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Anchoring Questions By Mark Stevenson and Lindsay Olesberg


In our experience walking alongside executive and board leaders during crucial transitions, the difference depends on the anchoring questions driving the conversation. This has been especially true over the last few months of our work. Periods of intensified strain burden leaders and organizations, but can also become fertile ground for new seasons of growth and vitality. Buried within many crises is the potential for organizations to emerge with greater focus and alignment.

While there are a number of resources circulating today related to tactical response, scenario planning, and resource prioritization, we want to share a set of questions that can help keep focus on team and mission fidelity. We offer these questions to help your board or executive team stay connected, clear, and unified in the midst of the intense organizational stress and strain many of us are experiencing. If you are an executive or board leader, choose the questions that you feel will facilitate the most candid, clear and fruitful conversations for your work and mission.


  1. If we could ask them today, what would our founder or founding board of directors tell us not to forget in this challenging time? What wisdom might they share?
  2. To clarify our non-negotiables, what would be the most authentic and effective expression of our mission if we had half the people and resources we do now? What would we do? What wouldn’t we do?
  3. Which of our values seem hardest to “live into”in the current climate? What must we do to remain true to them?


  1. Given today’s pressures and uncertainty, what is one thing that already needed to change before Covid-19 that could ambush us in the upcoming months? How should we respond?
  2. What stress fractures are we seeing in our team work or board work together? How can we best bring those fractures into the light in a safe and honoring way?
  3. In an upcoming meeting, ask each person on the team/board to take a few minutes to describe how Covid-19 and/or recent racial injustice and unrest have personally impacted their lives.


  1. Which staff or departments have stepped forward with noteworthy skill or strength? How might we recognize and deploy that skill or strength for the benefit of the entire organization?
  2. How can we encourage or serve other organizations or leaders in need? Can we provide advice, expertise, short term staffing, technical support, or financial assistance as a show of solidarity?


  1. What are two or three ways our people can engage colleagues or leaders outside our organization for prayer, support, and perspective?
  2. How have normal patterns of personal and corporate rest, renewal, and celebration been interrupted? How can we re-imagine and practice those?


Mark Stevenson, Practice Leader, and Lindsay Olesberg, Senior Consultant, provide discernment, coaching and search services for leaders and boards of Christian organizations. Mark can be reached at and Lindsay at


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