The art of delegating: 4 ways CEOs can empower their teams

As the 19th President of the United States, Rutherford B. Hayes received a gift from Queen Victoria that is today one of the most famous pieces of furniture in the White House. The Resolute desk, built from oak pieces of the British ship H.M.S. Resolute, was given to Hayes in 1880 and has since served as the workspace for all but 3 U.S. presidents.

When Ronald Reagan was in office, he famously adorned the desk with a plaque that read, “There is no limit to what a man can do or where he can go if he doesn’t mind who gets the credit.”

In a 1986 interview with Fortune, President Reagan explained the significance of that message and how it reinforced his leadership style.

“I believe that you surround yourself with the best people you can find, and you delegate authority,” he said during the interview. “You don’t interfere as long as the responsibility and the overall policy that you decided upon is carried out. You don’t stick your nose in there and tell them how to dot the i’s.”

President Reagan’s perspective is valuable advice for small and midsize business CEOs. Delegating is a critical skill for leaders. When CEOs can take tasks they previously performed and assign them to a different member of the organization, they have more time to focus on the company’s big-picture challenges and opportunities.

“It frees them up to work on more important strategic priorities that will have a much greater impact on revenue and net profit growth,” says Bob Dabic, a Vistage Master and Best Practice Chair based in Newport Beach.

When done correctly, delegating has an impact beyond the CEO’s office, says Eileen Coombes, community and education lead for Delegate Solutions in Philadelphia.

“When small businesses and leaders can delegate effectively, they’re going to see things get done faster and more efficiently,” Coombes says. “It’s going to be a cost savings to the company, and it’s going to retain really great talent because rising leaders are excited and hungry to take those opportunities and learn and grow.”

What does effective delegating involve?

Coombes routinely works with “solopreneurs” and small business owners to help them understand why delegation is important and how to do it effectively. She sees that most small businesses are short on staff and resources, often leading to CEOs taking on additional responsibilities that prevent them from focusing on larger business needs.

Her job is to help those CEOs recognize how receiving support from internal or external outlets can be transformational for themselves and their business.

“Leaders are able to let go of the work that holds them back and slows them down and doesn’t allow them to focus on the vision and where they see the company going,” she says. “Being able to delegate effectively allows these leaders to put themselves back in that visionary seat and embrace what the future looks like for their company versus getting stuck in the weeds and mundane tasks.”

Delegating is not about assigning tasks, though. Assigning tasks is akin to President Reagan’s reference to telling people how to dot their “i’s.” Delegation is about bestowing ongoing responsibility to someone else.

“Delegating is turning over the authority for someone to take on routine work on an ongoing basis,” Dabic says. “Assigning tasks is asking people to typically do one-off items.”

Why delegating is critical for success

Delegation offers several benefits beyond allowing CEOs to concentrate on their company’s vision. One of the most significant — and often overlooked — advantages is that it can enhance team morale and productivity. By delegating responsibilities, CEOs can alleviate their workload while enabling team members to utilize their strengths and develop new skills.

“It empowers others to take on more responsibility,” Dabic says, “which demonstrates trust and provides the opportunity for professional development and possibly more compensation.”

Coombes thinks many CEOs overlook professional development, particularly when it comes to delegating. However, doing so can empower emerging leaders to grow and develop in different functional areas of the business.

That empowerment, in turn, makes the emerging leaders feel more valued and can lead to a longer tenure with the company.

“Delegation becomes a retention strategy when leaders look at it as a way to develop their talent,” she says. “I think people stay longer and feel more valued and more committed to the end results for the company as that progresses.”

Coombes spent years working with a professional speaker who began as a solopreneur. The client wanted to expand her business but recognized there was only so much she could do independently.

To help meet her goals, she began to delegate. She brought in a few fractional support resources that handled most of her client experience process, plus her social media marketing. That offloading of work allowed her to refine her vision for her company, which she then shared with her fractional support. Within one year of delegating those tasks, the solopreneur brought in more than $1 million in revenue.

In addition to saving time for business development, delegating also offers long-term benefits, according to Dabic.

“If the business owner can make themselves dispensable via continuously delegating, they can create a ‘self-managed’ company where almost all day-to-day decisions are made by others,” Dabic says. “Then, should the company be sold, it will typically garner a greater EBITDA (earnings before interest, taxes, depreciation, and amortization) multiple since there’s much less risk for the buyer because the business is not reliant on one key person.”

4 key steps for effective delegating

Effective delegating is important, but how do you apply this to your organization? Here are 4 key steps.

1. Identifying tasks that can be delegated

When it comes to identifying what to delegate, Dabic visualizes a “decision tree” whose roots represent the decisions a CEO makes.

• The trunk symbolizes decisions that the senior managers make but that are discussed with the CEO for approval prior to implementation.
• The branches represent decisions that the CEO’s team can make independently. Afterward, the senior manager is to communicate the decisions that were made to allow the CEO an opportunity to provide developmental coaching if the decisions were not optimal.
• The leaves represent everyday decisions the team can handle without needing to report back. This structure streamlines operations and fosters initiative and accountability within the team.

The more distant the decisions are from the roots, the more the CEO can concentrate on the company’s vision.

2. Selecting the right team members for each task

Both Dabic and Coombes agree that identifying who to delegate responsibility to comes down to multiple factors. Is the person trustworthy and able to take on the task? Are they interested in providing that support? They could be the most competent employee in the organization, but if they aren’t looking for growth opportunities or to offer that relief, the delegation process won’t work.

3. Setting clear goals and expectations

Coombes says any role or responsibility being delegated needs to be goal-oriented. If the job is not helping achieve some organizational goal, it likely won’t get done. Instead, it will quickly drop down the employee’s priority list in favor of something more important. That is why it is imperative to attach goals to the delegated tasks and clearly articulate that goal so everyone understands its importance and impact.

4. Providing resources and support

It may sound obvious, but if a responsibility is delegated to an employee, make sure that the employee has access to all the necessary software and technology. Few things are more frustrating than feeling autonomous when dealing with an important business task, and you have to turn around and ask for technical assistance just to get started. It is also essential to have weekly status updates for the CEO and the delegated employee. The updates can be as short as 15 minutes to ensure things are on track, find out what’s working, and understand what challenges need addressing.

Common challenges with delegating

One of the common challenges CEOs face when delegating is dealing with the fear of losing control. While it’s a natural feeling, it can sabotage the effectiveness of delegation.

It’s also a feeling that Coombes understands personally.

“I personally am the kind of leader who wants to micromanage the heck out of everything,” she says. “With my team, they’ve learned that once a week, they need to send a status update of the projects they’re working on, and I’m very clear with them what I want to know about those particular projects so that I’m getting the information back that I need to be able to let go and trust them. Over time, those status updates allow me to build that trust with team members so I can let go quicker.”

Managing the balance between oversight and autonomy takes time. Shifting away from too much oversight becomes easier when CEOs establish clear goals and objectives early.

Best practices for successful delegating

Coombes and Dabic agree that clear and effective communication is critical for successful delegation. This communication involves identifying goals and key metrics, scheduling weekly status updates, and both parties being open to discussing ways to improve processes.

“For a lot of leaders, trying to stop in the middle of their day to talk about what’s working and what’s not can feel taxing with everything else on their plate,” Coombes says. “But just a couple minutes here and there to make sure everyone’s aligned can go a long way in ensuring that those delegations are successful and that everyone is learning and growing as a result of them.”

The communication has to be reciprocal as well. If the CEO is the only one identifying what’s working and what’s not, then the process is broken. The person delegated the responsibility needs to have the space and ability to share their perspectives, including what they might need from the CEO to improve the process.

That communication should also include addressing when delegation works — and when it doesn’t — and the lessons learned from each experience.

3 tips for CEOs to improve their delegating skills

Here are a few more tips for CEOs looking to improve their delegating skills.

1. Self-assessment techniques to identify areas for improvement

There are countless self-assessment techniques for CEOs to identify their strengths and weaknesses as leaders. For Coombes, she often recommends CEOs carve out a few minutes each day for simple reflection, including considering how their delegation is working. Whether someone is a first-time delegator or has delegated for decades, it’s important to consider what feels good about the delegation and what could be improved.

2. Seeking mentorship and learning from other leaders

Like so much about leadership, mentorship can be a crucial way to learn how to delegate responsibilities better and grow from the process. When looking for mentors in this capacity, it’s important to identify other leaders who excel at delegating and identify what allows them to maximize their time to focus on larger organizational goals.

3. Implementing feedback loops to refine delegation practices

Coombes believes implementing feedback loops is a critical component of effective communication and a vital part of the delegation process.

“Delegation is not a singular experience,” she says. “Every time a team is casting along a delegation from one person to another, there has to be a constant feedback loop happening.” The feedback loop should address what is working, what is not, and what can be learned from the experience.

Mastering delegating is a key component of being a skilled leader, particularly as a small business CEO. The idea of giving up control can be daunting, but the result of letting go can be transformational.

As President Reagan reminded himself daily, with a strong team working toward the same goal, there is no limit to what anyone can accomplish.

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