How to Explain Your Winding Career Path to a Hiring Manager

1. Have a Target Audience, and Speak Directly to It

This is super important for any job seeker. It’s especially critical for those whose career histories involve several jobs or industry sectors. You’re not going to be able to just list out your job history (which spans sales, marketing, and business development) and expect a financial services hiring manager to instantly deduce what you have to offer. Instead, you will need to angle all of your messaging in a way that makes it obvious what you’re trying to achieve, and why you’re heading in that direction. To do this:

2. Find the Common Threads

Look for a theme that runs through several of the jobs you’ve held, and present your choices in a way that shows common threads running through each of your career decisions. For instance, in the case of my client, much of what she has done has involved advising, guiding, and helping people. This works out nicely, considering she wants to become a college advisor. And so, on her resume, we showcased several career instances in which she successfully helped, guided, and coached others.

3. Showcase Performance

People hire performers, so no matter how jumpy, windy, or unusual your career path, present yourself as a high performer. You can easily do this on a resume or in an interview by using phrases like, “Invited to…” or “Recognized for…” or “Promoted to…” or “Known for…” And, certainly, showcase your key wins and accomplishments at every position, especially the ones that you think will be enticing to your future employers.

4. Remember Your Best Defense is a Good Offense

A good rule of thumb is that, if you’re worried how a certain position or experience is going to be perceived on your resume, there’s a good chance that someone is going to make the exact conclusion you don’t want them to make. That said, you should plan to go on the offense and manage the message.
For instance, say the moves you’ve made along the way make you look, at least on paper, like a bit of a job hopper. It’s best to add a quick statement in each section of your resume that briefly explains the jump.