How to Facilitate an Annual Planning Retreat
Watch/Listen here or on Apple Podcast, Spotify, or wherever you listen to your podcasts“I believe as the leadership team goes, so goes the rest of the company. So if you don't have that consistent and significant sustainable growth, you've got some work to do.” — Mike Goldman
“We need a 90-day plan because that's where we're going to take real action.”
–Mike Goldman
The Importance of Annual Planning Retreats
They are essential for aligning leadership teams on priorities, fostering team collaboration, and setting the stage for the upcoming year.
Common Pitfalls
Many leadership teams either skip the annual retreat or conduct insufficient, short sessions that fail to address critical issues.
Objectives of the Annual Planning Retreat
Alignment: Ensuring the leadership team is on the same page regarding company priorities.
Focus: Concentrating on the most important goals, rather than diluting efforts across too many objectives.
Team Building: Enhancing team cohesion through extended collaboration and open discussions.
Pre-Work and Preparation
Pre-Work: Involves surveys, SWOT analysis, and leadership assessments to gather insights and prepare leaders for strategic thinking.
Choosing the Right Location: Conducting the retreat offsite helps minimize distractions and encourages creative thinking.
Facilitation Tips
Role of the CEO: CEOs should participate in discussions rather than facilitate, allowing an external facilitator to manage the agenda and ensure all voices are heard.
Inclusivity: Use tools like flip charts and post-it notes to ensure everyone, including quieter members, can contribute.
Crafting the Agenda
Key Agenda Items:
Bright Spots: Begin with positive reflections from the past year to set a constructive tone.
Lessons Learned: Review successes and failures to inform future actions.
Pulse Check: Gauge the team's current sentiments and identify pressing issues or opportunities.
Vision and Strategy: Reaffirm long-term goals (BHAG) and establish a three-year highly achievable goal (3HAG).
People and Culture: Assess the organization’s core values, structure, and talent to ensure alignment with the company's goals.
Discussion Topics: Prioritize issues and opportunities identified during the pulse check.
Annual and Quarterly Plans: Define financial and non-financial targets, along with key priorities (Rocks) for the year and upcoming quarter.
Wrapping Up
Cascading Communication: Clarify what information should be communicated throughout the organization and what should remain confidential.
Final Reflections: End with a group reflection on the retreat’s most important takeaways and overall sentiment.
Thanks for listening!
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One of the most important things a leadership team needs to get right is their rhythm of meetings together. Everything from one on one meetings with their direct reports to daily huddles, to ad hoc meetings,to discuss issues or opportunities to, what I call weekly accountability meetings, monthly check in and education sessions, quarterly planning meetings.
and the annual planning retreat.
And on this episode, I want to focus on the annual planning retreat. It is such an important part of this, what I call the planning and communication rhythm, such an important part and, leaders typically screw it up. and if you, if you feel like you get it right, beautiful, listen on, I'm sure you'll hear some ways to improve it.
But what I see very often is number one, frankly, leadership teams that don't even do an annual planning meeting. Not that they don't do it the way I recommend to do it, but they don't do it at all. Maybe the CEO sits in his or her office, comes up with priorities for the year, has a vision in her head, and it's communicated on an as needed basis.
to the members of the leadership team. I've also seen leaders that say, of course we do an annual planning meeting. in fact, we've got it, you know, coming up on Friday, we're going to spend two hours going through our annual plan. You cannot possibly discuss the things you need to discuss, build the team the way you need to build the team, make the decisions you need to make, create the plans you need to create, You can't do that in two hours.
So let me take you through my recommendation of the objectives and how it's facilitated and what the topics are. And I hope you can glean something from this. And, you know, the objective of this session, I think is threefold, you know, number one, it's about alignment. It's about getting the senior leadership team Aligned together around what's most important, not just everybody out there working as hard as they can, trying to be as smart as they can, but how do we get aligned on what's most important?
So number one is alignment. Number two is focus. You know, how do we get not only aligned on those things that are most important and those decisions that we need to make? But how do we get focused on the one most important thing or the two or three most important things? Very often I say to a leader, you know, what's most important for you this year or what's most important this quarter?
What's most important to the company and they'll give me a list of eight or ten or twelve things. Should be one or two or three so it's about alignment It's about focus and it's also about team building and when I say team building. I don't mean trust fall exercises or marshmallow exercises or any of that stuff.
I mean the sheer fact that you're working together for a significant period of time, having open, honest discussions that in itself helps to build team, helps to build you into a true team of leaders versus a group of really talented folks. How do we build you into a team? and that could happen just for the sheer hours you're working together.
I have had clients, and I normally recommend the, the session is two days. but I worked with a client actually a couple of years ago that did four days and it wasn't four days of me coaching and facilitating them through. They did four days because they knew they had two days. Of real work and I'll explain what that work is in a minute. But they knew they had two days of real work And what they did from a team building standpoint is they made it four days and added in some other stuff like, hikes and you know longer meals together and obstacle courses and things that they did to also help them create better team.
So whether you do two days or three days or four days, you know, this is not a two hour or a four hour session. This is something that really, you should use to help you create, not predict, not project, but create a successful next year. That's what it's all about. How do you create that team?
Through the alignment you have, through the focus you create, and through this great team that you always continue to build. So, so that's the objective.
There is typically some pre work involved when I facilitate my clients through annual planning. I like them to do pre work. I have a survey that goes out, you know, what's your vision?
What do you think the vision of the company is 10 or 15 years out, three years out? What's a, what's the most important part of your strategy? What's part of your strategy you don't agree with? there may be a SWOT analysis. I have people do pre work. I have something called the Breakthrough Leadership Team Assessment that I have them do, which is just a way to assess the strength
of the leadership team that pre work is important because you gather a lot of great information that way. But more than gathering information, what it does before the session is it gets every leader just to start thinking about all this stuff we're about to talk about to put that strategic visionary, leadership hat on and get out of the day to day, grind and the day to day tactics.
So there's typically some pre work involved.
Notice I called it an annual planning retreat, not a session. I find it's pretty important to have that off site. Now, off site could mean, you know, flying to a beautiful island somewhere. But off site could mean a room, you know, you,you paid for at a hotel.
Hotel a mile away from the office. It's important to get out of the office. It's important to get out of the office. for a tactical reason, people don't get interrupted that way. There's no, Hey, can I just, you know, see Linda for a minute? when people, you know, when we take a 10 minute break and you're onsite at the office, people get hijacked during that 10 minute break, but it doesn't happen if you're in some offsite location.
Being in an offsite location is just helpful. For people to think differently. If you're sitting in the same damn chair in the same conference room, you tend to think the same way you always think, but when you go somewhere new and different, you could be a little bit more creative.last thing I want to tell you before I dive into what the agenda looks like is how this thing is facilitated.
N
ow, very often it's the CEO, That facilitates the annual planning session, but let me inject a little commercial for coaching here. I have seen it and my clients have seen it to be critical that the CEO has the ability to participate in the meeting. And when you are facilitating the meeting, it is almost impossible to facilitate the way you want to facilitate.
When you are participating, you might get caught up in an argument or caught up in a debate and not realize it's not a critical one to move things forward. And you could spend an hour on it and then lose the ability to talk about something really important. When you're the CEO and you are participating.
Sometimes you're, when you're facilitating and participating, you can tend to do the opposite and cut a discussion short because you've got a strong opinion and not give the people around you a chance to air their opinions and to challenge your opinions. You know, very often as the leader, when you state an opinion, it can feel like, a command instead of an opinion, whether you mean it to be that or not.
So having an outside facilitator who's the one that could worry about how we're doing on the agenda and where we are on time. So the CEO doesn't need to worry about that. Having a coach and a facilitator in the meeting to drive to make sure everyone's voice is heard. When you're debating an issue or an opportunity to help coach the leader, help coach the CEO to make sure that they speak last.
You know, all of those things become really important. So my clients find it so valuable to have a coach and a facilitator in the room, because if the CEO needs to do it, not only will they not do it well, but man, that's tiring and really difficult. To do both. The other thing I'll say about facilitation is there are very simple ways to make sure everyone's voice is heard around that table.
And that's so critical. And if you just bring up a topic and have everyone discuss it, what I'm sure you'll find is I find with the leadership teams I work with is there are some leaders that like to take the lead and like to be heard and like to engage in conflict and just. You know, that's who they are and where they're comfortable.
And there are other leaders that like to sit back and listen, and are not necessarily as comfortable challenging the status quo, challenging the popular opinion. And sometimes those quieter folks could get drowned out by the louder folks. So there are ways to facilitate very simply. I'm a big fan of flip charts and post it notes.
Let's get everybody's ideas up on post it notes up on a flip chart and then talk through them. So the quietest among you has as large a voice as the loudest among you.
That all being said, let's dive into what I use, what I think are the major parts of the agenda. of a annual planning retreat, remembering the objective of alignment, focus, team building, which means we're going to focus in the agenda on things like longterm vision.
We're going to focus on strategy, more that three year view, what differentiates us? What are the strategies that will enable us to achieve that vision? We're going to talk a lot about people, culture, structure, and we're going to talk about. How to execute. What are we doing over the next year?
What are we doing over the next 90 days? So that all being said, let me take you through the agenda. I always like to start all agendas with some form of good news.really important to start there. Not only does it get the meeting started, you know, on a positive light, even if you had a real tough year, but you know, If people know coming in that you're going to start off by focusing on some form of news, they start to think, what good news do I have?
and I am a true believer. You get more of what you focus on. So if we focus on the positive, we, if we focus on good news, we will get more of that. I have seen leadership teams just you know, down and nothing's going right. And they're having a really difficult time of it and they're worried about so much.
And then we dive in and we start with some form of good news and the world changes for them. And all of a sudden they go from down in the dumps and not very creative to super creative you know, clearing their minds, giving themselves the ability to think in a really powerful way. So in the annual planning, my form of good news is what are the bright spots?
And let's imagine we are, you know, I'm recording this in 2024, so let's make believe we're planning 2025, I would start out with what are the most important two or three bright spots from 2024. And that means everybody writing on a couple of post it notes, what the bright spots were for the company or for themselves.
putting it up on the flip chart and bright spots, not only from a business standpoint, but I like to include personal bright spots as well. Now, for some people that may feel like a waste of time, this is about business, but it's really important for building a powerful team for you all to get to know each other and start rooting for each other, you know, from a personal standpoint.
So understanding what wins people had. During the year, I think is pretty important. And of course, understanding the wins from a company standpoint to start out is important. Again, it starts us off on a positive light. You get more of what you focus on and it starts us thinking, how could we leverage those wins into the next year?
So we start off with bright spots for the year. We then go into lessons learned from this past year. What are the most important, again, two or three lessons learned from your successes? From your failures? From your mistakes? Could be from a positive experience or a negative experience. What were the two or three most important lessons learned?
And from those lessons learned, is that a good to know? Like, thank God we learned that lesson and we've already taken action on it. Or is there some action we need to take on that lesson learned? And again, when it comes to these first two agenda items and almost everything I talk about moving forward, the bright spots, the lessons learned, it starts off, Hey, get out a post it note, write on two or three post its what your bright spots are, what your lessons learned were.
And when we get there, they go up on a flip chart so we can talk about everybody's bright spots. So we can talk about everyone's lessons learned and what are the actions we need to take from those lessons learned. So those are the first two agenda items. Bright spots from the year, the previous year.
Lessons learned from the previous year. And by the way, if I didn't say it, normally with my clients, these annual planning meetings happen in November or December, planning for the next year. Some people like to do it much earlier, like September. that makes sense sometimes. But my fear is that's a little too early.
You've still got a lot of, 2024 left and you're trying to plan 2025. Now there might be a budgeting process that happens sooner, but the annual planning retreats I do are typically November, December, not always. So first two, bright spots, lesson learned. the third thing I like to do, and I do this in, in all of my quarterly meetings, as well as the annual planning meetings, with my clients is something I call pulse check.
Pulse check is a way to throw two or three questions at the group that help to identify one. How are people feeling about the company and the team right now? What are the major issues we need to make sure we talk about at some point over this two day session? What are the major opportunities we need to discuss?
Very often, the most important topics we need to discuss are not topics that are on the agenda. And when we throw two or three pulse check questions out there, and one question could simply be, how are you feeling about the company? Another one I like is what is our number one obstacle to profitable growth?
It might be, what's something we're afraid to talk about that we need to talk about? What's one opportunity we need to move faster on? What's the biggest issue our employees are having or the biggest issue we're having with our team members? What's the biggest, issue we're having with our clients. You get the idea.
And I have a, an inventory of about 35 or 40 different pulse check questions that I pull from. But when you put those questions to the group, two or three questions, write your answers on post it notes, put them up on a flip chart that drives so much great discussion. and what I tend to do is not what I always do, frankly, is I don't dive deep into it.
into any issues or opportunities or discussion items that come up. I don't dive deep into them right then. Because if we do, we're in danger of spending two or three hours on stuff that's not very important. So what I do is when we go through the pulse check for each question, I ask the question, I say, is there an action we need to take?
I call it a who, what, when. Is there a who, what, when? We need to take as a result of this. And if it is, let's document it.is this an issue we need to add to our issues list? Is this a potential annual priority or quarterly rock, which is quarterly priority, or is there no action we need to take here?
Yes, that's an issue we're working on it. We don't need to talk about it anymore. We don't need to take any action. It allows us to go through the pulse check questions more quickly. And we wind up with a pretty powerful list. Of potential priorities and focus areas that come from it and potential issues and opportunities that we add to our list of potential discussion topics, which we'll get to a little bit later.
Okay, so the third agenda item is pulse check questions.
The fourth is now we're going to look back and I don't like to spend a lot of time looking backwards in an annual planning meeting. But we're going to look back at how we did. For the year and how we did for the quarter this past year for both of those, we're going to look at how we did from a numbers standpoint, financial targets, non financial targets.
How did we do? How did we do on our annual priorities? Did we achieve them? If we did, what did we learn from them? If we didn't, what did we learn from that? How did we do on our quarterly rocks or quarterly priorities? Again, if we achieved it. What value came out of that? What did we learn from it? If we didn't achieve it, what did we learn from it?
So, so we're going to look at our, you know, key performance indicators are numbers. We're going to look at our priorities. And again, we're going to spend as much time on that as we need, but I like to spend way more time looking forward than looking back. So we're not going to spend a half day going back through a gnats ass level of detail on every priority and every KPI We're going to talk about what's most important next on our agenda.
Now we're going to look forward and we want to talk about vision and strategy and within vision and strategy. We want to talk about what I call our two core ideologies as it relates to the vision moving forward. And number one, it's looking at our core purpose. Core purpose is your why. You know, for example, Disney's core purpose is not theme parks or movies.
It's probably happiness. Starbucks core purpose is not a cup of coffee. It is a third place. We've got work, we've got home, we've got Starbucks to go relax and have a cup of coffee and people watch or do whatever we're doing. So what's your purpose? What's your why? As a company, and if you've got one, let's confirm it and discuss whether we're living it or not.
What else could we do to better live our purpose? We're also gonna look at our BHAG, our 10 to 15 year big hairy, audacious goal. Our flag on top of a mountain, our moonshot, how what, whatever, what, however, whatever term you wanna put on it, but how are we doing progressing towards our big, hairy, audacious goal, or if we don't have one or.
Maybe we've actually achieved our big, hairy, audacious goal. Let's talk about what our next one is. Because we want our leadership team to be aligned around this long term, almost never changing vision of the company. We want them more than aligned around it. We want everyone to be an evangelist of that vision.
So we need to get folks excited about that vision. And post the meeting, we need to get everybody in the company excited about that vision, but we need to talk about the long term, almost never changing vision. And then we also need to talk about that kind of midterm three year vision. And I like the term three hag.
Three year highly achievable goal So as opposed to a big hairy audacious goal, man I don't know if we're ever gonna achieve that but how cool would it be if we did a three year highly achievable goal is One you absolutely commit to achieving and I'm borrowing that term from you know the brilliant Shannon Susco and her book three hag and her coaching organization, Metronome United.
So the three hag again, it's a shorter term vision. It's a three year vision. What are the financial and non financial targets? What are those differentiators that you need to build on over the next three years? And I also liked the book, Vivid Vision by Cameron Herald.
And he talks about building, of course, a vivid vision. That's the name of the book. But it's more of a three dimensional view of what's the company gonna look like three years from now. Sound like, feel like, smell like, I don't even know what sense I'm missing, but it's three dimensional view on, you know, when we walk down the hallway, what are we going to hear?
you know, what are we gonna feel? what's the. What's the media going to be saying about us? What is it? What are our clients going to say about us? What are our employees going to say about us? It's that three dimensional view. So what we talk about vision, it's the longterm almost never changing, but then it's that three year vision and strategy.
We then want to move into topics focused on people and by people, one part of that is culture. And a big part of culture is what are your core values as an organization? so in this topic, we might look at your core values, your non negotiable behaviors, the three to five or six non negotiable behaviors that anchor your culture.
How do we feel about those core values? Do we still feel like those core values work? Do we have the right definitions? Are we living those core values? Are they just posters on the wall? Are we living them every day? Are they alive and well in our organization? What do we need to do to better live them?
Do we need to recognize people more often for the core values? Do we need to change our hiring process to better ensure we're hiring people that are already living our core values? core values. What do we need to do to take it from a poster on the wall to something we're living and breathing every day.
So we're going to talk about culture. How are we doing on culture? Where do we need to work on culture? From a people standpoint, we're not only going to talk about culture, we're going to talk about structure of the organization, starting with the leadership team. And, I did an episode not too long ago, talking about the functional accountability chart.
What are the functions of the organization? Who is the one person accountable for each of those functions? What are the measures of success for those functions? Do we need to reassign any functions? Do we need to add any new functions? Do we have people that are stretched too thin in how many functions they're accountable for?
So we want to look at structure of the organization. So within people, we want to look at culture. We want to look at structure. And lastly, we want to look at talent. Now there are a number of other podcast episodes where I talk about the quarterly talent assessment. Well, that happens in our quarterly meetings, but it also happens in the annual planning retreat.
So we want to look at our talent one level down all of the direct reports that of the leadership team and understanding who are our folks that are high performing, middle performing, low producing, which means they're low in productivity. And who are the folks that are low culture fit folks? What actions do we need to take to strengthen talent within our organization?
What's our talent density indicator, which is a, KPI that I've created. I believe I've got another podcast episode that talks about that, but real quickly, and it's going to be in my new book. I'm in the process of writing,called the strength of talent, but the talent density indicator is a KPI that measures the strength of talent.
And very simply, it's your percent high performing folks minus your underperformers, which is your low producing or low productivity folks and your low culture. Fit folks. And if you take your high performers and subtract from it, your low performers, you're going to get a number between negative 100 percent and positive 100%.
Well, in the annual planning meeting, we want to look at that too. How are we doing? If we don't have the right talent, we are going to have a real tough time executing on what we need to do this quarter, this year, in order to create The vision that we just created, our three year view, our longterm, almost never changing view.
So within people, we want to look at culture. We want to look at structure and accountability and we want to look at talent. Next. W
e want to look, we want to go back to those discussion topics from the pulse check. We came up with some number of discussion topics, issues we needed to talk more about.
opportunities we needed to talk more about, decisions we need to make, and here's where we'll prioritize which ones we need to talk about. Which are the most important ones to talk about that will help drive our plan moving forward? Because, by the way, we don't have our plan yet. We've got our three year strategy, we've got our long term vision, but we don't know what we need to Go do when we leave here.
So in order to do that, there are some discussion topics. We've got to talk through so prioritize that discussion topics Spend time on discussion topics. W
e then move into finally the annual plan and if you are in November of 2024, you're going to look at the plan for 2025 and In that annual plan We're going to look at what are the?
Financial and non financial targets. Financial targets is, you know, what do we want the P&L to look like? In 2025, non financial targets are things that drive that. How many new clients will we need? How many new products or services, you know, do we need? So let's look at the financial targets and non financial targets.
And then what are the one, two, three top priorities for the year? And when I say priority, a priority is not to reach our revenue targets. We've got the revenue target. The priority is what do we need to do? What big action or actions do we need to take in order to hit our financial and non financial targets in order to live our values, in order to drive us forward to our three year vision and our long term vision?
What are those big annual priorities? What are we doing not to work in the business, but to work on the business? So we've got our annual plan. Then we move into our quarterly plan. I believe the quarterly plan is the most important part of the plan. And it's most important because all these other things we're talking about, long term vision, mid term vision, annual plan, there's not a big sense of urgency there.
And even an annual plan, here's what we need to do this year. Well, In the next three, four months, the world can change, you know, and if you told me, Hey, Mike, you need to lose 15 pounds in the next year. I can still order a pizza tonight and feel pretty good about it. But if you say, Mike, you need to lose six pounds in the next 90 days.
Well, now there's a sense of urgency. There's a pretty big fire up my butt to make sure I do the right thing.
tonight, tomorrow, and the next day. So we need a 90 day plan because that's where we're going to take real action.
So in that 90 day plan, similar to the annual plan, we need our financial and non financial targets for our quarterly plan, our 90 day plan. We also need our priorities, and in this case, I call those priorities ROCKS. And we have company ROCKS and functional ROCKS.
Company ROCK is what are the two or three most important things for the company. And by the way, you should see alignment. There should be alignment between your quarterly ROCKS and your annual priorities. Your quarterly ROCKS are what's the next 90 day chunk of the year. of the annual priority. The annual priority should be what's the next 12 month chunk of our three year plan.
Our three year should be what's our three year chunk of our big hairy audacious goal. And all of that you should be doing while living your purpose every single day and living your values every single day. So we need company rocks and then functional rocks are, you know, you might have a leadership team of six people, Three company rocks.
And by the way, each rock should have an accountability person, one owner. So, if you have three company rocks and a leadership team of six people, you may have three owners. Whole lot of people responsible, but three people accountable. Now, I believe everybody around that leadership table should own at least one, no more than two rocks for the quarter. So if you don't own a company rock, you might create a functional rock. If you head up finance, maybe there's something within the finance function that you want to commit to the leadership team that you're going to do to work on that function and improve that function over the next 90 days.
and of course, if those functional rocks could align with the company rocks, all the better to get everyone focused. Working on the same two or three most important things. So we now have our annual plan. We have our quarterly plan. We know who's accountable. We understand our financial and non financial targets, our key performance indicators.
We now know when we leave here, what we need to go do. So the last thing we need to do is wrap things up.
And the most important thing I like to do in wrapping things up is something called cascading communication. And in cascading communication, I like to get my leadership teams crystal clear on what they are agreeing to communicate out and down throughout the organization based on these great discussions they've had over the last couple of days.
And what are they agreeing should stay in that room and not be communicated? So, for example, having your teams understand what the annual priorities are, what are the quarterly rocks, what are the financial and non financial targets? All those things might be super important to communicate to your team so they can align around it and help you.
Resolutions to any big decisions or issues or opportunities might be important for people to know. Over on the no side, there may be parts of the strategy or parts of the one year, one quarter execution plan that are important for the leadership team to know and no one else. The results of your talent assessment.
Who specifically are the folks that are high performing or middle performing or low performing should not be shared with people outside the organization other than in the individual coaching you might do with your people. And even then I wouldn't suggest you say, by the way, we did an assessment and you are low performing.
What you do is you sit down with them and coach them and help develop them. wherever they were low performing. So that cascading communication is critical because I've seen time and time again, people leaving that meeting and talking about things they should not be talking about because it wasn't clear before or leaving that meeting and not communicating with their teams, things that should be communicated.
So that's a really important part of the wrap up. And then I also like to go around the room is part of the wrap up and just ask people. You know, what they thought the most important part of the last two days were, or it might be, Hey, give me one word or a phrase describing, how you feel about what you have all accomplished together over the last couple of days, super good, typically a very positive way to end the meeting.
that was a mouthful.
If you are not doing an annual planning retreat. I hope this convinced you to do one and helped you to understand what's most important.if you do one, but well, if you do one, I hope you heard this and found at least one or two ways that you could improve how you run that retreat or how you schedule it or how you facilitate it, or if you want to bring in a coach.
to do something like that. Hope that helped. So I always say, if you want a great company, you need a great leadership team. An annual planning retreat is a super way to help you get there. As my friend Owen Fitzpatrick says at the end of his podcast, may the force be with you. Bye bye.