Delegating vs. Dumping: Are You Bad at Delegating?

For years, I thought I was bad at delegating. I'd hand something off to a team member, they start working on it, and then they'd come back to me and ask, should I be doing this way or that way?And what do you think about this approach? And can you just take a look at this really quick? And that would make me think, am I so hard to work for?Am I such a perfectionist or a control freak? Maybe I just need to hire better people. Maybe delegation is just not my thing. Maybe I'm the problem. But here's what I finally figured out.I wasn't bad at delegating. I was bad at setting them up for success. And once I changed how I delegated, everything shifted.In this episode, I'm going to show you why delegation keeps failing and more importantly, how to fix it. Because if delegation feels like micromanagement, at first, you're doing it right. Yes. You heard that right. Let's talk about this.Here's a reality check. I worked with a founder. We'll call her Kate. Kate had a small team of very good people.They were smart, they were capable, but they kept coming back to her with questions. She delegated tasks like, can you handle this client project for me? And a few days later, her team asked, should we do A or B? We're not sure.She'd answer. They'd go away, and then they'd come back and ask, what about C or D? Kate was frustrated.She thought I hired them to take care of things, to take things off my plate, but I was still making all the decisions. She ended up thinking she was the problem, but the problem was how she was delegating.She'd hand off a task, but she didn't hand off the context of the task. She didn't explain what success looks like. She didn't clarify what they could decide on their own. And she didn't set up a clear check in rhythm.So her team was guessing. And when you're guessing, you ask questions. A lot of questions. Her team wasn't bad at their jobs. They were just trying to read her mind.And luckily, that's impossible. So here's the shift. Before you delegate, you'll answer three questions out loud together with the other person.Those three questions will change everything. And I'll tell you what they are in just a minute. First, delegation isn't about handing off the task and hoping it works out.It's not about blindly trusting someone either. It's about setting them up for success. Think about it like this. You don't just throw a kid in the deep end of the pool and say, hey, figure it out.That's what happened to my mom, by the way, and she never learned how to swim. You teach them. You show them what good swimming looks like. And you tell them, keep your head up, kick your legs, use your arms like this.And then you let them try. You watch from the side, you step in. If they're drowning. That's what good delegation looks like. You set them up and then you step back.But here's what most founders do. They say, handle this client project with no context, no clarity, no guardrails. And then they wonder why their team keeps coming back with questions.It's not because your team can't handle it. It's because you didn't give them what they needed to handle it properly. Okay, now for the three questions that will move you forward. Question 1.What does success look like? It shouldn't be. Just handle it. It will be fine. Instead, try here's what done looks like you. Here's the outcome I'm looking for. Be specific.Here's an example. Instead of can you handle the Q4 planning? Try this.I need a Q4 plan with three to five priorities, a timeline for each, and who's responsible so everyone on the team knows what to focus on and can start executing immediately. If you can't define success for your team, they're going to guess. Their guess probably doesn't match what you want.Question 2 what can they decide without you? This is a key that most founders miss.You need to tell them here's what you have full authority on, and here's where you need to check in with me first.For example, you can decide which format to use, when to schedule it, who to invite, but check with me before finalizing the budget, changing the timeline, and adding new priorities. Without this, they'll either ask you about everything or they'll make decisions you're not comfortable with. And neither works. How do we check in?Don't just say, let me know when you need anything. Set the rhythm. So for example, let's do a quick 15 minute check in every Friday.You show me where you're at, I'll give you feedback and we'll course correct if needed. This prevents constant interruptions and they know when they'll have your attention so they can stop asking for it every hour.Now let me show you what this looks like. In practice you used to say, can you handle this client project?But with the three questions asked and answered, you now say, I need this client project Completed by end of month, success looks like this. I want the proposal sent, the contract to be signed, and the first milestone to be delivered.You can decide on the timeline, the resources needed, how to structure the work. Check with me, though, before finalizing the pricing and the contract terms. Let's check in every Monday for 15 minutes.Now they know exactly what to do. They can make decisions confidently and only check in with you at the agreed times. You get updated and give feedback at regular intervals.And you don't get interrupted constantly. See the difference? Same task, different setup, completely different outcome. Let's wrap this up. Here's what I want you to remember.If delegation feels like micromanagement at first, you're doing it exactly right. Your team doesn't need you to be involved in every decision along the way.They just need you to clarify upfront about what success looks like, what they can decide, and when you'll check in. That feels like micromanagement, but it's not. If you give them that, they'll run with it. If you skip it, they keep coming back.So the next time you delegate something, take five extra minutes. Answer those three. What does success look like? What can they decide? How do we check in? That's it. Five minutes. Save you hours of back and forth.So here's my question for you. What's one thing you're trying to delegate right now that keeps coming back to you?Think about it and then just ask yourselves, did I answer those three questions? If you didn't, that's probably the problem. It's not. Then set your team and yourself up to win, and then step back.That's when delegation actually works.