How to facilitate a Business Strategy Workshop

Maxim Atanassov
12 min readSep 28, 2022
How to facilitate a Business Strategy Workshop

Company success is defined by a vision, where are you going, execution, how fast can you get there, and ethics, how will you care for the stakeholders.

The world of business is highly dynamic and continuously evolving. As such, the internal and external factors a company faces change in tandem. This can produce ambiguity and obscurity over time. It doesn’t matter how fast you are moving if you don’t know where you are going.

This can be addressed by having a proper strategy. And, in truth, the best way to design a robust strategy is through the contribution made by different strategic components of the company.

To achieve this, there are different methods, but one of the most effective, if carried out correctly, is the business strategy workshop. We favour the Merlin Method for visioning. Merlin is a method for backwards planning. This allows the leadership team to project an image of success 3 to 5 years into the future and define:

  • What do we (as in the company) want to be known for?
  • What are the roadblocks standing in our way?
  • What could go wrong?
  • What must go right?
  • What are the risks to and from the strategy?

his produces clarity and alignment for the leadership team in terms of the strategy. The Merlin Method excels at answering the What and Why questions. We like to use the Objectives and Key Results (OKR) to answer all of the other questions of Who, How, When, as well as What and Why at the next layers in the organization.

OKR is a goal-setting framework used by individuals, teams, and organizations to define measurable goals and track their outcomes. As the saying goes, what gets measured, gets done. OKR is also an incredibly powerful change management instrument as it has the ability to create an alignment from the top of the organization. The greater the alignment, the faster the organization moves. It is probably the best framework that exists to drive outcomes and has become the defacto standard in the tech industry.

In this article we will explain how to go about a strategy setting, through a workshop, but also what you should keep in mind when designing it, so that it is really effective.

What is a strategy workshop?

Strategic workshops are meetings specially designed to create an environment that motivates a strategic group of people in an organization to contribute ideas to improve the direction of the company. These individuals may include senior managers or decision-makers, as well as people who can bring strategic and valuable insights to the process.

Objectives of a Workshop

The main objective of the workshop is to obtain information to develop a strategic plan for the organization. This can help the group reach agreement on the objectives and vision that the organization should have. At the same time, it allows the organization to plan the actions that will allow it to get to where it wants to be.

How do you prepare for a business strategy workshop?

Just like with an iceberg, only a small portion (less than 15%) is visible above the surface. Most of the mass of an iceberg lies below the surface of the water. This is where the phrase “tip of the iceberg” comes from, meaning only part of an idea or problem is known. As such, what lies below the surface is all the preparation work that needs to be done, culminating in the actual workshop meeting, or what is visible above the surface.

Here are some of the key elements to keep in mind in preparing for an effective business strategy session:

1. Define what constitutes success for the workshop

It is impossible to know how to get there if you don’t know where you are going. Establish a clear objective of what you want to achieve in the workshop. This way, you will be able to prevent the discussion from straying into topics that are far removed from the real objective. Also, if you establish your objective first, then it will be much easier for you to plan the rest of the workshop.

2. Establish an agenda

Next, you will need to develop an agenda, with the topics to be covered in the workshop. Try not to be too long, so as not to deviate from the main objective of the workshop, but also make sure you don’t leave anything relevant out. The ideal duration of each topic to be discussed should be between 20 and 30 minutes.

3. Identify a skilled workshop facilitator

Facilitation, like any other skill, is a skill that is mastered over time. Identify a facilitator from within or outside the organization that can fulfill this role. The benefit of having an internal person, from Organizational Effectiveness or Change Management, is that they know the organization well. The drawback is that they are impeded by internal relationships or reporting lines and are not able to bring a valuable external industry perspective. Having the most senior person lead the discussion is rarely the right answer, unless they are a skilled facilitator.

4. Select the workshop participants

Keeping in mind the success criteria and agenda for the workshop, you should carefully think about who are the people that can contribute in a meaningful day to the success of the workshop. Subject matter expertise and diversity of thought are paramount here.

For example, if the meeting will be for a team or department, then you can invite all employees in that area of ​​the company. Now, if the objective of the meeting is the development of a comprehensive business strategy, then you should think about inviting only the leaders of each department of the company.

The key risks that you need to address here are blind spots and working off hypotheses. Identify who are the right contributors to ensure that this risk is mitigated and assign them roles in preparation for the workshop.

5. Choose a date that fits everyone

Make sure to take into account the calendar of each participant when setting a date for the workshop, before sending the invitations. For this, you should choose a date that is not excessively loaded with tasks or meetings, so that all of the workshop participants can be 100% focused on the workshop.

6. Assign responsibilities and accountabilities

Once you have carefully selected the workshop participants, assign each one of them roles in preparation for the workshop. We find that the most effective strategy discussions are the ones in which the leader of a particular department or function presents the strategy for their group to her/his peers.

The peers have the ability to ask insightful questions that help that particular leader shore up any gaps or go back to their team for further work. The facilitator’s role is to ensure that the conversation stays on track to meet the workshop objectives. The role of the leader of the company is to ensure that the individual department strategies are in service to the overall, one organization, strategy.

7. Send the necessary information to each attendee in advance

Preparation equals success. Along with the invitation, remember to send the information you consider relevant for the workshop to each attendee. It can be a graph with statistics on a topic or even reports on the development of a new product. This will allow everyone to be up to date and to make the most of the workshop.

8. Prepare, prepare, prepare

How well the meeting runs and whether the meeting achieves its intended objectives is a derivative of how well prepared the leadership team is for the meeting. Each person attending the workshop should have clear accountability to prepare, present and be ready to answer any questions pertaining to their domain. Each person should review the pre-work contributions of others prior to the meeting.

Ensure that the right environment is set for an effective meeting. To reduce distractions, these meetings are best held off-site. Be it in person or virtual, ensure that the right tools and technology are in place to execute the discussion. Goes without saying that everyone should stay hydrated and fed.

9. Enable circular and iterative feedback

Create transparency by using polling or brainstorming tools to generate ideas and create a feedback loop.

How do you structure and run a business strategy workshop?

Here is a basic structure that you can use in your next business strategy meeting:

1. Restate the outcome for the workshop

Before starting the meeting, you should re-establish the objective of what you want to achieve in the workshop. This way, you will be able to prevent the discussion from straying into topics that are far removed from the real objective.

2. Set the ground rules and set the context

Before starting to discuss the topics, it is necessary to introduce them to those present, so that everyone is clear about what is going to be discussed at the meeting. It is also advisable to make clear certain rules of coexistence, so that everyone can make the best use of the workshop.

Workshops often get dominated by Type A and extrovert leaning personalities. Ensure the right environment for equal contributions, regardless of your personality and leanings. This will allow not only to have contributions from the right people, but also to unify criteria and for everyone to be clear about their tasks to carry out the strategy. Strength comes from diversity.

Any ideas that are cursory to the discussion should be put on a “parking lot” board and revisit at a later time.

3. Break the ice

A good way to start the workshop is by breaking the ice, so that participants feel more comfortable, relaxed and committed to the meeting. Break the ice with some games among the attendees, such as dividing them into teams and asking them to each make a list of possible solutions to a given problem.

4. Encourage and foster collaboration

Teamwork is essential here, so a good strategy is to divide the discussion into smaller teams. Vary the team and the team composition based upon the subject matter at hand. Bring the discussion back to the entire team for careful examination and contribution. This will drive robustness, clarity and alignment.

5. Emphasize organization over functions

Focus on what is the right answer for the overall organization over the long term. This may mean that a new strategy may result in existing revenue channels being cannibalized in the short-term or abandoned altogether.

For example, it was Kodak that invented digital photography. Yet, in an effort not to cannibalize their existing film, processing and paper business, they never pursued their invention, ultimately resulting in their demise. Don’t be a Kodak.

6. Be bold, be brave, be creative

Enable blue sky, blank canvas thinking. Incremental innovation is important but competitive positioning could only be achieved by defining your North Star and following it like a skilled sailor. Don’t be afraid of big bets. If you have done your homework, those are the ones that will pay off handsomely and propel your company into the future. Be bold! Be brave!

Also, be creative! There are no dumb ideas. If the idea is obvious, the chances are that your competitors are also pursuing it. Enable an open and creative discussion. A good way to remove any inhibitors is with a brainstorming exercise and allow people to vote anonymously on the Top 10 ideas generated in the room.

Once you have a tally of those ideas, delve deeper in hashing them out by inviting an open discussion. Then score and prioritize based on the established North Star(s).

An alternative brainstorming exercise to generate input from everyone is to plan 4 work cycles, of 5 minutes each. In every cycle, each participant must list possible solutions to a problem that you have previously raised.

In addition, at the end of all sessions you can use a presentation to show in a clear and interactive way how the new communication strategy of the company will look like, as well as some key concepts that have emerged during the session.

7. Bring an open mind

Remember that one of the goals of the workshop is that all attendees have the opportunity to contribute their ideas. For this reason, make sure you listen to them all and give space for everyone to make contributions. Also, don’t forget to bring an inquisitive mindset. Be ready to ask questions that seek to understand a position better.

8. Take notes

A very important thing, that helps to remember the key points that came up in the meeting, is to take notes. To do this, it is advisable that you designate a person in charge of taking notes, so that you can focus on moderating the workshop, but if you wish you can do it yourself.

9. Q&A

It is always a good idea to end a workshop with an invitation to all the participants to ask questions. The workshop participant should walk away with crystal clarity about everything that has been discussed. This will reduce churn and stray.

10. Task assignment

At the end of the workshop, assign responsibilities and accountabilities. This will allow all participants and departments of the company to be clear about what they must do to carry out the strategy that has been reached in the meeting.

11. Cascade

Once the strategy is defined at the highest level, each individual leader should cascade the strategy down and execute the same strategy workshops with their team. The goal is to add more and more specificity in answering the How as well as to create clarity and alignment in the organization.

That way, from the very top of the organization to the very bottom everyone is clear on what they are working towards, and how their work contributes to the achievement of the strategy.

Business strategy pre-workshop exercises

Here are some ideas on how the individual leaders can generate ideas and input from their teams in preparation for the strategy workshop.

The Solution Board

This exercise is perfect to get the creativity of your team flowing, since the main objective is for them to express their idea on a topic in a short period of time.

For this, you can give whiteboards or notebooks to each of the attendees, and raise a possible problem or challenge that the company is facing. Then, each participant will have 5 minutes to write various solutions, which will then be discussed amongst all to select the best one and identify a suitable alternative.

After that, the team should do the necessary work to identify all the risks to this solution, what opportunities it unlocks and so on. The goal is to be well-equipped with tangible information heading into the strategy workshop.

SWOT Exercise

The SWOT (Strengths, Weaknesses, Opportunities and Threats) is perfect for mapping where the organization lies on the competitive landscape horizon. We have worked with many leaders who refuse to pursue an opportunity where they cannot become the #1 or #2 player in the space.

To develop it, you can use a grid with four columns, where each member of the department must place what, in their opinion, are the strengths, weaknesses, opportunities and threats. This type of exercise is perfect for encouraging dialogue between team members.

The team can then map the organization against its primary competitors.

Dragon’s Den

Dragon’s Den is a fairly simple activity, since it consists of asking each of the leaders what they think is the greatest need for the business. After everyone answers the question, a group discussion ensues on what could be done to improve that aspect of the company.

This exercise allows you to have a comprehensive vision of the things that can be improved in each department or function.

Employee Engagement Survey

This exercise provides an important pulse check of the most important stakeholder group of a company: its employees. Polling company employees is an effective way to find out their opinion of the company and the work environment in which they work on a daily basis.

Harvard Business Review (HBR) famously defined about four decades ago that “culture eats strategy for lunch”. While we couldn’t agree more that culture is of paramount importance, based on our experience, we believe that you can’t have culture without strategy, and you can’t be successful in executing a strategy without building and fostering the right culture.

Culture consists of a series of statements in which each employee must mark whether they agree or not. We, personally, find a hybrid of statements and open-ended questions to be more effective. It is far better to have fewer, carefully constructed questions than a barrage of questions that the survey respondents complete so that they can get to the end of the survey. Our favorite two questions are:

  • What do you wish that you could do that you are not doing currently?
  • What do you wish that you could stop doing?

Depending on the organization’s culture, this exercise may be more effective if done anonymously. The surest way to create engagement is to action the feedback, create transparency and drive change.

Final thoughts

Setting the strategy is not a “once and done” activity. After you define the North Star for the company, you need to stay true to it, and on course. In order to do these things, you must develop the OKRs, and promulgate them across the organization.

You also need to make sure to evaluate continuously the progress of the company in these aspects, while having a good communication with the leaders and the teams. Finally, remember that the feedback of your employees is key to achieve the goals. This will help you to drive transparency and build engagement in your company.

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Maxim Atanassov

Serial entrepreneur, founder, investor, board member with a passion to support founders who are hell bent on defining the future.