A Playful Take on the Challenges of Coaching

Leadership challenges are no laughing matter. Except for when you ask ChatGPT to write about them in a playful tone. Then…they’re HILARIOUS!

The reasons why leaders don’t coach their team members are pretty straight forward. And BORING. Here are the top five:

  1. Lack of time

  2. Lack of coaching skills

  3. Fear of being seen as weak

  4. Resistance from team members

  5. Limited resources

Then, I asked ChatGPT to write a blog post about the five reasons above, but to do it in a playful tone. I laughed so hard when I read it, and I decided that it was just too good not to share. Enjoy!

Here’s what ChatGPT says about these challenges:


Yo, leaders! Coaching your team members can be tough as nails, am I right? It's like trying to herd cats or teach a dog to ride a skateboard. But why is coaching such a pain in the butt for so many leaders? Let's dive in and find out.

  1. Ain't Nobody Got Time for That

Let's face it, you're a busy bee. Between endless meetings, putting out fires, and trying to get your inbox under control, finding time to coach your team members can feel like Mission Impossible. When you're stretched thin like a rubber band, coaching can seem like just another item on your never-ending to-do list.

2. Skills, Schmills

Coaching requires some serious skills, like listening actively, giving feedback, and asking open-ended questions. If you're not a natural at this stuff, coaching can feel like trying to juggle flaming pineapples. It's a lot easier said than done.

3. Fear of Looking Like a Weenie

Nobody wants to be the boss that gets walked all over. Some leaders avoid coaching because they're worried their team members will see them as weak or ineffective. But let's face it, avoiding coaching just because you're scared of what your team will think isn't exactly a boss move.

4. When Your Team Members Are Like "Nah"

Coaching is a two-way street, and sometimes your team members just aren't into it. They might feel like you're criticizing them or just not want to hear what you have to say. It's like trying to give advice to a cat - they might just give you a big ol' middle paw and walk away.

5. Resources? What Resources?

If you don't have the right tools for the job, coaching can feel like trying to build a house with a toothpick. Maybe you don't have the time, the budget, or the staff to really prioritize coaching. It can feel like you're stuck between a rock and a hard place.

In conclusion, coaching is a tough nut to crack, but it's also super important for building strong teams and driving results. So if you're struggling with coaching, take heart! You're not alone. By recognizing the challenges and working to overcome them, you can help your team members grow and achieve their full potential.


I love the earnestness of the last part. It’s true—when you tackle these challenges, your team members WILL grow and realize their potential. That’s why WE’RE here. Academy of Areté has your back!

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