2024 Guide To Run A Strategy Workshop: Preparation, Structure, And Best Tools.

Post updated on
February 3, 2024

Strategy workshops are pivotal in steering businesses or a new product toward success.

It is such the trust we have in this type of session that we are balancing our model from full long-term consulting engagements to strategic workshops.

A strategy session offers much-needed clarity and direction for teams by discovering market insights and gaps preventing your company, product, or innovation from growing with concrete decisions and a plan and steps.

And what's best is that it is conducted in fun and engaging sessions that won't take months but hours or days to drive outcomes.

Embarking on the journey of strategic problem-solving through a workshop is more than an exercise; it's a transformative experience for your team and business!

In this article, I will drive you through the next content:

What Is A Strategy Workshop?

Strategy workshops are a powerful tool to get teams unstuck and move from problem to action in days or hours instead of months.

The primary objective of these workshops is to move quickly into solving a specific strategic problem, creating a shared vision, and having team buy-in and a coherent plan that can be effectively executed. This includes setting clear goals and developing a roadmap.

It's a convergence point where your team, senior leadership, key stakeholders, and external experts come together to discover market dynamics, customer needs, and competition and decide strategic priorities to win.

In these sessions, the agenda is carefully structured to extract the maximum creative and strategic input from all participants. Exercises can involve analyzing industry trends, identifying market opportunities, discovering company or product strengths, and discovering what customers want.

What Are The Benefits Of Hosting A Strategy Workshop?

Here are the top benefits we've heard from our clients:

  1. Quick Problem Solving / "Getting unstuck": Problem-solve a strategic issue that otherwise would take months to solve or move the needle in hours or days with your team.
  2. Team Alignment of Vision and Objectives: These workshops bring together various departments and levels of management, fostering a unified understanding and alignment of the company's vision and objectives.
  3. Enhanced Innovation and Creativity: The collaborative environment encourages exchanging ideas and perspectives. Workshops can spark new ideas for products, services, or market approaches that might not emerge in a typical office setting.
  4. Market and Competitive Insights: High-tech markets are rapidly evolving. A strategy meeting provides a dedicated space to conduct thorough market and competitor discovery, ensuring that the company's strategies are robust and well-informed.
  5. Identification of New Opportunities and Risks:  enable teams to proactively assess opportunities and risks and develop strategies to capitalize on new trends or mitigate risks.
  6. Building a Roadmap for Execution: Beyond brainstorming and planning, these working sessions are instrumental in creating actionable roadmaps. They help set realistic timelines, define key performance indicators (KPIs), and assign responsibilities, ensuring the new strategy is effectively translated into action.
  7. Adaptability to Market Changes: Given the volatile nature of the tech industry, strategies must be adaptable. The nature of these sessions makes them agile, quick to prepare, and action-oriented, helping companies quickly adjust strategies in response to new technological advancements or market shifts.
  8. Team building: Every time we run one of these workshops, we listen to the team saying to the CEO, "We should do more like this!!".

How To Prepare For A Strategy Workshop? 10 Steps To Run It Effectively

Effective preparation is critical to maximizing the benefits of a strategy meeting. This preparation is even more critical for B2B high-tech companies and innovations, where the markets and competition rapidly evolve. Here's how to get ready:

  1. Set clear objectives (THE WHY): Define the problem you want to solve and the desired outcomes. Whether developing a new product strategy, exploring emerging technologies, or refining go-to-market tactics, having clear objectives sets the tone for the workshop. This ensures that discussions are focused and productive, leading to tangible outcomes. Objectives might include defining a new product go-to-market strategy, exploring new market opportunities, or refining the company's positioning strategy.
  2. Write an agenda (THE WHAT AND HOW): Create a detailed agenda that allocates time for each topic or activity. Ensure a balance between structured discussions, creative brainstorming sessions, and practical planning. Allocate time for discovering ideas/insights (divergence) and decision-making or prioritization (convergence) for each theme you cover.
  3. Select the right workshop participants (THE WHO): The session's success depends heavily on who attends. Include a mix of company participants from different departments and levels to ensure diverse perspectives from people whose knowledge is crucial for the workshop's outcomes. Also, consider including external experts or stakeholders for additional insights.
  4. Communicate expectations: Successful workshops rely on communicating their objectives, agenda, and expected outcomes to all participants.
  5. Pre-workshop research: In the best scenario, the workshop should leverage market research, customer feedback, competitive analysis, and trends to inform discussions and strategies. This can be done with previous preparation or by hiring an external coach who brings an external, unbiased perspective to the workshop.
  6. Set the stage: Choose a conducive environment for the workshop. The setting should encourage open communication and creative thinking, whether it's an off-site location or a dedicated space within your office. Also, ensure all necessary materials and technological tools are available. You can also conduct an online session with the tools we recommend below.
  7. Expert strategy workshop facilitation: An experienced facilitator who can guide discussions, ensure all voices are heard, and keep the workshop on track is crucial. This might be an internal leader or an external coach with expertise in the high-tech industry and strategic planning.
  8. Strategic thinking & discovery techniques to help unlock new ideas and perspectives and encourage participation.
  9. Action points: The end goal of the workshop should be a set of actionable steps. This includes defining specific initiatives, assigning responsibilities, setting timelines, and determining how progress will be measured and reported.
  10. Follow-up and implementation plan: The workshop is just the beginning. Effective strategy requires a successful implementation. A follow-up plan to implement the strategies and monitor progress is essential to ensure that the insights and decisions from the workshop translate into real-world results.
Preparation differentiates between a mere discussion and a working session that leads to actionable and impactful strategic initiatives.

A well-prepared workshop is the first step towards transforming strategic ideas into real-world business successes.

What Are The Top Strategy Workshop Exercises?

Selecting the most suitable agenda for your specific problem is a decision that can significantly impact your strategic direction. Here are the typical workshops we're asked to conduct:

  • Positioning Strategy: this workshop is focused on strengthening how the market perceives your business, product, or brand. Identify your target market versus who it should be, your unique selling proposition (USP), and your competitive strengths to design a unique positioning to become the go-to solution in your market.
  • Market Opportunity Analysis: identify and evaluate potential market opportunities to grow your business. Explore segments, use cases, and industries and score them against our model to find your best business growth opportunities.
  • Crossing The Chasm Workshop: solve sales stagnation periods for high-tech businesses or innovations. Firstly, find out where you are in the technology adoption lifecycle regarding the type of buyers you're attracting. With this, diagnose what in your current strategy (positioning, messaging, sales approach, distribution) is out of alignment. Then, ideate a strategy to re-align your business with the market to accelerate your traction. This session is based on our unique understanding of the Crossing The Chasm framework.
  • Go-to-market workshop: define your strategy to enter new markets or launch a new product into an existing one.  Identify your target audience, discover their problems and pains, ideate how your product fits those problems, select the best positioning, align your offering to meet customer needs, and ideate the best distribution channels and launch sequence.
  • Product Launch or Brand Awareness: With the help of our Ecosystem Map Framework, it's an opportunity to analyze your market ecosystem, looking at all types of organizations and players in your industry, like analysts, thought leaders, consultants, industry associations, suppliers, customers, and competitors. Then, you'll define a sequence of marketing and relationship-building activities to drive word-of-mouth across those 3rd party players. This strategy can be used to validate an idea with external players, find who to partner with to strengthen your go-to-market strategy, build a marketing program to improve awareness or position your product/brand.
  • Business strategy: Discover the gaps preventing your high-tech business from becoming the go-to solution by assessing the 12 elements we've found to be the ones to build long-term success and competitive advantage in high-tech markets. This session follows our proprietary framework, refined in over 200+ B2B high-tech projects to asses your overall business strategy gaps and find solutions to solve them: The Brand Differentiation Wheel™.
  • Value Proposition Design: This session helps discover what your best-fit customers care about and hone in on what differentiates your business or product from competitors. ‍

What Are The Best Tools To Conduct A Business Strategy Workshop?

  • Butter.us provides an all-in-one platform for practical remote workshops with features like collaborative whiteboards, real-time polling, and customizable breakout rooms, ensuring seamless engagement and increased productivity.
  • Miro is a digital workspace tool offering interactive features for remote strategic workshops, including versatile whiteboards, project boards, and dynamic mapping tools - all designed to stimulate engagement and collaboration.
  • Fathom.video facilitates efficient remote workshops by offering real-time document editing, collaborative brainstorming capabilities, and seamless video communication, ensuring productivity and interactive engagement, irrespective of geographical boundaries.
  • ChatGPT will help you summarize and group the ideas and solutions by themes after the workshop by uploading the transcript. It can also assist you in strategizing new angles after the workshop ends by prompting the workshop insights.
  • If you're running an in-person workshop, ensure you have a big room, a whiteboard, sticky notes, and a place for everyone to pick their notes, write their ideas, and introduce them to everyone.

The image below is an example of a remote workshop agenda for value and offering design with Butter.

→ We're Miro Certified Consultants! Get our Miro Boards to run the workshops with your team.

How To Successfully Run Remote Working Sessions?


  • All ideas count. There are no bad ideas. Everyone talks.
  • One idea at a time. Ideas must be presented in less than 30 seconds to spark creativity and new insights.
  • Everyone has cameras on. Have a problem with the camera? You're out.
  • Use a whiteboard with sticky notes. If running it online, white boarding tools like Miro, Mural, or Microsoft Whiteboard can facilitate collaboration and visual representation of ideas.
  • Run the workshop with authority. Stick with the agenda and allocated time. Otherwise, you'll run out of time, not make decisions, and fail to achieve your desired workshop outcomes.
  • Build on the ideas of others.


  • No small talk or whispering.
  • No cell phones or tablets. 100% focus on the session.
  • There are no bosses or roles besides the facilitator and one decision-maker in the room.
  • The facilitator can not be one of the stakeholders. Facilitating the workshop is about asking the right questions at the right time, engaging people, ensuring everyone participates, and working towards the expected outcomes. A stakeholder can't do the facilitator because they must focus on participating, listening, and learning.
  • The session can not be a monologue to avoid just having the perspective of a limited number of people. Also, the session must stick with the times to ensure all the outcomes are achieved.
  • Criticize or judge other's ideas. Do you want to know what people think about the ideas? Allocate time for voting anonymously in absolute silence.

Strategy Workshop Case Study: Digital Smile Design

Instead of reading to me, listen to Brendon McDonald's, the CEO at Digital Smile Design, talk about their experience with the Positioning Strategy Workshop of this case study.

Planning Process

1 month before the strategy workshop:

  1. We had a diagnosis meeting with Brendon to define the problem to solve and pick the right strategy workshop to run.
  2. The initial definition of the problem was to "build the messaging". However, we discovered that we needed to "define the positioning strategy" before the messaging.
  3. We agreed with Brendon to define the specific goals as
  • Get the team to discover and agree on the proper context of who we serve and what problem we solve.
  • Set the foundations to define product-level positioning clearly.
  • Get the messaging process up to speed.

2 weeks before the workshop:

  1. We delivered and agreed on the workshop agenda with Brendon to achieve the desired goals.
  2. We agreed that the team members should get involved. In this case, we selected 15 experienced members from marketing, sales, customer success, head of client ops, and CEO.
  3. We communicated the structure and preparation required to the team.
  4. We booked the team agendas for 1 full day.
  5. The team involved in the workshop conducted their own research with specific questions and exercises we provided.
  6. I conducted my own market and industry research to offer an external, unbiased perspective, acting not only as a workshop facilitator but also as a coach and strategist.

Workshop Agenda

This is typically a 3-day workshop when planned to make decisions and build a plan of action.

However, we needed to condense the sessions into 1 day, so we sacrificed the decision-making time (convergence). Thus, the workshop was about discovery rather than discovery -> decision -> action item definition.

The day was structured into 7 short discovery workshop sessions. They were planned to help the brain think strategically and in a structured way: from a broad point of view (market) to a narrow one (PROBLEM).

1. MARKET Context DISCOVERY session

  • Discover what's wrong with the market in our POV. What's something my market does not see but we do?
  • WHAT IS THIS FOR: This will help us understand "the enemy" and build our Point of View to start our narrative. Also, clarify if we're creating a category.
  • TIME: 1 hour

2. WHO do we HELP THE MOST session

  • Define clearly our best-fit customer: Job Titles, Sizes, and Geographies.
  • WHAT IS THIS FOR: This will help us understand who the specific target market or ICP is.
  • TIME: 30 minutes

3. What is the end-user workflow or customer journey of the best-fit customer right now

  • Design the step-by-step workflow.
  • WHAT IS THIS FOR: Understand the overall workflow of end-users to see how we are changing their approach. Then, pick the steps we're helping improve to move into the next step.
  • TIME: 1 hour

4. WHAT PROBLEM do we solve session

  • Uncover pains/struggles/frustrations
  • Uncover goals/jobs to be done
  • Uncover the penalties
  • Uncover how they are solving it right now (status quo or competition)
  • TIME: 1 hour

5. How do we SOLVE the problem now session (our product)

  • Discover how our solution solves the pains/struggles/frustrations to achieve the job to be done.
  • Discover the business impact (outcomes).
  • 1 hour

6. WHAT IF… session

  • Discover what can go wrong in the customer's mind. What are the risks, hesitations, and frictions associated with hiring our product/service?
  • 30 minutes

7. WHY US session?

  • Discover internal strengths and weaknesses that can drive credibility toward our brand and product.
  • 30 minutes

Right after the workshop

  1. I'd record all the sticky notes with my cell phone camera and describe them loudly.
  2. I'd transcribe those notes by uploading the recording to Grain.
  3. I'd upload the transcriptions to ChatGPT and ask for summarizations and data aggregation to get a list of key themes by each session analyzed.

Post-Workshop Work

Summarizing the discoveries by theme would become the key to designing and delivering the new positioning strategy and messages.

Because this was a single workshop day without time to strategize but to discover, we had to create the strategy and the roadmap and communicate it afterward.

Workshop Outcomes

A clear understanding for the business to differentiate and become the go-to provider with concrete definitions of:

  • A clear understanding of strategic problems to solve
  • Who should we serve (best fit customers).
  • What problem or use case to focus on to stand out
  • How do their product/service capabilities help to solve the problem / use case in a way that competitors don't
  • Understanding of the motivations of today's buyers versus the motivations of tomorrow's buyers. A plan to adapt to tomorrow's motivations (forward-thinking strategy).
  • Market objections to buy the product and strategy to overcome those objections
  • Intangible differentiation attributes


Strategy workshops are a fascinating tool in strategic planning. You can quickly problem-solve a specific challenge, get team buy-in, drive collaboration, and get unstuck by running one of these workshops, selecting the right participants, and implementing effective techniques.

Clear communication and documenting outcomes are essential to drive action after the workshop, whether on-site or remote.

Talk to me to ensure a successful strategy workshop tailored to your business needs. I'm ready to guide you through the process and help you achieve your strategic objectives!

Author Photo
Jose Bermejo, Founding Partner

Thanks for reading my thoughts! I bring 16 years of experience selling and marketing B2B tech products. I'm a thinker on the impact of human behavior on innovation adoption, marketing strategy, go-to-market, and business leadership in B2B high-tech. Armed with this knowledge, I help B2B high-tech leaders accelerate traction by aligning their strategy with what buyers want as coach, speaker, and workshop leader.

Let's connect