Writing this article as someone who has never owned a business (and never intends to), I approached the topic of delegation with curiosity after recently being traumatized by a seemlingly seasoned entrepreneur.

When I interviewed with this business owner about potential opportunities to do some copywriting for the company, said entrepreneur told me upfront: “I do the job of five people.” As a fairly new freelancer, I interpreted this as, “I need you, I want you, I can’t live without you. Please come work for me.” I was stoked.

After a fairly productive meeting, I sent in a draft of a press release and didn’t hear back until four days later—after several emails and calls asking for feedback—at 11pm the night before it needed to be published. The redraft my boss sent back did not contain a word I had written, was 10 times longer than mine and was full of errors. When I broached the subject, all I got was, “It was just easier to do it myself.” I was also told I had worked too many hours (five total at a reduced rate for researching the company, drafting a release, creating social media accounts and logging numerous errors on the site) and that I would not be paid for that many hours. I promptly tore up the “contract” that the business owner had never gotten around to signing and declined any compensation.

Lesson learned? I should have taken the, “I do the job of five peope” to mean, “I have issues with delegation and I can’t trust anyone to do anything because it’s just easier to do it myself.” Inspired by this entanglement, I decided to explore how entrepreneurs manage to delegate successfully, and how doing it all yourself can be bad for business. After searching for great delegation tips from some amazing entrepreneurs, below are some of the best ones I found:

1. Don’t be afraid to bring on a new team member.
We never followed a mold, so there was no structure in place to train others. Just the thought of handing over real responsibilities to someone else with our name and brand attached to it made us nervous. When we finally did hire a part-time employee to run the shop without our direct supervision, it was a big relief, both physically and mentally. We felt we had taken a huge step forward. Now a huge chunk of the day-to-day grunt work is off our hands, and we can concentrate on our longer-term goals and creative projects. –Jeff Vines, StL-Style

2. Find people who do what they do well and let them do that.
It’s hard to delegate, but then again, it’s easy if you pick your team properly. Not doing so can leave you overworked, and your employees will be bored. Eventually no one will be happy, including your clients. People struggle with this for many reasons, but most often I would say it’s due to either perfectionism or a lack of trust—and they really go hand-in-hand.  –Brent Feldman, Matchbox Design Group

3. Focus on what you love.
We quickly discovered that trying to manage every little aspect of our business all by ourselves was inefficient and hindering us from doing what we love the most. Now we focus on the creative direction and client relations aspects of our work, and we leave all the taxes, accounting and clerical duties to others. After tweaking our business model gradually over the course of 10 years, we feel pretty confident that we have found our equilibrium, although as with any creative startup, it’s constantly evolving. –Randy Vines, StL-Style

4. Fight the urge to just do it yourself.
That takes good discipline…and hiring the right people. For me, I have to deal with my own organizational limitations.  A person that has a hard time delegating tasks is limited to the energy that they can personally put out and to the hours of the day they are willing to work. –Jon Parker, Parker’s Table

5. Learn how to be tough, and don’t avoid difficult conversations.
If you’re going to set expectations, there need to be consequences if they are not met. And never have difficult conversations by email; always do them face-to-face if possible, by phone if necessary. –Dave Gray, The Dachis Group

6. Create boundaries, milestones, deadlines and, most importantly, a review process.
When beginning to share the work you have formerly done yourself, it is difficult because you have your own methodologies and also an accurate perception of time that things need to be accomplished in. Delegating properly relies just as much on trust as it does on providing good information…and knowing when it is appropriate to do so. –Brent Feldman

7. Be observant and proactive, and master the art of asking.
Watch what’s going on around you. Learn to anticipate problems and address them before they are problems. Also, good questions help you diagnose root causes of these problems and understand dynamics, so you can solve the issues instead of trying to fix a symptom.
–Dave Gray

Photography: Sarah Truckey

About the author

Sarah Truckey

@Technori

Truckey recently moved to Chicago from St. Louis, where she worked as a house sitter, grocer, writer, photographer, teacher and general fixer. After receiving her BA in Media Communications from Webster University, she served a short stint as a nanny in Barcelona, where she worked on her tan and her Catalan swearing. She has since taken to knitting, biking, cooking, and collecting vintage postcards. Truckey received her nickname "Trux" from a girls tennis team and hasn't been able to shake it.