Delegation dos and don’ts
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The Insightful Leader Logo The Insightful Leader Sent to subscribers on January 22, 2025
Delegation dos and don’ts

At the risk of being the millionth person to tell you this: you should delegate. It can simultaneously save you time and develop your ranks.

Of course, I’d need about ten hands to count the amount of times I’ve tried and failed to do that myself, so I’ve long thought the advice grossly oversimplified. Brenda Ellington-Booth, a clinical professor of management and organizations at Kellogg, agreed.

Drawing on her years of experience as an executive coach, she offered a primer on delegation in a recent episode of The Insightful Leader podcast. Today, I’m bringing you some highlights from that conversation (edited for length and clarity). Plus, how early exposure to entrepreneurship can affect girls, in particular.

On “reading the room” before doling out work

“It’s really about you communicating, giving people an opportunity to show what they can do and knowing when to say, ‘okay, this person has got it, I can give them more.’

And then it’s like, ‘ooh, this person needs a little bit more hands on.’ There’s no one-size-fits-all for delegating each employee that you have. And that’s what makes this work—leadership, management, delegating—really hard … so the strategy is more about reading the room, understanding the strengths and weaknesses of your team, making sure you are clear about your own expectations, and then communicating that clearly to others.”

On delegating tasks that are relationship-based

“Maybe you delegate your direct report going to a meeting and representing you. That’s scary.

Prepare them for what-if scenarios that might likely happen, or prepare them for the question they’re just not going to be able to answer or they feel uncomfortable [answering]. It’s more about, ‘well, if there’s a question that comes at you, let’s practice how you say ‘I don’t know’ and still look credible.’

Do job shadowing. But it’s more than [having them] show up to the meeting. It’s the meeting before the meeting. ‘So this is what I’m going to do in the meeting. This is my thought process. This is what I’m unsure of. Let’s see how it goes.’ The meeting happens and then there’s the meeting after the meeting. ‘It didn’t go as I thought,’ or ‘this question threw me and you see how I handled that?’ And really getting the employees to start thinking proactively how to prepare, what to do in the moment, and then hopefully how to think about what happened afterwards.”

On letting go

“Particularly when someone has worked long and hard on something and it literally feels like a baby to them, it’s hard to let go and let someone else kind of make it their own, recognizing that child is not going to look like it did when you handed it off. It is grief. It is loss. It’s really about making sure [the person struggling to delegate] understands, reminding them of what their job really is at that point in time. And I [as a coach] can say ‘well, you can not delegate that. But what are the consequences of you not delegating?’ and getting people to think that through on their own. Usually people arrive at the right conclusion.”

Hear more from our three-part conversation with Ellington-Booth at Kellogg Insight.

For girls, early exposure to entrepreneurship can be a game-changer

Worldwide, women are less likely than men to strike out on their own as entrepreneurs: across thirty-eight highly developed countries, women were only two-thirds as likely as men to launch their own companies, according to a 2021 OECD report.

Drawn to the statistic, Maddalena Ronchi, an assistant professor of finance at Kellogg, wanted to know if there was something that might help motivate more women to pursue the field.

A new paper from Ronchi and coauthors found that exposure to their peers’ entrepreneur parents as a teenager seemed to alter girls’ educational and career trajectories: such girls were more likely to continue their education after compulsory school and had a lower risk of holding low-wage jobs throughout their working years. What’s more, the researchers found that girls who had early exposure to entrepreneurs and then pursued their own entrepreneurial ambitions went on to create more successful and more women-friendly companies than the average entrepreneur.

“These results challenge the view that the most successful female entrepreneurs would enter the profession regardless of early exposure,” Ronchi says.

Read more in Kellogg Insight.

“Everyone makes mistakes. Great leaders have the courage to admit when they are wrong. It shows they are human. It shows they are humble.”

Sanjay Khosla, on LinkedIn, on the upsides of leaders owning up to their failures.

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