Running strategy sessions in a virtual world

August 25, 2021

Of all the meetings executives go to in a year, none is more important than the strategic planning offsite. This is where the most essential conversations for the future of the organization occur.

Given the number of companies increasingly adopting remote work, strategic planning retreats have also gone virtual. With people from a leadership team scattered across locations and time zones, will remote strategy sessions be as effective? We believe so. Virtual sessions can match and sometimes exceed in person ones.

Our firm has conducted several dozen workshops and strategic planning sessions in the past year and a half. In this post, we will share our field guide to running a remote session and some useful tactics as well as the pros & cons when choosing to run a virtual session.

Field guide for remote strategy sessions

Whether a company is fully remote or in person, remote sessions have inexorably become part of the tool kit for a management team to master.

Here are our top facilitation & workshop design best practices:

  • Stick to meeting basics. Prior to the strategy workshop, set clear objectives, and send a pre-read if appropriate. During the session, use an agenda, set meeting ground rules, take breaks, and clearly outline next steps (including timing and accountabilities) after each section and at the end of the meeting.
  • State the ground rules at the beginning of the day. It’s good to remind everyone to be engaged, respectful, contribute to the discussion, and avoid getting distracted. Setting ground rules is key to avoiding multitasking and creating a focused session.
  • Four hours per day is a good amount of time for a virtual offsite. Being on zoom all day is tiring! Two consecutive four-hour days are recommended. Expect to get through about four sessions each day, with three 15-minute breaks.

Staff these roles, One person can’t do it all. We recommend staffing these roles otherwise, it is too demanding on the facilitator’s attention:

  • Facilitator – runs the meeting
  • Chat Watcher – watches chat console and alerts facilitator of requests from meeting participants
  • Timekeeper – watches clock and alerts attendees when allotted time is running out
  • Notetaker – establish who will take the notes and consider it a group responsibility if possible


In many ways, remote sessions can be more powerful than in person ones. Here are our top arguments for hosting virtual strategy sessions.

  • Input from more people. Prior to the strategic planning offsite, remote sessions offer the ability to quickly gather feedback from a larger number of stakeholders. This leads to better quality inputs for the offsite.
  • Robust tracking. Recording and note taking make it easy to keep track of what was discussed. Post-mortem review of the content of the session can generate insights on how certain decisions were made.
  • Better inclusivity. This is the biggest advantage of holding a remote session. In a typical in person meeting, the leaders that win their points are usually the ones who are the most charismatic and eloquently deliver their argument. This doesn’t always mean they have the best ideas. Virtual sessions reduce biases by using collaborative tools, breakout rooms and techniques like Think, Write, Share. The last one has been particularly effective where we ask a leadership team to write down their ideas and then share in a round table.


Remote sessions are not perfect and sometimes not desirable. There are certain situations where high bandwidth communication is better, particularly during a crisis or an urgent situation. In normal circumstances, there are key disadvantages to be aware of.

  • Potential to be less fluid and cohesive. Team cohesion and alignment are necessary for a successful strategy offsite. They are the building blocks of making sustainable decisions for an organisation. If a remote session is sloppy and not as well managed, it’s difficult to hold these tense conversations.
  • Potential to be more tiring if the sessions are not well designed. Zoom fatigue is real. If the strategy sessions are not well designed, they have the potential to be tiring for participants.
  • Less team building opportunities. There’s a reason why the term “breaking bread together” exists, people like people. Strong bonds emerge when people have spent time together in person with shared experiences. It’s important to include physical gatherings when possible. Even fully remote companies like Automattic hold an annual in person meetup for the entire company to see each other in person.

The future of work is already here

Remote work is already the most talked about subject about work and will remain top of mind for leaders for years to come. One thing we know is true is that remote work is here to stay. Companies will adopt remote work in some fashion.

Strategy offsites remain an important part of leading a successful business and they also need to adapt to this new reality. We hope that these tips & tricks will help you run better remote strategic planning sessions.

You can download our full guide here