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Effective Facilitation Strategies for Conducting Your Company's Annual Strategy Workshop

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The first and fourth quarters of each year, for me, as for any other facilitator, represent a period of intense activity when all clients urgently require the preparation and execution of annual sessions of a different scale (from a team size to up to hundreds of participants). Most often, these are sessions of the next types: team retrospective, company gathering, annual strategy meeting, leadership retreat, or annual planning.

I recently conducted an overall company offsite annual strategic session. It occurred to me that not all companies currently have the budget for an external facilitator, and thus the responsibility of preparing and conducting such sessions falls on the shoulders of the company's employees (like ScrumMasters or Agile Coaches and I talked about facilitation a lot in my article called Just Another Typical Work Week of a ScrumMaster). Hence, this post aims to alleviate the plight of these employees by highlighting the key points of preparation and risks.

  1. Identify the primary client of the session
    Often, the person who approached you with the request is not the initiator of this request, and you initially receive a distorted message - this could lead to the situation where this initiator appears during the session and expresses their surprise in a rather direct manner. Moreover, sometimes you will receive entire chains of the format "this is needed by that person → this is needed by this person → here's who really needs it". And such chains can lead all the way to the company's CEO. Your task is to reach the real initiator and discuss important matters with them.

  2. Learn from the primary client not only the request but also the reason for the request and the surrounding context
    Very often, what is asked for reminds one of the phrase attributed to Henry Ford: "If I had asked people what they wanted, they would have asked for a faster horse." You will have to conduct a mini-investigation on the topic of the request to understand that a horse is not needed, but a car. And sometimes you may find yourself in a situation where you don't need to conduct a session, but initiate, for example, organisational coaching (I often come to this point when the request is "Anton, we need an OKR session").

  3. Identify all influencers of the session
    As you navigate through the chain of people from the points above, be sure to ask, "Who else should I talk to about this topic?," "Who else is this important to?," and "Who will this session affect?" You need to communicate with all these people - they will provide even more context, suggest who else to talk to, and also you will address their request, which will increase your chances of them not disrupting your session.

  4. Assess the achievability of the session's goals within the agreed-upon constraints
    Often, the initial request may sound like "Product brainstorming session for 15 people, for 8 hours, online". After steps 1, 2 and 3, it can easily turn into "Strategic session on repositioning the business in 2024 for 50+ people... for 8 hours online". That is, the complexity of the session has increased significantly, but the constraints remain the same. Your duty, as a facilitator, is to assess whether it is indeed possible to achieve real value within the given constraints and if not, to discuss their changes up to the refusal of the request. I repeat - it is your professional and ethical duty to say that this request cannot be done within the given constraints. Then, you should strive for those constraints within which this can be done. In my example, the initial request was for a 3-day online session, and I convinced the client to change this point. During the first coffee break, one of the key clients approached me and said, "Anton, I'm trying to imagine this session online, and it gives me the shivers."

  5. Try to redefine the constraints to the level of maximum achievable awesomeness
    Here we are talking not about the minimum necessary, but about its upgrade. If there is even a tiny possibility to make not 2 days, but 3 - strive for this. If there is even a tiny possibility to make the session offline - strive for this. If there is even a tiny possibility to do this by the sea - strive for this. All these extra-plus features are your future mitigators of potential risks, all of which are impossible to predict. Also, these are often the moments that distinguish a good session from a fantastic one.

  6. Never skimp on space
    If you worked well at step # 4, then you most likely have an offline session. Congratulations! Now do everything possible to ensure you don't get a space less than 1 square meter per person, with ceilings lower than 2.5m (once I really got such a space), immovable tables, walls where stickers can't be stuck, lack of oxygen, high levels of CO2, and a non-working air conditioner. The space is your main co-facilitator - it should take your breath away. By the way Jurgen Appelo created a wonderful Jurgen's Checklist for Workshop Organizers that covers this topic in more details.

  7. And certainly, do not skimp on the small things
    Again, if you worked well at step # 4, you will need stickers, markers, and other facilitation tools. There is nothing worse than poorly writing markers and stickers falling off the walls. I either fiercely micromanage the client up to the point of "send me a photo of the ordered materials", or I carry (as was the case in this trip) a 20kg suitcase of materials I trust.

  8. Do not divide each day into too many minor activities
    The vast majority of novice facilitators are guilty of one big problem - they try to pack as many activities as possible into each day. Usually, this looks like a super detailed plan in the form of "17 minutes for activity # 1, 14 minutes for activity # 2... 15 minutes for activity # 37 and end of the day exactly 11.5 minutes long". They can be understood - I was like that myself. Such a plan creates a sense of session control for the facilitator, and therefore safety. But such a plan also exhausts the participants and does not allow for spontaneity and transition to a deep flow state, where deep insights are born and group synergy lives. Yes, this puts more strain on the facilitator, but our primary goal is to help the group.

  9. More with less
    I love this saying from the Large Scale Scrum community - it applies both to describing the right organizational design and to preparing a good facilitation session. In this case, we are talking about the duration of each session. Again, a common mistake of novice facilitators is to have 4 hours in the morning (with a micro coffee break inside), then an hour for lunch and another 4 hours non-stop (with a micro coffee break inside). After all, it seems that if 50+ people were brought to one location, they must now work to the maximum, which they will do for the first 3 hours of the first day, the first 2 hours of the second, and 1.5 hours of the third, and the rest of the time they will try to produce obvious things with non-working brains. The nature of intellectual work is such that the proverbial deep flow state cannot be maintained by many hours of work (according to the author of the book Deep Work, most office workers have completely lost this ability and it requires many months of recovery). It's even harder to do this in a group. We need to take these points into account, which means no 8 hours a day! Here's what the schedule of my session looked like: 1.5 hours of work + 0.5-hour coffee break + 1.5 hours of work + 2.5-hour lunch break + 1.5 hours of work + 0.5-hour coffee break + 1.5 hours of work. Participants were pleasantly surprised by the state of their brains at the end of the day and some even wanted to switch to this format on a daily basis. And the 2.5-hour lunch break allowed for a walk in the sun, a swim in the sea, and a power nap.

  10. Be prepared for everything to go not as planned
    I deliberately did not focus on the topic of how to create group activities, which techniques to use, how to organize transition bridges from activity A to activity B, how to organize mini-groups and help them enter different states (expanding thinking, cross-pollination, critical perception points, focus on decision-making, etc.). There are two reasons. The first: there is a lot of excellent literature on this topic (I recommend starting with Facilitator's Guide to Participatory Decision-Making by Sam Kaner). The second reason: you, as a facilitator, must be prepared for the fact that in 2 hours all your painstakingly prepared facilitation script can be thrown out. The dynamics in any large group can at any moment move into the complex-domain (hello Cynefin Framework) and you need to be prepared for this. Examples: someone received an urgent letter about aggressive merger in the market, some conflict manifested itself, or just during one of the group deep flow sessions something came up that became more important than everything planned in advance. As Josh Magro likes to say, "We follow the script until something better shows up". For this, you need to learn how to "read" the group in the process, synchronize with the main customer from point 1 during coffee breaks, and be ready to rebuild the session on the fly or even do the facilitator's nightmare - freestyle. Our task is not to drag people through a non-working script, but to help them achieve the global goals of the session or... to new goals that were found in the process. Isn't this the true calling of a facilitator!
And that's all for today. I wish you more systematics in matters of organizational design.

Do more with less and may the force be with you!
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