5-Minute Productivity Hack: Save Time by Training Your Assistant to Make Quick Decisions   

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5-Minute Productivity Hack: How to Train Your Executive Assistant

5-Minute Productivity Hack – Train Your EA to Make Quick Decisions to Save Time, Increase Productivity, and Decrease Mental Load  

As a founder, time is your most precious – and scarce – resource. One of the best ways to protect that asset is, of course, by hiring and empowering a great team.  

At Mindmaven, we believe one of the most critical early hires you can make is an executive assistant (and then turn them into an Engagement Manager). But it’s not just about hiring a great EA; it’s about empowering them to reach their full potential. Many founders sacrifice productivity by waiting way too long to hire an assistant (if you have a team of 30 and haven’t hired an EA, it’s well past time!), and the select few who do get support often massively under-leverage that partnership and leave a lot of value on the table.  

In this article, we’ll share a simple yet powerful 5-Minute productivity hack to train your executive assistant, save yourself some precious time, and increase overall productivity.  

Making the Right Decisions, Quickly 

A brilliant executive assistant not only saves you time but also reduces your mental load by taking decisions off your plate. But more important than an executive assistant that makes quick decisions is having an EA who makes the right decisions, quickly. 

So, how do you train your assistant to make the right call? It’s simple: You train them to ask Y/N questions. Sounds like common sense? It’s a little bit more nuanced than you might think, and besides: Common sense isn’t always common practice. Allow us to illustrate with an example. 

Fundraising, Offsite Planning, and Delegation … Oh My!  

Imagine you’re in the middle of wrapping up a hectic round of fundraising while simultaneously planning your company’s first all-hands, post-Covid offsite. You’re excited, of course: You’ve spent the last two years building a largely remote team, many of whom have not yet met in person.  

With restrictions lifting, this is your opportunity to finally bring everyone together, to build a deeper sense of community, and find alignment on the company’s goals for the year. Exciting? Yes. Easy? Not exactly.  

Thankfully, you have an EA. 

To reduce your workload, you’ve asked your assistant to find local venues to host the event. After a little research, they ping you on Slack with an update. How valuable that update is depends upon how much ownership they take over the decision-making process. Let’s look at three ways this update might play out. 

We’ve tiered the examples using the following language: 

  • Typical Executive Assistant: What you might expect from any assistant you happen to be working with.
  • Powerhouse Assistant: An EA who takes a degree of ownership over the process and is willing to go above and beyond but doesn’t push the envelope as far as they could.
  • Rockstar Engagement Manager: A highly trained, proactive assistant who takes complete ownership and doesn’t pass a project back to you until they believe they’ve done all they can.  

Let’s look at an example of each. 

The Typical Executive Assistant:  

A Typical EA is going to follow your directions to the letter but often won’t stop to ask themselves what more they could do. While this can be hugely beneficial, it leaves a lot of value on the table. Here’s what their message might look like: 

Hey Anna! I did some digging into local venues. Here are some great options:  

If you want to do some additional digging, here’s a link with some top locations: https://www.austintexas.org/meeting-professionals/creative-offsite-venues/ 

On the one hand, that’s great: They saved you some time and research. On the other hand, all that really happened is you took something off your plate that your EM then put right back on. 

You know nothing about any of the links above. You have to open each one, do the research, and see if they’ll work for your needs – all detrimental to productivity.  

While some of the work has been done for you, the remaining research and mental load that come with decision-making are still squarely on your shoulders.  

The Powerhouse Executive Assistant:  

The Powerhouse Executive Assistant is a dramatic step up the typical EA. They regularly ask themselves, “How can I go above and beyond?” They look for ways to increase productivity, own their responsibilities, and take things off your plate. Here’s what their message might look like:  

Hey John! Super excited for the offsite. I did some digging into different venues. Austin has some seriously awesome options. Choosing one was tough, but I think The Retreat at Crystal Lake is going to be the way to go. Want me to book it? Happy to share 2-3 more options, if helpful.  

Already this is a step in the right direction: They did the research and owned the process enough to make a recommendation. The problem? You have no way of judging whether or not their recommendation is suitable. 

They gave no context. You simply don’t have enough information to make an informed decision. Ultimately, you’ll either need to go back to your EA with follow-up questions or do some additional research yourself.  

While still a win, there’s clear room for improvement.  

The Rockstar Engagement Manager:  

A Rockstar Engagement Manager looks for any and every opportunity to save you time and ensure that the limited time you do have is used well. They optimize their communications with you to enable you to make quick decisions and increase productivity. Here’s how that might look: 

Hey Christine! I’ll keep this brief: I did some digging into different offsite venues, and my recommendation is https://www.retreatatcrystalcreek.com/. Quick summary of why:

  • Under-budget by $2,000 
  • Vegan and vegetarian options 
  • On-site accommodations (with hotels nearby if needed) 
  • Large conference room 
  • Plenty of outdoor space 
  • Only 20-min Lyft ride from airport 

Do you want me to book it? Y/N
If no, please send feedback, and I’ll make a new recommendation.  

The Rockstar EM did a couple of things here that elevated this message from good to great: 

  • They made a clear recommendation. 
  • They provided context that enables the exec to make a decision. 
  • They phrased their recommendation as a “Y/N” question, so their exec only has to give a single-character response. 
  • They provided clear next steps if the answer was “no.” 

This is an assistant who truly understands the power of their role. They take productivity to a new level by removing the research and decision-making process from their exec’s shoulders (as well as the accompanying mental weight associated with each). 

What Can You Learn Here?  

While all examples increase productivity – saving the executive time and mental energy, the third example is the most beneficial. When you train your EA to ask the right Yes or No questions, you empower them to dig deeper and take most of the decision-making time off your plate.  

By training them to ask the right questions, you’ll be able to make quick decisions without having to ask follow-up questions. This will allow you to stay focused, efficient, and productive during your day-to-day operations. In addition, it will empower your EA and help them become more effective in their role.  

It might seem counterintuitive, but by asking your assistant to only bring you Yes or No questions, you’re actually empowering them to make more informed decisions and follow their “gut instinct.” That’s because they’ll be forced to do the research beforehand and narrow down your options to give you a clear and straightforward choice.  

That is what separates an average EA from a rockstar EA or EM (Engagement Manager).  

Watch What is an Engagement Manager (EM)? to learn why we at Mindmaven created the role we call “Engagement Manager” or EM. A hybrid between an EA and Chief of Staff, whose primary responsibility is empowering you to reach your fullest potential as a leader. 

So, how do you train your EA to ask the right questions in the right way?  

3 Pragmatic Tips on Training Your EA to Ask Yes/No Questions

1. Every Message Should End With “Y/N?”

Emphasize the importance of only sending Yes or No questions. When your executive assistant sends messages that aren’t framed in that format, hand it back to them and ask them to dig a little deeper in order to send it back in a way that allows for a quick and easy decision. 

It doesn’t need to be an involved process: Just a quick message like, “Could you please resend this as a Y/N question? Would love to hear your recommendation. Thanks!”

2. Set Specific Criteria for Each Decision

When you’re getting ready to delegate, whether big or small, take a few minutes to clearly communicate the specific criteria that must be met.  

In the third example above, the only way Christine’s EM was able to provide the context was because Christine clearly communicated what she needed in an event venue. When she handed the task off to her EM, she clearly stated the budget, dietary needs, and other important criteria.  

To empower your EM for success, make sure you do the same—and invite your EM to ask questions when they don’t understand. 

3. Feedback is King

Especially at the beginning of this process, feedback is vital. Look for any and every opportunity to give feedback. 

  • Did your EM fail to make a recommendation and phrase it in a Y/N fashion? Pass it back to them with a reminder. 
  • Did your EM make a clear Y/N recommendation, but you disagree with their decision? No problem: Treat it as a calibration opportunity. Let them know why you disagree and ask them to try again.  
  • Did your EM make a clear Y/N recommendation that you completely agree with? Great! Celebrate that. Give them feedback letting them know what specifically you appreciated about their recommendation. 

No matter how “right” or “wrong” their recommendation might be, see it as an opportunity for growth; to re-enforce helpful habits or help eliminate unhelpful habits. The more feedback you’re willing to deliver, the more valuable this tactic becomes.  

Quick productivity tip: A great way to provide fast and effective feedback is through voice dictation. Learn more about how to use voice dictation to communicate with your EM here.   

The bottom line is that by teaching your EA to ask Yes or No questions, you’re opening up a world of possibilities for both you and them. You can focus on more important things, and they can take on more responsibility. It’s a win-win for everyone involved! 

Ready to Transform Your EA Into a Rockstar EM? 

Whether you want to level up your partnership with your existing EA or finally make that hire in the first place, we’re here to help. We invite you to sign up for a free 30-minute consultation with one of our incredible coaches to learn how to recruit and build an empowered relationship with your EA. Click here to chat with a coach 

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Radical Delegation isn’t your typical business book.

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