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My former employer had to let me go but encouraged me to seek employment with one of his clients -- a small, well-funded company with maybe 100 employees -- since I had done extensive work for them before being laid off. I have an upcoming interview with the CEO of the client company whom I have never met, but I have concerns about the company's management style.

While working with the client, I observed:

  1. frequent fire-fighting by other employees instead of resolving the core issues
  2. choosing to out-source a critical part of their flagship product to a less-experienced team instead of allowing us to complete it despite repeated significant failures we observed (and kindly pointed out) when collaborating with the other team
  3. frequent changing of project requirements due to lack of planning
  4. poor communication among employees and stakeholders

I've worked with both small and large companies and have seen some of these problems manifest before at times, but my concern is that these reflect the top-management style and are not rare occurrences.

Should I bring up any of these concerns to the CEO? If so, how do you recommend I approach this? I obviously don't want to cover these point by point as I'd probably come across as overly critical.

I'm being considered for a senior position, and as such, may have some sway in suggesting some positive changes if the CEO is willing to listen. Normally, I wouldn't consider working for a company while having these concerns a priori, but they would be offering me the benefit of part-time work which I'm seeking and is rare for my position.

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Yes, it is appropriate to bring those up. Those problems are going to come up anyway if you work for them, and if the CEO can't handle some probing questions during the hiring process that's something you should know about ahead of time.

One tack you can take: since you are being considered for a senior position, you will probably want to prepare a plan for e.g. your first 90 days. You can include proposed solutions to these problems in that plan to see how the CEO takes it.

  • 1
    That would be important to know. I think I'll limit myself to one question that gets at what I believe underlies #1, #3, and #4. Does this question sound okay? “I know your company has grown very quickly. I can imagine that it might be challenging to work towards future long-term goals while handling the day-to-day pressing needs of existing clients. I guess I’d be curious in knowing how well you feel that you’ve found that right balance and what you’d like to change as you anticipate future growth?” – rimsky Nov 29 '16 at 5:32
  • Prepare for the counter-question: Why are you asking? ;-) – Jan Doggen Nov 29 '16 at 7:33
  • That is an easy counter-question: Because I have ideas to help you with it. – skymningen Nov 29 '16 at 12:44
  • @skymningen A better answer would be: Because I believe this is where I could add the most value. – toadflakz Nov 29 '16 at 15:37
  • @rimsky: that sounds very vague to me. If you ask that I would be prepared to get an answer which doesn't actually answer your underlying question. – Xodarap Nov 29 '16 at 20:48
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  1. I never criticize my employer's operations unless I have some corrective action worked out. And I make damn sure that I have the full picture before I do any criticism. Nothing destroys your credibility as a professional faster than you launching yourself into a criticism session of the Other on the basis of partial, incomplete information.

  2. There is a thin line between critiquing and criticizing and that thin line can be vanishingly thin. If you don't know the difference between critiquing and criticizing, the chances are pretty good that you are going to cross that line without realizing it and when you do, all hell will break loose. Keep in mind that people can be VERY thin-skinned about being criticized. Especially when they are in the habit of criticizing others heavily - the fact that they can dish it out doesn't mean that they can take it.

  3. An unsolicited critique from you of your prospective employer's modus operandi can easily interpreted as criticism and if the interviewer deems your criticism as partially or wholly uninformed, there goes your candidacy for the job. In my judgment, you have part of the picture but you are a long way from having the full picture of what's going on with the client. Try not to talk yourself out of a job with that client.

  4. People have been fired for being right including myself. You don't know the interviewer, so you can lose on your candidacy for the job even if you are 100% right. People will take criticism but maybe not at an interview when they are the ones interviewing you.

  • Those are great points and I've up-voted your answer. I guess I'm wanting to know if my concerns are valid or not before I start for a few reasons: - To know what I’d be getting myself into - To learn what management is doing to address the issues - To get a sense of how well management is willing to listen. I think I’d prefer to broach the subject by stating my primary concern as a question, such as something like I suggested in my comment above. Hopefully, it comes across more as a reasonable, genuine question rather than a critique or criticism. – rimsky Nov 29 '16 at 5:39
  • While all this is correct, I still think the OP should at least bring up one or two of these topics, in the form of questions. It might be that the company lacks some senior personnel to enforce a better working style, because the CEO is overwhelmed, and that they're interested in the OP precisely because they think that's what they'd be getting from prior experience. It might also be that bad management is a trickle-down effect from a thin-skinned pig-headed bozo. Interviews work both ways, let the OP find out which it is :-) – George M May 15 at 21:50

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