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David’s Leadership Articles

Five Ways to Win Well with Your Assistant

by | Dec 1, 2016 | By David Dye, Winning Well |

He’s in the background responding to emails, setting appointments, or fixing your website. She’s overseeing projects, and clicking off those daily/weekly/monthly tasks that you may forget about while you focus on what YOU do best. He’s the glue that keeps things together, she’s the one who graciously gatekeeps, protecting your time and workload when she can. That’s why it’s vital for you to develop a Winning Well relationship with your assistant(s.) 

Let’s Grow Leaders/Winning Well has a team of several people who assist in the mission. My particular role is Executive Assistant / Winning Well Ambassador, which means I take care of a myriad of things for Karin (and David) including staying in communication and coordination mode with other team members. Karin invited me to write a blog post and I decided to share five of the Winning Well principles that you can apply as you interact with those “rock stars” on your team.

Blend the bottom line with the human spirit. Your assistant is not only your right hand, but also a vital, interesting person with lots to contribute! Make sure to take time to get to know them as a person and learn what energizes them. In our case, Karin and I enjoy being connected on Facebook, and having a regular Zoom meeting. She’s also willing to listen and give input into my journey as a small business owner.

Leaders don’t motivate, they cultivate. I’ve grown in my professional life since being on the LGL/WW team. We’ve seen the business expand, and the day-to-day needs change. We talk honestly about the best place I can fit and areas in which we both can grow in how we communicate, the roles we play, and more. Have regular conversations with your assistant about how they are growing and what areas of responsibility and workflow may need to be looked at again.

Nothing inspires a team more than being willing to admit a mistake. Some time ago, I made what I considered to be a pretty substantial mistake with Karin’s work. I owned up and made a commitment to making sure it didn’t happen again. Instead of hammering me about it, Karin acknowledged it but helped us quickly move on. She could tell that I already had thought through how to avoid it in the future. She also has taken responsibility when she felt responsible for an oversight.

If you’ve communicated once, you haven’t communicated. We’ve found it valuable to revisit the “why” behind why certain tasks are needed. Even recently, Karin reiterated the rationale behind a particular initiative I run with regularly. As an administrative pro, it’s easy to get caught up in the systems and workflow, and neglect to remember the big picture. A good manager will make sure their “behind-the-scenes” staff are up-to-date and on board with the organization’s mission and values.

Make the MIT (Most Important Thing) clear. Karin doesn’t play the MIT card on everything…but when she tells me that a particular task is an MIT, she explains why, and I know that is something to make sure I focus on consistently and make a priority.  

One of my daily MIT’s is to Help Overwhelmed Professionals Excel. It’s a privilege to have Karin as part of my client family and to help her have a smoother day. In fact, I recently released a free 30 minute course to help professionals Unlock the Doors to a Peaceful Work Day: Five Keys to Putting Together a Smoother Day. With her encouragement, I invite you to check it out for a few tips about how you can experience a little more peace in yours.

David Dye helps human-centered leaders resolve workplace ambiguity and chaos, so that they can drive innovation, productivity and revenue without burning out employees. He’s the President of Let’s Grow Leaders, an international leadership development and training firm known for practical tools and leadership development programs that stick. He’s the award-winning authors of four books including Courageous Cultures: How to Build Teams of Micro-Innovators, Problem Solvers, and Customer Advocates and Winning Well: A Manager’s Guide to Getting Results-Without Losing Your Soul and hosts the popular Leadership without Losing Your Soul podcast. David is a former executive and elected official. David and his wife and business partner, Karin Hurt, are committed to their philanthropic initiative, Winning Wells – building clean water wells for the people of Cambodia.


  1. Sam


    I really believe frequent communication is such an important aspect between an individual and his/her assistant. I know it can be frustrating not to know the MIT, as some people are better at communicating it than others. But like most things, time and experience will only help the assistant and boss team.

  2. zafarmanzoor

    Excellent points / list. Unique writing.
    Every point is imp,valid and practical. I appreciate.
    Zafarmanzoor, Sr. Exec, Pakistan.

  3. sysacad

    Thanks for the article , great stuff

  4. Real Estate Consultant

    Great Post . I Agree with point – Leaders don’t motivate, they cultivate.


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