Hiring Well

I (fairly recently) advised a company who had a real problem hiring and retaining good employees. This company seemed to have all the pieces to enable top tier talent to join the team — their product was great, the founders were smart and driven, and they treated their employees really well with ample vacation time, cool perks in the office, etc.

What I ultimately noticed when I dug in more was that each failed hire they made (and there were a lot of them) either wasn’t a cultural fit, wasn’t passionate about their work, or simply didn’t have the necessary skill set to succeed.

So I worked with them to develop a simple hiring playbook and, with their permission, wanted to share it.

It all starts with CPI — Culture, Passion, and Intelligence.


Culture. The question you need to be asking yourself is simple: does this person match with my company’s values, work ethic, and environment? It goes without saying that you need to understand first and foremost what your company’s culture is like. So if you don’t know, take an hour to write down 5–10 values and qualities that match well with the employees who fit best in your organization. You want to ask questions to the prospective hire seeing if they match up. Some examples:

  1. Who do you most admire and why? I love this question because it sheds light on who the person aspires to be which is very telling for cultural fit.
  2. Why are you here? This is a great one because it usually throws them off a little bit and forces them to give a real answer about their priorities. If you have an organization in which you need people to have a “hustler” mentality for instance, their response to this question will shed a lot of light there.
  3. Describe an environment in which you would NOT thrive. They’ll be much less likely to have a canned response. You’ll learn a lot about their personality and whether or not that jives with your culture.

Passion. If a person isn’t passionate, they’re not going to be passionate about what they do. In my opinion, passion is the most important quality in a teammate. It means that they’ll do the shit work that needs to be done when nobody is looking (the most important work usually) because they know how important it is to the end product/service. It also means that they’ll work hard and with urgency — crucial factors in today’s cutthroat business world. It’s important to note that you need to also gain an understanding of how they balance their passion with their social interactions. People can be too passionate — turning their co-workers and even potential customers away with an overwhelming level of intensity (or even judgment towards people who don’t work in the same way that they do). Some sample interview questions:

  1. What are you passionate about? Obvious, I know. But ask it nonetheless. If they struggle to come up with something, they’re not a passionate person. The more time they can spend speaking to what they’re passionate about, the better.
  2. If you could do anything in the world, what would your dream job be? Their response will often times play off of whatever it is they’re passionate about, but it’s still valuable to hear this response through the lens of their ambitions.
  3. In your last employee review, what areas of improvement were identified? If they say nothing, ask them what they think they need to improve upon. If you still get no response, you know that you’ve got someone who could be dangerous on your hands. This question helps you gain an understanding of what others think of them as well as how that translated to their work.
  4. Tell me about a time you failed in work. Passionate people accept failure, learn from it, and keep fighting. They keep fighting because quitting is a non-option and their response here will shed a lot of light on their ability to persist.

Intelligence. Obviously, you need a person to be smart enough to do the work that’s required of their position. A lot of people take the perspective of starting with hiring really smart people and letting other factors take a slight backseat. My perspective is the opposite — make sure they have enough ability to do the work you need them to do well and focus moreso on their passion and cultural fit. I will take an incredibly hard-working person with moderate intelligence over a non-driven person with a 170 IQ any day of the week. Some sample questions to gauge intelligence:

  1. Tell me how you would go about doing X? The idea here is to paint some real-life scenarios for the work they’re going to be doing. Make sure they have an intimate understanding of how it would need to be done. If it’s something that you don’t expect them to know but instead be trained on — that’s fine. Then pay attention to how they problem solve; thinking on the spot and trying to tackle something they don’t know how to do.
  2. What is the relevant experience or skill that you bring to this job? Again, even if you don’t expect them to have direct experience, they need to at least have skills that line up with what needs to be done.
  3. You mentioned your dream job was X. Imagine I just gave you $1 million to launch a business around that dream job. Tell me what you’d do. I see problem solving as being the most indicative of intelligence. People are always caught off guard when I answer this question and it’s great to see them assemble a game plan step by step.
  4. What can we do better as a company. This shows whether or not they did their research as well as their ability to come up with new ideas. In certain instances, this question might not make sense for the position you’re hiring for so make a judgment call.

In this day and age, the most important fucking thing, without a doubt, is your team. Don’t mess around with hiring the right people — as the old saying guys: “Hire the right person, not the person right now.”

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