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Expectation Management: The Key to Successful Corporate Retreats

Expectation Management: The Key to Successful Corporate Retreats

January 31, 2025
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“Expect the worst, and you'll never be disappointed,” say the pessimists.
Whether you see the glass half full or half empty, expectations are a natural human instinct that is hard to control or ignore. Managing them, though, is possible, and we have found it to be a fast track to success when organising all types of events, especially corporate retreats. 

In this piece, we explore expectation management, its crucial role in hosting events, and its importance in organising successful team retreats. 


What is expectation management?

Expectation management is, first, about understanding and then guiding and then about adapting what people anticipate during a project, event or interaction. 


For that, a few essential steps are necessary: 

  • Open and transparent two-way communication: The project leaders need to share information early on and listen to the comments and feedback from the project participants. 
  • Involving stakeholders: The individuals impacted by the project need to be included in the corporate retreat planning as much as possible to understand the retreat goals and constraints better and ensure “buy-in.” 
  • Realistic goal-setting: based on the first exchanges, the retreat goals need to be aligned with the available resources and current constraints of the team/company
  • Continuous monitoring: Communication needs to continue throughout the planning, the event itself, and after that. It is not a one-time task. 

Why is expectation management important?

A person holds a microphone, standing at a lectern with a laptop, speaking to an attentive audience seated at tables in a room with wooden accents.

Neglecting expectation management can be painful, whether in a personal setting (relationship, family) or a professional one (within a team or a company). 

Ambiguity and uncertainty from misaligned expectations usually lead to confusion and frustration, which can lead to inefficiency. 

This is caused over time by lower morale and self-esteem in employees, increased distrust of management, and an increased number of conflicts within the organisation. 

On the other hand, teams that can properly manage expectations notice several positive impacts.

Expectation management and team dynamics

In the same way that aiming for unachievable personal goals can set you up for disappointment, managing group and individual expectations is crucial for fostering effective team dynamics.
It will directly impact several key challenges all teams encounter:

Clear Directions

Knowing what is expected from them helps team members better understand their roles and responsibilities, making it easier for them to deliver with confidence. This leads to improved performance and a nonnegligible sense of empowerment.

Two people sit at a wooden table, engaged in conversation with a laptop open between them. The setting is a warmly lit room with large windows and potted plants.

Reducing Miscommunication

Miscommunication is the mother of frustration, eventually leading to resentment and conflicts among team members. To avoid that, it is best to set clear expectations from the start and ensure everyone is aware of them and aligned on how to reach them.  

Promoting Accountability

When expectations are clear, accountability increases. 

Feeling empowered makes it easier for team members to take ownership of their work, boosting personal and team performance. 

Building Trust

When everyone is clear on what needs to be done and who is responsible for what, it is much easier to start trusting each other. Setting expectations helps create structure, consistency, and stability, which in turn enhances the feeling of psychological safety within a team.

People sitting at a conference table work on laptops and discuss while viewing a large screen displaying a webpage. Bright room with natural light filtered through blinds.

Improving Morale

Failure to meet expectations will make your team frustrated and disengaged in the long run. In contrast, a team meeting and/or exceeding expectations will make them feel more satisfied and motivated. Not only is it essential to set realistic expectations, but it is also essential to celebrate them when they are met! 

Adaptability

As projects advance, expectations might shift. Regular updates and check-ins are important to ensure everyone is on the same page and kept in the progress loop. 

Why is expectation management critical for team retreats?

People using laptops, seated and standing, in a cozy room with modern furniture and sheer curtains. A television and shelf with items are in the background.

If you thought expectations management was only essential at the [home] office, think again. 

While corporate team retreats can be extremely rewarding, nothing creates a broader range of expectations in employees than the idea of going to a new location for a few days.
From fun to fear, business to pleasure, they all have their own idea of what a team retreat should/will/can be. 

Your offsite meetings require careful expectation management to ensure the right team dynamic is established from the get-go. 

Diverse Expectations

As mentioned above, your team members may have vastly different expectations for that retreat. After all, the term retreat can be understood as a time to relax, a time to reflect, a time to unwind or disconnect, a time to bond, or a chance to dive into a specific project without day-to-day distractions. Team building, strategy sessions, problem-solving, What will it be? It is essential that you clear that out from the moment you announce your retreat, or you will face misalignment.

Potential for Misalignment

When there is a need for clarity, people tend to project their own expectations of the event. This sets you up for disappointment and confusion when your team realises it is not what they thought it would be. You will struggle to bounce back and engage your team as you want to.

A person speaks in front of a small group, pointing at a projected presentation titled "Owner: Andreas" in a wooden room. Nearby are a laptop and blank flip chart.

Impact on the team dynamics

While you aim to bring your team closer together with your retreat, failing to manage expectations will have the opposite results: misunderstandings about the event itself and the goals can lead to resentment, frustration, decreased employee engagement and morale, tension, and no follow-through post retreats. 

Jeopardising ROI 

All in all, forgetting to address expectations jeopardises the whole event. Organising a successful team retreat demands a high investment, whether in terms of time or finances. Understandably, the stakes are relatively high. Neglecting expectation management would endanger the return on investment of the whole event.
This will also have implications in the long term, as future retreats might be much harder to promote and probably face gossip and cynicism from the team.

How to properly manage expectations before a team retreat?

Four men are sitting at a conference table, smiling and engaged, with notebooks and laptops in front of them. The room has a bright, casual setting with natural light.


Here are some of our most essential tips when it comes to managing your team’s expectations ahead of your retreat: 

Set clear objectives and goals

We have probably repeated this enough by now: setting realistic expectations for team retreats is key. Focus on one or two main ones so you don't overwhelm yourself and try to cram too much during the retreat. 

Have a balanced schedule

It is tempting to include as much as possible during those few days to “get the most out of it,” but in reality, the way to get there is to have a balanced schedule with dedicated workshops times, team building sessions, rest & reflection times as well as some free time during which unexpected magical moment can happen. 

Communicate!

Another point we have been repeating throughout this piece: never stop communicating with your team.
Keep them informed before the retreat, plan for daily reminders and check-ins during the gathering, open up for suggestions, and follow up after the event. 

Three people sit on the grass in a garden, engaged in conversation. A green hedge and bushes surround them, creating a peaceful, outdoor setting.

Consider the individual as part of the team 

Effective management involves addressing both individual and team expectations:

Sometimes, group dynamics can be misleading when it comes to managing expectations. Someone who feels less comfortable voicing their opinion in front of others might not share their feedback or suggestions in a group setting. Consider having one-on-one or pre and post-event surveys, think about the different types of personalities in your group (early birds/night owl, extrovert/introvert…) 

Be flexible 

The one thing to expect for sure is that it will only sometimes be exactly as you planned. Be open to review, iterate and accommodate your team members’ needs while adapting the schedule based on emerging needs (from your team or other circumstances such as weather or space availability) 

Follow-up

After organising a team retreat, it is easy to go home and feel like your work is done. Many make the mistake of forgetting to follow up and miss out on a lot of learning.
While it is important to give your team a few days to settle back in and integrate, have a check-in follow-up meeting the following week or a feedback survey to learn what went well and what could be improved for next time. 

Hopefully, this piece gives you a good understanding of the importance of expectations management and its impact on team dynamics and corporate team retreats before, during, and after the event. Managing expectations is part of corporate retreat best practices and is not solely about informing but about engaging your team, receiving feedback, and communicating clearly and consistently before, during, and after the event. 

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