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

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.

Yet, I still felt pretty silly sometimes. She’d show up with my Starbucks in hand, and I’d be all stressed out because I hadn’t figured out a list of things for her to do. Sometimes, I’d give her the easiest item on my list, even though that item wasn’t very important. Then, something that didn’t really need done at all would turn into a bigger task than it ever needed to be, since of course my assistant wanted to do well (at least at first – after awhile, she probably got sick of my vague pronouncements).

So, there’s something I really suck at. But, as I very regularly express in these columns, I never believe that that’s an excuse to continue sucking at something. We are all born illiterate, drooling, incontinent babies – anything that other people know how to do, they’ve had to learn, and you/I can, too.

(See last week’s Bullish: Occupy Wall Street Will Affect Your Career – How to Succeed Without Being An A**hole for more on improving your skills for free, even in times of trouble and torment. I also discussed my personal assistant adventures in Bullish: What to Charge for Your Work and What to Pay Your Assistant.)

If You Are Going to Become A More Awesome Version of Yourself, You Will Need to Delegate

If you are bullishly improving your skills at every turn, soon, you will be able to do many more useful and lucrative things than you can possibly do in a day.

This is, in fact, my current situation. I am able to (successfully) pitch many more projects than I can follow through on. If I could work twenty hours per day, I could sell those hours to people who wanted my services. I hope I don’t sound like an asshole saying that; it’s true, and it’s a place I hope I can help others reach as well. (See Bullish: How to Run Your Career Like a Business.)

When your abilities outstrip the number of hours available to you, you will have to delegate.


This means that you will sometimes have to assign tasks to people who cannot do them as well as you would do them. That’s okay.

It also means that sometimes you can go to bed, knowing that someone else is getting your work done halfway across the world while you sleep. My web designer in Argentina gives me exactly this feeling of satisfaction.

If You Grew Up Blue-Collar, You Might Find Delegating Uncomfortable

I spent a good bit of my billable hours tutoring the children of the wealthy. I don’t actually have any Gossip Girl style stories – mostly, they’re pretty reasonable people with reasonable goals for their kids. The kids have their own problems; having parents with money doesn’t really smooth over adolescence all that much.

But one thing that’s always struck me is that the wealthy have almost zero privacy: their houses are full of assistants and maids and workmen and decorators and, in one case, a professional “stretcher” (a guy who came over with a massage table to help my student’s dad stretch).

So, if you grew up blue-collar, or with certain other cultural norms, you might find it really troublesome just to hire a maid. When I finally did this, I had to justify it to myself mathematically – here’s what I make per hour, and there’s no shortage of hours during which I can do it. I have infinity freelance work, and I make way more than the maid. So…now a nice lady is cleaning my bathtub, and it’s weird.

(For a “delegation” classic on how to treat people in developing nations like fun new toys, check out this article, which appeared in The Four-Hour Workweek: My Outsourced Life: A true account by AJ Jacobs, editor-at-large at Esquire magazine. So, don’t be a douchebag. Thank you.)

I wrote in Bullish: Social Class in the Office about how blue-collar values can hold you back in the workplace (a workplace often full of mincing yuppies whose mealymouths can never produce cogent and forceful thoughts with direct language!), but can also be an advantage. I wrote last week that, in a time of austerity, knowing how to “be cheap and work fiendishly” can be a great advantage in doing business in hard times.

But sometimes, we just have to get over this kind of discomfort. I want you to run your career like a business, and businesses have employees. There is nothing wrong with that. Hell, you could become a “job creator.” (The real kind.)

(See also Bullish: Money-Saving Tips That Don’t Involve Bread Bags or Baking Soda and Bullish: Are You Under-Reinvesting in Your Career? for more on thinking productively about money.)

The Stages of Delegation

According to Robert Heller, author of How to Delegate, there are five stages to delegation: Analysis, Appointment (as in, appointing the right person for the task), Briefing (telling them what the task is and how success will be measured), Control, and Appraisal.

In the Analysis phase, one challenge is to eliminate unnecessary tasks entirely. When you find yourself in a management position, it’s easy to pass off the stupidest stuff, leaving all the crucial tasks for yourself.

In the Appointment phase, it’s important to “Show faith in your chosen delegate, even if others have reservations.” As your career develops, you will absolutely find yourself in the position of giving out tasks to others that you know almost absolutely will end up getting done less well than you would have done them. The U.S. Marines have something called the “70% solution”: for many tasks, 70% is all that’s needed. Sometimes it’s the best that can be done with limited information or resources. Accepting a 70% solution now can help someone else develop skills that ultimately exceed yours. Which is pretty cool if you manage to keep that person around.



Briefing is some tough business. Heller writes, “Whatever the role, proper briefing is essential – you cannot hold people responsible for vague or undefined tasks.” When learning to delegate, briefing often does, frustratingly, take longer than just doing the job yourself. But those are the growing pains you have to go through to develop a team, run your career like a business, and expand your ability to act upon the world by managing others.

Reading Heller’s notes on the Control phase reminded me of one of my least favorite things about my childhood: I would be trying to study, and my mom would yell from the bottom of the stairs, “Jennifer, get down here and help me!” (Even now, I really get mad at boyfriend-dudes who interrupt my concentration.) I would come downstairs, and what she wanted was for me to stand in place for ten minutes and stir her spaghetti so it didn’t stick together (we’re not Italian, but we ate a lot of spaghetti). I offered to learn to cook and to cook one night a week, instead of doing some tiny fraction of the cooking every goddamn night. No dice. I don’t think it was great for either of us; I never got any credit or satisfaction for making an actual meal, and my mom had to supervise a surly teenager who couldn’t wait to get back to AP Subject du Jour. I did learn one management lesson there: humans are creative beings, even the ones who do accounting all day. People need some autonomy over their work product or they lose the desire to do well.

Finally, the Appraisal phase. Heller suggests making sure to praise people publicly. If you’re a lone wolf managing a freelancer, praise publicly be sending a referral email (“I wanted to recommend X, in case you ever need someone to run your small business’ social media”). In Bullish: How to Win When the Workplace Runs on Feelings, I suggested that you get over any ire you might feel at having to thank people for just doing their jobs – saying “thank you” doesn’t cost you anything, and you can do it any number of times per day without slowing you down.

Why Now?

I know that “delegating” doesn’t sound like the most exciting subject in the world, but it’s an important step in your empire-building. As Heller writes, “Delegation involves the loss of direct control but the retention of overall responsibility.”

What am I doing over here in Bullish-land? Well, I have 1) business ideas that work well together, 2) over 20 clever domain names for these businesses, 3) startup capital. What I don’t have is the ability to work more than 8-12 hours a day, at best. It’s time for an employee. I’ll update you on my business plans as they develop.

But until then: practice delegating! As you become a more awesome version of yourself, it will become the only way to move to the next level.

originally published on The Grindstone

Our Latest Products