Strategy Development

Most strategy development engagements span 4–12 weeks from initial discovery through final strategy documentation.

The strategy sessions themselves typically unfold over 4–8 weeks, while discovery interviews, assessments, and alignment work may extend the overall timeline depending on your organization’s size, complexity, and decision-making structure.

Strategy sessions are highly interactive, facilitated working sessions where your leadership team works through critical strategic decisions together. Bill guides the conversation, ensuring every voice is heard while helping the group stay focused on the decisions that matter most.

Most engagements are structured as a series of half-day sessions to allow for deeper thinking without burnout. Full-day sessions are possible when needed, but shorter working sessions have proven to be more effective for sustained engagement and thoughtful dialogue.

Bill offers both options and can recommend the best format for your situation. Many organizations prefer in-person facilitation for key strategy sessions because it maximizes engagement and builds stronger alignment. However, Bill has successfully facilitated virtual strategy development using interactive tools and structured approaches designed specifically for remote collaboration. Hybrid approaches are also possible, with some discovery work virtual and core sessions in-person.

Bill has successfully facilitated strategy for organizations ranging from 50 to 25,000+ employees. What matters most isn't your organization's size—it's your leadership team's readiness to engage honestly in strategic dialogue and commitment to turning strategy into action. If your team is prepared to make difficult decisions about priorities and tradeoffs, you're a good fit.

Bill's strategic facilitation approach works across industries because it focuses on fundamental leadership challenges that every organization faces: clarity, alignment, adaptability, and execution. His clients span manufacturing, healthcare, financial services, professional services, nonprofits, associations, and more. The frameworks are industry-agnostic, while the facilitation is deeply customized to your specific context and challenges.

No. Bill works with organizations at various stages of strategic maturity. Whether you're developing your first formal strategy, refining an existing plan that isn't working, pivoting due to disruption, or creating a multi-year strategic roadmap. In fact, if your existing strategic plan has become outdated or ineffective, that's often the perfect time to engage Bill to help you build something more adaptive.

Traditional strategic planning consultants often impose a rigid methodology and create impressive documents that sit on shelves. Bill's approach is fundamentally different in three ways: (1) He builds your team's capability to think strategically, not dependent on him or The Persimmon Group's consultants. (2) He creates adaptive strategies designed to evolve with changing circumstances, not rigid five-year plans. (3) He can provide ongoing strategic partnership beyond the initial engagement, not just deliver and disappear. The goal is strategy you'll actually use, not another binder for your bookshelf.

Even excellent internal leaders face challenges facilitating their own strategy sessions: they have predetermined viewpoints, must manage internal politics carefully, and can't simultaneously lead the discussion while participating in strategic thinking. Bill brings three critical advantages: (1) Objective outside perspective that challenges assumptions constructively. (2) Proven frameworks from working with diverse organizations facing similar challenges. (3) Expert facilitation skills that surface issues, navigate conflicts, and build genuine alignment—not just surface agreement.

You'll receive comprehensive strategy documentation including clearly defined outcomes, measurable goals and metrics, strategic initiatives with priorities, decision-making frameworks to guide execution, and resource allocation recommendations. More importantly, you'll have something that can't be documented: a leadership team that genuinely understands and is aligned on where you're headed, why it matters, and how you'll get there. The documented strategy is valuable; the clarity and commitment your team gains is invaluable.

Bill helps you establish meaningful metrics and milestones during the engagement—these are specific indicators that tell you whether you're making progress or need to adapt. Unlike vanity metrics, these are tied directly to your desired outcomes. Bill can also provide ongoing strategic advisory support through quarterly check-ins, helping you assess what's working, what needs adjustment, and whether circumstances warrant strategic pivots.

At minimum, your C-suite or executive leadership team should participate fully in strategy sessions. Depending on your organization's structure, this might include the CEO, CFO, COO, and heads of major functions or divisions. For some organizations, it's valuable to include the next level down—directors or senior managers who will lead strategic initiatives. Bill works with you during discovery to determine the ideal participants based on your decision-making structure and strategic challenges.

Bill conducts discovery interviews with key leaders to understand your current reality, challenges, and aspirations. Some organizations also complete brief assessments or provide key documents (current plans, financial data, market analysis) for Bill to review. The pre-work is designed to be manageable while ensuring Bill enters facilitation sessions with deep understanding of your context. Most leaders find the discovery conversations valuable in themselves—they often spark insights before formal sessions even begin.

Strategy development engagements are structured as fixed-fee projects. We work with you to craft a tailored framework aligned with your organization’s size, complexity, and desired outcomes. After an initial consultation about your strategic challenges and goals, The Persimmon Group provides a clear proposal outlining the scope, timeline, deliverables, and investment.

This ensures your investment is aligned to your specific situation rather than a one-size-fits-all approach.

Yes. We meet you where you are. Some organizations begin with a small series of facilitated sessions, during which Bill helps them clarify priorities and define their next steps forward.

These initial sessions create immediate value while also allowing both parties to assess fit for a longer-term partnership.

That depends on what you need. Some organizations want Bill available for ongoing strategic advisory support—typically quarterly strategic check-ins, availability for ad-hoc guidance on significant decisions, and facilitation support when the strategy requires updates or pivots. Other organizations prefer to execute independently with the strategy and frameworks Bill helped create. There's no forced long-term commitment; ongoing support is available if and when it adds value to your execution efforts.

Bill's approach builds in adaptability from the start. Rather than creating rigid plans, you'll develop decision-making frameworks that help you recognize when to stay the course and when to pivot. If you engage ongoing strategic support, quarterly check-ins provide structured opportunities to assess whether your strategy still fits your reality. Many organizations also schedule annual strategy refresh sessions—shorter facilitated discussions to update goals, reallocate resources, or address new strategic challenges without starting from scratch.

You're ready if: (1) Your leadership team recognizes the need for clearer strategic direction. (2) Leaders are willing to engage in honest dialogue about challenges and make difficult decisions. (3) You have realistic expectations—strategy development clarifies direction but doesn't eliminate uncertainty. (4) You're committed to turning strategy into action, not just creating a document. If you're unsure about readiness, an initial conversation with Bill can help assess whether now is the right time or if other groundwork would be beneficial first.

Schedule an initial conversation. This is a straightforward discussion where Bill learns about your strategic challenges, you ask questions about the approach, and you both assess whether there's a good fit. There's no pressure, no sales pitch—just an honest conversation about whether Bill's strategic facilitation can help address what you're facing. If it makes sense to move forward, The Persimmon Group will provide a tailored proposal outlining scope, timeline, and investment. If it's not the right fit, Bill will tell you that too.