Many business owners do the hard work — attracting the lead, running the call, writing the proposal… and then freeze. Fi shows you why the follow-up is the sales process — and how to approach it with intention, empathy, structure, and self-respect.

In this episode of **Money Secrets**, Fi wraps up Part 4 of the four-part **From Maybe to Yes** series — and she’s tackling one of the most avoided (and emotionally loaded) parts of business: **following up your proposals**.

Listen to Episode 58

What You’ll Learn in This Episode

Why most proposals die (and it’s not because they don’t want you): Fi breaks down why clients often don’t respond — and how their silence usually has nothing to do with your worth, your offer, or your abilities. Timing, capacity, life admin, and decision fatigue are far more common than rejection.
Instead of spiralling after you hit send, Fi explains why you should have a pre-written, pre-thought-out follow-up sequence ready before emotions get involved. This is your most powerful sales asset — not an afterthought.
How to get clients talking about their goals, not just their problems: You'll learn how to uncover what clients really want, what’s currently not working for them, and how to reflect that back so they feel understood, seen, and supported.
How to follow up without being annoying: Fi walks through how to create thoughtful, varied follow-ups that add value — not irritation. You’ll learn how to avoid the “Hi, just checking in again?” emails and instead craft messages that genuinely move someone toward a decision.
How to keep the door open without creating shame: Fi explains how to craft follow-ups that make people feel welcome to reply at any time — even weeks or months later — instead of feeling embarrassed that they “left it too long.”
When (and how) to close the loop without burning the bridge: You’ll learn how to write a final follow-up that respectfully closes the proposal conversation while still keeping the relationship open for the future. Because sales is long-game relationship building — not just one yes/no moment.
How often to follow up (and when to stop): Fi shares realistic timelines for different price points, how many follow-ups most people need, and why your “yes” might come on the 4th… 7th… or even 12th email.
Why following up is an act of care, not clinginess: Fi reframes follow-up as service: clarity, support, reminders, and relationship — not harassment. When done well, it helps people make decisions that move them closer to their goals. Fi reframes follow-up as service – clarity, support, reminders, and relationship — not harassment. When done well, it helps people make decisions that move them closer to their goals.

How to Follow Up Your Proposals - From Maybe to Yes Series #4 (EP#58)

Money Secrets Podcast – Episode 58

Introduction

We've made a lot of progress as a society in many areas, but one thing that hasn’t changed enough is our relationship with money. If we want to tip the scales in favour of marginalised people, we need to understand the secrets to making money in small business.

The more we talk about money — especially the secrets that usually stay behind closed doors or on the golf course — the more empowered we become. My mission is to get more money into the hands of good people, specifically business owners like you.

Because I believe small business can change the world. And to do that, we need to be making more money.

Acknowledgement of Country

This episode was recorded on the lands of the Wurundjeri People of the Kulin Nation. I’d like to acknowledge them as the Traditional Owners and custodians of this land and water that I live, work and play on.

I pay my respects to Elders past and present, and recognise that sovereignty has never been ceded. This always was, and always will be, Aboriginal and Torres Strait Islander land.

Why Proposals So Often Go Quiet

You’ve done everything right.

You attracted the lead.
You ran a great discovery call.
You put real thought into the proposal.

And then… nothing.

No reply. No clarity. Just silence — and the familiar spiral of second-guessing, self-doubt, and embarrassment.

Fi is very clear on this: silence doesn’t mean rejection. More often than not, it means your lead is busy, unsure, distracted, or missing one key piece of information.

Which is why having a plan to follow up matters.

Follow-Up Is Not Badgering

One of the biggest misconceptions about follow-up is that it’s annoying or pushy. It doesn’t have to be.

Fi recommends:

Following up intentionally
Not sending more than one or two emails per week
Making sure every follow-up adds something new

The goal isn’t to chase — it’s to support a decision.

Pre-Plan Your Follow-Up (Before the Spiral)

The best time to write your follow-up emails is before you send the proposal — when you’re calm, confident, and grounded.

Not three weeks later, when you’re spiralling and wondering what you did wrong.

When you pre-write your follow-ups, you:

Avoid emotional reactions
Stay professional and generous
Keep the process moving with ease

What to Say When You Follow Up

Instead of sending the same “just checking in” email over and over, Fi suggests varying your follow-ups to address different needs.

Some examples include:

Clarification-based:
“Do you have any questions about the proposal I sent through?”
Conversation-based:
“Would you like to jump on a quick call to talk this through?”
Reassurance-based:
Sharing what past clients were worried about — and how it worked out.
Story or case-study based:
Showing what’s possible through real examples.
Human and relational:
A thoughtful message that reminds them you’re a real person who’s genuinely invested.

Always assume positive intent. Always give them a shame-free way back into the conversation.

Good Money Club

Are you a female or LGBTQIA+ business owner who wants to make more money and create meaningful change? My 6-month program, Good Money Club, is designed to help you do exactly that.

We work on your pricing, positioning, business model, and mindset — so you can build your bank account and your impact. Read more about Good Money Club.

Make It Easy for Them to Respond

A key principle Fi emphasises: never close the door emotionally.

Your follow-ups should never make someone feel bad, awkward, or embarrassed for not replying yet. Instead, keep the loop open and welcoming — even if weeks or months have passed.

And yes, it’s okay to eventually stop following up.

When you do, let them know kindly:

Thank them for the opportunity
Wish them well
Let them know you’ll check in again down the track

This keeps the relationship intact — and often leads to future work.

How Many Times Should You Follow Up?

Most people stop after one or two follow-ups.

But what if:

The 4th follow-up was the one that landed?
The 7th email addressed the real concern?
The 12th touchpoint arrived at exactly the right moment?

Depending on your sales cycle, Fi suggests following up anywhere from 3 to 12 times — always spaced thoughtfully, always adding value.

Final Thoughts

Following up isn’t about pressure.
It’s about professionalism.
It’s about respect — for yourself and your client.

When you treat follow-up as part of relationship-building (not a personal verdict on your worth), selling becomes calmer, kinder, and far more effective.

This episode wraps up the From Maybe to Yes series:

Attracting the right clients
Running confident discovery calls
Creating proposals that convert
Following up with clarity and self-respect

If this series resonated, Fi has created a workbook you can download for free — and if you want deeper support, Good Money Club is where these conversations continue every week.

You never know which follow-up will lead to a yes — but you’ll never find out if you don’t send it.

Outro

Thank you for listening to Money Secrets. If you loved this episode, please subscribe, share it with a friend, or leave a review. Your support helps us get these conversations into the hands of more good people who deserve to thrive in business.

We’ve come so far as a society in many ways, but money is one of the areas where progress hasn’t been enough. If we want to tip the scales in favour of marginalised people, it starts with understanding the secret: money in small business.

In this podcast, Money Secrets, host Fiona (Fi) Johnston—Chartered Accountant, small business advocate, and impact enthusiast—dives into the conversations we need to have about money. The secrets that once stayed behind closed doors (or on the golf course) are finally out in the open.

Fi’s mission? To get more money into the hands of good people, like you. She believes small businesses have the power to change the world, and the key to making a bigger impact is to make—and manage—more money.

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Thank you to everyone involved for bringing this podcast together. We are excited to hear from you with any questions, feedback or suggestions for future episodes that you might have. Send a Direct Message to @peach.business

If you are excited for what’s to come, please like this episode, follow the podcast and share it with your friends. We are thrilled you're here.

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