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BOSS Wargames

BOSS Wargaming allows entrepreneurs and investors the ability to experience, learn from and plan for future events in the present. Until now startups have relied on historical data and Artificial Intelligence tools to predict and plan for the future.

Unfortunately, this approach does not answer the “what if” questions that keep so many entrepreneurs and investors up at night. Questions like, what if in the next 3 years there is a consolidation of my top competitors, or what if there is an economic recession or a global pandemic? Will these scenarios have a positive or negative impact on your company? Will you be prepared to react? Will your exit strategy be impacted?

BOSS Wargaming puts entrepreneurs and investors in control of their destiny and allows startups to make decisions now that will prepare them for success in the future.

The 7-Steps to BOSS Wargaming

  1. Determine your scenario. What things do you need to learn?

  2. Select your “Control” team. They will build, run and help assess the game

  3. Outline your scenario. Based on the stage and exercise in BOSS

  4. Review the move sequence. 3 time-bound moves per game

  5. Select your Home and Away teams. Teams who will compete during the game

  6. Play the Game. Games can be virtual or in-person and limited to 3 hours

  7. Assess and share the outcome. Share the outcome across the organization and implement changes

1. Determine Scenario. As you progress through the BOSS tools and templates, you will find that some exercises in the North Star and BOSS Sheet are marked with the wargaming icon. When you see this icon, you and your team will use the predetermined objective to develop your custom scenario.

The first step in the wargame is to determine your scenario. Without clarity on your scenario, it will be impossible to craft an effective game. To keep the game manageable, it is best to focus on one scenario. The scenario will evolve throughout the game as moves are made and factors are considered. When initially considering objectives, it is best to phrase them in the form of questions. Examples include:

North Star – Ideal Customer Profile, Ideal Acquirer Profile, Exit Strategy

  • What niche in my market should I seek to fill (what can I do better, faster or more efficiently than the other competitors?)

  • Have we identified the best exit strategy for our identified Ideal Acquirer Profile?

BOSS Sheet – Go-to-Market

  • What Missions must be met to get to the next milestone, and how will competitors, investors or market conditions impact us?

  • Are there opportunities to “Leapfrog” ahead by leveraging a subset of our product or resources?

  • Should we move sales and marketing under the leadership of a CRO, or keep them separate?

  • Is our customer feedback process optimized to allow for actionable insights?


  • Is our North Star still viable?

  • Is our Strategy still viable?

  • Given market changes, how can we quickly pivot to employ our resources to capture new opportunities?

2. Pick Your Control Team. The second most important decision is selecting your “Control” team. These are the people who will design your game, help select the players, facilitate game play and assist with assessment of the results. In small organizations, it can be a single person. They should be broadly knowledgeable but do not need to be expert in all (or any) aspects of the company, market, etc. The most critical personality traits in a good Control member are:

  1. Creative thinking and chronic rejection of “how it’s always been done”

  2. Low ego – able to ask questions without being intimidating, and accept multiple points of view on any topic

  3. Confident enough to ‘speak truth to power’

  4. Marketing and Sales leaders tend to make great Control members since they are naturally outgoing and should be familiar with their own company’s strengths and weaknesses as well as those of their competitors.

3. Outline Your Scenario. Your “Control” team creates and manages the scenario. The scenario should be realistic, but need not be comprehensive or entirely based on current facts. It is fine to make assumptions on things you don’t, or can’t, know. However, it is critical that all of the assumptions be explicit and that you document them, because as the reality of what you assumed becomes known, you will need to re-interpret your game assessment to see if it remains valid.

The key scenario elements you must decide on are:

  1. Time: in what time period does the game start, and how far into the future should it go?

  2. Environment: are you playing in the entire world; a single region or country; an industry; a business segment?

  3. Factors: “Factors” are discrete events or challenges that are inserted by Control during the game (normally between moves) that force the participants to deal with the most important elements of reaching the objective. During game development, the Control team should develop a “menu” of factors that can be selected from, based on which direction the participants decide to go. Examples of factors include:

    1. Specific changes in regulation and compliance. Collapse of an investor syndicate.

    2. Loss of a key company leader.

    3. Revelation that a new competitor has entered the market.

    4. Social movements that change the market’s impression of your product.

4. Select your Home and Away teams. After the scenario is complete, the “Control” team selects a “Home” team and “Away” team to compete in the game. These two teams will go head-to-head, reacting to conditions set forth by the “Control” team.

  • The “Home” team: This team represents your company during the war game. They are expected to play the game according to the same values and resources your company commands.

  • The “Away” team: This team represents your competition and/or external factors that can put your company at risk. Competitors can be existing or emerging and plays the game with the objective of succeeding in the same market as the home team.

5. Identify Your Move Sequence. Your move sequence is critical and should be timebound. Each game involves 3 moves made by “Home” and “Away” teams. Before each move the “Control” team discusses the scenario and presents the “injects” the teams will need to account for when dimensioning and presenting their move. The teams then have 30 minutes to plan their moves, once completed each team is given 5 minutes to present their move to the group. After the presentation the competing team is given 5 minutes to challenge the opposing teams move.

Following the completion of the teams moves, the “Control” team gathers and documents each move and then has 30 minutes to update the scenario and prepare “factors” for the next move.

After the 3rd move, the “Control” team assesses the game moves and outcomes and presents their findings to the group.

6. Play the game. Using the BOSS Gameboard, you and your team execute the 3 moves of the game.

BOSS Gameboard

7. Assess the Outcome. The Control team, along with others – as time and resources permit – should assess the game within 48 hours of its conclusion. They should start with the material provided directly by the game, but also exercise independent judgment, with the benefit of hindsight and time for reflection, to draw their own conclusions as well.

The game assessment can take any form that’s useful, but should – at a minimum – include the following elements:

  • Complete SWOT analysis on solutions

  • Executive Summary with recommendations

  • List of the players and teams

  • Brief overview of the scenario with key assumptions

  • By-move discussion of the options considered by each team and which were ultimately chosen

BOSS Wargaming allows your company to role-play future events giving you an exponential advantage over your competition. Your company will be able to exhaust the validity of your key business decisions, like your exit strategy and GTM strategy, so you can be confident about your ability to grow through any scenario.


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