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

Foreign. 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, Everybody. Bill Gallagher, scaling coach and host of this super fine show, Scaling Up Business Podcast. Our show comes to you every week now, I don't know, 650 plus episodes. Everything to do with growing, scaling your company. And we do addition to the show. We put on workshops, we have coaching programs, we have cohorts you can join, things like, like that. So check out everything we got@scalingcoach.com and if anything in this show strikes a note with you, just send email to info scalingcoach.com or just go to the website and click a link and talk to us and like that kind of thing, see if we can help you. All right. All right. So Dan Clifford joins me. Dan, welcome to the show. Thanks.

Yeah, great to be here.

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, we now do quite a bit of coaching work together. And Dan lives actually right nearby me, not far away and is involved with our group and that kind of thing. So lots of experience, Dan across industries, particular 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.

All right, great. Can't wait to talk about.

We thought we just talked about everything 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 like, first step? Where do you go to like if you're going to set up for your company for a client what's first?

Yep. Well, the first, 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, and have a day. But really I think the important work is, is like the, the work that leads up to it almost like, like you and I, we've done triathlons before, Bill.

I know.

Yeah, like often it's like the training, all the stuff you do leading up to it is like where all the important work happens. So first thing is, I think, get the meetings in the calendar and then set a schedule leading up to it, like, you know, even a month in advance with some to do items and we'll, we'll talk about some of those. What's your, what's your favorite?

Well, I think, 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. They have their spouses have expectations of them. They're like, oh wait, I can't go away that day because I've got this or that or like 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, like where we're going to end up with 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? 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?

Yeah.

So location for me is like 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, like, and I'll share a couple of them. But what for you, Dan, is the. What constitutes a great location?

Yeah, yeah. I think when people call it an off site. Really. Yeah. It's like off site is good. Get away from your normal day to day and even just changing the environment, something that can feel you know, if you can afford it and you know, whatever you can do but like something that's maybe, you know, 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 but you're using the whiteboard and you're getting up and moving around. If you're having a multi day event, you know, have a, have a place where that's a good health 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.

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, so we do have a bunch of them for private clients and also for our small companies in our group program. And, and we'll tend to use waterfront locations. Right. I also have done mountains in the Jane 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 farming. So we have a mountain hotel that we use more than any other place up in Lake Tahoe 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, I got back from a multi day sort of 10 year planning, 5, 10 year planning for our lives for a bunch of entrepreneurs, a of bunch, 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, I know there's place in Santa Fe there. 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 or just find a place with a great view. But you said also like the location. So I mean the size of the room, if the room, if you have eight people or six people and then you Get a six or eight person conference room. It's not going to be great. It's going to be tough. Right. So in general, double it. So if you have a group of, 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 want to be in business or maybe even live another day, it's a interior room at a major hotel chain, right?

That's right. I'll throw out to an alternative to just to rent it. You know, if, 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. Like just find a place that's off site so that when you're on site, you know, employees are there, you're going to look at everything, you're going to look at all the things that need to be done and you don't want that. You want to be away from your, your company now, however you can get that done.

Yeah. So great budget hack ideas, right? You don't have to spend a lot of money to do this and spend. If you have money to spend, spend it on the kinds of things. So if you want to travel, that kind of thing, great. We did a kind of a launch off site a couple days in Mexico a couple of years ago. But that was for a company that you know, we knew was going to 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 your 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 has been courting you, or a VC firm or a bank even. We used to use a bank conference room in downtown San Francisco. It was really beautiful conference room right in 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. Often you can use those free again for the most part. Well, I guess you pay the law firm over time, right? So they're counting on there. So 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 going to have a real cool car themed room or into some regional kind of thing. You might find that they are really cheap. They don't book them out a lot. So museums can be a fantastic place to get an inexpensive conference room that is also kind of creative and cool in some way. And then if it's midweek, which it usually is, for this kind of meeting, you can arrange like a private tour of the museum at the end of the day or whenever. Right. So that's another one that 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, 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. Right.

That's what people think of first.

So it's good.

Yeah, we're talking about some of the, the other things that you can do.

We did one at, there's a, there's a hotel, you know, a couple 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, from that conference room. But like, really is it? And then, you know, the AV is going to cost you two grand and that's all terrible. Oh, here's another funny hack with the logistics of location. So I do boot camps a couple times a year with Vern Harnish. And, and we were griping about the AV cost in the thing when we're trying to set it up. And you know, we want to make a little money on it as well and not have it be a funny losing thing. And so it was 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, 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. 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, you might want to consider, just leave, leaving TVs around. All right, so now like far in advance. So we got a location.

Yeah.

And, 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 want to feel great. That that off site I did on the private island. We went through several days of exercise and speakers and things like that. And, and then my wife and I just sat on the couch with this panoramic view of the Caribbean. We were looking across, we could see Necker island just a mile away. And that's where we had our conversation about our future life. Fantastic. So open yourself up to that kind of thing. Don't just 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. All right, so we've hit that one into so now what? So next steps, I think like the design. What do you want to accomplish? What kind of work you're going to do? So now I want to think about the end state. What am I going to get out of it? Right. Do you have a different approach there after.

Oh, absolutely. I mean, yeah, yeah. Really thinking what would make this, this meeting, this off site, a win. People think of offside as, oh my God, I'm taking myself away from work. But really you want to 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. Think about that future state. What would make this a huge win, like 12 months from now? Why would we think that that meeting was such a big win? What are the key things that we want to accomplish?

So what are the key things that you think about? What are the typical outcomes that people want to walk away from meeting? What's the end state?

Well, for me, you know, a lot of it is like gelling the team and getting everyone on the same page. And 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. You know, it's very tactical and you don't have everyone in a room at one place make decisions. And so it's really getting everyone on the same page about the, 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 like those can ripple down later.

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 gonna be in the meeting, do you need their help to create the strateg or do you just need to like 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. Like it's your, it's your job often to think about what kind of a company do I want in five or 10 years, right? Yeah, yeah, a little bit of that. What does it look like? That kind of thing, which you could do with some reflection, you could do with your coach, you could do with a buddy, foreign mate, that kind of thing. But I'm thinking here about the big hairy audacious goal. What is your big goal for, you know, 10 plus years out and what does it look like maybe five years from now? Like a, 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 time. I like to have that set before the meeting itself. So my focus is more on alignment and how do we get there.

Yep. Yeah, I think, you know, as you probably we 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? You know, is this still 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 that's a big goal, you know, be the best in the world, most trusted in the world. And we kind of looked at it for a couple of 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 know, you're right, like that. We really are committed to this bhag. It's not just something that goes on the wall. And it pushed us to think, all right, well, let's open another office. And it led to, you know, eventually opening a New York office and then, you know, more, you know, having people more, you know, more across the country. So it is something that's a lot. You look at, you look at it and you, 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, you know, not. 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, 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, like, who's actually in the room. So I do think you want to think about it in my feeling. And after we get above like 8 people, it starts to really be, like, 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 to do. What are your thoughts on the kind of people and who's in the room and the numbers and that kind of thing.

Yeah, definitely. I mean it can start, you know, depending on the size of the company it can start a little smaller. But I, that is I think a sweet spot for a larger company, larger medium sized company, you know, 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 to. They might, because they might feel bad if they're not there. Oh we should really include everybody. I mean it's definitely. I've had that urge and had, had too many people in the room sometimes and, and, and, and that's why the pre work is important. So you know a lot of the pre work can be done asking you know, middle level management, other employees doing surveys, getting all their feedback. So it rolls right up into that, into that meeting. So you, you know, just because they're not at the table doesn't mean they're not getting a lot of input into it. So yeah, and the facilitator, I boy I find that super important just for, I know we're both facilitators but when I what like 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, these ideas and decisions.

Well I think look, I had facilitate facilitators and coaches for years in my companies at various sizes and I really appreciated them and I, 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 like, like anywhere from 18 to 35 people. But we are doing the strategy in phone calls and zoom sessions before the meeting. And so our sessions with those 18 to 35 people is really about execution planning. So there's we, we did some strategy work recently with the group of 18 but that really takes a lot of finesse to do that. And I, and now that company is growing really strong is Is 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 of 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. Was a tech space company in the fintech business and it grew and was sold for a billion dollars. Right. So fit that criteria of, you know, 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, 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, I don't know, 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, 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 just people would do this. Hey, it's been said already, but I just want to reiterate like, oh, shut up. We'll just say I vote for this.

Yeah, if everyone wants their air time. If you have 24 people in the room, it's just, it's just.

And even attempts to sort of restructure it and they're gonna think I pro today. Now, years later, I might be more skilled at managing that. But it like took everything 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 company that went over a billion dollar value and a 500 million dollar 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 run with it. Right. So that's when we have bigger teams. That's not everybody here. But think carefully, even at a small team about getting some outside person in to facilitate, to help you. It 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 1-6-7 in California. You can come join us. It costs very little. You'll get all the work done pre post, you know, pre during post, all that stuff. It's a great way to go. So you can check us out 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. All right, so now we're getting closer. Now what's the pre work to do? Getting ready for the actual session.

Yeah, I touched on that. It's a bit about. I think 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 this, 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 meeting so you can look at those and reflect back and see, you know, at least spend a short amount of time on like all right, let's see how we wrapped up the year and then let's use that information to, 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 you know, essentially hopefully every quarter to, 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 it.

Yeah, so I definitely love the idea of doing some surveys of some kind and that's 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 would be like, oh, yeah, I'm going to look at that later. And then they 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, 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? 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, in doing our annual planning business. Oh, my screen just changed in front of me. I'm looking at my screen like, I still see you. Yeah, yeah. What? My second. 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 of 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, you know, 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, really useful as we start to lead up to the meeting itself. 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 people who just join 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 AI researcher there now, but. 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, from the employees, I want to pull it together and say to AI, synthesize that for me. Give me a document that we can pre read, give me some slides I can put up as we go through the day. And so you could do all of that. There are some prompts and things like that that you might run, but it's not critical how you prompt it to get that stuff done. 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 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. 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, 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, and 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, fluid intuitive style from my work and that kind of thing. So you could infuse it with that if that's important to you. 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, are helpers to synthesize, to summarize, to brainstorm, but they are 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, Right? 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 form, that kind of thing. 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.

Yeah, I mean, the summarizing is great, right?

If you get.

If you survey 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 a meet, you know, departmental meeting, meetings to, like, zone in on, say, yeah, oh, it captured it perfectly. Or let's tweak this or that. So it does accelerate the process of, like, getting the info that's the most important to each group in the company, to the executive team, and then they can, like, really have a very productive strategy.

So there's 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, that for them in their life? What is it providing for them? And sometimes that alone, the hardest part is people, right? People are crazy and illogical, and we. 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.

Absolutely. Even, like, we've used the question of just what, you know, why you're. Why do you work here? Like, why do you. 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 even as you're growing.

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 him spiffs or whatever like his. In his mind the motivation was obvious and self driven and inherent and like why not? But in reality, people get comfortable with things, 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, 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 prominent is this 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. And by the time everybody really thought about that, it was a little late to arrange like you know, 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 just was like freaked out because the snow started to come down there. Like I'm not driving in that, you know, and that was that. Right. So they didn't end up participating. So thinking about your people as holistic human beings with, with you know, all kinds of quirks and personal beautiful things and, and odd things and. Right. Is really, really helpful. And then also acknowledging like yourself, like look, what, what are your personal circumstances are going to make the meeting easy or hard or like that. Yeah.

Key thing is the founder, you're like ideally in every meeting you're finding a way for you to be less involved in the day to day. Right. You're, 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, you know, extract myself from some of the day to day so I can do more strategic thinking and work in culture and maybe land huge clients and other higher value work and allow others to take on more. So that's another question that I usually.

Pose to CEOs meeting along that line, thinking about the kind of 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 in the meeting or you get to a break and in, 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 using, I was with a 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. But it wasn't like, oh, I'm going to go check my email and manage my other client in the middle of the day, right?

Yeah. If one person's gone, like any one person out of the meeting means you don't have the full team there and you're not making true joint decisions. You don't want someone to come back into the room and decision was made and they don't agree with it. And it just, it's just really, really tough to move forward from that.

So it's interesting, we're, we're almost 40 minutes in now to this conversation and we, and we're still not at the meeting itself. Right. Truth. 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 it 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 that so last minute preparations for, you know, a great like connected, nurturing experience. Make it fun, make it playful, that kind of thing. Right?

Absolutely. Yeah, yeah. It's a 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, you know, for, for a good year or at least try really hard on a year that was rough and you know, just, just recognizing the work.

One of my teams played around a golf. Another team was, we were in, in Arizona at the right time of year and they went to a spring training game one or a preseason pro. I don't know what they did. Something baseball related. And so what could 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.

All right, let's talk agendas. 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, you know, sort of 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 action, you know, 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 key and then it's, you know, what are the resources that we have. So what, you know, 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, so it's basically backing into your bhag or your, you know, your, your vision, your vivid vision. So you know, for me, like if I had to pick one tactical, you know, 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 for 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.

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 10 years, five years, one year, like working back from the future. That's big picture. It's funny, big picture is long. Long, 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 it's. And really temporally 10 years out. So time based, 10 years out, then maybe five years out. And then we often have some work to do at figuring out. Like when we get to one year, we're generally talking about we're now into the actual planning. Right. So the 10 year and 5 year is about clarity and alignment for the most part. And are there aspects of strategy to clarify our swt? The sweat 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 what 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 what's going on in the near term. Right. And helps us to figure that out. So 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? You know, a variety of sort of retrospective, like things on either the prior quarter or the whole year in review. Right.

Yeah. It's like looking, looking back and saying, did we hit our goals or not? Like in certain KPIs, we, 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, to change that? And so, you know, those might roll into the priorities that you choose at the coming out. You'd also mentioned starting with some almost, you know, team building or core value stories or kind of, you know, more lighter personal subjects. And one thing that we've done together which, 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, you know, talking and getting to know each other, but also that's a great time for thinking people forgetting those core value stories for thinking of, you know, a bit about what's going on in the industry.

Yeah. So for that you want to. So if you're going to do some review over dinner, which I do love to do, you want to do that. And they, I think 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, like a working dinner, 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 can 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 Gallop strengths tools that we will use. You could just, you could ask Chad GPT 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 aware 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, 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 other like, like personal hack that I think is really important and I encourage our clients to do it. But now as we're talking through it, it comes to me. I, 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 I, 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 like did this summer and it was like, wow, that was very sobering but also empowering. So that review makes a difference. And then I also saw 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 they may 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, but I definitely notice now, like, oh, I forget that I did a thing, you know, I forget that was in this year. 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 then when I look at the calendar and the photo stream, like, okay, all right, I'm feeling a little better, but let's keep, let's keep going for next year.

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 15 minutes on an agenda item. And for things I need to work through as a coach anyway, I can work through ideas in about 45 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 facilitating. 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. That diversion yourself, rabbit hole, wormhole, whatever it is. Right. You're gonna. You're gonna go off on tangents.

Definitely. Yeah. That's one of the key jobs of a facilitator, I think. And when the one, the one I value the most is like, okay, so we've decided that let's move on. All right, now we're gonna go here. Let's, you know, let's, you know, we ask you about, you know, this piece over here.

Let's move on.

Let's make sure we end on time. Yeah, yeah.

So I think those are the, like, key things. And then, you know, a key mark whether we're meeting online. So sometimes with some of our teams, we're 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 pre work. We had slides from AI and then we also did sticky note work in the room. In particular, we were working on, like, what's. What should our process be for? 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 processes. We did them with sticky notes and then we used AI to transcribe them, organize them, edit them into a standard thing, and then 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 and then moving towards actual implementable, you know, action plans that, that, you know, that leave the meeting. Because a lot of companies will do these strategy sessions and it's almost a separate thing and 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 out with a person responsible for each priority that you've established with follow up, maybe we're getting into sort of like 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 13 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.

Yeah. And AI is a really helpful tool to this. Today you're going to do something you've never done before. Hey, Dan's going to launch our website. He's never done that before. Great. Just ask Chat GPT. Give me a 13 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 just an 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, so you can use AI as a planning tool as you, as you kind of ramp out of the meeting. Let's talk about closing the meeting and, and, and then, 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 is 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, so I'm missing something there in the close.

No, absolutely. Again, it's a chance to thank everybody. People should be 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 off site 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 going to go and the fact that they're to going. 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 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 going to hear what decisions were made.

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 as you. And then just gratitude like great work guys. Appreciate all your thinking and effort. And generally I think by 4, 4:30 in the day, if we started at 8:30 or 9, 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 there is. You will actually still get some benefit. You will unconsciously move towards them having done that, but the, 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 sided aspects of your job A little bit every week. You'll greatly move the company forward. Right, so a weekly look and a week, a little bit of weekly extra work. Massive.

Yep, absolutely. That's why we're creating that 13 week plan so that for all those future four every week on the, for those 13 weeks, it's part of that weekly plan where you're asking, you're checking back, so how are we on this 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 of are we on track or are we, you know, a little off? Or 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 take 10 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, these big picture strategy decisions that you come up with in your, in your annual meeting.

So yeah, I think that's really critical. We just, we want to get in there, we want to look at it regular. And while we're looking at the, we're updating strategy, we're looking at the whole year. We're only actually detail planning the quarter because in somewhere around March, April, we are going to plan the next quarter. So somewhere at the end of March, beginning of April, we're going to stop, we're going to 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, and we're going to update the plan, we're going to 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, you don't try to plan out what's going to happen. Quarters 2, 3, 4, you could speculate a little bit, but. But I. 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 13 weeks. I think that's the main thing. Right. Like, so let's gather all the artifacts. Now we, we will create a conference report and, 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. The main one who does for us is Wanda in our world. And, and we'll have somebody review that and edit that down. We'll include all the stuff we did on the wall and, 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, and then we'll update from there. So we're creating some artifacts that we can refer to in those weekly meetings?

Yeah, absolutely. Yeah. 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. Pull it out really quickly.

You do have to check it because it'll hear things wrong and it'll do 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 and we said, okay, distill this down. Actually, in our case, I did it it to Claude and Lori did it to ChatGPT and then we merged the two because it did a little different style than we merged to and we created. Now we have our. You know, our one year plan is couple, which includes our business. And the whole thing is really, really useful. Right. All right, 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 and 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. York. 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. And we have lovely places. So all that scalingcoach.com or you can send an email to bill@scalingcoach.com or info scalingcoach.com and we can get you set up and, and join you in that, that group session and that kind of thing. Be really great. We'll be at a waterfront location. We'll have walks outside.

We'll be in a windowless room.

We will take our own advice. We'll give you a great. And if you want to do one of those super big expansive things where you plan out your life at a, on a private island, that kind of thing, send me a note. I'll help you get set up with one of those too. We can, we have that. There's a, 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 mid year. I'll do sailing on the San Francisco Bay with CEOs and we'll go and we'll talk and, and we'll change the setting up. We'll go sailing, we'll talk through it. So we've got a variety of kinds of things we could do. If you, if we can help you, let us know. Infoscalingcoach.com scalingcoach.com that's the thing. Dan, anything else to say about all that?

No, this is great. No, I think it's really 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, the thinking and the buy in to your, to your team and, and they want it, they, they're very excited to, to take on more typically and to have a bigger say. So I found personally in my life that that's was a big turnaround for me where I felt like I was on it treadmill to like feeling like wow, I think I'm a CEO now. I can actually think about the business a lot more.

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 Vern Harnish who created this whole scaling up mess. 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.