Jack Choppin, Challenge Your Clients

Challenging clients is one of the fastest ways for bookkeepers to move from being seen as a helpful service provider to being trusted as a real adviser. This is exactly what we discussed with Jack Choppin from GoProposal by Sage, who told us that meaningful progress in a client’s business usually requires a change in thinking and behaviour, not just accurate bookkeeping.

In practice, this means being willing to challenge habits that keep clients stuck. Avoiding fee conversations. Letting late payment slide. Treating pricing as something to deal with later. These behaviours feel easier in the moment, but they undermine both the client’s business and the bookkeeper’s practice.

In our Leadership Takeover series, Jack Choppin explained that client success is not about being liked or showing someone where to click. It’s about helping them get ready to do the scary, business critical thing they’ve been avoiding.

This matters because bookkeeping often rewards niceness, speed, and accuracy. Clients expect a tidy VAT return. But they don’t build stronger businesses from compliance alone. We’ve spent years at The 6 Figure Bookkeeper helping bookkeepers step into advisory style conversations that lead to better outcomes for clients and healthier, more profitable practices. It’s exactly the topic we went into with Jack Choppin.

This article contains paid promotion for our partner, GoProposal by Sage.

What “challenging your clients” actually means in bookkeeping

Challenging clients means helping them face what’s really happening in their business and guiding them toward the next best action, even when it feels uncomfortable.

Your client might think they need a one off fix, whereas you know there’s a process needed. Alternatively, you might have to challenge yourself to change your pricing or otherwise you’ll always be stuck when it comes to capacity. These challenges aren’t always easy to face, for you or your client. We have to learn to think of them as choosing long term success over short term comfort.

Why bookkeepers default to being “nice”, and why it holds clients back

Many bookkeepers were taught that being professional means being polite, compliant, and easy to work with. Jack Choppin highlights a common misunderstanding here. Early account management often feels like being friendly and responsive, but true client success requires pushing for the outcome the client actually needs.

A familiar example came up in the interview. A client hasn’t paid for three months, but the work continues anyway. The nice approach avoids conflict and hopes it resolves itself. The advisory approach challenges the reality of what’s happening, unpaid work, blurred boundaries, and growing resentment.

Being nice keeps the peace. Challenging creates processes and a system you can change.

Why pricing is often the first thing that needs to be challenged

Pricing is one of the easiest topics for both clients and bookkeepers to postpone. Jack Choppin of GoProposal by Sage describes pricing as something people convince themselves “isn’t business critical”, because it feels like something you can always deal with later.

This, however, is a trap.

Pricing affects day to day reality now. It shapes capacity, energy, confidence, and whether a practice can grow sustainably. For bookkeepers, challenging clients on pricing can look like:

• reviewing fees regularly instead of setting and forgetting
• setting clear scope boundaries, what’s included and what’s extra
• linking price to outcome and responsibility, not hours and effort

Often, the challenge has to start internally. When bookkeepers learn to challenge clients, they also have to challenge their own beliefs about what they’re allowed to charge and how direct they’re permitted to be.

Client success isn’t software onboarding

One of the most useful distinctions Jack makes is between teaching the tool and delivering real success. Many teams stop at the false finish line. The client knows where to click. The report runs. Job done.

Jack argues that real success asks a different question. Is the client ready to have the real conversation they’ve been avoiding? For bookkeepers, we need to change the goalposts of what we think “success” means.

It’s not success because a report was delivered. It’s success when the client uses it to raise prices, fix late invoicing, stop leaking cash, or make a more strategically informed decision.

That’s the difference between activity and impact.

How to make challenge land better

The interview also explored why GoProposal invested so heavily in high touch experiences early on, like fast personalisation and the well known “shock and awe” packs.

Jack explains that trust and credibility were built into the experience from day one. When people felt supported and taken seriously, they were far more open to being challenged later.

The numbers backed it up. Training was offered to every free trial. Around half took it. Of those, the vast majority converted.

For bookkeepers, here’s the lesson we can learn. Challenge works best when the client experience feels safe and supportive. Clear onboarding, consistent processes, and good communication create the conditions for honest conversations.

How to challenge clients without damaging the relationship

Challenging clients works when it’s framed around partnership and progress. Jack describes success as lowering the barrier to the big, scary thing and helping the client try it.

In practice, this can look like:

Using evidence: “You’ve been unpaid for 90 days, that’s now a risk.”
Naming the cost of avoidance: “If pricing stays the same, capacity stays capped.”
Offering a next step: “Here are two scripts, choose one.”
Having standards: “Work pauses if payment is overdue beyond X days.”

This is where bookkeepers become the calm, commercial voice many clients don’t have.

Jack Choppin Interview FAQs

Who is Jack Choppin?

Jack Choppin is a customer success leader at GoProposal by Sage. He was the first team member at GoProposal and played a key role in helping accountancy and bookkeeping firms adopt better pricing conversations, clearer scope, and more confident client communication. His work focuses on client success, behaviour change, and helping professionals do the uncomfortable but business critical things they tend to avoid.

What is GoProposal by Sage?

GoProposal by Sage is a pricing and proposal software designed specifically for accountants and bookkeepers. It helps firms price services consistently, present fees clearly, and move away from undercharging and scope creep. The platform supports advisory style conversations by linking price to value and outcomes, rather than hours or guesswork.

How do bookkeepers challenge clients without sounding rude?

By anchoring the conversation in facts, outcomes, and agreed standards, then offering a clear next step. It often sounds like, “Here’s what the numbers show, here’s why it matters now, and here’s what we need to do next.”

What should a bookkeeper challenge first?

Start with the behaviour causing the biggest recurring problem. For most bookkeepers, that’s late payment, late information, or unclear scope. Fixing one of these usually reduces stress and improves profitability quickly.

Why is being “nice” a problem in bookkeeping?

Niceness becomes a problem when it replaces honest advice and accountability. Clients might feel comfortable, but nothing improves. Speed and accuracy are expected, real value comes from addressing the uncomfortable issues.

Does challenging clients improve retention?

Yes, when it’s done with support and structure. Clients stay when they feel they are making progress because of this service relationship.

Challenging clients can feel uncomfortable at first, especially if you’ve built your identity around being helpful and easy to work with. But as Jack Choppin’s interview reinforces, clients don’t just need friendliness. They need leadership, accountability, and someone who will guide them through the hard conversations.

Watch the full interview with Jack Choppin on our YouTube Channel.