Ask Maynard: How Do I Tell If There's Opportunity Within My Company, or If It's Time to Move On?

Thanks for all of your great comments to my last post on How to Ask for a Promotion. And thanks for the questions that have extended the topic further, such as the one I’d like to help tackle here. 

“In the case where you actually do not get the promotion you deserve how would you effectively go search for a position in other places while being at your current job? Also, how and when should the conversation for resignation occur after you have obtained a position that you want in another company? — Antony Zhong, Cyber Security Enthusiast  

Dear Antony,

This is a complicated question because so much of the answer is tied to the specifics of your work environment. Do they value candor? Do they value transparency? Will they want to know if you are unhappy? Is there enlightened leadership, or not? You will need to do an honest assessment of how your company and organization works and then determine how to proceed. 

If your organization values candor, you should initiate an honest discussion about your concerns and your willingness about doing your part to address your concerns. Generally speaking, this is also the right thing to do. In almost all cases, being honest with your boss about a disconnect in how she or he sees you and how you see yourself is a good discussion to have. It will help everyone gain clarity. 

Of course, if you start this discussion in a threatening way, it probably will not go over well. Therefore you should approach the situation by initiating a dialogue about your potential at the company. If you do not see eye to eye on that, you should talk about ways for you to improve in order to help you achieve your career goals. If these cannot be reconciled, at least you’ll know where you stand from your boss’s perspective. 

Do not be intimidated to do this. It’s taking the high road. If you’re worried that your employer will fire you for airing your concerns in an honest fashion, that’s a problem. Determine whether that fear is justified or if it’s you holding yourself back. If you think your fear is justified, then you may want to consider moving on. 

You also bring up another age-old issue — how do you search for a job while still employed? 

It’s tricky — especially if your boss doesn’t know about your concerns. You have to assume it’s a small world and if you’re out interviewing, there’s a pretty high potential for it to get back to your employer. This is why I advocate having that initial discussion. 

Additionally, before you begin any search, you must really think about what you want in this next opportunity. Write down the criteria that matters most to you (the day to day work, the people, the short and long term economics, the work environment, the work-life balance) and compare what you currently have against any new opportunities. Don’t chase 15 jobs; be strategic about picking a couple of suitable opportunities. 

Be discreet as you go through the interview process. Don’t slack on your current job — commit to doing everything extraordinarily well and impressing your current company. 

When you do receive an offer, do not play one employer against the other. You should know what you want and be ready to accept the offer or stay where you are.

If you’d like to resign, do so with grace and dignity. People have long memories and new employers do reference checks not only with the references you give, but with any references they can find. Make sure you give enough notice and leave with everyone feeling as good as possible. 

As always, send me your questions in the comments, and I’ll try to help. (Don't forget to upvote the questions you like the best.)