Tuesday Email: Delegation

Read time: ~2.30 minutes

Happy Tuesday!

Every Tuesday I'd like to offer strategies for the week ahead and a thought to fuel your action.

You aren't bad at delegation, you're just unclear.

Delegation isn't just offloading tasks—it's an exercise in clarity.

It demands we abandon assumptions, get painfully specific, and trust deeply. If you can't explain what you want clearly enough for a five-year-old to grasp, delegation will frustrate you every time.

I know this frustration intimately. I'm a perfectionist with chronic imposter syndrome. In other words, I'm often a mental mess.

Years ago, leading my startup, I thrived on being the visionary. It felt good when others looked to me for answers. It validated my worth, soothed my insecurities, and momentarily silenced my inner critic. But it didn't last.

It was 8:12 on a Wednesday morning after the third resignation within two weeks. I sat silently in my car in our office's parking garage. Not wanting to get out of the car in fear of the next shoe to fall, I just sat, paralyzed to act. My pride and joy—my startup—was crumbling.

Sitting in the dim glow of a parking garage, I started replaying the past months. Slowly, painfully, a pattern emerged: every question circled back to me. Every decision waited for my approval. My supposed clarity had been a cloud of confusion.

The team wasn't quitting their jobs—they were quitting my lack of clarity.

Right there, in the stillness of that morning, something broke inside me—my illusion of control. I wasn't leading; I was suffocating my team, expecting them to decipher my cloudy vision, read my mind, and translate my silence.

From that moment, everything shifted. I stopped micromanaging details and instead obsessed over communicating clearly. I invested heavily in building relationships, trust, and processes. I shifted from owning every decision to clearly defining our destination, allowing the team the autonomy to chart their own course to get there.

I finally understood that delegation isn't about control. It's about clarity. It's about setting your destination, clearly communicating it, and letting capable people navigate toward it, exactly like entering an address into a GPS and trusting the route it provides.

Effective delegation sits between abdication (letting go without guidance) and micromanagement (controlling every step). It requires trust—trust in your people, vision, and process. Trust grows from clarity and authentic relationships. Just as a tree's fruit depends on unseen roots, successful delegation depends on invisible investments you make in your people.

Steve Jobs embodied this perfectly. He didn't micromanage every pixel, nor did he abdicate his vision. He articulated his expectations so vividly that his team could bring them to life authentically and passionately.

Delegation is also a staircase, not a cliff. It starts gently: "Do exactly this. "Then it moves to "Research and report," then "Recommend a solution," and finally, "Decide and inform." Each step builds confidence and trust, making eventual full delegation natural.

Today, whenever I'm tempted to say, "I'll just do it myself," I pause and ask: "What future am I sacrificing by not delegating this effectively right now?"

Delegation isn't just a skill—it's your leverage for scale, growth, and lasting impact. It's your path to becoming a FutureProof advisor who builds a firm that thrives beyond its individual limits.

Your legacy won't come from your solitary accomplishments—it will come from empowering others to accomplish greatness alongside you.

The best is ahead!

-Matt