- Explore key components of design theory and design thinking practices
- Define the CURRENT STATE and FUTURE STATE of the team’s collective goals and objectives
- Experiment with the concept of a DESIGN SPRINT to generate creative, implementable action plans to fully realize the ideal future state
- Leverage principles from positive psychology to frame suggestions in future-focused, strengths-based, behavior-driven language
- Develop an action and implementation plan of new leadership competencies
Creative Thinking Design Sprint
Mission Possible: Strategic and
Creative Thinking Design Sprint
Designing the Future State of
Our Team and Organization
Before an individual or team can build the future, they need to see it together with the kind of shared clarity, alignment, and energy that turns vision into action. Determining key long-term goals and objectives is the crucial first step to informing everything a team does day-to-day with purpose and direction. But most strategic planning processes leave people feeling like spectators rather than architects of what comes next.
This strategic planning and design thinking workshop changes that. Grounded in the foundational principles of positive psychology and design thinking methodology, Mission Possible gives teams a structured, energizing process to define their ideal future state and prototype the roadmap to get there. Through a facilitated Design Sprint, participants move from broad individual or organizational vision to concrete, implementable action plans, using design theory to ideate, discover, and prototype the initial steps that bring their ideas to life. Participants leave with clarity on where they are going, energized about how they will get there, and equipped with a detailed action plan to make it real.
What You'll Learn
During this strategic planning and design thinking workshop, participants will:
Leadership Behaviors You'll Develop
As a result of this session, participants will be able to enhance their leadership capabilities through the following behaviors:
- Reframing challenges as actionable plans to enact meaningful, lasting change
- Setting others up for success when executing a shared and clearly articulated vision
- Challenging the status quo for outside-the-box, possibility-forward thinking
- Maintaining a culture of positive, collaborative brainstorming and open communication
- Embracing a YES, AND mentality to build trust and enhance collaboration throughout the organization
Who Is This Workshop For?
This workshop is ideal for leadership teams, department heads, and cross-functional groups ready to align on a shared vision and take concrete steps toward it together. It is a particularly powerful session for organizations at a pivotal strategic moment, whether navigating growth, change, or a bold new direction, and looking for a structured, energizing way to move forward with clarity and momentum.
Related Workshops
Learning Objectives:
- Identify current decision making practices, both on an individual and team level
- Discover The Four Phases of Team Development, overlaying the model to spark dialogue on the current state of team dynamics
- Measure individual and team-based decision making success, and develop an action and implementation plan of new leadership competencies
Key Themes & Leadership Behaviors:
- Data-Based Decision Making
- Consensus Building
- Effective Communication
Learning Objectives:
- Differentiate between the topics of CHANGE and TRANSITION, exploring “the people side” of change
- Identify key actions to successfully navigate each phase of transition
- Develop an action + implementation plan, fit with details of specific steps to support others during times of ambiguity
Key Themes & Leadership Behaviors:
- Change Agility + Adaptability
- Increased Empathy + Awareness
- Team-Focused Strategy + Mindset
Learning Objectives:
- Identify current decision making practices, both on an individual and team level
- Discover The Four Phases of Team Development, overlaying the model to spark dialogue on the current state of team dynamics
- Measure individual and team-based decision making success, and develop an action and implementation plan of new leadership competencies
Key Themes & Leadership Behaviors:
- Data-Based Decision Making
- Consensus Building
- Effective Communication
Learning Objectives:
- Differentiate between the topics of CHANGE and TRANSITION, exploring “the people side” of change
- Identify key actions to successfully navigate each phase of transition
- Develop an action + implementation plan, fit with details of specific steps to support others during times of ambiguity
Key Themes & Leadership Behaviors:
- Change Agility + Adaptability
- Increased Empathy + Awareness
- Team-Focused Strategy + Mindset
Learning Objectives:
- Strategize the current state of your team, assessing and identifying current levels of performance and potential
- Experiment with talent development tools to more accurately articulate your development strategy to grow and engage with your top talent
- Develop an action + implementation plan, fit with details of specific steps to support others during times of ambiguity
Key Themes & Leadership Behaviors:
- Talent Strategy + Development
- Empowering + Developing Others
- Executing Team Vision + Development Goals
Learning Objectives:
- Experiment with interactive exercises to enhance active listening, setting others up for success, challenging the status-quo, and confidently stepping outside of our comfort zones
- Embrace the concept of “YES, AND” to build upon the ideas of others in an effort to strengthen interpersonal, team, and organizational relationships
- Develop an action + implementation plan for positive, long-term behavior change
Key Themes & Leadership Behaviors:
- Collaboration + Trust
- Effective Communication
- Openness to Change + Innovation
Learning Objectives:
- Strategize the current state of your team, assessing and identifying current levels of performance and potential
- Experiment with talent development tools to more accurately articulate your development strategy to grow and engage with your top talent
- Develop an action + implementation plan, fit with details of specific steps to support others during times of ambiguity
Key Themes & Leadership Behaviors:
- Talent Strategy + Development
- Empowering + Developing Others
- Executing Team Vision + Development Goals
Learning Objectives:
- Experiment with interactive exercises to enhance active listening, setting others up for success, challenging the status-quo, and confidently stepping outside of our comfort zones
- Embrace the concept of “YES, AND” to build upon the ideas of others in an effort to strengthen interpersonal, team, and organizational relationships
- Develop an action + implementation plan for positive, long-term behavior change
Key Themes & Leadership Behaviors:
- Collaboration + Trust
- Effective Communication
- Openness to Change + Innovation
View More Workshops
View More Workshops
Frequently Asked Questions
What is a Design Sprint and how is it used in this strategic planning workshop?
A Design Sprint is a structured, time-boxed process for rapidly generating and prototyping solutions to complex challenges. In this workshop, the sprint framework is adapted to help leadership teams move from broad organizational vision to concrete, implementable first steps, translating shared aspirations into action plans with real energy and momentum behind them.
How does positive psychology shape the strategic planning process in this workshop?
Positive psychology provides a strengths-based, future-focused lens for organizational planning. Rather than leading with problems to diagnose and fix, this approach helps teams articulate what they want to build and frame their goals in positive, behavior-based language. The result is a planning process that feels genuinely energizing and generates more creative, sustainable, and commitment-worthy outcomes.
What is the difference between Current State and Future State in this design thinking framework?
The workshop begins with the Current State: a grounded, honest look at where the team is today, including its strengths, opportunities, and aspirations. The Future State is the articulated vision of where the strategist wants to go. The Design Sprint bridges the two, generating actionable ideas and initial prototypes that give the team a clear, confident path from where they are to where they are going.
Is Mission Possible a good fit for annual planning, strategy sessions, or leadership off-sites?
It is an excellent fit for all three. The workshop's collaborative, high-energy format makes it ideal for any setting where a team needs to align on direction, generate bold new ideas, and build genuine shared momentum around what comes next. Many organizations use it as their annual planning anchor for exactly this reason.
What does a team walk away with at the end of this design sprint workshop?
Teams leave with a clearly articulated shared vision of their ideal future state, a set of prototyped action ideas generated through the Design Sprint, and initial implementation plans to bring those ideas to life. The focus is equally on the destination and on building an aligned, energized team ready to pursue it together.

Jacob Goldstein
Jacob Goldstein is the founder of The Leadership Laboratory, and leverages his experiences in education, the performing arts, and corporate learning & leadership development to his work. As a performer, Jacob has sung as a backup vocalist for musical artists such as Josh Groban, Idina Menzel, and Patti LuPone, as a recording artist for Netflix series Sense8, and at venues including The United Center, The Chicago Theater, and Chicago Symphony Center. In the education space, Jacob has served as an educator for high school, undergraduate and graduate students, and has been a Guest Lecturer at Northwestern University since 2016. As a Learning & Leadership Development Consultant, Jacob has worked as a one-on-one coach and group workshop facilitator to organizations ranging from startups to Fortune 500 companies in diverse industries, including technology, healthcare, non-profit, and fashion/apparel. Jacob holds a Bachelor’s degree from The University of Illinois at Urbana-Champaign, and a Master’s of Science in Communication from Northwestern University.
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