Bosses can fall short in a lot of ways. While your intuitions might clue you in to some failings, others are very difficult to spot. My advice would be:
- Do the others on the team seem happy? Did you get to meet any during the interview process? Do they seem to be happy to work there and comfortable in the environment?
- Does everyone seem to get quiet or smile officiously around the boss? That's a big warning sign. It probably means the boss is a bit of a tyrant or maintains an unhealthy power differential with the team. There is absolutely no room for this kind of posturing in a startup.
- Do you witness anyone coming to the boss for help with something? If so, and if the boss responds in a positive way, it's a great sign. A good boss is someone who is there to help everyone succeed and lend expertise when asked.
- Does the boss say anything disparaging about the other team members during the interview? Look out for indignant, judgy sorts of comments that indicate that the boss feels shortchanged by the team he/she has (unless you are explicitly being hired to single-handedly turn the team around).
- Is the hiring manager, founder, etc., transparent about runway, the cap table, and turnover rates? Playing it close to the vest about any of the three is a very bad sign.
- Do you see any VCs or investors stopping by uninvited and just hanging out? If so that's a good sign and means there is transparency with investors (which doesn't happen in all startups).
- Are there "big company sounding" organizational titles like "Senior Director", "Senior VP of x", "Senior Engineer", etc? If the company has fewer than 200 employees, titles like these indicate a wide array of culture problems, usually starting at the top.
The last point can be unreliable, so use your own judgement. At my current company people make up their own titles, so we have a "Vice President of Engineering" and a "Chief Alcoholic".
Those are fine, I'm referring to the minor gradations on each role, as in Senior Manager Level 5, etc. Those are necessary in large, bureaucratic organizations where working one's way up a predictable ladder is the goal. In a startup, anyone who is more concerned with his/her title than with experience and results is likely better suited for a large, bureaucratic company where those HR-concocted titles are respected.
It depends how titles are used. If an organization has totally transparent comp and strives to link it with well-understood titles, it may make sense.
I'd much prefer a team where everyone's merit is judged by their day-to-day contribution rather than by the title they negotiated during the hiring process.
Titles can be hand-wavy things at best even in large companies. Currently working for a large multinational company, and looking at the org chart makes my head spin.
Even the people in my own team have wildly different titles.
- Do the others on the team seem happy? Did you get to meet any during the interview process? Do they seem to be happy to work there and comfortable in the environment?
- Does everyone seem to get quiet or smile officiously around the boss? That's a big warning sign. It probably means the boss is a bit of a tyrant or maintains an unhealthy power differential with the team. There is absolutely no room for this kind of posturing in a startup.
- Do you witness anyone coming to the boss for help with something? If so, and if the boss responds in a positive way, it's a great sign. A good boss is someone who is there to help everyone succeed and lend expertise when asked.
- Does the boss say anything disparaging about the other team members during the interview? Look out for indignant, judgy sorts of comments that indicate that the boss feels shortchanged by the team he/she has (unless you are explicitly being hired to single-handedly turn the team around).
- Is the hiring manager, founder, etc., transparent about runway, the cap table, and turnover rates? Playing it close to the vest about any of the three is a very bad sign.
- Do you see any VCs or investors stopping by uninvited and just hanging out? If so that's a good sign and means there is transparency with investors (which doesn't happen in all startups).
- Are there "big company sounding" organizational titles like "Senior Director", "Senior VP of x", "Senior Engineer", etc? If the company has fewer than 200 employees, titles like these indicate a wide array of culture problems, usually starting at the top.