187. The Delegation Dilemma

Why is delegation so difficult—even when we know it’s essential to leadership? 

In this episode, we explore the hidden emotional and cognitive barriers that keep leaders stuck in doing instead of leading. You’ll learn why delegation isn’t just a task shift, but a mindset shift—and how redefining success can unlock growth for both you and your team. Plus, hear a real-world story that shows why the discomfort of delegating is worth it. 

Looking for a community of leaders where you can tackle real challenges, share wins, and grow together—without office politics getting in the way? Join Leadership Thought Partners, a coach-led, group-directed space launching in July. Registration closes on June 22, 2025 at strongleadersserve.com/ltp! 

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Transcript

1:11

What makes delegation so hard? I know you like me, have probably been to all the classes and read all the articles you know about staying in your zone of genius and making sure that as you look at your tasks, you are giving other people the ones that they are able to do and you're only keeping the ones that you have the network or the skills or knowledge to be able to do. But it's still so hard. If you've ever told yourself, I know I should delegate more, but it's just faster if I do it myself. This episode is for you. Today, we're continuing our four episode miniseries based on the topics we'll be exploring in our upcoming leadership build series, a Hands-on Group learning experience launching this September. Last week we tackled difficult conversations. This week we're diving into delegation. Why it feels so hard when it's best not to delegate, and what actually changes when we start making our delegation decisions. In a more structured way and start delegating more effectively. In the coming episodes, we'll explore two more essential leadership skills leading through change, and managing up and influencing without authority. And here's the exciting part. These four topics, as I mentioned, will form the core of our next leadership build series, a powerful group experience using Lego serious play to explore and grow your leadership through creativity, reflection, and real world application. I'll share more about that and a special deal just for podcast listeners. In our final episode of the season coming out on July 2nd. Now let's dig into this week's topic, delegation. I'm Terry Schmidt, executive and leadership coach at Strong Leaders Serve, where I partner with compassionate driven leaders to transform potential into performance. And this is the Strong Leaders Serve Podcast. Now, I will tell you from my experiences personally as a leader and now as a coach, working with leaders, even experienced leaders struggle with delegation. Especially those who have built their careers by being the reliable problem solver, the person others turn to when something important needs to get done quickly and correctly. Does that sound like you in a fast-paced environment? When a task lands on your desk and you know that you can do it right and fast, it's hard to hand it off, not just because of time pressure. But because delegation often comes with discomfort, watching someone else fumble through it, feeling responsible for their mistakes, or even questioning your own worth when you are not the one executing. We protect ourselves from these uncomfortable emotions by doing the task ourselves. But here's the trade off. Every moment we spend doing. We're not leading. Delegation isn't just shifting a task. It's shifting our mindset from short-term control to long-term investment. I remember working with a leader, we'll call her Maria, who had built her career by being the one everyone relied on. She was fast, she was dependable, she was detail oriented. When she got promoted into a leadership role, delegation became her biggest challenge. There was one recurring report that took her about an hour each week. She knew that someone else on the team could learn it, but the thought of mistakes or having to explain it all felt like more work than just continuing to do it herself. Eventually, as the other leadership work piled up on her plate, she decided it was time to hand it off. And yes, there were a few bumps in the beginning, but months later, not only was that team member that she had handed it off to confidently completing the report. They'd actually improved it. Maria had gained back her time, and her team member had gained confidence and visibility. It is a simple example, but a powerful one. One that illustrates what I was talking about, how delegation isn't just about shifting a task. It's about shifting your mindset from short-term control to long-term investment. That one hour investment turned into a development opportunity and a shift in team dynamics that paid off far beyond the task itself. however, just like any leadership skill things aren't necessarily simple. I can't just tell you. You always need to delegate. In fact, there are times when it might be best not to delegate and to keep the task yourself. So how do you know when to delegate and when? It really might make more sense just to do it yourself. It starts by asking some grounding questions. Is this task time sensitive? Are the stakes high? If it's done imperfectly, is it a one-time task? Or something that recurs. If you delegate this, what could be the benefit six months from now? Could this be a development opportunity for someone else? And ask yourself also, am I holding on? Because I believe my value comes from being the one who executes it. If your answers to these questions point to urgency, high risk, or a one-time task that doesn't save time in the future, doing it yourself might be wise, but if it's repeatable, the timeline is flexible and there's growth potential for someone else, and you discover that maybe you're holding onto it just because you enjoy the value you get and the recognition you get from completing it. That's where delegation is likely to pay off. So let's say you've decided delegation is your best approach. The next step is to do some of the internal work that makes delegating more regularly easier for you. First, let's tackle how you can redefine your success and your value. What once was pretty clear cut. Your success was based on the tasks and projects you completed is now a bit more complicated. Think about it like this. As a leader, you're no longer the solo performer on the stage. Instead, you're the conductor on the stage coordinating a bigger, more complex performance. And that shift can be exciting, as I said, a bigger, more complex performance that has bigger results, but it also can be very uncomfortable. After all, we're used to being the fixer, the problem solver, the reliable doer. But leadership isn't about fixing everything yourself. It's about amplifying others. Creating the environment for growth, creativity, and long-term impact. The question becomes, what does success look like for you if it's no longer about you doing the work? Well, here's one idea that I've seen work. Start measuring your success with what I call the lift index. Think about all the results that you are trying to drive by delegating. Are people solving problems without you? Are they taking on new challenges with less support? Are you no longer needed in every meeting? Are you seeing team members who are maybe a little bit more quiet, speaking up in meetings? And taking ownership of different tasks, it's gonna look different for everyone, but I encourage you to think about, how can I see that my delegation is paying off and getting really concrete about some observations that you can make. I've even seen leaders put these observations or these specific pieces of evidence into a dashboard for themselves and keeping track of the number of times that they see it. So that they can calculate their own personal lift index. So maybe by now you're sold on delegation, you're resigned to setting the vision and having the team execute. You're following the adage that the leader sets the why and the what of the project, and the team sets the how. But before we end today, I wanna discuss how leaders can sometimes take that too far. I know from firsthand experience, as I was guilty of it as a leader, I fell into what I call the dino trap. That's DINO. What is that? Well, many new leaders worry about micromanaging, so they swing to the opposite extreme. They delegate and name only DINO. They assign the task, but they don't provide the context, the expectations, or the support that their team needs to succeed. They feel like they wanna give their team that control, but they don't give them enough to support or enough guardrails to actually execute the task effectively. Real delegation isn't about completely letting go, it's about scaffolding. If you think about scaffolding on a building, it creates just enough structure to support confidence and creativity without stifling ownership. One way to do this is with the three Ws and one H framework, so the three Ws. These are essential information for your team member to effectively execute on the task. The first one, why does this project matter? Second, what is the desired outcome? What does success look like? And the third, W, who is responsible for what and how do these pieces fit together? And then the H, how much freedom is there and what are the boundaries? If you can fit those three W's and one H into your conversation, when you're delegating the task, you will be well on your way to delegating effectively in a way that provides support and scaffolding for your team member and also. Make sure that what they come back with is going to meet your needs and the needs of the project. When you get this right, you'll also hit what educational psychologists love Vygotsky called the Zone of Proximal Development. The sweet spot where people stretch, struggle a bit, but grow. It's right outside their comfort zone, but it's where learning and leadership really happens. If you've ever wrestled with delegation, either clinging to control or backing off too far, know that you're not alone. In fact, you're exactly who this episode was for. I know that was just a short taste into delegation and what makes it so hard and how you can think about it differently to remove some of that discomfort. But we're gonna be doing much more in our leadership build series. That launches in September, we'll explore each skill, not just in theory but in community. And we'll utilize methods like Lego, serious play, deep reflection and peer support. Again, I'll be sharing the full details and a special listener only offer in our final episode of the season on July 2nd. Next week we'll talk about leading through change. Until then, keep leading with courage. And remember, strong leaders serve.