Recently I was approached by an old co-worker and good colleague to consider re-joining a place we used to work together. I pretty much declined and probably offended him a bit (sorry!) but it really got me thinking about which opportunities I’d like to take vs pass on.

Maybe this view comes from a personal bias. Surviving cancer definitely sharpens the focus. There is more time for family and friends, and more time for meaningful work, but less time for money for the sake of money. Can’t take status to the grave with you!

Here are a few dimensions to consider, when joining, or re-joining a company:

  • What’s the purpose of the company? is it about solving a burning problem, or an insurmountable challenge (good), or is it about the greatness/legacy of the owner, or a advancing a particular favored method/technique (bad), is there any clarity at all? is any of this backed by measurable actions (very important)

  • What happens to the people who leave the place? Do they become more or less successful? Do super-stars ever return? Actions speak louder than words, people may simply be polite and avoiding speaking their mind… choosing to instead speak with their exit. Can you reach leavers an LinkedIn and get them on the phone to get the “real” exit interview?

  • What’s the money like? This one is kind of U-shaped: on one end you have grift-startups with charismatic founders, on the other places with no soul that pay top-$$$. For the grifting startups, they’re unable to really raise enough money, so they descend into sweat-shop mode – paying the staff the bare minimum and going the cult path. On the other hand, you have ultra-high paying places that solve problems by just paying you more to shut up. Some people need the money, because circumstances and reasons. In the middle, you should get places that are the best: they pay a lot but not insane. Discount startup stock completely: you’re already 100% exposed and it’ll be years before you see stock option profit, if at all, and you can always get more of it later down the road.

  • What’s the competition like? This one is U-shaped again. Too much competition is clearly bad, but no competition at all may mean that it’s too soon, or simply a hermit-like organization.

And the most important one of all

  • What’s the progress for the money and time spent? What’s the bang for your buck? Given an estimate spend of an organization, and they years they’ve been around, what have they actually accomplished? Was it something truly relevant to their claimed mission, or an improvement (however ingenious) on the periphery? Under-performing on this dimension is an indicator of real problems, especially when backed by enormous resources: things are probably too screwed up internally to make any real progress. Could be leadership, could be team, could be everything. Typically this is not a failure mode available to startups, unless they go zombie mode.

This is probably not exhaustive but it feels good enough!