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Rob Cahill


Co-Founder and CEO

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Lessons in management: we asked some senior leaders what their first-time mistakes were


No one goes into a leadership position fully prepared for the role - there are always learning curves and things you pick up along the way. Here, we talk to senior leaders about their formative experiences and what they wished they'd known when starting out. 

When it comes to pivotal points in your career, being a new manager has to be one of the most challenging.

You’re used to being a star performer – that’s why you were promoted – but to succeed as a manager, you need to master an entirely new set of skills.

To help new leaders ease the transition, I sat down with some of the industry’s top management minds and asked them what one thing they wish they’d understood in those critical early days.

1. Power can turn people (even nice ones) into selfish jerks

According to Bob Sutton, best-selling author of Good Boss, Bad Boss and Professor of Management Science and Engineering at the Stanford School of Engineering, a little humility goes a long way. He says, “as a new manager, the first thing you need to learn is that people are watching you a lot more closely than when you were individual contributor.

You will get more credit (and more blame) than you deserve for the performance of those you lead.

“The second thing is that you will get more credit (and more blame) than you deserve for the performance of those you lead. The third thing to remember is that having power over other human beings is one of the most reliable ways to turn people into selfish jerks.”

Sutton’s advice for those of us who like to think we’ve got it handled? “You may think it won’t happen to you, but it will.”

2. Being right doesn’t win arguments

Paul Suh, long-time finance executive and CFO at Sandow, also referenced the dangers of new-manager hubris.

“Ever have an argument with a friend or colleague where you are convinced you are absolutely right, and at the same time he is also convinced he is right? The one thing I wish I had known about my first time at being a manager is the importance of equally developing both emotional intelligence and self-awareness.”

Suh points out that “every minute you spend on that argument is a minute not spent on solving the actual problem.” He advises new managers to learn about the personalities around them. As for that team member who just has to be right? Don’t argue. Acknowledge his point of view, then move on to solve the problem.

3. Sometimes you’re the worst person for the job

Whitney Johnson, acclaimed author of Disrupt Yourself, has repeatedly been ranked among the world’s most influential management thinkers. She admits that one of her biggest early frustrations was trying to fit everyone into the same box.

“As a new manager, my tendency was to want to clone myself. To find people just like me. I wish I'd understood that that was the wrong person to hire. Duplicative. Frustrating for all.”

As a new manager, my tendency was to want to clone myself. To find people just like me.

A good manager recognizes her own strengths and weaknesses, as well as those of others, and knows how to leverage those attributes to accomplish the end goal. “I now look for people who do things well that I don't. People I trust enough to say to them, I don't know how to do what you do. Then let them do it.”

4. You’re a coach, not a player

Elizabeth Robillard, Vice President of Partnerships and Operations at Lytics, has been advising startups and building and scaling teams for years. She says one of her biggest challenges was learning to pass the mantle on the day-to-day tasks.

“In my first year, I think I would have spent more time managing and less time doing the work myself. I think we are often promoted to our first manager role in a player/coach role, so we are still expected to do the work, but also manage and mentor the team. This puts first-time managers in the hard spot of having two different jobs.”

Most of us gravitate toward the familiar, but as a manager, your role has changed. “You can lead by example, but you also have to provide direct instruction and feedback. If I could go back, I would be more intentional about the management side and push myself further down that path.”

5. Change is even harder than you think.

Jascha Kaykas-Wolff, author of Growing Up Fast and CMO at Mozilla, has always been one to embrace change. As someone who loves experimenting with new ideas and processes, he admits that he didn’t really “hear” his earliest direct reports when they tried to impress on him the challenges of dealing with change.

Change, any change, is hard, but it's less so if you have the context and reasoning behind it.

“Change, any change, is hard, but it's less so if you have the context and reasoning behind it. I wish I had understood that having transparency in process and decision-making is the only way to be as a manager overall— and that’s doubly important if you are dealing with change.”  

6. You won’t wake up one morning and know how to lead

From my own perspective, one of my earliest and biggest mistakes was thinking that learning to be a manager is like learning to ride a bike.

You can’t just go to a management training seminar for two days, implement a couple of tricks and proclaim yourself a great manager. It seems so obvious now, but back then, I didn’t fully recognise or appreciate the ongoing effort that goes into being a good manager. It requires practice, feedback and coaching from others. It requires being willing to ask for help and admit when you don’t have the answer.

Most of all, it requires you to be humble and willing to try new things, making (and making up for) countless mistakes, accepting failure and challenges along the way.

Interested in this topic? Read What common mistakes do new managers make?

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Rob Cahill

Co-Founder and CEO

Read more from Rob Cahill

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