A Pyramid-shaped Career

I’ve heard the worst thing that can happen to you in Vegas is winning big the first time you go. You may spend everything trying — and failing — to recreate your early success.

Getting a high-status role early in your career can limit you in just the same way. You start to associate success with status, and anything that looks like a “step down” feels like losing ground or going backward.

Fear of stepping “down”

I’ve been interviewing candidates in director and higher roles for senior EM positions. Some plainly admit they worry about taking a lower title. Others subtly keep their status centered in the conversation, trying to manage my perception.

This fear of losing ground keeps candidates from awesome jobs — ones where the team, the challenge, and the learning curve are exactly what they need.

I understand that fear because I have it too. But the industry is shifting.

As leadership roles consolidate and expectations for hands-on impact increase, climbing the ladder is both less likely and also a trap.

Growth mindset vs. role-seeking

The candidates who have navigated down-titling best seem to have a different orientation: They’re focused on how they want to grow next, not what title they want to hold.

My most powerful interview question is simple: What skills or knowledge do you want to develop next? I rephrase it a few times to make it clear I’m asking about growth. Any candidate who really understands the question passes. Many fail: They tell me what role they want to be given or what activity they want to do. They use it as a chance to tell me where their existing strengths lie.

The best candidates tell me what they haven’t had a chance to learn yet. Several of my recent hires left VP or Principal IC positions. When I asked about growth, they named specific capabilities they want to increase: technical depth, cross-functional influence, mentoring, planning, navigating bureaucracies, etc. They didn’t mention “leading larger orgs” except while pointing out how they’re not yet up to the task.

Towers vs Pyramids

Chasing status too early in your career can backfire.

Sometimes the company grows around you, and you get lifted into a key role—valuable internally, but with skills that don’t translate outside our company or immediate sector. You’re high up in one particular structure, but it’s narrow. Try to move sideways and you’ll plummet.

The alternative career path is slower at first. You don’t sprint toward short-term impact and status — you develop yourself. You pick up breadth. You grow into highly-leveraged roles but move back down to get more reps at the foundational work.

This builds your career like a pyramid – still tall but with a wide base that enables any senior role you want to grow into, without starting from scratch. You’ll overlap with more of your cross-functional peers, synthesize multi-domain concepts much faster, and have options that some people can only dream of.

If you’re trying to get rich and exit your industry quickly, this is a terrible strategy. If you’re trying to build a satisfying, resilient, multi-decade career, then building a pyramid-shaped one will serve you far better.

What pyramid-shaped careers look like

Some of the most effective leaders I work with have started companies, moved between engineering and product and design, worked the phones in sales, led analytics, ran the intern program — the list goes on.

And there’s one quality I’ve learned to look for in engineers and engineering managers more than any other: Moving into and out of management — Hopefully fluidly.

The strongest engineers I know see the business and teams through a manager’s eyes. And the most satisfying engineering leader to work with is one who has that hard-fought ability to keep pace in technical conversations with even the most senior of their ICs.

This cross-training isn’t strictly necessary for either role, of course, but in this post-ZIRP market the folks who seem to be having the most fun are the ones who can move seamlessly between roles and consistently deliver. Look at their background, and it’s obvious: They laid a broad foundation years ago.

As of this writing, the stock market just dropped, interest rates remain high, and AI is changing everything. The best, lowest-risk career strategy remains the same: build a broad pyramid of skills that prepare you for nearly anything.

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