Learning is hard.

Often I don’t have as much empathy as I should when teaching someone.

“Just click here.”

“We went over that yesterday.”

Audible sigh.

But now, I’m learning Pickleball and everything about it seems unnecessarily complicated to me.

I’m sure later on, when I’ve got the hang of it, the elaborate regulations about where to stand, how to score, and when the ball has to bounce will make more sense.

But right now, I keep breaking the rules. Even after being corrected by the coach. A dozen times.

I simply have no muscle memory at all.

I come home exhausted, feeling overly supervised and micromanaged.

I’m doing my best to remember these feelings when I’m the instructor.

The case against delegating.

I witnessed a colleague take about 2 hours to backcheck the math on a task he had delegated to his assistant.


To be sure, the task was high stakes and involved writing checks in the correct amounts, so it was 100% appropriate for him to double-check the math.


But, this was the exact same task I do myself in about 30 minutes a week, with the help of a bit of software automation.


All to say, try to automate before you delegate.


(Full disclosure, I’m the world’s worst delegator, so automating started as my coping mechanism. But time and time again, I’ve noticed automation often saves more time over delegating.)

It’s not a phone.

It looks like you’re negotiating a merger. But you’re really playing Candy Crush.

And nobody even uses the phone function much.

I propose we call it what it is:

a TV,

a gaming system,

an entertainment device in your pocket.

“Where’s my phone?” sounds so legit that calling it a phone likely reinforces its use. Nobody will argue that a nurse, businessperson, or mom needs their phone.

But try calling it something else. Something more honest.

“Where’s my pacifier?” sounds just crazy enough that it might just nudge us to put it down.

The sorcerer.

I love to bush-whack a path at work.

This way, when it’s time to delegate a task, I’m clear about how long it will take and the obstacles someone will likely face when completing it. 

Last week I delegated a task and got the following pushback:

“I can’t possibly help on such a huge task right now.” 

Because I had done this same task in the past, I knew it was a quick tweak, not anything that needed coding or technical expertise. 

What I was asking to be done would’ve taken five minutes.

I lost lots of trust during this interaction.

Yes, sometimes things will be demanding and require time, skill, and even sorcery.

But since it’s a cinch to watch a YouTube video or Google some instructions, you can quickly lose credibility by pretending to be the Wizard of Oz.

Pretending to care.

Lots of companies have the word “care” in their mission statements.

But in my experience, the care I get as a customer often feels fake. 

It’s as if companies have a “caring template” and are following an outlined script.

“Welcome to, ABC Company. 

I’m (insert first name). 

How may I provide an exceptional experience for you on this (insert weather) day?”

Contrast this with my experience at Brookline Booksmith:

I entered the humming bookstore, lugging a bin of heavy stuff for an event I was hosting.

“Will anyone here even remember that my event is today?” 

Seeing me struggle with my large bin, a young cashier jumped over the counter to grab it from my arms.

He then walked me to the table Riley had prepared for my arrival – Sharpies, stacks of books to sign, and a table-clothed covered table. There was even water in case I was thirsty (I was!).

Riley greeted me by name and welcomed me to the event – I felt like Julia Roberts!

Because none of this was scripted, it felt so good.  

Riley and the guy who jumped over the counter weren’t pretending to care – they did care.

If the word “care” is in your mission statement, start by hiring people who genuinely take pride in their work.