The 3-day offsite corporate retreat format is most commonly used as a once per year gathering between top executives to engage in a full strategic planning session for the organization. Typically, early fall is a great time to hold such an event for a variety of reasons. Vacations have ended, the fourth quarter has started, there is ample time to prepare resources for the coming year, and the weather is typically nice almost everywhere in early October.


It would be almost impossible to plan a purposeful corporate retreat without spending several hours with the leader of the strategic planning session. These meetings can be held over the phone, and some correspondence can be exchanged via email, but I strongly suggest at least one in-depth, face-to-face meeting with the organizer. During these meetings, the facilitator should assess the leader’s purpose and intentions and discuss with the leader how power can be used and misused during a strategy session. I do not know of any leaders in today’s business environment who want to dominate a meeting. They all want to elicit opinions and engage the minds of their top people; yet, sadly, their presence can derail any synergistic value.

This can happen very subtly. Here is an example: Let’s say we were doing a brainstorming session on colors for our logo. Different people around the room might say things like, “dark green,” someone else spits out “orange,” another person says “red is powerful,” still another says “I like black and gray tones,” and the CEO, wanting to be part of the conversation, says “blue.” What typically happens next is that everybody in the room starts thinking of shades of blue, and turquoise, sky blue, royal blue, and navy are the words that come out of the mouths of those who had already proposed alternate suggestions. It is human nature to defer to power.

Communication and a trusting relationship between the leader and the facilitator allow power to be diverted away from the leader so the leader is a participant rather than the leader of the retreat. That job should be left to the facilitator. They have been trained to bring the group back into dialogue, which can create the synergy necessary for a successful retreat. A power struggle between the leader and the facilitator will kill your retreat. It is best to deal with this in advance and have an arrangement between the two so the leader’s objectives can be achieved.


  • WEEK 1

    I ask them to get with their team to do a review of the year, including accomplishments and failures based on the projects they were assigned from the previous year. It is important to get a ground-level view from staff members’ perspectives, which may help inform the leader in new ways.

  • WEEK 2

    I ask participants to get with their team again and brainstorm projects the team would like to have introduced at the coming year’s strategic planning session. Again, the thoughts from the staff may be different than those of the leader, but more importantly, it provides an opportunity for the participants to feel as though they are part of the strategic planning process. After all, they may be asked to put the plan into action in the coming year and will be much more interested if they knew they had a voice in determining the direction.

  • WEEK 3

    I ask each participant to do a deep dive into a SWOT analysis (Strengths, Weaknesses, Opportunities, and Threats). This is a written assignment they are to return to the facilitator. I provide the form and instructions on how to fill out the form, and most importantly, I provide a commitment that all answers will remain anonymous; this means the facilitator will not divest who wrote what. Participants may claim their own answers during the meeting, and they usually do, but if they want to present their ideas without any risk, this provides the opportunity to do so.

  • WEEK 4

    This is my favorite exercise. A few days before the retreat, I send a questionnaire out to each participant with four simple, but potentially difficult, questions. I ask that they envision themselves driving or flying home from the retreat and reflecting on what they just experienced, and then answer these questions:

    • What did you like most about the retreat?
    • What surprised you most during the retreat?
    • What do you wish we would have addressed that we did not address during the retreat?
    • What do you wish we would start doing or stop doing on future retreats?



    It is vital to get any meeting started off right. There are four very important considerations in this process. These include:

    1. The leader needs to establish the purpose of the meeting.
    2. The leader needs to make a statement that the company is committed to providing the resources necessary to accomplish the goals.
    3. The group needs to know when to expect breaks, meals, end times, and other logistics.
    4. The group must establish the ground rules by which to abide while together. While the facilitator can lead this discussion on ground rules, it is important that the participants create them. If they create them, then they will follow them, or in the worst case scenario, they will listen to the facilitator when they ask to have them enforced.

    Now we are ready for the leader to give their “state of the company” address. It is a good idea for the leader, and maybe the board of directors, to clearly articulate how they see the organization’s fit within the industry, including how the organization is doing financially or other metrics that are important to the long-term vision of the company. This does not need to be a lengthy speech—simply an acknowledgement of the current truths the organization faces. The organization’s executives and staff members may have their own opinions on the state of the company, but a facilitator can help bring these perspectives into alignment if, in fact, the leader is bold enough to clearly present their perspective on the state of the company.


    To get a little break from the intensity of the opening session, I like to add in an extremely important section, which is a review of the vision, mission, and core values of the organization. Rarely do I make adjustments to any of the company’s values, but we can certainly challenge whether the organization’s mission is aligned with the vision. This sometimes leads to interesting dialogue, especially if the organization is not living up to its cultural standards, but often times, the group validates that “this (the mission and vision) is who we are” and tell stories on the “ways we walk the walk.” I like to ask for these stories and have the participants share examples where they have seen people in the organization living the company’s values. This is a great way to bridge gaps between departments and humanize the organization. It generally gets the group off on the right foot.


    We continue the “state of the company” discussion by looking at a compilation of the individual SWOT analyses. I go through each one and write every item out under its category. If an item is mentioned by more than one person, it gets an asterisk for every other person who has said the same thing. Whenever possible, I attempt to use the exact language the person used and not paraphrase. In compiling the answers, I start with one category at a time and go through each participants’ sheets. Then, when I get to another category, I work backwards so one person’s answers are not always at the top, which helps to ensure anonymity.

    The SWOT analysis is one of the most useful tools for opening the minds of the participants to look at their own reality. It is interesting to note the perspectives from which each participant comes to their conclusions: The results from finance are completely different from those who are in sales, and surprisingly, the marketing people see the world differently than the salespeople do as well. When the group can discuss these perspectives in an open and honest way, we can get a 360-degree view of the state of the company, which helps to inform our goals for the coming year.


    A full strategic planning session would include a look back at what has been accomplished since the last strategy session. This includes initiatives that were fully executed, some that may be still in the works, and those that have been scrapped or put in a parking lot. It is important to discuss them all. Remember the pre-retreat assignment? It is great to have the perspectives of the staff members who are working on these initiatives, as well as the leader’s perspective to assist in our analysis. On the initiatives that have been accomplished, not only can we learn what happened and how it happened, but also, we can quickly analyze the benefits the organization has received since the implementation. Giving the attendees the feeling that what we are doing here is not only possible but important is a great way to start off a retreat.

    For those initiatives that had not yet been completed or had to be scrapped altogether, we can view the reasons why this happened. Doing so may help us to determine whether we should allocate additional resources (time, money, or people), develop management processes, or recognize that the initiative was not all that vital, to begin with. We can, and should, learn from our failures. This portion is not intended to be a finger-pointing session, rather, it is an acknowledgment that we (the company) were unrealistic in regard to the potential of the initiative, what obstacles were presented, and how these obstacles impeded the success of the initiative. Applying this evaluation to a failed initiative will be beneficial as we begin planning for the coming year.

    Well, we made it to lunch on the first day. Take a minute and look back at what we have accomplished in the first several hours, and then take a break! This is intense work— sometimes frustrating, sometimes exhilarating, and almost always emotional. Breaks are needed. They give everybody a chance to take a deep breath, attend to personal needs, and reset for the work ahead. Set a time to reconvene, as this is a good time to recommit to one of the ground rules the group probably set, which is to be present and on time.


    The afternoon session on the first day is designed to set up the field of play. We like to start with a look back at the threats on the SWOT analysis and identify the existing barriers that could keep us from realizing the vision. While barriers can contribute to a negative atmosphere to start, it is important for the group to be realistic and recognize the difficulties that may lie ahead. A properly facilitated session, however, provides an opportunity for the conversation that occurs as a result of the SWOT analysis to be reframed, and then the group can begin to look for detours when they see roadblocks.


    We are finally at a stage where the group can focus on moving forward. We have spent most of the first day looking in the rearview mirror, taking a look at where we started and reestablishing the team’s commitment to obtaining the vision by delivering on our mission and living our core values. All of that is necessary to understand our position and begin to gain alignment on the goals for the coming year.

    A typical company will look at their world through three Ps: people, process, and product. Therefore, it would be wise to create a list of initiatives that revolve around each of these principles. The pre-work the executives have done with their teams may very well have generated a list of ideas that the executives can bring into this session. The facilitator or scribe will stand next to the flip charts to capture every concept or idea the team lead brings forth. These ideas are those that were generated in the second pre-work assignment. Space must be given here for other executives to ask clarifying questions and add to the list of suggestions.

    Now we have at least three flip chart pages, each with a list of items we need to begin to rank and give weight to. There are several ways we can accomplish this. One of my favorites is make a game out of it. I use stickers—you know, the kind kids like to play with. On my last retreat, we used “happy face” stickers with a different color assigned to each of the executives in the room. It is vital to set up the rules of the game prior to beginning the exercise. The rules are simple: Each executive is given three stickers per category, and they are to place one sticker next to the highest priority item on each category. When everybody has rated each of the categories, we count the stickers and create a new list of the top 2 to 4 initiatives per category and then create a new flip chart page with all of the “winners” on one page.

    We then ask each person to take some time on their own to rank these items (there will typically be somewhere between eight and 10 items they should rank from the highest to lowest priority). Next, we go around the room and ask each person to share their ranking of these items and create a chart of their answers on the flip chart. When everybody has their rankings noted, we simply do some math. The next step is to rewrite the items in ranked order, with the lowest score as the highest priority.

    Rewriting the list on a clean sheet of flip chart paper is vital here, as it clears the space and allows the team to really see in black and white the rankings they gave to the most important items for the coming year. Ask them to take some additional time and reflect and then bring them back into dialogue to debate or confirm the list and the order of the items. What we are looking for here is a consensus on the priorities for the coming year. Do not rush this piece—allow everybody to be heard and allow for some adjustments if the group can come together and create alignment on the priorities.


    From here we ask the CEO, or highest-ranking member of the team, to give a brief analysis of the resources the organization is willing to allocate to the goals this group will be setting. It may seem premature to discuss resources prior to establishing goals, but what we have found is that this type of debriefing will provide the group with comfort that they are not wasting their time, and that what we are about to embark on has real teeth. The knowledge that the company is behind the executive team generally provides the support needed for the upcoming brainstorming session.

    Brainstorming is a process that can be accomplished in several ways. The primary goal is to enlist ideas, some that everybody may be thinking about, but many that are outside of the box or even outlandish. What we are trying to accomplish is to eventually get down to the four or five strategic initiatives the company will focus on in the coming year. What we do not want to do is stifle imagination or creativity in the process. Brainstorming provides an opportunity to hear what others have been thinking but not saying. If this is done right, even the introverts practically jump out of their seat to participate.

    Our process is one in which we want to participant to go wide with their ideas and concepts and then eventually converge on what is relevant, important, and possible. This is also the point where the CEO/leader can open their mind and see possibilities that they did not know existed; often, they come back and make a statement that may enhance or reopen the resource allocation discussion.


    One caution on a multiday event is to be aware that there are typically several folks in the room who wished we would have dug in and “gotten something done.” What you will notice is that some people in the group are a little anxious, as they now have a list of priorities and could be frustrated that it took so long to get to this point. It is important to summarize all that did get done during Day 1.

    This team has identified and consolidated its strengths, weaknesses, opportunities, and threats. The team recommitted (or reworked) the organization’s culture (values, mission, and vision). We had reports from each working group on the success from the previous years and a global look back from the company’s point of view. We also identified the priorities we will dive into on the next day. Finally, we heard from the leader the resources that may be available and a commitment from the company to support the efforts this team will develop.

    This summary gives a lot of weight to the work that was done and provides a framework for the rest of the summit. Another good idea here in the summary is to refer to the ground rules, especially if punctuality is on that list. Reminding everybody of the start time for the next morning will allow us to recommit to each other this particular ground rule. Now it is time for a break before dinner. Give the team some time to unwind, reflect, and refresh. I suggest 45 minutes to an hour before regrouping for the evening’s activities. Giving any more time than that may lead to some folks falling asleep and missing dinner. They may not realize it, but they will be tired. This is exhausting work. I do not suggest planning a long event, as you really do not want people burning the candle too late, but a nice dinner together is a great way for the team to relax and bond.


Whether you decide to host breakfast, provide a simple continental breakfast, or simply have everybody prepare for the day on their own is up to the company’s designated retreat coordinator. Whatever you decide, just be clear in advance, so that everybody understands the expectations and how they should prepare for the day.

    That famous line credited to Stephen Covey is a great way to start Day 2. A key to setting the stage for where you are going is to preview exactly that: Let the group know where you are going. The goals by the end of the second day in our strategic planning scenario are to allow the group to know what to expect. One way to get to this place is to review the accomplishments of the previous day and then allow for open discussion on any items on that list. Often times, after a good night’s sleep, issues surface for the participants, and it is a good thing to allow them the space to let others know what they have been thinking or feeling. This often leads to a dialogue that will either reframe or reconfirm the path we are on.

    I am a big believer in a strategy described in the book Humble Inquiry, written by Edgar Schein. The premise of this work is actually the subtitle of the book, The Gentle Art of Asking Rather Than Telling. What this means is that, rather than tell the team exactly where we are going, ask them what their goals for the day are. Yes, this sometimes takes gentle prodding by the facilitator, but what we typically find is that the participants will create self-alignment on the outcomes. The value here is that they have decided on the outcomes, not the CEO, and certainly not the facilitator. It is powerful when the participants set the expectations: They buy into the process and actually own the outcomes.


    Now that the team has set the desired outcomes for the day, providing them a framework on how to accomplish their tasks is the next step. I prefer to break the larger group into smaller subsets—either two or three small groups depending on the number of participants. If we have eight or fewer participants, we will create two small groups, and if we have more than eight, we will break up into three or possibly four small groups.

    Let them know that each group will take the issues they are assigned and complete the following steps:

    • Develop the description of what the issue really means
    • State with clarity the “why” behind the issue
    • List a series of goals that would ensure success if we accomplished them
    • Begin to develop strategies underneath each of the goals that would lead to the goal being met
    • Suggest a potential champion for the initiative

    In addition, let them know that shortly after the afternoon break, each group will make a presentation to the other group on their findings. It is a good idea for a different person to be assigned to present each initiative. The rest of the small group can add supporting ideas during the presentation to assist but having different presenters for each initiative gets more involvement from everybody.


    One way to break the groups up would be to determine team captains and hold a draft. Like the NFL, or even your childhood playground, identify captains and have each captain pick their team. Certainly, there are other methods, such as random placement, but I believe the key here is to encourage diversity on the teams prior to the draft. For instance, in a perfect world, I would want to separate people from the same department or even similar departments. What is important is that we have cross-functional thought processes debating the issues, so the small team considers alternate points of view and sees the potential roadblocks.

    Next, divvy up the issues, ensuring each group has an equal number of issues to address. Let’s assume after the ranking exercise the night before that we have decided there are six initiatives that are the most important issues the organization faces in the coming year. Since we had eight participants, we ended up with two small groups, so both small groups had three initiatives they will be working on for the next several hours. This is now a good time for lunch, and early lunch works well because there is still a lot to accomplish, and the groups will need time to do this. During the lunch break, the facilitator or retreat coordinator can set up the room(s) for the small group work.


    Create separate spaces in the room and ensure each has a whiteboard and markers. If space permits, ensure there is some distance between the two groups. We have had times when separate rooms are available and others when maybe one group chooses to work outdoors; the key is to ensure there is space where people feel comfortable and that nobody is looking over their shoulders. While it is not necessary, providing the teams with an outline does provide some structure with which some might be more comfortable. Please do allow for creativity, however, and let them know this is only a guide, and that they are free to create their own structure.


    After the break, send each of the small groups off to do their work. Remind the groups that it is not their role to develop action plans or even timeframes for completion, as this will happen within the working groups developed by this team later. Their role is to prepare and present the five bullet points listed above: What, Why, Goals, Strategy, and Champion.

    The role of the facilitator is to float between the groups and answer questions on the process. If it becomes necessary, the second role of the facilitator would be to ask probing questions. This intervention should only happen if one of two scenarios presents itself: the groups seem to have stalled or there is a member of the group who looks as if they are dominating the conversation. The facilitator is NOT A CONSULTANT. They should not become part of the group, and they should not be answering questions as if they had the answers.

    By the end of the early afternoon session, each small group should have its own flipchart pages to make the presentation to the full team. They will have had an opportunity to determine who will lead the pitch and what they will say. With a sigh of relief, it is time for an afternoon break. During the break, the facilitator or retreat coordinator should arrange the room to allow space for the presentations to the entire team.


    Initiative by initiative, have the groups make their presentations to the entire team. Ensure they answer all of the pertinent questions on the what, why, and how this initiative will add value to the organization. Ensure you allow for questions and even challenges to be brought up during these presentations. This is vital if we are going for consensus and alignment. The utlization of a decision matrix can be quite helpful when preparing the presentaiton.

    While this is a serious assignment, it almost always becomes very fun for everybody in the room. Rarely have I witnessed these presentations without quite a bit of humor and laughter thrown in. This makes sense, because we are coming to the end of a very emotional process, and you can feel it in the room. People let their guard down, they are comfortable with everybody by now, and the entire team can see the realization of their vision.


    This team has made so much progress in a very short time. Ensure they recognize the accomplishments with a summary of both Day 1 and Day 2 at this point. It leads them down a path where they can feel a sense of pride in, and ownership of, their strategic planning process. Use the flipchart pages spread throughout the room to acknowledge just how much has been accomplished. Then, turn the meeting over to the administrator to give the details of the evening plans.

    In most cases, I would recommend physical activities for the end of the second day of the corporate retreat. It could be bowling or some other fun, physical activity. This provides an outlet for pent-up energy and an emotional release, such as laughter.


By now you will not be surprised to hear that I will be recommending another review of the progress we have made. This is also a time for open dialogue on what we have been through in the past few days. Allow for the discussion to go on as long as participants want to keep it flowing—to a point. Remember, we still have some work to do.

    We need to think through and evaluate the human resources that may be necessary to create the working teams that the champion of each initiative will need to finalize the plans and make them happen. One good way to do this is for each of the team members to throw names out and have the facilitator capture those on a flip chart. These could be people with a specific skill set, or they could be the young up-and-comers in the organization.

    The next step would be for the champion for each initiative to put in a request for their first-round draft pick. This would be the person who could step in and assist when the champion is not available, but it is probably a person with a passion for the initiative. Once we go through the first round, keep going and round out each initiative group with the talent available on the flip chart. Do not be afraid to ask for someone we did not identify earlier, as we can always ask ourselves who or what we are missing. Remember, we want to encourage diversity in thought and even in functional responsibility. A strong group would include individuals from multiple disciplines, ensuring we see the plan from a 360-degree view.


    Several things should be considered at this point, including how the individuals will be asked to participate in the group work, what the goals for the groups are, and the timeframes in which they will be reporting back to the executive committee.

    Remember back when we said creating action steps is not the responsibility of the strategic planning executive group? These initiative groups will be assigned this task, but only after they confirm or realign the goals and strategies to reach those goals. In addition, the newly formed group will be creating their own due dates for the assigned tasks, a champion for each task, and a list of additional resources they would need to accomplish the tasks.

    Now is a good time to set the first follow-up meeting for this executive team. During that meeting, the champion and team leader can come into the meeting and make a presentation on their plan of action that will lead to their initiatives success. My recommendation is that, within a month, the teams reconvene for this purpose.


    Your staff will be wondering what happened during the strategic planning meetings—after all, their jobs and livelihoods may depend on this plan, and even if they do not, your staff will wonder what impact this has on them. Create a plan within the executive team for what will be communicated to the entire company and how it will be communicated. It is important for us all to be on the same page here. The plan we create must be echoed from each of us.

    I recommend multiple methods of communication to the entire company. I believe a letter or memo from the CEO is a good start, but I also believe an all-staff meeting where a verbal presentation with visual aids is in your organization’s best interest. Remember what people hear and what they read may be different than the message you believe you are presenting.

    Having multiple methods of communication that are in alignment with each other will help to ensure the message you are trying to get out is the one people hear. Encourage the executives and then the directors, managers, and supervisors to talk to the staff, but only after you are sure they all are on the same page. Keep in mind, we have had three days to discuss these issues and come up with alignment, so do not expect line workers, or management, to completely understand the goals revealed through the retreat process through a memo or even one meeting. Do not skimp on the communication plan!


    This is the time the CEO/leader will bring the group back and reflect not only on the work we have all done but also to prepare us for the work that lies ahead. Styles differ, so the facilitator should not try to direct the leader’s comments. They know their people better than the facilitator, and they typically feel the need to wrap up the session and show appreciation for all of the hard and emotional work that has taken place.

    The facilitator can chime in and show appreciation as well, not only for the team but for the retreat coordinator who has provided the resources to allow for all of the work to be done. Give the floor back to the administrator to provide details on the events that will follow. Some choose to find a fun activity, while other groups are interested in getting home. I am not sure it matters what your group chooses if they are made aware far in advance of what the plans are.