Maggie Olson on Leading and Managing Executive Engagements

Jeremy · 0:00

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Speaker 2 · 0:47

The Leader Assistant Podcast exists to encourage and challenge assistants to become confident, game-changing leader assistants.

Jeremy · 1:04

Hey, friends, welcome to episode 281 of The Leader Assistant Podcast. I'm your host, Jeremy Burrows, and today I'm speaking with my friend, Maggie Olson again. Welcome back, Maggie.

Maggie · 1:15

Thank you.

Jeremy · 1:17

So we're gonna talk a little bit about leading and managing executive engagements, and all the things like preparing briefs and engagement recommendations. So yeah, love to jump in, but tell us a little bit about before you take it away, why this topic?

Maggie · 1:41

Yeah, so one of the biggest impacts that an executive support team can have, and that includes strategic high-level executive assistants and chiefs of staff, sometimes other roles as well, is preparing the executive for everything they step into. Chiefs of staff should take it on themselves to ensure that a leader is not stepping into a meeting or getting on a plane or going to an event without understanding what they're getting into, who's going to be there, what are the priorities of them being there, what do the other people, like the external folks want from your executive? So we'll get dive deep into this, but that's why it's so important and such a kind of a hot topic for us, both in the Nova Chief of Staff certification course that I run, but also just for Chiefs of Staff and high level executive assistants everywhere to have a strong impact in preparing their executive for whatever they walk into.

Jeremy · 2:40

Nice. And so is that kind of the definition of an executive engagement?

Maggie · 2:47

Yes. So I kind of talk about engagements as anything that your leader, and I'll use the term like president, CEO, business leader, principal, anything that your leader is taking part of and it can be internal or external. So internal engagements would include things like what your president is doing with your own company, where are they speaking at, what groups are they showing up for, and how do they need to be prepared to attend those events? Which employee groups are going to be there? What did he talk about last time or she talk about last time? The list goes on and we'll dive into that. But this could also be like a high-stakes sales meeting, all hands for their own team, a guest speaking spotlight at a peers' all hands meetings, company and all company recognition trip. Like, oh, the top 1% of sales employees go to Hawaii every year. You better know every single one of those employees and how they're performing and why they're there. So those are the internal engagements. And then there's the external engagements, which would be anything outside of the company that they are speaking at or need to be prepared to walk into even if they're not a speaker. So maybe your president is literally doing a Ted Talk. Maybe they're a guest on a talk show or they're attending a trade show or they're speaking at their alma mater's graduation. Anything your president is showing up for should have some level of preparation and you'll work with them to understand what that looks like because it can be very different for a lot of different leaders. Maybe they need a brief, maybe they need travel details, maybe they need a script, what to say. And maybe they need photos of everybody at the meeting. Or maybe all they need to know is what time to show up. You have to figure out as a Chief of Staff or high level EA, what are the details that they need based on who they are as a person and what they're walking into. It's definitely a partnership between that back office support staff. But essentially, you're just ensuring that they're consistently getting what they need and staying on top of everything they're attending and that you are in the know for everything that they're doing and showing up to.

Jeremy · 4:50

Love it. Well said. I think that the point that I wanted to highlight that you brought up is that every executive is different. Some executives like really detailed, printed out briefs and everything before every big meeting. Then some executives just want a really short Slack message with the two bullets on the context of this meeting or this engagement is. Yeah.

Maggie · 5:18

And sometimes that's all they've known, right? It's like, well, all I need you to do is to text me. And maybe that's an area that you identify as a place where you can add more value. You know, I think they actually could be a little bit more prepared. I think they went to school, they went to undergrad together. And does he remember that or does she remember that they met a few years ago? There's opportunities that we can see and find to formalize a bit. But to your point, Jeremy, it's going to be up to the leader on the true level of formality that they would require. Print out, like you said, branded fonts, formatting, all the things. Maybe that's kind of the norm in the corporate Fortune 500 world. At a startup, maybe it's a text with the key details or just an email or a shared OneNote page. It can really vary.

Jeremy · 6:11

Well, let's jump in more then. And why don't you take it away and just talk through how to help our executives be more prepared and how we as executive assistants or chiefs of staff can lead and manage them.

Maggie · 6:28

Awesome. So we're going to talk through kind of three components here. The first is overall, just like management of your executives' engagements and how do we do that. Then we're going to talk about engagement recommendations and why it's helpful as a chief of staff to make recommendations for what your leaders should be prepared, not prepared for, but what your leader could walk into and show up for based on their brand and their goals. And then we're going to dive into kind of the meat of how we prepare briefs and what should be included in a brief that prepares your leader for what they're walking into. So we kind of touched on this, but for any type of engagement preparation, formality level is going to be like TBD. It's going to depend on what they're attending. It's going to depend on who they are as a person, the formality level of your company. I would suggest playing around a bit with elevating, adding a little bit more formality than maybe what exists now, just to see if it hits right, just to see if it's helpful to your leader to have a little bit more formal preparation. Just kind of consider where you're at now, take it up a notch and add value through the elevation of materials that chiefs of staff are kind of known for doing. So the formality level is very, very flexible. We will kind of talk through some scenarios here that are slightly more formal, dependent on what your leader needs. And then the preparation level depends also on kind of what the leader is walking into. So if they're speaking at an event, they probably need to know a lot more about who the other speakers are and the hosts and who's listening to them and where they go, what they say, all the details. But if they're showing up to an event and they're mostly listening and absorbing maybe other speakers, they probably need the agenda and they need the event overview and maybe there's a few peers they're joining with. But it's really going to depend on how deep the preparation needs to be based on what they're attending. And then we'll chat through recommendations. So an engagement recommendation is a way for you to add strategic value. What I mean by this is once you get to know your leader, you understand their internal priorities, you understand their external priorities. Where should they be showing up? Are there conferences? Are there summits? Are there CEO groups that would make a lot of sense for your leader to be engaged with? So from an engagement recommendation perspective, what does this look like? Well, in our Nova Chief of Staff course, we have an assignment that I'll share. I took this from many real-life scenarios as a Chief of Staff, so this will give a little bit of an insight to what engagement recommendations look like. But essentially, if I continue down this example of a summit or a CEO group, we ask our students in the course to basically research three different engagement options for the CEO. And we give a profile, here's what the CEO stands for and likes and where they work, and here's all the things. Now, go and research what makes the most sense based on your leader's seniority, what they're into, your company. There's a lot of things that could be weighed here. And then truly create a document, create a recommendation that reads both kind of as an event brief, here is what the event is, but what's most important at the top is what your recommendation is. I recommend you attend this, insert here, conference, summit, CEO training, whatever it is, for the purpose of X. And that may be to increase your brand awareness in this key category, for example. But you're recommending where your leader should show up to, and that can include internal and external recommendations. So as I mentioned, we kind of have an exercise that walks students through this. I think that it's a very valuable way where everybody's always kind of trying to figure out, how do I add strategic value? This is a huge way to do that, by kind of driving the car of where your leader shows up to and how they present themselves.

Jeremy · 10:43

What's an example, or could you give us a little bit of a snippet from the exercise that you run them through?

Maggie · 10:50

Yeah, so we offer three engagement options for students to go research. I think we use the CEO of Instacart, Fiji Simo. So students research the CEO and they research the engagement options. One of the options is the G100 Chief Executive Program. Another is the Yale School of Management CEO Summit. And the third is the Leaders on Purpose Summit. I ask students to choose which one they want to recommend for Fiji and then to put a brief together. And we'll dive into what briefs look like. That includes an overview of the event and what to expect, what your CEO will get out of the engagement options, what a successful event looks like. I ask for consistent formatting, polished, elevated materials. Maybe that means like your branded colors or use of a logo and something that's ready to share with your leader. Limit ideally one page, maybe longer if the engagement has some long agendas that you want to include. And then I say, make up the details that you don't have. Maybe you want to play around with somebody that your leader went to school with and include like three key people that are going to be at the conference and why it's important to shake hands with those folks. Those are things that kind of make you think outside of the box that if I give all the details in an assignment, it's just not real life to a chief of staff world. So I ask students to basically submit this engagement recommendation that reads as a recommendation and includes an event brief for what the leader would be walking into.

Jeremy · 12:25

Thanks for sharing a little bit of a sneak peek.

Maggie · 12:28

Totally. So anything else from you, Jeremy, on kind of the... I'm thinking too that for this type of work, I usually recommend a Word document. I'm a PowerPoint lover for other things and we'll get into that. But for anything that's text heavy, something like Word or however you choose to display a little bit more text heavy work is probably best. And I usually suggest more bullets, less paragraphs, most important information at the top, simple formatting, clean, neat, easy. But those are some of the things that we talk to students about a lot. Are you ready to elevate your career in 2024? I'm Maggie Olson, founder of Nova Chief of Staff Certification, the first of its kind online course for aspiring and existing Chiefs of Staff. With curriculum taken directly from on-the-job responsibilities, Nova's self-paced learning modules provides you with hands-on experience so you can feel competent and confident moving into a Chief of Staff-style role. It's the perfect next step for executive assistants. Head to leaderassistant.com/nova to learn more, grab the syllabus, and enroll today.

Jeremy · 13:45

Nice. Yeah, and you know, it depends. You know, we're a Google shop, so we use Google Docs. And generally, what I will do is I'll put those briefs in the calendar for my executive, because he likes to just have the Quick Bullets context in the actual invite, so that as he goes to his next meeting, he doesn't have to go to an external source for the details. He can just open the calendar invite, see the details.

Maggie · 14:14

Yeah, I love that you put that right into the event, the calendar invite.

Jeremy · 14:18

Yeah. Yeah. Yeah.

Maggie · 14:20

And I'm guessing since you're all virtual, there's no paper needing to be exchanged, which is nice.

Jeremy · 14:25

It's one of my requirements to jobs now is that I don't have to print a bunch of stuff all the time, because I don't like printers.

Maggie · 14:31

Yeah, they're the worst. Cool. So we're going to move on from the recommendation portion of engagements. I always share when Jeremy and I chat that I'm easy to get a hold of. You can email us at hello at novachiefofstaff.com if you have questions or you want a template, anything like that. We are here to help. So moving on to kind of the management of these engagements and then we'll dive into the meat and potatoes of the brief. And I laugh when I see meat and potatoes now because I'm a true midwesterner now that I live in Lincoln, Nebraska. It's more there's more backing to it.

Jeremy · 15:10

So it's not quinoa and sweet potatoes.

Maggie · 15:14

It's still it's still kale. And yeah, quinoa. Yeah, I wish there was more of that here. But again, I'll go to Kansas City for that. All right. So managing engagements. This is probably most pertinent to leaders, which I think there's probably a lot of that are involved in five to ten events, internal and external, across a week or two. So you basically have a lot going on. Your leaders showing up for all hands meetings and peer all hands and gosh, off sites and board meetings and sessions with employees. And then they're also showing up to external events and shaking hands and speaking. So if you have a leader, if you're in an environment like this where five to ten events every couple weeks, you might want to consider some type of a what I call a pipeline document. So this would be like an engagement pipeline preparation document. And one way to do this, the way that I teach and recommend is to kind of have an executive view of the doc, which is everything that's confirmed for the next two weeks or so in one view, and then have more of a working view for everything else. And that could be like the next six, seven months. There's some things that are TBD we don't want to lose track of there. But it's what's coming. It's a pipeline view all on one paper. So you're not clicking through outlook calendars. It's a little hard to see visibility wise when you don't have everything in one spot. So this is a way to have a pipeline view of like, here's the next two weeks, engagement, executive ready, polished, and then a working team view for everything else that could truly be like two or three pages. Do you have experience Jeremy doing stuff like that? Are you guys doing kind of pipelines?

Jeremy · 17:05

Yeah, we, I think generally it would be, we do a lot of spreadsheets, little Google Sheets, where we're tracking information and following lists. And then if we're doing events, like we had an event this week that my CEO went to, and we had a Google Doc that was basically the entire schedule and context, a little more in-depth if, you know, he really wanted to be like, all right, what the heck am I going to? And wanted to really dive in on the way there. But yeah, it's, it really depends. It really depends on how many team members are involved, how many, how much new, newness to the engagement there is versus kind of regurgitating the same talk track. You know, these five events.

Maggie · 18:00

Yeah, yeah, totally. So if we were to break down the executive view of our engagement pipeline, which is sort of the next two weeks, let's see everything that's come in the next two weeks. This is something you could literally hand or send your leader. The things that should be on here are basically any engagements, internal or external, that are confirmed. I like to organize this document so that it includes a few things. One would be the type of event. Ours, you know, are usually categorized, maybe most are usually categorized into kind of a major reoccurring event, an ad hoc one-off speaking event, or a business engagement. Those kind of tend to cover most of the categories. Yours may look a little bit different. So what's the type? We like to use icons for this to break it up and make it a little easier to see. What's the date? Put it in chronological order. So the next thing coming is at the top. What's the event description? What are the details? And these are the most important things that your leader knows, not the details that you and the working team need to know. This is a leader view. So it's just for that leader view. And then when can they expect the brief? So the engagement pipeline is not a brief document. It's not in this example, it's not telling them what their talk track is and who's going to be there and what the agenda is and all of the things. It's telling them, keep these, keep this on your radar. This is what you have coming up over the next week or two for the things you have to show up to and be prepared to kind of shine or speak or be very live for. So that's the pipeline. When you think about kind of the working team view of the pipeline, maybe that's longer, several more pages potentially. There may be a few different topics, but additional information in here would be who's the team lead, who's the brief owner, more detailed next steps, status. Those are things you don't always need to share with your executive. And I think that takes some time to figure out what are the details we share with our leader. And this goes well beyond this engagement conversation. And what are the details that are just working team? And so hopefully that gives a little bit of light there. So that's probably it from our engagement. How are we managing the engagements? We've got a pipeline view for the leader, and then we've got a working team view, and then we can get into the kind of meat of briefs here in a minute.

Jeremy · 20:21

Sounds great. Yeah, let's do it. This is all good stuff. Lots of good stuff. I'm sure there will be a lot of people hitting pause and writing down notes and then rewinding and going again.

Maggie · 20:33

Love it. Okay, awesome. So let's chat about creating briefs. Again, the purpose of a brief is to prep your leader for whatever they are walking into. We mentioned the level of prep will vary, but I'm going to go through some things to consider in a moment here, and you're likely only going to choose a few of these things to include in your brief dependent on what the actual engagement is. But as a chief of staff, it's important to know when I'm talking through this that you may not be the one putting these briefs together. You're definitely going to be involved. You're going to make sure your leader's getting it on time. You're going to make sure the process has been kicked off. You may set up the process and own it for a while to ensure it's running smoothly. Or maybe at the end, you're just finalizing the brief. Either way, a well-done brief requires really strong process and collaboration. For example, if you and we'll kind of dive in here, but if you are wanting to brief your leader on the most recent sales information about, let's say your leader's meeting with another CEO of one of the products that your leader sells, and you want to talk about performance or the last sales meeting, you are definitely going to need to loop in the sales team to get the relevant information. And you may also be working very closely with the EA. You may be working closely with another group that just talked to these folks last week. It's a very, very strong process. It's driven by process and collaboration. We get into a lot more of this in our course. But when it comes down to kind of perfecting and practicing briefs, it really, you just need to do it a couple of times and you'll feel super comfortable with it. So components of an executive brief. We are going to chat through logistics, some things to consider there, third party, things to consider if your leader is meeting outside of your company, relationship with the person that they're meeting with, and then kind of the responsibility of your leader in the meeting. So let me dive into those. So from a brief perspective, what are the logistics that you want to include? And again, it doesn't have to be all of these. Potentially date and time of the meeting, key attendee names, audience, if applicable, number of attendees, if it's an event, agenda, if that's the type of event they're walking into, high-level summary of engagement goals, potentially the technology to be prepared with, Zoom, in-person, pre-recorded, music, whatever it is, and maybe some background about this event if it's applicable. So those are all potential, probably pretty important things to include if it's applicable for the thing that your leader is walking into. From a third-party perspective, who are the other executives attending and what information is needed to complete a good, you know, small summary of a biography? Which executives are attending the meeting internally and externally? Any personal facts that could be relevant? Company, organization, overview from the other company that we're meeting with, their industry, their sector, maybe their company size or market cap. Maybe their employee count is really relevant because you're talking about employee software, for example. It all depends on what your meeting purpose is and who you're meeting with. Potentially their headquarters location, their company, strengths or opportunities if those are public, and then any key business updates or relevant things in the news that you want your leader briefed for before they walk into a meeting with this third party. Next category here would be our relationships. What are our business opportunities, initiatives, partnership goals, engagement objective? Why do we want these people in our ecosystem? What's our goal, our business goal? Our company business goal or our individual team business goal might be slightly different than our leader's business goal with the specific person they're meeting with. If our CEO is meeting with another company CEO, they may have some goals to be thought leaders in the space and partner there a bit. Our company goals may be to sell X number of products. Both of those things are really relevant, so thinking about what are the goals of the company as well. Current KPIs with the company, last interaction and noteworthy outcomes. When did we meet last? What did we talk about? The lead individuals from our team and their team, managing the relationship. So the leader may be meeting with the CEO, but their VP of product might be the person on the account. Our leader should know a bit about the VP of product. Other areas within our company that the third party may work with could include technology, marketing. So you can kind of see here this is not comprehensive, but there's a lot of places to go. And I think most importantly and finally is what is the president's or the leader's role and responsibility in the meeting? Why are they there? Why does somebody want them there if it's not driven by themselves? What's the key message to get across? And if you need to include some script or some bullets around talking points, those should be on a brief.

Jeremy · 25:47

Minor detail, right? Like why am I at this meeting?

Maggie · 25:51

Yeah, exactly. It's been forgotten, believe it or not.

Jeremy · 25:55

Right, yeah. Well, and then if you can't answer that question, then maybe they shouldn't be in the meeting at all. And then there you go. You saved them some time.

Maggie · 26:04

Absolutely. Yeah. So I have a final example here for you, Jeremy, of like an example brief that we include in the Nova Chief of Staff certification course if you want me to share it.

Jeremy · 26:15

Yeah, that'd be great.

Maggie · 26:17

Okay. So this is an example of how we are absolutely not using everything that I just went through. It can probably sound a little daunting as I'm kind of reading off the list of all of the things included in potentially an executive brief. So here's a sample brief of what we teach in the course. So this is a, and I'm just going to describe it as best as I can. This is a marketing meeting between, for this example, Microsoft and TechSI marketing discussion. We have meeting logistics, the date, the time, the Zoom link is in the invite. We've got the meeting attendees, TechSI, there's two people attending, CMO, Marketing Director, Microsoft, we've got the EVP and CMO attending. Meeting agenda, we've got two o'clock introductions, 2.05 product demo, 2.20 open discussion and Q&A. Meeting summary, TechSI and Microsoft partnership for the product launch in January 2024, et cetera, et cetera. A couple more sentences there. Product launch details, the reason why we product launched and the most recent information would be in that section. And then we've got some background information on the kind of the lead on the Microsoft side, the EVP and CMO. We've got a link to his LinkedIn and three bullets about the background for this leader. And really, that's it. So it can look really comprehensive. It can look quick. But that's an example of kind of where we land across all the options for a brief.

Jeremy · 27:52

Love it. And we'll obviously people can reach out to you. I'll put your bio and your all the links and everything in the show notes at leaderassistant.com/281leaderassistant.com/ 281 to reach out to Maggie. If you have any questions about any of this or if you want to see some of these examples and learn more about their certification course. But yeah, Maggie, that was great. Great conversation. Great, great topics. Super interesting and helpful and practical. Appreciate you sharing. And yeah, we'll look forward to hopping on another conversation and talking about some other interesting topics soon.

Maggie · 28:37

Well, thanks for having me, Jeremy.

Speaker 2 · 28:49

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