EP537: Teresa Gregory - Check Your Bias: How Mindset Shifts Help Bookkeepers Lead Better

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Teresa Gregory has spent her career helping leaders find the hidden patterns that quietly shape every decision they make. In this conversation with host Michael Palmer, she turns that lens directly on bookkeeping professionals — the people who sit in a unique seat of trust with their clients every single day. Whether you manage a team, serve a full client roster, or are building your firm on your own, the mindset habits Teresa shares here apply immediately.

Chapters

• [00:00] Introduction and Teresa's Background
• [03:13] Hidden Bias and First Impressions
• [07:00] Bias as a Biological Response
• [11:00] Working With Difficult Clients
• [14:30] The PAUSE Method Explained
• [19:00] Active Listening vs. Reloading
• [23:00] Strategic Client Check-Ins
• [27:00] Why Every Bookkeeper Needs a Coach
• [31:30] Positioning Yourself as an ROI Expert
• [35:30] Teresa's Resources and Wrap-Up

Hidden Bias Is Running in the Background

Every interaction you walk into carries invisible baggage. Teresa calls it the fight-or-flight response — a biological pattern your brain uses to assess safety and make quick judgments. The problem isn't that it exists; the problem is when you let a past experience cloud what's happening right now. "I'm reinforcing every time I have this engagement with them without identifying it and without saying, 'hey, this is what's going on,'" she explains. The first step is simply naming the bias before you walk into a meeting, a call, or a difficult conversation.

The PAUSE Method for Breaking the Pattern

Teresa teaches a five-step framework — Pause, Awareness, Unwind, Strategic, Effectiveness — that gives leaders a repeatable way to interrupt bias before it takes over. Pause and name what you're carrying. Build awareness of when it tends to show up. Unwind the reinforced pattern. Be strategic about what you'll do differently. Then evaluate honestly: did it work? "You have to identify it and say, 'this is what's causing me to do this,' and then look at how do I overcome it?" The method works whether you're prepping for a tense client review or walking into a room full of people you're slightly in awe of.

Active Listening vs. Reloading

Most people think they're listening. Teresa says they're reloading — nodding, making eye contact, and waiting for their turn to talk. Active listening looks different: you take in what the client actually said, reframe it back in your own words, and confirm you got it right. "What I heard you saying is…" followed by "Did I get that right?" This one shift builds more trust than almost anything else you can do. For bookkeepers — who already have deep, consistent access to business owners — it's a fast path to becoming a true strategic partner rather than a transactional vendor.

Know What Your Client Actually Cares About

Teresa is direct: you should have a running list of each client's core values and priorities. "If I cannot say to Michael, your number one important thing is ROI or bottom line or taxes, I need to be able to identify that. You should have a running list of what are the things that are important to that client so you can speak to those — and then any solution that you're proposing or any conversation you're having ties right back to it." Schedule intentional check-ins — monthly if possible, quarterly at minimum — to ask what has changed. Businesses change. Lives change. If you're not asking, you're missing it.

Reposition Yourself as an ROI Expert

One of the most practical moments in this episode is Teresa's challenge to bookkeepers to rethink how they introduce themselves. "If you were to tell me, 'I offer business owners a strategic advantage because I help them understand ROI' — now I'm like, whoa, I need that." Her own sister, a bookkeeper, spent six months practicing a new way of describing her work at local chamber events. The result: new clients in industries she'd never considered. You track every dollar that moves through a business. That is, by definition, the work of an ROI expert. Lead with that.

Links mentioned

• Squared Success website: squaredsuccess.com
• Teresa Gregory on LinkedIn: search "Teresa L. Gregory"
• PureBookkeeping: purebookkeeping.com
• The Successful Bookkeeper: thesuccessfulbookkeeper.com

About the guest

Teresa Gregory is the founder of Squared Success, a leadership strategy and coaching firm. She began her career in training and development inside corporate organizations — including supporting the finance team at Microsoft — before transitioning into executive coaching for business owners. Her work focuses on helping leaders uncover hidden mindset barriers, break bias patterns, and build the intentional habits that drive real results. Teresa is also a speaker and, notably, coaches her own bookkeeper sister to help her grow her firm.

About the host

Michael Palmer

Michael Palmer is the host of The Successful Bookkeeper podcast and co-founder of Pure Bookkeeping and The Successful Bookkeeper. He started this work because of his father — a brilliant electrical contractor who worked twice as hard as he should have had to, because nobody on the financial side was in his corner. That gap is what The Successful Bookkeeper exists to close. His view: bookkeepers are the most undervalued force in small business — and every bookkeeper who builds a real business changes two families: theirs, and their clients'.