Before you book that leadership retreat, ask yourself this...

As the year draws to a close, many organizations are preparing for their annual leadership retreats. Some have already held theirs, while others are still planning, with November and December traditionally being popular months for these gatherings. Leadership retreats offer an opportunity to step away from daily demands, celebrate achievements, reflect on challenges and make decisions about the future. Yet, having facilitated retreats and worked with leadership teams, I have learned that bringing leaders together does not automatically mean they will have the conversations they need to have.

On the first day, discussions can be quite diplomatic. Leaders present achievements, acknowledge challenges and contribute to discussions while carefully navigating issues that everyone seems to know about but nobody is ready to name. Towards the end of the second day, or even on the last day, things begin to change. Someone finally raises a concern that has affected collaboration for months. Another questions a decision everyone appeared to support.

A leader admits that their team has been struggling with expectations they never believed were realistic. The room can become tense. People may become defensive, and the facilitator has to help the team stay with the conversation rather than retreat into familiar positions. I value these moments because they often bring us closer to the real issues. They also leave me wondering how much further the team could have gone if that openness had been possible from the first day. Are we preparing for the conversations our organization needs, or simply preparing an agenda?

What do we need to understand before bringing everyone together?

Organizations invest considerable effort in preparing performance reports, developing agendas, and agreeing on expected outcomes. I believe equal attention should go into understanding what is really happening within the leadership team before deciding what the retreat should address. Amy Edmondson's research on psychological safety and Elizabeth Morrison's work on employee silence reinforce something I have observed while facilitating retreats: having something to say and feeling comfortable enough to say it are two different things. This is why I encourage organizations to consider an independent assessment before their retreat, creating an opportunity for leaders and other relevant stakeholders to share their perspectives confidentially.

What is working well? Where is collaboration breaking down? Which conversations have been avoided? What concerns are people reluctant to raise? Where do leaders feel unsupported?

Through individual conversations, surveys, or other appropriate approaches, an assessment can reveal issues that might otherwise surface too late. It should also identify strengths, achievements and practices worth preserving, because not every retreat needs to begin with a problem.

The findings should influence the agenda, the conversations that receive attention, and how participants prepare. If your organization already does this, kudos! The next question is whether those insights genuinely shape what happens during the retreat.

Are we willing to have the uncomfortable conversations?

Consider a leadership team where the commercial department repeatedly commits to delivery timelines that operations cannot meet. Sales believes operations is holding back growth, while operations believes sales makes promises without understanding what delivery requires. Both departments have legitimate concerns. At the retreat, each could present its performance, explain its challenges, and commit to improving collaboration. Yet the underlying problem could remain untouched. The more useful conversation would examine how decisions are made, where consultation is missing, what assumptions the departments hold about each other, and how their leaders have contributed to the situation. These conversations require honesty without humiliation, accountability without blame, and enough trust for leaders to acknowledge their own contribution. The facilitator's role is not to eliminate discomfort or push people towards premature agreement, but to help them work through difficult issues constructively. When that conversation only begins an hour before the retreat ends, the opportunity to explore its implications is limited. Good preparation gives it a better chance of happening earlier.

Will our leaders leave saying "we" or "they"?

One statement I find revealing when discussing organizational decisions with leaders is: "We are doing this because that is what they want." Who are they? The CEO, the board, senior management or a funding partner? A leadership team can spend several days developing a strategy, agreeing on priorities and assigning responsibilities, yet return to their departments speaking about those decisions as though they belong to somebody else. Imagine an organization deciding to expand significantly over the next two years. One department head knows their team is already struggling with existing responsibilities and has concerns about staffing, systems and the proposed pace of expansion. They participate in the discussions and agree with the direction, but their concerns are never fully examined. A few weeks later, their team hears, "Management wants us to achieve these targets."

The retreat produced agreement, but did it produce alignment? Alignment does not mean everyone gets their preferred decision. It means leaders understand the direction, have had a meaningful opportunity to contribute, recognise how their responsibilities connect to the broader ambition and understand what delivering it will require.

It also means considering the people behind those responsibilities. Do they have the capabilities, authority and support to succeed? How does the direction connect with their own professional growth? What will it require them to change about how they lead?

I would want leaders to leave able to explain why the organization's direction matters, what their contribution will be and what support they can count on.

Are we looking far enough, and making the right choices?

A retreat should also help leaders examine whether their strategy remains relevant to the environment in which the organization operates. Consider an organization planning to expand a service that has performed well for several years. The financial projections are promising, and the leadership team believes there is room for growth.

Before committing, however, have they considered changing customer needs, developments within their ecosystem, relevant national priorities and international trends that could affect the service's future? I believe alignment should extend from the individual leader to the team, across the organization and into the wider environment.

Internally, strategy needs to connect with capabilities, resources, systems, culture and leadership practices. Externally, it needs to reflect the realities of customers, communities, partners and the broader environment. Understanding these connections helps leaders make informed choices rather than pursuing opportunities simply because they appear attractive.

This is particularly important when every department arrives with initiatives worth pursuing. An organization may want to grow its market share, strengthen internal systems, improve customer experience, expand into new locations, and invest in staff development. All are reasonable ambitions, but resources and capacity are not unlimited.

Which priorities deserve investment now? What should wait? What needs to stop? What trade-offs are leaders prepared to make? I would rather see a leadership team leave with fewer, well-considered priorities that people understand and can realistically pursue than an impressive list nobody has the capacity to deliver.

What support will people receive after the retreat?

The quality of a retreat becomes clearer in the months that follow. Responsibilities may be assigned, and timelines agreed, but leaders return to operational pressures and dependencies that can make implementation difficult. Research published in Harvard Business Review found that only 9% of managers surveyed could consistently rely on colleagues in other functions to fulfil their commitments. That is worth considering when so many strategic priorities depend on departments working together.

Imagine a department head who commits to delivering a major initiative within six months. Three months later, progress is behind schedule because recruitment approval is pending, another department has not provided essential information and unexpected operational demands have stretched the team.

At the next management meeting, the leader is asked to explain the delay. That is a legitimate accountability conversation, but it should go further. What decisions could unblock progress? What support has not materialized? Have circumstances changed? What responsibility do other leaders have in helping this department succeed?

We should be careful about treating strategic commitments as though they belong exclusively to the person whose name appears next to them in an action plan. The same applies when retreats identify leadership development needs. If leaders need to delegate better, manage conflict differently, or improve communication, what support will help them develop those capabilities afterwards?

Regular check-ins should create opportunities to review progress, remove obstacles, revisit assumptions, and address performance concerns constructively.

Holding people accountable and supporting them to succeed should not be competing responsibilities.

Before the next retreat, what should we do differently?

I would begin by looking back at the previous retreat, not only at the commitments made but also at what happened to the people expected to deliver them. Did leaders become more aligned? Did collaboration improve? Were difficult conversations followed by meaningful changes? Did people receive the support they needed? What did the organization learn, and what deserves celebrating? I would then encourage an independent assessment before finalising the next agenda, so that the retreat responds to what people and the organization genuinely need. During the retreat, I would want leaders to confront their realities, examine their assumptions, make deliberate strategic choices and understand how their individual and collective contributions fit into the bigger picture.

Afterwards, I would want to see those conversations continue through meaningful follow-up, leadership development, shared accountability and practical support. Above all, I would want people to leave knowing their voices mattered, that they understand their contribution and that they will not be left alone to figure out how to deliver. A retreat should strengthen the people and relationships through which the strategy will be delivered, not only produce a plan for them to implement. So, before you book that leadership retreat, here is the question I would leave you with:

What needs to happen before, during and after this retreat for your people and your organization to be more aligned, better equipped and genuinely ready to deliver on what matters?