Bullish: How to Delegate, And Why It’s Important Even If You Just Make Coffee

Jennifer Dziura writes career advice for The Grindstone on Fridays and life coaching advice for our sister site, TheGloss, on Tuesdays.

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.

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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.

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    • Ewa

      God, what a great idea. But: where I’m from, TAs are more unique than unicorns (I am an English teacher); I dread the very thought of asking anyone to correct my students’ tests (my tests!!) and essays for me; I’m childless, and thus hiring someone to clean my flat for me would make family think I’m a lunatic. As a teacher – among others – yourself, do you see anything a lit/writing teacher could delegate?

    • Jennifer Dziura

      Hi Ewa,

      What a great question. Yes, some jobs make delegating basically impossible. In your case, though, aren’t there some things you can delegate to the students themselves? (I do seem to remember once having had a Very Important Job cleaning chalkboard erasers). I certainly remember many tests after (multiple choice, spelling, etc.) after which we would pass our papers to a classmate and peer-grade.

      For essays or more complex work — what if you anonymized the papers and then did a round of peer grading? (I assume people turn in papers as Word/text docs, and you could replace the names with codes, or have students turn in papers with cods instead of names?) Of course you’d still give the “real” grades, but it certainly helps that the papers have already had a go-round.

      Fortunately, I teach people to take computer-based exams, which display a student’s score immediately after the exam; the results of multiple exams are fed into a database that then calculates results about each student’s performance (so there’s nothing for me to grade). I’ve seen somewhat similar systems among my private school students — for instance, a multiple-choice homework assignment for history, to be completed online. Of course, English is one of the hardest subjects to move to auto-grading.

      Also, of course, I write all the time about multiple income streams. So, of course I’m going to suggest that you start a business. I remember one teacher at my high school who owned a number of hot dog (or slushee?) stands on the beach — a perfect seasonal business, and one in which he could employ his favorite students.


    • Ewa

      Hi Jen,

      Thank you for having taken the time to answer my question. It did, however, make me realize how hard it is to delegate – or ‘delegate’, even – anything in my situation. Not only are the students in my country completely unused to peer assessment, but also the teacher who would attempt to introduce it in her/ his classroom would most likely be accused of laziness and/or incompence. Oh joy. Evidently I must stick to delegating whiteboard erasing and arranging papers.

      Regarding summer jobs for language teachers in non-English speaking countries, I have a tip to share: a friend of mine is a tour guide in the summer, and it works fine for her:)


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