How to Plan a Successful Offsite: A Full Guide

Want to plan an offsite that leaves your team refreshed instead of drained? Here's everything you need to know.

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Ever come back from a team offsite feeling more tired than refreshed? You’re not alone. Many of us find it tricky to balance productivity with boosting team morale during these events. Over coffee, a friend shared her recent offsite experience with me, which left her exhausted instead of energized. This got me thinking about our upcoming Skye team offsite. How could we spend our four in-person days more effectively? 

Here’s everything we did to make our Skye team offsite a resounding (and energizing) success:

Pre-Offsite

1. Start with a Clear Purpose:

What do you want to achieve with the offsite? Are you looking to build relationships, brainstorm new ideas, or simply get away from the office? Defining a clear objective is key to creating an agenda that aligns with your goals.

2. Choose the Right Location:

Location matters — it can have a big impact on your offsite’s success. For example, if your goal is building relationships and interpersonal connection, choose a location that will allow people to relax and connect. If you’re brainstorming new ideas, choose a location that will inspire creativity.

3. Plan an Advanced Agenda:

Structure your days with distinct themes to save your team from context-switching fatigue. For example, we divided our offsite between days where we had a macro-focus (presentations by functional leaders on learning and strategy) and days where we had a micro-focus (learning from other leaders in Sales and Marketing to refine our GTM). Now is also a great time to zoom out and really think about big goals. Perhaps you want your team to learn a new skill, or get cross-functional leaders in a room to align on core strategy.

4. Include Interactive Sessions:

“Leadership development through coach-led workshops is no longer a luxury but a necessity for companies aiming to stay competitive in a fast-paced business environment.” – Forbes

We may be biased, but at Skye, we agree! We carved out time for coach-led workshops to address specific areas of growth for our team. Although we are a small team, we are remote, and cross-functional collaboration can become convoluted.

We hosted a Skye Labs on cross-functional teams and communication with Skye Coach Rohan, to create a framework and toolkit for remote, inter-team relationships.

5. Diversify Activities:

Combine productive work with fun! Mix up your agenda with both productive and enjoyable activities. We had pickleball, a couple of hikes and workouts in our offsite to keep the blood pumping! And of course, amazing dinners to keep us coming back for more.

6. Encourage Participation and Ownership:

Two weeks before the offsite, we assigned presentations to each leader, regardless of seniority. This included a presentation template and guidelines, making sure everyone understood the purpose and expectations.

During

1. Dedicate Structured Time for 1:1s:

Ensure interpersonal connections across departments with dedicated time for one-on-ones. Everyone had solo time with each other which helped with interpersonal connection across departments. We encouraged outside walks to ensure the team was present with each other.

2. Keep it Tech-Free (or to a minimum!):

Foster focused discussions by keeping distractions at bay. Phones and laptops were put away during team presentations. We had one designated note taker per meeting. Pen and paper are always welcome!

3. Discuss, Document, Rinse and Repeat:

Leverage technology for ongoing collaboration. We kept running a slack thread in which you could drop ideas, thoughts, concerns, questions that came up throughout the first 3 days.  The 4th day we took 2 hours to address each one, ensuring everyone was heard, loops were closed, and ideas recorded.

Post Offsite

1. Circle back and keep going

You’re back from your offsite and are (hopefully!)  filled with fresh inspiration, innovative ideas, and strategic visions. Now’s the perfect moment to keep that momentum going! Connect with your cross-functional colleagues to advance these ideas and transform your offsite insights into tangible results. It’s time to bring all that creativity and strategy to fruition in your daily work.

Coach-led Workshops for Offsites

Navigating team collaboration and skill development can be challenging. Coach-led workshops, as highlighted by industry leaders, offer effective pathways to enhance these dynamics.

Consider these insights:

  • Forbes highlights the importance of incorporating mindfulness and wellness into offsites, promoting overall team well-being.
  • Harvard Business Review suggests embracing ‘unplugged’ sessions, encouraging participants to disconnect from tech for more meaningful, focused interactions.
  • An interesting approach from both Harvard Business Review and Forbes is ‘reverse mentoring.’ This strategy allows younger team members to share insights with senior colleagues, creating a unique, collaborative learning environment.

Planning a successful offsite is no small feat, but Skye Labs offers a well-rounded solution. Our curated workshops are tailored to develop essential skills, boost team collaboration, and drive collective success. By integrating these expert strategies with Skye Labs’ seasoned guidance, your next offsite is poised to make a memorable and transformative impact.

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