Facilitating a leadership retreat … 2023-style


Over the past few months, I’ve had the pleasure of facilitating several executive and leadership retreats. Most of these sessions have been focused on supporting senior teams through leading and communicating change related to new hybrid approaches to work. 

Without exception, these leadership sessions have been engaging, fascinating and refreshing. On a personal level, having the opportunity to work with leaders in-person has been particularly nourishing, especially after the isolation of the pandemic and the haze of endless Zoom sessions. Professionally, I have found navigating groups through new ways of gathering and leading totally energizing (okay, and quite exhausting, too). 

I’ve received many requests to share observations and tips from the trenches in leading such facilitated sessions, so here goes – the top 10 things I’ve learned so far about facilitating leadership retreats 2023-style:

  1. People have forgotten how to do immersive in-person sessions. The pandemic has dismantled many of our cultural and workplace norms. This is causing a pervasive low-grade anxiety and disorientation (as I wrote about in my piece on WTF is going on?). That means that hosting a successful retreat requires significant preparation and careful design – don’t assume anything, including that people will show up with a pen. 
  1. Clear is kind. As a result of the disorientation of our new ways of working, it’s especially important to carefully design sessions from the vantage point of the participant, being attentive to ensuring that the experience throughout its life cycle (before, during and after) is positive, coherent and crystal clear. Executives are depleted from leading a workforce through the largest disruption to work since the industrial revolution. It’s important to be extremely clear about the session objectives, logistics and expectations. This is part of providing more signal and less noise in the organization, particularly at the top where information overload has become crippling.  Leaders want to contribute and do their best – it’s kind to provide them with guardrails so that ambiguity is reduced and they can show up effectively. I find this is best done by preparing a detailed participant package including a gearing up page for preparation, detailed objectives and agenda, as well as recommended readings/resources.
  1. Design for the intellectual and the emotional experience. The magic of a retreat that delivers lasting and breakthrough results is in designing the event to maximize intellectual and emotional impact. The emotional dimension is generally under-treated but it’s an absolute pre-condition to an effective business outcome. A good place to start is to ask the executive sponsor for the event “at the end of the retreat, how do you want our senior leaders to feel?”. This is particularly important in the current environment in which there is enormous value in executives convening and building a sense of community with solidarity of intent. The reverse is also true: if the executive retreat has an anxious, cynical or conflictual vibe, it will choke the best ideas right out of the room. 
  1. Focus on value. I always tell clients that the cost of a team retreat isn’t so much in facilitation fees, but in the opportunity cost of their leaders’ time, energy and mental space. I often work with the full senior executive team of an organization, for full days at a time. If 10 minutes is wasted because a breakout exercise instruction isn’t clearly understood, that’s a huge price tag when considering the value of 40 or 50 executives’ time. What’s worse is that executives are generally (appropriately) impatient and exacting in their standards – if they feel that a program component is irrelevant or misaligned to their priorities you risk losing their attention, energy and focus. That’s why the ratio of time for executive session design to delivery is usually about five or six to one. To be candid, we also hear of concerns about the cost of executive sessions, to which I would ask: what is the cost of having an executive team that is misaligned, disengaged or working at cross purposes? 
  1. The devil is in the details. This one I’ve learned the hard way: make no assumptions and leave nothing to chance. From clarity in the meeting invitation, validating who should participate, setting up room logistics and planning a tight program based on laser-focused exercises supported by clear instructions. 
  1. Form should follow function. If your leadership retreat is focused on a return to the office, then it has to be an in-person session. Full stop. Similarly, if a retreat is planned as a way to build cohesion among leaders across the organization (which is often the case given the silos calcified through the pandemic), then care should be taken to assign seating and mix up the participants by function and level. If the goal is to deliver a high energy, memorable experience, the design has to match that aim – I find that inserting regular breaks and a lot of movement in a session is critical to success. (Interestingly, I’d observe that before the pandemic, executives would routinely sit through very long all day sessions. Now I notice that by 2 or 3 o’clock many are standing and are more comfortable participating and engaging while moving around).
  1. Think in terms of bursts. In the context of the attention economy and hyperactive hive mind of most executives’ day-to-day work, Shopify’s concept of “bursts” is helpful. The idea is to host short, tight, brief sessions that pack a punch. I have found that we generate better results out of carefully planned shorter days (often 9:30 – 3:30) such that participants can focus completely and yet still have time and energy left in the day to attend to email and other priorities.  
  1. Consider hybrid models carefully. While I am finding that in-person sessions are far superior for executive team building and alignment, in some cases a hybrid model is necessary. If that’s the case, I would follow Priya Parker’s Art of Gathering advice and identify a “centre of gravity” for the session. That is, if the centre of gravity is to be in the room, then the experience is primarily designed with that intent – that means that online participation is possible, but is treated in a secondary fashion. Conversely, we’ve also done sessions built on Miro as a collaborative white board tool in which the online experience becomes the default priority. There should be an intentional decision at the outset about the priority space for the session because it’s impossible to deliver an exemplary experience both online and in person online. If you’re considering a hybrid model, keep in mind that you’re effectively working in three spaces at once – in the room, online, and the interplay between the two. I can tell you that if you’re also doing this in a bilingual format, this gets very complicated and challenging quickly! In my experience, a hybrid retreat calls for at least double the time to design a session effectively and definitely requires a dedicated “buddy” to manage the online experience. It’s also worth noting that the structure of the day has to be modified to make hybrid work – I have never seen a full-day online session in which participants were fully engaged and it’s delusional to think that a participant will watch a screen all day without being drawn away by the siren call of email. 
  1. Make technology work for you. There are many ways in which technology can derail your leadership retreats – we are all familiar with the common technology fails related to projection and mics. There are also new challenges on the horizon now, particularly in hybrid sessions. A team retreat delivered in hybrid requires quality, stable audio and visual connection between all participants in the room as well as those participating remotely. This is trickier than it sounds and I’ve seen many A/V technicians break into a cold sweat realizing that the camera angles and mic set ups just don’t work as advertised. More insidious is that some of the cool technology we now rely on such as Owl aren’t yet second nature and participants need coaching on using them effectively – one massive pitfall is that the Owl system picks up ambient sound remarkably well, which may cause awkward moments when remote participants hear side-bar conversations from the room inadvertently. Another consideration is that if you want a truly rich, in-person experience, declaring the room digital-free is probably the best thing you can do – that means that exercises are best done using worksheets or wall exercises. The minute you refer executives to online tools or breakout instructions sent electronically, you can viscerally feel you’ve lost them to their inbox. 
  1. Ensure effective follow-up. If your executives have devoted a day or two of their time in a retreat, it’s imperative that it not be a one-shot wonder. This is particularly true in the current environment in which employees generally and leaders particularly expect value for their investment of time in meetings. I find it valuable to consider the lifecycle of a retreat – zooming into the expected outcomes and then intentionally designing the session to deliver. This might include a session report, a 30-60-90 day action plan or a list of follow-ups. Assigning a specific role for capturing the group’s input is critical, and is often a surprisingly demanding task. It’s worth deliberately mapping out next steps after the retreat – that should include closing the loop with participants and also being attentive to the non-participants (let’s face it, if all the bosses are meeting for a day or two, employees will be left wondering what’s going on). I’ve found that considering a cadence of predictable leadership sessions is often helpful, particularly as a source of stability and reinforcement of executives during a period of high disruption and change. 

This is an important and meaningful time to convene leaders in powerful exercises of alignment, rejuvenation, connection and change readiness. I consider it an honour to have the privilege of working with inspiring leaders in a retreat setting. It’s certainly the most demanding work I do – but also the most energizing.

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