The Ugly Truth About Your Employability as a Manager

🙋‍♀️ This is a cross-post from my newsletter, Leading by Design. If you liked the post below, consider subscribing! I (usually) post two issues per month.

Photo by Sean Musil on Unsplash

Photo by Sean Musil on Unsplash

I’ve been writing and speaking about transitioning from an individual contributor to a managerial position for quite some time now. I’ve talked with numerous people who contemplated the switch but were conscious of their future options. It’s time to settle this: will moving to a management position make you more desirable to employers?

Sorry to be the bearer of bad news, but switching to a people management career can (and will, if you let it) harm your employability. You will have access to fewer jobs. It might seem counter-intuitive, but after years in a management position and two years coaching leaders, I’ve witnessed it unfold repeatedly. I see people happily making the switch, thinking they are advancing their careers, only to find it challenging to find their next position quickly and reliably.

I’m not the only one voicing that particular concern either. Charity Majors puts it succinctly in her now classic “The Engineer/Manager Pendulum”: “Your choices shrink. There are fewer jobs, with more competition, mostly at bigger companies. (Do you even like big companies?)”


Managers are less employable

Start-ups prefer to hire generalists

The start-up life can be super rewarding, but where do you fit in as a manager?

Unless you’re a generalist with deep technical expertise who is not afraid to get down and dirty with work (way) outside their job description, you won’t easily fit in a start-up. Most early-stage start-ups don’t invest much in people development, as they struggle to ship work and get from 0 to 1. Everyone that doesn’t serve this objective will be considered an operational overhead.

The most important managerial skills you’ll use while working in an early-stage start-up are hiring and managing yourself. Everything else will get left behind.

Scale-ups prefer to promote internally

When needing a new manager, most companies prioritise promoting an existing team member instead of bringing new people in. There are multiple reasons why this happens.

First, a management position can often be a reward for existing employees who have completed their stretch goals and want to advance their careers. In most companies, you can only climb the org ladder by switching to management. People management is a chance for senior team members to expand their skills.

Moreover, most senior company employees will know the company DNA better than you, a stranger. People shouldn’t get promoted solely based on how long they’ve worked in a company, but the truth is that the longer you work in a team, the more valuable institutional knowledge you collect. These people will be first in line for that management position.

Finally, internal promotions are usually more budget-friendly. Hiring good managers is expensive, and many companies don’t wish to get caught up in a prolonged hiring round that will cost them time and resources.

Good managers are highly contextual

The success of a manager depends on where they work. For them to be thriving, it means they have the autonomy and trust they need to do their best work. Switching companies means rebuilding valuable stakeholder relationships from scratch; often, manager onboarding can be slow and clumsy until they gain the team’s trust.

A manager is successful when the organisation they work for is also booming. Even if they’re effective and empathetic and exceptional at what they do, their portfolio will look weak if the companies they had helped scale throughout their career crashed and burned after two years. That’s even more dire if they were on the executive team when the crash happened.

There are fewer managerial positions

It’s just a numbers game. You need more sous chefs than chefs in a well-organised kitchen. You need more developers and designers than middle managers to create software (in fact, some might argue that you don’t need middle managers at all). You need more salespeople than sales managers to drive a sales boom.

When you’re a manager, the employer pool you can look to for your next position gets narrower. Most companies don’t need people managers until they’re well into their growth phase, so you have to focus on teams of a specific size and up. Gone are the days when you would wake up to tens of recruiter messages on LinkedIn. Manager jobs tend to be few and far between, and they heavily rely on referrals.

What can you do?

I have painted a bleak picture of the job market so far. Management isn’t always the career graveyard I described, especially in tech, where options are (still) abundant.

Here is my advice if you want to go after a management position:

Preparing for your search

Before searching for your next management gig, reflect on what you’ve accomplished so far. Take the afternoon off, prepare your beverage of choice and answer these questions truthfully:

  • How did you empower your team to do their best work?
  • What systems or processes did you implement to ensure the team met or exceeded its objectives?
  • How did you approach individual team member development, and can you share a success story?
  • How did you manage and lead through periods of change or uncertainty?
  • Was there a time when you had to mediate a conflict within your team? What was the outcome?
  • How did you recognise and reward excellent performance within your team?
  • How did you enable and support change?

Remind yourself of how you’ve helped your team move forward and succeed. Check the previous 12 months in your calendar and review your and your team’s latest performance reviews. OKRs can significantly help with this process as they help quantify your objectives, which can often feel vague and abstract for a managerial position.

Invest in your portfolio & visibility

When you’re a manager, you spend your days attending meetings and writing documents. You speak to people, you write to people, and that’s it. On good days, you can see subtle signs of change happening. On bad days, you feel exhausted by 5 p.m. and can’t pinpoint why.

How do you assemble a portfolio when your work is “People”? If you’re a developer, you’ve worked on essential projects or maybe on a fun side project idea or two. When you’re a designer, your portfolio is a visual representation of your talent. What does your portfolio look like if you’re a manager, however?

To prove your worth, you should invest in storytelling. Based on your answers to the questions above, describe how you’ve driven change in your current employer. Describe the ways you’ve empowered your team to do their best work, as well as all the ways you’ve shown strategic thinking. Emphasise challenges and how you solved problems by managing up, down and across.

A manager’s portfolio is more likely to be a simple slide deck than a fancy website or a pixel-perfect PDF. How you present your work will get you hired, not necessarily the work itself.

Going back to individual contribution

This gained much traction in tech during 2023, especially after the 2020-2022 whirlwind, the extensive layoffs in big tech and the collective burnout. Managers started returning to individual contribution jobs to combat burnout and improve their positioning in the market.

That might seem like a demotion to the ambitious mind, but it isn’t. As Charity Majors says, switching back and forth from individual contribution to people management might be the most fulfilling way to play out your career. It’s a great way to keep your contributor skillset up-to-date and strengthen your position in the job market. In addition to that, having management and leadership skills is a significant benefit, even if you work in a contributor role.

You don’t have to pigeonhole yourself into a narrow idea of how a career should look like. Even if you successfully switched to management, it doesn’t mean you have to be a manager from now on.

The beauty of squiggly lines

I read a fantastic article recently, one of those I wish I had written myself. In “How To Opt Out Of The Career Ladder”, Jean Hsu explains that our careers shouldn’t necessarily be a hockey stick graph. That is a concept that Hellen Tupper also explores in her book “The Squiggly Career”. Why shouldn’t we think that careers could span different roles, industries and locations?

Avoid thinking of management as another checkbox in your career checklist. I’d advise everyone to take up a managerial gig at least once, but once in, you don’t have to stay in forever. Find the job that best aligns with your principles and priorities for that particular moment, and have fun.

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