Questions you shouldn’t be affraid to ask your boss

One of my favorite topics lately that I’ve heard on a few podcasts is about job changes and career choices.  There is so much to take into account in looking for a new job or evaluating an opportunity that you weren’t looking for.  It’s been fun to hear people help others realize their potential and direct them to job options that they never thought they would qualify for.

I get email from recruiters almost weekly for open positions.  Over 90% of these jobs would be taking a step backwards in my career, and not by a single step. I’m not sure what they’re search methods are but these recruiters need to do a little leg work before contacting potential candidates.

A friend recently contacted me about an open position that he felt I was not only qualified for but would love to be in and able to grow within his company.  After a few texts and emails I finally took his call so I could hear about this <sarcasm> “once in a lifetime” </sarcasm> opportunity.  It turns out the position would allow me to do a lot of the tasks that I used to do and really miss.  Things I used to do at my current company. Before I went to a VAR and realized I didn’t like a fair amount of what was required for my position (you never know until you try).

I’ve talked with a couple people that I really trust as to whether I should take this job opportunity or not. Anyone who follows me on Twitter knows there are a lot of annoyances where I currently work.  I’d classify them as annoyances as each of them in their own right wouldn’t make anyone want to leave the company.  One of my good friends finally said, “If you like that other position so much why don’t you ask your boss if you can be put into the same type of position where you currently work?”  Huh?  What?  You mean that is allowed?

I thought about what my friend said and decided to look into it.  Then I looked at the team that was currently labeled to do the same type of work within my business unit.  Once I did, though, I found out that they didn’t do that type of work anymore, and haven’t for almost two years.  They were spending all of their time doing financial analysis on how the company could cut back instead of actual architecture work.  I didn’t want to do that (neither did the other 4 who left the team already) so I didn’t ask the question.

Another side story to this was that I was “promoted” to a new “role” on a new team to do the same type of work that I’ve already been doing for nine months.  They wanted to make a presentation our of my promotion a couple days ago, at the same time I was deciding if I was going to accept the job offer above.  I didn’t want my current boss to do a presentation for this promotion for me to turn around in a few days or weeks and resign.  I felt the right thing to do was to ask for some time, which I did.  He really appreciated what I did.

The fallout was that a couple hours later I had my boss and two higher levels of management asking me to stay.  They asked what I would be doing at this other job.  Once I told them they responded with “We really don’t want you to leave. We’re forming a new team to do that here and we’ll move you to it now.”  Wait, what?????

They’ve been talking about a re-org to a new model for over 12 months but there’s been little to no movement.  I talked to one guy on the “IT Transformation” team for 15 minutes one day but that was it.  I had no idea what was going on, where they wanted me to fit within this new model (which ended up being the team they tried to promote me to) and when it was going to be implemented.  Lucky for me I now had the proper people to ask questions of.

For the next 30 minutes I was able to ask them anything, and I did.  It was great to not only hear managements responses to my questions but see their body language when answering.  It became pretty easy to tell when they were confident in their answers and when they were trying to convince themselves as well as me, which is helping me make my decision.

Here’s a list of things I felt I needed to ask to help me decide if I should stay or take the offer above:

  1. I don’t like the current role I’m in.  Can I move to a role somewhere that allows me to do XXXX???  Be specific as you may not know where else in the company that people do that type of work.
  2. Are there any organization changes being planned that may change what I currently do or allow me to do something different?  What is the time frame for these changes to be implemented?
  3. How confident are you in the current management (all levels) to move the department/business unit/company forward?
  4. Does the company have enough talent to fill the positions needed to complete the transition?
  5. Is the company going to financially back the changes they are implementing?  (Especially if the answer to #4 is no.)


In my case there is a lot of changes in organizational layout and processes planned.  These changes will require all business units to change the way they interact with our systems and people.  It’s going to take a large army of very good people at a lot of levels to get it done.  I have more on this but this post is already WAY too long.  Maybe I’ll add them into the next post which will contain my decision on whether to stay or go.  🙂

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

Website Powered by

Up ↑