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

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