Mastering Delegation: How High-Performing Executives Can Maximize Their Executive Assistant’s Potential

As a high-performing entrepreneur or executive, you know that scaling your business means mastering the art of delegation. Yet, this essential skill often eludes even the most seasoned leaders. Delegating effectively is more than just handing off tasks—it’s a strategic process that, when done right, unlocks your executive assistant’s full potential and frees you to focus on high-impact decisions.

My journey with delegation began when I launched ChatterBoss in 2017. Having spent years as an executive assistant to influential leaders, I thought I had delegation down. I had been on the receiving end of it for years, so I believed it would come naturally when the roles were reversed.

The Reality Check

I quickly learned that being a great delegator is not innate, even for someone who’s been on the receiving end of tasks. It’s a skill set that requires intentional development. Through a lot of trial and error, I identified the key elements that helped me delegate efficiently and scale my business.

If you’re an entrepreneur or executive looking to join the top 1% of high performers, these strategies will help you unlock your assistant’s potential and reclaim your time for what truly matters.

1. Over-Communicate When Assigning Tasks

Early in my journey, I realized that assumptions are the enemy of successful delegation. While it’s tempting to believe that your assistant will "just get it," the reality is that clear communication is essential. As high-level executives, the complexity of our tasks often requires far more detail than we think.

Executive-Level Challenge:

You may be juggling multiple departments, initiatives, and stakeholders. This complexity makes over-communication even more crucial. What’s obvious to you might not be clear to your assistant unless you’ve spelled it out.

Actionable Tip:

When assigning tasks, outline the objective, the expected results, and the resources needed. Ask for a summary to confirm understanding and create an open channel for questions. In doing so, you eliminate ambiguity and reduce the chance of miscommunication.

2. Focus on Outcomes, Not Processes

As executives, we often have specific ways we like things done. However, focusing on how tasks are accomplished instead of the desired result can limit your assistant's creativity and potential. A critical shift in my approach was learning to emphasize the end goal and give my assistant the autonomy to figure out the path.

Executive-Level Challenge:

Micromanagement is a significant drain on both your time and mental energy. High-level entrepreneurs are pulled in multiple directions and can’t afford to be stuck in the weeds. By focusing on outcomes, you free up your time to focus on strategic decisions.

Actionable Tip:

When delegating, clearly define the outcome you expect, but allow flexibility in how it’s achieved. For example, if you need a presentation by the end of the week, focus on the result—an engaging, data-driven deck—rather than specifying how each slide should look. This not only empowers your assistant but also helps you step out of the minutiae.

3. Audit Your Instructions for Clarity and Feasibility

Before delegating any task, I now make it a point to audit my instructions. Are they clear enough? Are they broken down into manageable steps? Is success measurable? This simple habit has dramatically improved the results I get from my assistant.

Executive-Level Challenge:

Executives often operate with an urgency that doesn’t leave much room for detailed instructions. This can lead to inefficiencies, as tasks are left too vague or overwhelming for the assistant to manage.

Actionable Tip:

Before you delegate a task, ask yourself if the instructions are concise, measurable, and manageable. For example, instead of asking for “a report on sales trends,” specify “a report that highlights sales trends over the last 6 months, broken down by region, with visual aids.” This makes it easier for your assistant to meet expectations, and it ensures you get the data you need without back-and-forth.

4. Take Responsibility for the Entrepreneur/Assistant Relationship

The success of delegation depends as much on you as it does on your assistant. One of the most important lessons I learned is that delegation is a two-way street. If something goes wrong, instead of blaming my assistant, I’ve learned to first look at my own role—whether my instructions were unclear, or whether I failed to provide the necessary support.

Executive-Level Challenge:

High-performing executives are often stretched thin, which can make relationship-building with your assistant difficult. Yet, without strong communication and mutual understanding, the assistant-executive dynamic falls apart.

Actionable Tip:

After completing major tasks or projects, conduct a debrief. Ask your assistant for feedback—what worked, what didn’t, and what you can do to improve your delegation. This not only strengthens your relationship but also helps you continuously refine your own leadership style.

Delegation for High Performers

To underscore the importance of delegation, consider this: According to a study by the Harvard Business Review, executives who effectively delegate see a 33% increase in overall team productivity. Another report from Gallup found that CEOs who delegate well generate 20% more revenue than those who don’t. These numbers demonstrate the immense value of mastering this skill.

In fact, The Expert Journal of Business and Management noted that leaders who effectively delegate feel 22% less stressed, leading to better decision-making and overall well-being.

Delegation is a Continuous Learning Process

Mastering delegation is an ongoing process that requires time and intentionality. However, by over-communicating, focusing on outcomes, auditing your instructions, and fostering a strong relationship with your assistant, you’ll be well on your way to optimizing your time and scaling your business.

Don’t fall into the trap of thinking that delegation is only about handing off tasks. It’s about empowering your assistant to take ownership and become an extension of your leadership.

Ready to take your delegation skills to the next level? Download our Executive Delegation Checklist to ensure you’re set up for success with every task you assign.

‍