One simple thing missing in most of these replies: ask questions. Ask your boss, ask your peers, ask the CEO now and then.
- How is the company doing against its goals for the year?
- What does our runway look like?
- What signs of product success are we expecting? What are we seeing?
Note that in any company, and especially in a startup, all of these questions are rife with uncertainty and stress. You should expect these to touch a nerve, and request brutally honest answers. Leaders experience existential fear on these topics frequently, even in great companies.
In the responses, be wary of blithe positivity more than bad news. Bad news is normal; a healthy organization learns from it and improves. Optimism disconnected from reality is either an attempt to mislead you or a sign of blindness to results.
> Optimism disconnected from reality is either an attempt to mislead you or a sign of blindness to results.
This is so important. If management is continually pitching a story which you don't see reflected in the work you're doing, or the progress you're making, then it's time to think deeply whether management is out of touch with reality.
That's one of my biggest signs that it's time to leave a company. If management is ignorant to the progress of the company, or continuously gets it wrong, it's time to find yourself new management.
I definitely have had employers that basically refused to discuss such things (in one particularly egregious example, a company with 10 people).
It's frustrating, but some small company CEOs also get very wrapped up in emulating what "Corporate" looked like at bigger companies. That includes keeping information from employees, because if they knew how bad it was they might leave, word might travel to investors, etc.
Refusing the discussion is a categorically bad sign, though of course some details won't be public. Best case, the leader is deluded in a way that limits learning. Like an entrepreneur who wants you to sign an NDA to discuss their idea, this sort of behavior is now obviously bad.
Relatedly, when a candidate asks these types of questions during the recruitment process, this signals that you're clueful. A good employer will happily engage. A bad one will switch to a more gullible candidate.
Building an image as a person who's interested in the company , not just banging on their bit of code, is a really good idea career-wise. When management is thinking who to promote, the person who always seems to care about the business is a natural choice.
This is one of those things where you usually have to go through the school of hard knocks to experience the "fun" parts of working for a small company. When I was a new grad and my first job was at a company of 10-20 people, I only thought about how I'd be interacting with almost the entire company all of the time, and the idea of small, younger companies being a bigger risk to employees never came across my mind.
The warning signs I started to pick up were employee churn, company seemingly not growing in staff size as well. People found their company's practices questionable and they jumped to better places to work at. Managers were sometimes hush-hush with projects being carried out. When I worked there as a consultant, I was working on websites that most of the company's programmers, designers, and managers didn't even know existed on the agenda. I don't know if that is normal for consultant work, but this division of knowledge felt strange for a company small in size.
In the responses, be wary of blithe positivity more than bad news. Bad news is normal; a healthy organization learns from it and improves. Optimism disconnected from reality is either an attempt to mislead you or a sign of blindness to results.