My title is the "Vice-President of Technology", but that's mostly just to look good on a business card. I've actually been the entirety of my IT Department for most of my nearly fifteen years with the company, handling the jobs for everything from SysAdmin, to Network Admin, to Database Admin, to Help Desk, to Software Engineer (officially, my "main" role). I often get bogged down in little issues to the point where I get to do very little actual programming, but I act as a point of contact between my company and our clients and partners for anything technical (data definitions, file transfers, client portal user management, etc.).

Over the past several years, my company has been downsizing. We were at around 50 employees about five years ago, for the past few years we've been at 10 and, as of today, we're down to 8 after an employee who had been with the company longer than I have was let go for lack of work for her to do. Additionally, the company's owner and president made a decision to hire an MSP (Managed Service Provider) to handle much of the "basic" IT load that I've been responsible for managing - and, to be honest/fair, haven't always been the best at keeping up with due to all of the various responsibilities and tasks that tend to come up with little to no warning. As a part of the onboarding with this MSP, they requested admin access to pretty much all of our systems, which I've gladly provided. I've been told that the primary goal is to take those things off my plate so that I can focus on the programming tasks that have been put on hold so many times.

Additionally, the company's business model has shifted considerably from when I started. So much so that I'm not sure that they still need a full-time programmer. I'm sure that they could purchase "canned" software packages that handle some of the applications I've built over the years. They could have someone come in and do a one-time data migration to whatever retail system they chose and not have my (relatively meager for my position) salary as an ongoing expense.

All of this to ask the question: Should I ask my boss if they intend to continue my employment or if they are planning to phase me out? I honestly love working here for a number of reasons, and I've often said over the years that it's my intention to work for them until I'm ready to retire one day. However, I also fully understand that this is business. The owner and president have to make whatever decisions are best to keep the business operational, even if that means letting people go.

I don't want to be confrontational by asking such a direct question, but I also don't want to be blindsided by a "pink slip" (notification of termination) and have to scramble to find other employment to support my family. We've always had a very good working relationship - just the right blend of friendly and professional - so I don't want to jeopardize that either. At this point, I don't have any intention of leaving, but I am thinking of polishing up my resume, just in case.


Thank you all for the input. I'm not sure why this question is attracting down-votes, but I appreciate the answers and comments.

One point of clarification: The initial reduction in employees (from 50 down to 10) was due to the company outsourcing most of our data entry staff to a 3rd-party company. As I mentioned, the business model has changed over the years and what used to be our "primary" products have given way to products that don't require as much manual input and intervention. In the past, quite a bit of the data we use for day-to-day operations had to be entered and validated by one of our employees, but that's no longer the case. Most of the data points we use now are less detailed and can be handled by more automated processes and routines. That automation is a significant part of my position, which is why, I think, I've felt "comfortable" in my position and job security up till now.

  • 3
    I'd start looking for another job regardless Nov 19, 2022 at 4:40
  • @JoeStrazzere - I have to say I want to believe I'd get an honest answer due to the working relationship I have with the higher-ups, but that's probably a good question. I really don't want to leave the company. Even though I could probably be making a better salary elsewhere, the "benefits" - extremely flexible working hours, ability to take off for family "issues" with little notice, relaxed and friendly/fun working environment, etc - make this pretty much what I'd consider my "ideal" job. Nov 19, 2022 at 17:05
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    In this case -- assuming you have shills they need -- I'd be asking them if they were planning to phase the company out. Or at least what the finances were like and at what point they would have to make that decision. I'd seriously consider asking for stock options or other equity, or a raise, or both since you are essentially in the position of working for a startup, with all the risk that comes with that situation. And unless you want to take that gamble, I'd start looking for alternatives if you don't like the answers to these questions.
    – keshlam
    Nov 21, 2022 at 17:05
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    Skills, not shills, in case that wasn't obvious. Darned auto-incorrect.
    – keshlam
    Nov 22, 2022 at 2:57
  • ...or Freudian slip? LOL. Just too perfect. Nov 22, 2022 at 22:28

3 Answers 3


If I were planning to phase someone's position out, I would probably tell them so, especially if they were a useful contributor I would like to still have around. I might want to transition them to some other position or set of responsibilities. But I'm not everyone and people certainly exist who would plan to phase you out without telling you. They would have their reasons of course, like not wanting you to leave before they're ready, or not wanting competitors to know, by your presence in the job market, what their plans are.

So the question is, assuming your employers are the kind of people who would do this, are they going to tell you the truth if you ask? Are they going to set the company's needs aside in order to make you happier? Probably not, right? You might be able to read between the lines from their emotional reaction to the question, but you might get that wrong.

If you were to ask anything, I would phrase it like this:

As you know, I'd love to work here for another [10,20, whatever] years and retire from here. But I can see how things are shifting around. What do you need me to do more of, what do you need me to learn, what do you need me to take on that I haven't done before, in order to be confident I will be able to do just that?

It's pretty open ended and might produce useful information. And while I don't normally play meta games, a short contentless answer like "oh, nothing, you're fine, don't worry about that all" is probably a sign that they have no long term plans for your continued involvement.

  • Thank you so much. I feel this really gets to the heart of my question. I'm not an idiot and I can read the handwriting on the wall here, which is why I came here in the first place. I suppose I've been trying to convince myself that it couldn't happen, but it's clearly moving in that direction. I'll be happy to stay around as long as they'll have me and I don't want to make whatever time I have left "uncomfortable" in any way. I simply want to know where I stand and possibly how long I have to find something new. Nov 19, 2022 at 19:43

We were at around 50 employees ... we're down to 8

What else do you need to know? As painful as it is to acknowledge: you know where this ship is heading.

Should I ask my boss if they intend to continue my employment or if they are planning to phase me out?

There is no point in asking. At this point whatever they "intend" on doing doesn't matter as much what they "need" to do to keep the ship afloat and whether they can keep it from sinking altogether.

Look, the writing here is on the wall. If you want to ask a question you can (and should) ask: what's your business plan and data to show that the company can survive? If you get a really convincing the answer you can try to hang on. Otherwise you just need to polish your resume and move on.

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    Thanks for that. I guess I've been looking at it from the perspective that I am the IT Department, so I considered my position rather "safe". But, as in all things business, I have to realize that I'm only as safe as the amount of revenue the company is able to generate. Nov 19, 2022 at 3:03

Realistically - the writing is on the wall.

At this point, unless there is a major turnaround in the company trajectory, it's a case of When, not If.

Depending on how close you are to retiring, you may want to sit down with them and ask in relation to when you intend to retire - getting a gentleman's agreement that you'll make the transition smooth and painless from an IT perspective so long as they can let you get close enough to your Retirement age.

but at this stage, I'd be looking at my options.

  • I appreciate the input. I'm still a way off from retiring, and I would obviously prefer not to "start over" with a new company after 15 years here, but it's something I guess I'll have to give some serious consideration. Nov 19, 2022 at 17:08

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