Delegation is a Skill

As a CEO, executive or leader, you are expected to delegate, regardless of how big or small your business is. If you do not, you will quickly notice that your business is not growing at its full potential, or not at all, because you become the bottleneck. Most people I speak with struggle with delegation. Main challenges they cite are: “No one will do it as well as me,”  or “It takes me more time and energy to train someone, so I just do it myself,” or “I can’t trust someone else with critical tasks—what if they make a huge mistake and I lose business?”

All reasonable explanations to put a pause on delegation and to tough it out on your own. Or are they? 

Do you recall the last time you were taught how to delegate? Was it on-the-job training? Was it on-your-own training?  In college? In primary school or by your parents? Or ever?

Most people have not had a formal training on delegation, so they are not comfortable with this skill. And I call it a skill because it can be learned and practiced. 

A novice at delegation is usually someone who tries it by assigning small tasks of low value, so they don’t care if it is done 100 percent to their specification as long as it is done. Most of the time these experiences go “well” because there is nothing to lose. As you become a more experienced delegator, you start delegating higher-value tasks, in which outcomes are more critical and can affect your career, life or livelihood. Where do you fall on: novice, learning or  experienced? Rate yourself from zero to 10 and be honest. 

At all levels of delegation in your business and personal life, there are factors that should be taken into consideration before outsourcing any tasks and there are some tools to help ensure appropriate outcomes.  


Do you trust the person you are delegating to? Would you trust them with your wallet, with your life, with your child’s life? Your willingness to delegate will be limited by your trust level. If you view someone as capable, well-meaning, eager to learn or already having more expertise in the subject matter than you, you are more likely to rely on them to produce results and sleep better at night. If you question their skill level or motivation, you are less likely to invest your valuable time training them or will be worried the whole time that they will fail, and it will reflect poorly on you or your business. Start by delegating a small task to test the individual and to understand your own confidence level. This way the mistakes will be manageable, and they will enable all parties to understand what can be done better or what part of the process should be adjusted. As you train them in your style and collaborate on the process, with consistently successful outcomes, you will build the trust in the individual and in your own delegation skills.  

Clear communication:

People cannot read your mind and they don’t know what you will like or how you will do it unless you show them and explain. Confirm that they understand what you are asking them to do, allow for the questions and be patient. If you rush or are distracted by calls and emails while trying to explain what you want, something will be amiss and you will not be happy with the outcomes. If you do not hone in on this skill, delegations will always be a challenge for you because you will be the “problem” that needs to be fixed in that equation.

Take your time to walk through the whole flow of the task so there is a contextual understanding of how the piece you are delegating fits into the whole workflow. This simple step eliminates confusion and it builds a relationship of trust and respect between the two or multiple collaborating parties. And you might be pleasantly surprised—with a fresh set of eyes, a new, more efficient process or product might become evident. 


Many leaders boast an A-type personality with a strong dose of perfectionism. That translates to strict rules on how things are done, sometimes at the expense of the outcomes. Delegation means changing your routines as well as responsibilities. Instead of functioning as an operator responsible for all aspects of sales, marketing, finance and management, as a leader and CEO, your role is to build a team of people around you who will take on firefighting for you, so that you have a strategic vantage point and can steer the direction of your ship. The larger your business becomes, more of your time will be required at the strategic, big-picture level. Keeping focused on the outcomes and overall plan you are working toward—a more-efficient and growing business—is the key, and delegation helps you achieve that.

The ultimate benefit of delegation is leveraging your time and productivity. Most successful people in the world, icons and industry leaders, have to be experts at delegation. Microsoft’s market cap was $257 billion on the day Bill Gates stepped down. He would not have been able to build a company of that size by himself. Trust, clear communication and welcoming change, enabled Gates to build a competitive business and secure a successful succession. Most successful delegators apply these principles in business and in their personal life to create space that enables them to intentionally build their legacy. 

Vera Anderson is a legacy coach who focuses on sustainable growth for her clients. An entrepreneur and mentor with a private-equity background and global resources, she provides customized guidance to fund managers, C-level executives and family office principals striving to reach their full potential in business and in life and helping them create an intentional legacy. Contact her at 312.206.1060,, or visit

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