Strategic Planning Facilitator for Boards and Executive Teams
Ross Dawson is a strategic planning facilitator who combines futurist insight with expert facilitation. He designs and runs strategy offsites, workshops, and multi-session strategy processes for boards and executive teams, bringing together the richness of the participants’ perspectives to create incisive strategy and clear action plans.
Clients often comment that the combination is unusual: a facilitator who frames the external change the organization faces, and then draws out the group’s own thinking on what to do about it. Sessions range from a single strategy day for an eight-person executive team to a leadership program of several hundred, and from a compact virtual workshop to an enterprise strategy process running over months.
How an engagement runs
- Objectives first. A briefing conversation on the strategic questions in front of the leadership team and the outcomes the session needs to produce. The objectives determine the design.
- Design and pre-framing. Content, structure, flow, and exercises designed with the CEO, strategy team, or offsite owner, with pre-work where it lifts the quality of the conversation.
- The session. Framing on external change where useful, then facilitated work that distinguishes the issues needing pointed discussion from those to park, and moves the group to decisions.
- Action plan. Clear, prioritized initiatives with owners, and where wanted a follow-up session to review progress.
Techniques
Ross draws on a range of techniques to suit the group and the objectives.
- Strategic frameworks that generate insight on industry shifts and the organization’s position.
- Scenario planning to make uncertainty usable in strategy.
- Mental model mapping to surface and align executives’ strategic thinking.
- Industry network and ecosystem analysis to identify where value is moving.
- Opportunity identification and prioritization, with digital facilitation tools that surface every participant’s view efficiently.
- AI-augmented strategy tools, including Fraxios, the AI-augmented strategy platform Ross founded, used in sessions on AI-augmented strategic decision-making to frame assumptions, generate and assess options, and stress-test decisions.
Sessions and workshops
The sessions below are illustrative examples. Every engagement is designed around the organization’s objectives.
Framing Your AI Strategy
A facilitated workshop that gives boards and executive teams clarity on the role of AI in their strategy, the priority issues, and a high-level roadmap. Discover more
AI-Augmented Strategic Decision-Making
Leading-edge AI tools applied to a live strategic decision, giving participants a faster, better-supported outcome and the ability to apply AI to future decisions. Discover more
Scenario Planning
Driving forces and critical uncertainties brought together into a set of plausible, complementary scenarios, and the responsive strategies that follow. Discover more
C-Suite Roundtables
Facilitation of CEO, CFO, CIO, and other C-level roundtables convened by technology and professional services firms and event organizers, opening with content that stimulates discussion and drawing out the participants’ experience. Discover more
Partner Offsites
Strategy sessions for the partners of professional services firms, on the future of their sector, the innovation initiatives it demands, and strategy, collaboration, and client relationships. Discover more
Formats
- Strategy offsite. Design and facilitation of the executive team’s annual offsite, from a keynote followed by structured discussion to a multi-day strategy process ending in agreed initiatives.
- Strategy workshop. Half day to full day for an executive team, board, or broader leadership group of up to several hundred, with defined outputs.
- Multi-session strategy process. Core-team framing, two or more facilitated executive sessions, and an action plan, run over weeks or months.
- Virtual facilitation. Online strategy processes using collaboration tools Ross has applied for over two decades, which often produce outcomes superior to a single in-person workshop when participants are dispersed.
- Wider engagement. Processes that bring the next tier of management, partners, or all staff into strategy, through workshops, town halls, online input, and team projects, so the organization understands and owns its strategy.
Examples of recent work
The CEO of a global construction group asked Ross to facilitate the annual three-day strategy offsite of its eight-person top executive team. He worked with the strategy group to design the content, structure, flow, and outcomes, and the offsite produced incisive action plans to drive the group’s strategy for the coming year and beyond.
A retirement living group wanted its board and executive team to understand how AI should transform its strategic planning. Ross ran a session on Humans + AI workflows in strategy, the risks and the responses to them, where accountability stays with the board, and the specific uses of AI in ideation, scenario analysis, complementary perspectives, stakeholder personas, and metric tracking.
A global infrastructure services organization brought its 100 top executives together for an offsite on industry shifts. Ross designed and facilitated a one-day workshop to scan uncertainties and identify the key issues, using internal case studies to capture insights from across the leadership team.
One of Africa’s largest media conglomerates engaged Ross to facilitate its top executive team in preparing a future-oriented strategy for the board. The process surfaced challenges, framed opportunities, and produced a framework capturing the executives’ collective insight. Ross then facilitated the board meeting at which the strategy was presented, crystallizing the board’s questions for the executive team to respond to.
A major bank brought senior stakeholders together to develop scenarios for its operations and identify emerging risks over the next three to five years. Ross worked with the risk management team to frame the issues and create the scenarios, and facilitated a workshop that established the initiatives to address them.
About Ross Dawson
Ross Dawson is a futurist, strategy advisor, keynote speaker, entrepreneur, and author. He is the Founder of Advanced Human Technologies Group, whose ventures include the Humans + AI product suite and Fraxios, the AI-augmented strategy platform, and the bestselling author of Thriving on Overload and Living Networks. He has delivered keynotes and strategy sessions in 35 countries.
