I Suck at Delegating. My 2 Ways to Get Better at it.

What's up, everyone? Welcome back to another episode of The Crazy Ones. This is one of your hosts, Alex, and I am back with a Founder's Journal style episode. What is a Founder's Journal style episode, you may be wondering? Well, before The Crazy Ones, I used to have this show called Founder's Journal where I would basically do these 5 to 25 minute journal style episodes where I'd monologue about some topic related to building businesses. We've started mixing that format back in with our other episodes of The Crazy Ones, which are the ones where Jesse and I basically turn on the mic, turn on the camera, and talk about what's happening in our lives as entrepreneurs. And you basically get to be a fly on the wall. We've gotten a ton of good feedback about these journal-style episodes, which is why we've brought them back and we're going to continue to do more of them. So if you have a topic that you want Jesse or myself to talk about, shoot us an email at thecrazyones@morningbrew.com. If you're wondering what topic would I want you to talk about, think about what is the biggest pain point within your business right now or your career, or think about what is the number one priority that's taking up mental real estate in your brain. When you go to sleep, you're thinking about it. When you wake up, you're thinking about it. And just email us with that priority or challenge. And we're going to try our best to turn that into an episode. This episode is all about how I came to the realization that I suck at delegation, which is a really bad thing because as an entrepreneur you want to be good at delegation. So I talk about coming to that realization, why I think I'm bad at delegation, and 2 very tangible tools that I'm using to get better at it. So let's hop into the episode. What's up, everyone? I'm Alex Lieberman. Yo, this is Jesse Pujji. And this is The Crazy Ones. I always thought I was good at delegation. I assumed that I had to be given Morning Brew's growth over the last 8 years. But as I've re-immersed myself in new businesses outside of the Brew, I have realized that this assumption was completely wrong. And here's how I came to the realization that I'm actually really bad at delegating. I've been traveling nonstop for the last 1.5 months, and as I've been on the road, I started to notice that the speed of progress within The Plunge, which is my backyard plunger throwing game, our progress slowed meaningfully. And that slowdown had nothing to do with my partner not working hard enough or fast enough. And it had everything to do with my lack of ability to delegate effectively. So here's what happened. I was traveling. I went to Austin, to Chicago, to L.A. for a combination of weddings, work stuff, bachelor parties. And I had less time to work on the day-to-day of The Plunge. At the same time, I found out my business partner had plenty of capacity to work on things, and that capacity was going unused because I hadn't communicated that I needed help on tasks that I had claimed responsibility for. And so that begs the question, why did that happen and why am I bad at delegating? And I meditated on this, and I think it comes down to 3 things for me, 3 reasons that I currently suck at delegating, but 3 things that I want to improve on so I'm not bad at it in the future. First reason I am bad at estimating how much I can get done in a day. I assume I'm more productive than I am, and I assume that things or tasks take less time than they actually do. And the most pronounced example of, let's call it this miscalculation, is in the world of Morning Brew, where if you were to look at our original pitch deck that we shared with investors in 2015, we had shared in that deck a slide that was all about our one-year strategy. And while that strategy in that one slide was actually spot on with how the business has grown over time, we still have yet to complete what was on that specific slide for a one-year strategy 8 years later. And so to get better at estimating my work, I think I should act under a very simple assumption until I prove that assumption wrong. One thing, that's it. One thing. I can only get one very important thing done in a day. That's the assumption I have to have, which means that I need to be ruthless about picking What is the one thing that I want to do in my day? And I need to assume that everything else needs to be delegated if I want it to get done. So that's the first reason that I think I'm bad at delegating is I overestimate how much I can get done in a day. I think this is pretty common for people. The second, I think, is less common, but I actually think it's just as important for why I've been bad at delegating. I fear being judged for delegating. Said differently, I worry that if If I delegate, I will come off as shirking responsibility to the person I'm delegating to. I don't want to come off as a dictator who just sits back and has other people do their work for them. And I think there's an easy solve for this fear that I have, and that is communication. I should just communicate to my business partner what I have the capacity to do and what I plan to delegate. And I need to make sure that he feels comfortable to communicate openly with me any time he feels like I am not pulling my weight. And if he doesn't communicate that, I should assume that I am delegating appropriately. The third reason that I think that I have some serious shortcomings when it comes to delegation is I am addicted to the feeling of being busy. Now, this is a super common thing for Type A personalities, and I think one way of getting out of this loop, the busyness loop, is realizing that there is a massive tradeoff for being busy. Time you spend being busy running in place rather than running forward is time that you could have been spending doing anything else that's actually important in your life. And rather than trying to eliminate busyness altogether, because I generally think when you try to go cold turkey, it isn't necessarily sustainable, I would argue the more moderated or sustainable thing to do is to focus your busyness on 1 to 2 tasks that you love being busy with. So, for example, I love being busy creating content and I love being busy working on organically growing businesses. But also, I have to realize at some point those activities also need to be delegated out. So that's the realization around my inability to delegate and why I'm poor at it. Next step for myself and for you, if you resonate with this challenge to be a good delegator, is to answer the question, now that I know why I am delegating poorly, how do I start delegating well? And I spent a lot of time researching for this episode about different delegation tools and frameworks, and I want to share the 2 that I believe can be most helpful for for you. And these 2 tools complement each other. So make sure you listen to both of them. The first tool is the Eisenhower Matrix, and you may be familiar with the Eisenhower Matrix, but I think it's worth revisiting periodically. Long story short, Dwight Eisenhower, he got a shit ton done during his career and his life, from running the country to helping create the highway system to being president of Columbia University and a bunch more stuff. And he attributes his productivity to a simple 2x2 grid that goes as follows. First, I want you to picture in your mind an x-axis that's going from left to right. And on the x-axis, you have non-urgent tasks that are on the left side and you have urgent tasks that are on the right side. So that's the x-axis, not urgent on the left, urgent on the right. Now, in your head, draw a y-axis through the middle of the x-axis going up and down. And at the top you have important tasks and at the bottom of the y-axis you have not important tasks. And so what this does is it leaves you with 4 boxes. Looks like a tic-tac-toe board. Actually, that's a lie. It doesn't look like a tic-tac-toe board. It's a 2 by 2. But so you have these 4 boxes. And let's start with the top right box. The top right is important and urgent tasks. Very few things should live in the important and urgent task box because at the end of the day, there are only a few things that actually really matter that need to get done right now. But for the things that do live in that box, those are the things that you should be personally doing. You shouldn't delegate them out. You shouldn't delay them. You should do them now. Now, top left is a task that is important but not urgent. And these are tasks you should either delay or delegate based on how much trust you have in the people that you are delegating to. Given it's important tasks, you'd want to just delegate this out to anyone. Also, if there are people you trust, you don't have to just put that work on yourself. The next box is bottom right, and that is not important but urgent tasks. I would argue The vast majority of things you work on in a given day are not important, but they are urgent. They need to get done. And so these are tasks you delegate because you need to get them done, but they are not a needle mover to your business, so they don't require your personal attention. And finally, the bottom left is unimportant and not urgent. You should get really, really good at moving many of your tasks to this bucket. And if a task reaches this bottom left bucket, It gets deleted, no questions asked. I would say the biggest issue that I have that many entrepreneurs have is they are really bad at deleting tasks. They, even if they're good at delegating, sometimes they'll delegate tasks that actually shouldn't be delegated because the fastest way to do a task is to not do it at all. So since revisiting the Eisenhower Matrix that I just described, I've basically turned this into my daily to-do list. So I will write down everything that I think needs to get done for my day in a list. And then what I'll do is I will draw out the Eisenhower Matrix. So the x-axis and the y-axis forming those 4 boxes, and it will place all of my tasks into one of the 4 squares of the matrix. Now I want to finish with the second tool, which is 6 Levels of Delegation. So if the Eisenhower Matrix told you what to delegate, Ari Meisel's 6 Levels of Delegation tells you how to actually delegate the things that you should be delegating. And so the 6 Levels of Delegation go from least delegation and lowest trust in the person you're delegating to, to greatest delegation delegation and highest trust in the person you're delegating to. And so I'm going to walk you quickly through all 6 levels. Level 1 is what I call order taking. I tell you to Google search, let's say, best no-code tools and to share the top 3 links with me. And you go ahead and do that. This level, level 1, requires no nuance, no subjectivity, no critical thinking. It is just order taking. It requires you to do as you're told. Level 2 takes it one step further, and it is what I call investigating. So using the same example, I tell you that I'm looking to pick a no-code tool to build a new business idea I have, and I would like for you to research my options and present the information. And so this level requires you not to just take an order, but to actually consume the content, synthesize it, and clearly communicate everything I need to know to make a choice about what no-code tool to use. Level 3 is advising. So at this level, you trust someone enough to solicit their opinion. So it's no longer just objectivity of giving you information. Now you're actually involving the person in the decision-making process and you get to level 3 when you think you trust someone enough for them to save you time and to help you make an informed decision. So here you're no longer just sharing a summary of the different no-code tools that you found and their pros and cons based on research, but you're also giving me an opinion on what tool you think will best serve my needs. This level obviously requires increased trust because you're now relying on someone else's critical thinking in order to support your own decision-making. Next is level 4, and level 4 is what I call supervised autonomy. Now I am no longer just delegating research and delegating a recommendation. I am actually delegating the entire decision-making process other than final sign-off. So now you're coming to me with the no-code tool that you think best suits my needs, and you're saying to me, hey, I'm going to go with this tool that I researched. Here's why. And if you're cool with it, I just need the business credit card number to sign up for it. And I'm just giving final sign-off. Level 5 takes it a step further. This is what I call rule-based autonomy. So for example, if you're making a decision that doesn't involve more than, let's say, a $1,000 investment, I actually don't want to know about it as the delegator. So by this level, you have delegated everything other than high-risk decisions that you want sign-off on. So if the no-code tool is less than $1,000, You're not even telling me about it. You're just evaluating it, researching it, making a decision and implementing it. If it's more than $1,000, then it goes back to supervised autonomy where I give final sign-off. And it's a way to basically give people you trust autonomy without exposing yourself to outsized business risk. And then we're at the final level, which is level 6, and that's full autonomy. And so the way full autonomy works, it's pretty self-explanatory, but I go to someone I fully trust and I say, we need a no-code tool to build our new idea. And that's all I do now. And as I've delegated everything else, I could go to sleep for a week. And when I wake up, a tool has been researched, a tool has been evaluated, and a tool has been implemented that best suits our needs for the business. And so using Maizel's 6 Levels, you can combine this with the Eisenhower Matrix to not only say to yourself, okay, what's either important but not urgent or unimportant and urgent that I can delegate to someone on my team, but also now that I know what I'm delegating to the person on my team, how much of that task am I willing to delegate based on how much I trust the person and based on how much I trust the person that tells me whether I should be living closer to a level 1, level 2, level 3, or if I implicitly trust them and I trust their critical thinking and I trust their ability to see nuance, then I can delegate more and live more in level 4 through level 6. And so in a perfect world, you're delegating everything at level 6 because that creates leverage and gives you your time back. Of course, most of your time as a leader and a manager is spent moving people from level 1 to level 6 to get to that perfect place, because level 6 requires a significant amount of trust. So that's my experience, not only realizing how bad I am at delegation, but also thinking about why I'm bad at delegation and coming to 3 conclusions about that, and then finding 2 super helpful tools that work together to decide both what to delegate and also how to delegate based on my level of trust in the person that I'm delegating to. And so that is the Founder's Journal style episode of The Crazy Ones. I really appreciate you listening. And as I mentioned at the top of the episode, we want to focus these episodes on topics that builders in our community are prioritizing or huge challenges they're experiencing. So shoot us an email at thecrazyones@morningbrew.com and we're going to just start picking from these topics to inform future episodes of the show. Thanks for listening, everyone. And I'll catch you next episode.