Driftless Leadership

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The Nonprofit Strategy Suite

A Trusted Outside Voice For Nonprofit Leaders

Nonprofit leaders carry a lot at once: mission, people, funding, boards, programs, and a community that depends on them. It is hard to find time and space to step back, see what is really going on, and decide what should come next.


Driftless Leadership’s™  Nonprofit Strategy Suite is built to give you that kind of space. I do the careful background work—reviewing your 990s, scanning your landscape, listening to your leaders—so that when we are together, we can focus on the human side of the work: understanding your reality, naming what is true, and identifying practical next steps that fit your organization.


These services are organized into three broad areas: quick check‑ups that offer a fast, focused snapshot; deeper assessments that surface patterns, risks, and opportunities; and strategic engagements that help you make and sequence the bigger decisions. Each is meant to be right‑sized, usable, and shaped around your mission and context rather than a generic template.


If something here sounds close to what you need—but not quite—we can treat it as a starting point and tailor it together so it fits where you and your organization are right now.


The Nonprofit Strategy Suite is organized into three levels so you can start with the amount of support that fits your current season and capacity.



Level I – Quick Check‑Ups

6-15 Hours (estimated)

Short, focused engagements that give you a fast read on one area of your organization and highlight a few practical next steps. These are designed for leaders who want a light diagnostic before committing to deeper work. Services include:


Form 990 Snapshot & Red-Flag Review

A focused review of your latest Form 990 to surface what story it tells, where red flags may exist, and how small changes can better reflect your work and impact.

Basic Governance & Compliance Check

A light-touch review of your board’s structure, roles, and basic practices to surface strengths, gaps, and a few quick wins that strengthen governance and reduce risk.

Mission, Website, and 990 Alignment Review

An alignment review of your mission, website, and Form 990 to ensure your public story is clear, consistent, and faithful to the work you actually do.

Board Role & Strategic Planning Readiness Scan

A targeted scan of how your board currently understands and plays its role, designed to gauge readiness for strategic planning and surface immediate improvements.

“Who’s Around You?” Local Landscape Snapshot

A concise scan of nearby or similar nonprofits to clarify your local landscape, highlight your unique niche, and point toward partnership or differentiation opportunities.



Level II – Deep‑Dive Assessments

15-40 Hours (estimated)

More in‑depth assessments that surface patterns, risks, and opportunities across culture, programs, fundraising, board effectiveness, or overall organizational health. These are for organizations ready to look beneath the surface and build a clearer 12–18 month path. Services include:


Culture & Climate Check – Leadership Interviews

A confidential interview-based assessment that surfaces how staff and leaders experience your culture, trust, communication, and decision-making in day-to-day reality.

Internal Mirror 990 Analysis

A multi-year Form 990 analysis that turns your filings into an internal learning tool, surfacing trends, risks, and alignment between your public story and actual strategy.

Program Portfolio Impact Lite Review

A high-level review of your full program mix to clarify what’s central, what may be drifting or duplicative, and where to focus for greater mission impact.

Organizational Check-Up Assessment

A cross-functional assessment that takes a baseline of your organizational health and produces a simple 12–18 month improvement roadmap.

Grants & Funders 990 Scan

A research-driven scan of foundation 990s and websites to identify high-potential funders, align your case for support, and sharpen your grants strategy.

Board Effectiveness Pulse Check

An anonymous board survey and brief interviews that give your board a candid, data-informed picture of its current effectiveness and practical steps to improve.



Level III – Strategic Engagements

40 or More Hours (estimated)

Larger, integrative projects that help you make and sequence the bigger decisions about structure, priorities, positioning, and leadership. These are for moments of transition, growth, or complexity when you need a thoughtful partner for multi‑year direction. Services include:


Leadership Structure & Span-of-Control Review

A structured review of your leadership structure and spans of control to reduce bottlenecks, clarify accountability, and better support your strategy and people.

Sector Competitive Positioning Analysis

A comparative analysis of your most relevant peers to clarify your current position in the field and identify opportunities to differentiate, partner, or refocus.

Strategy Lite – Priorities & Focus

A streamlined strategy process that clarifies 3–5 near-term priorities, associated outcomes, and alignment guidance without requiring a full-scale strategic plan.

Full Organizational Assessment & Multi-Year Roadmap

A comprehensive assessment of your organization’s health that leads to a sequenced 2–3 year roadmap and a short list of quick wins to build momentum.

Succession & Leadership Pipeline Planning

A structured look at your key-person risk and leadership bench, resulting in a practical succession and pipeline plan over the next 1–3 years.


How fees work

Having served on more than a dozen nonprofit boards, large and small, I understand both the financial constraints and the strategic pressures that can stand in the way of asking for help. I use a flexible fee structure that takes into account the size of the organization and the scope of the work, so that smaller nonprofits can access support at a lower rate while larger organizations pay closer to a full consulting rate. My goal is to make these services a practical, right-sized investment in your mission, not an added burden on an already tight budget.



Questions?

Email Randy

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