Reflections on my Most Recent Job Search
I’m sure we’re all familiar with the prisoner’s dilemma. This small theoretical exercise is an astonishingly accurate model for many real world interactions. If everyone can cooperate, trust each other, and work together in harmony, this will achieve the best overall outcome for the group. However, if one person takes advantage of that trust and betrays others, they can benefit more personally, at the expense of others and of the group. This is the foundation of “politics” within companies — while the company as a whole would prefer everyone to cooperate to produce the best outcome, each person working there has more of an incentive in reality to benefit themselves: to get a raise or a promotion, to further their career, to gain power and influence, etc. And so we see this dance play out, over and over, where power games and politics are played out internally by everyone trying to get a leg up, at the company’s peril.
It’s both a crazy backwards concept and makes perfect sense at the same time, frustratingly. And as I have progressed my own career from being an IC, to management, to upper leadership, I have increasingly had to grapple with the realities of interpersonal politics within companies. The further up you rise, the more politics you witness, and the more shrewd politicians you deal with regularly, as stepping on others’ backs is the quickest and most reliable way up the ladder. And as I have spent more time watching politics play out and cause unnecessary pain and drama, I have become more interested in whether there is any way out of the painful game for an organization.
I left my previous job about 5 months ago. I had decided to be a lot more conscious and thoughtful about this job search — to take my time. I had never taken more than a week or two unemployed in my 12+ year career, and on top of that my wife and I were expecting our second child in about a month and a half, so I wanted to take a proper family leave and didn’t feel like it would be the right decision for myself or the company I went to work for to rush into a new job, only to almost immediately takes 3 months of leave.
I had never really interviewed extensively — so far in my career one job has led naturally to another — so this was a new experience for me, and I sat down and resolved to commit to a few specific goals in companies that I wanted to work for:
- A product that I could understand fairly quickly, and made logical sense as something that would be valuable for its customers.
- Attention to detail in design and user experience. In my experience, even at very early stages, sloppy design and a messy user experience is the sign of a weak product and team, where high polish indicates the opposite.
- The company is willing to pay competitively for strong talent. I have seen too much talent lost from companies being stingy in the past. Great results require great talent.
- The company’s leadership team has a culture that is empathetic, kind, mature, and pragmatic. Founders/leaders on a power/ego trip, which unfortunately is very common, leads to frequent conflict and politics, which are toxic for company culture.
The first three points are fairly easy to screen for. The first two can be screened without even speaking to anyone, just by exploring the company’s website and product. The third is a question I would consistently ask in interviews. While I of course would love to get a great offer for myself, the primary motivation here isn’t maximizing my own compensation, as much as for gauging whether the company truly values talented staff and is willing to put their money where their values lie — whenever I land, my goal is for it to be a world class team, and that’s not going to happen if the company isn’t willing to pay competitively enough to get world class players (within reason, of course).
The final point is the one that was the most difficult to figure out, but also in my opinion the most important (an unfortunate combination). Over the course of my months of interviewing, I developed a few methods that helped me to get closer to an answer, which I will lay out in the following sections in the hope that they can perhaps help others.
Meeting With & Challenging Leadership
When making a decision to join a company, I want to make sure I have had a chance to meet the leadership team, ideally a few of them, but at least the founder and/or CEO, even if it’s just for 30 minutes. This time can be some of the most impactful and informative in your interview cycle. This should be possible by request for folks interviewing at almost any level, as long as the company is sufficiently interested (have had several good interviews, passed a technical interview, etc). I have a few goals for these interviews, which we’ll talk through below.
Vibe Check
Is this person friendly, relaxed, and happy to meet me? Or are they busy, stressed, or distracted? If the latter, call it out and see how they react. It’s totally excusable, especially as someone running a company, to be busy, stressed, or distracted. It’s an extraordinarily difficult job. But you want to meet with them when they are at their best ideally. I might say something like “You seem a little stressed, is everything going ok? I am sure there’s a lot going on, and am honestly happy to meet another time if it’s better for you.” This type of question serves a double function: it’s a bold thing to say and a bit of a challenge, so you can see how they react to a challenge (more on that below), and also, it displays emotional intelligence and empathy, giving this person a chance to opt out of a situation where they aren’t in the space they want to be.
If you do end up calling this out, you need to watch carefully for a reaction. There are generally two directions it can go. First is a fast denial, something like “No I’m ok we can continue” — this is not what you’re looking for. It’s a very normal reflexive response to a challenge, but you are not looking for a leader who responds reflexively, you are looking for someone who is adept at handling challenges, and that means taking a moment think about what’s being said, and respond honestly and genuinely. A response along the lines of “Yeah, there have been some stressful things I have had to deal with recently which might have given you that impression, I am sorry. But I do think we can continue the conversation”, is totally reasonable. Even better is if they open up a little about what has been bothering them, take you up on your request to reschedule, or ask for a minute to respond to a message or something. It’s not super likely you run into this situation overall, but if you do, being prepared is good.
And in the much more likely circumstance that they have great vibes going on, continue on. But keep your antennas up for the rest of the conversation, small things can quickly change the vibe and you want to notice this. For this reason I very much recommend a video call or in-person meeting, as you can pick up on body language cues much better.
Push on Sore Spots
Chances are you aren’t going to meet with the founder and/or CEO as your first interview, so you will have some time to collect information from a few interviews beforehand. Make sure to ask questions about company culture and company values, how tightly these are adhered to in practice, whether there’s anything they wish they could change or are working on improving, how they are thinking about change as they scale up, etc. throughout these interviews. You want to get a balanced view of the company — no company is perfect and they are all working on improving lots of things. They should be open to talking about these things with you — if they are not this is a red flag.
By the time you get to the CEO interview, you should have collected a few things that are perhaps challenges or sore spots for the company. You should ask them about these things and see how they react. Are they aware of the challenges, open about them, and willing to discuss them with you? Or do they get a little defensive about them? Does the vibe change? Take careful note of the responses here. You are looking for someone who is open, aware, and ready to dive into a challenging discussion about these topics. Ideally, you find someone who is eager to do so, and appreciates that you even asked. Indications of being closed off, angry, or defensive are major red flags.
Through the natural flow of conversation, you may also come across other things which you aren’t totally on board with. Don’t be afraid to gently challenge them — you’re not trying to be aggressive or like tell someone they are wrong here, but gentle challenges are a healthy part of making decisions and building businesses, and you want to make sure the leader is receptive to them.
As an example from my own job search, I spoke with one company where it was brought up in multiple interviews that the company takes pride in the fact that they are quick to get rid of people who aren’t the right fit. This can absolutely be a positive value if done with empathy — when someone is underperforming, stringing them along does no favors for the company or for that person’s career. I have worked with people who weren’t the right fit for a team I was on and were let go only to have their careers flourish when they found a better fit for their skills and interests at a different company.
However, this is a sensitive area and must be handled with great care, as being let go is a profoundly negative experience for most people. In my opinion, if you’re going to let someone go, you need to meet with that person and tell them very clearly that their job is in danger unless a certain set of things changes, and give them some period of time to remediate. Surprise firing someone over issues they were not aware of and were never given a chance to decide if they wanted to remediate is — again in my own opinion — unkind, and no way to treat people. Many companies have PIPs for this purpose, but it doesn’t always have to be a formal structure as much as a company value: if someone is going to be let go, they need to know in advance and be given a chance to try to remediate if they want to.
In my interview with the founder, they mentioned again that being quick to get rid of people was a point of pride, so I asked about their process of doing so, and they were not on board with the theory or practice of PIPs and felt like if you just knew it wasn’t going to work, it was fine to just fire someone without clear warning. However, the conversation was still on positive terms and they were ready and willing to engage in the difficult topic and go back and forth on it. So, while the disagreement remained a red flag for me about the company, the founder’s response to being challenged was positive, in that they were ready to engage in a pragmatic discussion, rather than shutting down, or getting angry or defensive.
Ask If The CEO Would Be Willing to Step Down
This is perhaps one of the more extreme examples, but is something that I do regularly in my interviews with CEOs, and is to me a very informative line of discussion. Let’s add some context: the people who start companies typically have a passion for the company’s product, and did a lot of the work to build the product and get the company off the ground. However, as companies grow and scale, the job of the CEO becomes much less about the company’s product as the company’s metrics, finances, position in the market, and how to allocate money and resources to which parts of the company in order to keep things on track.
It’s quite common that there’s a point in companies’ growth where the original founder/CEO needs to reckon with this — the nature of their job is changing. Do they still like this new job, or would they prefer to focus on what put them there in the first place (product/engineering/sales are most common strengths for startup founders), and promote or hire someone else into the CEO role to take on the new job? This is a stressful and difficult time for founders, I have heard this personally from several founders of companies I worked at and friends who founded companies.
So, here’s the question for the current CEO (and this is assuming the company is under ~1000 people and/or the CEO has been in that position since the company started): is this something you have thought about? When that time comes, would you want to hire an external CEO or COO to run company operations?
This question is a difficult topic and a challenge for any founder, so you get to observe how they react to challenges as discussed above. What you are looking for here is a healthy, balanced, pragmatic response. They do not need to know the answer or even have given it a lot of thought, so long as their response is calm and pragmatic. Any signs of anger or defensiveness are a red flag.
Ask About Company Values
Not all companies have values at all, and many of the ones that do have them just as things that are written down somewhere but don’t really have any day-to-day impact. A company’s values are a deep reflection of how leadership feels they want the company to operate though, and if you can find some, spend time reading through them and thinking about whether they align with your values.
Just as important as the values they have are the ones they don’t have. Are all of the company’s values focused on work and productivity? What does that say about kindness, community, and fun? Look at both the values they do have and the ones they don’t as part of your evaluation.
If they don’t have values, ask what people think are the company’s defining values as part of your interview process. Take note on whether you get the same or different answers.
If they do, make sure to ask whether the values feel like they are really adhered to and a consistent presence for all employees, or whether they are just written in a document somewhere. You want to get answers to this from both leadership and ICs, as they could easily be different. Regardless of the values, ask what people feel is special or unique about their company, compared to other places they have worked. This line of questioning will reveal a lot of interesting insights about how a company operates.
Prod Kindly and Gently Without Bias, Ask About The Good Things Too
A lot of my advice above is oriented around trying to find out the cracks in a company’s surface. I genuinely feel like this is a really important thing to evaluate when thinking about where to work. You will spend the majority of your waking hours working for this company, and that is not to be taken lightly. However, you should also make sure to prod gently on these cracks. While you are looking to see how folks respond to pushing on sore spots, you still need to be gentle and clearly coming from a place of good faith when doing so. I can imagine taking these lines of questioning and turning them into something aggressive that would provoke a negative response simply because your vibe check didn’t pass.
Don’t let answers bias you either. If you have unearthed a sore spot, remember that no company is perfect and they all have things they are working on. Stay positive. What matters is that they are willing to acknowledge and work on these things, not that the things exist.
And to help yourself to stay balanced, also ask about good things. What are peoples’ favorite things about the company? What have they learned from working there? The answers to positive prompts are important too, and you need to make sure you’re asking positive questions so that you’re not seen as focusing only on the negative.
Joining Clerk
To wrap up this reflection, I want to talk about the company I decided to join. I interviewed with a lot of companies, and had a lot of very strange and uncomfortable experiences through this process. But one company stood out clearly from the rest, and it was Clerk. I pushed and prodded on all of these things, I asked the CEO if he’d be willing to step down, I ran through a long list of questions about challenges for the product, and the folks I talked with (extra props to Colin for handling the bulk of my prodding), handled them with positivity, pragmatism, and grace. There were no indications of politics or ego trips or unkind practices. I repeatedly emphasized my passion for building a honest, kind, and empathetic company culture where we all work together instead of trying to step on each other, and everyone from employees to leadership to the CEO to their lead investor enthusiastically agreed that this was the sort of company they wanted to build as well.
I am beyond thrilled to be starting at Clerk next month, and have to also mention that we are hiring, so if any of this (or any of my other values) resonated with you, please reach out and I hope we can work together 😁
