A few weeks ago, the director from my first gig after graduating from college (The Chronicle of Higher Education, 1995-96) sent me a quick note just to say hello, and I was thinking about how lucky I am to still be in touch with her after all these years. Later that week, I met my most recent former boss (who left my current employer in 2022) and caught up over a beer. Both have given me invaluable support and advice in my career even though I only worked for them for relatively short periods of time. 

I’m not in touch with all my former bosses, but I’m in touch with most of them – particularly the ones who managed me in roles that I think were most significant to my career development. (That’s probably not a coincidence!) But is staying in touch with a former boss always a good thing? 

When and Why You Should Stay in Touch 

When you need validation of your past work. This could mean official validation (like being a reference or writing a recommendation letter), but it could also be for your own personal validation. Here’s what I mean: Several years ago, I had coffee with my boss from when I worked at washingtonpost.com — my second job after college and the first in which I had a lot of responsibility as a staff member. We still both work in digital media so we had a lot of common professional things to discuss, but he also reminded me that I was actually good at my job back then and not the inexperienced recent college grad that I remembered myself being. We sometimes need to hear that even when we imagine we were at our worst, we were actually all right — even good! It puts a nice dent in any imposter syndrome you might be carrying.

When you need career advice. If you had a good relationship with your former boss, you probably communicated and collaborated frequently on work. In the course of that work, they learned your skills and work style, and if they were a truly great boss, they also imagined how your career would progress and skills would develop. That kind of person is perfect for giving you informed career advice, especially on how to develop your leadership skills or move ahead in your industry. They can give you hard truths, if need be, but they’re probably still rooting for your success.

To get their perspective on specific challenges. Your former boss could also function as a helpful, somewhat disinterested third party who will let you bounce ideas off of them and offer you “yes, ands” (or “no, buts”) on your thoughts. Their experience and expertise doesn’t go away just because you don’t work together anymore. (Unless you signed an NDA or are giving away proprietary secrets, in which case, ahem, do not do this!) 

When and Why You Shouldn’t Stay in Touch

If they were disparaging, abusive or harassing. Hard stop. No need to keep them in your life. No need to connect with them on LinkedIn. They are unlikely to help you in your career or act as a reference. Even if you think they’re the only person who can help, you really need to find someone else. They burned you once and will likely do it again. 

They no longer respond to your emails or messages (especially if you’ve reached out more than once). You don’t know their story. It’s possible you’ve both moved on to new jobs but they still have issues with your former workplace that have nothing to do with you and don’t want any reminders of that life. Maybe they are just crazy busy. Although this is easy to take personally, try not to. 

And for goodness’ sake: Be cool and don’t take advantage of the former boss-employee relationship, OK? Your former boss may be happy to act as a formal reference a few times in a five to 10-year period, but don’t over-ask. Nobody has the energy to write non-required emails on your behalf to a whole bunch of new positions every year. If they don’t want to endorse you on LinkedIn, don’t press it, and if they don’t want to hire you for a role on their current team, respect it. Although it’s nice when you can continue a relationship with a former boss, it needs to work for both of you. 

Random “holiday” note: After writing this newsletter I learned National Boss’ Day was earlier this week. If you know me, you know I don’t like creating marketing content to celebrate national holidays (and especially the ones that were created to support the capitalist patriarchy, as I suspect Boss’ Day was), and now that I’m thinking about it, THAT is probably the topic of a future post. End of rant.

— Shayla Thiel-Stern, Uncommon Teal