Vickie Sokol Evans interviews Executive Productivity Consultant, Jennifer Wilmoth

This is my 20th year teaching Microsoft Office classes and one of the most frequently asked questions I receive from an audience of assistants is how to best use Microsoft Outlook to manage their own priorities side by side with their manager’s priorities. It’s such a hot topic and an important one.

I can teach you all the cool tips & tricks and bells and whistles that Outlook has to offer and there are many amazing experts who can help you get out of email overwhelm and get your inbox to zero, but none of these tactics – not even my own! – really teach you the methodology and the behavior change needed to truly use Microsoft Outlook as a time management tool for yourself AND your manager. Until now.

Today, I’m bringing the experts straight to you. Sally McGhee, author of “Take Back Your Life: Using Microsoft Outlook to get organized and stay organized,” and her team at McGhee Productivity Solutions (MPS) work with individuals, teams and organizations to increase their productivity and work-life balance by creating sustainable cultures of alignment, focus, integrity, and accountability. This is what I imagine for the partnership you have with your manager and why I’ve been a fan of their work.

So, I sat down with MPS Executive Consultant, Jennifer Wilmoth to understand how assistants get started today using Microsoft Outlook to support the Assistant/Manager partnership.

Vickie: Jennifer, I’ve been a fan of Take Back Your Life (TBYL) for over ten years now. I’m so thrilled to hear that you are now offering TBYL for Assistants. What makes this programming different than the other TBYL programs you offer?

Jennifer: Having started my career at MPS as Sally McGhee’s Executive Assistant, I quickly realized that most of what we taught in Take Back Your Life (TBYL) applied to me. However, being in a reactive role, dealing with multiple stakeholders, managing high-level projects and tactical decisions, balancing what I needed to do versus keeping Sally on track with her action items all while keeping her calendar up to date – required some adaptation.  It was interesting to be an assistant in a productivity company, working alongside the CEO because we didn’t approach my role in a traditional way – but examined (very, very closely I might add!) how we could create and foster a partnership that gave us both permission for me to manage her.  We went on to share the many best practices with other Executives and their Assistants helping them too forge a powerful partnership based in alignment, focus, integrity and accountability.

Vickie: You mention powerful partnership. What does that mean?

Jennifer: Over the years, when I ask assistants “Do you have a powerful partnership with your manager?” most answer with: “yes, we have a great relationship”. And I believe it; assistants wouldn’t be where they are, doing what they do, if they didn’t have a good relationship with the person they support. But… that wasn’t my question.

So, let’s first create a distinction between “relationship” and “partnership”. One online definition of relationship is “a state of connectedness between people.” Having a good fit with the person you’re supporting is desirable and can impact your success.

However, when we look at an online definition of partnership “a relationship … usually involving close cooperation between parties having specified and joint rights and responsibilities” it goes beyond working well together and includes collaborating on shared objectives, having each other’s backs, and trusting we’re both doing our best to ensure the others’ success.

Vickie: What are some ways for assistants to shift their relationship into a partnership and how can technology like Microsoft Outlook make a difference?

Jennifer: Let’s distinguish the “what” from the “how”.  So many of us understand – in theory – good ideas of what we can do to create partnership.  My suggestion is once you identify a strategy for developing a new approach, look at how you can leverage Outlook to adopt that new approach.  For example:


Ask your Manager what their goals are:

Imagine knowing what she/he/they are working towards accomplishing on an annual, quarterly, monthly and weekly basis; you’re aligned to their vision.


Track these goals in a task in Outlook and treat them as your objectives too!  Capturing these in Outlook can keep them in sight and top of mind.


Manage their calendar to their goals

Now that you’re clear on where they’re headed, you can ensure they’re focusing on the important things first. Since they likely have more to do than they can do, and are saying “yes” far too often, it’s up to you to schedule the right meetings on the calendar and renegotiate the others.


Many assistants have shared a best practice of creating a color to represent each of their Managers’ goals.  Then they can color-code their Managers’ calendar by objective – this not only helps the Manager see where they are and are not focusing their time, but also helps you ensure you know what they’re doing and which objective it supports.


Schedule – and keep – your 1:1 meetings

In order to keep up to date on the ever-changing priorities you’ll need to talk with your Manager regularly. The 1:1 doesn’t have to be in person, but if you schedule over it – reschedule it. You are in charge of their time so your meeting with them is as important – if not more so – than any other person they need to meet with.


I know you cannot control them attending, but hey, you’re in charge of their calendar so make sure that appointment is on there.  And don’t give it away!


Make recommendations

Come to your manager with suggested solutions for problems. When you make recommendations, you’ll get input on where you’re on track (they may even think you’re a mind reader) and if you are off track you will likely get information you did not have before. It’s a win-win.


Create a category in Outlook (I had a 1:1 Sally for example) to track the things you want to discuss with your manager. You can attach emails, notes and/or documents into that task to support the recommendation you’re making.


Be powerful

Make those tough decisions. You will learn one of two things: it wasn’t what they wanted or it was just the solution they were looking for. Neither is right nor wrong; they’re both feedback on what did or didn’t work for that situation.


Be your courageous and confident Self.  You don’t need Outlook – YOU got this one!

If you focus on these five steps and use the tools to support your implementation, it will move you toward creating a powerful partnership where you are aligning on the desired results, focusing resources to achieve the results, having integrity and being accountable for ensuring your manager achieves their goals. That is definitely a demonstration of two people collaborating with distinctive roles to achieve a common goal – or being in a powerful partnership.

Have fun transforming your relationships into partnerships.

Vickie: This is such a great start. And I know there is much more to explore. I’d love to continue the conversation in part 2 of this series. What can we expect as next steps?

Jennifer: In order to foster that powerful partnership, it is helpful to be mindful of what you can control, what you cannot control, and where to wield your sword of influence. Having this awareness can help you decide where to invest your energy and where to simply let “it” go.  In the next article, I’d love to share some ideas how to do this! Because in my opinion most assistants underestimate their ability to influence.  After all, they are the key to the kingdom!

Literally making the audiences’ jaws drop, Vickie Sokol Evans, author of the bestselling “100 Tips” series for both PC & Mac, teaches the world’s smartest people how to use their technology better. She's witty, sharp, pointed and knows more about how ... (Read More)

Leave a Reply

Your email address will not be published. Required fields are marked *