How to Delegate Tasks to Increase Your Productivity with Sean Coyne
11 Dec 2025 · 15 min
Sean Coyne breaks down a five-level delegation framework, from assessing and reporting all the way to full delegation. He walks through corporate failures and how clear expectations, real authority, and training move people from needing constant checks to owning the work.
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You're listening to Freedom fastlink, presented by capitalism.com this is the show about building businesses and investing profits so that you can live life on your terms. And now, your host, the future owner of the Cleveland Indians, Ryan Daniel Moran.
Sean Coren here. Today's episode is going to be about delegation. This is an area that I myself have struggled to excel in and have been continually working on throughout my career. And this is an area that I've seen both entrepreneurs and solo contributors really have a difficulty in taking on. And part of that is in school and kind of early on in our careers, this concept of delegation doesn't really exist. In fact, everything is being delegated to you. But you don't really understand it in that way. You don't feel like, oh, I am part of delegation. You just think, oh, I am doing my job. So I found a really great framework based on an article by Peter Economy on different levels of delegation, kind of a different way to think about it. And then I also want to talk about some of the common pitfalls. So we'll go through the five levels, talk about some of the pitfalls. But first, a really great quote that I've found by General Patton is don't tell people how to do things. Tell them what to do and let them surprise you with their results. I think that's a really good mindset to have when you are delegating and, and you might not be able to jump there on day one with a brand new teammate, but your goal is to tell your team what winning looks like and let them make it happen. Because the way that they do things is going to be a little bit different than the way that you do things. And if you have trained them and provided them with feedback and communicated clearly, as long as you get the goal that you expect, the way that they get to it in the way that works best for them really shouldn't be something that's keeping you up at night. So just a little bit on some of my background with delegation in my corporate career in healthcare consulting, at one point I had probably 13 or 14 different projects that I was responsible for. And each project had a consultant and a data analyst who was offshore, all of which these moving parts, you know, needed to be delegated. There's obviously no way I could, you know, do the work for 14 projects at once. And during that time was kind of a crash course in delegation. And not necessarily through instant success, actually, it was through a lot of instant failure. And some of the things that I took away from that were One giving people the freedom to fail and being there to support them when they do. One of the projects that I had was really challenging and at one point I had taken some tasks back and until we talked about it, didn't realize how demeaning that was to the individual that I had taken back. Their explanation was in my mind, mind I thought I was being helpful. Like they seemed they had a lot on their plate and things weren't getting done, but in their mind they thought that I didn't trust them to get it done. And that really wasn't good for our working relationship. And kind of once we got through that and got to the point where we had better communication as to when things need to be done, we didn't get into that spot. And we had a level of trust that if they weren't going to get done, that would be escalated back to me so that my seeing the big picture could either delegate it to someone else or, or could step in and take care of things in a pinch. So before we get into some of those common pitfalls, walk through five levels of delegation. This is based on an article by Peter Economy, kind of splitting delegation into different levels, which we don't really think about. We always want to jump straight to level five, which is just hand off a task and go. And that doesn't always work. So the five different levels are assessing and reporting, recommending, developing an action plan, making the decision, and then finally full delegation. So we all want to get to full delegation, but given this framework, you can see that there's a lot of work that needs to be done to get there. So as you bring on new team members, even if they're rock stars, there's going to be some work in you communicating your expectations, the way that you do things, sharing the knowledge that you have to get them from level one to five. And if you're bringing someone with little experience, maybe straight out of college or an intern, you know, you should expect and plan to spend more time in the earlier levels if you want them to do a good job at level five. You know, this isn't a one week project to get from one to five. This is kind of ongoing and it'll vary by the task and by the person. But before you get to this point, you want to make sure that you have clear systems in place and as you move through this, make sure you have clear training in place. So level one is just assessing and reporting. So this is kind of the most basic form of delegation. And at this point you're probably not saving much time. You're probably at best breaking even with your time. But you want your employees to start providing you facts and just assess the situation and then have them provide a few possible solutions. And what you want to do is really explain your thought process to them, review the facts and the problem. If you agree that they have found the information you're looking for, explain to them why. If you disagree, definitely explain to them why. But of the possible solutions, you want to walk through your thought process in picking the right one, and that might be number one is not good because A, you know, it costs too much and B, there's too much risk. And number two is pretty good, but that's really not in our wheelhouse. So let's keep that off the table. And level number three, that looks like a good solution. And here's the reasons that I feel so that way your employee, when they do it again next time, can have that knowledge in their head. They can know the way that you're thinking about things, the way to present things to you so that you can quickly move up to the next level. And that's the level 2, which is recommend where your employee makes those judgment calls and they look at the possible solutions and they say, here is the facts, here is the problem, here are some solutions, and I think we should go with number two, and here's why. And if they're not getting the here's why part, that's a really clear indicator that you need to be doing a better job explaining your thought process. Because if they're just picking one because they think it's right, it's really not going to be helpful. And they're definitely not going to be able to move up the delegation kind of framework. So again, at level two, you are making the decision to implement, but you're taking their recommendation and giving them guidance on how to make better recommendations to you until they're at the point where the recommendations they're making you continually agree with. And when you continually agree with, then it's time to kind of move in level three, which is now you feel confident that they're choosing their own recommendation, which is really important than you choosing the recommendation. And then they provide you with an action plan. So at this point, you're not really making a decision on the recommendation. You're only making decisions based on the way to roll it out. If you find yourself saying no, that's not even the right direction. You're not in level three, you're still in level two, and you need to be Doing more explanation of why you feel it's not the right recommendation. So in level three, you still want to share your thought process as to how things are being rolled out, why some experience you've had in the past, some training that you've had, etc. And level four and level five are more of what we think about when we think of the word delegation. So level four is delegating the decision making. So now the employee gathers all the facts, they gather possible solutions, they pick the best solution, they pick a plan and they implement it. So at this point, they are implementing it before they come to speak with you. So they are not coming to you and asking, they're coming to you and telling. So if you're at a point where your employees are coming to ask your permission to do something or you are continually changing their direction, then you're not yet at level four. You're only at level four when they come to you and say, this is what we are doing. And it's really important that at this point, if what they are doing is not at all your expectations to revisit level one, two or three, because somewhere along the lines there's a failure in communication. So at level four, you want to be really careful that you're not micromanaging because they've already made the decision. If you start changing the decision, then in their mind they're going to say, well, whatever I do is never good enough and they're just going to become disengaged and it's just not healthy for your team. They're not going to be helping you out at all because you're actually doing more work. So at this point, you want to monitor and provide feedback, and feedback is very different than overruling their decision. So let's say they are, I don't know, building a race car, and in their decision, they determine they only want three wheels and every other race car on the market has four wheels. So instead of saying, no, no, everybody else is doing four wheels, we need to do four wheels. Your feedback would be, I see you've picked three wheels, that's a little different. Everyone else has four. Can you explain to me your thought process there and why you think that might be the right decision and have that discussion? Now, if they say, we're going to do a race car with no wheels and the race car is obviously not going to go well, one, you're not in level four yet because they aren't making the correct decisions. But two, make sure you understand you're not in Level four, you're not yet ready to delegate the full decision. And at this point, be ready to reward them because they're taking on, at this point, a lot of the work that you don't have to do any longer. Those rewards don't have to be huge, but you need to continue to provide positive motivation that could be great job. Like, you realize you did that entire project without me at all. Like, this is great. This is going to help our business grow. And continue to explain your thought process through your feedback and your monitoring. Level 5 is where we all want to get, which is where you can say, we need to build a race car to win the race. Here's the person you can talk to about the rules. And it has to be ready by next Friday, which is really important than saying, we need a race car. So you want to make sure that you're providing the parameters, but allowing the freedom for your team to build that race car in the way that best aligns with their abilities and the way that they see most fit. So at this point, you shouldn't be actively monitoring the project. You want to make sure your employees know that they should report exceptions and unique problems to you, but otherwise, it's their task. And that task may be, we need a race car, and we need to win the race. The race is June 14th. We probably need the car ready by June 1st. Let's win the race. And if there's no exceptions, you should have a race car ready on the first that is competitive to win the race. And if you do win the race, make sure you're ready to reward great results with great rewards. And that could be promotion, because at this point, you have delegated an entire aspect of your business. And if throughout this, you find the decisions are being made in a way that totally go against your company or your mindset, think back onto what level you were actually on. And if you're on four, that means monitoring. If you're on three, that means more constant feedback, et cetera. So I found those levels really helpful to think about how to delegate to different individuals and also different tasks. It's important to note that if you have someone taking on a new role, they might be at a different level of delegation for that role if they don't understand the way that you expect things to be done with that aspect of the business. So I want to talk about some common pitfalls that I myself have worked through and I've seen many others work through. And the first, I think, is one of the most important. I mean, they're all important, but having really clear expectations. So instead of saying, let's build a race car, saying, we need a race car that will win the race on the 14th, we have a $20,000 budget. We can allocate 14 hours a week to it, making sure that you're really defining the scope that the individual has control over. So if you have a big project, there should be a budget. If you have a big project, there should be allocation of resources. If you have a big project, there should be milestones or a deadline. So the smart goals are always a good way to think about things. But if you find yourself getting back projects that are not at all what you're expecting, then you really need to take a look and say, am I communicating clearly? Because this is a really difficult part of delegation, especially coming on as a, like a sole contributor. You've never had to explain things to anyone but yourself, so you always did it the way that you expected. So this can take a little bit of kind of work on your end and continual practice. The second one is handing over authority. So going back to the racecar project, if you have a budget of $20,000 and you need to hand over the authority to spend that in a way that gets the project done. And if you don't have trust in your team to spend that $20,000 on a race car, you need to seriously think about what level you're at, because you're not at level five if you don't trust them to spend the $20,000 wisely. So you want to hand over that authority, and you want to make sure that while you are there to support them, you have coached them and provided them with the training and the systems to do their best work. Which means if you take back the authority, that's a huge leap back in your delegation. So handing over the authority means handing over the win and handing over the loss. And a way to kind of make that less terrifying is before you get to level five, continual coaching. And even at level five, but coaching your team so that by the time they are ready to delegate a full task, you have faith in the way that they make decisions, the way that they spend money, that they'll get the goal done on time. And if they're not, then you're still in level one through four. And all of those require coaching, which is an investment in your team, in your people, and in yourself. There's a really great quote. I don't know. I think a CFO and a CEO were talking. The CEO said, we need to implement a training program. We're going to spend $100,000 on these two individuals for training this year. And the CFO said, that's a lot of money. Like, what if we spend all that training and they leave? And the CEO's response is, what if we don't and they stay? So you need to continually invest in your team so that you can hand over authority. And finally, is the monitoring of their project. You know, in levels one through four, you want to make sure that you're keeping an eye on things, but that's really different than checking their work. Monitoring progress is being involved and supportive and not coming in and saying, don't do this, do this. It's coming in and saying, oh, I see we're doing this. And it looks like we might not be able to hit our milestones. Like, let's have a discussion on what else is on your plate. Giving them the tools that they need to make the right decisions instead of making the decision for them. So I hope that this has been helpful and kind of a different way to think about delegation. Some tips and, and tricks on hurdles that I have come into encounter. But I really want to stress that, just like the Eisenhower matrix, this takes practice. If you have been delegating for one year, just think about the Fortune 500 CEOs that have been delegating for 30 years, and they are continuing to practice. As they get new members of the executive team, they also have to work with them to find out the best way to delegate between their two personalities. So it's certainly something that requires practice, requires an investment of your time and in your team, and that you shouldn't expect to happen overnight. So we walked through a little bit of intro to delegation. We went through the five different levels, and we discussed some of the common pitfalls. I hope this has been helpful in shedding a new light on delegation and the way that you think about it and that you can take these thoughts and these ideas back to your team to do bigger and better things through excellent delegation. So thanks for listening and I'll talk to you next time.


