On Purpose Leadership & Strategic Planning

strategic planning retreat manual

The CEO’s Guide to Strategic Planning Retreats That Get Results: PART 2

This post is the second in a three-part series on how to hold a successful strategic planning retreat. it outlines how to get the most value from your time during your annual retreat., the other posts in this series discuss the key steps you must take before your strategic planning retreat and how to follow up to ensure your organization’s ongoing success., part ii: 6 ways to maximize your time during a strategic planning retreat..

You’ve likely attended an unproductive strategic planning retreat in the past. You had to leave the office – and maybe even your home – for a few days and travel to a remote destination that promised to make magic happen within your team. But when you got there your team talked about all the same things as last year and didn’t really accomplish anything, and your organization didn’t change for the better.

We feel your pain and, it doesn’t have to be this way.

Your strategic planning retreat should be an inspiring event where your team members work together to achieve great things for your organization. This requires a mix of creativity, collaboration and fun.

Here are six things a leader should do during a strategic planning retreat to inspire your team and align them around a shared vision:

Many leaders are competitive and high in dominance. While these qualities are what makes them powerful leaders, they can also get in the way when building a team game plan.

A leader’s strength of personality can overpower their team during meetings – often without their even knowing it. Controlling the conversation will cause your team to shut down. If you want to craft a strong strategic plan, you need to share the reigns with your team.

The most powerful strategic plans are the ones that teams create in real-time. The more your team members contribute to the plan, the more they will gain a sense of ownership. Then, they will be inspired to take action and help your organization achieve long-term success.

2. Define your “WHY”, “WHAT”, and “HOW”.

To build an on-purpose strategic plan, you must address the following topics:

  • WHY you exist. Develop or reaffirm your core philosophy. What is your mission? What are your core values?
  • WHAT your goals are for next few years. What will have the biggest impact on your growth, customers and employees?
  • HOW you will execute your strategic plan. What are your strategies, tactics, and timelines? Who will be responsible for conducting the work required and by when?

3. Move from the macro to the micro and finally, back to purpose.

Your organization likely has “big picture” people who love to talk about philosophy. You also probably have more “operationally focused” people who are driven by completing tasks and paying attention to details. Many team members won’t want to contribute to the big picture until they have a chance to address, share, or sometimes vent about their challenges. Once they are satisfied that their issues are going to be addressed, only then can they focus on strategy and purpose.

Start the retreat by discussing the macro – what’s going on externally, and give some thought to organizational purpose. Then, evolve the conversation to your organizational goals and the issues you face. We employ a technique where everyone confidentially addresses challenges by writing what’s preventing their success on a cue card that we resolve together. From there, everyone can move back up to refine their actions and goals, as well as confirm the organization’s purpose.

4. Give all of your team members floor time.

Every organization has people who love to take center stage and people who prefer to work quietly behind-the-scenes.

It’s important to give everyone a chance to participate. Ensure you hear from the introverts and analytical types who tend to keep their insights to themselves. This means you need to control the extroverts who are dominating the conversation and incorporate a process that encourages and allows the quieter types to engage.

Your team should also feel like they are in a safe space where they can be honest about their opinions. Moderate the conversation to make sure that no one is embarrassed or ridiculed when they share their thinking.

5. Be an example.

The leader must serve as an example for the team. This means sharing your passions and commitment, as well as demonstrating some vulnerability. Leaders must typify the culture and values of the organization they lead. While business is a game of efficiency, productivity, and results it is also a game that needs heart, passion, and caring. Leaders who live by all of these traits are the ones who inspire followers and lead their venture to greatness.

At a memorable strategic planning retreat, a new leader shared a lot about his background, fears, and challenges. His honesty helped the team relate to him. He led by setting the example and the entire team – which was previously competitive, combative, and at odds with one another – became more honest and collaborative. It also helped the team be more willing to get on board with a common vision.

6. Have fun.

Fun? At a strategic planning retreat? You bet!

Strategic planning is stressful. Big decisions affecting lives and careers take place at these events. However, it’s important to break up your work sessions with some fun. Explore the sites. Take part in outdoor activities. Conduct some activities that you wouldn’t normally do at work. Have a few beverages together. These activities can build morale and help your team get to know each other.

Creating an on-purpose strategic plan is a team process . When your team works together, it crafts a powerful plan that will help your organization grow, drive revenue and blast past your competitors.

Stay tuned for the final blog post in this series, where you will discover how to follow up after the retreat to ensure success. Also, be sure to check out the first post, which offered tips on what to do before your strategic planning retreat.

Related posts:.

  • 5 Keys to Building a Strategic Plan That Fuels Growth
  • The CEO’s Guide to Strategic Planning Retreats That Get Results: PART 1
  • The CEO’s Guide to Strategic Planning Retreats That Get Results: PART 3
  • The #1 Mistake That’s Ruining Your Strategic Plan

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strategic planning retreat manual

strategic planning retreat manual

D-I-Y: Tips for Designing a Strategic Planning Retreat for Your Education Leadership Team

strategic planning retreat manual

By  Michael Gisondi ( @MikeGisondi ) 

In the past six months, I facilitated two retreats for education leadership teams within the Department of Emergency Medicine at Stanford University School of Medicine. Each of these retreats had different audiences of faculty and administrative staff, with distinctly different goals and objectives. However, both retreats shared a central theme: Strategic Planning .

Strategic planning retreats are designed to promote positive team dynamics, while also meeting a specific set of desired administrative outcomes. Successful retreats foster the critical changes necessary for an improved future for an organization or team. To achieve such outcomes, retreats must be thoughtfully planned and executed.

The first step is the most important: defining the purpose for your retreat. The agenda can be crafted once you have a clear objective in mind. Some common reasons for hosting a strategic planning retreat include:

  • Bringing together a new leadership team
  • Defining or renewing vision and mission statements
  • Development of a new organizational chart
  • Short- or long-term goal setting
  • Creating educational dashboards
  • Teaching new skills to your team
  • Updating a communications platform or other technology
  • Financial planning
  • Curriculum redesign
  • Reviewing metrics at the sunset of a longitudinal project

It is important to create retreat agendas that address a single goal. Avoid the temptation of including too much material for a single day, including numerous retreat objectives, or mixing training and planning retreats. Decide which domains are most important and stay focused. Adults have limited attention spans and can hold focus on high-intensity, team-based work for only so long. You will see better results with shorter, targeted agendas.

Here are some additional tips for designing strategic planning retreats for your education leadership team:

…Before the Retreat…

  • Identify clear goals and streamline the agenda.
  • Secure an off-site location that is comfortable and convenient. Consider parking!
  • Plan many months in advance to allow all team members to adjust their calendars.
  • Set a start time that is no earlier than 9:00am. You want your team members well-rested.
  • Arrange for catering: breakfast, lunch, snacks, and lots of caffeinated beverages.
  • Purchase supplies: Post-it Notes , white board markers, note pads, pens, flip charts, etc.
  • Purchase toys. Yes, toys! Adults get bored easily in meetings. Distribute Fidget Cubes , Lego blocks, stress balls , Play-Doh , and other analog distractions.
  • Confirm WIFI, LCD projector availability, appropriate dongles, and adequate power outlets or power strips for laptops.
  • Arrange for a door prize – a book giveaway, for instance – as a raffle to start the retreat. Purchase a book with a professional development or leadership theme that might make for a good book club in the future.
  • Assign homework. I create a Word doc with ’20 Questions’ to be completed before the retreat — this prepares each of the team members for the topics I plan to discuss. Click here to see the pre-retreat homework from our program directors’ retreat last fall.

…The Ice-Breaker…

  • Ice-Breakers are a necessary evil. While these activities may appear to waste some of the agenda time, Ice-Breakers are useful for getting the team talking and energized.
  • Choose Ice-Breakers that mix fun and professional development.
  • www.pottermore.com : Get to know your team using this Harry Potter fan site. Have your team login for free and complete The Sorting Hat to determine their house. Harry Potter superfans can also Discover Your Petronus . Have team members guess the house assignments before they are revealed. (Idea Credit: Laura Hopson, University of Michigan)
  • Rose, Bud, Thorn. Adapted from the book, Mastermind Dinners by Jayson Gaignard, ask your team members to identify recent projects that were successful (a chance to brag about accomplishments: Roses), projects that have potential and may need some team input (a chance to ask fellow team members for advice: Buds), and projects that are stuck and need a brainstorm (hurdles that team members are facing: Thorns).
  • Ground Rules. Ask each team member to offer one rule that will guide the discussion for the day. For example, “Allow each team member to complete their comments without interruption.” Write these on white paper that is taped to the wall for the duration of the retreat. My three rules: “(1) We matter – advocate for one another, here and elsewhere. (2) Don’t get stuck in the weeds today. (3) I want to hear about your moonshot ideas .”

…Getting through the agenda…

  • Respect your team by staying on time throughout the day.
  • Agree on the frequency of breaks. Will it be a working lunch?
  • Change agenda items hourly. This will facilitate a progression of work and will place a time limit on unproductive or contentious discussions.
  • Facilitate, don’t lecture. Your job is to introduce material using engaging narratives, video, data, or testimonials. Once a goal or problem is clearly stated, it is up to your team to meet the objective for the hour. (For example, I used this Ted Talk by Simon Sinek to introduce a discussion of residency branding. Idea Credit: Alexei Wagner, Stanford.)
  • Call on team members who are natural introverts. Solicit their opinions and ideas. Consider having your team read, Quiet: The Power of Introverts in a World That Can’t Stop Talking , if you have had trouble balancing discussions among your team members.
  • Create a ‘parking lot’ wall for off-topic comments and ideas. Write each idea on a Post-it note and place on the parking lot wall for review at a later time.
  • Create a narrative for the day. Topic A should set-up the discussion of Topic B, and so on. I like splitting the day into three parts, using a set of retreat questions attributed to the Jesuits: Who am I? What am I doing? What am I trying to become by my actions? For our recent residency director retreat, the corresponding agenda was as follows:



  • Assign tasks for follow-up to various team members throughout the day.
  • Ensure that assignments are actionable and agree upon a timeline for deliverables.
  • Take photos of all white board notes, Post-it notes on the parking lot wall, etc.
  • Collect any brainstorming materials, in-service quizzes, or other paperwork.
  • Identify dates for future on-site meetings.
  • Acknowledge plans for future retreats and solicit ideas for agenda items.
  • Seek feedback on the format, agenda, location, and other elements of success.
  • De-brief with directors and managers.

Finally: HAVE FUN! Your colleagues share your passion for education leadership and want the best for your training program. A successful off-site retreat requires investments of time, resources, and talent – don’t waste this wonderful opportunity to build a new future with your colleagues.


My personal thanks to the administrative staff members who made the above-described retreats come to life: Maria Alfonso, Yasmin Deosaran, Jhu Jhu Lomboy, and Bianca Velasquez.’

Featured image via  by LadyofHats [CC BY-SA 3.0] via Wikimedia

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Actionable best practices for a strategic planning retreat

strategic planning retreat manual

Companies thrive when they’re guided by clear, mutually agreed-upon strategies. But it can sometimes be difficult to fit high-level strategic planning around day-to-day activities.

Strategic planning retreats bring company leaders and employees together for a few days to discuss core company themes, identify opportunities, and develop a clear roadmap for the future. They allow everyone to take a step back and think about the bigger picture.

In this article, Basejam will share some of the best practices in planning a strategic retreat that will ensure your event is a success.

What is a Strategic Planning Retreat?

strategic planning retreat manual

A strategic planning retreat is an off-site event that gives an organisation’s decision-makers a chance to build new strategies and concoct plans for the future. It's meant to bring together key members of the organisation and have comprehensive discussions on how to drive company growth and success.

In addition to this main goal, strategic planning retreats also aim to strengthen team dynamics while meeting a set of desired outcomes. This way, you’ll have a cohesive team equipped with the right tactics that can benefit the organisation long-term.

How Can Actionable Strategic Planning Retreat Benefit Your Team?

Opportunity to assess team value contribution to the business.

During a strategic planning retreat, team members can take a break from their daily grind and redirect their focus toward the overall performance and direction of the team or company. They can evaluate how well they’re functioning as a unit, determine which areas they’re excelling, and identify areas for improvement.

It’s also a great opportunity to make sure everyone is aligned toward accomplishing individual and administrative goals.

Fostering team cohesion

Strategic retreats are like family reunions.

They allow your team to get together in a relaxed and open environment to reconnect and ground themselves. It’s a chance for team members to loosen up and get to know each other better. Spending time together in a team offsite and engaging in team-building activities during the retreat strengthens your bond, allowing you to trust each other more and communicate openly.

Teams and organisations who have harmonious relationships perform better and are more likely to succeed.

Develop leadership skills

Strategic retreats do not only focus on improving team cohesion; it’s also designed to help team members become people leaders .

Through various activities and training, individuals can improve their decision-making capabilities and develop their leadership skills. This helps create a competent team that can handle their responsibilities well.

Things To Consider When Planning Strategic Planning Retreat

Date: It should be set on a mutually agreeable date when everyone could attend, including key stakeholders, managers, and directors

Objective(s): Aside from fostering team cohesion and developing leadership skills, objectives should also include organisational matters, such as developing a new strategic plan and reviewing current company performance

Duration: Give your team enough time to achieve your objectives, plus extra time for team bonding and activities

Budget: Take into account cost per attendee, venue, transportation, food and beverages, and activity-related expenses

Responsibility: Assign specific individuals with tasks, such as organising bookings, finding venues, preparing presentation materials, etc.

Attendees: Determine who should be included in the retreat;

Facilitator: Assign a facilitator to ensure that the agenda is met and that all attendees can participate

Meeting facilities: Think about what facilities are needed as well as the size of the room (there should be enough space to accommodate all attendees and activities)


Recreational activities

Data: Decide on what information is required from managers and directors for the group discussions and presentations

Actionable Strategic Planning Retreat Best Practices

Pick a location that aligns with your goals.

To concentrate and keep distractions at bay, leaving the office is essential. But not any venue will do—it needs to align with your goals for the retreat.

Start with baseline requirements like your headcount and required facilities. These are great ways to narrow down your search by eliminating venues that don’t fit the bill. Then add in those important ‘nice-to-haves’ like:

Climate (i.e., hot, warm, or cold)

Nature (i.e., beach, forest, lake, etc.)

Available recreational activities

Catering options

With Basejam, you have access to a curated list of retreat-ready venues along with information about each one. You can filter your search results based on your location, accommodation style, amenities, number of people, and even reason for retreat. This way, you’ll surely discover a venue that is perfect for your specific needs.

strategic planning retreat manual

Establish specific deliverables

What do you want to achieve by the end of your strategic planning retreat? Be specific—a clear deliverable (or multiple) will give your team direction and purpose.

Be extremely clear about the goals you have for the occasion. Consider the ideal result and the criteria you will use to evaluate its success. When you have a clear objective in mind, work backwards to create a strategy that will get you there.

Identify who should participate

After defining the objectives and scope for your strategic planning, it's time to identify who should attend the meeting and their roles throughout the event.

Include those who will lead and implement the strategy. Their active engagement before, during, and after the meeting increases the likelihood of a successful retreat. Employee participation is essential at every stage of the planning process, but strategic planning retreats often involve leadership and key decision-makers.

Set an agenda

strategic planning retreat manual

Make an agenda that addresses all the critical problems identified in your pre-retreat evaluation. Make sure the agenda is open to unexpected debates or new topics. Consider holding break-out seminars to address departmental challenges.

The schedule should also include adequate time to discuss the tasks that emerged from the retreat. Set aside time to create a follow-up strategy to guarantee that the plans discussed during the retreat are effectively implemented.

Design a structured process

It’s time to develop a structured process for the retreat once you have a clear grasp of the objectives, scope, and participants. Plan with specific goals in mind, and decide who will lead each discussion.

While you may be eager to see results, keep in mind that the quality of the dialogue is critical. Aim for genuine participation from all those involved. Create a safe environment in which team members feel comfortable sharing their ideas without fear of repercussions from workplace politics. Also, make sure that no individual dominates the discourse.

Move from the macro to the micro (and then back to the purpose)

Begin your retreat by talking about the broad picture—external forces and your organisation's mission. After that, address your objectives and challenges.

Use cue cards to have a private talk about the challenges. Solve these problems together.

Review goals and actions to ensure they are in line with the mission of your organisation. This method results in a productive and aligned retreat.

Use data-driven insights

When making strategic planning decisions, rely on facts and relevant insights.

To ensure a strong SWOT analysis, conduct interviews and surveys wherever possible. This analysis will give the necessary context for strategic decisions.

strategic planning retreat manual

Create and use pre-work templates after gathering enough feedback to ensure that all meeting participants begin with an idea of the present situation, difficulties, implications, and objectives. This baseline allows everyone to get started on the same page.

Encourage diverse perspectives

In both small and big group conversations, encourage everyone to speak up. When the loudest voice dominates the discourse, valuable viewpoints might be lost, resulting in bruised feelings and dissatisfaction.

Allowing everyone to contribute allows you to realise your team's full potential. It results in a strategy plan that is not only visually appealing but also effective in attaining your objectives.

Prioritise actionable items

Make a targeted strategy plan by identifying essential initiatives and ranking them in terms of impact and feasibility. Keep objectives manageable to avoid being overwhelmed. To turn goals into actionable tasks, create a detailed action plan with specific phases, responsibilities, and dates.

Document everything

Keep complete notes of all retreat conversations, decisions, and action plans. These records will be useful references in the future. By documenting everything, you can quickly track progress, revisit ideas, and verify that the retreat's conclusions are applied properly over time.

Ready to plan your strategic planning retreat?

Don't pass up the advantages of a strategic planning retreat. Form a cohesive team, hone your leadership abilities, and set actionable goals. By taking a break from your daily work routine and dedicating time to a strategic planning retreat, you can form stronger collaborations, well-defined strategies, and a clear roadmap to your business’ success.

Explore a curated list of inspiring company retreat venues with Basejam and start planning your transformational retreat now!

strategic planning retreat manual

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How to Lead a Strategic Planning Retreat

How to Lead a Strategic Planning Retreat

There is no substitute for getting your team (and your whole organization) working toward the same goals. A strategic planning retreat can pull everyone’s heads out of the office, so you can look at the bigger picture together.

We have learned some important lessons that make the difference between success and failure in strategic planning efforts. If you’ve already decided that you want to lead your own retreat (instead of bringing in an expert facilitator), you can increase your odds of success by paying attention to these keys.

#1: Measure your Mountain

When I lived in Africa, a massive and beautiful plateau rose 3,500 feet above us just a few miles from our home. Since I was in fairly good shape from running and riding my bike, I didn’t really need any preparation to hike up to the top. But when a friend challenged me to climb Mt. Kilimanjaro with him (19,341 feet!), I knew it would take a lot of work to get ready.

Before your strategic planning retreat, you need to measure your mountain to understand what you are trying to accomplish. Do you want to come out with a full 3-5 year Strategic Plan? A more limited Annual Plan? Or just a review and refresh of a plan you already have? Once you decide, make sure to set expectations by letting your team know exactly what you want to get done on the retreat.

Keep in mind: the bigger your mountain, the more work you need to do in advance.

#2: Assemble the right questions

A common pitfall in strategic planning is not digging deep enough to uncover the real issues. If you ask superficial questions, you will end up producing a plan that looks remarkably like what you are already doing but with bigger numbers. If you want to get past that, you’ve got to ask the right questions.

The right questions are not only difficult to answer, they can be difficult to think of. Here are a few to get you started:

#3: Share responsibility for preparation with your team

Sharing responsibility is not just good leadership, it’s also smart. Let people choose areas of ownership (or make assignments). They will accomplish more preparation than you could alone, and they will be more invested in the process. That’s two big wins for you.

What areas does your team need to prepare in advance?

  • Logistics. This includes arranging the venue, meals and snacks, materials on site (projector, easel charts or whiteboards, and markers), calendar invitations, and reminders.
  • Research . Someone needs to collect relevant information like recent financial reports, any available market information, and the last set of written plans or goals that you have.
  • Employee survey results. Don’t take the risk of having your wonderful new plan blown off by your employees because you didn’t consult them. A simple survey can give you a feel for what employees are seeing and raise issues for discussion at the strategic planning retreat.
  • Agenda and schedule. You need an agenda to follow that will guide your discussion at the retreat. A schedule and a dedicated timekeeper help you stay on task and make progress. If your team knows what is on the agenda, they can prepare to discuss items in their own areas.

#4: Stay in your role

Since you have chosen to facilitate the retreat, your team needs you to stay in that role. Here is what happens when you don’t have good facilitation:

  • The group gets sidetracked and chases rabbits
  • Discussions go long and do not conclude with specific actions or decisions
  • Quiet people watch and don’t give their input
  • Loud people talk too much and dominate

Committing to the facilitator role is difficult for most CEOs or owners/presidents. You can facilitate, or you can participate, but you can’t do both at the same time. The facilitator doesn’t answer questions—he or she asks them and follows up with more questions to get the team to really think.

Once you start championing an idea, you have become a participant, and it’s hard (or impossible) to facilitate discussion of the alternatives. If you switch roles mid-retreat, your team may get confused or disengage.

“You can facilitate, or you can participate, but you can’t do both.”

A strategic planning retreat could be just what your team needs to create alignment and break through obstacles.

Have questions?     Reach out and talk to us about how you can plan and lead a successful strategic planning retreat for your team.

Like us on Twitter , LinkedIn , or Facebook to get thoughtful articles on the bridges leaders must build and cross to inspire greater performance.

Written by Phillip Shero

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