Your Annual Strategy Meeting: A Playbook for Leaders with Dan Clifford

Getting the offsite on the calendar and choosing the right venue

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00:30Bill Gallagher: It's time to update your strategy and get your plan done for the year. As we record this today, we're heading into annual planning season. And we're going to share with you today—I've got a great coach here who works with me quite a bit, and we're going to talk through all the secrets, everything we know and do. We're just going to dump all the ideas on you. You can use this as a recipe card to get your annual strategy and planning work updated. It's the latest of what we're thinking about, that kind of thing. We'll walk you through everything, so stay tuned.

01:05Bill Gallagher: Hey, everybody. Bill Gallagher, Scaling Coach and host of this super fine show, Scaling Up Business Podcast. I've been coming here every week now—I don't know, 650 plus episodes—everything to do with growing, scaling your company. We do, in addition to the show, we put on workshops, we have coaching programs, we have cohorts you can join, things like that. So check out everything we got at scalingcoach.com. And if anything in this show strikes a note with you, just send the email to info@scalingcoach.com, or just go to the website and click a link and talk to us. See if we can help you.

01:45Bill Gallagher: Alright, so Dan Clifford joins me. Dan, welcome to the show.

01:50Dan Clifford: Yeah, great to be here.

01:52Bill Gallagher: So Dan and I have been friends for many years now, several decades really, I think. And we met through the EO organization, once upon a time known as YEO. And so Dan had a company and he exited that company. And I've had several, and we now do quite a bit of coaching work together. And Dan lives actually right nearby, not far away, and is involved with our group and that kind of thing. So lots of experience in Dan across industries, particularly tech, but he's worked with quite a few companies in different sectors, that kind of thing. And I'm delighted to have you on the show.

02:21Bill Gallagher: Great. Can't wait to talk about that. We're just going to talk about everything that goes into it. So we're going to go through before, during, and after. Right? Like, before, during, and after. We're just going to kind of rip through what goes into it. We'll share with each other back and forth. We're going to riff on it. You listen in, make your notes, look at the show notes. You should get a good recipe for what to do. So, before, Dan, what's your first step? Where do you go to? Like, if you're going to set up for your company or for a client, what's first?

02:40Dan Clifford: Yep. Well, the first thing—I think people forget the before step. They throw a meeting on the calendar and they all just expect, let's just show up and have a day. But really, I think the important work is the work that leads up to it. Almost like—you and I, we've done triathlons before, Bill. Yeah. Like, often it's like the training. All the stuff you do leading up to it is where all the important work happens. So first thing is, I think, get the meetings on the calendar and then set a schedule leading up to it. Like, even a month in advance with some to-do items, and we'll talk about some of those.

03:17Bill Gallagher: What's your favorite? I think one of the things you offer maybe, just… Yeah. Yeah. For sure for me is, let's get it on the calendar. So get it on your calendar, on everybody else's calendar. Get it on people's calendar who you might want to be—have them really look and think about, is their calendar clear? People's calendars are a mess. Their spouses have expectations of them. They're like, oh wait, I can't go away that day because I've got a this or that, or it's just not there. And so really getting the calendar clear seems basic, and yet I think it's so fundamental. Like, it begins everything. And then you mentioned, like, let's start to calendar the rest of it. So when are we going to prepare? How are we going to prepare? What does it look like? It helps to have an idea of the end state in mind in order to plan all that out, but the calendar is the first. And I think going hand in hand with that is, where's it going to be? Yep. Where's it going to be? And I think in general, doing it in your conference room or your own office, that kind of thing, is generally a bad idea. Right?

Pre-planning logistics: room size, indoor-outdoor access, and budget hacks

04:33Bill Gallagher: Yeah. So location for me is the next thing. So I want the time, and I want people's calendars blocked and that kind of thing. And then I want a really great location. So when you think about a great location, I think there's degrees of it. And I'll share a couple of them. But what for you, Dan, is the—what constitutes a great location? What do you think?

04:53Dan Clifford: Yeah. When people call it an offsite, really, it's like offsite is good. Get away from your normal day to day. And even just changing the environment, something that you can feel… If you can afford it and whatever you can do, but like, something that's maybe sunny, maybe close to the outdoors, outside even your city, something that is… You know, enough space to move around. So sometimes in these meetings, you're up, you're using whiteboard, you're getting up and moving around. If you're having a multi-day event, have a place—that's a good hotel or maybe it's in a hotel. Just having something people can feel a little more relaxed and not just feeling that day-to-day work pressure that they might typically have.

05:43Bill Gallagher: Yeah. So I fully agree. I want to see light. I want to have indoor-outdoor access. I want an inspiring location that makes me feel good, abundant, optimistic. Right? I want to set up that whole situation. I think the scene makes a big deal. We do a bunch of them for private clients and also for our small companies in our group program, and we'll tend to use waterfront locations. Right? I also have done mountains. In the January, December-January time frame, some people don't like to get to the mountains. You and I like to go skiing, but it's not for everyone. And so we have a mountain hotel that we use more than any other place up in Lake Tahoe area. And then there's a waterfront in San Francisco. There's some locations in Southern California. There's a particular room that I really love in Laguna Beach. So there are these kinds of places, right, that are useful. And then there's like the next level. So I just got back from a multi-day sort of ten-year planning, five, ten-year planning for our lives, for a bunch of entrepreneurs, a bunch of like EO alumni type folks, EO YPO. And we gathered on a private island and we dove into it for four or five days with people. And, you know, so there we are. Like, everything's awesome and beautiful. Well, you know, it's definitely a little more expensive and really, really useful for entrepreneurial couples to start to think about their life. So big, expansive. It took like two days to get there, really. There's a place in Mexico right now. There's a place in Santa Fe. There's… So those are bigger investment kinds of things that you might want to do at key moments, or just because you're feeling like I really need like a reset.

07:36Bill Gallagher: Just find a place with a great view. But you said also, like, the location. So I mean, the size of the room. If you have eight people or six people and then you get a six or eight person conference room, it's not gonna be great. It's gonna be tough. Right? So in general, double it. So if you have a group of seven people, get a 15 person conference room. Get, like, bigger like that. And no, like, hotel interior windowless rooms. Those are just awful. Like, if there's anything that makes me not wanna be in business or maybe even live another day, it's an interior room at a major hotel chain.

08:19Dan Clifford: I'll throw out an alternative to just to rent it. You know, if if you feel like the budget is an issue with, like, getting a good spot, even just trading rooms with another entrepreneur that you know or just another place, just find a place that's off-site. So that when you're on-site and your employees are there, you're gonna look at everything. You know, look at all the things that need to be done. You don't want that. You wanna be away from your company, however you can get that done.

08:44Bill Gallagher: Yeah. So great budget hack ideas. Right? You don't have to spend a lot of money to do this. And spend it on, if you have money to spend, spend it on the kinds of things. So if you wanna travel, that kind of thing, great. We did a kind of a launch off-site a couple days in Mexico a couple years ago, but that was for a company that, you know, we knew was gonna get to a billion dollars. So, even at the outset, we were, like, investing differently for a different kind of future, creating a real expansive thing. So we all flew out of town. But going to the budget thing, so trade rooms with a friend. Maybe you have a great conference room. Say, hey. Listen. You use mine. I'll use yours. Exchange swap with a buddy. Another one that often is on the free side. If you have a big law firm or if a big law firm's been courting you or a VC firm or a bank even, we used to use a bank conference room in downtown San Francisco. Was really beautiful conference room, running downtown San Francisco. And I did banking with them. My clients often did banking with them, and they were like, hey. Just use our room. It's, like, free. You know? So there's free room. Major law firms that we've used on deals and with clients in the past, they have beautiful conference rooms, and you can use those free, again, for the most part. Well, I guess you paid a lot for them over time. Right? So, they're counting on that. So I, there's things like that. And then there's some other, like, creative spaces. Here's one that I find again and again. Most museums have an interesting conference room that either has a great view or some, like, connection to the museum in some way. So, like, an automotive museum is gonna have a real cool car themed room or, into some regional kind of thing. You might find that they are really cheap. They they don't book them out a lot. So museums can be a fantastic place to get an inexpensive conference room that is also kinda creative and cool in some way. And then, if it's midweek, which it usually is for this kind of meeting, you can arrange a private tour of the museum at the end of the day or or whenever. Right? So that's another one. It comes through clubs. If you belong to a golf club, a country club, a lunch club, their clubs could be another one that's fairly inexpensive. Probably the worst deal and the worst experience is a major hotel chain. Name, you know, your major global chains. Terrible deal, ugly interior conference room, premium pricing for, you know, average food at a buffet line.

Budget alternatives to expensive hotel conference rooms

11:22Dan Clifford: Yeah. Right. Right. And that's what people think of first. So it's good. Yeah. We're talking about some of the other things that you can do.

11:30Bill Gallagher: We did one at, there's a hotel, you know, a couple of miles from our houses here, and I love doing meetings there. But it's like, okay. The breakfast was $98 a person. Lunch is $150 a person. It's not awesome. We did have good views from that conference room. But, like, really, is it, and then the, you know, the AV is gonna cost you $2,000, and that's all terrible. Oh, here's another funny hack with the logistics location. So I do boot camps a couple times a year with Verne Harnish, and we were griping about the AV cost and the thing when we're trying to set it up. And, you know, we wanna make a little money on it as well and not have it be a fun inclusive thing. And so it's thousands of dollars to set up a screen and projector. We're like, why don't we just buy our own? And so we bought our own projector and our own screen, and we just we just ordered it in. And because I could drive there, I just kept it at my house. So we had movie night recently with it outside, you know, in the yard. So we could use it that way. But there's another time we did a meeting and we couldn't. So we just ordered on Amazon a TV stand and a, like, a 60 inch TV. And then we just left it. Right? So it was that much cheaper. Left it behind, and it was cheaper than hiring from the AV in the hotel. Which, you know, like, if that's your business, if you're in that, like, AV business, might wanna consider.

13:08Dan Clifford: Yeah.

13:09Bill Gallagher: Leave it to these amateurs. They're lost. Right. That's right. Alright. So now, like, far in advance. So we got a location. Yep. And I, the indoor outdoor, I think, is really important. The views, windows. Some people are like, oh, it's distracting. No. It's also inspiring. It makes you feel good. Right? So I wanna feel great. The that off-site, the one on the private island, we went through several days of exercise and speakers and things like that. And then my wife and I just sat on the couch with this panoramic view of the Caribbean. We're looking across. We could see Necker Island just, you know, a mile away. And that's where we had our conversation about our future life. Like, fantastic. Right? Like, so open yourself up to that kind of thing. Don't just, like, burn through an agenda. Send people out on a walk, things like that. So we're getting into how you run the actual day. But you need a space that can allow for that kind of thing where people could step outside and move around and feel some air on their face, that kind of thing. Alright. Alright. So we've hit that one. Now, so next steps, I think, like, the design. What do you wanna accomplish? What kind of work you're gonna do? So now I wanna think about the end state. What am I gonna get out of it? Right? But do you have a different approach there?

Pre-meeting stage: gathering surveys, data, and using AI to synthesize

14:34Dan Clifford: Yeah. Really thinking what would make this meeting, this off-site a win. Yeah. People think of off-site as, oh my god. I'm taking myself away from work. But, really, you wanna make this so much more valuable that they, you know, that everyone understands, boy, getting away from work for a day or two is so worth it. So, really, yeah, thinking about that future state. What would make this a huge win? Like, twelve months from now, why would we think that that meeting was such a big win? What are the key things that we wanna accomplish?

15:02Bill Gallagher: So what are the key things that you think about? What are the the typical outcomes that people wanna walk away from a meeting? What's the end state?

15:10Dan Clifford: Well, for me, a lot of it is gelling the team and getting everyone on the same page. During day-to-day work, you're often just handling tactical things, and it's a couple people talking and someone else and there's an email. It's very tactical. You don't have everyone in a room at one place making decisions. And so it's really getting everyone on the same page about the big picture vision. It's a lot of things that go in the One-Page Strategic Plan that we might talk about, but really just nailing down things like the Big Hairy Audacious Goal, your three to five year plans, what's going on in your marketplace. What are the outside trends and opportunities and threats, things that are happening in your market? So really just getting the leadership team to talk about these things and hopefully on one page and really kind of gelling the big picture questions that guide the whole company. And if you can get on the same page about those, well then all the other decisions are a lot easier, especially for middle management and other folks. Those can ripple down later.

16:07Bill Gallagher: So you talked about strategy and alignment in there, and I think that it's a good question. Do you need to create and update your strategy, or do you need to just get alignment on it, or do you need to finish it and get alignment? Are the people that are going to be in the meeting, do you need their help to create the strategy, or do you just need to get them bought into it or to check it? I think those are good questions about the kind of work that you're going to end up doing. A lot of times I feel like strategy is not owned by everybody who's going to be in these meetings. They might have a voice to it and that kind of thing. So alignment is really critical, but sometimes you need to get some of the strategy work done before you're even in the room. It's your job often to think about what kind of company do I want in five or ten years, right? A little bit of that. What does it look like? That kind of thing, which you could do with some reflection, could do with your coach, you could do with a buddy brainstorming, that kind of thing. But I'm thinking here about the Big Hairy Audacious Goal. What is your big goal for ten plus years out? And what does it look like maybe five years from now? We call it Vivid Vision work, but what is that sort of rich picture of the future? I think those are really useful things to be aligned on, to have created probably before you get into the meeting. Sometimes they can be done in the meeting, but a lot of times I like to have that set before the meeting itself. So my focus is more on alignment and how do we get there.

17:42Dan Clifford: Yeah, I think, as we've maybe both done with an earlier stage company or company that hasn't established those, this is a great chance to get everyone on the same page with those. With a company that's already established a lot of those pieces, it's just a quick kind of check. Are we still here? Is this a BHAG? Are we still aligned on this? Are we moving forward on that? A quick story: a BHAG for the company that I ran was to be the most trusted user experience research firm in the world. And so we set that. So it's a big goal, be the best in the world, most trusted in the world. And we kind of looked at it for a couple years, and we looked and we generally worked towards it. And then one year in a strategy meeting, someone really brought it out and said, "Well, if we're going to be the best in the world, why do we only have an office in San Francisco?" And a light bulb went off for all of us. We're like, you're right. Like, we really are committed to this BHAG. It's not just something that goes on the wall. And it pushed us to think, alright, well, let's open another office. And it led to eventually opening a New York office and then having people more across the country. So it is something that you look at, and you think about, well, what are we doing to get there? And if we're not doing something to get there, is it wrong, or are we just not doing what we say we want to do? So that's another just great part about the annual strategy meeting as you think about these things and talk about them.

Surveying the entire team and understanding what motivates each person

19:05Bill Gallagher: Yeah. Getting clear and getting aligned on it is going to end up being in that meeting. So, and then it kind of leads us to who's actually in the room. So I do think you want to think about it. In my feeling, after we get above like eight people, it starts to really be unmanageable. If you've got seven, eight people in the room, you really should strongly have a facilitator helping you run the meeting. And then when you get beyond that, even a skilled facilitator could be challenged by having too many voices.

19:41Dan Clifford: What are your thoughts on the kind of people and who's in the room and the numbers and that kind of thing? Yeah, I mean, it can start, depending on the size of the company, can start a little smaller. But that is, I think, a sweet spot for a larger company, larger medium-sized company, six to eight people. Like, really, it is those key people. If you're the founder, it's the key people that you know are going to be around for a while and that are really driving the work in the company. I think it is important to avoid just having people in the room just because they might feel bad if they're not there. "Oh, we should really include everybody." I mean, I've definitely had that urge and had too many people in the room sometimes, and that's why the prework is important. So a lot of the prework can be done asking middle level management, other employees, doing surveys, getting all their feedback so it rolls right up into that meeting. So just because they're not at the table doesn't mean they're not getting a lot of input into it. And the facilitator, I find that super important. I know we're both facilitators, but when I was running a company, boy, to have to try to facilitate and make decisions and let the team do their thing, the most important part is I just love a facilitator lets people, lets the CEO almost just sit back and listen and let the team take a lot of responsibility for these ideas and decisions.

21:05Bill Gallagher: Well, I think, look. I had facilitators and coaches for years in my companies at various sizes, and I really appreciated them. And I sized it, and I used the people that I could afford that fit my budget that worked for the size of the team. And I was very thoughtful about who should be in the room versus whose input. So I might collect input from everybody, but I wouldn't necessarily have all the people in the room. I do have maybe two things I could share. So I have a client right now, and I will work with anywhere from 18 to 35 people. But we are doing the strategy in phone calls and Zoom sessions before the meeting.

21:49Bill Gallagher: And so our sessions with those 18 to 35 people is really about execution planning. So we did some strategy work recently with the group of 18, but that really takes a lot of finesse to do that. And now that company is growing really strong. It's valued at hundreds of millions now and will very soon be at a billion dollar valuation. And we're hiring a thousand people a year in that business. We've done that for a couple years in a row. So that's a different kind of business, a different stage. But I think even about another client I had a few years ago, they were successful. They grew. It was a tech space company in the fintech business, and it grew and was sold for a billion dollars. So fit that criteria of home run kind of business success. But the process was exceptionally painful. So I would say the coaching with them was difficult. The growth took more time because as the team grew, there was a mix of leaders, senior leaders, strategic advisors, and founders. And nobody wanted to be excused from the room. And the CEO who'd taken over from the founding CEO didn't have the confidence or the comfort to dismiss people from the meeting. So I'm trying to do this kind of work with 24 people in the room. And in this case, it's not just execution planning. There's strategy debate going on. We would take four times as long to do anything as you might take with a typical company. So people would do this. Hey, it's been said already, but I just want to reiterate. Like, oh, shut up. Well, just say, I vote for this and.

23:49Dan Clifford: Yeah. If everyone wants their airtime, you have 24 people in the room, it's just… And even attempts to sort of restructure it and they're going to…

23:59Bill Gallagher: I probably today, now, years later, I might be more skilled at managing that. But it took everything to to kind of pull that off. So think carefully about when we have three people in the room, five, six people look. I had another a company that went over a billion dollar value and $500 million revenue, and we had six. Right? So really tight. But there were a thousand people in the company. We just didn't want to put a hundred people in the room. So we would do all the core stuff with, like, six people, and then we'd invite maybe another 25 in on the second part of day two. So for a half day session to just say, execution plan this thing. Here's the direction of the company, guys. Now figure out how to do it. And so we bring them in, we brief them, then they'd run with it. Right? So that's when we have bigger teams. And that's not everybody here. Like, but think carefully even at a small team about getting some outside person in to facilitate to help you. Doesn't have to be us. It could be us. And we do have a thing. We want to encourage you to book with us or join our… So we have a group that meets, and then we also do private sessions. But we have a group in January 6th, 7th in California. You can come join us. It costs very little. You'll get all the work done pre, post, pre, during, post. All that stuff. It's a great way to go. So you can check us out at scalingcoach.com. And if you, or just find somebody in your local area. Right? We will have enough people there. It'll turn out for us. But if it's good for you, come join us. Right? If you like what we're saying. Alright. So now we're getting closer now. What's the prework to do getting ready for the actual session?

Setting expectations for laptops closed and phones away

25:49Dan Clifford: Yeah. I touched on that. It really is gathering input from everyone in the team. And for me, I like doing whether it's surveys or informal info about getting everybody to kind of roll up what's working for them, what's not working for them, what's fun for them, what's not fun for them, what are the main issues that they're seeing. That's kind of the qualitative feedback. And then also it's getting numbers together. So the annual meeting is a good chance just to make sure that all your KPIs and your numbers and your financials are all wrapped up by by the time you have your meetings. So you can look at those and reflect back and see, you at least spend a short amount of time on, like, alright. Let's see how we wrapped up the year, and then let's use that information to move forward. So yeah, it's a way also just to get folks in the entire company used to the idea that every year we're doing and, essentially, hopefully, quarter too, you're doing kind of some meetings that take everyone away from the from the day to day, the exact team from the day to day, and you're going to do some big thinking, and you're going to listen to everybody and get their input for…

26:57Bill Gallagher: Yeah. So I definitely love the idea of doing some surveys of some kind, and that's the probably the thing I use the most now. I used to send out, like, email or questionnaires, and I found that I couldn't track whether or not people had done their homework prep work. Some people will be like, oh, yeah. I'm going to look at that later, and then they'd look at it the night before, and we couldn't do stuff. But today, we can use some simple form surveys and AI to do a huge amount of prep work. So gathering all the facts. Look. If you're doing your annual meeting in December, January is most common, then you may not have final numbers even in January for the year, but you could estimate, you could project. So I want to get, like, the facts on the ground. What did we actually do? What were the numbers we put up? What's our profit, cash, revenue, whatever else. Other kinds of strategic metrics, like counting things towards your BHAG or whatever. I'd love to know and get an estimate of, like, we're going to finish the year like this. Right? And then I'd love to gather all the… Like, if we've done earlier strategy work, I want to pull that stuff together. It shouldn't just be in a file on your drive. I want to print it out. I want to get it maybe on some slides or things like that so that we could look at it together and go, is this relevant? Is this accurate? Is this still work for us? The whatever prior sort of strategy work and planning, I want to surface that stuff up. So wide survey. I think you're right. We could survey the entire employee base on what's going well, what are you proud of, the wins, the misses, what are we learning, what's hard, what's easy. These are a variety of things that we will look at in doing our annual planning business. Oh, my screen just changed in front of me. I'm looking at my screen now, like I still see you. Yeah. What… My… Say, my notes flipped up on me. So I think getting wide input, even beyond the people that are going to be in the meeting. The other thing that could be good, depending on the nature and size of your team, is have some conversations. Like, host a couple internal meetings where you just, like, talk about what do you feel good about. Like, the feelings are also important to get in addition to the facts. What do you feel good about? What do you feel bad about as we sit here right now getting ready to do all of that? So gathering your data, gathering your prior planning documents, surveying the team, starting some conversations around all of that. I think all that is really…

Designing the agenda from big-picture vision to tactical priorities

29:36Bill Gallagher: Really useful. Yep. As we start to lead up to the meeting itself, and let me share an AI hack with you. So I will do questionnaires for myself, for my clients, all that kind of thing, for the people in our cohort, for the annual, like people who just joined us one time. And then we will throw that into AI. And it doesn't really matter which tool you use. I'm using Claude more these days, probably mostly because my son's an AI researcher there now. But also because I like the conciseness of it and the language, the style of language output of it. But I've also used OpenAI, ChatGPT, a great deal in there. So you could use Gemini. You could use whatever tools you like. So I want to synthesize that into key insights. So instead of just reading all the survey data that we get back from the employees, I want to pull it together and say to AI, synthesize that for me. Give me a document that we can preread. Give me some slides I can put up as we go through the day. And so you could do all of that. There's some prompts and things like that that you might run, but it's not critical how you prompt it to get that stuff done.

30:53Bill Gallagher: Also, the strategy work that you might want to get done beforehand, like the vivid vision or things like that, all of that, we have AI prompts that we will send people through. But you could just say to your favorite AI tool, hey, I'd like you to interview me and work through all the elements of the Scaling Up Seven Strata, their SWT, and their vision summary documents. Right? If you just said that to AI and then had it walk you through things, spent like two hours on it, you'd have something interesting. Now I say something interesting because, you know, AI will give you some answers, whichever one you use. And you could even modify a little bit. You could say Scaling Up, these tools. You could name Seven Strata. You could name the vision summary, you could name the SWT as really useful. You could add to it. You could say in the style, in the way that Bill Gallagher does it. AI, I have spent enough talking out here that it'll adopt a little bit more, I don't know, an fluid intuitive style from my work and that kind of thing. So you could infuse it with that if that's important to you.

32:05Bill Gallagher: All of that will give you something. However, you can't just take that and run with that because there's no judgment. And if you click redo, it'll give you a new answer. So the things that come out of your AI tools are accelerants, helpers to synthesize, to summarize, to brainstorm, but they're not great decision tools. And in fact, if you throw an idea at it, hey, I'm thinking of starting a cannabis truck next to the schoolyard. What do you think? It'll be like, hey, that's a novel idea.

32:40Bill Gallagher: That's true. Right.

32:42Dan Clifford: Right.

32:45Bill Gallagher: AI will encourage you in some ways that are completely idiotic. So don't think that AI is going to replace your judgment or your help from a coach or facilitator or your forum that you're in. It is not. It is really, really powerful. Use it. We use it every day, almost every hour today in our coaching practice, but it is not a replacement for your critical thinking.

33:07Dan Clifford: Yeah. I mean, the summarizing is great. Right? If you survey, I don't know, 20 employees, 50 employees, you could summarize it, send it back to the employees. Like, here's the summary of what we heard. Is this true? And then maybe they can have departmental meetings to zone in on saying, yeah, oh, they captured it perfectly, or let's tweak this or that. So it does accelerate the process of getting the info that's the most important to each group and the company to the executive team, and then can really have a very productive strategy. So there's—

33:39Bill Gallagher: One thing that we haven't spoken about in this last prep, I think, that's really useful, maybe even early on. But I think it's really useful to start thinking about yourself and your team as human beings. So if you want your team to dig in and to do their best work both in the meeting and in the year ahead, it's really helpful if you'll think about why would they want to do this. What is the win for them? What are they dealing with in life? What are you dealing with in your life? How does this work for them in their life? What is it providing for them? And sometimes that alone, like, the hardest part is people. Right? People are crazy and illogical, and they drive us crazy except that we're people. We drive somebody else crazy in exactly the same way. Right? So starting to think about yourself and your people as real people and how does this all fit for them is a huge, can make a profound difference in the year.

34:37Dan Clifford: Mhmm. Absolutely. Even like sometimes we've used the question of just, why do you work here? Like, why do you like working here? And every year, you might get different answers, and every year things change, and you want to hold those roots, like the things that people really like about working there. You want to make sure you're not changing that too much as even as you're growing.

35:02Bill Gallagher: I had a guy once, a smaller business who eventually grew and sold. But and he was like, I don't know how to get more performance out of my people. I'm like, well, tell me about your people. Who are they? What are they dealing with? What do you want from them? Why does this matter to them? Why do they work here? He kind of had no idea. He's like, look, they work here because I pay them, and they can do the job. And I want to give them spiffs or whatever. Like, in his mind, the motivation was obvious and self-driven and inherent and, like, why not? But in reality, people get comfortable with things and they have different reasons, and they can't connect what they're doing to what they want in their life. Right? So I spent some time to get to know his people then over the next little bit, and I went back to him. And what I discovered that he didn't know until after we went through the process was that one of his team members was thinking about starting a family. Somebody else wanted to buy a house, their first house. Somebody else had never taken an international trip, like an international vacation. You know, there's a whole series of things like that that are possible, and that people are interested in and that connect to them that go beyond the day-to-day. Somebody wanted to go back and get their MBA and, you know, that kind of thing. How do you connect the job, the role, the team to people, start to think about people holistically?

36:31Bill Gallagher: Hey, somebody's got a—my son had to record a video as he joined the Anthropic team, and they're like, tell us about yourself. Right? So right top of that video featured prominently is his two-year-old. Right? Because a huge part of his life is his, is his two, almost three-year-old daughter. Right? So that's part of it. Think about your people and what's going to make the year ahead. And then also think about, so for this meeting, what's going to go well? How do we set it up right? As I was getting ready to do one of those meetings in the mountains a couple years ago, and the CEO and a couple of people were really excited about this mountain trip. But they didn't stop to think about it, and they didn't realize they had a lot of people on the team who were not confident drivers, didn't like or weren't comfortable driving in the snow.

37:21Bill Gallagher: And by the time everybody really thought about that, it was a little late to arrange, like, a shuttle bus or something to get them to the location. So people just kind of muddled through it, but it had a real impact on the team. And one person just was like, freaked out because the snow started to come down. They're like, I'm not driving in that. And that was that. So they didn't end up participating. So thinking about your people as holistic human beings with all kinds of quirks and personal beautiful things and odd things, it's really, really helpful. And then also acknowledging yourself. Like, look, what are your personal circumstances that are going to make the meeting easier, harder, like that? Right?

38:08Dan Clifford: Yeah. Key thing is the founder, ideally, in every meeting, you're finding a way for you to be less involved in the day to day. Right? You're growing yourself. And of course, if you grow yourself, then your team has to grow as well. But yeah, really thinking about in what way can I extract myself from some of the day to day so I can do more strategic thinking and work on culture and maybe land huge clients or other higher value work and allow others to take on more? So that's another question that I usually pose to CEOs.

38:41Bill Gallagher: Along that line, thinking about the people are coming into the meeting. Right? And they're used to a certain thing in their meetings. They're used to, like, leaving their phones on and their laptops on and being distractible and managing multiple things, both business and personal in the middle of other things, and that makes for terrible meetings. Right? In any week, but for sure in a critical meeting where you're investing time to come together like this. So setting people up that, look, for the most part, it's going to be laptops closed, phones away in this meeting, unless they're actually being used for the meeting or you get to a break. And even on a break, we'd rather have you, like, talking with the other people in the meeting than immediately, like, trying to handle something. So getting it set up so that your life and your business is set aside for a day or two so that you can really be in the meeting. Right? And we may use AI in the middle of a meeting. I was with the team yesterday. We were using AI nonstop to transcribe notes on the wall and the whiteboards, to do process descriptions, to ideate. Like, we're using it throughout. It wasn't like, oh, I'm going to go check my email and manage my other client in the middle of it. Right.

39:57Dan Clifford: Yeah. If one person's gone, any one person out of the meeting means you don't have the full team there, and you're not making joint decisions. You don't want someone to come back into the room and a decision was made and they don't agree with it, and it's just really, really tough to move forward from that. So it's interesting. We're almost forty minutes in now to this conversation and we're still not at the meeting itself. Right?

40:23Bill Gallagher: True. So much happens in the preparation lead up. The meeting will actually be kind of quick. So I think one more thing to say is just in advance, thinking about we talked about location and being able to get up. But what about, like, food? What about breaks? What about team dinner? What about things like that that are going to make it? So last minute preparations for a great, like, connected nurturing experience, make it fun, make it playful, that kind of thing. Right? Absolutely.

40:51Dan Clifford: Yep. Yeah. It's an annual opportunity to be a bit of a team builder. You're there to work, but also it can be a reward and a thank you to your top people for a good year or at least trying really hard on a year that was rough and just recognizing the work.

41:05Bill Gallagher: One of my teams played a round of golf. Another team, we were in Arizona at the right time of year, and they went to a spring training game. One or a preseason, I don't know what they did. Something in baseball, really. And so what can we do? Like, we took our groups in our small company cohort. We took them and taught them surfing. Right? I've taken them sailing on the bay. So we'll create some side play fun thing, a great dinner, or something like that as well. Yeah. Right? Alright. Let's talk agendas.

The pre-work: running through your calendar and photo stream to remember the year

41:46Dan Clifford: Talk broadly about your thoughts on the agenda. What does the day actually look like with a day or two days? What's the flow beginning to end in your view? Yeah. I tend to go from bigger picture to more detail. So bigger picture is just getting aligned on some of the big strategy questions. And then by the end, like, by the end of the meeting, you've got priorities decided. You've got people assigned to those priorities. You've got actions, at least the start of an action plan. So everything in between is really getting from here to there. It's, again, like, quickly reviewing the year, thinking about the goals that you want to set for the future, what's going on in your industry, what are the resources that we have? So what are the key things that we need to do to get us from where we are today to where we want to be a year from now? And where you want to be a year from now is based on where you say you want to be five years from now. So what do you have to do this year to get to where you want to be five years from now? So it's basically backing into your BHAG or your vivid vision. So for me, like, if I had to pick one tactical, one thing that's the most valuable, at least what it was for me and a lot of entrepreneurs, is you walk out of the meeting with three to five priorities, big things that you want to work towards in the year. And the priorities are the things that are outside the day to day business. Like, you're still going to bring in clients and revenue and do your day to day. But the priorities are these things that are, like, taking you from a state where you are now to where you want to be in the future.

43:19Bill Gallagher: Yeah. So I agree 100%. Big picture then to what comes next, really tactical. And big picture means long term. When we talk big picture, we're talking ten years, five years, one year, like, working back from the future. That's big picture. It's funny. Big picture is the long view. Right? But before even that, I like to start with some personal stuff. I like to start with some communication openers or team building. I like to start with good news. So I want to build some human connection and some playfulness before we get into that big picture stuff. And then I either want to put it out or work through the big picture stuff. So and really temporally, ten years out, so time based. Ten years out, then maybe five years out. And then when we get to one year, we're generally talking about we're now into the actual planning. Right? So the ten year and five year is about clarity and alignment for the most part, and are there aspects of strategy to clarify? Our SWOT, the SWOT tool, is a really useful thing to update that sort of bridges tactics and strategy. It says, look. What are we good at? What are we not good at? And what's happening in the world? Like, where should we lean into this year? Or how do we leverage the things that we're always good at, should be good at in this time, in this year? So it makes the long term strategy relevant to the what's going on in the near term. Right? And helps us to figure that out. So

44:58Bill Gallagher: Some personal opening, we might do exercises related to the CliftonStrengths. We might do personal wins, we might do general wins and that kind of thing. And then before we go into strategy, I think it's often useful to do the review. So if we've done our survey work, if we've done some AI summaries, we might want to just presence or talk up for a minute: what went well? What didn't go well? What are we learning? What's easy? What's hard? A variety of sort of retrospective-like things on either the prior quarter or the whole year.

45:37Dan Clifford: Yeah. No, it's like looking back and saying, did we hit our goals or not? Like, in certain KPIs, we tend to track weekly and then monthly and yearly. So do we hit our KPIs or not? And if not, why not? And what can we do in the future to change that? And so those might roll into the priorities that you choose at the coming up. You had also mentioned starting with some almost team building or core value stories or kind of more lighter personal subjects. And one thing that we've done together, which I find works well, is having a dinner the night before. So if everyone's flying in anyway, you've got people together, you have a dinner. It's a little bit talking and getting to know each other, but also that's a great time for thanking people, for getting those core value stories, for thinking a bit about what's going on in the industry.

46:27Bill Gallagher: So for that, if you're going to do some review over dinner, which I do love to do, you want to do that and they call it Jeffersonian style. So one speaker, everybody listens. We have a question like, what went well? What are you proud of? We go all around the table. What didn't go well? We go all around the table. What are you learning? What are you looking forward to? What are you grappling with? We go all around the table with these kinds of questions. And that is a great way to do it, like, over a dinner or like a working dinner. And you have to kind of manage the intrusiveness of the service and things like that if you're going to do that. But I do love to do that. We could start that the night before. And then, like, day two or if we did prior night kinds of things, you could talk, you could do shower thoughts. People can relate to that. Like, you can open with some shower thought sharing, right? There's lots of exercises in the Clifton Gallup Strengths tools that we will use that you could just, you could ask ChatGPT for what they are and run them yourself or have your facilitator run them with you. So there's a variety of things like just get us talking, connected, and then sort of present, like, of the whole thing. One of the things I noticed in this opening of it is that sometimes I'm really fixated on something, a recent win or very often, like, the awareness of a failure. Something I wanted to get done in the year that I didn't quite get done, and I'm focused on that piece that I'm missing the big picture of the year. So there's that. Oh, and I forgot to mention, as we talked about the preparation, one of their, like, personal hack that I think is really important, and I encourage our clients to do. But now as we're talking through it, it comes to me. I look through my business facts. I do the survey, that kind of thing. We talked about that. I also look week by week through my calendar, and it helps me to remember what actually happened in the year. What did I actually do this year? And on this year, I added, I had Claude look at my Google Calendar and tell me how many flights did I take and how many nights was I away from home and it did this summary, and I was like, wow. That was very sobering, but also empowering. So that review makes a difference. And then I also, so my calendar and my notes, and then I look through my photo stream. So, you know, pictures on our phone. I'll flip all the way back to January, and then I'll just flick through the pictures. And sometimes it'll be like, oh my god. That happened this year? I thought that was, like, two years ago. And maybe it's a sign of my age that I can't remember what the hell happened when. But I definitely noticed now, like, oh, I forgot that I did a thing. You know? I forgot that was in this year.

49:10Dan Clifford: Right? I've had the same experience where I feel like, boy, I just didn't get enough done and I didn't, you know, I could have done more. And when I look at the calendar and the photo stream, like, okay. Alright. I'm feeling a little better, but let's keep going for next year.

49:28Bill Gallagher: So then big picture, get aligned in those things. A lot of them, you just want to put them in the room, get them aligned, maybe update them. But I find from a timing standpoint, I could spend as little as fifteen minutes on an agenda item. And for things I need to work through, as a coach anyway, I can work through ideas in about forty-five minutes most of the time. It's rare that I even need to take an hour and a half for something. When you're planning for yourself, you might allow one to two hours because you're not facilitate, like, if you're not using a facilitator, each thing's going to take a lot longer because you're going to be wrangling the team. You're going to get lost down that wormhole, that diversion yourself.

Facilitating the session and using sticky notes with AI transcription

50:08Dan Clifford: Rabbit hole, wormhole, whatever it is. Right? You're going to go off on tangents. Definitely. Yeah. I think that's one of the key jobs of a facilitator, I think. And when it the one I value the most is like, okay. So we've decided that. Let's move on. Alright. Now we're going to go here. Let's let, you know, let's, you know, let me ask you about this piece that we can do. Let's move on. Yeah. Let's make sure we end on time. Yeah.

50:29Bill Gallagher: So I think those are the key things. And then, you know, our key mark, whether we're meeting online, so sometimes, well, some of our teams are meeting in Zoom still. I have some teams overseas that I meet with, and we do most of our work on Zoom, and we use tools like Mural still. But the rest of the team, we're meeting in person. And for those, we might have a conversation at a whiteboard. We might use some AI assisted, or we might go old school and write on sticky notes, or we might do a combination of things. The team I was working with yesterday, we had prework, we had slides from AI, and then we also did sticky note work in the room. In particular, we were working on, like, what should our process be for this? What should our process be for opening a new location? What should our process be for hiring people? What should our process be for onboard? So we did various process. We did them with sticky notes, and then we used AI to transcribe them, organize them, edit them into a standard thing, to suggest industry improvements. So, like, how would competitor A and B do this thing, and what are we missing? Right? So it'll give us ideas like that. Yeah. It's a great example of just taking things from the strategy level.

51:40Dan Clifford: And then moving towards actual implementable, you know, action plans that—

51:47Dan Clifford: That leave the meeting. Because a lot of companies will do these strategy sessions. It's almost a separate thing they kind of forget about. The moment they get back to the office, they're back to the day-to-day, and they almost forget about half the things they did in the meeting. But if you come up with an action plan and if you come up with a person responsible for each priority that you've established with, maybe we're getting into sort of what happens after the meeting. But I like to make sure that the companies have follow-up meetings afterwards where you're getting back together to say, okay, for each person that's responsible for each priority, what is the thirteen-week action plan for this quarter to get there? Right? So that's where you have that translation from the big picture to we are actually moving forward on these things on a weekly basis.

Closing the meeting on a high note and creating a theme for the year

52:28Bill Gallagher: Yeah. And AI is a really helpful tool to this today. You're gonna do something you've never done before. Hey, Dan's gonna launch our website. He's never done that before. Great. Just ask ChatGPT, give me a thirteen-week plan to create and launch a website. Tell me what to do. And I don't have this, I have that, I have, and AI will walk you through it. And then you'd be like, oh, I don't know what happens there in week three. Tell me how do I do that? And it can give you more details. So you can use AI as a planning tool as you kind of ramp out a meeting. Let's talk about closing the meeting and then we'll get into what's after and we'll close this conversation before we run too long. But I think we're giving people a lot of things to think about here. I think two things are really important closing the meeting. One of them is don't take on too much. So that's where it's useful with each other and with a coach to ask yourself, are we stepping up? Is this like, should we be a little more modest in what we take on in the year? It's the first thing I think of. And then the second thing is I want to end on a high note. Whatever we've done, I want to be proud of myself and my team for what we accomplished in the meeting, wherever we got to. Right? And I want to finish on a positive note feeling like we did some good work. Right?

53:47Dan Clifford: Am I missing something there in the close? No, absolutely. Again, it's a chance to thank everybody. The people should feel proud and very good about this process. Sometimes it's the first time folks have worked at a company that actually takes the time to really go offsite and think strategy, and I've seen a lot of employees just almost be blown away and appreciative that this much thought and effort goes into thinking about where the company's gonna go and the fact that their opinions are so valued. So absolutely, something I know you do sometimes, it depends on the meetings. Maybe create a theme for the year. So you've come up with all this, and then you might have a fun theme that you can name and brand and share with the whole team. So that's another way to kind of end on a high note and make it interesting and exciting for the employees that are soon gonna hear what decisions were made.

54:36Bill Gallagher: Yeah. It's really encapsulating the work to be done with a theme or rallying cry for yourself and everyone else can be really a useful way to end. And then just gratitude. Like, great work, guys. Appreciate all your thinking and effort. And generally, I think by four, 4:30 in the day, if we start at 8:30 or nine, people's brains are kind of toast from this kind of work, and you can't get a lot. It's time to go have a drink or go to dinner or do whatever you do in your thing and break the meeting. So the worst thing that happens after a meeting like this is you do great things and then you produce a conference report and you have action plans and then they sit in a binder somewhere or on your computer hard drive and that's the end of that in the cloud. That's the very worst thing because then you will actually still get some benefit. You will unconsciously move towards them having done that. But the work will be mitigated and diminished by your lack of follow-through. Right? So I think the key thing in my view is we want to take all the outputs of that meeting, the action items, the plans, that kind of thing, and then we want to figure out how to keep those front and center over time. And usually, that's some kind of a dashboard, some kind of a visible plan, and bringing them into a weekly meeting. If we look at those priorities, the output of the annual strategy session every week, and we just move things beyond the day-to-day of your regular production side of aspects of your job, a little bit every week, you'll greatly move the company forward. Right? So a weekly look and a little bit of weekly extra work, massive.

After the meeting: weekly review and thirteen-week action plans

56:23Dan Clifford: Yep. Absolutely. That's why we're creating that thirteen-week plan so that for all those future, every week on, for those thirteen weeks, it's part of that weekly plan where you're checking back. So how are we on the strategic priority? And hopefully, every week, you're making progress. And with clients, I've often even used the red, yellow, green like you would with any other KPI. Are we on track? Are we a little off? Are we like, all hands on deck? What do we need to do to get it back on track? So we're kind of looking at those priorities every week. And really, it can just take ten minutes per meeting if things are going well, maybe a little longer if it's not, but it shows your entire team that you are serious about implementing these big picture strategy decisions that you've come up with in your annual meeting.

57:08Bill Gallagher: So yeah, I think that's really critical. We just want to get in there, we want to look at it regularly. And while we're looking at it, we're updating the strategy. We're looking at the whole year. We're only actually detail planning the quarter because somewhere around March, April, we are gonna plan the next quarter. So somewhere at the end of March, beginning of April, we're gonna stop. We're gonna say, okay, we did that in the first quarter. Now what happens? So those could be half a day to a day long with really, like, a sophisticated, highly funded team. We might do two-day quarters, but mostly it's half day to a day. And then we're gonna update the plan. We're gonna say, okay, next quarter. Like, how do we do this quarter? Great. What's the next quarter? So that's a much more tactical kind of planning meeting that happens for the rest of the quarters of the year after that strategy session. So don't try to plan out what's gonna happen quarters two, three, four. You could speculate a little bit, but give yourself a break because what happens in quarter one won't be exactly what you intended, designed. It'll show up differently for sure every time. You know, even absent some major world event or industry event, like, things will just break differently than you plan them to, and so you want to reset, plan another thirteen weeks. I think that's the main thing. Right? Like so let's gather all the artifacts. Now we'll create a conference report, and we will use Otter or Zoom Meeting to create some notes and transcripts and help pull it out. But then we'll have an assistant.

58:42Bill Gallagher: The main one who does for us is Wanda in our world, and we'll have somebody review that and edit that down. We'll include all those stuff we did on the wall, and we'll pull that stuff all together in one kind of consolidated thing, which we'll use a little bit in those weekly meetings, but then we'll use it a lot in planning the next one. So before I go and plan and do quarter two with somebody, I look at what we did for the annual and quarter one, and then we'll update from there. So we're creating some artifacts that we can refer to in those weekly meetings.

59:16Dan Clifford: Yeah, and again, another great use of AI is just you can just have all these ideas and you have it summarized and you've got it in a format that you can use.

59:25Bill Gallagher: Pull it out really quickly. You do have to check it because it'll hear things wrong. My wife and I walked through this process at our thing on the private island, and we're sitting on the couch looking at this big view, and we just had Otter going. And Otter captured the transcript. We said, okay, Otter, distill it down into this thing with this. We took the Otter transcript and we put that into Claude. We said, okay, distill this down. Actually, in our case, I did it to Claude and Lori did it to ChatGPT, and then we merged the two because it did a little different style. We merged the two and we created, now we have our, you know, our plan as a couple, which includes our business, and the whole thing is really, really useful.

1:00:08Bill Gallagher: Great. Alright. Well, that's kind of it. Look, if we can help you, we've got a group meeting in January. You can come join us, do your annual planning strategy work with us. We'll get it done in a day and a half because we'll give you some prep work and some post work. It'll be in California locations, that kind of thing. It's very inexpensive. You come join us. You could also book us to do a private session if our time's available for you. It's certainly cheaper if you come here and do it in California with us. We have lovely places. So all that, scalingcoach.com, or you could send an email to bill@scalingcoach.com or info@scalingcoach.com, and we can get you set up and join you in that group session. That kind of thing would be really great. We'll be at a waterfront location. We'll have walks outside. We'll have a break in there. We won't be in a windowless room. We will take our own advice. We'll give you a great start to the year ahead. And if you want to do one of those super big expansive things where you plan out your life on a private island, send me a note. I'll help you get set up with one of those too. We can do that. There's a way to get you in one of those if you want to do that kind of thing. I also do mini versions of that. Like, midyear, I'll do sailing on the San Francisco Bay with CEOs, and we'll go and we'll talk and we'll change the setting up. We'll go sailing. We'll talk through this. So we've got a variety of kinds of things we could do. If we can help you, let us know. info@scalingcoach.com, scalingcoach.com.

1:01:38Dan Clifford: Dan, anything else to say about all that? No, that's great. I think the key, I think the key to reducing stress in your life if you're a founder or CEO listening, like, really, if there's one thing you can do, it's setting these quarterly meetings and then the annual meeting that lets you really just offload a lot of the thinking and the buy-in to your team. And they want it. They're very excited to take on more typically and to have a bigger say.

1:02:06Bill Gallagher: So I found personally in my life that that was a big turnaround for me where I felt like I was on a treadmill to, like, feeling like, wow, I think I'm a CEO now. I can actually think about the business a lot more. So it doesn't have to be so hard. You don't have to be so busy. A little bit of busy is fine enough. Make it easy for yourself. If we can help you, let us know. There's our whole recipe. There's all of our thinking on it, like decades of wisdom from doing this kind of work. Hopefully that's helpful. It gives you something to think about. Thanks to Anna and to Wanda for producing our show, getting things ready in and out every week. Thanks to my friend and mentor Verne Harnish who created this whole Scaling Up method that I'm part of, and it's helped so many companies grow. And thanks again to all of you for watching, for listening. Share the show with somebody else. Like, subscribe, download, you know, do all that stuff. Turn on your notifications. You know what to do. Show us some love and we'll keep bringing the shows to you. Until next time, keep scaling.

1:03:08Bill Gallagher: Thanks for listening today. One last thing. If anything in this episode hit home, my book digs into it further. Busy Is Broken: Do Less, Scale More. It's all about how to stop drowning in work and build a business and a team that scales without you. Available right now with content samples at busyisbroken.com. Go grab it. Be less busy.