Damned if You Do, Damned if You Delegate

Have you ever felt like leading is sort of like being a parent trying to teach your kid how to ride a bike? You’re constantly balancing between holding on to keep them from falling versus letting them go to wobble their way to eventual success.

This has played out many times in my own leadership journey. Delegation is an area of struggle for most of us… Even to the point of feeling guilty and frustrated. “I know I should delegate more, but…” is a common phrase. Delegating is supposed to lighten your workload, but it often leaves us feeling even more overwhelmed. Delegation feels like a classic case of damned if you do and damned if you don’t.

We can’t do it all, but that’s never stopped us from trying.

This is more than just a personal struggle. When we insist on doing everything on our own, our entire organization suffers (not to mention our personal lives). Projects get bottlenecked, team morale drops, and creativity grinds to a halt. Worst of all, burnout can start to rear its ugly head. We can get overwhelmed to the point of making mistakes we wouldn’t ordinarily make. Can you relate? I know I do.

If delegating is so important, why is it so dang hard? Delegation can feel a lot like parenting. I had very little to do with teaching my then 6 or 7-year-old how to ride his bike. But, even as he was getting the hang of it, I couldn’t help but hover nearby…ready to catch him if he started to topple over.

The Truth? Delegating is a giant pain in the ***!

Let’s face it. Delegating tasks can be hard. I’m someone who really enjoys collaborating, spending time with people, and teaching others, but it still feels like nails on a chalkboard. Here’s why:

1. The process is less efficient. I remember trying to teach my oldest son how to tie his shoes - in many ways still a developing process. It’s frustrating and feels like it takes forever (make those bunny ears, dang it!). When you delegate, you often find yourself still involved, turning what seemed like a simple task into a marathon of explanations and check-ins.
2. The results are unpredictable. The old adage “If you want something done right, do it yourself” didn’t come out of nowhere. The fear of unpredictable results can make you want to clutch your task list tighter than the armrests of your office chair when you’ve leaned back a little too far (just me?). Many times you end up doing it yourself anyway. There’s just a whole lot more sighing…and maybe a bit more cursing.
3. It feels like more trouble than it’s worth. Explaining, training, and overseeing someone else can seem more troublesome than handling it yourself. It can seem like a whole lot of pain with very little gain.

“I thought delegating was supposed to make things easier for me?!”

Delegating tasks to others doesn’t always provide the relief we expect. It takes more effort for less predictable results, which is really frustrating. Delegation doesn’t necessarily help ~me~. And wasn’t that the point of this whole delegation thing to begin with?

I’ve faced these exact challenges in both my professional world and as a parent. While watching my boys struggle through social situations or trying to help them with their homework, I know how hard it is to find that balance between stepping in or letting them figure things out on their own.

The same is true in leadership. You want to help your people, but you also want your team to learn and grow themselves. Not to mention, there’s work that has to get done!

The Shift: From Self-Focused Delegation to Team-Focused Empowerment

Here’s where the magic happens. Delegation is like holding onto the bike seat and never letting go. Empowerment, on the other hand, is like letting go of the seat, knowing they might wobble but will eventually ride confidently on their own. It’s about enabling rather than just delegating.

This shift is moving on from just offloading tasks to truly investing in the growth of your people. It’s changing my focus from asking other people to get things done for me (short term) to helping others accomplish things for all of us (long term). Empowering others is about giving people the tools, trust, and autonomy to succeed. This shift transforms leadership from self-focused to team-focused.

As long as delegation is about making MY life easier, I’ll never see it through. It will always be easier for me to just do the tasks myself. But, these short-term gains stem from the long-term health of myself, my organization, and my team. It’s like working out or eating better…it may not be as fun in the short term, but it is much healthier in the long run.

Empowering others isn’t without challenges. It requires time, trust, and the patience to let go. Mistakes will happen, but they become learning opportunities for growth…both for the people I work with but especially for me.