As we wrap up Half Year Professional Development Conversation Season, it occurs to me that I have a small number of consistently useful heuristics I use to drive these chats – and maybe they’d be useful for you, too.

Professional development is slippery, right? Folks want to get promoted, they want to work on important and impactful things, and they want to feel like they’re seen and appreciated by their peers and leaders. The HOW of doing those things change across companies, but I find these heuristics really help me to show up as a leader in this calls, in a productive way.

Heuristic: Good Challenging vs. Bad Challenging

I am cribbing this from an old Cal Newport book (So Good They Can’t Ignore You I think?), and am probably bastardizing it, but the idea is this: if you want to improve in anything, professional, personal, athletic, academic, you have to work through some discomfort.

This doesn’t mean that every thing that is hard, is necessarily building your skills, and even if something is building your skills, they may not be the skills that you need to move toward your goals. There are a lot of jobs that are punishing for nearly every minute of the day, but that doesn’t mean they’re an investment in your future – I think back on my days washing dishes at Mazzaferro’s Meats (Rome NY shout out!), every day was a rough day but it wasn’t building toward something more.

Every job is going to have some aspects of plain old punishing – but in these calls I like to ask folks to weigh, is the hard stuff building skills? Are they the skills you’ll want in two years, five years? Or is it just punishing? Not all work is worth doing and a good lead will help you shift into the challenges that grow you toward your future.

It’s rare to get the bad-challenging category to zero, but it’s key to know which is which. Often what is bad-challenging for one person can be good-challenging for another – a good lead will work to balance challenges toward the folks who will most benefit from them.

Heuristic: Portable vs. Not-Portable

Let’s be realistic: you are really unlikely to be working where you work today, for the rest of your career. As much as I like everyone on my team, I don’t think we’ll be retiring together!

With that in mind, I like to ask folks, how much of what you’re doing, how much of the expertise you’re building, how much of that is portable to your next job versus highly specialized to your current job?

Like the above, you’ll never fully get away from fully bespoke here-only work – but if your calendar and growth are dominated by something you can’t talk about in a compelling way at your next job interview, it’s time to reassess.

(no tokens were burned in the creation of this post!)