Jan. 26, 2023

How to Run a Great Off-Site (BONUS EPISODE)

How to Run a Great Off-Site (BONUS EPISODE)

Episode 18: Today, host Jesse Pujji (@jspujji) is bringing you a special bonus episode addressing a frequently asked question: How do you run a great offsite? Listen to hear Jesse break down the fundamentals of running an impactful offsite with your team—from effective preparation, to what types of strategy sessions to hold, to the best team-bonding exercises. 


(00:00) - Intro

(00:29) - Why you run an off-site

(01:24) - How to run an effective strategic off-site 

(05:14) - What makes for a great off-site beyond strategy

(6:00) - Bonding games and exercises

(07:11) - Important things to keep in mind when preparing for your off-site


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Alex Lieberman: What's up, everyone? I'm Alex Lieberman.

Jesse Pujji: Yo, this is Jesse Pujji.

Alex Lieberman: And this is The Crazy Ones.

Jesse Pujji: What's up, everyone? It's Jesse Pujji, your resident Crazy One. I am doing a special bonus episode while Alex is out, of a question that we keep getting from the audience, which is, "How do you run a great offsite?" So let me jump into that in just a second. Before I do that, why do you run an offsite? If you're a CEO or a manager running a business, what's the point of an offsite? And what are you trying to accomplish with it? For me, I think of three really critical things when I think about why you run an offsite. Number one is setting direction, number two is alignment, and number three is connection. So let's take each of those briefly. 

Number one, setting direction. You as a leader want to be clear about where you're going, and you've decided, and want to share that out. It's critical to get the team to understand that, which brings us to alignment. Alignment doesn't just mean they all come in and agree. It means they actually tell you why they disagree, what you're missing, and you bring that all together into one single plan. And then third, and most important, last but not least, is connection. And this is where you get to know each other as people, you get to laugh together, you share some intimate moments, and that's a critical part of running an offsite and having a successful team dynamic. 

So how do you run it? Let's go through Jesse's method for doing it. So there's a few sessions I think are critical from a strategic perspective for a well-run offsite. It all starts with reflection, getting everyone together and asking, what did we do great last year? What did we not do so great last year? What's critical to get right this year? And what do we want for this year? Handful of questions like that. Sometimes I call it "accounting and response." Did we do what we say we would do? Did it work? If it did, great—let's do more of it. If it didn't, let's do less of it. That's the first session of reflection. 

The second section is what I call visioning or desired future state. This is where the leader will set out one year, maybe three years in advance. What's their vision? What do they want it to look and feel like? What numbers do they want to have in the business? What kind of team do they want to have in the business? What product goals do they want to accomplish? That's really the big goals that you're setting out for the team. And then sharing what you think are the most important priorities for how you will get those goals accomplished during the year or during the quarter.

This is a critical session. You set it, and there's a trick I learned from my coach that has changed the game when it comes to running offsites and strategic planning. After you as a leader share that vision, you go around the room and you say, "On a scale of zero to 10, how much do you guys agree with this vision?" And what you'll notice in that question is that nobody's going to give you a two; nobody's going to give you a nine. Everyone's going to be between four and probably eight. And what it does is it unlocks an immediate mechanism for feedback. So all of a sudden you can say, "Well, why were you your number and not a zero?" And that shows you quickly why they agreed with your plan. So I would go around the room and ask each person and write those things down.

Then I'd say, "Great. What would it take to make you a 10?" The way that that question is framed is super, super important because it's not saying, "What don't you like about the plan? What's wrong?" It's saying, "Give me an edit. Give me a suggestion for how you would become a 10." And immediately you start to get, "Well, I think we need more resources," or "We're missing this sector," or "This is an area of opportunity that you didn't mention," and it becomes a really productive session in bringing the whole team together and aligning. This is really critical, because one of the experiences of offsites people hate is people shouting over each other, or having a runaway session where people talk in circles for hours on end. So you as a leader want to bring structure to that session. 

So reflection, desired future state. Typically one to three major issues will come up in that alignment that everybody keeps mentioning, "Oh, we don't have enough resources," or "Oh, our sales plan is off." Those sessions I save for maybe the next morning, and we'll break down and actually have individual sessions on each of them. Here you want to get everyone around the table, acknowledge what the issue is, and start to brainstorm solutions for how you can solve it. I use sticky pads, kind of like a product brainstorming session, different colors, people come up with ideas for how they can solve the problem. Then we start to aggregate them, and themes quickly start to emerge that allow a real solution to come into how to solve that big anchoring problem. 

Last but not least, I like to take each department, and if everybody's aligned to the desired future state and strategy, they aligned with the major priorities. Each team has individual goals and some of the key initiatives or ideas that are going to drive those goals. So let breakouts take place and let everyone start to put those goals and ideas together, until everyone's aligned at a pretty high level for where the business is going. 

That's the strategy side. I think when you're doing an offsite, you want to make sure you hit on all of those. Reflection, vision, making sure you can think about how to close the gap from where you are today to that vision. Then getting a little bit more specific about individual problems. And last but not least, getting each team to have their clear goals, and which initiatives and ideas they want to run during the quarter. 

To have a great offsite, you can't just do strategy. So I also like to recommend, do one or two guest speakers. We just ran an offsite for Kahani, one of my businesses, and we had a customer guest speaker, and we had another entrepreneur who's built an e-comm tech business. Both of them brought unique angles. They were able to inspire the team in ways I couldn't have imagined, and we all walked away feeling refreshed and we'd learned something new. So I would recommend one to two guest speakers. 

I always recommend one to two skill-building sessions. I love exercises from the Conscious Leadership Group. It could be how to give feedback effectively. It could be, one of our sessions we walked through how the Shopify API works, and what actually data we can get from it. So it could be anything that builds skills or gets you to know important things that are gonna help everybody run the business better. 

And last but not least, I always like to have at least one or two bonding exercises and activities. One of the easiest ones is a game called "If You Really Knew Me," and we just go around in a circle and we say, "If you really knew me, you'd know blank." And it could be something really deep about yourself. It could be something just funny, and we'll usually do multiple rounds of it. So we'll go, "If you really, really, really knew me," and it gets deeper and deeper, and that intimacy builds that connection. That's one game. 

Another fun game is called Car and Driver. My coach taught this to me. You get one person who's got their hands on someone's shoulder, who's the driver, and you got someone who's the car who they push around. First, you have them push them around with their eyes open, then you have the car close their eyes. All of a sudden the driver has to communicate a lot more. Then you do funny things like have them run into each other and guide different people. Then they can't use words. So you can start to build on Car and Driver. I'm sure if you Google it, you can find it.

So these are fun games that bond the team. Typically, connection is built through intimacy, play, and touch. Those are the three ways to build connection amongst the team. So you think of exercises and activities like that. 

So that's Jesse's 101 for running a great offsite. I'd be remiss not to mention, there's always a few things to remember when you're doing this. Number one, offsites are not a place to make big decisions. You as a leader have made some decisions, you have a direction clear, and you're trying to bring alignment. And I think that distinction is super important, to come in with a plan and come in with a perspective, and allow the team to give you feedback and align towards it. If you come in without any clear decisions and ask people to help make decisions, you're in for a very unproductive couple days.

The second one is, each session requires structure. So don't walk in and say, "We're going to reflect now. Everybody reflect." Come with specific questions, come with prompts. One of my favorite methods is just everyone write down what their thoughts are quietly, then share them out and see if themes emerge. But bring structure to each session, or they become unproductive really quickly. 

The third one is, delegate this out to your team. Have them interview a client as a part of the offsite. Have them run one of the sessions on one of the topics that is about to come up. Have them do the reflection exercise. It's a great way to involve your team and take some work off your shoulders as the leader. 

Number four is, of course, don't expect perfection. You're not going to touch on everything. You're not going to hit every item. Like everything in entrepreneurship, you're trying to get a seven or eight out of 10 to have success.

And last but not least, have fun and enjoy it. These are really unique moments with your team. Take people out for walks in the evening time. Have fun dinners, just have a blast, because these are the things you actually remember when it's all said and done, from the entrepreneurial journey. 

So that's Jesse's quick rundown on how to run great offsites. I hope this was super valuable for you. Don't forget to always write us in at thecrazyones@morningbrew.com. We want to hear feedback on, was this valuable and was this format valuable, where I just did a quick and dirty on running offsites. Talk to you soon.