10 Lessons learned for running a great Product and UX Offsite

Planning a successful Product and UX offsite is crucial for fostering collaboration, aligning on strategy, and igniting creativity within your team. Offsites provide a valuable opportunity for team members to step away from their daily routines, reflect on past successes and challenges, and chart a course for future innovation. However, ensuring these gatherings are productive and inspiring requires thoughtful planning and execution. In this article, I’ll explore the key steps to leading an effective Product and UX offsite that maximizes engagement, encourages open dialogue, and drives actionable outcomes. From setting clear objectives to creating an inclusive environment, I’ll provide actionable insights to help you make your next offsite a resounding success.

1. Get executive buy-in

   Nothing will happen without this step, so start here! Draft a high level agenda and budget for your offsite. It doesn’t need to be overly detailed, but it should definitely speak to how many people you want to attend, the number of days (ours was 4 and it felt like just the right amount), and budget (we estimated about $1000 per person for travel and hotel but that was definitely not enough so round up).

2. Identify the expected outcomes

   Understand what it is you want to see come out of this offsite. For me, the goal of this offsite was to drive alignment on product vision, strategy, and get down to the tactical level of what should we focus on in Q3/Q4. You need a tangible output otherwise the purpose will get muddy along the way.

3. Create an agenda that tells a story

   Creating the agenda was the toughest task. I wanted each day to have a flow to it and take my team on a journey rather than jumping around to different topics. Before I got started, I sent a survey to my team to get an understanding of what their pain points and hopes were out of this offsite. Gathering their feedback was critical. From there, I focused on the product development life cycle.

   • I started with Product Culture. We did a retrospective exercise to talk through what’s working well and what’s not. Instead of using sticky-notes like I have in the past, we leveraged a tool called Lucid Spark to capture all of our thoughts and ideas which was amazing. No one had to take pictures and transcribe our notes later on.

   • Next we focused on Product Vision. The team expressed a lack of alignment with our overall vision. The company has been growing rapidly, which is amazing, but we are also struggling to keep a grasp on the north star as we acquire and grow our business. I invited my Chief Product Officer to join virtually and walk us through his vision. I also had him capture this in writing before hand and shared it out as pre-reading material.

   • From there, we dove into Product Strategy - the heart of our offsite. I gave examples of companies that have created extremely effective product strategies as a starter (like SouthWest Airlines) and showed how they played to win. We talked a lot about what a product strategy is not (e.g. an organized list of features) before we explored how we could prioritize our goals to meet the business objectives. We spent the most time discussing a prioritized set of problems to solve as a group and the impact those have on each one of our product solutions. Our biggest challenge has been each team working in a silo. While we all on paper knew what the priorities were, we weren’t leveraging the knowledge of the group to think through deep reaching solutions. This was the most impactful time we spent together!

4. Do as many pre-work activities before getting to the offsite as you can

   At the offsite, we spent a good amount of time on retrospective activities that could have easily been done before we were in person. This was a big takeaway for me that next time I will front load this work so that when we arrive at the offsite we can spend our time discussing everyones feedback versus spending time gathering it.

5. Leave a half day at the end open for wrapping up loose ends

   This was a life saver for me. I intentionally left the last day of our offsite completely agenda free to leave room for anything that we needed to parking lot earlier and roll over. I’m so glad I did this because we needed it!

6. Outsource some portion of the agenda to other team members

   It is a lot of work to plan an offsite and also be the sole presenter - Don’t do this to yourself! People don’t want to hear one person monologue on for 4 days straight. Asking other team members to present specific sessions is a great way to spread the load and bring other unique perspectives to the table. In my case, I asked my Lead Product Manager to prepare a session on conducting Customer Discovery Sessions that was excellent. Him and I recently took the SVPG Product Masterclass and were able to share many of the best practices and lessons learned from there. In this case, he didn’t have to do a lot of research to prepare. Our goal was to up level the skills of the whole team and share our collective learnings.

   Next, I asked my Head of UX to do a session on Working with UX Designers. Often times, teams can slip back into bad habits when it comes to communicating requirements and I had seen this happening especially when it came to collaborating with UX. Some PM’s tend to dictate design solutions rather than leveraging the skills of our talented UX members to come up with new ideas and ways of testing designs, so this session was a great opportunity to remind everyone how we can all best work together.

7. Leverage help from your events team

   Do not sleep on this one! The best thing I could have done was lean on the expertise of my events team to help me coordinate meeting space and a room block. Negotiating with the hotel and supplying them with all our necessary paperwork was definitely a part of the offsite that I did not have on my radar. Once I brought someone in from my events team she was able to quickly help me identify potential locations to host our offsite, source quotes from different hotels, build a more accurate budget including F&B, find cool restaurant and bar recommendations, and handled all major travel logistics. It was a life saver! After all, I still had my actual job on top of being a travel planner for 11 people.

8. Team building activities should shine. Make them memorable. Team dinners don’t count in my opinion.

   I joked with my team, but I definitely spent a big chunk of time figuring out the extracurricular activities and it sometimes outweighed my focus on the agenda. Don’t worry, I definitely put my energy there BUT I knew that the greatest opportunity for my team to bond and form strong relationships was in the things we did in the off hours. And as my title says - team dinners don’t count! Why? Because having a conversation over a meal is typically bounded by the 3-4 people you sit near and let’s be honest, most people try to sit next to people they already know.

   For my team, I wanted 2 things… First, an activity that was unique to the city we were traveling to (something you might only have the opportunity to do if you are visiting) and two an activity that was outside. We all sit inside behind our screens all day, so getting some Vitamin D was a must. Since I was trying to be budget conscious I opted to forgo a team dinner and use those funds towards an activity. We sub’d a formal dinner for a beer garden on our way to go see an off-broadway show in New York. If you haven’t seen Titanique The Musical I highly recommend you run and not walk to go see it! The the other activity I planned was an e-bike tour of Central Park. It was such a fun way to be outside, learn some history, and “exercise” without having to break a sweat.

9. Be a facilitator, not a hero.

   Before going into the offsite, I watched a few Youtube videos on how to run and facilitate an effective meeting. I’m a big proponent of not reinventing the wheel so I wanted to learn from those who had already been down this path. The most important take away I found was that your job as the leader of the offsite is to be a facilitator and not a hero - what does that mean? It means your role is not to be the star of the show. Your job is to guide, lead, and help the team have meaningful discussions as a group. It is not to hear yourself talk on a soap box for hours on end. Maybe this seems obvious but I needed to hear this! It helped remove some of the anxiety I had about keeping 11 people focused for 4 days because it was about keeping the conversation going and not about showing how well I can entertain everyone. Less content - more open discussion.

10. Follow through on Action items

    Literally nothing is worse than spending a few days with your team away from your normal tasks, having great discussions, and then there is no follow through. I’ve been to many offsite’s like this and I can’t tell you how frustrating it feels. Why even bother? But this is by far the hardest part of the entire offsite… figuring out how to turn amazing, tough topics and ideas into real, tangible action items. Spend the time to do this and so everyone keeps coming back for more!