September 26, 2018.
A peculiar challenge of management is trying to invest in someone's career development when they themselves are uncertain about their goals. As a manager, you may have more experience and more access to opportunities within the company, but that represents a small slice of someone's career possibilities. Our schooling often rewards us for being methodical, linear thinkers, but that approach is less effective outside the intentionally constrained possibility spaces.
The options for approaching a career, particularly for those of us priviledged to work in technology, are so extraordinarily vast that exploring them effectively requires a different approach. This vastness also means that you, as a manager, can't simply give folks a career path: you'll inevitably steer them towards the most obvious avenues and through avoidable competition.
Flipping perspectives, it's also quite challenging to plan your own career. I sometimes find myself walking from one meeting where I'm coaching someone on their career goals, straight into a second meeting where I struggled to string together words to articulate my own. The hardest bit is that most folks are always at the furtherest point in their career, each change a step into the unknown, with limited visibility into the upcoming opportunities that their company can provide.
The intersection I've found between the individual's and their manager's perspective is the career narrative. I've mentioned these fabled documents a few times before, in Roles over rocket ships and Partnering with your manager, but given how useful they can be, it's useful to expand a bit on the process of maintaining one.
If you took ten minutes to ask a dozen folks about their immediate career goals, I suspect that for eleven of them it would center on either getting promoted or switching companies to reach the next evolution of their current job. This doesn't mean that climbing the career ladder is bad, that's what it's designed for, but it has the side effect of funneling most folks towards a constrained pool of opportunity.
What I've slowly but increasingly come to believe is that there is much more opportunity outside career ladders than within them, and by including those opportunities you'll make and feel more progress. Better yet, you'll find far more opportunities to partner with your peers, no longer competing for limited promotion slots.
For example, if your long-term goal is to be the head of engineering at a mid-size company, you could approach that linearly by trying to expand your role bit-by-bit at your current company on the track to becoming its head of engineering. That'll work for roughly one person at the company, but for everyone else pursuing that same path it will probably be suboptimal.
A different approach would be to instead work on identifying your gaps to be a strong head of engineering, and then start using your current role to help fill those gaps in. A prototypical head of engineering will be skilled at organizational design, process design, business strategy, recruiting, mentoring, coaching, public speaking, written communication, have a broad personal network, and have a broad foundation from product engineering to infrastructure engineering. That's not even a particularly complete list of relevant skills! There are so many different aspects of to build out, and you can find opportunities to practice all of them in your current role; no need to convince yourself your current role is holding you back, everything you need is here.
Importantly, while generalized career paths won't necessary align cleanly with your goals, they also are unlikely to take full advantage of your strengths. While an important part of setting your goals is developing areas you're less experienced in to maximize your global success, it's equally important to succeed locally within your current environment by prioritizing doing what you do well.
With all of this in mind, take an hour and write up as many goals as you can for what you'd like to accomplish in the next one to five years. Then prioritize the list, pick a few that you'd like to focus on for the next three to six months, and share it with your manager to discuss at your next one-on-one.
Once you've identified goals to pursue, the next step is to translate those goals into actions, and this is where your manager can be a leveraged partner in interating on your career narrative.
Managers tend to have a strong sense of the business' needs, and that gives them the superpower of finding the intersection of your interests and the business' priorities. That translation is a creative pursuit, so don't leave this entirely to your manager: participate as well! Brainstorm projects, research how folks at other companies have pursued similar goals, educate your manager on aspects of your goals they don't know much about (for example, engineers often have more conference speaking experience than engineering managers).
Bringing your list of goals to this discussion helps ensure it's successful. If you don't bring a rough draft, by default you'll get steered towards the contested commons, and your career narrative will be a dull instrument for progress.
This refined list of goals, aligned to your company's priorities, then becomes a central artifact for how you and your manager partner on your career evolution. Every quarter or so, take some time to refresh the document and review it together.
If you're unconvinced it's worth your time to write a career narrative, you certainly don't have to write one Most folks get away without writing one for their entire career and have deeply fulling careers despite the absence.
That said, if you don't, then there is probably no one guiding your career. Chasing the next promotion is at best a marker on a mass-produced treasure map, with every shovel and metal detector recovering the same patch. Don't go there. Go somewhere that's disproportionately valuable to you because of who you are and what you want.