Almost all companies host some form of an offsite meeting (regardless of whether the venue is offsite, onsite, or, now in a COVID world, on Zoom). A strategic offsite session is a huge investment of time and your company’s resources. Offsites can be tremendously valuable, yet, we’ve all been in ones that fall short of creating the lasting change or alignment they hoped to bring. One of the main reasons is poor planning and execution of the offsite itself. Having hosted many of these, some that went well, and others that didn’t, I am sharing my guide for hosting a great offsite. 

As a CEO, your management team offsite rests on your shoulders. Preparing for the offsite should be one of your top priorities. While everyone on the management team should be involved, the CEO should drive offsite planning and chair the meeting. 

Start by thinking about the objective(s) of the meeting. Why do you need an offsite / what do you hope to achieve? To do this, it may be helpful to define the time frame that you want to impact. Depending on the stage of the company, this might be 6-12 months for an early-stage company or 1-2 years for a later stage company. With that time frame in mind, what is the most important thing to discuss? I find that it is helpful for CEO’s to force themselves to identify 1 or 2 things they want to get out of the offsite - any more than that can lead to an agenda that is too busy to accomplish true strategic work. 

I believe that a one to two day offsite is best as it gives you enough time to dig deep into a set of topics but avoid the diminishing returns that often come with long meetings. Avoid the temptation to be broad and err on the side of less vs. more. Don’t try to jam everything in and over-structuring the offsite - you should have plenty of buffer time to allow conversations to flow. 

Planning for the offsite:

• Make sure to give yourself and your team enough time to properly prepare. In my experience, it’s very hard to do a proper strategic session without at least 6-8 weeks of prep time. Most importantly, you want everyone to be thoroughly prepared for each session. Since the day job of running the business does not go away, your team may need to shuffle their schedules to allow for enough prep time in the weeks leading up to the meeting. 

• Offsites can sit along the spectrum from purely social to purely business. I think a good offsite incorporates a bit of work and fun but where exactly you fall on this spectrum may depend on the tenure and composition of your team. If you have a brand new team, you may want more time for team building. 

• Pick a venue (and budget) that is consistent with the values of the company and reflect the backgrounds of the attendees. I encourage CEOs to be careful of being too cheap on the budget - you want people to feel comfortable and ready to pour their hearts into the meeting itself. Having a good night's sleep, access to fitness equipment, healthy food, etc is important. Additionally, you may consider an agenda that allows for multiple breaks (depending on your ground rules, discussed below). 

• For a Zoom offsite, consider spreading out the offsite across 2 or more days to avoid Zoom fatigue. Also, consider ordering food/beverage deliveries so that your team can be focused on the meeting without worrying about meal planning for themselves and their family. 

• Consider having a facilitator and/or note taker. While note-taking could be assigned to an attendee of the meeting, a facilitator should be someone independent of the discussion. The role of the facilitator is to improve the quality of dialogue and engagement of the team. The facilitator can also help enforce ground rules. Hiring a facilitator will add cost to the meeting but can be quite effective, especially for teams that are still finding their rhythm.

Building the agenda:

• Once a date is set, I suggest using the next scheduled executive meeting to discuss topics. The CEO owns the agenda but this is a good opportunity to solicit topics from the rest of the executive team. I encourage CEOs to candidly ask about “elephants in the room,” that need to be discussed but haven’t come up in normal discourse. To get candid responses, consider setting up a quick survey or asking for input in direct report 1:1 meetings. 

• Decide which topics make sense to cover. I suggest looking for topics that touch on potential conflict or disagreement within the company. Focus on topics that can impact the business within the relevant time frame and avoid tactical topics which can be easily covered in regular meetings (vs. an offsite).

• Once you know what you’ll be discussing, start building the agenda. How you structure the day can vary greatly with what needs to be accomplished. Ideally, each session has a clear owner (in my experience, one owner is better than multiple). Have the owner draft a slide (or a few bullet points) to guide the discussion of his/her session. Each session should have an owner, topic / key questions to discuss, the goal of the discussion, and reference materials (if applicable). 

  • Gathering topics before setting the agenda is essential. A cookie-cutter schedule that looks the same regardless of what’s happening in the business will not have a lasting impact.

  • Most sessions should encourage discussion more so than presentation. Try using open-ended questions and use the session to find answers. Slides should be used for sharing data or context.  

  • Ask session owners to limit their reference materials / pre-read to what is needed to know, not a data dump. 

  • Avoid too much structure! Don’t try to jam everything into the agenda. The topics you pick should warrant deep discussion and maybe contentious so make sure you give each topic the time it requires. Avoid ‘lightning round’ discussions where much is said but nothing is solved. 

Leading up to the meeting:

• Share the agenda with the management team and brief the company at an upcoming all hands on what the offsite hopes to achieve. Outside of the exec team, many folks in the company may be engaged in preparing materials for the offsite and they, along with colleagues, will be interested to know what will be discussed. Sharing some context on the meeting and the big topics being addressed will go a long way for the team. 

• After the agenda has been set, check in with each session owner to make sure they have what they need to facilitate a great discussion. The key is to align on the goals of the discussion since that will drive the rest of the content.  

• Send out the final agenda and all materials at least 1 week before the meeting. Give everyone plenty of time to read through the materials. If needed, ask people to block time in their calendar so that they can review. 

Game time:

• Kick off the meeting with an overview session led by the CEO. Use this time to set the stage for what you want to achieve with the offsite and revisit your objectives. I encourage CEOs to give a “state of the business” update as part of the overview to level-set everyone on how the business is performing and what’s working / not working at a 30,000-foot level. 

• For many companies, the voice of the customer plays an important role in any strategic discussion. Consider starting the meeting with a customer story or finding other ways to keep the customer perspective throughout the meeting. 

• While every team has different norms, I am a fan of setting specific ground rules for the meeting. It’s not just important to engage, but everyone must get what is on their mind into the discussion. I believe a good set of ground rules includes:

  • A reminder of the company values - if your company has set values, keeping your values in mind throughout the discussion is important. Consider placing the values somewhere in the physical space to keep this top of mind. 

  • What everyone is committing to - I believe that great teams seek alignment rather than consensus - so having everyone commit to finding alignment rather than consensus or to disagree but commit may be important. On a more tactical level, you might ask the team to commit to certain norms throughout the meeting. For example, are you asking your team to turn off phones/email outside of breaks?

  • Follow-ups - at the end of each session, the session owner is expected to summarize the follow-ups and action items and have clear owners for each. 

  • Clear the room - this is a tactic that can be amazingly helpful and yet simple. At the end of each session, consider going around the room to “clear the room.” If anyone has something they want to say or has immediate/candid feedback they want to give to anyone in the room, they do so before the group moves on to another topic. Once everyone is “clear,” the discussion can continue. 

• Use physical space. It can be hard to stay focused after a few hours so I suggest using the space as much as possible. 

• Have a parking lot of topics that come up in the meeting but can be covered after the offsite. Undoubtedly, the meeting will surface many important topics, and to stay focused on the objectives of the offsite, you will need to defer many of these topics to a later time. It’s good practice to note these when they come up and assign owners who will be responsible for making sure the topic is scheduled for a later date. 

• Consider using part of the time for 360-degree feedback. In many of our offsites, we would run 360 feedback ahead of the offsite and use some of the time to discuss our individual and group feedback. This also allows your team to discuss ways they can work better together and how you could better support them. 

Post-offsite: 

• Before leaving the offsite, spend 30 minutes discussing internal communication. Summarize the offsite discussion and decisions made and decide what you are going to share with the rest of the company. While this can wait for the next all hands, if straight forward enough, consider sending a short team email to share the high-level takeaways and acknowledge that a longer update is coming. 

• Collect feedback on the meeting either in your next exec meeting or in 1:1’s. The next offsite will come up faster than you think! 

• Schedule weekly offsite check in’s as part of your exec meeting or separately until the remaining loose ends are clear. 

Just like every company is unique, every offsite is different. CEO’s should tailor the meeting to the specific needs of the business and their leadership style. Having a full day or two with your executive team is a rare event; having a lasting impact on the company is the prize. 

If you’re planning your executive offsite and want a sounding board, please drop me a line (gautam at m13.co)