Most boards spend at least one full day per year together to develop, consider, endorse, or review strategy. Some boards will have several of these ‘deep dive’ strategy offsite meetings per year. Many directors consider these strategy days their most valuable contribution throughout the year.

To help you create offsite meetings that really drive great  performance, we have put together this list of questions.

The questions below provide comprehensive coverage across:

  • Objectives and outcomes
  • People and process
  • Pre-reading and content
  • Facilitation and conduct
  • Follow-up and alignment

The questions are designed to start you thinking about issues that you may encounter. Your answers are not necessarily good or bad; they should reflect the current and desired state of your understanding of the board and its role in your company.

Trust yourself to recognise the most important questions to help you get the best possible workshop designed to maximise progress with your board and directors.

At the end of the checklist, we have listed some references that you may wish to investigate for additional reading on the topic. We have also included some suggestions for putting into action the ideas that result from considering the checklist.

Objectives and outcomes

1. What precisely is the board trying to achieve? Are you looking for new ideas, looking to implement an idea, making a choice between alternatives, bringing together diverse viewpoints to create an agreed ‘board view’ of an issue, endorsing or finalising a plan, or something else?
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2. What is the single most important thing that the organisation needs to achieve from this workshop?
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3. What will the board and management have at the end of the meeting that you don’t have now?
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4. Would everyone across the board and management team agree with your assessment of the most important outcome? Who would disagree? What outcome would they prefer? How does it align to your desired outcome?
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5. How much is reasonable to cover without the day moving from a working session to a useless information dump?
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6. What will be the cost to the business if the day is not a success? Can you quantify it in hours of work required, dollars, or lost market share and momentum?
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People and process

7. Who is the natural owner of the day? Typically materials and workshops will need an owner from the management team (which will often be the CEO or head of strategy)
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8. What is the role of the board at this meeting? Are you making a decision, providing oversight, or giving inputs?
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9. Does your board have the power to make the required decisions or do you need to involve a stakeholder?
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10. Who from the management team will have useful knowledge or be critical in implementing any decision?
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11. Does your board need to access external experts who will provide credibility and information?
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12. Is there anyone who needs to know the outcome but not to attend the meeting? How will the outcome be communicated to those people?
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Pre-reading, prior activities, and content

13. What do non board members need to know to help them present effectively to the board?
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14. What do directors need to know before they can make the decision? What information or context do they already know but need to be reminded of?
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15. What is the most effective way to convey the knowledge required? Can they read and understand it? Will pre-meeting briefings be more effective?
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16. Would a strategy pre-diagnostic help to gather information so that time in the session is spent adding value without the distraction of tangents?
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17. How much time will it take to assimilate the information? Remember that directors will want to read and understand it, then to make their own specific inquiries to verify and contextualise the information.
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Facilitation and conduct

18. Who are the board’s most trusted experts on the topics relevant to the meeting? How will they be engaged in the discussion?
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19. Does the session need a trained facilitator to ensure involvement and participation across the board and management team? Does the organisation have trusted facilitators who regularly work with the executive team who could be involved in the session?
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20. Has the facilitator been briefed on the non-negotiable outcomes that must be achieved at the meeting?
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21. Has the facilitator provided an outline of the sessions? Does it look likely to result in the desired outcome? Does the facilitator have alternatives to any activities so that you have some flexibility on the day?
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22. How will the facilitator manage the interaction with the Chair? Remember that the chair is the natural leader of the board; how will the facilitator prevent that leadership from inadvertently dominating the outcome? How will the facilitator use the Chair to endorse the outcomes with the board?
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23. How will the facilitator manage the interaction with the CEO? Remember that the CEO is the natural leader of the organisation and will hold a great deal of sway with the board as well as any executives present. How will the facilitator use the CEO to socialise the outcomes with management after the strategy session is completed?
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Follow-up, accountability and alignment

24. How will any actions that are agreed as part of the outcome be recorded?
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25. Does the board need to have a short board meeting at the end of the strategy session to formalise decisions?
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26. How will the necessary permissions, delegations and/or instructions be communicated to staff who were not present?
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27. Who will check the alignment between the outcomes of the workshop and the current plans, strategies, and budgets?
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28. How will changes to plans, strategies and budgets be communicated and enforced?
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29. Who is accountable for implementing the decisions made?
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30. When will the board receive reports on the progress with implementing the decisions? What form will these reports take?
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31. At what point will the board review their decisions and the process to achieve them?
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32. How will you capture reflections from that review for input to the process of creating the next board strategy offsite?
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Taking action

Read the questions and note which ones you can confidently answer. Make a record of any actions that you wish to take to help answer any questions that you were not confident about.

Make sure that the event is planned with plenty of time to make thorough preparations. Ensure that the design of the event is not delegated to a staff member who does not have the authority to compel others to modify their expectations. It is important that pre-reading is submitted in time and is edited to the specified length.

Ensure that the chair and CEO are across all the decisions that you, as organiser, have made about the event.

Additional reading and reference sources

  • Designing & Leading Life-Changing Workshops: Creating the Conditions for Transformation in Your Groups, Trainings, and Retreats by Lesli Long, David Ronka, and Ken Nelson
  • Strategy Workshop Toolkit by Paul Christodoulou
  • Mastering Strategy Workshops for Business Success by Michael Braun and Scott Latham