This Is Why You're Stuck in Middle Management

By Steven McConnell, writer
Nov 14, 2017
Image Credit: Pressmaster/Shutterstock

Is your desire to be liked undermining your career?

Not long ago, I was chatting with a friend about his new job. And he couldn't say enough about what a great person his boss is: "So fun to work with. Really caring and flexible."

But when I asked more pointed questions about his leadership style, it turns out that this great person is really not that great at leading. He flounders in decision-making when under pressure. In fact, he's actually holding himself (and their whole team) back. The conversation ended with my friend lamenting, "He's a cool boss in many ways."

So it got me thinking. A desire to be liked and accepted – to be "cool" – is a very normal, understandable human condition.

But at what point does that desire begin to undermine our career? Well, let's start by taking an honest look at your behavior.

  • Trying to be cool might mean that you have to be friends with your staff.
  • It might mean that you need to popular more than you need to be effective.
  • It might mean that you have difficulty making tough decisions.

And it might mean that while your employees like you a lot, they may not respect you as a leader. They might even feel you're in their way (case in point with my friend). While acknowledging that possibility may be painful, if your people like you more than they respect you, the perception is contagious. Chances are that senior executives aren't taking you seriously, because they know you don't have the chops to lead.


The good news is that if you have some of these behavioral tendencies, all is not lost. It's possible to change your approach. Don't get me wrong here. Becoming a jerk isn't the answer, either.

Consider Dale Partridge's story. Dale ascended in the startup world quickly and in his mid-'20s was running a highly successful, profitable company with 40+ employees. He thought everything was going swimmingly well.

Then his mentor pulled him aside and gave him some shocking feedback. His take-no-prisoners style was insulting and alienating the very people he needed to be 110 percent behind him. There was a huge rift in the ranks.

Dale needed to find a way to adjust his style. It demanded rigorous internal work. Self-examination. Willingness to admit fault and change.

What Dale thought was cool, in fact, wasn't. But once he did the work to become a mindful, authentic leader, he became a cool boss for real. He was equipped. He now helps other leaders of startups be their best. With Dale in mind, let me ask you, "Why do you want to be a leader?"

Is it power? Prestige? Family pressure? If any of these are driving your career choices, perhaps you're conflicted about leading. And if you're conflicted internally, how you show up externally won't be authentic. Or effective. It definitely won't bring you happiness. So, if you're not loving being a leader, I urge you to examine why you're doing it.

If, on the other hand, you're leading because you have a specific career goal that requires the support of other people, fantastic. And if you're leading because you love to help others realize their career aspirations, more power to you.

How, then, do you get unstuck? 

Try this simple, but powerful, technique.

  • Notice when your desire to be liked (or to avoid criticism, or to keep peace at all costs) overrides your ability to make critical decisions.

  • Whenever that aspect of your personality emerges, refuse to let it run the show. Take a step back and remember your purpose as a leader. Act with sincerity and certainty from that purposeful place.

Observing your own behavior, pausing and correcting your course will elevate you above the realm of trying to a cool leader into being one. One who has vision, chops – a leader who makes the tough calls yet cares passionately about their people. Your subordinates might not like all of your decisions, but they'll respect you. And so will the people who have the power to promote you.

I'm a digital marketing wingman to bootstrapped startups; I specialise in helping them grow from $100K to $5m in revenue. Currently, I'm the Marketing Director at Arielle Careers and the business has grown on average 350% every year for the past 4 years.
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