Collaboration and Coworker Red Flags

As I get old and battle against professional irrelevance, more of the value I contribute comes from finding great people to work with, whether it’s finding people within a company to work on new projects and initiatives, hiring new people, or working with external contributors as contractors or collaborators.

I don’t think I’m that great at talking to someone for 30 minutes and deciding whether they are going to be a superstar contributor, so I’ve built a mental list of “red flags” I see at the start of a working relationship. These are fairly specific, but everything on here has come up multiple times so I figured it’d be worth sharing.

1. Pirating Information - A sign of insecurity: someone asks you for help and information, and then they turn around and present it as their own knowledge in order to inflate their expertise. Slack makes it pretty transparent when this happens, especially at healthy companies that default to all conversations in public channels. But I find that it still doesn’t stop it from happening!
2. Hoarding Information - A related sign of insecurity, where someone (typically in a manager or leadership position) hoards information that would be useful to disseminate and uses it as a flimsy substitute for power earned by traditional leadership qualities.
3. Pioneering with blinders on - When someone starts at a company and wants to implement some generalized business process like analytics or testing and they just assume nobody before them has ever thought about it or done any work related to it and start from zero. There is some onus on a company to make previous work discoverable. e.g. via documentation, but the reality is that at a fast-moving company, internal docs will rarely be complete or up-to-date, and plenty of other people have managed to start at companies and be resourceful enough to figure out how things work, even with zero documentation.
4. Taking advantage of kindness - This is a bit broader, related to the game theory / war games idea of “tit for tat” or “respond in kind” where the best approach to life is to respond to kindness and cooperation with kindness and cooperation, respond to malice with malice. Most well-functioning companies are just endless positive feedback loops that rarely drift into the negative, but every once in a while I see someone who quietly starts flipping loops negative. For example: Taking advantage of permissive expense policies, choosing vendors based on personal incentives rather than what’s best for the company, etc… It might be easy to filter out abrasive a$*holes in the interview process, but I think the “taking advantage of kindness” a$*holes are much more damaging to a company because they flip positive feedback loops to negative ones.
5. Seeing work as beneath them when it isn’t - There’s a fine line between being an effective delegator and being a picky contributor. I’m still searching for a better way to delineate than “you know it when you see it.” It often feels very deliberate, like they’re worried that if they do any amount of work below them it will immediately poison their ability to move up in the org. I’ve seen it manifest as mid-level people deliberately letting progress stall instead of just rolling up sleeves and doing the work.
6. Blaming Software - “a bad workman always blames his tools” - Blaming software shows poor self-awareness and lack of resourcefulness, the idea is much older than software, but it’s worth calling out for all the different forms it takes in a tech-savvy company, here are some examples:
   • “I can’t do my job because of limited tooling” - If that’s what you think, I can guarantee that you are not understanding your job correctly.
   • “We need to <make a process worse for our customers> because that’s how the tool works.”

I know it may come off as a bit negative to call these things out, but all of the most magical work I’ve done has come from finding great people to work with. Finding a great critical mass of amazing teammates is like investing early: It can have an enormous compounding positive effect on your career.