A Magical Meeting Story from Jackie Colburn, strategist, facilitator, and founder of her own Design Sprint practice.

Welcome to Magical Meetings Stories, a series where I chat with professional facilitators, meeting practitioners, leaders, and CEOs across industries about their meeting culture. We dive deep into a specific magical meeting they’ve run, including their approach to facilitation design, and their tips and tricks for running meetings people thrive in. 

Today’s story is with Jackie Colburn, a design sprint facilitator and independent consultant out of Minneapolis, Minnesota. After six years of working in strategy and client leadership at GoKart Labs, Jackie founded her own Design Sprint practice in 2017. Jackie champions the design process in everything she does and is fond of activities that center storytelling as a vehicle for human emotion.

Jackie works with clients to design an environment that facilitates creativity, collaboration, and symbiotic relationships in the workplace. In her practice, Jackie loves to step in when teams are ready to make the change, but aren’t sure what the way forward looks like. Through optimism and openness, Jackie brings teams through the hurdle of miscommunication and damaged dynamics to realize their true potential.

I spoke with Jackie about her Teaming meeting, the reason behind it, and what she would do differently.

A Time for Teaming

Part of Jackie’s facilitation success comes from identifying the perfect time for a Teaming session, as was the case with her client, a sports company amidst transition. In this particular meeting, Jackie’s client experienced two major events: a newly appointed CEO and the recent acquisition of another company. Jackie put together a strategy designed to ease her client out of their current ambiguity and to identify a clearer path towards the future. 

In this time of change, Jackie discovered that the CEO and the founder were both open to creative problem-solving. Jackie shares that both the CEO and the founder “were aware that they had a problem and then they were willing to say, ‘We need help solving this problem.’”

Let’s take a closer look at Jackie’s process to learn what made this meeting magical.

The Meeting

While most of Jackie’s clients bring her in to facilitate a design sprint, this Teaming session was different. To unify the leadership team, Jackie used the following guidelines for her workshop:


Gather office supplies for organization and note-taking:

  • Trust the process
  • No tech
  • Empathy for one another 
  • Use “Yes, and” statements

In a Teaming meeting, the facilitator will choose the:


  • Basket for the “tech check”
  • Post-it notes in various sizes
  • Timer

Jackie recommends a team of seven people for a successful Teaming session. Jackie’s team included the founder, CRO, new CEO, head of marketing, head of product, founder of the newly acquired company, and CFO.

Plan the Workshop:

  • Length of time: 7 hours (10 am – 5 pm)


  • Issues List: keep, kill, combine
  • Storyboarding
  • Gain/Pain deep dives
  • Sailboat activity (AJ&Smart)
  • Action planning


  • Grounding
    • Icebreaker
    • Guidelines
    • Tech check
  • Opening
    • Introductions 
    • Issues list
  • Storytelling
    • Storyboarding
    • Gains/Pains
    • Issues list review
  • Strategic Plan Review
    • Intro from CEO
    • Team feedback: “I like, I wish, I wonder”
    • Issues list review
  • From Issue to Action
    • Sailboat (AJ&Smart)
    • Action Planning
  • Closing

Exercises: Grounding

In the grounding phase of a Teaming session, the facilitator reviews the day’s itinerary, identifies the intent of the session, and asks why each participant is there. 

As Jackie’s client experienced chaos amidst the changing leadership positions and the company integration, it was important for her to start the meeting with trust and empathy at the forefront. Jackie led the team with a check-in and asked participants to share the last emoji they used before requesting that everyone place their phone into the basket. Following the check-in, Jackie shared her “people-first” mentality to encourage each participant to see past their roles in the company.

Exercises: Opening

The opening phase of a Teaming session gives both the founders, CEO, and other participants the opportunity to introduce themselves and zero in on the day-long workshop.

During the opening of Jackie’s meeting, the CEO and Founder gave a brief company history and insights of what they observed within the company, as well as outcomes they hoped to reach during the session.

After the initial intro, the rest of the team introduced themselves and shared about their personal and professional bests from the last six months and what they were hoping to get out of the experience, as well as what was working, and what wasn’t. 

Exercises: Storytelling

In this phase of the meeting, the facilitator uses storytelling to encourage authenticity from the workshop participants. 

In her session, Jackie asked participants to storyboard “What’s happened for me over the past six months?”, as well as part of their story that offered the most gain and the most pain. 

During this exercise, each person noted something they did that made the moment a “gain” and what they did that made the moment challenging. Through the storyboarding process, team members also challenged each other by noting ways the other person might make a future challenge less painful.  

Through the storytelling exercises, Jackie kickstarted the cross-team discussion that is the heart of the Teaming process. 

“We had the storyboards up on the wall and looked at one another’s stories and spoke to one another across the team. It was good, it was one of those moments where I felt like, ‘Yay, it’s working.’”

Exercises: Strategic Plan Review

Following the lunch break, the CEO reviews the strategic plan, and the team offers feedback.

In this particular meeting, Jackie encouraged the team members to use “I like, I wish, I wonder” statements to share feedback on the strategic plan. The team then reviewed the issues list again to consider new issues and agree on the most important two.

Exercises: From Issue to Action

During this phase, the facilitator uses the sailboat activity to discuss the top two issues.

Jackie drew a boat as team members identified what pushed the boat forward or held it back in relation to each issue. The team then decided on “to-solves”, reframed them as “how might we” questions, and focused on idea generation. This was followed by an action planning step where each team member identified the top five actions they wanted to take as well as one action they wanted another member to take. 

When asked how she might improve the meeting, Jackie noted that she would have ended the meeting earlier. With such a packed agenda, Jackie shared that the action planning step might have been more productive as a separate meeting.

Exercises: Closing

The CEO and Founder shared their thank yous as the session ended. Team members shared their intentions and closings.

Exercises: Teaming with the Intention of Healing

While it isn’t always easy to identify the right solution to a problem, it’s painfully clear when something isn’t working. However, it is in this setting that Jackie thrives.

“I would say this is the type of session I would run during a moment of transition or if the team feels like their health is suffering. That’s why I liked the name Teaming or Gelling, it felt more like a group therapy workshop but with the intention of healing and working better together.”

Teaming puts a team’s EQ at the forefront, with transparency as the main priority. Through these sessions, Jackie strips each team down to their authentic selves, encouraging members to share their successes, and losses as they prioritize open communication above all. This vulnerability Jackie achieves through her Teaming sessions is what makes these meetings so magical: 

“I’m proud that the team was able… to show up, and not just sugarcoat or talk around the issues, we really got into the issues. I know that they felt like it impacted the health of the team moving forward.”

Do you have your own Magical Meeting Story to tell?

We’d love to hear your wizardry! Share how you are creating magical moments in your work below.