Brandon Moddes MSP Strategic Planning Review | Fox & Crow Group
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Brandon Moddes Fox & Crow Group Strategic Planning Review: Right Fit, Clear in the First 15 Minutes
Thank you to Brandon Moddes for this review of his MSP strategic planning experience with Ian Richardson, Co-Founder of Fox & Crow Group.
First Published: October 1, 2025
Last Updated: May 1, 2026
In strategic planning engagements, fit matters as much as capability. The right facilitator can challenge a leadership team productively, build trust quickly, and shape a planning process that reflects what the business actually needs. The wrong one makes the room cautious and produces a plan that no one is fully committed to.
Knowing whether you have found the right fit — before committing to a full engagement — is a significant decision for any MSP owner or leadership team.
This Brandon Moddes Fox & Crow Group strategic planning review describes how quickly that clarity arrived.
"Ian brings his unique perspectives and skills to create a meaningful and purpose-driven experience for the business strategic planning process. From the first fifteen minutes of working with Ian, it was clear that he was the right fit for us."
What Makes Strategic Planning "Meaningful and Purpose-Driven"
Moddes describes the strategic planning experience as "meaningful and purpose-driven" — a pairing that reflects two qualities that are both necessary and often missing.
Meaningful planning connects to what the business actually cares about. Not generic goals that could apply to any company, but specific objectives that reflect the real priorities of this leadership team, at this moment in the business's development. A planning process that produces generic output — grow revenue, improve retention, hire better — has not done the hard work of helping the team understand what those things mean for them specifically.
Purpose-driven planning keeps every part of the process connected to why it matters. Strategic planning sessions can easily become disconnected exercises in categorization and prioritization that leave participants feeling like they went through a process without arriving anywhere meaningful. A purpose-driven facilitator keeps the thread visible — reminding the team why each question matters and how each answer will shape their ability to move forward.
Ian Richardson brings both qualities to the planning room, shaped by years of working with MSP leadership teams and by having operated an MSP himself.
Right Fit — Known in 15 Minutes
The immediacy of Moddes' confidence — "from the first fifteen minutes" — points to something that experienced facilitators develop over time: the ability to establish trust and credibility quickly without performing it.
That rapid establishment of fit happens through:
Relevant context. Ian Richardson's MSP operational background means he can reference real experiences that resonate immediately with MSP leadership teams. He is not translating general business advice into an IT channel context — he is speaking from inside it.
Sharp initial questions. The questions a facilitator asks in the first fifteen minutes of a planning engagement signal whether they are working from a script or genuinely trying to understand the specific business. Questions that reveal real curiosity about this team's specific situation build confidence fast.
Honest directness. Fox & Crow Group's approach to strategic planning includes willingness to surface uncomfortable truths about what is and is not working. That directness — delivered constructively — creates the kind of safety that makes meaningful planning possible.
The Unique Perspectives That Drive Better Planning
Moddes specifically notes that Ian brings "unique perspectives and skills" to the planning process. In the context of MSP strategic planning, those perspectives come from a combination of sources:
- Direct MSP operational experience, including the pressures of service delivery, client management, and team leadership
- Exposure to dozens of MSP leadership teams at different stages of growth
- Deep familiarity with IT channel dynamics — how vendor relationships, partner programs, and market trends shape what individual MSPs can and should pursue
- Structured strategic planning methodology that provides a disciplined framework for the conversations
That combination produces perspectives that are both practically grounded and strategically informed — rare in an advisor who is not simply applying a generic consulting playbook.
Explore MSP strategic planning facilitation with Fox & Crow Group.
See more Fox & Crow Group client testimonials and case studies.
Book a call to discuss strategic planning for your MSP leadership team.
FAQ: MSP Strategic Planning Facilitation with Fox & Crow Group
What should I look for in an MSP strategic planning facilitator?
Look for someone with direct MSP operational experience, a track record of working with leadership teams at your stage of growth, and the ability to challenge assumptions productively while keeping the team aligned and moving forward.
How quickly can I tell whether a strategic planning facilitator is the right fit?
In most cases, the fit becomes clear in the first session. The quality of the initial questions, the facilitator's familiarity with your environment, and their ability to establish credibility with the team are all visible early.
What makes Fox & Crow Group's strategic planning approach different?
Fox & Crow Group combines Ian Richardson's direct MSP operational experience with structured planning methodology — producing planning conversations that are grounded in how MSPs actually work, not just how they are supposed to work in theory.
How do I evaluate whether my MSP is ready for strategic planning facilitation?
If your leadership team is making decisions reactively, struggling to agree on priorities, or executing tactically without a clear long-term direction, strategic planning facilitation is likely to produce significant value. Contact Fox & Crow Group to discuss your current situation.
The StratOp facilitation experience varies by team structure and business stage. Kathy Blair's review covers how Ian Richardson handled her leadership team planning sessions, and Reuben Levinsohn's account addresses the partner alignment problems that strategic planning tends to surface. Both are worth reading alongside this one if you are considering a StratOp engagement.
The clarity that arrives quickly in a Fox & Crow engagement — knowing within fifteen minutes you have the right fit — is what makes the full MSP sales system worth examining before committing to it, and how that same directness shows up across two years of compounding results is the clearest evidence of what the right partnership produces.