How or why will your career progression stagnate?

Career progression

The above image is courtesy of this post.

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 No. 1 and try to avoid stepping in No. 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:

Career progression advice

What else you got on career progression?

Ted Bauer


  1. I was reading a Nick Corcodilos blog recently (I usually value his perspective, he routinely calls out crappy HR and recruiting practices from the standpoint of a recruiter), and decided to look up what he thought about “job hopping”. I was actually pretty dismayed to read a post he put up from 7 years ago ripping apart those who would job hop—a piece that was essentially a response to an argument by Penelope Trunk advocating *for* job hoppers and an affirmation of another business blogger’s rant *against* job hoppers.

    Corcodilos’ “moral” was to “stay put” because job hopping “looks bad” and sorta regurgitated the whole “we can find out if you’re a job hopper” mantra that I often see recruiters repeat (without really demonstrating how), and use one’s personal connections to find work in which one can stay put at. Pretty intellectually vapid argument from a guy who is otherwise very intelligent, as it isn’t really based on any logic I can discern other than “um, some people who run companies don’t like instability, so, uh, I guess try to not be unstable”.

    While I agree with Corcodilos that searching for work through personal connections can be preferable to throwing your resume and cover letter into the abyss, I still don’t see how the distaste for job hopping a lot of hiring managers/HR bloggers complain about is congruent with what appears to be a trend of companies that are disinterested in training and retention. If the argument is that employee turnover costs money, well, then, OK, but that needs to be made transparent. If the argument is one of preference of the hiring manager or HR jockey that is then amplified through use of the blogosphere, then hold up a sec. The root of the claim is a preference for stability, yes? Not all hiring managers/HR types espouse this belief, despite what a blogger may want you to believe (because they asked 20 of their buddies what they thought, and that sample size is apparently enough to validate their “study”). The mere fact that Penelope Trunk and Nick Corcodilos can disagree on what is essentially a matter of preference (and each make valid points about their ideas) is indicative that there are differing worldviews in the workplace, thus job hopping is not objectively a bad behavior (though I don’t doubt there are people who do it without tact and grace).

    While writing all that, I got to thinking—isn’t job hopping the individual’s inverse way of doing what companies do when they downsize due to cost-cutting measures? The individual is trying to maximize their personal profit, just as the company is in their own way, while ignoring (or downplaying) the human side of the transaction. Both provoke strong reactions: companies tar and feather job hoppers, individuals take to Glassdoor to rip apart companies with poor employee retention behaviors. There is an important power asymmetry, of course—a company can absorb an individual or two leaving better than an individual can getting kicked to the curb by a company—which is why job hopping as a stigma is so distasteful (to me, at least). It’s also somewhat disingenuous to chide someone for looking out for themselves when many companies are pretty much doing the same thing nowadays anyhow.

    All the rambling aside, I say: If you’re a company whose leadership generally values loyalty and stability, be transparent about that in your recruitment message and materials and look for those people when hiring (long term strategy). Develop them throughout their tenure, even if their career development costs you money at the expense of some other ultimately frivolous balance sheet measure (short term results).

    IF, however, your company is about short term results, practice the inverse, but maintain transparency in your hiring. Pursue the job hoppers, people who can drive short-term results, full well knowing you may lose them in a year or two.

    Either way, don’t try to have your cake and eat it too. Identifying and articulating your values might sound like a silly way to spend your time, but knowing who you are as a manager and organization will help you find the people you want to work for you. There’s no need to label and demean those who have made a deliberate career choice; all that needs to be done is to learn what you like and don’t like and not BS people when you’re building a team.

    Cheers Ted and thanks as always for your thoughts.


    • “Know who you are as a manager and organization” is so rare, though …

      • Sadly. I don’t know what it will take to convince some folks they need to engage in activities that will help them divine that, if at all. We’re working on that at my office, I’ll keep you posted.

  2. Dan D: I am a manager who has had a change of heart around job hopping. A lot of times contractors are the job hoppers but they know how to ramp up quickly and get stuff done. I decided after my last horrible job that I would not stay somewhere if I hate it. It sounds obvious but I was following the “don’t job hop mantra”. As a manager, I felt like it was my duty to give them a set amount of time.

    I do want to hire and retain people. Culture is everything to me and I want team players who are not jerks on my team. People first, then team, then company. That is the best way to serve our customers. I want to go to work and enjoy the work I do with my team. If I can’t do that, what is the point anyway.

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