How to hand off projects and step away from the office

Amy Dennis didn’t mean to start a creative agency. It just sorts of happened. After leaving a design job at a magazine, Dennis, now the owner of Nice Branding Agency in Nashville, struck out on her own as a freelancer. The work started rolling in, and in, and in. Eventually, she had more work than she could handle on her own, and her freelance life began to morph into something bigger.

“Everything has evolved very naturally,” she says of her now nearly fifteen-year-old business. “[The work] just fell in my lap, and I had to learn how to run a business.”

And learning how to run a business, anywhere from six to ten employees, hasn’t always been easy for her. As a freelancer, Dennis did everything because she had to. But as an agency owner, with employees she hired to reduce her workload, still continuing to do everything wasn’t sustainable, for her life or her business. With feelings of burnout and creative fatigue constantly nipping at her heels, Dennis had to learn how to let go and delegate.

Hire the right people.

Effective delegation requires learning to trust employees to do their jobs well and loosening the reins of control. That starts with hiring the right employees.

When Dennis was solo, she knew she would deliver on everything she promised clients because she was the one producing the work. Once she started hiring employees, rather than reducing her stress, the new employees often increased it. She found herself going back behind employees to clean up work that wasn’t up to par to avoid having a tough conversation. Or she would take on additional work because she was the only one on staff with the skillset to accomplish the task.

“My first significant hire was my director of design, and she’s been with me now for nine years,” says Dennis. “That’s been great to have a steady person who gets to know you, learns how you operate and is a great designer.”

While some of the work eased up on Dennis with the design position filled, she was still pulling most of the strategic, creative, and administrative weight. She was stressed at her job, and her husband was stressed at his. And then one day, after her husband accidentally left their young son in the car while he went to work instead of dropping him off at Dennis’s mother’s home, Dennis knew something had to give. Their family was stretched too thin and now their son was paying the price.

“That was our wake-up call. One of us had to decide that we were going to put what we were doing aside and help the other person,” she recalls. “I looked at him and said, ‘This business, if I had help with it, it’s legit. But I’m dying, and I need help.’”

Dennis’s husband left his job and came to work for the agency, taking on all the financial responsibilities and leaving Dennis with more time to devote to strategic and creative work.

Then three years ago, Dennis hired her childhood best friend to head up strategy. For Dennis, having her longtime director of design, husband, and best friend all onboard meant having three trusted people in place to help carry her business forward. She could get back to growing the business–and even found time to stop and enjoy the successes along the way.   

Get some guidance. ASAP.

After more than a decade owning her agency, a big turning point for Dennis was finding a mentor—someone with deep familiarity of her industry but plenty of distance to be objective. So, she reached out to a woman who had successfully run her own agency for more than 15 years and asked for help. Under her mentorship, Dennis was able to make some big changes that would allow her to clarify her role, increase the agency’s profits, and allow Dennis to “work on the business rather than in the business.”

“I met with her out of sheer desperation,” says Dennis. “I said to her, ‘I literally have a breakdown every six months to a year to where I’m just like I don’t know how many more of these I’m going to actually be able to overcome and get past.’ So she’s been teaching me a lot about making the business work for my life personally as opposed to me always working for the business.”

One of the primary benefits of being a small business owner is the independence and flexibility that come from being the boss, but that can also quickly turn into a liability when the responsibility of the organization and its employees rest squarely on the owner without help.

Finding a business mentor or coach, even for just a short amount of time, can help identify and reframe where your priorities should be and what might be best served by establishing a new position, delegating to an existing employee, or hiring an outside resource.

Define and implement systems.

Dennis bucks the stereotype of the disorganized, big ideas only creative and thinks of herself as more of a Type A creative.

“I’m big into the details and I can see those little things, but I can also dream big and create things,” she says.

But just because Dennis can do both didn’t mean she knew how to optimize either. With the help of her business coach, Dennis has been able to put some practical systems in place that allow the “little things” to never go overlooked and the “big ideas” to flourish.

By bringing on her best friend as director of the strategy, Dennis gained a right-hand woman to hold more of the weight of the work. She would be responsible for overseeing employees and ensuring the systems they’d put in place were operating smoothly, and Dennis would let her. The pair was clear from the outset, too, that when needed, Dennis would still hold the responsibility of the final say on challenging decisions.

It’s been important, too, for Dennis to learn precisely what her agency is best at delivering. As it became more apparent where Nice excelled, not only could she hire toward that, but she could also stop saying yes to projects that weren’t suited for the agency and were a drain on her creative and financial resources. Every time she said no to a project that wasn’t quite right for Nice or successfully delegated work away, it meant more time freed up to spend with family, to pursue her own personal interests, and to restore her creative juices.

The decisions that Dennis used to make based on intuition are now backed by definitive systems. The result has been more simplicity and a lot fewer spinning plates to manage.

Boss first, friend second.

The last bad habit Dennis had to break was picking up the slack for employees whose work just didn’t live up to the agency’s standards. Until just a couple of years ago, rather than address performance or let those individuals go, Dennis would instead double down on her efforts to make up the difference.

“I was really close to my staff and that was hard. When your friends with somebody, it’s hard to lay the hammer down when the hammer needs to be laid down,” she says. “So, I would always be taking the work on myself as opposed to making the employees perform.”      

Transforming from someone who filled in the gaps for everyone else to a true CEO wasn’t an easy process. It meant learning how to hold others accountable, to say some hard things, and to be willing to do what was in the best interest of the business so that her business didn’t eat her—or her family—alive.

As a small business owner, boss, wife, mother, designer, and friend, Dennis still wears a lot of hats. She still feels the day-to-day pressures of being a small business owner, but she’s also done the hard work of asking for help and then implementing the suggested changes. Learning how to delegate, to empower her employees to do great work, and to design processes that clean up confusion mean today Dennis can successfully hand off projects and step away from the office with peace of mind. 

For further reading, check out more from our SMB Frequently Avoided Questions (FAQ) series that gives practical, actionable advice on the questions that small business owners are too afraid to ask.

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