I'm a senior engineer in a small, but regionally established, IT company. I perceive it as rather hard to make progress due to a lack of transparency, coordination, and organizational structure; in fact, we are a group of individuals with decent technical skills, but with largely uncoordinated efforts.

I think that similar problems can be found in many (IT) companies; small company founded by a technical person who neglects his managerial tasks as far as possible. It is not a terrible workplace, but I am actually looking around for jobs that might provide a better environment. I recently had an interview with a company (startup, ~30 people) that has sounded rather interesting for my line of work, salary would be above average, stock options, and the first interview was positive.

In the first session of the interview, I got to talk with the engineering team I would work with (two people, aiming for 6-8 till the end of this year). They seemed skilled, smart and kind. They warned me that the team had shrunk from 8 to 2 mostly due to frustration about mismanagement. However, they were positive about recent changes: CTO and founder is replaced by project managers, a CEO was hired to get the management work done.

In the second session, I spoke to that CTO and founder. I noticed afterwards, however, that I had learned nothing about the company culture. When I was cautiously asking about the engineers that had left the team, he briefly mentioned that one or two of them had actually just changed team (rather than leaving the company), and changed topic.

When I asked about how communication works across teams and across locations (two), the relevance of my question seemed to be unclear to him and the answer went along the lines "they use Skype etc".

My conclusion was that he was friendly, and probably a good engineer too, but certainly not a good manager; as indicated by the engineers.

I told recruiter that the structural part of interview felt too vague to me to make sure this would be an improvement over my current job. I am afraid to end up in a mess, requiring long hours and other unnecessary stress factors that can be caused by bad planning.

They have now offered me another interview with the CTO/founder so that I can ask more specific questions about my concerns. Now I am wondering about what I should ask specifically to get a good picture. Roughly, I would like to get clarity over issues such as:

  • HR: goal setting, feedback culture, hiring process
  • transparency: do I get the information I need in time in order to do a good job
  • expectations: what does a typical day look like?
  • management: how do they work now, how specific are the announced changes, how open are they for changes coming from the engineering teams?

Is there something like a Joel test for management/organizational issues?

I feel like there have been many signals that indicate that it might be as messy or even worse than my current job. On the other hand, I don't want to wash away a potentially good job opportunity because they are not easy to find: good engineering team, good product, funding, growing potential for the company and myself.

Any tips on how to get the best information out of that talk?

  • What do you mean by “CTO and founder is replaced by the project managers?” I am guessing “CTO has fired the project managers and temporarily is doing their jobs” right? Cause you said you are going to interview with CTO, but A replaced by B means : B is in charge now and A is gone (which I am guessing you didn’t mean that, right?)
    – Iman Nia
    Commented Feb 17, 2020 at 17:36
  • 1
    Does this answer your question? What are specific ways to learn meaningful information about company culture in interviews?
    – gnat
    Commented Feb 17, 2020 at 18:42
  • The question is too long with too many details, please edit to make it more readable Commented Feb 17, 2020 at 18:56
  • @iman the CTO is replaced in the sense that he should no longer manage projects himself.
    – Chris
    Commented Feb 17, 2020 at 19:22

3 Answers 3


You're handling this exactly right, by persevering in getting your issues addressed.

Here's one suggestion. There's stuff you don't like about your present job. Describe some of that stuff, in general terms, and ask whether this other company has similar problems and how they might cope with them. Be vague about which company you're describing. For example,

I worked at a place where I had great co-workers, but we somehow weren't very effective as a team. For example (give a real example here), Carl and I worked on the same problem without knowing we were both doing it. If we'd known, we'd have worked together and come up with a better solution faster. I put a high value on good teamwork.

Do you have problems like that here? If so, how do you address them, and what do you need from somebody like me to help build teamwork?

Another question:

What are your biggest concerns about your development organization these days, and how do you address them?

A third:

It sounds like you're planning to do more hiring. What's that process like? How do you expect me to help if I come work for you?

A fourth:

I'm interested in the company's culture. What's the vision of you and your co-founders about the culture, and what are you doing to make your vision into reality?

or maybe

Your help-wanted web site describes your company's culture as blah blah yadda. What can new hires like me do to help strengthen that culture?

Any of these questions would be a great conversation-starter about your concerns. The point is the conversation and what you learn from it, not boilerplate from a hiring FAQ. Be patient, because this kind of stuff is always a work-in-progress, especially in a young company.


At a startup this early stage, the only thing that matters is the individuals you'll be working with. Focus only on them, and if you feel you'll work well together.

Things like organisational structure and culture don't really exist yet. To the tiny extent they do, you'll have an instant and ongoing huge influence on them anyway when you join.

For example, communication - you'll be working with 2 other engineers, so just communicate with them however works best, even differently with each individual. There aren't crystallized norms around this stuff in a small startup. Generally nobody will tell you what to do, you set your own norms.

So, onto the individuals:

I got to talk with the engineering team... They seemed skilled, smart and kind.

My conclusion was [the CTO] was friendly, and probably a good engineer too, but certainly not a good manager; as indicated by the engineers.

On the surface, this isn't great. You should weight the founder much more than a peer: 1 bad founder comfortably outweighs 2 good peers at face value. It's net negative.

If I were you, in the further talk with the CTO I'd focus on getting as much a sense of him personally, and the way you'll work together, as possible. See if you leave with a better impression. If you don't, weight that highly in your decision to join. Once again - in a startup it's all about the individuals.


You are looking for big company processes and structures in a place that clearly is too small to have them. I work in a bigger company than the one you are describing and most of their processes are make it up as we go and violated on a daily basis. I had a job recently at one of the largest global IT companies and boy did they have processes. They had about 3 managerial staff per developer, sure it was great that the test team had all the responsibility of production faults, but I'm not sure I enjoyed that environment more over my current

  • I agree with the two ends of the scale you are sketching. However, being a startup too often serves as an excuse for neglecting best practices in management, and I believe that this is often the cause for startups to fail in a growing phase. Finding the right trade-off between being flexible and having a strategic vision that goes beyond the next day (or sprint, in agile terms) is important for long term success. Long term might not be relevant though if your strategy is to sell the company for a good price quickly, but that does not create a sustainable work environment.
    – Chris
    Commented Feb 17, 2020 at 21:15
  • 1
    I'm not here to tell you what's right or wrong, you are correct, my answer is a reflection of reality not utopia
    – user114216
    Commented Feb 17, 2020 at 22:44

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