by Marissa Fernandez and Frans van Loef
As a leader, you’ve noticed something feels off with your team. After years of remote work, your company has shifted to a hybrid or fully in-office model—but the return hasn’t been seamless. Meetings feel clunky, casual collaboration is inconsistent, and relationships that once felt natural now require more effort. Hoping to rebuild connection and alignment, you decide to plan a leadership team offsite.
With more organizations mandating in-office time, this is a pivotal moment to strengthen teamwork and redefine how your team works together. Offsites can be a powerful catalyst for this—but only when designed with clear intent. Many leaders assume that starting with the end in mind is enough to ensure a successful offsite, but in our experience, that’s just the beginning.
As executive coaches with extensive experience designing and facilitating offsites for corporate clients, we have seen that the most impactful offsites go beyond setting objectives—they address the deeper questions that drive real change. While clarifying your goals is an obvious first step, this article offers five additional—often overlooked—outcome-oriented questions that will help you design an offsite that delivers lasting results.
1. How do you want your team to feel?
Considering how you want your team to feel has meaningful implications on the design and delivery of the day. Take a utilities company leader who planned an offsite for her newly established leadership team. When one of us (Marissa) asked how she wanted the team to feel, she said “cozy, comfortable, and connected.” This intention led to a shift in venue—from a sterile hotel conference room to an inviting rental home. The informal setting fostered deeper connections, achieving the desired emotional outcomes.
An animal health leadership team was planning an offsite with the focus of strengthening collaboration. When asked about how she wants the team to feel, the CEO reflected and said, “valued, celebrated, and supported.” Recognizing the team’s resilience through a challenging year, we reshaped the agenda to begin with a collaborative strengths exercise. Everyone had the opportunity to acknowledge each of their peers’ strengths. The exercise immediately boosted morale and reinforced the emotional impact she aimed to achieve. Not only that, the feeling lasted, fueling intensified collaboration in a more systematic way. Being really intentional about the emotions you want to create is very valuable in crafting the right type of experience.
2. What is getting in the way of your team’s success?
A large retailer’s leadership team was consistently struggling to make decisions efficiently. This flaw was preventing the team from operating to their fullest potential and contributing to unnecessary delays on key initiatives. Diagnosing the issue, the leader disclosed that the team lacked clarity on how decision-making works and who to include in which decisions.
At the offsite, specific decision-making tools to support decision-making were discussed and specifically applied directly to three real-time situations. By providing the right tool and using it directly on actual situations, the team immediately clarified their decision-making process going forward.
3. What shift in behavior will set your team on a new trajectory?
Consider in what ways you hope things will be different when examining the “before” and “after” of the offsite. A great offsite is a memorable milestone in the team’s story, after which, it is on a new trajectory. That different trajectory can only be created with different behaviors after the session.
For example, an education non-profit leadership team wanted to transform their meetings from passive status updates into dynamic discussions that harnessed everyone’s best thinking. The team had historically avoided conflict, resulting in surface-level conversations and missed opportunities for robust problem-solving. At the offsite, they discussed the need for more productive debate and co-created a set of operating norms for navigating conflict, such as encouraging diverse perspectives and practicing active listening. To reinforce these behaviors, they scheduled time in each leadership meeting to tackle complex issues and actively practiced their norms during the session. This shift led to more engaged and impactful meetings post-offsite.
4. What do you want your team to stop doing?
Offsites always generate new actions to the team’s to-do list. Less commonly do leaders think about what can be subtracted. In order to create capacity to operate effectively and implement new ideas, exceptional leaders know they need to create room for it.
One of Frans’s clients is the CEO of a financial services organization. After a recent restructuring, she knew the current resource allocation wasn’t in line with the strategic focus of the business. The question of how her team allocates internal resources was paramount. In a specifically focused offloading session at the beginning of the offsite, the team identified ways-of-working and friction that could be eliminated to free up capacity. Dozens of ideas were generated. The team selected three items as a team and each selected one item as an individual to immediately offload. The feeling of release was palpable, and the exercise turned out to be a fire starter for the whole organization—inspiring more offloading, creating capacity for highest value work.
5. How are you going to make it stick?
An offsite offers people a pause in their regular routines to connect and reflect before they often default back into the daily busyness trap. But lasting adjustments and changes are possible and have the greatest significance. Making it stick has to be considered as part of the planning, not as an afterthought.
Allocate time at the end of the offsite to align with the team on a handful of commitments. Set expectations that all participants will be held accountable, and track the team’s progress vs. commitments on a quarterly basis. Intervene when progress isn’t demonstrated and reward continuing efforts when they are.
Another approach to ensuring follow through is to establish champions who will hold the team accountable for certain commitments. For example, a media company’s leadership team developed new operating norms at their offsite to improve decision-making efficiency. To ensure the norms stuck, they assigned a “norms champion” for each team meeting—a rotating role responsible for monitoring adherence and gently calling out deviations. They also scheduled a 30-day follow-up session to reflect on what was working, adjust the norms, and reinforce their commitment. These steps helped embed the changes into their daily routines.
Offsites aren’t just a day away from the office—they’re an opportunity to reset your team’s trajectory. By focusing on these five questions, you’ll transform a routine gathering into a catalyst for meaningful change. Start with the end in mind, ask the right questions, and design and deliver an offsite that creates connection, clarity, and momentum so your team walks away primed to thrive.
Source: HBR
