The Confident Entrepreneur With Jennifer Ann Johnson

Delegate or Drown: The Real Cost of Doing It All With Jennifer Ann Johnson

• Jennifer Ann Johnson • Season 4 • Episode 3

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The hard truth: Doing everything yourself doesn’t make you indispensable—it makes you the bottleneck. If you’ve ever muttered, “I’ll just do it myself,” this episode is your turning point.

I dive into the real reasons delegation feels risky—quality concerns, time traps, and control issues—and how ego can sneak in under the mask of “high standards.” But more importantly, we give you a way out: introducing CLEAR, a proven delegation framework that helps you let go without letting things drop.

You’ll learn how to:

  • Define Clarity with concrete outcomes and escalation rules
  • Link the task to your mission so others can use good judgment
  • Equip your team with tools, knowledge, and decision rights
  • Agree on check-ins to create safety without micromanaging
  • Recognize both effort and results to cement growth

I also unpack common delegation traps, like the “boomerang effect” and redoing tasks to match your style, plus how to start small with recurring tasks and build trust over time. The result? Less firefighting, more focus—and a compound effect of impact that scales with your team.

If you’re ready to move from operator to architect and build a team that actually runs with the ball, this is your roadmap.

Thank you to our generous sponsors for making this podcast possible!

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Visit us at jenniferannjohnson.com and learn how Jennifer can help you build the life you dream of with her online academy, blog, one-on-one coaching, and a variety of other resources!

Jennifer Johnson:

We're diving into something that hits close to home for so many of us: the struggle to let go of control and actually delegate effectively. If you're listening to this, chances are you're somebody who takes pride in your work, who cares deeply about quality, and who probably has caught themselves saying, I'll just do it myself because I can do it better. And you've probably done that more times than you would like to admit. I get it because I've been there. In fact, I spent years of my career being what I now call a productivity bottleneck, somebody who's focused on doing everything perfectly, that I was actually holding back my entire team's potential. Today I want to share what I've learned about breaking free from that pattern and how delegation isn't just about getting things off your plate. It's about multiplying your impact exponentially. So let's start with the truth that may sting a little bit for a lot of us. When you insist on doing everything yourself, you're not being a hero. I know that probably sounds really harsh, but you're being a liability, not just to your organization, but to yourself and your own growth. I learned this lesson the hard way about five years ago. I was managing a team of about eight people, and I was personally reviewing every single email that went out. I was approving every small decision and I was staying late to quote unquote fix what was probably fine to begin with, but I didn't think it was. I thought I was being thorough. I thought I was maintaining the quality standards of my business. And what I was actually doing was creating a culture where my team stopped thinking for themselves. The breaking point actually came during a really busy, busy time when I got sick and I had to take three days off. When I came back, I discovered that virtually nothing had moved forward. My team had been sitting on decisions. They were waiting for my approval on the smallest things. And that's when I realized that I hadn't been protecting the quality. I'd been protecting my own ego in a way while accidentally training my team to be dependent on me. So the real cost of not delegating isn't just your time, it's the opportunity cost of what you could be doing instead. Every hour that you spend on a task that someone else could handle is an hour that you're not spending on strategic work that only you can do. It's an hour you're not investing in developing your team, and it's an hour that you're not creating the kind of value that actually moves the needle. So when we talk about how to develop a delegate effectively, we need to understand why it's hard to begin with, why we can't begin to do this. Because if you're like most high achievers, you've got some pretty compelling reasons for keeping everything under your control. You think you're the only one that can do it great. And that's the first thing. It's the quality concern. You tell yourself that no one else can do it as well as you can, and you know what? You might be right initially. But here's what you're missing: Delegation isn't about finding somebody who can do it exactly like you. It's about finding someone who can do it well enough and then helping them actually get better over time. You see, I once worked with a CEO who refused to let anyone handle client presentations because he was gifted at it, is what he said. But his insistence on doing every single presentation himself meant that he was spending 60% of his time on doing something that, yes, it was important, but it wasn't the highest and best use of his skills. And meanwhile, his team never developed presentation skills because he never gave them the chance to practice. And second, it's the time trap. You think it's faster to just do it yourself than explain to someone else how to do it. This is classic short-term thinking. And guys, I have been there, I have done this. Yes, it's going to take longer upfront to train somebody, to create systems, to check their work initially. But that's the investment. And that's the investment that pays dividends forever. Every minute you spend training someone to handle a task that's reoccurring, it buys back hours of your time and your freedom in the future. And finally, this is the big one. There's the control issue. Deep down, a lot of us believe that we're not directly involved in everything. Something is going to be wrong, and it's going to be our fault. This is where we need to have an honest conversation with ourselves about what really is driving the need for this control. Is it about the work? Maybe it's about our identity. Are we afraid that if that we become indispensable? We may not be valuable, then it becomes an ego thing. And then we have to go through a mindset shift. The biggest breakthrough in my own journey with delegation came when I stopped thinking about it as giving up control and started thinking about it as multiplying my impact. So I had to ask myself, how can I make sure, instead of asking myself, I should say, how can I make sure this gets done right? I started asking, how can I create a system or systems that ensures that this gets done right, even when I'm not involved? And that shift changed everything. Instead of being the person who does the work, I became the person who helped them figure out how to get it done. Instead of being that single point of productivity, I became the force multiplier for the entire team. Think about it this way: if you can personally handle 10 tasks at your current level of quality, but you can train and support five people to handle those same tasks at 80% of what you can do, you've just created 50 units of output instead of 10. And here's the kicker. Over time, with the right support and feedback, those five people are just going to get better and better every single time. Some of them might even surpass what you originally could do. The key is to stop measuring your value by how much you personally produce and start measuring it by how much you're enabling others to do. It's not about being lazy or disengaged, it's about becoming strategic, about where you apply your unique skills and your knowledge. Now I want to get practical with you for a second. How do you actually do the work of delegating effectively? I've developed a little bit of a framework that I call the clear method, and it's transformed how I think about handing off responsibility. So starting with C, C for clarity. Before you delegate anything, you need to be crystal clear about what success looks like. Don't just say, oh, handle the Smith account. Instead, say maintain weekly communication with the Smith account. Keep the project timeline updated in our system and escalate any budget concerns over$500 to me immediately. The more specific you are about your outcomes and your boundaries, the more confident not only you are going to feel, the team members are going to feel as well. L is for link. Connect with the task to a bigger picture. Help your team understand not just what they're doing, but why it matters. Everybody wants to understand the why. When someone understands how their work contributes to larger goals, they're going to make better decisions. They're going to take ownership. And instead of just assigning tasks, you're inviting them to be part of the mission. Then we have E. E is free quip. Make sure that they have everything they need to succeed. It's not just about the resources and tools, because yes, those matter, but it's also about the knowledge, the authority, the access. If someone needs to make decisions, make sure that they have the authority or autonomy to make them. And if they need information from other departments, make sure that they have access to it. Please set your team up for success. Don't set them up for struggle. Then we have A. A is for agree. This is where you establish checkpoints and communication protocols. How often are you going to check in? What warrants an immediate conversation versus something that you talk about weekly? And when is your re when is your review of this work going to happen? It all goes back to it's not about micromanaging, it's about creating a safety net that allows both of you to feel confident about the arrangement that you've made. And then finally, R is for recognize. Acknowledge that both efforts, the efforts and the results. When someone takes on a delegated responsibility and does it really well, make sure that they know you've noticed. It's not about being nice, but it's about reinforcing behaviors that you want to see more of. And recognition is really what transforms that delegation from a one-time transaction into something that you can sustain over time with many different areas of your business. Now, even with a good framework, there's good, there's some pitfalls that can derail your delegation efforts. We've all had it. I'm going to share with you of uh the ones that I see the most. And the first is what I call the boomerang delegation. This is when I just love it. You you delegate something, but then you keep taking it back. Maybe they ask a question and instead of coaching them through it, you're just like, oh, never mind, I'll handle it. But maybe they do it slightly different than you would have done it, and then you redo it. But every time you keep doing this and you keep what I say meddling, you're sending them a message that you don't trust them to handle it. And that's not fair to you, and it's not especially not fair to the team member that you delegated it to. So please try to stay away from boomerang delegation. I've done it myself, and I know that it's not fair. The second mistake is delegating the task, but not the authority. So you ask somebody to manage a project, but then you require them to get your approval on everything. It doesn't matter how big or how small. You want them to handle a client relationship, but you don't give them the authority to make any uh concessions, or you don't allow them to solve any of the problems without actually talking to a first. And again, that comes down to frustration. And it defeats the purpose of what frustration really is supposed to be about. And the third is delegation without development. You hand tasks off, but you don't invest in helping the people actually grow into them. Remember that delegation is a skill that your team members need to develop, just like anything else. They need feedback, they need coaching and opportunities to reflect on what is working and what is not, because ultimately that's what's going to help them grow. When you get delegation right, something magical happens. It creates what I call the compound effect of productivity. Each person that you successfully delegate becomes someone who can handle more complex responsibilities. They develop judgment skills and confidence, and over time they become people that you can delegate even bigger and more important things to. I've seen this play out in my own career. Team members I invested in early on are the ones that, and I the ones that I've took time to actually train properly and give authority to and supported me through my learning curve and me through theirs, those are the people who now run entire parts of my business. They're not just executing tasks, they're they're making strategic decisions and developing their own teams and creating value that I could never have created on my own. And they're taking what I taught them and they're teaching other people. And here's the really powerful part when you delegate effectively, you're not just freeing up your time, you're creating opportunities for other people to grow and to contribute at higher levels and to develop their own careers. You're becoming the kind of leader that people want to work for. Someone who invests their development rather than just investing their time in someone. So if you're ready to start delegating more effectively, here's how I'm gonna suggest you begin. Start small and start with the right people. Look for somebody on your team who's shown good judgment, and maybe they ask really thoughtful questions or they seem eager to take on more responsibilities. Don't start with your most critical task, but start something that's gonna challenge them, but not ones that are really, really critical. And choose something that happens regularly, like a weekly report or a routine check-in with a client, maybe a standard process that you've been handling. And use the clear framework to delegate it properly. Be patient, though, during that learning curve because you need to resist that urge to boomerang it and to take it back. Track your time for the week before you start delegating and then track it again a month later. This is the fun part. You're gonna be amazed at how much mental space that you've created when you're not constantly switching from one strategic thinking thing to a tactical execution and you're kind of doing it all. But most importantly, remember that delegation is a skill and you're developing too. You're gonna make mistakes. You're going to delegate the wrong things to the wrong people at the wrong time. And that's okay. It's part of the learning process. The key is to treat each delegation as an experiment and learn from what works and what doesn't and keep refining that approach. So as we wrap up, I want to leave you with this thought. Your highest contribution isn't doing the work, it's multiplying the work that gets done. When you delegate effectively, you're not just being more productive, you're being more strategic about where you apply your unique value. The transition from doing everything yourself to leading it through others isn't always easy, but it's absolutely essential if you want to create impact at scale. It requires you to let go of short-term satisfaction of completing all of those tasks and being that little vacuum cleaner that picks everything up in favor of long-term satisfaction of building something that's bigger than what you could possibly create alone. Remember that delegation isn't about finding people to dump work on. It's about finding people to invest in and about creating systems that work without you so you can focus on the work that you can own, that you can do, and that you're really good at and that you enjoy. It's about becoming the kind of leader who doesn't just get things done, but helps other people become the best versions of themselves. So your challenge this week is identifying one task that you're currently doing that somebody else could handle. Apply that clear framework, take the time to delegate it properly, and then please resist the urge to take it back. Don't boomerang it when it's not done exactly how you would have done it. You need to trust the process, trust your team, and trust that by letting go of control, you're actually gaining something much more valuable the ability to create impact at a scale. And that's only possible when you're not trying to do it all by yourself.

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Jennifer Johnson

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