The 2.5 paths to career development

In this article, I’d like to take you through three strategies I’ve either used or seen people use to advance their career. Not all of these are constructive, and which one(s) you pick will depend on personality and the amount of effort you want to dedicate to career development.

Generally, the more junior you are, the more the effort you put in will pay off in terms of promotions, recognition, etc.

Path 1: Directed Growth

I joined Microsoft at level 60, their next-to-entry-level rank. Given I’d already had 7 years in the industry (working for Silicon Valley startups), I was quite motivated to start growing. I lucked out that I had a terrific manager, Brian, who I trusted enough to have frank discussions about my performance.

After a few months, we settled into a cadence. In our weekly 1:1s (you are having weekly 1:1s with your manager, right?) I’d ask him, “Brian, what’s the one thing that’s keeping me from a promotion?”

And he’d tell me. I never asked for a promo directly. I never touted my accomplishments or demanded anything. I simply asked for constructive feedback, focusing on the topmost important thing.

Then I’d work my behindment off trying to resolve that one thing. And when Brian and I agreed that one thing was resolved, I’d ask, “Okay, Brian, now what’s the one thing that’s keeping me from a promotion?”

Rinse and repeat.

I was promoted to L61 in six months, L62 a year later, Microsoft’s equivalent of an SDE2.

And then I had an epiphany.

Path 2: Organic Growth

I figured out that a promotion is really a 5% increase in pay, and a 50% increase in responsibility/expectations. Now, I know there are people motivated by having a Principal or a Senior in their title. That’s fine, and more power to you. (Just don’t let title-chasing poison the relationship with your coworkers.)

If you’re motivated by seniority, the organic way of career advancement may not be for you. As for me, I just want to have fun. You know, enjoy my life? Sure, I wanted to make enough to afford a nice house, a nice car, and expensive toys for my kids, but if work took over my whole life none of that would matter.

At the same time, I couldn’t find it within myself to just phone it in. A third of your life is too long to spend wishing you were elsewhere. I wanted to be excited and challenged by the work I did, just not overwhelmed by it.

So at L62, which is the high-end SDE II, moving onto Senior, I developed a new approach. I started telling my managers I didn’t care about a promotion, that I cared much more about my role on the team and scope of influence I had over the product. The two are tied, of course, but they don’t have to be. That’s the key realization: my scope of influence wasn’t limited by my level, it was limited by my ability.

So I started focusing on picking tasks I enjoyed, to the extent I had a choice of tasks. I moved to teams working in domains that were fun for me (e.g. HoloLens), even if I could’ve gotten promoted faster staying where I was. And I really focused on the reason I became a developer in the first place

Amazingly, the promotions kept coming. I made senior in two years, Principal about 7 years later. Even though at my first 1:1 with a new manager I’d always say those magic words: “I’m not promo-motivated. I care much more about the work I do.”

This approach does rely on having a good manager who genuinely has your best interest at heart, and can recognize and reward value when he/she sees it. If your manager doesn’t do this, run! No, really. Switch teams. A bad manager can poison your life.

A brief aside

Let me tell you about one direct I had. He was a Senior Engineer hired into the organization around six months back, and he wasn’t doing well. His enthusiasm was waning, his output was low, and he was in the typical downward spiral that may have resulted in a PIP (performance improvement plan) if unchecked.

I had an opening on my team for a senior engineer, and after talking to the guy, came away with the impression he wasn’t being utilized well and that he’d do better on my team. So I hired him. (Naturally, he went through all the prerequisite interviews, talked with my team, and got nods all around.)

A couple weeks into his tenure, I observed something. He was trying very hard to show the team how good he was. He was obsessed with making sure his contributions were visible and appreciated, and stressing out over the scope of his tasks being in line with Senior-level expectations.

I mentioned this to him in our 1:1, and said “I think you feel like you need to prove yourself.” When he agreed, I asked him “Why did you go into computers in the first place? What made you want to do this, instead of, say, becoming a cop, or a lawyer, or a doctor?”

He told me of his love as a child of tinkering with code, of solving problems, of watching something he created come to life— the usual reason good software engineers go into the profession. I told him something then that made tears stand out in his eyes. I’ll never forget this moment — it was one of the most transformative moments in my career as a manager.

I said, “Forget all this stuff about proving yourself. You don’t need to — we all already like and respect you. Focus instead on why you love writing software. Focus on that sense of wonder you had as a kid, playing with your first computer, writing those first few lines of BASIC and seeing them run. If you do that, everything else — success, growth, career advancement — will come.”

That’s what I call the organic way of career development. Why? Because when you truly love something, you will naturally get better at it. It’s that simple.

(P.S. The guy in question was promoted to Principal within the next two years, then became a manager, and has now far surpassed me in both technical and managerial skill. Was that due to my talk with him? Hell, no. But maybe I played a small part in helping unlock his potential.)

Path 2.5: The Cynical Path

Looked at it in a certain way, every task you undertake falls somewhere within the following triangle:

Impact: how valuable your contribution is to the business

Effort: how difficult it was to implement

Visibility: how aware the rest of the organization is of your contribution

We’ll explore this triangle more in a future article, but for the purposes of Cynical career growth path, the idea is to maximize visibility while minimizing effort. That’s it, really. I’m sure you have people in your org doing this. They’re the ones chasing after politics at the expense of the team. The ones taking all the credit. The ones snuggling up to their skip-skips.

And they get promoted all the time. Assholes.

Why? Because when a manager reviews a list of candidates for promotion, their eye is naturally drawn to the names they recognize, to those whose accomplishments they remember. So by having visibility at that level, you are greatly increasing your chances at a promo.

But you lose the respect of your colleagues in the process.

Don’t do this. Don’t be like the assholes.

But… there’s a way to chase after visibility without undermining the respect of your colleagues. And it, again, comes from truly loving what you do.

You are very loud, Eugene

One of the most interesting pieces of positive feedback I ever received from my manager was, “You are very loud, Eugene.”

What he meant, was this: every time I found something cool on the net — say a new tool, an approach, some nifty language construct — I’d share it with someone. Sometimes (roughly once a week) that would take the form of a team-wide email — “Hey, check this out, it’s helping me do X…” (It’s also one of the approaches to the Somebody Else’s Problem scenario — also in a later post.) Sometimes I’d just call a colleague over and show them.

Or, say, I got some feature working that hadn’t worked before, or even just fixed a difficult bug. I would be so excited by having it work, I’d call my manager, or my PM over, and say: “Hey take a look at this, what do you think?”

Now, I wouldn’t be doing this to crow. I’d be acting out of the same reflex you have when you want to share a movie you love, or a book you adore, with people you care about. It’s a simple motto: “if you’re excited about something, share it!”

That had a tangential effect of greatly increasing my visibility on the team. Every time my manager saw one of these emails from me, he’d smile… and then reward me in the next performance review.

The line of abuse in this approach is simple: if you’re doing it to get visibility, don’t. That’s when your emails start looking like spam, or self-aggrandizement, and you’re right back to the Cynical path.

But if you’re doing it because you’re genuinely excited and can’t wait to share your excitement with others, 99 times out of 100 the email will be well-received.

There you go, and necessary disclaimers

Hope this was useful. If I were to boil all this down to a sentence of advice, it’d be:

“Love what you do.”

Because if you don’t, why are you doing it? For the money? There are easier ways to earn money than beating your head against the monitor day in day out. Life is too short to spend it doing things you don’t love.