And How I Quote With Confidence

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When the Leads Finally Came In

When I received two form submissions in the same week from people interested in my bookkeeping services, I remember feeling a mix of excitement and panic. For months, I had been building toward this moment. I had the website, I had the branding, I had the systems I thought I needed. But when it came time to actually get on a call and figure out what to ask and how to quote, I felt completely unprepared.

I knew I could do the bookkeeping. That part never worried me. What I didn’t have yet was a clear process for running the conversation. What information did I need? How detailed should I get? How do I make sure I’m not underpricing? Those were the questions that were running through my head.

Looking back, the problem wasn’t skill. It was structure.

Why Discovery Calls Feel Overwhelming at First

My first two discovery calls were far from perfect. One was a bakery startup run by two sisters who had been operating out of their home and were preparing to open a storefront. The other was a massage therapist buying the business she had been working for. Both were new entrepreneurs and neither had worked with a bookkeeper before.

In hindsight, I wasn’t asking the right questions. But they also didn’t know what I should have been asking. We were all figuring it out together. It worked out, but I wouldn’t call it efficient or scalable.

That experience forced me to step back and create a more intentional framework. I didn’t want pricing to depend on how confident I felt that day. I wanted it to depend on data.

Your Website Should Do Some of the Work First

One thing I’ve learned is that the discovery call should not be the first time someone understands what you do. Your website should already be filtering and framing the conversation.

I use Squarespace to structure my service pages and intake forms so that by the time someone books a call, I already know what type of business they run, roughly where they are in revenue, and what they think they need help with. It’s not about having a flashy website. It’s about clarity. Clear services. Clear expectations. Clear next steps.

When someone comes into a call already understanding your positioning, the conversation immediately feels more productive.

What I Actually Ask on the Call

Now, my discovery calls follow a consistent flow. I start broad and then narrow down.

First, I ask about the business itself. What industry are they in? How long have they been operating? What is their legal structure? Roughly where is revenue sitting? Revenue gives context, but I no longer use it as my main pricing factor.

Then I move into infrastructure. What software are they using? Are the books reconciled? Who has been handling the bookkeeping? How often are they reviewing financials? This tells me whether I’m walking into steady maintenance or a cleanup situation.

From there, I focus heavily on complexity. How many bank accounts and credit cards are we dealing with? Are there multiple merchant processors? POS systems? Payroll? Loans? Inventory? Multiple revenue streams? These details matter far more than just total revenue.

I once had a mid-six-figure client whose books took maybe thirty minutes a month because everything was simple and clean. On the other hand, I’ve had lower-revenue businesses that required significantly more time because of transaction volume and lack of structure. That’s when I realized revenue-based pricing alone doesn’t work.

Complexity drives workload. Workload drives pricing.

The Exact Question List I Use

Eventually, I turned my discovery process into a standardized question list that I use with every single lead. It keeps me from forgetting key details and helps me evaluate everyone through the same lens. That consistency alone has improved my pricing accuracy more than anything else.

If you’d like the exact discovery questions I use inside my firm, you can enter your email below

The Documents I Require Before Sending a Proposal

This is probably the biggest change I made.

I no longer quote based on conversation alone. During the call, I let them know that to give an accurate proposal, I’ll need three months of bank statements and three months of merchant statements or invoices, depending on the business. I explain that this helps me understand transaction volume and get a realistic picture of what I’m stepping into.

Before reviewing anything, I send over a Non-Disclosure and Confidentiality Agreement. It’s a small step, but it builds trust immediately. Most clients aren’t expecting it, and I’ve found that it reinforces professionalism.

All of this is managed through Google Workspace. I create a Drive folder for each lead, send the NDA for signature, host the call through Google Meet, and keep notes and follow-up communication in the same ecosystem. I like having one system that covers email, meetings, file storage, and document sharing instead of juggling multiple platforms.

It keeps things simple on my end and clear for the client.

Get What You Can While They’re Engaged

If I could give one practical tip, it’s this: try to get as much done as possible while the client is actively engaged. Bookkeeping almost always falls to the bottom of an entrepreneur’s to-do list. That includes sending us the documents we need.

When I explain the required documents clearly on the call and immediately send the upload instructions through Google Workspace, I see far fewer delays. Structure reduces friction.

Red Flags I Pay Attention To

Over time, certain patterns become easier to spot. If someone can’t produce basic documentation, immediately blames every prior bookkeeper, starts requesting discounts, or starts inquiring on items that are typically out of scope and not in the normal bookkeeping tasks, I slow down. That doesn’t automatically mean I won’t work with them, but it does mean I look closer at scope and expectations. For instance, I had one lead who wanted me to keep track of customers of who has and hasn’t paid, but without monthly bookkeeping and no systems in place for me to record keep. So essentially I would be doing bookkeeping outside of QuickBooks and I wasn’t interested in that.

Not every lead needs to become a client. Sometimes the most professional move is saying no.

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Why This Process Changed Everything

Marketing brings people to you. But your discovery process determines whether your firm grows in a healthy way. When pricing is based on structure instead of instinct, everything feels steadier. Conversations feel calmer. Proposals feel more confident.

Discovery calls aren’t just introductory chats. They’re the first real system inside your bookkeeping firm. When you treat them that way, your entire client experience improves.

In the next post, I’ll walk through how I actually turn discovery call information into a clear and defensible pricing structure.

Resources mentioned in this post

Google Workspace – professional email, file storage, and client collaboration. Get 10% off your first year!
Squarespace Websites – as a Squarespace Circle Silver Member, I can pass along savings

How I Run My Bookkeeping Discovery Calls