After more than two years of working virtually or remotely, offices are filling up again as employers seek to bring their workforce back to the workplace in the hopes of fostering a healthy yet sustainable work-life environment. 

In the same breath, as work becomes more in-person again, leadership and executive retreats, a staple of the corporate world, have been reimagined to help companies and organizations tackle unique problems, brainstorm ideas, and help generate a forward-looking vision for the company. 

In the past, executive retreats were considered an expensive waste of company funds. Though the pandemic made it easier and a lot more affordable to take the retreat virtually, with the workplace now redefined and with younger generations filling up executive seats, the facilitation of a leadership retreat will need to be reimagined to help teams establish a dynamic, yet functional understanding of each other and the organization. 

What are Leadership Retreats for Executives?

Leadership retreats for executives have developed into several new formats over the last couple of years, as organizations look to make these getaways more valuable and sustainable for both participants and the company. 

More so, these retreats take place over several days, usually involving the CEO and executive team members convening outside the traditional office space. The time used on these retreats is typically allocated in a way to help teams become more connected and boost their natural abilities to support and understand the organization’s forward-looking goals. 

The last few years of the pandemic have brought to light that some companies and organizations have been pouring endless amounts of cash into executive leadership retreats that didn’t make a significant difference to their organizational structure or help them achieve their goals more effectively. 

Ever since, it has meant that companies have been cutting back on excessive spending on executive retreats, and introducing newer and more diverse team-building strategies. On the other side of things, it’s also true that when a company has a clear goal, and all employees can channel their productivity towards that goal, these retreats can become valuable getaways for not just executives, but mid and junior-level employees as well.

Why Organize a Company Retreat?

When starting a strategic planning retreats or organizing a company retreat, it would require you or any of the planners involved to consider the ‘why’ factor to help better understand the reasoning behind these excursions. 

These retreats should be seen as more than a paid getaway for employees or a break away from the company and the day-to-day activities of the business. More so, it should be considered a time when executives can effectively collaborate through meaningful conversations, and team-building exercises to boost company morale, and help to better understand the company’s forward-looking guidance. 

On top of this, it’s also worthwhile to consider how both the company and team objectives will be playing a big part in the overall success of the retreat. 

Company retreats should have a balance between work and play and depending on the size of the company, the budget, and the organizational structure, planners should set clear objectives right from the start to help them and the leadership team better understand what they want to get out of the excursion. 

Having a good enough reason that will support the company, its development, and improve cross-functional teamwork, and improve the overall decision-making process will better help planners and CEOs understand how to structure a company retreat and how it will bring more value to the overall company. 

Retreat Goals and Objectives

During the planning process, it’s important to have clear-cut goals and objectives that will drive the conversation before, during, and after the retreat. 

Not only that, but it’s also important to know the difference between having goals and objectives, and when strategic planning retreats, distinguishing between these two would help improve the outcomes and value metric of the retreat. 

Setting goals will help leaders better understand who their employees are, and how they can build on their skills or improve the qualities they already have. Goals may also include things like creating a more vibrant work culture, bringing leadership team members closer to one another, or what to look out for in future hires. 

Retreat objectives, on the other hand, may include aspects such as resolving a business issue or overcoming any challenge. Helping executive teams build a better sense of communication between each other while also forging better connections between members who are geographically dispersed. Objectives tend to look at what the team structure is, or project may be and how certain activities can help fine-tune or improve cross-functional teamwork. 

Once you have identified the primary goal and objective, planning becomes a lot easier. More so, it means that companies better understand how their employee’s function and what they require in the workplace to achieve overarching business goals. 

On-site vs Virtual Leadership Retreats

Planning a leadership retreat looks a lot different than what it did a few decades ago due to the advent of technology and the digital workplace. It’s now become a lot easier to have a leadership team join in on a retreat, even if they are not in the same location. Better yet, it’s also become a more affordable and sustainable solution for some businesses that are willing to host a retreat but do not necessarily have the financial resources to pay for elaborate employee getaways. 

When planning whether a retreat should be virtual or in-person, it mostly depends on the organizational structure, and whether team members will be able to converse in the same location if they are working remotely. 

For virtual-only retreats, it could help to create an event that suits all team members’ schedules, more so, it should also be at a suitable time that doesn’t necessarily interfere with their work or personal obligations. 

Hosting a virtual retreat is a more comfortable way of getting all team members involved, especially for those that are not directly in contact with any other members of the company. On the flip side, it might be considered that although these virtual retreats can offer a more sustainable business model, there are those members that would value in-person retreats every now and again to help boost focus groups and reinforce the company’s vision.

For on-site or in-person retreats, the case may be different, and this would require the company to have some resources already available to support and fund the employee getaway. On top of this, it would take a bit more planning and strategy building to ensure that the company and team members can get the most out of the money and time they have invested. 

The final decision, on whether on-site or virtual retreats are a more suitable choice ultimately comes down to budget, employee location, and preference. Additionally, it’s also important for planners and CEOs to take into consideration what employees want to get the most out of the retreat and how the company will be able to capitalize on these employee getaways. 

How to Plan a Retreat

The overall planning process requires a bit of ingenuity and research to ensure all employees’ needs are met, and that enough time is allocated to help employees resolve a specific problem or develop better cross-functional communication. 

During the planning process, it’s best to keep the goals and objectives of the retreat at hand, as this will help stimulate a better understanding of what to include in the retreat and how much value the company will be getting out of the employee getaway. 

Set a Goal and Objectives

As already mentioned, it’s important to have goals and objectives clearly outlined as this would make it easier for both planners and team members to understand what they can expect, and what might be expected of them after the retreat has come to an end. 

Have a Defined Budget

A budget will help to clearly outline the amount of resources the company has available to put together an employee retreat. More so, it’s a way for the company to curb irresponsible spending, and having a budget means that every member will get the best possible benefit from the budget spent on the retreat. 

Consider the Retreat Format

The next step is to consider the format of the event, which includes particulars such as the number of days, any specific dates, and whether it will be taking place on-site or virtually. Depending on the budget, each corporate retreat will look different and will consist of several activities. 

If you do require employees to attend an on-site retreat, it would mean that planners should consider the location, accommodation, transportation, and any other expenses that will help enhance the overall experience. It’s best at this stage to consider what the overall goals and objectives of the retreat are, and how the format can fit in with it. 

Consider Employee Schedules

Though several members will be attending the retreat, not all of them work on the same type of schedule, as some may have work or personal obligations they need to attend to. The best way to minimize excessive schedule or date changes is to send out a possible date of the retreat to employees who will be attending, and require them to approve or decline the chosen date. 

If you notice that more employees cannot attend, it’s best to start changing some dates around that could be more suitable for work and personal schedules. 

Choose a Location

If you end up planning an on-site retreat, start looking for places or locations. Remember that if you already have a budget at hand, you will be able to look for places within your range that also meet the primary goal of the retreat. In some instances, it would be best to choose a location based on where employees are located, as you also need to factor in transportation to and from the retreat. 

Keep Attendees Informed

Once most of the planning has been completed and a list of those that will be attending has been compiled, it’s important to keep employees well-informed leading up to the event. Make sure that all those attending know when and where the retreat is, what they can expect, and what the format of the retreat will look like. 

Additionally, you can include a rundown of the retreat and how activities will be scheduled. The best is to make sure that attendees have an idea of what they can expect and what is expected of them during this time to avoid disappointment.

Check Out 5 Tips for a Successful Leadership Retreat:

Leadership Retreat Ideas

Planning a leadership retreat is more than working on finding the right format for the company and those that will be attending. There’s also a part of the planning process that requires planners to think of activity ideas to help keep employees engaged at all times. 

Retreat Ideas for Small Groups

For smaller groups, it’s best to plan something a bit more intimate and relaxing, that does not require too much time or resources from the company. It can be something simple, like going for a company picnic, or even taking a hike at a national park. 

Small group retreats can also be more successful if the company organized an event that includes exciting activities such as a scavenger hunt, incorporating employee communication through an online escape room, or orchestrating activities that can help attendees think more creatively and effectively communicate. 

Retreat Ideas for Large Groups

Larger groups are often a bit harder to plan for, as this requires both a lot of resources and meticulous scheduling skills. For a larger retreat group, a getaway to a pre-planned location may be more suitable, as this brings attendees together in an intimate space, outside of the workplace. 

Another idea could be to invite a guest speaker, which can help to stimulate conversations around a specific topic or problem. For larger groups, it’s best to consider group-based activities that will divide attendees into smaller groups which can ultimately help them communicate more effectively, and get to know each other better. 

Leadership Retreat Agenda Sample

Planning the retreat agenda oversees several aspects of the company retreat and helps employees have a better idea of what will be expected of them during the retreat. 

On the agenda, you can include ice-breaker activities that will help to introduce employees to one another. It’s important also to include some skill-building sessions, which divide employees into smaller groups where they can get to know one another better. 

Activities that follow afterward could be more centered around a specific problem or project that requires employees to resolve either within their groups or individually. 

There should also be time allocated where employees are allowed to network with one another less professionally. In the same breath, working in some wellness activities can help employees feel more relaxed while their creativity is being stimulated. 

What to Bring to a Work Retreat

Packing for a retreat will never look the same for every person as it mostly depends on the event, the location, and what activities employees will be attending over the weekend. 

As a general guide, it’s best to pack the following: 

  • Formal and informal attire 
  • Bathroom toiletries 
  • Athleisure wear
  • Comfortable shoes 
  • Office supplies i.e. book and pen 
  • Electronics 
  • Any additional resources outlined in the retreat guideline


What Are 4 Strategies for Strengthening Teams?

– Having a thoughtful leader
– Ensuring and establishing a primary goal.
– Setting clear guidelines for completion
– Building open channels of communication

How Do You Facilitate an Executive Retreat?

Make sure to budget and plan properly, and be clear about the retreat objectives. Additionally, the schedule is key and requires planners to consider employees’ work and personal obligations. Be mindful of what is required of employees during this time, and ensure that there is a primary goal to help bring employees closer and forge better cross-functional communication. 

How Do You Run an Executive Retreat?

Consider what the needs of the company are and how the retreat will fit in with the company’s goals and objectives. Secondly, be mindful of the company culture and how this should play a part in the planning process. Make time for employees to relax, and ensure that each of them is comfortable while also making a direct contribution to the company’s goals. 

How Do You Structure a Leadership Retreat?

Be clear about what employees can expect and what will be expected of them before, during, and after the retreat. Have a well-thought plan that includes ideas from several aspects of the company, and ensure it aligns with the company goals. Be thoughtful of logistics and how employees will get to and from the event while prioritizing their accommodation and safety. 

Final Thoughts

 Facilitating a leadership retreat requires a lot of planning, and although it means that some aspects will make it harder than usual, it’s important to keep in mind what the outcome of the retreat will be. If there is a goal, and employees align themselves accordingly, leadership retreats can be successful, functional, and fun at the same time. 

Sabine Ghali

Kelly Murphy


Certified Meeting planner with 20+ years of event management experience, founder of ConferenceSource, expert in meeting facility sourcing & contracting in North America, Europe, South America and Asia. Kelly will manage your budget as if they were her own, negotiating the best possible rate and hotel contract to benefit and protect every client and exceed all expectations for all planning aspects for sales meetings, educational meetings, product launches, incentive trips down to a small board of directors meeting. We make meetings easy understanding your meeting objectives and delivering meeting matched components.