I have been wanting to have a career mentor for couple years. This year our (software) company is starting a mentoring program.

I have two topics that I think I need help in developing my career, and I'm wondering if these are good topics to work with a mentor, or could they raise red flags in HR or my management chain?

  1. How can I train myself to get more resilient to face the stressful situations like barely making (or missing) deadlines, working with spaghetti legacy code and occasionally missing an undocumented assumption or code path, leading to several bug tickets. The stress and anxiety that I feel is in the form of "OMG did I screw up badly this time? Is my job on the line because of this?" thoughts.

  2. In my discussions with my manager I get hints that I'm on the path towards being a technical leader (architect) of our product. This is all good and exciting, but there is a chance that this product may cease to exist in a decade or two while I'm in the middle of my career. I may need to move on to another product in our company or industry that is quite different from the current one. How can I improve myself to face such a situation? What transferable skills in our company/industry can I train myself in, so that when such an event comes to pass I will retain at least some of my value?

  • What exactly is the question here?
    – Socrates
    May 1 '15 at 21:12
  • 2
    To me it sounds like your concerns are wanting to do your job well and wanting to make sure that your skills are relevant to the marketplace. Neither of these IMO would raise any red flags to HR or management.
    – Robbie Dee
    May 1 '15 at 21:45

The first thing you need to keep in mind is that if the firm has started a mentoring program, its purpose is to help you sort out the kinds of issues you mention. What else would a mentoring program be for, unless you believe it's some kind of trap to get people to expose their weaknesses?

That being said, your first point:

getting more resilient to face the stressful situations...

concerns nothing but how you can execute your current tasks more effectively and become a better employee. If that's not something to take up with a mentor, what is?

Your second point:

How can I improve myself to face such a situation...

is not quite as straighforward because it doesn't directly concern your current career trajectory with the firm, but is dependent on several "what ifs" which would have to materialize for your concerns to be at all relevant.

So on that point I'd say hold off on delving into the subject with your mentor until the good news arrives that you have been promoted to the position of technical lead, and then you succeed at that post. At that point you'll be in a position to be worried about "what's next" and have something important and relevant to discuss with a mentor. (Assumming you still need one then - which you may not.)

Regardless, it doesn't seem like a good idea to say to your mentor "I see this job coming to an end and I'm probably going to have to move on..." Assumedly the purpose of the mentor is to help you further your career in the firm, not to provide you with a personal career coach.


I started a mentoring program this year, and I'll say that among the first topics in our first session was - "exactly how far does the right to privacy extend?" It's not that either my mentor or I are particularly paranoid - but both of us understood that when it comes to confidentiality, you can't fix a breach in trust - we both wanted to trust that conversations we had that involved frankness wouldn't hurt our careers or our trust with others.

Both of us were willing to make the commitment that we wouldn't share anything that seemed potentially damaging without talking it over with the other.

But we both felt better having actually agreed explicitly.


One of the useful things to ask a mentor is "if I have these interests and goals, what skills should I be developing/demonstrating to advance my career in that direction?" In other words, if you aren't sure what to ask, it's legitimate to ask for help with that too.

Ideally, you'd want a mentor who is at least few steps farther along the path you want to follow, so they can give you personal experience as well as theory... and so you can get a view from that level of what's likely to become important next.

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