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A Successful Leadership Retreat Requires These 4 Things

An offsite leadership retreat is a great time for leaders to get away from everyday pressures, get some through some serious planning and strategizing, and maybe have a little fun while they’re at it. Finding the time to invest in this type of event can be difficult, so it’s important to make the most of the opportunity. Here are the four key elements that make for a successful leadership offsite:

An Objective

Without a clear focus on a desired outcome, a leadership retreat won’t achieve what you need it to. Maybe your leaders will return to the office feeling a little bit refreshed from a few days offsite, but it’s more likely that they will be frustrated at wasting their time, or worse, it could drive wedges into relationships when people are made to sit through days of meetings with no clear purpose. So before you pick a date for the annual leadership retreat, figure out why you’re having it in the first place.

You can do this by sitting down with senior sales executives and other leaders who are ultimately accountable for the event. Talk about what they are looking to achieve by having the retreat. Why are they bringing the leaders all together? What is the main purpose, and what do they want everyone to return to work with? Once you have defined the main objective and perhaps a few sub-points, then you can begin thinking about the specifics of the event agenda.


Regardless of the objective for the leadership retreat, it’s vital to create alignment among the leaders in attendance. When you send out the agenda prior to the retreat, it should include a clear statement of the goals, along with any pre-planning or work you need leaders to prepare.

Then, to open the retreat, the retreat leader – whether that’s the CEO, senior sales executive, or a professional facilitator – should lead a discussion or an activity to ensure that everyone is on the same page. Since the top leaders at any company will have different – and sometimes competing – priorities and perspectives, they might not be coming to the retreat with the same goals. Together, attendees should come to an agreement on what they will achieve, and a definition of what success will look like at the end of the retreat. This is an opportunity for truthful discussions and brainstorming about the business, so it’s important to establish a safe space that encourages healthy debate, not just rubber-stamping things to get it over with.

Throughout the leadership retreat, the leader of the event should circle back to the established definition of success and track progress, summarizing decisions that have been made and ensuring the alignment that was created is intact.


The only way the objective can be successfully achieved and alignment maintained is by ensuring that all of the attendees are engaged throughout the retreat. This is part of the reason leadership retreats are held offsite – it minimizes distractions and provides a change of scenery to help people to think creatively. But removing distractions alone isn’t enough to ensure that leaders remain engaged. It helps to have a variety of interactive sessions and experiential activities to get people moving. Getting people out of their comfort zones and engaged in an experiential activity can be eye opening, and prime the leadership team to come up with innovative ideas and new solutions. These types of activities are also great for developing skills such as leadership, communication, effective delegation, and problem solving, so it could be a great time to add time for professional development.

Using different types of activities throughout the leadership retreat not only keeps things interesting, it also ensures that everyone gets the chance to contribute. Shaking up the way the conversations happens appeals to multiple styles of thinking and inspires creativity, innovation, and problem-solving. This ensures that everyone, regardless of the way they approach problems, will feel included and stay engaged with the process.


No matter what comes out of the leadership retreat, it can only be completely successful if leaders actually implement the ideas that were brought forward and agreed to be actioned on. At the end of each session throughout the retreat, the decisions that were made and action items that were identified should be agreed on and recorded. At the closing of the retreat, the leader should recap everything that was accomplished, and facilitate a discussion on how the team will follow up on each item. After everyone has returned to work, the plan that was developed should be sent out with names and deadlines attached to each item. This way, nothing slips through the cracks post-event and everyone is held accountable for what they agreed to do.

Planning an effective leadership retreat begins with getting clear on why you’re having the retreat in the first place, getting all of your attendees in alignment about what they need to accomplish, keeping everyone engaged throughout, then making sure the outcomes translate into action back at work. If you can do all of that, your executive team will be excited about what they can accomplish during their time out of the office, as well as what it means for the year ahead.


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