Maggie Olson on How to Be an Excellent Executive Project Manager

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 The Leader Assistant Podcast. It's episode 283. You can check out the show notes and links for this episode at leaderassistant.com/283. I'm your host, Jeremy Burrows, and I'm excited to be speaking again with my friend Maggie Olson from Nova Chief of Staff. And Maggie, welcome back.

Maggie · 1:25

Thanks. Thanks for having me.

Jeremy · 1:27

So last time we talked in episode 281, we talked about leading and managing executive engagements, talked about how to prepare briefs, the different types, what should be included. Super, super helpful conversation. And yeah, if you missed that one, it's episode 281, leaderassistant.com/281 to check out that episode. But today, yeah, we're going to be speaking about how to be an excellent executive project manager. And I personally have project management experience. I was early on in my executive assistant career, I was an assistant for a few years, and I kind of shifted into sort of a hybrid project manager slash assistant role. And it was fun for a little bit. And then I got to the point where project managing a team for me was felt like babysitting. And so it was like, oh, you didn't do your thing you're supposed to do at this deadline and those kinds of things. And then I ended up becoming the founder's assistant and really diving into the kind of founder, CEO, high level executive assistant role, which still involves a lot of project management and project managing, of course. So I feel like I still still use those skills all the time. It's just in a different element. And so anyway, I think, yeah, I'm excited to hear your thoughts and from your experience and from your feedback you've received from the students in your course and just just how to be an excellent executive project manager. So yeah, let's let's dive in.

Maggie · 3:25

Yeah, absolutely. And I think you're right, Jeremy, like it's it's much different. The Chief of Staff role, the senior kind of high level strategic EA role is very different than just a typical project manager. But what we're doing is we're doing executive project management. We're managing all of the things that our executive is a part of and all the things that make the back office tick. And without a strong understanding or inherent ability or kind of the principles around project management, it's just a struggle to keep track of everything. Inherently, I don't think you can be hyper organized without being a decent project manager. So those two things definitely go hand in hand. But what I think is the cool part about the Chief of Staff role and the senior EA role is it can look how you want it. And often when I'm talking about the Nova Chief of Staff certification course and the Chief of Staff role in general, I tell people that you really do need to be very organized to be in either of those roles. But the way that you're organized can look so different. So when I'm talking to students, I say like, okay, maybe your room's a mess, that's fine. But how are you organized more than all of your friends in other ways? Are you the one person that is planning all of your friends' trips? You've got the Excel spreadsheets, you've got all the itinerary, you're coordinating with everybody. That's great, that's hyper-organized. Are you the one with color-coded notes for all your classes and different colored sticky notes? But you don't remember what you did yesterday? Well, that might be a problem. But you get the idea. How you are organized is the most important part, and that's the cool part about the Chief of Staff role, is you can set up systems and processes to work for you to accomplish what you need to do in the back office for your leader. One of the best ways that a Chief of Staff can support their CEO or business leader is by literally catching all the things, and I oddly, untimely wrote about this on LinkedIn this morning. So I'll share a little bit here, but CEOs need to operate in the vision space. They need to be able to have tons of ideas all the time, good ideas, bad ideas, potentials for collaboration and partnership, things with people and leadership. What are all the things, relationships, product, that CEOs should be staying in that vision and idea space? As a Chief of Staff, one of the ways you can add the most value is by setting up systems and processes to allow your leader to stay in that vision space. The Chief of Staff should have the tools created that basically enable all of the things that your CEO may throw at you to have a place to land without your leader needing to do much more than just share them with you. This can be, and we'll dive into the how here, but this can be simple or more formal, categorized lists that the Chief of Staff manage. Then after that, they can slide into more robust planning documents once they're flushed out and prioritized. But the point here really is that CEOs stay in the idea space and Chiefs of Staff manage, organize and often follow through on execution for their leaders. Today, we're going to focus on Executive Project Management. But first, I think that it would be a good idea to talk about how we can be excellent executive project managers for ourselves first. What does that mean? I have three things for you. One, build a walking deck. Jeremy, I don't know if we've talked about a walking deck before on our podcasting here.

Jeremy · 7:07

I think it might have been briefly mentioned, but not in depth for sure.

Maggie · 7:11

Okay. Yeah. I think we may have an episode coming up down the road where we dive even deeper into a walking deck. But this was a concept from a leader of mine, Katie Oakland that I had years ago. Essentially, if you're a PowerPoint user or a Google Slides user, we can absolutely have the conversation around why I think slides are helpful versus project management software. But you want one place to hold 95 percent of the things that you reference or update repeatedly. Basically, that could be short-term and long-term calendar views, your agenda templates, your travel templates, your rhythm of business because that definitely changes often. Your meeting follow-ups, your leader engagements. We talked previously on a podcast around all of the engagement activity that Chiefs of Staff can support. Pipeline views, your brief outlines, your meeting prep, executive team decks. Maybe your most recent staff meeting deck is in there because you're referencing it every day for the next two weeks till the next staff meeting. The things that you reference or update repeatedly go into this walking deck. What doesn't go in there are one-offs, big projects that require their own place or projects that just get too big. And that you're not referencing enough in your walking deck. A walking deck will enable you to move faster. It will be a little more friendly for your computer. Less things open, faster processing. It will likely always be open on your computer. I think it's always a good idea to close down at the end of the night, close things, let them sleep and wake up again the next morning. But it's likely always open during work hours. You can create sections in these decks like, here's my agendas and here's my rhythm of business templates. You will not have to spend valuable time hunting, finding, opening, closing things constantly and forgetting where they live. I also love, love, love adding archive sections to almost everything I do. All my folders, there's an archive folder within those folders. You just drag and drop in this deck. Also, old sites, drop it down into your archive section, delete it once you don't need it anymore. That's tip number one on how to help ourselves start to be excellent executive project managers. The second would be all around e-mail organization. Now, I use Outlook and I know that everybody listening does not necessarily use Outlook, but it's pretty common. A few things that I do here, I use categories and rules, but I don't overuse folders. The reason is Outlook's algorithm is very, very good at finding things. If you overuse folders, it becomes harder to find all the separate e-mail threads within all of your folders. Personally, I like categories a lot more than flags. Now, I know we've got a ton of amazing executive assistants listening, so I may not be telling you anything new here, but categories, you can have endless categories, you can color-code them, and you can coordinate as many as you want in terms of mapping out different tasks and responsibilities. So here's an example of how I use categories plus rules together. Let's say that we have a category that's green and we call it waiting to hear back. As Chiefs of Staff, we're always sending emails shooting Jeremy a note, hey Jeremy, can you let me know if this verbiage is approved? I got to wait on Jeremy. Set a rule where every time you CC yourself on an email, that email stays in your inbox and it changes to the green category, and the green category is called waiting to hear back. Now in your inbox, you know exactly what you're waiting on from other people. They're categorized a certain color and you know that you don't have to action them, but you're needing to keep an eye on them. That's one way. There's so many different ways. I'm not going to spend too much more time on email organization because we all use different platforms, but think about how this example could apply to the email platform that you use. Jeremy, do you have any email tips and tricks for how to be a great executive project manager for yourself? 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 · 12:02

Oh yeah, my first tip is don't use Microsoft. I'm just kidding. No, I write all about email management in Chapter 12 of my book, The Leader Assistant, and so definitely check that out if you're wanting some similar but different tips on email management for yourself or your executive. Because as assistants, especially like C-suite level assistants, often we manage our executives' inbox as well.

Maggie · 12:33

Exactly.

Jeremy · 12:34

It's even more important to have good tactics when it comes to email management.

Maggie · 12:39

Yeah, and it's something similar that I say for new chiefs of staff who are wanting to take on projects outside of their... Like they're wanting to take on company projects and help fill a gap and find this software or work on an extra project. I always suggest that you focus on kind of cleaning up and understanding and creating a well-oiled machine for your own back office first for that executive before you take on other projects outside of the back office for your leader. It's the same thing with this kind of conversation. Even though it feels like it's a time suck and it never feels like there's enough time, take an hour to set up, read Jeremy's chapter. What chapter was it again, Jeremy? Yeah. So dive into the resources that you have, set up some things to help you be as organized as possible because you're going to be so much more effective and less frustrated kind of hunting and pecking for things when you don't have that organization.

Jeremy · 13:36

Yeah.

Maggie · 13:36

Okay. So the last thing on the first, let's focus on us and how to be great for us is set up a wins folder, however you want to do it. Maybe it is in your email, maybe it's in your share drive folders, but set up a wins folder for yourself. Let's make this awesome project manager component for your own benefit too. So anytime you get an email from your boss or you complete a great project, or you have a solid review, or even somebody just says it was really nice working with you on this project, drag and drop, move it to your wins folder, wherever that folder is. Start this today if you haven't already started doing this, or repopulate the one that you started a year ago and you forgot about, and in six months, you will have some nuggets to look back on. If you're updating a resume and you're like, gosh, what are the projects I've done? Oh my gosh, that's right. Thank goodness I dragged and dropped this whole email summary of this project with metrics and stats here because I can then use it in the future to help myself. I'm sure Jeremy, you've talked about wins folders in the past too, but it's a quick one, quick and good.

Jeremy · 14:51

Yeah, love it.

Maggie · 14:53

Okay, so let's switch gears and talk about why project management is important as a Chief of Staff. I'm going to share a scenario and people listening can think about if this is their leader. You have a very busy leader. Sometimes it feels like new idea whiplash. There's a new idea thrown out at every turn right and left. Your team is trying to execute on your leader's wishes, but they're getting mixed messages about what's most important. It's also hard for you to follow what your leader's saying because there's a million things flying all over the place. You wish you had a clean, neat, easy list of all the leader's priorities in rank order. Does this sound familiar to anyone? Because I think it's pretty common.

Jeremy · 15:43

Definitely can relate to that.

Maggie · 15:45

Yeah. It's one of those things that good leaders are crazy vision idea-throwers. We have to figure out how to support those people so that, as I mentioned earlier, they can stay in the idea space. As a chief of staff, you're going to add incredible value if you can help articulate, guide, track, and lead the business forward for your leaders' most important priorities and capture all the other things that maybe don't seem important, but they need a place to live. How do you do this from start to finish? First, I would suggest starting with informal but organized, categorized lists for literally all of your executives brain dump things. Ideas, collaborations, partnerships, people, leadership, relationships, product, your categories might be a little bit different. You can track this wherever you want. If you're using a walking deck and you want to pop them into PowerPoint, great. If you're using a shared Google Drive, Google Sheets, perfect. Then start noticing if certain things are thrown out, certain ideas are thrown out repeatedly more than others. Note this, take note of it. Start realizing that, gosh, they've talked about hiring those two new people like four times in the last three weeks. This is your opportunity to add strategic value during your one-on-ones with your leader. And what that would look like is there's a few things. In a normal one-on-one setting, you're bringing up, you're bringing up, hey, I've heard you mention this. Here's the things that I've captured this week from you. Do you want to chat through any priorities? Just want to let you know that I've observed that we've chatted about this three or four times. Is there anything I can do to help launch or move this along or execute? Those are conversations you should be having. That's a little bit more of the informal, but organized place for things to land, your categorized lists. Now, over time, you can flush these ideas out with your executive and they can work their way into a president's key priorities document or something similar that's a bit more formal. I also recommend, we actually have an exercise in the course that does just this, that you orchestrate a specific forum with your leader to have brainstorming sessions about the most important priorities on your leader's plate. That probably looks like quarterly sessions where you chat through your president's key priorities and you more formally capture them, rather than just a place for things to land on a day-to-day basis like we were talking before. Before I move on, Jeremy, anything to chat through there and I'll definitely share what this president's priorities document could look like and things to keep in mind.

Jeremy · 18:39

No, I think you're doing great and I'm soaking it all in.

Maggie · 18:42

Okay. Awesome. What does this president's radar, key priorities, obviously the title is interchangeable look like? Again, I'm a fan of Excel, excuse me, PowerPoint, Microsoft. Jeremy has me laughing about his Microsoft comment. I love Microsoft, but I've grown up on it. Also, Apple lover never fit with my Microsoft corporate world. Yeah. But when we think about PowerPoint, yes, you can keep things in software management platforms. And there's tools and gosh, there's going to be so many more coming to the market with AI every day. But the problem that I ran into is having things that are quick and easy to share with executives the second they need them. Up to this point, I have not found any kind of a project management software where you can just export and it's polished and presentation ready. Now, again, the level of formality isn't necessarily important for everybody. But in the world that I came from, supporting a Fortune 40 president and boards and all of that, polished, elevated, braided materials were important. And PowerPoint allows you or Google Slides allows you to have a very nimble and flexible project management template that's always ready to share. And so it doesn't take you more hours to create that part. But we can totally debate that on another podcast, too. So when we think about what does this slide look like, your kind of top priorities, president radar, you want to have a priority rank for the amount of time or just the initiative, how your leader sees that initiative, that priority. Do they see it? Not everything can be number one. So this can be one of the most telling conversations with the leader. Where do you rank everything? Okay, they're all number one. Let's revisit this one.

Jeremy · 20:48

They're all urgent.

Maggie · 20:49

They're all urgent. Everything's urgent. All 27 things should happen this week. Okay. And then a description. What is the key priority? How would you describe it? Additional details, which is really just like describing that priority. And then what are the touch points? Maybe it's a meeting or a weekly summary that drives this key priority forward. So to back up a bit, this document is for the things that we flushed out as major priorities and important. They're not for all the millions of ideas that your leader is throwing at you every day. This is the document where those ideas graduate to. They've now become a very important priority for your leader. And this document can also come out of that, maybe quarterly session where you just deep dive into your leader's most important priorities. So when you have an extremely important priority, there should be some form of a touch point, a meeting or a weekly summary or something where the leader is receiving the information that they need to understand the progress and the status of their initiative. You should have a lead on this document. So for each initiative, who's the lead? It can't be you for everything. It can't be the Chief of Staff for everything. It can't be the CEO for everything. This is important part of delegation. Does this item live within operations or can it a little bit, for example? Then what are the next steps with dates? This meeting needs to be scheduled. This daily session needs to happen. Double-check invite lists. These are just some ideas, but a flexible document to make sure that you can share with your leader at any time, and that helps your leader stay focused on their most important initiatives, even when they have so many ideas all the time.

Jeremy · 22:38

Super helpful. Awesome. And what are the challenges, or what are the speed bumps that you see when people put this together, and they have this walking deck, they have this project management systems and processes in place, and the team they're working with or the executive they're working with, doesn't really want to abide by it or really seems disinterested. Does that make sense?

Maggie · 23:12

Yeah. You know, I think the hardest thing to do sometimes is to track down your leader and to have them commit to that working session with you. And gosh, there's a lot of ways we go about that. But I think consistency is very important, showing what a final product could look like, reminding the leader that their team needs direction and clear direction. And this is something that's going to really help from a kind of wide team scope to collaboratively understand the priorities of the team. It is definitely tough to get the leader to hold that time on the calendar for you. But I think that with anything, the more consistent we are with these sessions and the more consistent we are with vocalizing to our leader, the why and the what and the how of the importance of things like this, that's really the best we can do. And after that, we cannot control other people. And I try to share that with people because it can be a little freeing. We can do everything we can. We can have great systems processes. We can be flexible. We can test and learn. We can throw this one out and this one in. If your leader is not in a place where they want to or have the ability to sit down and have a conversation with you or adopt a new tool or process, there's sometimes there's nothing else you can do. And so it's time to move on to the next strategy or the next tactic to try to hurt all the sheep.

Jeremy · 24:37

Yeah, makes sense.

Maggie · 24:39

Yeah.

Jeremy · 24:41

Awesome. Cool. Well, any other project management tips or is that all for this episode?

Maggie · 24:50

You know, the last thing I was going to mention is just for these specific forums where you're, okay, I'm going to, I want to do this brainstorming session with my leader. I think this would be really effective. If that's you listening, the steps that I would suggest taking to make that happen is, one, set up the meeting, two, record the conversation, three, also take great notes. And in those notes, maybe it's like the time of the recording so that you can jump back there. Obviously, like ask good questions, be prepared with that project management template. And as I usually mention, please email us at hello at novachiefofstaff.com to get a version of our PM template. We are more than happy to share that with you totally for free. And then you basically start to get organized. You figure out what you can own from this list. You figure out a process to keep it going and process will help with that executive commitment. You help the leader's team stay focused and then you review this document consistently and you're really, really flexible with changes. So good luck. This is not a small undertaking, but hopefully you have picked up a few things that can help in your journey to becoming or continuing being an executive, an executive, excellent executive project manager. There we go.

Jeremy · 26:05

Love it. Awesome. Well, thanks again, Maggie. Great tips and practical tricks and tactics. We'll put those links in the show notes at leaderassistant.com/283 so people can reach out and yeah, request that template and learn more about Nova Chief of Staff. So thanks again and we're excited. We've got a few more episodes in The Hopper to talk about some more exciting topics in the future.

Maggie · 26:34

Awesome. Thanks, Jeremy.

Speaker 2 · 26:46

Please review on Apple Podcasts.

Jeremy · 26:55

goburrows.com.