Visionary entrepreneur sitting with business operator.

How To Set Your Operator up for Success as a Visionary Entrepreneur (And Avoid Sabotage)

“I recently hired an executive assistant, and things were going great… until they weren’t.” 


Can you relate to this statement? 

It’s one we’ve heard from many of the Visionary Entrepreneurs that we help when they hire someone to help them in the business. 

Typically this person was hired as an executive assistant, virtual assistant, or personal assistant to start (you will hear us refer to this person as an Operator). 

For the first couple of weeks or months, everything was great. The Visionary entrepreneur felt less pressure in the business, had more time, and thought they had finally found the help they needed. 

Then, seemingly out of nowhere, things started to change. 

Suddenly, the Operator was no longer stepping up and taking initiative. They started missing things, and the company was affected by it. The visionary entrepreneur started to lose confidence in their Operator and has even been considering letting them go. 

When our clients share these frustrations with us, we share a difficult truth with them. When this happens, the entrepreneur is probably sabotaging their Operator.

It’s never intentional, and most of the time, they don’t even realize they are doing it. 

To understand what we mean when we say sabotaging the Operator, you first need to understand the Operator Personality Type.

What is the Operator Personality Type

Executive Assistants, Business Operations Managers, Integrators, or as we refer to them, Operators, are the people who love process, structure, and routine. The Operator Personality Type, as we refer to this archetype, is vital to helping balance a visionary in a business because they are good at the tasks and responsibilities CEOs usually don’t love, like calendars, checklists, and processes.

The Operator Personality Type wants to make sure projects get set up correctly, executed on time, and the business moves forward. Autonomy is one of the most important things an Operator wants and needs to accomplish in this role. 

Being able to get things done on their own. Get help when they need it and get input when they ask for it. 

In addition to the autonomy to get things done, an Operator Personality Type also:

  • Loves details and always wants to know the how and the why
  • Is always prepared and plans ahead 
  • Is Data-driven and makes decisions based on evidence
  • Seeks efficiency and making things more efficient 
  • Wants to build process that makes it easier to get things done
  • Creates consistency and stability in the environments that they are in

When an Operator is unable to do any of the above, they start to feel anxious, lose confidence, and may even underperform. 

Understanding the Operator Personality type helps put into perspective some of the things that Visionary Entrepreneurs do that can unintentionally sabotage their Operator.

How a Visionary can Sabotage their Operator (By Accident)

What happens in the relationship of many Visionary Entrepreneurs and Operators is that things start well in the beginning. The Entrepreneur gives the Operator space and autonomy, and control over what they’re doing. The Operator is performing well, and the entrepreneur is getting the help they need. 

Then without meaning to, many Visionaries start sabotaging their Operator and don’t even realize it. While the Entrepreneur thinks they’re helping their Operator, they’re reducing their ability to be effective. 

Visionary Stepping in Too Much

Remember, Operators, love autonomy. They love being able to create processes, make things better, and solve problems. 

Issues come up when the Visionary starts to step in too much. They start to tell the Operator how to do things. Instead of focusing on the outcome, the Visionary focuses on how the Operator is doing their job, the steps they’re taking, and what they don’t like about it.

And then they start solving for the Operator. We share with our members that “solving is not serving.” When an entrepreneur gets too focused on how something is being done, then tells someone exactly how to do it, we call this solving. Instead, asking questions about how something is being done, coaching and supporting when necessary, and focusing on the outcome is far more productive.

Visionary Overcorrects

When Visionaries become uncomfortable with something the Operator is doing, they tell their Operator what to do and how to do it. Which results in taking decision-making away and removing ownership for the Operator. 

This challenges the Operator because they are carrying around process, structure, and routine in their head, and when a Visionary comes in and starts telling the Operator how they want things done and overcorrecting everything, the Operator is doing, they unintentionally break these processes.

What is the Result?

What happens when the Visionary starts stepping in and changing something? And when do they start overcorrecting? 

The Visionary stepping in and demanding something be done a certain way, challenges the Operator’s ability. 

The more often this happens, the more difficult it is for the operator to get their job done and move the business forward. Without meaning to, the Visionary Entrepreneur reduces the Operator’s effectiveness and efficiency. And ultimately disabling the ability of the Operator to help the Visionary. 

The Operator gets nervous, becomes anxious, loses confidence, and feels micromanaged. An operator who feels this way becomes less effective or completely ineffective in their role.

They stop showing up in the same way they did before. Without meaning to, the Visionary has sabotaged their Operator. 

So how can the Visionary entrepreneur avoid sabotaging their Operator and set them up for success? 

Visionary Leadership = A Successful Operator

Instead of solving for your Operator, coach your operator. Have discussions with them about the projects you’re working on and the outcomes you’d like to see for those projects and get their input. Discuss where you want the company to go and how you envision getting there with their help.  

When the Visionary makes decisions for their operator, not only are they sabotaging the Operator’s abilities, but they’re taking ownership over that decision. 

And if you take away the decision-making, you can’t hold your team responsible for the outcome because you now own it. 

If you are a Visionary, instead of stepping in and inadvertently taking ownership, ask your Operator, “How do you think we should do this?” 

Understand your Operator’s desire for autonomy, and instead of focusing on the steps that your Operator is taking, focus on the outcome they are achieving. 

Don’t solve for them. Ask questions, have discussions, and provide them support on the issue that has come up and help them solve it.  

Don’t tell them what to do. Coach and support your Operator and help them discover what to do. 

Don’t take over their processes. Have them explain their processes to you, discuss them together, and help them come up with the solution. 

The more you give the Operator control over the solution, coach them, and discuss with them- without solving and taking ownership – the more successful your Operator will be. 

We hope this post helped! If you have any questions or would like to learn more about how we can help you and your Operator, let us know in the comments!

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4 Comments

  1. This was the input I needed. I see how I have gotten in the way of my operators success. Coaching and support rather than taking over will be so much better for everyone … thank you

  2. TY SO Team! I love it when I learn something. I’m on the verge of hiring my first helper, and this is great information. After reading your description, I recognize myself as an OPERATOR type personality…which could be challenging when hiring other operators to help me as the visionary. I’ll have to coach myself to stay outa-da-way!

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