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13 Tips To Ensure A Productive Off-Site Leadership Strategy Retreat

Forbes Coaches Council

Many organizations hold off-site retreats for their leadership teams. Leadership strategy retreats are meant to provide a way for leaders throughout an organization to come together outside of the workplace, communicate and learn more about one another and the company while exploring ways to reach shared goals.

However, these sessions aren’t always as productive as they could be. Below, 13 members of Forbes Coaches Council discuss key aspects for planners to keep in mind to ensure they take the right approach and that their leadership strategy retreats are worthwhile.

1. Plan How You Will Take Action On Insights Gained

Too many leadership teams place all of their eggs in the “retreat basket.” Ensure sessions are productive by planning how to take action on the insights gained. If you find, for instance, that some leaders are not aligned with organizational values while others are challenged with execution, how will you address that day to day? Often, this is where ongoing executive coaching can help. - Nikita Allen, Growmetix

2. Have A Clear Goal And Record Action Steps

Companies should ensure that they have a clear outcome (goal) in mind and record clear action steps at the end of workshop days. Then, go straight into implementation. Ideally, they should take a small step in the direction discussed on the same day. - Björn Schnare, Xperience International GmbH (by Tobias Beck)

3. Set The Stage, Gather Data, Generate Insights

Off-site strategy retreats for leadership teams are great ways to engage the leadership and create team camaraderie. In my experience, what’s most effective is to start by setting the stage; this creates a shared understanding. The next step is gathering data and generating insights. After that, decide what to do next and close with actionable and committed improvements. - Nagesh Sharma, Flowsphere India Private Limited

4. Have An Outside Consultant Facilitate Feedback

Leadership retreats create an excellent opportunity to foster camaraderie, build trust and enhance communication. To be most effective, I recommend having an outside consultant facilitate the portions where feedback is elicited and deep discussion engaged in. This ensures that all members of the team are heard and helps keep any “overly strong” personalities at bay. (Every leadership team has them!) - Kristin Andree, Andree Group


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5. Facilitate Leaders Disconnecting From Their Normal Jobs

Leaders are always busy, and it is important for the participants to disconnect from their normal jobs to ensure these dedicated sessions are productive. As a planner, ensure that you facilitate leaders delegating and disconnecting in order to focus on the strategy retreat. - Luke Feldmeier, Online Leadership Training - Career and Leadership Accelerator for Engineers

6. Balance Strategic Planning, New Learning And Fun

It’s helpful to have a defined agenda that shows a balance of strategic planning, new learning and fun. Align your activities and sessions with your core values, creating opportunities to demonstrate what they may look like in action. For example, a focus on corporate social responsibility could include a beach cleanup by your team. Consider diversity when designing team engagement events and provide time for individual reflection. - Susan Murray, Clearpath Leadership

7. Balance The Personalities

I plan a lot of off-site advances (not retreats) for leadership councils at midsized professional service firms. The biggest determinant of success is who’s on the council. We limit these to seven people, and we balance personalities so that no one person dominates the conversation. It also helps to set expectations that everyone must talk. I call on the quiet ones to speak. - Randy Shattuck, The Shattuck Group

8. Focus On Energy Types, Balance Sessions

People focus a lot on personality types when they’re planning leadership retreats, but it’s also important to focus on “energy” types. A balance of activities and sessions that honor the different ways your leaders recharge their energy is essential to creating the best strategy. Without it, your people will start out with great intentions and lose their mojo well before the strategy is done. - Bronwen Sciortino, sheIQ Life Pty Ltd

9. Ensure A Deeper Focus On Human Connection

With in-person time so precious these days, don’t waste that time on anything that can be done virtually. Instead, ensure a deeper focus on human connection in developing team connectedness and plenty of deliberate time to really connect on the non-work stuff. I don’t think anyone wants to sit reviewing 100 PowerPoint slides anymore. Get up and get to know people. - Alex Draper, DX Learning Solutions

10. Start Energetically And Do Games Or Activities

Fun is key! There’s excitement and anticipation about going away to a retreat. Use some of the time to ensure people connect with one another through a game or activity, which will require the team to get to know their team members, especially those who came on during the pandemic. Retreats shouldn’t be all work and no play. Start the meeting energetically, and that energy will carry on throughout the day. - Kim Neeson, Kim Neeson Consultancy

11. Allow Time To Practice New Skills And Reflect

Many off-site retreats offer exciting new learning opportunities. However, it is also important to allow time to practice the new skills in simple demonstrations, as well as downtime for reflection. Offer time for leaders to debrief in smaller group settings to either teach the new skills to one another or debrief on what new insights they are eager to share once they return. - Kelly Huang, Coach Kelly Huang

12. Include Technology Breaks And Human Contact Breaks

Off-sites promise a distraction-free zone to facilitate clear thinking. Design technology breaks to eliminate electronic distractions from sessions and human contact breaks for enhanced collaboration. Provide professional facilitation incorporating good strategy process tools (discovery, clarification, problem-solving, dialogue and decision-making) to ensure a quality final work product. - Ron N Hurst, Developing Leaders

13. Create Structured Opportunities To Connect

One thing that is often missed is informal team-building time. I don’t mean trust falls, but I do mean creating structured opportunities for teammates to connect over activities and conversations that aren’t 100% job-function related. A solid agenda and goals are, of course, table stakes, but this informal bonding time is where team-building magic happens. Without it, why leave the conference room? - Randi Braun, Something Major

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