I Change Bosses Like I Change Underwear

A leadership blueprint you can use to excel in life.

Tim Denning
Oct 8, 2020 · 7 min read
Photo by Keyvan Mansouri on Unsplash

It feels like I change bosses like I change underwear. If I look back on my career it’s full of different bosses. They step into my life, and more often than not, step right back out of my life.

Most bosses don’t last. It got me thinking: why is that?

Then there are bosses who survive the test of time. Even when they’re not your boss you stay in touch with them. They start out as a boss and transcend the title, quickly, without even realizing it.

There are two types of bosses: those who serve themselves, and those who serve others. The second category is rare — understanding why can change how you approach your life and your work.

Here’s how you can think about leadership even if you’re not blessed with the title yet (but you can be).

Dare to Be the Least Important Person in the Room

The typical boss wants to be one, to feel important. The title helps them fill a void in their life that they never filled during childhood. They carry this burden through their entire life, silently.

A void in your life can force you to seek attention.

The good leaders I have worked with don’t try to be important. Instead, they make you feel important. It’s a subtle difference.

When you’re not trying to be important you behave differently towards others. You go from “how do I make this initiative at work help me look good” to “how do we achieve this initiative.” See the contrast? The need to feel important changes how you act, and therefore, how you achieve outcomes.

If the outcome is to be important then the results will be terrible.

I once worked with a leader who always wanted to be the least important person in the room. He had a shiny, bald head so when he was in a meeting room the fluorescent lights would reflect off his head. This strange phenomenon was a metaphor for how he acted. He shined bright under the fluorescent lights because he knew how to shut up and listen.

Seek less importance to shine brightly.

Deal with Your Insecurities

Insecure bosses make terrible leaders.

They behave badly to cover up their insecurities rather than lean in to them. It’s normal to be uncertain about capabilities. In fact, uncertainty is powerful. You can analyze the areas you’re uncertain about and seek feedback.

You can see your flaws and then outsource them to your team.

As a leader, I suck at spreadsheets. I don’t try and cover it up or go all red whenever the budgets are due. I just admit I am an idiot with numbers and have someone in the team do it for me. You don’t need to know everything.

You can be perfectly stupid in multiple skills and still lead.

If you don’t deal with your insecurities then they will eventually be your downfall. You’ll do everything you can to cover them up. The typical way a boss covers up their insecurities is by blaming or destroying the lives of other people.

This strategy runs out of rocket fuel really fast. Eventually, the trail of devastation is too great and the insecure boss loses their title and their sense of self-worth. Some bosses recover and learn. Other bosses try the same battle plan again and keep losing their entire life.

Don’t cover up your insecurities.

Get to Know People Through Stories

High-performing leaders are storytellers.

You can’t skip stories. Stories create bonds.

I worked with a boss once who was always straight to the point. They would never get to know you or ask you what you did on the weekend. They didn’t know anything about your family or even what postcode you lived in. They couldn’t name your partner or define what your hobbies were.

Nothing was personal. They never shared a story with you from their life. They never wanted to hear your stories. As a result, without stories, the leadership bond was never formed. They could talk but nobody ever heard them. The glue that is stories was never used to make a connection.

So people “did business” with them but never understood why. As soon as a crisis struck they were the first one to be told “sorry we don’t need your services anymore.” They couldn’t understand why.

People want to hear your stories. Otherwise they don’t understand you.

Schedule Less Meetings

Bosses schedule lots of meetings to check in with their fear. The meeting is supposed to calm their nerves and take a temperature check on their direct reports’ loyalty.

Too many meetings is a waste of time. The purpose of a meeting isn’t to stroke a person’s ego; it’s to get sh*t done.

There are meetings with outcomes, and meetings to make bosses feel better. You can just fix yourself rather than schedule a meeting. Here are some books to help bosses get over meetings:

  • Unf*ck Yourself
  • Man’s Search for Meaning
  • Unlimited Power
  • Love Yourself like Your Life Depends on It

If you know a boss, send them this reading list. Because god only knows we don’t need any more Zoom meetings to attend.

Trust Your Team

The root of the problem. If you trust your team then they will do the work you need to keep your job. You might even find you like coming to work and being a leader. Trust builds teams. Lack of trust destroys teams.

Bosses don’t trust teams because they don’t trust themselves.

Leaders trust teams because there are more than one leader in the team — nobody is aware of that fact, though. People will do the right thing if you trust them and let them make decisions, while holding them accountable.

The biggest lesson I ever learned as a leader was to create more leaders. Having more leaders in a team helps you save time. When you need a day off to deal with a massive romantic breakup, the other leaders step in.

You step back into the office the following day and it’s as though you were never gone. The work just kept getting done. And the people who appreciate your leadership approach come over and drop four magic words: “How are you doing?”

Trust a person to do the work and they’ll do the work for you.

Imperfection Is Okay

You can suck at a lot of things and still live an enjoyable life.

Your imperfections allow your true talents to shine through. You can divert your focus towards what you’re good at and enjoy doing, rather than fretting over trying to be good at everything.

Nobody’s perfect, and you already knew that. So why doesn’t this cliche advice apply to you?

Think of imperfection like rust: it gives everyday items character.

A little rough-around-the-edges is beautiful when you zoom out.

Seek Feedback from Your Team

It’s amazing how dumb you can act. Feedback helps you see when you’re acting dumb, so you can be clever again.

Bosses conduct 1–1 meetings like it’s a homicide investigation. You’re supposed to plead your case for performance. It’s a one-way street no nowhere.

But a 1–1 meeting is a two-way evaluation. If my performance sucks, and you’re my boss, then you probably had something to do with it. We’re both guilty. Because we’re both in this ‘boss relationship’ together.

Feedback shows you who you are — and who you have the potential to become.

Coffee Lubricates a Relationship

The leaders who stick around and don’t keep changing like my underwear all have one thing in common. It’s not so obvious. It’s not a giant life-hack.

Leaders lubricate relationships with coffee.

Leaders who have regularly taken me out for coffee over the years have had a huge advantage. Leaders see the world differently over coffee with you. More coffees with leaders could change the world in a tiny way. A cafe is a beautiful place to discuss humans, and business.

Cafes are a reflection of humanity. Cafes show people congregating which subtly reminds us that we’re all in this together.

If You Are the Boss of Somebody, You Are the Boss of Nobody

You can’t dictate people’s lives. This feeling lasts for a very short time.

When you try and rule over a team they eventually, quietly, tell the truth behind closed doors. The truth about your boss life gets louder and louder. Eventually, real leaders can’t drown out the noise of a boss. This causes leaders to hit the big red fire button, and often, not even know what the hell went wrong.

Humans need leadership, not bosses.

Leadership means you don’t own or control anything.

“Another day, another boss” is a feeling I’ve felt many times in my life. It’s not fun to change bosses as many times as you change underwear. Sometimes all you want to do is be heard, even if you don’t know a lot like me. Show me importance and I’ll show you a boss.

Show me an imperfect person who doesn’t control anything or hold lots of meetings, and I’ll show you a leader. A leader can be anybody — even you.

Nobody is really the boss of you. They just temporarily think they are.

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Tim Denning

Written by

Aussie Blogger with 100M+ views — Writer for CNBC & Business Insider. Inspiring the world through Personal Development and Entrepreneurship — timdenning.com/wc

The Ascent

The Ascent is a community of storytellers documenting the journey to a happier and healthier way of living. Join thousands of others making the climb on one of the top publications on Medium.

Tim Denning

Written by

Aussie Blogger with 100M+ views — Writer for CNBC & Business Insider. Inspiring the world through Personal Development and Entrepreneurship — timdenning.com/wc

The Ascent

The Ascent is a community of storytellers documenting the journey to a happier and healthier way of living. Join thousands of others making the climb on one of the top publications on Medium.