How to run an offsite with lasting impact

How to run a team offsite with lasting impact

If the words “team offsite” send a shiver down your spine and conjure up images of cringe-worthy trust exercises, hours of powerpoint slides or incessant navel-gazing and psychological mumbo-jumbo, you’re certainly not alone. We’ve all experienced the horrors of a poorly planned team away day, resulting in a soon to be forgotten experience and a wasted opportunity to come together, connect and tackle problems collectively. 

Over recent years we have become increasingly disconnected from our colleagues. Technology designed to improve productivity is removing human interaction and opportunity for true collaboration and discourse. And with hybrid working practices now becoming the norm, the time we do spend with colleagues is more precious than ever. In this article we take a look at why team offsites so often fail to have a meaningful impact, why this sacred in-person time needs to be approached differently in a digital, hybrid world and how you can build a transformational offsite space that integrates strategic, relational, creative and practical agendas to catalyse meaningful change.

The objectives of a leadership offsite

Team offsites have always been an opportunity to take a step away from the day-to-day, to zoom out and focus on the big strategic questions and challenges that are ultimately going to have the biggest impact on your organisation. In today’s environment of increasing volatility, complexity and uncertainty, however, leaders face three types of challenges which make leadership offsites more critical than ever to sustained business success:

  1. Strategic: Disruptive change requires organisations to adapt their business model or how they compete in the marketplace. These kind of challenges cannot be solved solely through a functional perspective, via reductive analysis (splitting a problem into parts). They first require creative synthesis and collective innovation, by the team learning to think as a cohesive unit..
  1. Relational: Market disruption and business model adaptation can affect established ways of working and relationships between departments and levels. This can create tensions and conflict between members of the leadership team. To meet the challenge of disruptive change, leadership teams need to be able to surface and address relational issues productively, as well as the rational or technical problems. 
  1. Executional: In today’s fast-changing environment, it is not possible to fix long-term transformation plans in advance. More often than not, by the time the organisation comes to execute on the plan the team has devised, the external environment will have shifted. To meet this challenge, leadership teams need collective agility: the ability to “turn on a dime” or “build the plane while it is flying”.

For these reasons, being able to design and run an effective leadership team offsite is more critical to sustained success than ever before. Unfortunately teams often fail to make progress from the outset, either because the team misunderstands the real purpose of a leadership offsite, or because the fundamental foundations are not in place ahead of an offsite session .

Turning the group into a team

Before undertaking an offsite, it is important to differentiate the two functions that a leadership team needs to perform, in order to be successful. Understanding this at the outset is critical to designing an effective offsite. Leadership teams need to operate in two distinct modes, with different approaches to meeting design and group dynamics, by working as both a functional workgroup and a transformational team.

Firstly, leadership “teams” need to function as an efficient workgroup. Your leadership group are likely deeply talented domain experts in their field, As a workgroup, they need to meet on a regular basis to manage the operational agenda. These meetings are formal in nature, have tightly defined agendas and are focused on taking decisive action to address roadblocks. When group members attend, they wear their functional hat, with the emphasis being on escalating and addressing roadblocks and overlap issues with other functions. These meetings are chaired by the leader, who exerts their authority as the formal “boss”, in the event of a tie. It is important to note that we do not want to diminish the importance of this workgroup role in any way in this article, since it is a critical component of business success.

In today’s environment, however, leadership groups need to be able to balance working in this way with the ability to be a real leadership team. And this, in our experience, is where most senior executive teams (and therefore transformation efforts) struggle. Virtually every leadership team today faces complex transformational challenges. To solve them they need the ability to work as a cohesive team, as well as being an efficient workgroup. The primary purpose of a leadership offsite is therefore to develop and apply the teamwork at the top needed to meet the challenge of complex change. Whereas a workgroup is focused on reductive analysis and decision-making, teamwork is about solving creative synthesis and collective innovation.

This is a different landscape that leadership teams need to learn to navigate together. When designing the agenda for a leadership team offsite, it is not possible to design the perfect timetable in advance. Complex, adaptive challenges have no predictable answers or established solutions. Instead, team members to take off their functional hats to think creatively about the organisation as a whole. And, as new information and perspectives come to light, they need to be able to adapt and refine their ways of working accordingly. From the team leader’s perspective, it requires them to function more as a partner, coach and facilitator of group dynamics, in order to develop the real commitment and shared leadership needed to succeed.

Common mistakes – and how to overcome them

One of the most common mistakes we see is the failure to create a real sense of belonging, or common identity, within the leadership team. Because most leaders are more comfortable working in an environment where they have control, they tend to view the team they lead as their “first team” rather than the leadership team upon which they sit. As a result, team members dedicate more energy and time focusing on what is going on in their own area with their own teams, rather than how the executive team as a whole is performing. Leaders need to be proactive in this regard, by building esprit de corps, while also focusing the team on their collective purpose, setting clear expectations and holding them collectively accountable. 

The second big mistake we see is failing to create the psychological safety needed for team members to really say what they think and feel. When a leader is running a workgroup, they need to exert formal authority, chairing the conversation and making clear decisions in the event of a stalemate. When it comes to teamwork, however, the leader needs to minimise this power difference, ensuring team members feel safe enough to surface any “elephants in the room” and express their real opinions, even if these differ from other people’s. In virtually every team we work with, the leader tells us upon engagement that they know what their team members really think and feel. Psychological safety is crucial for breakthrough team performance. Many teams will say that they don’t give each other the feedback they need to because the group dynamic don’t feel psychologically safe. Yet paradoxically the opposite is also true: when group members are able to provide open feedback to one another in a respectful manner, this creates psychological safety.

Finally, the third big mistake we see is overfilling offsite agendas, or focusing on the wrong kind of activity. One common issue is wasting valuable face-to-face time to listen to Powerpoint presentations. In an increasingly virtual working environment, face-to-face time is too valuable to waste in this way, with one way downloads like this better suited to virtual pre-briefings before the meeting itself. A second error we see often is overfilling an offsite agenda by trying to tackle too many topics at once, often by throwing in a whole load of tactical operational issues, to the detriment of the critical strategic topic the team should be focusing on. When this happens, topics end up being rushed though, meaning the crucial issues or elephants in the room that need addressing to create breakthrough performance end up being “taken offline” or even bumped from the agenda entirely. 

Designing and running a team offsite – the head, heart and hands of collective intelligence

At Living Systems, we have developed a tried and tested approach to designing and running leadership team offsites. We should emphasise that our work stands upon the shoulders of a number of giants in this field, most notably Otto Scharmer’s Theory U approach and Bill Isaacs work on dialogue. In our experience, an effective team offsite involves a general flow through four distinct phases of conversation: collective inquiry, relational dialogue, co-creation and collective action. We call these stages the head, heart, left hand and right hand of collective intelligence, respectively. As per Otto Scharmer’s original model, we also describe at as U-process of conversation, with the left hand side of the U signifying a deeper inquiry to better understand the challenge, before then rising up the right hand side to then solve it:

As already mentioned, when a leadership team arrives at an offsite, it needs a clear focus and coherent set of objectives for the offsite. With this clear framing for the offsite, the first phase of discussion needs to be a process of collective inquiry: understanding the diversity of perspectives and opinions of different team members related to the strategic issue being discussed. All too often teams rush into action and don’t spend the time needed in this phase to give each topic the time and attention needed to discuss it adequately, ensure all voices are heard and understood, and achieve clarity and consensus on the way forward. As a result, teams fail to uncover catalytic collective insight and change plans end up delivering incremental, rather than breakthrough, innovation.

When a team has the conversational effectiveness to truly surface the diversity of opinions and feelings of its members, polarities tend to emerge. Conflict which has hitherto been unexpressed can rise to the surface, as a result. As this happens, teams need to engage in a process of relational dialogue. This requires the team to shift from the rational to the relational agenda: surfacing unexpressed conflict or “elephants in the room” and then addressing it effectively. Team members need to be able to “cook the conflict”, regulating the temperature so it doesn’t get too hot, while also ensuring it doesn’t get so cold that that the conversation goes cold (and people don’t say what they really think or feel). To do this, team members need to be able to tolerate a productive level of discomfort, as well as have the toolkit needed to manage and resolve conflict creatively.

It is only once this process of collective awareness and increasing connectivity has been achieved within the team that it is then capable of genuine co-creation together. And while countless studies have shown the importance of creative problem solving techniques to business innovation, it is remarkable to us how few leadership teams avail themselves of these techniques. At Living Systems, we use a variety of creativity and design thinking practices to help teams uncover new paradigms and ways of thinking about their adaptive challenge, before then seeking to translate into more rational and linear ways of turning into action. 

Once a team has moved through these three initial phases, we generally find that three things have been accomplished. Firstly, team members understand and empathise with the diversity of perspectives in the team. This transforms understanding and collective insight. Secondly, by speaking openly with each other trust and performance is enhanced within the team, leading to bolder and more creative collective problem-solving. Finally, by engaging in creative exploration together at this stage, they are now able to uncover genuine new paradigms and ways of thinking, creating the conditions for collective breakthrough. At this point the team is finally able to move into the final stage of collective action: translating a high level vision or idea into an actionable plan, by breaking the solution into pieces, assigning owners and establishing a governance and rhythm of workgroup and team meetings to sustain progress, refine and adapt efforts along the way. 

In conclusion

In this paper we have set out why team offsites are more critical than ever before to business success, some of the common mistakes we see in designing and running offsites, as well as a high level process for solving tough problems together. This approach requires a different mindset and set of skills to the more formal workgroup approach most leaders are familiar with. In an era where leadership teams face greater volatility and more complex problems, however, it is rapidly becoming a key differentiator between success and failure.

At this point it is worthwhile mentioning the value of external facilitation. In order to enable all team members to focus fully on the discussions at hand, many teams choose to bring in an external facilitator for their offsite. By managing the process of the meeting, a facilitator enables the leader of the team to work alongside their team members and focus on helping solve the problem, rather than having to run it. They are entirely unbiased and therefore able to challenge assumptions, manage conflict situations, bring fresh perspectives and ask the difficult questions. Finally, since a good facilitator’s core expertise is in the field of leadership team effectiveness, they are also able to develop the capability of team members, while working on the problem at the same time.

Get in touch with the Living Systems team today to find out how we can help your leadership team take collective performance to another level