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Nine Steps to a successful off-site leadership retreat

Take people off-site to meet unprecedented challenges and you will achieve what cannot be done otherwise.  We call such events leadership retreat, team development, strategy innovation, change management, scenario planning, and so on.  Original thinking is more likely away from familiar spaces that support the status quo.  Such spaces encourage people to leave behind their emotional baggage and develop new qualities of relationship.

Here are some points to consider that will help you make the most of going off-site:

  1. Start with the end in mind!

Imagine the desired state of play, maybe 3-5 years into the future: fresh working relationships, new roles and responsibilities, rich interactions, individual progress, collective outputs, a wave of change in the wider organisation and so on. Work back from that picture of success to the specific contribution of the initial off-site leadership retreat. Recognise that your off-site is not an isolated event but an essential foundation for an extended process of transformation.

Suppose you arrive at a description for your event such as: “We will bring people into relationship to resolve current issues, clarify our vision of what we are trying to achieve and our individual roles in that process. We will identify ways and means of delivering the results we aim for”. (Your own description may be more or less ambitious – wider or narrower in scope). It provides the context for the broad-brush design of your leadership retreat.

  1. Outline your event

As you begin to flesh out context and content, keep in mind your main purpose and outcome.  Consider who needs to be involved and when you can get them together.  What preparation is required and how much lead-in time is required?  Who will design and run the process? How long will you need?  What sort of ambience will be most productive?

The answers will not all arrive at once. Let the details of the event emerge slowly as ideas take shape. Do find out what has worked for others but don’t let what may have been sub-optimal in the past dictate the shape of your own process.

At some point you need to get down to detail. Determine the who, when, what, by whom, how long and where, of your leadership retreat.

  1. Who will design and facilitate?

The critical role of designing and running the event is best played by an external specialist facilitator. Internal facilitators are liable to “know what cannot be done” or be compromised by internal power politics. The greater degree of freedom enjoyed by externals can pay dividends before, during and after the leadership retreat. You need a facilitator who has sufficient:

  • experience to be able to grasp the niceties of your situation.
  • maturity to be able to handle the personalities involved
  • capability to design and manage the whole process.

Don’t expect them just to show up for the off-site itself. Employ them as early as you can and retain them until the whole process has run its course.

  1. What will be the focus?

A short residential event can enable you to achieve what is not otherwise possible – but you cannot achieve everything all at once. For instance you might clearly articulate a vision of success but the strategies to achieve it – and develop the team’s capacity to deliver – will require further work. Usually the off-site retreat will set up the conditions that sustain the rest of the process. Read, for instance, Serious Play. Once you are clear what the whole process is meant to achieve, identify the core focus of the leadership retreat itself and design accordingly.

  1. Who should be involved?

Make sure you involve everyone who needs to be involved. Don’t leave out people who really need to subscribe to whatever solution is devised. The “whole system” has a part in bringing about a change of perspective or whatever outcome you are after.  Of course there can be events of different scales; whole company, whole department; whole team and so on.

Rule out passengers (partners or guests) who will distract attention and introduce secondary motivations. They can easily render your leadership retreat meaningless. If you need to have VIPs witness what you are doing, keep their role ring-fenced.  Even though it may be useful to have some expert contributions early in the process or to present to board members towards the end, you should tread carefully lest you lose focus.

Most of what we call leadership retreats are relatively small in scale. There may be as few as six or as many as sixty participants (more usually 9 to 20). A critical feature is the opportunity to develop richly interactive relationships between the players.

  1. How long does it take?

Experience shows that spending a night together with colleagues, under the same roof, has a huge impact on outcomes. Two nights is better. Beyond three, you may get diminishing returns on the extra cost. There is a powerful social aspect to such events – almost their raison d’etre. As people come into relationship the quality of their thinking begins to change. Containment, intensity and good facilitation should bring about thinking that could not occur otherwise. A “change of level” and the awakening of aspiration is what makes leadership retreats a first-class investment. There should be time for relating, for thinking, for playing, for contact with nature and for driving out results.

Plan in plenty of time so the event is not compromised because of holidays or other commitments. Especially ensure your chosen facilitator and your ideal venue can accommodate you. Check these out before you finalise the date of your event.

Given the investment and logistics, it is very important that the event should not be too short. Aim for an absolute minimum of 36 hours and an optimum period in excess of 48 hours.  It is clear that the residential event is but one element in a much longer process. It starts with the first idea and will only be complete when the fruits are harvested. Thus a short leadership retreat actually has a life-span of around 12 months and may still be paying dividends several years into the future.

  1. Find the right venue

The choice of venue is a much more important factor than is usually allowed. Beware habitually choosing on price or convenience when other factors may be much more significant. A good venue will work around you and your requirements. Because it will actively contribute to your outcomes, your choice of venue will be one of the most significant factors in the success of your whole transformation process. Find an oasis of calm.

Going off-site should give your leadership retreat seclusion and containment.  Remember, an important aspect of being away together is to develop close and constructive relationships. They will enable you to address your issues from a new perspective with new energy. This requires you to have a place of your own.  It should give you beauty rather than luxury and encourage contact with nature. It should provide a complete contrast to your normal working environment and feed neglected aspects of perception.

Make sure you have flexible working spaces you can adapt to smaller and larger groupings and to formal and less formal interactions. Light and space matter. Be sure not to spend endless hours in a meeting room. There is no point in going off-site and working in habitual ways.  Dining together privately is a fundamental contributor to collective togetherness. It is important that colleagues meet to share their food – shielded from public gaze. There will be times when it is good to hold protracted conversations around the table. Other times you want meals to be swift.

  1. Follow-through

The follow through may span many months.  People pursue personal development goals, improve their teamwork, evolve strategies, form and implement plans, so measurable progress is made. This is not a separate process, but the continuation and bringing to fruition of the leadership retreat itself.

It will pay to retain your facilitator for this period. As this person successfully steered the off-site itself, their role naturally continues. They already have ownership of outcomes of the leadership retreat and now they can guide people to successful implementation. Your facilitator can support  further stages of the work and effectively challenge drift or avoidance. This can arise from the status quo ante re-asserting its pressures or a tendency to bow to new demands.

The facilitator acts as a kind of conscience for the work of the leadership retreat. This part of the process will typically comprise a pattern of remote contacts coupled with occasional on-site meetings and workshops for various sub-sets of people. Expect these to continue at least nine months after the leadership retreat.

  1. Budget!

Much of the cost of an off-site leadership retreat is that of executive salaries and travel.  Don’t allow marginal variations in costs of facilitation and venue to compromise quality of provision. Astoundingly, executive teams on an off-site might produce strategies that guide their organisations for several years to come. The miracle of this phenomenon should not obscure the hard work (and hard play) that surrounds it, nor the design and facilitation that make it possible. Every aspect of preparation and follow through will have made essential contributions to the final results.

You should be prepared to spend what it costs.  Don’t be seduced into unnecessary spending on reward, entertainment or adrenalin fuelled activities that do not contribute to (and might well detract from) the core process. Participants will be delighted that their work contributes to the progress of the organisation. You can share in celebrations at the right time.

But neither should you skimp on costs.  You can always find a cheaper facilitator – but do they have the capability? You can always find cheaper accommodation – but will it compromise your outcomes?


Leadership retreats bring about a change of level of thinking and relationship. You can make them the most important interactions in your organisation. What at first appears to be a short isolated event is in fact a vital foundation for a year-long process of transformation. Think about it this way and you will establish conditions for co-creation that will change your corporate trajectory and bring great rewards.


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