I was once very, very bad at delegating. In fact, when I ran an internet marketing firm (in the early 2000’s), I regularly sat at my cheap fiberboard “executive” desk, head in hands, starting at a leviathan, well-cataloged to-do list that took the form of seven individual Word documents, each containing several hundred items.
In the other room of my small office were 2-4 employees, some of whom had basically nothing to do.
Like a sad, deeply limited cartoon character, I would look back and forth between this list, and some dudes tossing a Nerf ball, and the list, and the dudes, and then sometimes I would dive deep into escapism by looking up the requirements for joining the Marines, where at least someone would tell me what to do and I could hit things.
And then I would pay the paychecks of the employees I was barely managing, and ultimately, of course, the company failed. (See Bullish: 3 Career F*ckups I Made So You Don’t Have To).
According to How to Delegate by Robert Heller:
“Delegation takes time to organize and prioritize, but the costs of avoiding it are high. The manager who does not delegate or who delegates ineffectively will not only seem disorganized, but will spend many hours each week completing low-priority tasks. This can result in excessive hours worked by senior managers, low morale among underemployed staff, basic process slowed down by bottlenecks, poor quality of work, and missed deadlines.”
Yep, that pretty much describes my plight as a twenty-two year old entrepreneur.
Years later, I hired a personal assistant. That went a bit better. I was upfront about my lack of management talent. I said, in the Craigslist job posting, “It’s a mess over here. Here are fifty things that need done in my life. Can you do any 15-20?”
The woman who replied could indeed do 15-20 of those things, and sent me a rather ballsy email about it. Typical personal assistant postings on Craigslist at the time were offering $15-17/hour, so I offered $20, and she wrote, “Considering the depth and relevance of the skills I have to offer, I am requesting $25.”
She had to have known that I would get dozens of people wiling to work for less. Asking for more made her stand out. I hired her, at the rate she requested, and over the next year, she spent 10-20 hours a week at my place, sending press releases and also filling my fridge full of peeled hard-boiled eggs. She was extremely competent, and has since moved on to her own television show.