It takes a lot of time and money to bring your seniormost group of leaders together-it's critical that it is time well spent.
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As we kick off the year, many of you are likely planning gatherings for your companies. One of the most critical gatherings to get right is for your leadership team. Unlike the typical weekly meeting which may involve remote or hybrid attendance, offsites tend to be special in-person gatherings at non-office locations to take a step away from their day-to-day work and plan for the year ahead.
It takes a lot of time and money to bring your seniormost group of leaders together, so it is critical that it is time well spent. As a former Chief People Officer and now someone who leads offsites for a living, here are some best practices to maximize the ROI of these events.
Every great offsite starts with great planning. And a great plan needs a clear objective. Make sure you can answer these questions:
-What do we want to achieve in our time together?
-How will we know if we’ve been successful?
Some common objectives I see are: build trust, integrate new leaders, make a hard decision, align on priorities, debate the strategy, enhance our operational rigor. Balance is key, even the most business-focused offsites should include time to connect with each other.
Ensure the offsite topic will naturally flow with the cadence of the year. If your fiscal year ends in January, January and February are likely great times to plan the year ahead. If you have a new leader joining the team in March, potentially plan a gathering in April so they have a few weeks to settle into the new role before gathering. If there will be a big product launch in Q3, consider how far in advance the team will need to align to make it a success, and schedule your offsite accordingly. If you can swing it, pre-planning offsites for the entire year ensures your leaders can plan ahead to prioritize this critical time together.
Once your objective is clear, hire a facilitator. A great facilitator will help you build an agenda to meet your objective and lead the event to ensure there is focus and flow, and enable equal participation across the team. When hiring a facilitator, look for one who will be credible and have chemistry with the team and who fits into your budget. Once your team finds a great one, it’s common that they will stay with you for many quarters or even years, so take the time to find someone fantastic the first time. Ask for referrals from executives you trust or from your board if you need a place to start.
Be realistic about the amount of time needed to reach your objectives. Although it’s challenging to step away from the day to day, committing to a minimum of 2-days away together will ensure you can build trust, make decisions and leave with clarity on what needs to be done next. Often offsites are squeezed into a day under the false assumption that less time = higher ROI. The healthiest leadership teams I work with who have the most successful businesses currently go away 4x/year together, quarterly for 2 days and once/year for 4 days. Team cohesion takes time, so make the investment!
When you think about the venue, budget, vibe and location are all important considerations. If your team is distributed, pick a location that is neutral and centrally located. If your offsite is multiple days, hotels are great but renting a big house can often be more fun and practical. Having multiple spaces to meet in is a luxury. Perhaps you start the morning outside by the pool, spend the middle of the day around a table inside and close the day with a hike. Having indoor and outdoor options levels up these events from good to great. If you are budget conscious, consider borrowing space from a friend or renting through a company like Industrious.
At a minimum, make sure the space has natural lighting and bonus points if it has access to the outdoors. Offsites provide the most ROI when you get into the tough topics, so having light and oxygen are key!
Human connection is harder virtually, so use the time together to build and deepen connections. This can be as simple as having a dinner with no agenda or asking people to share their favorite song so you can create a team playlist. Teams that get to know each other personally are the healthiest. In my experience, choosing a book or a theme can be a great starting point. Two of my favorites are The Advantage by Patrick Lencioni and Amp It Up! By Frank Slootman. Have your team read the same book or watch a video recap as pre-work makes it simple to incorporate a group discussion on how it applies to your team.
To ensure psychological safety, communication and pre-work are essential. Send a pre-session survey, create & share the agenda inclusive of pre-work, and be specific about breaks that will be honored so leaders can plan their schedules accordingly. Also, collaborate on setting expectations when you gather. Answer the following questions as a group:
-Will we allow laptops and phones in the session?
-What happens if we get off track?
-If things get heated, how will we recalibrate?
Alignment on expectations creates shared buy-in and inclusion.
It can be tempting to focus on execution or near-term problems when you have your leaders together. Avoid this temptation as likely more ROI will be found by using in person time to think big picture, have debates, and discuss the company holistically. One team I work with sets three objectives for each offsite - one focused on the financial health of the business, one focused on the future of the product, and one focused on the organizational health. This type of structure enables the team to talk about it all, not just the shiny penny.
Finally, make sure each offsite has dedicated time at the end to focus on recapping what was accomplished and what happens next. This ensures the learnings will stick and there is accountability to continue the momentum!
If you are interested in support for an upcoming offsite, please don’t hesitate to reach out!
