaders will end up having to let people go (sometimes 20-30% of hires!) as the company grows and needs change. The key is to be able to spot and correct issues early as necessary.
It’s like catching flights – If you never miss a plane in your life, that means you're spending too much of your short, precious life waiting around at the airport. As a leader, you’re supposed to take chances on people. This is especially true at a startup, where people are also taking a chance on YOU. Just know that aiming for high-potential hires will entail some mis-hires too. That's a good thing.
OK! That’s the psychological pep talk. Now, here’s some tactical advice if/when you find yourself in similar challenges around hiring:
1. Don’t let anxiety and self-doubt take over.
Are you being kept up at night by the thought of a mis-hire that comes in to ruin the culture and progress? Then, you might be reassured to hear this: I’ve run dozens of post mortems with Hiring Managers over the years, and I’ve found that most people DO pick up on red flags 🚩with a mishire during the interviews. A true “out of nowhere” mishire is very rare. More likely is managers who have not yet learned how to be sensitive to red flags within themselves and their team, but this is a solvable problem! Pay attention when your gut picks up on a warning sign, and make sure there’s good support systems in place to catch and act on them (e.g. a great recruiter!)
2. Great hiring is not a standalone process. Invest in broader, great management practices.
Accept that hiring entails risk, and that great process – which you again, are in control of! – can help you manage it. If you want to be great at hiring, that means you’re also committing to being great at managing performance and terminations as necessary. (I have an upcoming post on this!)
3. Share the lesson from a mis-hire with others.
Too often with a mis-hire, leaders are too embarrassed, even ashamed, to admit what happened. That’s a loss, because addressing it head on allows the company to learn, especially when it was a Learning Mistake.
Being able to own our mistakes is a key part of leadership. And given that so many hiring mistakes tend to be repeated, leaders who can share honest stories without villainizing anyone can model important lessons for their growing team. This does take quite a bit of nuance, so slide into my DMs so you can have the right support :)
In closing
Hell is other people1 but… so are the best parts of life. Same is true for building organizations.
For many leaders, hiring can often feel like the worst part of their job. That’s why so many technical leaders want to code again! – just to feel like they’re good at something again! This is true for leaders across all functions, not just engineers.
But it IS possible for hiring to be the best part of the job. It entails 1. Taking some pressure off 2. Committing to investing in the work and getting some real help (DMs open / this is what my team and I do at Workflow), then 3. Allowing your team to thrive and surprise you with results. But it starts with you. You can do it.
As mentioned, I’ll be off next week! 👋 Show your support for Safe For Work by 1) subscribing to for more hiring hot takes and 2) sharing this post with a colleague.
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 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
No Exit, 1944