What's Gonna Derail Your Career?

What's Gonna Derail Your Career?

If you believe automation is coming for 1 in every 2 jobs (it may well be), then perhaps career progression doesn’t matter a ton long-term. But for the short-term, it definitely does. People often have defined career goals , but it’s a murky path through to them right now. Employees want to be trained , but oftentimes employers don’t want that (it’s a cost, after all). When they do offer training, it’s often low-impact BS led by HR.

The final elephant in this family room is the role of job-hopping. That’s often the only way to make more money these days (i.e. career progression), but we still have a stigma among HR reps that if you job-hop, you’re somehow a “loose cannon” or something. It can paint people into corners. Combined with generally awful hiring practices , we create an ecosystem where many companies miss out on the absolute best person for their role — often because of some antiquated HR belief. Sad.

Most of the above was the organizational side of a career arc. Now we come to the personal.

As people move through a career, though, they also have “derailment periods.” These are aspects of personality or working style that can push your career progression in the wrong direction if not managed. And what are those?

The five aspects that derail career progression

Carter Cast is a business school professor at Northwestern and wrote a book on “how brilliant careers are made and unmade,” so he seemingly knows his stuff on career progression and arc. He did a podcast with Northwestern’s Insight page, and here are his top five career derailers at the individual level:

  • Relational issues with other people (by far the biggest hit to career progression)
  • Can’t hack it as a manager after being a good employee
  • Clinging to what you know instead of growing
  • Very good at execution; no clue on strategy
  • Over-commit and struggle to prioritize

All seem fairly logical and I’m sure you’ve all seen people experience all five. Let’s go one-by-one quickly.

Relational issues with people

Yep. A lot of people end up being assholes at work, because they’re chasing relevance for themselves as opposed to anything else. In reality, work is (still) made up of humans, so what matters are concepts like gratitude and friendship. Most people think the KPIs and deliverables matter. If you push the people to the side, though, work becomes a much bigger zoo.

Can’t hack it as a manager

All too common: 82 percent of managers end up being the wrong hire. The simplest problem is two-fold. First, we promote off execution (see below). Execution can be ruthless and efficient, but it doesn’t mean you know how to relate to others. Then you manage others and the whole thing blows up. Second: most people only want to become managers because it’s the only way to make more money. They don’t want to manage people or take on responsibility; they’re doing it for the money. Often, it’s the only compensation path they can follow. When you become a manager and don’t want to be a manager, well, it doesn’t usually end well.

Clinging to what you know

Normative nowadays, as many chase retirement and ignore concepts like “digital disruption.” This is actually maybe the most annoying part of white-collar work these days: there’s so much potential for advancement and new ideas, especially around metrics , but so many “decision-makers” are using 1991 methodology because it’s all they understand.

Don’t understand strategy

Also somewhat normative.

Can’t prioritize

… and ditto.

The elephants in the career progression room

This is literally all relative to organization. At some places, you can cling to what you know for 20 years and get promoted 11 times. That’s why “relational” is so important. If you have relationships with the right people within your organization, none of the other four matter that much. You will eventually get minted even if you don’t understand strategy or would be a terrible manager. We have all worked for this guy. No clue on priority, strategy, and hides behind portals instead of having conversations. Every new idea is “No, we’ve always done it this way.” How did this guy get up the chain? Because he did the relational part well enough, or he stuck around long enough and they had to put him somewhere. This is middle management personified.

How can we improve career progression?

I’m a terrible person to ask, because I’ve never really been great at the whole “jobs” or “career arc” thing. My parents probably spent $30,000 on my kindergarten and now I mostly take conference calls in an undershirt. I wouldn’t say I’m killing it at the life game, you know?

But here’s what I’d argue:

  • This is an individual-level concept, not an organizational one.
  • (Most organizations probably don’t care about your career progression, unfortunately.)
  • “Look out for №1 and try to avoid stepping in №2.”
  • Try to make decisions that make sense at the time.
  • No decision is going to be perfect.
  • “Skate to where the puck is going.”

And then maybe this:

What else you got on career progression?

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