On Tech Career Development Conversations That Suck Less.
“So, what do you want?”
When I was an engineer, there were few conversations that I dreaded more than the career development chat.
This piece aims to provide a frame by which to tackle career conversations in a way that’s investigative, hopefully less shit, and factors in the myriad diverse ways that which people have an answer to the above question. If you’re a manager, I hope some bits of this are helpful and add to your toolbelt. If you’re reporting to someone, then I hope this provides a frame by which to have those conversations.
So, here we go. Let’s go for a walk. Coffee’s on me.
A General Artifact
I do career planning sessions professionally, and also as a (free!) community service. I’ve done 73 of them over the past two months. Most of those conversations are captured in an artifact that looks roughly similar to this:
To be honest, the formatting doesn’t matter that much — we care about the individual components. Translated, it looks like this:
I use the same artifact so that it lessens the cognitive load on myself; if the artifacts have a common pattern, then it’s easy for me to play back what the previous conversation was about. I currently have 25+ direct reports, which makes cognitive load a very important, finite resource.
More importantly, I do this because goal setting is always composed of four things:
A.) the goal
B.) an honest assessment of the current reality
C.) a timeline
D.) the way forward.
(See also: GROW model, or The Inner Game if you like Tennis.)
1. Setting Goals
On overarching goals and dates.
So let’s break it down. “What do you want?”
If you’re very lucky, you’re going to have two answers to this: what that goal is, and when the person wants to reach that goal.
But us managers aren’t so lucky sometimes. A lot of people won’t have a clear idea of what they want in the long run (god knows I don’t) — but good news: specificity has a direct relationship with the proximity to the current now. While someone won’t have a clear idea of what they’ll want in say, three years, they’ll probably have a clearer idea of what they’ll want in a year. And clearer still, six months from now.
So if you don’t get a clear answer, try dialling back the timelines. Try asking: What do you think you’ll want in six months?
On framing conversations and attributes.
Video games ate my brain, so I like to use RPGs as a way to explain framing goals. Simply put, there’s generally three ways that I’ve seen people plan out career aspirations — which is roughly analogous to the three ways that people create characters in Dungeons and Dragons.
A.) Through an idea of a person you’d like to be. Dungeons and Dragons sometimes comes with pre-made characters that you can play — each with predefined attributes. This is very similar to how some people do career planning by focusing on the person (or persons) that they’d like to be.
In this case, we start by listing out all the things that the reference persons do: What does the person that you admire do well? What are they good at?
B.) By choosing a role that you want to play. But sometimes, people want to be able to fulfil a role (e.g., I want to play a leadership role for the team). In DnD talk, this maps to when people decide that they want to be a healer, or maybe a tank.
Once that role is identified, we start listing out the specific attributes of that particular role: What does a Team Lead need to be good at to be described as effective?
C.) Or by focusing on what you want to be able to do. Once you’ve spent some time playing DnD, you might get into power leveling. This means focusing on what you should be able to do (“I want to be a glass cannon wizard!”), and fitting the skills and attributes according to that goal.
In career planning terms, this turns the conversation into investigating how to tell if you’re good at that specific activity. What should you be able to do that would prove that you’re good?
One of the few times stack ranking is a good thing.
Unfortunately, we gotta pick favourites.
This is as simple as stack-ranking the priorities according to which is the most important to the career planner, relative to the goals and the timeline provided. And then you limit those to an arbitrary number — mainly to allow for focus.
One cool side-effect of this is that sometimes, people develop a better idea of their role aspirations once said priorities are laid out. The priorities of an individual contributor are different to one of people managers, like so:
On Alignment (optional).
An extra step is necessary for cases where career progression and promotion along organizational frameworks is the main goal. While I personally do not believe in hard-cut competency requirements to advance in your career, your organization might. In this particular case, it’s helpful to use the above as a way to remove ambiguity about what is expected of you. Which qualities define a senior? And which one is the most important?
2. Honest introspection and self-assessment
On scoring as a start, but not as an end.
And so we get to the hard(ish) part, which is an honest look and inventory into the current reality. Where are we now, relative to the goals?
I use a simple scoring system — where 1 is not-good-at-it, and 4 is the ideal state of where people want to be at their chosen timeline. It looks like this:
Keep in mind that the scores are not an artifact as much as they’re a conversation piece. You ask for people’s self-assessment, and interrogate why they’ve settled on that number. The answers are often enlightening, always critical.
On things to sniff out for.
“Why do you think that?” is a question I often ask during the self-assessment phase. The answers are varied, but there’s ones I keep an eye out for.
A.) “If I compare myself to X, I’m nowhere near…”. While setting goals is important, making sure that the benchmarks that we measure ourselves against is realistic is critical. There’s incredible potential for anxiety and burnout if we set our bars a little bit high.
In these cases, it’s healthy to recalibrate. A lot of people (myself included) frequently fall into a hole of overestimating what people know vs what I don’t. I like this diagram:
B.) “I just wish I had an opportunity to…” Sometimes, people just need a chance to be able to do things outside of their current work pattern. The action here is to find opportunities for the career planner — and perhaps in the long term, coaching the career planner on how to look for said opportunities.
C.) “I just don’t know if I can do it…” Confidence is a tough one — but can usually be broken down into a question of raw competence versus an internal assessment thereof. The former can be supported by indexing on things that improve a person’s skills — the latter, through providing smaller environments by which to practice, where people are safe to fail.
3. Generating actions
Neat! So now comes the hard part: which is collaborating on what actions people can take to take themselves from their current state to their goal. Thankfully, there’s a couple of things I’ve learned to lean on over time.
On learning modes.
I personally buy into the VARK model. Simply put, people have a learning style that they generally lean towards (and not necessarily exclusively):
- Visual, where learners generally absorb information when it is presented in, for example, pictures, charts, or demonstrations.
- Auditory, wherein learners prefer listening to what is being presented, like say, backseat pairing.
- Kinaesthetic, where the learner prefers being “hands-on” with the subject matter (say, driving in a pair).
I’m not particularly interested in what people’s personal styles are — I use this more to generate ideas on what people can do to grow more in their particular chosen trajectory. What do you think of being able to whiteboard our system of work? Would working on a pet project be a good exercise for you?
On why limits matter.
You don’t have to generate a lot of squares. In fact, I think it’s usually better when your plans are capped:
A.) You reduce the cognitive load imposed on the career planner, and allow for focus. Having too many things on the board might present someone with an exhausting, intimidating to-do list — capping to a couple of goals at a time sends the message that no, we don’t have to do everything at once. We’ll just focus on these for the while, and that’s totally fine.
B.) You allow for flexibility. Plans change and that’s okay. We make assessments of what to do and where to go, based on the information that was available at the time. But people’s preferences change, and if we’re lucky, we discover new things that we love or are passionate about.
Over time, I’ve found that to be one of the best outcomes of this exercise. Because at the core of it, all we’re doing here is helping people articulate what they love to do, why they love it, and what they need to do to be able to do it more.
In time, people develop the ability to ask these questions of themselves. And that’s always neat.
Why care?
A person will always do the best job that they can with the time provided, the resources available, and what they know — so an individual’s growth increases the net maximum of what they’ll be able to accomplish. And one of the core aspects of our (managers) job is to be able to interrogate what a person needs to develop, at the right time, and be able to provide that for that need if appropriate.
That’s it, really.
[Note: If you feel like you want to chat about your career goals and need someone to bounce off over coffee, feel free to hit me up through my Twitter or LinkedIn]
