Ryan Caldbeck's site

There is a lot written about what to look for in new startup employees, from values & traits to experience. I personally value integrity, work ethic, intelligence, pride and teamwork. I value true startup experience so that the person understands both the ups and downs of startup life. There are certainly benefits to coming from larger tech orgs (such as pre-IPO Coinbase or Airbnb), but having true startup experience is invaluable. 

There is less written about predictors of failure. None of those listed below are guaranteed, but like the traits and experience previously mentioned, each is relatively highly correlated with failure in my experience. To be clear this is correlation, not causation, but I’ve seen enough reps now to have it impact my behavior and hiring going forward. I wish I knew these indicators on my first day as CEO as they would undoubtedly have prevented me from hiring some people or stopped me spinning wheels trying to keep someone that was clearly going to leave.

Time between offer acceptance and start date >1 month– “My current employer needs me for 6 more weeks” or “I just want to travel a bit before I start — I’ll need two months.” Whatever the excuse is, I have found there to be a very high correlation between a later start date (>1 month since acceptance) and that person either not joining or not lasting at the company for six months. If the average time was less than 1 month, I think success (defined as person employed >1 yr) is 90%, if gap time >1 month that plummets to <20%. 

Commute time– This may be less relevant in a post-pandemic world, but pre-COVID if someone’s commute time was >25 minutes on a daily basis, you could probably assume they have a 50% chance of being with the company in a year. For every additional 10 minutes of commute time you can drop the percentage by 10-15%. This implies that those commuting for more than an hour have no chance of being at the job in a year — I’ve found this to be pretty accurate. There is a lot of data on the inverse correlation between happiness and commute time. Granted, my experience is heavily influenced by the Bay Area where there are a ton of options for other startups that will be closer to your home if you have a long commute. It should be noted that the average commute in the US is 25 minutes each way, but I think at startups in the Bay Area people aren’t willing to tolerate long commutes. Too many options.

Lack of friends at work– My co-founder once found data that said the best predictor of happiness at work was having a best friend at work. We also found data indicating that if someone hasn’t made personal connections at work within the first 10 days, their retention goes down dramatically. Without friends at work the job is less enjoyable — which makes the inevitable downs of a startup harder but also makes the ups less fun. We found that a buddy system for the first few months, along with scheduling 1-2 coffees a day with other people across the org over the first 10 days, really helped build relationships early. 

Sitting in the corner– I’m close to undefeated in predicting when someone is going to leave a company. Perhaps that’s a self-fulfilling prophecy (if the CEO thinks you will leave…), but a tell-tale sign is if the person frequently isn’t working at their desk but is instead sitting in a corner by themselves with their back to the wall. Or sitting in the corner during an all-hands, purposefully away from the team. To be clear, as someone with ADD I definitely need to escape, to not have distractions around me for any deep thinking. I’m talking about patterns of someone physically distancing themselves and frankly just seeming checked out. I remember an employee who was a senior member of the team who tried to sit as far away from the speakers at all-hands as possible. There was a pole in the middle of the room and this teammate would always try to get a seat that was behind the pole, ensuring that he was completely disconnected from what was being discussed and presented. He didn’t last long.

Whispering– In 2017 we had a new employee join us and immediately a previously healthy team began to “whisper”. What is whispering? Talking about others in a negative way but not to their face. Talking at a level so that no one can hear, and then obviously changing the topic when someone new walks up. We’ve all dealt with that either in high school hallways or political organizations. 

This new teammate led the whispering. For the first and only time in our history, about a dozen employees voiced concerns that they always heard whispering when they walked by that individual’s team. Whispering that would immediately stop when they passed by. The whispering was an indication of a bigger cancer — politics that this person was injecting into the org. They needed to go.

“Not what I expected”– A new employee sits down with the manager in the first few weeks with a sigh and says “this just is not what I expected.” Some version of this phrase is a great indicator that the person isn’t a fit. Few people ever directly say “it wasn’t on my job description”, but these are the types of employees that want life to be on rails. They want their role to be exactly what was on some magical JD and they want the company to have no additional warts — both when they join and any that come up later. They want a job. That’s it. More than once I’ve wasted hours trying to talk this type of person through the benefits of staying at a startup and coaching them to lean into the rollercoaster. Subsequently, I have always regretted doing so. It’s a massive investment of time that ultimately leads nowhere. It not only takes your eye off more important issues but also keeps someone that is a net negative around to influence the emotions of other teammates. I like to joke that the word startup is French for “dynamic and constant change” (it isn’t) – people who are looking for things to stay the same aren’t a good fit.

Note that if you consistently hear these types of things from new employees, that may be an indication of ineffective communication with new candidates in the hiring process that needs to be addressed.

>10 yr career with no startup experience- I’ve talked before about why I value startup experience. For me, an anti-pattern is someone who is more than 10 years into their career but has focused solely on larger organizations. That person has made conscious decisions to lean into safety and lean out of risk. Have people successfully flipped onto startups more than 10 years in? Yes. But as with the other indicators on this list, I’ve witnessed a strong correlation (not causation) between this bucket and not surviving at a startup for long. 

When reading this list, it is fair to raise the correlation vs. causation flag. There are times when I care about that difference, but this is not one. I have found the above to be strong leading indicators that it won’t work. Whether they are the driver or a byproduct of something else probably depends on the person.