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Strategies for Optimizing 1:1 Meetings (Free Guide)

Executive Assistant and Executive Check-in

One:One meetings, or as we prefer to call them [Executive Check-in], are the lifeline to being very successful in your role. In connecting with several thousand admins since 2017, it's evident that many of you share the same frustration: not having sufficient time for your meetings, having meetings rescheduled, or even meetings that don't take place at all.With this article, my aim is to inspire you to:

  1. Persist and not give up,

  2. Reevaluate your approach, and

  3. Embrace strategies to enhance your influence and agency. Additionally, the insights shared here can contribute to rebuilding trust with your executives and colleagues.

Mindset and Strategy

It’s important to bring up, we are all human. Grace regarding your human-ness is recognizing empathy goes a long way. Your goal is to have a 360 degree view of your executive(s) and what’s happening in their world. For established relationships you are blessed to know a significant amount of information about your executive: the noise that comes at them, the demands that cross their desk, and if you have a close relationship, you know personal components. You know and understanding they have decision fatigue on a daily basis. And for new relationships, you are in your role because of that decision fatigue, both noise and strategic related. When meetings are lackluster, pushed off, or not happening, it’s important you remember it’s not (all) about you….or is it? Executives often tell me, I don’t keep those meetings with my assistant, because I don’t feel like they are productive. I leave with more burden than relief. Read that last sentence again.

So I ask, is your strategy collectively about both parties or only about your punch list? This is where you move from tactical to strategic. Let me explain.

Purpose of the Executive Check-in

The purpose with the check-in is to align thinking so you and things can proceed forward. Another purpose for the check-in is to give the executive rich updates (in a concise manner) about everything going on, so they know things are moving forward due to your involvement (i.e., impact). Lastly, another purpose for thecheck-in is to receive agency so you can make (more) executive decisions as each week passes.

Let’s focus on a few reasons why you may not be getting time and also some ways to approach your Executive Check-in so both of you leave better off vs. fatigued more. 

Day of your Check-in Matters

My conversations continue to divulge that Monday mornings are the designated day for 1:1 meetings. Since starting Exceptional Admins in 2017, and having talked to over 6k professionals, I can say with a lot of confidence that if you meetings are designated for Monday’s this is a contributing factor of why there are issues. I highly considering Thursday as the designated day (advice coming below).

As an aside, I’ve heard from a small group of professionals they are blessed with a 9:00 AM on Monday and they happen routinely; sadly, this is not the norm.

In wanting to change the narrative, I’ve advised to many (and asked they report back) that they move their meeting to Thursday instead. I’m excited to report they’ve had more success with this day and also report a sense of accomplishment after their Executive Check-in concludes. One of the great things with a Thursday meeting is some of the items on your list organically get resolved leading up to Thursday. This day also offers enough time (crossing fingers) to get work done by EOD Friday so you don’t have to worry about it all weekend. Which I know, as I type that sentence, some of you might be laughing at me. Yes, I know, many of you are always on the clock. #wink

Deploy

During my calls, when we’re talking about the pain points of their current partnership, I’ve learned some are not thoughtful of the executive’s time or energy. Executive assistants often find themselves aiming to swiftly tackle their to-do lists during 1:1 meetings with their executives, driven by the pressing constraints of time. Regrettably, when I ask they share their approach to these meetings, a staggering 80% lack a coherent strategy/explanation. This lack of strategic planning can hinder the effectiveness and flow of these crucial check-ins.They have their list and materials, but lean on the executive to dictate the flow. Now, some relationships work well this way, and others are hurting because the executive wants a different style (hence the reason for avoiding the meetings, they don’t want to have to explain what they want). In all my work about personal branding, I know this oversight is hurting the assistant’s brand resulting in lackluster meetings and low engagement. From the executive side of my work, time and time again executive’s highlight they need to experience meeting-composure to trust their assistant has their time and energy at a top priority in these meetings. This helps them see their assistant as a strategic business partner. Having a high level of preparedness will help you earn time on the calendar (and keep it), plus agency:

  1. Being very concise is super, duper important! Executives read in bullet fashion not paragraphs. So, having a very organized approach to your list is essential. Compartmentalizing the information based on workflow, demands, and projects helps you get answers faster. So, if you’re showing up to these meetings with piles of paper, a non-impressive list, and approaching the time in a circuitous fashion, you’ve given off the impression that there’s no composure in your style. On the opposite, when you show up organized and ready to get down to business allowing for answers and feedback to happen swiftly, a sense of cadence begins to show up resulting in accomplishment being felt (this is the whole goal). Executives want to experience each meeting as a sense of accomplishment.

  2. Have suggestions to resolve some of your questions!  This helps the executive make a decision faster. That’s your value add. You show up with a problem, have strong suggestions, resulting in the executive feeling that you’re accomplishing things together. Now, for new relationships, I encourage you to show up with one or two suggestions (one could even been, “should I talk to so-and-so for help?”). Source new peers to assemble your suggestions and give credit if their suggestion is chosen. You do several brand developing things with this move. You express to your executive you have limited context, but know where to go to get more information. You want to build rapport with others. You wanted to make a strategic impact vs. only tactical. Your main goal is to help the executive make decisions in that meeting. Helping to elevate decision fatigue is your middle name.  

  3. Ask for autonomy and authority! If a suggestion you proposed is chosen, and you've been consistently building trust with your executive, seize the opportunity to assert your agency boldly. Instead of shying away, confidently seek permission: "I felt fully capable of addressing tasks 1 and 5 from my list independently. May I have your permission to handle such matters autonomously in the future?" This assertive move not only showcases executive composure but also communicates two critical messages: first, your approach is both strategic and tactical, not merely tactical; second, it demonstrates your organizational prowess and confidence. Embracing such calculated risks contributes to the continual development of your executive composure, aligning you more closely with the image of a seasoned and self-assured professional, potentially earning you greater autonomy over time.

Launch Pad:

  1. Make sure you have a strong list organized from most to least important.

  2. Come to each meeting with the calendar printed for the next two weeks.

  3. Come prepared to challenge energy allocation decisions (e.g., does your executive truly have to be in the 1-hour meeting or can they join in the beginning).

  4. Make the first half of the meeting a working-meeting, then move to your punch list. This way, the executive feels a sense of accomplishment at the beginning and end. This results in them craving meetings with you.

Enjoy the below podcast where I host an EA and her Executive.

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