Great finance storytelling starts long before the board meeting

We collected 15 real-world prompts that finance teams use today across FP&A, accounting, and ops to streamline routine tasks.

Steal these prompts to create headspace for better judgment, collaboration, and stories that power the decisions that matter.

Download the Finance AI Prompt Playbook to start telling better stories

Before we get into things this week…

In the week commencing March 2nd, I will be previewing the pilot episode of a new show I’ve been working on, cutting to the truth on the latest technology for finance teams. Yes, this means Secret CFO on video. If you are interested in attending a virtual private screening let me know by clicking here and I’ll be in touch with the invite.

Anyway… let’s get into this week’s playbook:

Stop what you are doing and watch this:

In 2 minutes, you will learn more about storytelling than any book could show you.

South Park creators Trey Parker and Matt Stone were invited to NYU to talk to film students about storytelling.

They explained that a typical South Park episode has five or six key beats, arranged into three acts. Beats are the crucial moments where the story moves.

They discovered something important:

If you can place the words “and then” between those beats… the story sucks.

But… if you can place the words “but” or “therefore”… you have a story.

I use this technique constantly, often quite literally (even in the previous sentence). Despite being taught at school never to start a sentence with “but,” I do it all the time.

Matt Stone shares the real gold at the end of that clip: great stories are about causality between beats. Said another way, everything happens for a reason. South Park episodes are not a sequence of one thing happening after another; it’s about cause and effect.

Most corporate storytelling gets this completely wrong. It’s packed with “and then.” Revenue went up. And then costs went up. And then margins fell. And then we launched an initiative. And now we need to… blah blah.

PowerPoint is the safest refuge there is for dreadful storytellers. There it sits on your desktop, winking at you seductively, its blank canvas reminding you how flexible and forgiving it can be.

That flexibility leads to all kinds of performative, lazy outputs. Some of it is well-intentioned; the desire to be comprehensive, to show all the work. Others not so much; designed to wallpaper over uncertainty, to confuse and distract from the fact that they don’t really know what’s going on.

The problem with that flexibility is that it pushes the hard work onto the audience. They’re left to decipher the real story themselves. And naturally, they all walk away with a slightly different version, rowing the boat in slightly different directions.

But that’s not what you need.

Whether it’s a room full of investors on an IPO roadshow, a company all-hands, or a team offsite to drive transformation, you don’t want multiple interpretations.

You want them to leave with one story.

Your story.

In week one, we broke down the essence of a story and why finance is the worst place to learn how to tell one.

Last week, we explored (with help from the WWE) why great storytelling operates across multiple timelines and perspectives and how to build narrative arcs that hold together under pressure.

This week, we go deeper.

Because knowing what a story is isn’t enough, you need to know how to structure one. So this week, we are going to focus on those highest-stakes storytelling moments for CFOs. You know the kind:

What we cover here applies everywhere. But by focusing on the highest-stakes moments, we can extract the clearest lessons. And when I say high stakes, I don’t just mean for the company.

I mean for you.

In these moments, you are on display. Being judged by the people who matter most.

The difference between a 5 out of 10 performance and a 7 out of 10 performance can be enormous. It can be the difference between getting promoted and not. Between the PE fund backing you… or replacing you.

Don’t kid yourself. These moments might represent 1% of your work, but they often form 100% of the impression your stakeholder has of you.

They can’t judge the work they never see. That’s why this skill matters so much.

Of course, some people take this too far. Becoming great at presenting the work of others without understanding it themselves. Don’t be that person either.

But frankly, if you’re playing the game… brilliant work presented in a mediocre way will always lose to mediocre work presented brilliantly.

In the first part of this series, we established that every real story has transformation at its heart.

High-stakes CFO storytelling is just that idea stripped to its essentials:

Defining Point B is easy. It’s the thing you want:

CFOs are very good at defining Point B.

Where storytelling usually falls apart is defining Point A and, therefore, building the right journey between the two.

Why?

It’s the “E” word… Empathy.

It’s become a bit of a business/leadership cliché. The kind of word that gets thrown around on LinkedIn alongside photos of people staring thoughtfully out of windows.

But this is where it actually matters. Because you cannot move people unless you first meet them where they are now.

And that takes discipline. It means listening properly. Not waiting for your turn to talk. It means noticing the little things. What they don’t say. What they ask twice. Thinking about the why behind the question they actually ask.

It takes time and effort to hear the substance of a concern.

The best boardroom operators I’ve worked with have extraordinary empathy. And not in a soft, sentimental way. In a sharp, precise way. They know exactly how their audience sees the world and how far they need to move them.

Scott Galloway talks about this, too. The most successful leaders accumulate leverage over time: networks, influence, backing, capital. But that only happens when people want you to win.

And people only want you to win when they feel understood.

Which makes defining Point A much harder than it looks. 

And once you are clear on the journey you need to take your audience on, your job is to get them there in the simplest way possible.

This all assumes a nice, uniform audience. One shared view of reality. One shared ask.

In the real world, people walk into the room with different beliefs, different incentives, and different decisions to make. And being precise about those differences is crucial, because it doesn’t just shape the story you tell… it also determines the tactics you use to deploy it.

Time for a 2×2 😎

On the horizontal axis is how aligned your audience is on current reality:

On the vertical axis is how uniform your ask is:

Now, let’s take each quadrant one by one.

Bottom left: single view of reality → single ask

This is, in theory, the simplest case. Everyone agrees on what’s happening, and you need the same thing from everyone.

But don’t confuse simple structure with easy execution. There may still be a long journey between what they believe today and where you need them to land.

A good example is briefing a department on a specific (but contentious) ask.

Say you’re the CFO, and you are briefing the whole sales function to improve payment terms by five days on average by year-end. They’ll understand why it matters, but they won’t love it. It makes deals harder. It adds friction.

In this situation, the tactic is simple, even if the storytelling isn’t. You hammer the message in a very simple and clear way. Leave them with no doubt about what needs to happen and why. More on how to make a message simple coming up.

Bottom right: multiple views of reality → single ask

This is where things get more political.

You need the same decision from everyone, but they are starting from different places. The story that convinces one person won’t convince another.

The classic example is a board meeting.

You’re asking for approval on a major investment. One director loves it. Another is skeptical about execution risk. A third agrees with the strategy but worries about timing. They all need to vote the same way, but they don’t all need to hear the same story to get there.

This is why pre-alignment exists. Early in my career, I thought board pre-meetings were nonsense… performative theater. Why have the meeting before the meeting? In fact, I told of my first bizarre experience of this in a post a couple of years ago.

But opportunities to reframe and align people do make those meetings more efficient and the storytelling simpler for you and them.

Top left: single view of reality → multiple asks

Here, the room agrees on what’s happening, but you need different things from different people.

Investor relations is full of this dynamic.

Take a public earnings call. Your equity investors, lenders, suppliers, and credit insurers might all be listening. They hear the same words, but they each have a different role in your future.

That big investment you just announced might be a compelling growth story for equity investors. But a trade credit insurer hears increased risk. A lender hears increased leverage. A supplier hears counterparty stability or a change in strategy that could affect them.

Each audience needs to take a different journey from the same starting point.

So you don’t try to complete those journeys in the big room.

The public forum establishes the shared narrative. The specific asks happen afterward, in smaller rooms, in private conversations, where you can finish the story in the right frame for that stakeholder.

Top right: multiple views of reality → multiple asks

This is where storytelling gets very complex.

You have different people believing different things, AND you need different things from each of them.

A company-wide all-hands is a good example. Employees, managers, senior leaders, and functional teams are all in the same room, but their starting points and required actions differ dramatically.

You have two ways through this:

This example is especially true in fundraising, especially from the capital markets.

When you’re raising a major debt or equity package, you’ll typically run a formal roadshow. That’s the big storytelling moment. The public narrative. The headline story.

But the roadshow alone doesn’t close the deal.

Behind it sits a dense schedule of private meetings. One-on-ones with key institutions. Smaller group sessions. Follow-ups. Each investor has a distinct starting point. Divergent concerns. Different influence. And ultimately, a different role in getting the deal done.

Once you understand the tactics and the type of audience you are working with, you can start to build out the story.

This phrase was popularized by Steve Jobs. I once worked for a CEO who adopted it with religious intensity. He’d deploy it whenever someone couldn’t explain something in elementary-grade language.

For a while, he even kept an actual stick on his desk.

I never got hit with it. But it did get pointed at me a few times.

It drilled into me, early in my career, the importance of using plain, elementary language in any situation. No matter how complicated the underlying reality.

This became a real superpower. Especially in the boardroom.

I’ve led discussions involving complex capital structures, covenant mechanics, and operational issues with messy, non-linear financial consequences. The kind of topics that investor directors, audit chairs, and former CFOs can follow. But which can lose directors from non-finance backgrounds within seconds.

My ability to break those issues down into first principles helped bring those directors into the conversation. They stopped being passengers and became participants, and they appreciated it deeply. Done consistently, that builds trust… and that compounds over time.

And in a big diverse board, that compounding trust can become an order of magnitude shift in your influence in the boardroom.

But being simple to listen to on technical matters is hard.

It’s easy to intellectually posture and talk loudly while saying nothing at all. Some CFOs do this deliberately. Even more do it without realizing.

It’s just as easy to be so reductive and simplistic that you lose the meaning and fidelity of the issue.

So being truly simple is not… well… simple.

Earlier, I bemoaned the flexibility of PowerPoint. If your storytelling starts (as many do) with Untitled.ppt, you’ve already lost.

The story you need - the one that actually drives action - is probably already inside you. But it’s buried, not just waiting to be burped out into a 50-slide deck.

PowerPoint thinking is everywhere. The big consulting firms are the masters. Logical, comprehensive, exhaustive. And tedious. Read this Reddit post to see how they think.

I’ve sat through more MBB decks than I care to remember. They’re always impressive. And almost always too long. Fifty slides. Sometimes hundreds. Occasionally split into multiple “volumes,” like a Victorian novel.

They work as a record of analysis. But as a device to inspire decisive action? Much less so.

But at least they execute this style well; most of our (in finance) decks are dollar store versions of this style. 

So, how to do it, differently?

.doc is your friend. Sketch the story in writing. Word, Google Docs, handwritten, it doesn’t matter.

Writing imposes constraint. You have to put one word after another, and you can’t hide behind formatting or charts. It forces you to confront the logic and journey from Point A to Point B directly. Is it compelling? Is it logical? Is it simple?

To do this, I like to build out a bullet point sketch. Five or so key narrative beats. The spine of the story. It might look like this:

Now, I’m not saying narrative wizardry can convince lenders to extend credit you don’t deserve. Finance doesn’t work like that.

But structure changes framing. And framing changes engagement.

It won’t turn bad credit into good credit. But it might turn a reflex “no” into a considered “let’s look at this properly.”

In this example, I used the ‘But’/’Therefore’ structure from South Park we started with. But it’s not the only structure.

Once you have the story structure, turning it into presentation materials becomes much easier. But don’t leap straight into PowerPoint. Sometimes the right form is a memo. I’ve often found that works best with boards.

Other times, visual aids or detailed financials are essential, especially with external stakeholders. Just make sure they serve the story, not overwhelm it. You can always include a full financial pack as an appendix or handout so you don’t lose the narrative thread.

The art is to keep it simple and use assets that do real work. If you’re pitching CapEx to refurbish a dilapidated building, nothing beats a photo of peeling paint, a 1980s kitchen, or water pouring through a hole in the roof.

It’s about choosing the right devices to make the story undeniable.

The highest-stakes storytelling moments define the ceiling of your CFO career.

But it requires discipline. Discipline in knowing exactly who you’re talking to. Discipline in showing them a clear, compelling path to an outcome that works for them.

Yes, logic matters. But only when that logic persuades. Because even the most rational people make decisions emotionally, and then justify them intellectually.

That’s why storytelling is such an important weapon for you as a CFO.

Next week, we return to the numbers and how to extract the story buried in the data rubble.

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Disclaimer: I am not your accountant, tax advisor, lawyer, CFO, director, or friend. Well, maybe I’m your friend, but I am not any of those other things. Everything I publish represents my opinions only, not advice. Running the finances for a company is serious business, and you should take the proper advice you need.