Episode
EP539: Debra Angilletta - Numbers Only Tell Half The Story: Ask Better Questions To Sell Advisory
- Published
- Jul 7, 2026
- Duration seconds
- 1497
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Summary
See what the team at The Successful Bookkeeper has on right now → Your clients' financials tell one story. What your clients think about their business tells another. In this episode, fractional CFO, course creator, and speaker Debra Angilletta returns to show how closing that gap — through simple, curiosity-driven conversations — is the most direct path to selling advisory services. No complicated sales process required. Chapters [00:00] Opening Quote and Intro [01:35] Meet Debra Angilletta [03:30] Why Bookkeepers Struggle to Sell Advisory [06:10] The "Curious" Question Technique [09:20] Staying Human in a Digital World [11:50] Finding Your First Five Clients [14:30] The Advisory Transformation [17:30] What 100 Business Owners Said [20:30] About the Book: Hidden Profits [22:40] Rapid Fire: Steps to Take Now The Missing Half of the Story Numbers give you the facts; your client's perspective gives you the context. Debra frames advisory as the natural result of putting those two pieces together: "When you put those two pieces of information together, that's where the magic happens, and that's where you can fill the gap." The good news is you already have one half. You just need to ask for the other. One Word That Changes Everything If you're not sure how to start a probing question without sounding nosy or accusatory, Debra has a single practical fix: lead with "curious." Saying "Curious — I noticed this in your books, can you tell me more?" removes any sense of blame, gives your client permission to explore rather than defend, and opens the conversation rather than closing it down. It's a small shift with a big effect on how clients respond. Finding Your First Five You don't need to overhaul your entire practice to get started. Debra's advice is to scan your client list…