How to Master the Art of Delegating to Your Assistant

How to Master the Art of Delegating to Your Assistant

There is more to do to grow your business than you can manage alone—so what is holding you back from delegating more? Here are 5 mindsets and actions to adopt that will help you master the art of delegation, based on tips and advice from C-suite executives and leaders.

1. Learn to let go. 

Richard Branson Quote

"If you really want to grow as an entrepreneur, you've got to learn to delegate."—Richard Branson, CEO and founder of Virgin Group

A common barrier to delegating is the belief that no one can do it better than you. This mindset clouds your outlook, causing you to believe that since you can do it all—you should do it all. 

Yet, even if you are superhumanly skilled in all areas of your work and life, thinking in terms of profitable actions can help you let go of the work tasks you know are low stakes, which are keeping you from doing the work that will give you a higher return on your time investment. 

2. Test for reliability. 

TIm Ferriss Quote

"I test reliability before I test the skill set."—Tim Ferriss, author of The 4-Hour Workweek, in a podcast interview on the art of delegation 

Another barrier in delegating to others is a matter of trust. Trust is an essential component in creating an effective working relationship with your virtual assistant. When you fully trust another person, you are willing to let them shoulder your load. If you don't trust the VA you outsource to, then you'll be worried and anxious over the tasks you have assigned—negating the benefits of delegation.

Testing for reliability is a quick way to rate a VA's trustworthiness. Ask yourself: Do they reply within the agreed-upon timeframe? Have they kept their word on delivery? If the answer to these questions is yes, you've found an assistant you can trust. 

3. Don't micromanage. 

Jared Hecht Quote

"Explain what needs to get accomplished, and then let them figure out how to get it done. You hired those people to bring great ideas to the table, not to follow your every micromanaging instruction."—Jared Hecht, Co-founder and CEO of Fundera 

If you are micromanaging, you are not harnessing the benefits of outsourcing your to-do list. 

Naturally, you want to ensure that the task is being done competently. But the more you can shift your thinking from micromanaging tasks to creating a system that allows you to focus on bigger picture goals, the more you will get out of those you employ. 

4. Create your rules. 

Chris Ducker Quote

"Start outsourcing all the simple tasks that are bogging down your workload and stunting your productivity every day."—Chris Ducker, CEO and Founder of Youpreneur.com

To find out what areas you could be outsourcing to your virtual assistant, try this exercise by Chris Ducker, called “The 3 Lists to Freedom.” As you write out these lists, you will uncover many tasks that you should be outsourcing.

  • Write a list of things you hate doing.

  • Write a list of things you are unable to do yourself.

  • Write a list of things you are not supposed to be doing.

5. Clarify your goals. 

George S. Patton Quote

"Don't tell people how to do things, tell them what to do and let them surprise you with their results."—George S. Patton, high-ranking WWII US Army General

Clarifying what you want is not the same as micro-managing. Clarifying a project at the onset is about setting a clear expectation of an end goal. Define what the finished product should look like and what you hope to accomplish at the very end of the project. 

For example, when outsourcing a research task, don't just ask for stats for XYZ. Describe what the research project is for—the end goal of the completed research. This will allow for creative thinking that could add beneficial components that you might not have considered or known to ask for.  

6. Assess as needed.

Denise Morrison Quote

"Balance suggests a perfect equilibrium. There is no such thing. That is a false expectation... There are going to be priorities and dimensions of your life; how you integrate them is how you find true happiness."—Denise Morrison, CEO of Campbell Soup

Automating and delegating weekly and monthly tasks will free up space in your mind. However, reassess every so often to be sure you are making the most of your VA. Your needs will likely change depending on the season and on personal and work-life conditions. And your virtual assistant—no matter how fantastic, reliable, and skilled—will not be able to read your mind. 

The only way for your assistant to provide the kind of timely help you need at crucial moments is through communicating changes in circumstances and new needs as they arise. 

Finally, here's Reid Hoffman, co-founder of LinkedIn, on the importance of not going it alone:

Reid Hoffman Quote

"No matter how brilliant your mind or strategy, if you're playing a solo game, you'll always lose out to a team."


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