Insights, advice and know-how.

Courier Workshop episode 8: Delegation

Courier Workshop episode 8: Delegation

Courier Workshop Weekly

Everyone knows how important delegating tasks is to growing a business, but plenty of founders find it hard to get out of the weeds – whether that’s because they don’t know how to or just don’t want to. We speak to a couple of founders on how they’ve improved their process and get taken through a step-by-step guide to effective delegation from someone who’s taught Amazon and the US Army. 

AMIRAH JIWA: From Courier, I'm Amirah Jiwa.

DUNCAN GRIFFITHS NAKANISHI: And I'm Duncan Griffith Nakanishi. 

AMIRAH: Welcome to Courier's Workshop podcast. Every two weeks, Workshop breaks down one essential business topic and explains how it could be useful for you. Our goal is to get you just the right amount of info to help you apply what we're talking about to what you're working on. I'll be speaking to experts with practical tips and founders with relevant experience. 

DUNCAN: And I'll be explaining essential terms and summarising the key takeaways at the end of the show.

AMIRAH: Today, we're covering a classic leadership topic that a lot of founders struggle with: delegation. We all know it's good in theory, but it can be hard to do effectively in practice. Like all the topics we cover on the show, getting it right is important to your business' success.

GUEST #1: Sometimes these things take time, but trust that people can probably do the job better than you – you've hired them, right?

GUEST #2: If you want to go fast, go alone; if you want to go far, go together. And I was like there's definitely a limit to how much I can do on my own.

AMIRAH: First up, we spoke to a serious expert on the subject. Deborah Grayson Riegel is a keynote speaker and consultant specialising in leadership and management communication. Her clients include Amazon and the US Army and she teaches at Wharton, Columbia Business School and even Peking University. Deborah, what are some of the key benefits of delegating? Why should leaders focus on getting this right?

DEBORAH GRAYSON RIEGEL: When you think about what delegation does, if you're the leader, it increases your efficiency. It also increases the team's impact. It gives you and your team a much bigger range of skills and impact and competency. It gives you and your team emergency backup. The last thing you want to be is indispensable. As much as we think we all want to be indispensable, if you're indispensable, you can't ever get promoted, because they need you to do the thing that you're doing. It allows the team to get more connected with each other. When done well, it improves communication. It helps the team be collaborative and strategic. It also balances workloads, it empowers people, and it helps you retain talent, especially when you are demonstrating trust in others. 

AMIRAH: And with all these clear benefits that you've outlined, why do leaders still often struggle to delegate?

DEBORAH: When it comes to delegating, there's a lot of self talk that needs to happen in order for somebody to move forward with it. Here's what some of the leaders that I coach say to themselves: 'I don't have enough time to delegate', 'I need to be in charge of this for a variety of reasons', a very common one, 'nobody will do it like I will do it'. 'What if it gets done well, and I don't get the credit for it?' Or, 'but I like doing this and if I give it to somebody else, maybe I won't get to do the work I like'. They also think to themselves: 'What if I'm not needed anymore?' 

Often, it interferes with their sense of meaning and status and importance. There's a whole bunch of stories that people are making up about delegation, which are interpretations based on a lack of enough concrete information. I think those are the first conversations we need to recognise. At the moment, those are invisible, and we need to make them visible. 

AMIRAH: And how can we overcome some of those negative emotions? 

DEBORAH: I like to bring in a strategy from a woman named Dr Susan David, who's the author of a book, Emotional Agility: Get Unstuck, Embrace Change and Thrive in Work and Life. She suggests that every time we have a negative emotion, we should ask ourselves: what the funk? The question is: what is the function of this emotion? So, if I am feeling concerned, reluctant, resistant, let me assume that that feeling is pointing me towards something that feels important. If I'm feeling reluctant to give it to somebody, maybe it reminds me that my status feels really important to me, or that I really care about the quality of my work, or that my client relationships feel of the utmost importance to me.  I invite people who are really facing a barrier – a psychological barrier to delegating – to examine what they're actually more committed to: status, popularity, a perception of being important, then to delegating, and then to run some short-term experiments to see if you can still feel important or popular while you're delegating as well.

AMIRAH: So a leader has confronted the psychological barriers and is ready to delegate. How can they do it?  

DEBORAH: 1) Decide exactly what you're going to delegate and why. 

2) Pick the right person and explain to them why you're delegating to them. Use it as an opportunity to give them some positive feedback, or let them know that you're looking to grow their skills in their career, that delegating to them isn't a punishment. 

3) Clarify the responsibility that you're giving them – what parts of this can they do, what parts of this are they not going to do? Clarify the level of responsibility they have. 

4) Be very clear about what success looks like – what are we looking to accomplish? Then you have a shared picture of results or success. 

5) Agree on that person's level of authority. Make some agreements about checkpoints, milestones and feedback. Create a motivating environment, whether it's granting access to resources, teaching or training on a new skill, cheerleading or quick wins. Figure out what this person needs and try to reduce barriers to their motivation. 

6) Finally, just get out of the way until you're needed, right? Don't hover, don't keep checking in. One of the goals of effective delegation is to increase trust. Hovering, as my children will tell you, decreases trust – it does not increase anything.  

AMIRAH: So there you have it, a step-by-step guide to delegating from the expert. We know that actually implementing this kind of thing can be tricky. So we also spoke to a couple of small business founders about their relationship to delegation, and what they've learned about how to do it right. Here's Elsie Rutterford, co-founder of BYBI. BYBI is a natural sustainable skincare brand based in London. When BYBI started three years ago, it was just Elsie and her co-founder running it all for a while. But that team has since grown to 10, and they've actually just brought on their first major senior hire, a managing director. Elsie, what has your experience with delegation been?

ELSIE RUTTERFORD: It has been really tough – neither of us are totally comfortable with it even now. We've always been in the weeds of the business and that shouldn't be the founder’s role, and we're very, very aware of that, hence starting to hire in people like a managing director.

AMIRAH: And why do you think that is?

ELSIE: Our struggle has been that in order to effectively delegate as a founder, you have to have full trust in the team that you've built. We have, perhaps, not spent enough time or bought into enough resources when it comes to recruitment and the recruitment process. When it comes to really, really testing people to see that they've got the necessary skills. But it's not easy, because it's your baby. It feels like a child, and handing your child over to someone.

If you have done bits of the role before, because we've been in the weeds of things, I was doing our social media and Dom was running our warehouse – we've done most of what our team is doing before. So there's always a sense that I could do it faster and better myself, kind of thing. 

AMIRAH: How have you started to get over some of those fears that you outlined?

ELSIE: Upon reflection, we've really identified how we can improve. The hires that we're making now and the training that we're giving the team now is all set up to be able to allow us to have a structure where we can comfortably delegate. It's about getting over that hurdle, and trusting that you've hired the right people to do it. That they've got the right kind of support around them to be able to do the job not only as good as you could, but better.

AMIRAH: Do you have any tips that you can offer to other leaders or founders looking to delegate more effectively?

ELSIE: We've now learned that the process of delegating is really important. So we'll say: this is the task that we want to hand over, this is the business that we want to hand over, but throughout that time, we'd like to see, X, Y, Z updates, we'd like to see the finished project here. The delegation is one part of the actual execution. What the delegator needs to understand is their expectations on the touchpoints throughout that task: when do you expect to see updates, or the final, finished project? Maybe it doesn't even need any sign off at the end of it, but then it's about how much contact you want in that process. 

One thing that we found when delegating some of the slightly high-level stuff, we still want some visibility on it. We're handing it over and we're not executing it, but the team is still small, and we're still very much involved day to day. For our own peace of mind, we would still like a CC on that email, just to know that it's happening and it's moving forward and then we'd probably like to sign it off in two weeks’ time when the project looks like X or whatever. You have to drive managing those expectations with the people that are taking on the task.

AMIRAH: Now, here's Calvin Benton, the founder of Spill, a Slack app that lets employees easily book in sessions with a qualified therapist. Calvin has a background as a solo maker, but he's now managing a small team of employees. Calvin, what has your experience with delegation been?

CALVIN BENTON: I started out building products that I really thought should exist. I did this on my own – I was technical, so I could cover a lot of stuff myself. What that meant was that I became quite used to working on my own, shipping everything that needed to be shipped, from brand and marketing to product development all the way through to actually coding the thing. I think I have definitely kept some of those probably bad tendencies from my maker days when I was building stuff on my own. I found it super tricky to delegate, especially when you can physically do everything.

AMIRAH: And what do you think is at the root of your issue with delegation?

CALVIN: As a founder of a company, you are trapped a little bit because you can do everything and you probably think you can do it better than most people. You know all of the context for situations. There's often a cost to delegating, right? There's a cost of having to explain the situation, explain explicitly what you want to happen. In your brain, you probably do a cost-benefit analysis of whether it's going to be worth me explaining this, or whether you'd prefer to have a few passes to get it exactly how you want it to be. The cost of doing it versus the benefit, it's a tricky trade off. I've definitely seen as Spill has grown and I've been forced to do work that other people can't do, then the cost-benefit trade-off has slightly tipped a little bit. Me doing this is time that I could have spent doing work that other people can't do.

AMIRAH: Any tips you've got for delegating effectively?

CALVIN: What I've learned over time is that it's super important to do it earlier rather than later. I say that because, as a project progresses, the opportunity cost I was talking about, the cost of delegating to someone and filling in all that context, gets bigger. If you include people earlier in the process, then it's much easier to then delegate that task later on.

AMIRAH: That's great. Any final thoughts on this subject?

CALVIN: I don't know. I think it's a real challenge because a lot of the skills that get you by when you're like creating an early-stage business, a lot of those core building skills, when you get to 10 people, you've kind of got to give them all up. Suddenly, what made you successful going from one to 10 people won't help you when you are going from 10 to 20.

AMIRAH: Thanks so much to Deborah, Elsie and Calvin for that valuable advice. The Courier guide to delegating is available online at If you're looking for more tips for now, here's Duncan to summarise key takeaways from today's show.

DUNCAN: 1) You might have some emotional barriers that prevent you from delegating properly. If you're struggling, start by asking yourself why that might be.

2) Remember that there's lots of value to delegating effectively. Ultimately, it means your business can make a bigger impact and increases collaboration and trust among your team. 

3) You have to set up a thoughtful and structured process. Make clear what your expectations for the work you're delegating are, and when you want to check in and provide feedback. 

That's it for today. If you have any ideas or feedback for us get in touch at workshop@

AMIRAH: Workshop is back in two weeks. But if you're looking for more useful insights before then, check out Courier's new podcast Looking Up, which talks to small business owners from across the UK about how they're surviving and thriving during the pandemic. You can find Looking Up on your favourite podcast platform now. See you next time.

You might like these, too