Three Things You Can Do Ahead of Time to Make the Most of Your Leadership Team Offsite

Leadership offsites are an invaluable opportunity to build trust, create clarity, and drive alignment. So, as People leaders, how do we make the most out of the opportunity? 

Joy Sybesma
Founder & CEO, ScaleJoy


Offsites are high-stakes events. They are expensive, both in the cost of the event itself and the time away from day-to-day work. It’s never been a harder time to ask employees to get on a plane and leave their families. Getting together to bond just doesn’t cut it anymore. Offsites need to be thoughtfully planned to drive the business forward, all in 2 to 3 days!

At the same time, offsites are an invaluable opportunity to build trust, create clarity, and drive alignment. We value in-person time more than ever before because it has been so rare for the last two years. And, with the Great Resignation showing no signs of slowing, it’s never been more important to show intentional, empathetic leadership. The impact of the offsite goes beyond the event itself. Done well, the process and practice designing the offsite can shape your leadership team, providing opportunities for deeper reflection and engagement with their teams.

So, as People leaders, how do we make the most out of the opportunity? 


Figure out your own role to play in the off-site.

Chief People Officers rightly expect that they will hold a lot of responsibility for offsites. It’s true, but not in the way you might think. 

When I was a CPO, I remember wheeling a giant wood frame whiteboard down 14th Street to go to an offsite. We’d realized at the last minute that we needed one and I jumped into action. As I was navigating the bumps in the sidewalk, I asked myself why I was the one who everyone — myself included — expected would handle it? I was a leader within the company, and this was an administrative responsibility. What lack of boundaries allowed this to happen? But if I was honest with myself, carrying the “event planner” burden was my happy place, I was safe there. But what roles couldn’t I play while playing admin?

It’s easy to lean into being helpful, but as a result, what do you lean out of?

You need to ask yourself what your role is in the off-site and why. As a People leader, you should be representing your function. Being in charge of administration and facilitation takes you out of that role. 

The fix? Bring in outside players to help you. An off-site requires event planning, business strategy, and attention-to-detail. If you and the rest of your leadership team can step away from the details, you’ll be able to focus on the work that only you can do — and ideally outsource the whiteboard transportation.


Prepare with intention.

Done well, offsites require a lot of pre-work from the leadership team. Being intentional about the agenda will help employees understand the value of the off-site, but more than that, this intentionality and clarity of vision will help them understand how their work fits within greater company goals. Making sure everyone is on the same page when they arrive, ready to contribute, is inclusivity in action. Everyone deserves to feel valued and respected in the workplace. Leadership teams committing to this pre-work is one way to signal that acknowledgement and respect. Sharing the agenda and pre-reads ahead of time is modeling that respect. 

Once you’ve established roles and responsibilities, define the purpose and objective of the off-site by answering the following two questions: Why are we bringing this group together, and what is our actual need?


These questions will allow you to build consensus with your team on the purpose and definition of success. It’s unlikely that you will have the time to do everything, and realistically, most ambitious goals take more than a few days to achieve. Clarifying priorities and keeping your bigger purpose at the center will both help you get the most out of your off-site and guide the tactical steps to get there.


Once you’ve articulated your goals and objectives, start designing the offsite to meet the agreed-upon needs and purpose. This is where an external partner can be really helpful. They can help bridge the gap between intention and plan, providing strategic frameworks, defining OKRs, and planning communication strategies. 

Whether it’s an external partner or your People team at the helm, make sure everyone has clear marching orders to prepare for the off-site. In order to achieve your objectives, what work needs to be done prior? Consider the following:

  • What information needs to be gathered?
  • What content needs to be created? 
  • What do participants need to pre-read to be on the same page for a discussion?

Finally, make sure all participants know what to expect by laying out rules of engagement. Every company has different norms, but your rules should answer questions like “Am I able to be on my computer?” and “Are we committed to starting and ending each session on time?” 

Together, this pre-planning can ensure co-creation and buy-in from all participants before the event even starts. 


Assess psychological safety.

Pre-planning is one key ingredient in creating a successful offsite. The second is psychological safety. Psychological safety at work is how comfortable employees feel speaking up without fear of rejection. Based on organizational trust and interpersonal respect, psychological safety manifests in employees challenging norms or leadership, sharing innovative ideas, and not shying away from productive disagreement. 

There are four stages of psychological safety as defined by Timothy R Clarke in his book The Four Stages Of Psychological Safety:

  • Inclusion Safety – members feel safe to belong to the team. They are comfortable being present, do not feel excluded, and feel like they are wanted and appreciated.
  • Learner Safety – members are able to learn through asking questions. Team members here may be able to experiment, make (and admit) small mistakes, and ask for help.
  • Contributor Safety – members feel safe to contribute their own ideas, without fear of embarrassment or ridicule. This is a more challenging state, because volunteering your own ideas can increase the psychosocial vulnerability of team members.
  • Challenger Safety – members can question others’ (including those in authority) ideas or suggest significant changes to ideas, plans, or ways of working.


As a People leader, I’ve found that most CEOs believe their whole team is at the challenger safety stage, but it’s important to go directly to the employees and ask their point of view. If we find something contrary in our pre-surveys, we work to reset leadership expectations. Psychological safety doesn’t change overnight, but knowing about it can affect how you think about goals and outcomes. 
Ultimately, most of the offsite is about building psychological safety rather than realizing the fruits of it.

During the offsite, there are active strategies you can take to build psychological safety. 

  • Validate individuals and invite them to share their expertise.
  • Acknowledge the newer members of the team and ask what you can do to set them up for success.
  • Be explicit about expectations.
  • Make sure everyone has the same information going into the event.
  • Don’t be afraid to ask employees explicitly what your company can do to make them feel safe enough to level up. 


Why it matters

Planning for offsites with this level of care has ripple effects beyond the explicit goals. The framework you create for the yearly meeting can be used not just for future offsites but scaled down for quarterly, monthly, and weekly meetings as well. And, the preparation itself can illuminate gaps in process and culture. The investment of time and energy is significant, but done right, offsites will make lasting change in your organization and set every single employee up for success.

Want to connect with Joy and her work at ScaleJoy, connect via Hello@troophr.com.

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