EP539: Debra Angilletta - Numbers Only Tell Half The Story: Ask Better Questions To Sell Advisory

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, pick five people who seem most open to a deeper conversation, and book a 30-minute call — framed simply as "I saw some interesting things in your books that might be of value." That's it. The goal isn't to pitch advisory on the spot; it's to practice having the conversation. "There's nothing complicated here," Debra says. "I don't want to make it complicated for your audience at all." Business Owners Are Waiting for You to Ask Debra interviewed 100 small business owners while writing her book Hidden Profits, and the finding stopped her in her tracks. When she asked what they wished their bookkeeper did that they weren't doing, the answer was overwhelming: more strategic advisory. "I wish they would give me information that I can use to drive my business forward." Most business owners operate in isolation, with no one to think out loud with — and your existing financial relationship puts you closer to that trusted-advisor seat than you might realize. The Transformation on the Other Side Bookkeepers who start having these conversations consistently go through a noticeable shift. Debra sees it regularly: once they experience what advisory conversations feel like, they want more of them. More importantly, the relationship with the client changes. "It actually uplevels you to partnership level... they're going to see you as that trusted advisor." The compliance work stays valuable — but it's no longer the ceiling on what the relationship can be. Links Mentioned Hidden Profits: Stop Chasing Cash, Predictable Profit in 90 Days by Debra Angilletta — findmyhiddenprofits.com (free download of first 3 chapters) or search "Hidden Profits" on Amazon MasterMySales.com — Debra's sales training for financial professionals PureBookkeeping.com — episode sponsor thesuccessfulbookkeeper.com — show resources and guest links About the Guest Debra Angilletta is a fractional CFO, course creator, and speaker at MasterMySales.com who specializes in helping bookkeepers, accountants, and fi