From Selling Golf Balls to Coaching 400+ Firms with Will Hill

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Will Hill spent 21 years at Thomson Reuters helping build the accounting industry's shift toward advisory services, then left to found Will Hill Consults, LLC, where he coaches CPA firm owners one-on-one at the intersection of people and process. With 25+ years in the industry and hands-on work inside 400+ accounting firms, Will has visited more firm offices than almost anyone in the space, but keeps his own active client roster small on purpose. On this episode of Scrappy But Successful, Jack sits down with Will to talk about why he refuses to coach in groups, the moment he had to reassure two employees their jobs weren't going away, and how firms make the leap from compliance to advisory conversations.

Selling Golf Balls in Flint and Landing at Thomson Reuters

Will grew up in Flint, Michigan, with no entrepreneurs in the family, but an early itch to make money on his own terms. Summers at his grandmother's cabin near a golf course turned into a small hustle: wading into the weeds to find lost balls, washing them off, and selling them out of the front yard, with the proceeds going straight into baseball cards rather than savings. After a run of high school and college jobs, including three summers as a floating bank teller, he landed in product support at what would become Thomson Reuters one week after graduation and spent the next 21 years there, eventually helping launch the Practice Forward program that pushed accounting firms toward advisory services.

Why He Coaches CPA Firm Owners One-on-One, Never in Groups

Ask Will what makes his coaching different and he'll point to one rule: no group sessions, ever. Every engagement is one-on-one, built around specific people at a specific firm, down to naming individual staff members and clients when they map out work plans together. He traces the approach back to why he started the business in the first place: he wanted to know he was helping people directly, not running a program at the expense of that connection. He has experimented with group formats over the years, but keeps returning to one-on-one work as the niche where he can see his impact clearly.

Telling Two Employees Their Jobs Weren't Going Away

One of Will's most memorable moments from his Thomson Reuters years came during the rollout of a new paperless audit package. A partner pulled him aside and asked him, then a 28-year-old software trainer, to reassure two administrative staff members that the new tool wouldn't cost them their jobs. Will leaned on the same approach he used in every client conversation: their value was never the tool itself, it was understanding the client and communicating well, skills that carry over no matter what software comes next.

Moving Firms From Compliance to Client Advisory Services

Will helped build the Practice Forward program at Thomson Reuters, which pushed firms to move from compliance-only client relationships toward advisory ones, back when the industry still needed the term explained. His framework for that conversation is to let the rope out from concrete numbers to abstract goals and back again: ask about a client's hopes and motivations before circling back to the numbers, since the more understood a client feels, the better the concrete recommendations land. He argues the accounting profession is uniquely positioned for this work, since it already ties daily actions directly to measurable results.

Connect with Will:

• Website: https://willhillconsults.com/

• LinkedIn: https://www.linkedin.com/in/wghill/

Connect with Jack:

• LinkedIn: https://www.linkedin.com/in/jack-tompkins/

• Consulting: https://www.pineapplecf.com

• AI Analyst Product: https://www.pineappleanalyst.ai/

• YouTube: https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng

About Pineapple:

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• Fractional Analyst Services: https://pineapplecf.com/fractional-analyst

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• QuickBooks Online Dashboard: https://pineapplecf.com/quickbooks-online-performance-dashboard

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• Business Coaching Practice Dashboards: https://pineapplecf.com/business-coaching-dashboards