Let It Go: The Real Skill Behind Delegation and Growth

We’ve talked about FEED—what you give your team. We’ve explored FUEL—how you energize them. And we’ve unpacked FLAVOR—your authentic leadership style. Now comes the next focus: FLEX: Adapting to meet the unique needs of the team.

FLEX is your ability to adapt. To read the room. To pivot when needed. To let go, when the moment calls for it.

…

There’s a moment in every leader’s journey when you realize…

You’re the bottleneck.

Not because you aren’t capable, but because you’re trying to be too capable, too available, too essential.

You hold on. To the decisions, to the decks, to the inbox, to the approvals.

And somewhere along the way, what felt like dedication starts to look a lot like control.

I’ve been there.

I’ve watched leaders, especially from my own Gen X cohort, grind harder, take on more, and stretch themselves thin because somewhere deep down, we were raised to believe that letting go meant letting people down.

We don’t delegate, simply because we’re lazy. It’s actually more of the opposite. We struggle to delegate because we care.

But if we’re going to lead well, especially in this new age of hybrid teams and intelligent systems, we have to shift that mindset.

Because in today’s world, growth doesn’t come from doing more.

It comes from letting go.

The Dream We Grew Up On

If you’re part of Generation X like me, you didn’t just imagine artificial intelligence, you were raised on it.

When I was young, just like everyone, I watched Knight Rider and marveled at KITT, the talking, autonomous, self-driving car that could think, respond, and save the day. We tuned into Star Trek: The Next Generation where you could simply say, “Computer, make me my favorite meal,” and it would listen, always precise, always ready and generate whatever you ask. We grew up on Hollywood’s glossy vision of machines that could walk, talk, and think for us, from The Jetsons to Terminator, painting a future where technology might not just assist us, but become something like us.

As a kid, and even as a young adult, I saw AI as this magical concept: something sleek, powerful, and almost human, the kind of tool you dreamed of having at your side when life got complicated.

Well… here we are.

AI is no longer science fiction. It's here, in our inboxes, our calendars, our brainstorming sessions. It writes copy. It builds strategy decks. It gives us clean data in seconds. And yet, the fantasy never told us what it can’t do.

The Hollywood version of AI was clean and confident. The real version is smart but limited — fast but not wise.

We now stand in a reality where tools can perform tasks… but they cannot lead.

They can prep the work… but they cannot read the room. They can mimic language… but not intuition. They can analyze performance… but not the heart behind it.

As Generation X steps fully into senior leadership, we’re now forced to grapple with a strange truth: We finally got the technology we dreamed of, and we’re learning it’s not a replacement… it’s a responsibility.

The real challenge now? Learning when to rely on it… And when to lead beyond it.

Delegation: The Leadership Skill That Scales

Delegation is not a soft skill. It’s a strategic imperative.

And yet it’s one of the most underdeveloped muscles in leadership today.

Why?

Because it requires trust. It requires clarity. And it requires something most high-performers struggle with, surrendering control.

In Episode 3 of the OpenAI Podcast, the speakers touched on something that stuck with me: in a world of increasing automation, emotional intelligence will remain the defining skill of great leadership.

Machines can generate, calculate, and predict. But they can’t sense. They don’t know when a team is demoralized. They can’t tell when timing feels off. They don’t feel the subtle shift in energy when someone’s disengaged.

That’s your job. That’s EQ.

And in today’s world, EQ isn’t just about leading people. It’s also about knowing when to delegate to AI, and when not to.

Because smart delegation today means learning to trust both the humans and the agents around you.

The Gen X Delegation Dilemma

Let’s be real, many Gen X leaders are caught between two worlds.

We grew up with landlines, floppy disks, and bosses who expected you to figure it out alone. Now we’re leading in a world of Slack threads, AI assistants, and talent that expects trust, not micromanagement.

And it’s hard to rewire.

But research shows: the Gen X tendency to “do it all” is one of the biggest blocks to leadership scalability. We step in when we should step back. We “save the day” instead of developing others. And we lose sight of the one truth every leader has to face:

You can’t scale yourself.

But you can scale your impact.

And that starts by seeing delegation not as a handoff, but as an investment.

Delegating in Two Directions

In the past, delegation meant assigning tasks to people. Now, it means something more dynamic:

• Delegating to People, with clear purpose, measurable goals, and support that helps them grow.

• Delegating to AI, offloading prep work, content drafts, data pulls, meeting summaries, and even creative ideation so you can spend more time leading.

This is where EQ and AI come together.

You don’t delegate everything. You delegate intelligently.

You let AI prep the draft, and you bring the soul. You let the data surface insights, and you bring the context. You let the assistant generate the email, and you decide how to season the tone.

That’s leadership in the age of AI.

Try This Exercise

Next time you feel like you’re “too busy to delegate,” ask yourself:

• What’s on my plate right now that only I can do?

• What can I hand off to help someone grow?

• What can be automated, templated, or handled by an AI assistant?

• Where am I clinging to control, and why?

And then, let something go.

Start small. But start.

The Real Question

If you're holding it all, who's rising with you?

Delegation is not about reducing your value, it's about expanding your influence.

Great leaders aren’t known for how much they do.

They’re remembered for how many people they trusted, taught, and empowered, including the intelligent tools they learned to use well.

Because at the end of the day, leadership is not about being everywhere.

It’s about knowing where you’re needed most.

And trusting others, human and machine, with the rest.

Quick Recipe: Lemon-Herb Grilled Chicken with Avocado Salad Prep + Cook Time: 25 minutes

Ingredients:

• 2 boneless chicken breasts

• Juice of 1 lemon

• 2 tablespoons olive oil

• 1 teaspoon garlic powder

• 1 teaspoon dried oregano

• Salt and pepper to taste

• 1 ripe avocado (sliced)

• 1 cup cherry tomatoes (halved)

• 1 cup baby arugula or spinach

• 1 tablespoon balsamic vinegar

Instructions:

1. Marinate chicken with lemon juice, olive oil, garlic powder, oregano, salt and pepper. Let sit for 10 minutes.

2. Grill or pan-sear chicken over medium heat (6–7 minutes per side) until cooked through.

3. Toss avocado, tomatoes, and greens with a drizzle of balsamic.

4. Slice chicken and serve over the salad.

Wine Pairing: A crisp Sauvignon Blanc, bright, citrusy, and light enough to complement the herbs and richness of avocado without overpowering the dish.