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The last time I posted was 2 years ago, but it feels like 20. In the meantime, we built Looksharp, worked our asses off to build up sales, had a lot of fun, cried a non-zero amount of tears, and then sold the company in February 2017. And that’s really where this journey began (again).

Finding a new place of employment sucks. It’s one of the things I dread most and one of the things I think I’m worst at. But I decided this time would be different. This time, I would be really selective, assess fit across several key criteria, and find my one true love — errr, new job.

So I asked the same questions that I’ve used when determining which customers my sales teams should focus on:

  • What am I great at?
  • Not great at?
  • Where are my advantages?
  • Where can those advantages be leveraged in a way that is of maximum value?

To my surprise, the process worked. Flashy opportunities that were poor fits were exposed as such. And the opportunity that I ultimately selected was, on its face, kind of a snoozer. But as we all know, that’s where the gold is.

So, without further ado, here’s a tech veteran’s approach to job hunting.

Green Flags

I must see these three things.

  • Product market fit: The market has spoken and people want this company’s product. Don’t confuse this for having a great a sales team or market momentum. When the sales keep coming no matter what, you can mess up a lot of other things. All things being equal, product market fit is the single most important characteristic of success.
  • Sense of mission: Everyone is communicating the same core message and believes strongly in it. This is usually a sign of great leadership and creates virtuous cultural benefits.
  • Happiness: Pay close attention to how you feel when you engage with people at the company. How do you feel when you leave an interview? Could you imagine hanging out with them outside of work? I can’t believe how numb I was to this criteria before. If you don’t like the people, it’s going to drag you down.

Yellow Flags

These aren’t deal breakers, but more than one would be an issue.

  • Multiple bozos: If you come across more than one person who is clearly worthless or a net-negative contributor, that’s not a trivial finding. It’s usually a sign that the leadership, usually the CEO, is afraid to make difficult decisions. Not good.
  • The quality of the office space: Bottom 5%: You’re probably looking at a company with overly cheap, or weak, leadership. Middle 90% Nothing to see here, move along. Top 5%: The vast majority of the time, companies with extravagant offices spend themselves to death. I avoid early stage or high growth companies that spend too much on office space and/or meals.
  • Focus: If your potential role — or any other major element of the company — feels unfocused, monitor this closely. You can overcome a lack of focus, but it’s a bad early indicator and probably isn’t isolated to a single area.
  • Spending like they’re drunk: Did they just raise a round? Are you part of some huge cattle call of hires? How are they spending their money? If it feels foolish, it probably is. Most startups die because they run out of cash, and spending like a drunken sailor is a good way to run out of cash, fast.

Red Flags

If you detect any of these, run.

  • Institutional arrogance: If the CEO, or anyone who interviews you, thinks they can do everyone’s job, get out of there. You shouldn’t be made to feel like you’re lucky to get an interview or an offer. Sure, the place may be a rocketship — but what a crappy ride it’s going to be.
  • Technical debt: This is one of the hidden icebergs that most people don’t think to look for. Technical debt is what happens when a dev team, for any number of reasons, puts band-aids on medium-to-major technical issues instead of dealing with the underlying problem. Over time, this “debt” can snowball and become a bigger and bigger problem until all this debt must be paid. Immediately. And it’s painful. There’s an easy way to assess this: reach out to a developer (present or recently departed) and take them out for a beer. Nine times out of 10, they’ll give you straight answers. Bottom line, you don’t want to work at a company that has accrued enormous technical debt. This is doubly true if they don’t have strong technical leadership — which brings me to the last red flag.
  • Weak or nonexistent execs: A bad CEO has trouble recruiting and retaining a strong executive team. When interviewing for a VP-level position, I would never take a job without meeting at least one executive (other than the CEO), and I’d be very unlikely to be a CEO’s first executive hire.

Finding the right job is never just about the job. It’s about the company’s purpose and the product, leadership, and relationships. It’s about the way they approach big challenges and daily decision making. 

So the next time you find yourself in search of a new gig: know what you’re looking for, ask the right questions — and be picky! You’ll thank yourself later.