5 "Tricks" I Use for Effective Storytelling

If you want people to care about what you write or say at work – you need to contextualize.

Because if you don’t? Two unfortunate things can happen:

People outside of your world won’t “get it.” Your work’s influence will be limited.
You’ll only know how to tell strong stories when you have numbers that speak for themselves. And when you don’t? You’ll struggle.

So what qualifies as "good" contextualizing? It's anything that quickly minimizes the gap between your domain knowledge and your audience's understanding.

(Notice the emphasis on "quickly," as we're not trying to turn our audience into domain experts. We're just trying to minimize their mental tax.)

In fact, the best operators take the concept of contextualizing a step further. Because it's not just about landing the facts. Sometimes you're actually trying to sell.

Of course, different situations call for different contextualization techniques. Here are the top 5 "tricks" I rely on:

Leverage shared knowledge.
Anchor on indexed figures.
Redefine the yardstick.
Explain with timeframes.
Paint the "but-for" picture.

▌ #1 Leverage shared knowledge.

Messages are easy to land when the datapoints are self-explanatory; this usually happens when they're tied to a common knowledge base.

For example:

“She makes a million US dollars a year.” (Yes, that's always a lot.)
“We doubled our market share to 40%.” (Yes, impressive in any context.)
"Our customer satisfaction score is only at 60%." (Yes, that's rarely acceptable.)

But what happens when there's no shared knowledge base? Then people have no idea how to feel. For example:

"We acquired +100,000 new users this year" (Stunning achievement or colossal failure?)
"Our average user spends 25 dollars on our app every year" (Underwhelming or actually incredible?)
"Asia has added 1.5 billion new internet users over the last decade." (Is that a lot?)

A common mistake people make? Trying to rectify this by telling people how to feel, instead of actually showing. For example:

"We acquired a whopping +100,000 new users this year"
"Our average user spend ($25) has exceeded expectations"
"Asia has added 1.5 billion new internet users over the last decade - an incredible feat of digitization."

Of course, all this signposting is better than nothing – but it fails to meaningfully persuade. If you don't already possess some prior knowledge in this instance? The numbers mean very little to you.

So instead, imagine leveraging shared knowledge bases and contextualizing as per below:

"We acquired 100,000 new users this year; for context, that's more than the total number of users we had just 18 months ago!"
"Our average user spend was $25 this year; that's on par with the biggest player in our industry!"
"Asia has added 1.5 billion new internet users over the last decade – that’s the same as all existing internet users in Europe and the Americas today!"

Of course, note that your audience's proximity to your world matters. The "farther" away they are, the more intentional you need to be to find the right base of shared knowledge.

▌ #2 Anchor on indexed figures.

One of my biggest pet peeves at work? Seeing ginormous numbers on presentations. Things like:

...535 million watch hours
...256 million clicks
...350,000 transactions

Why? Because when numbers are aggregated in such a way, they're not inviting. They're so far beyond comprehension, that they're actually alienating (and often intentionally so).

In other words, they're just different ways of saying: "Trust me bro – it's huge."

There's nothing wrong with wanting to impress your audience. But in certain situations, I suggest doing it by leveraging indexed figures.

It is more honest, more inviting – and actually more persuasive.

For instance, consider the framing below instead:

"Our platform has driven 535 million watch hours this year – that means half the adults in this country each spends x minutes a day on our platform" (i.e. indexed at an individual level)
"Our latest marketing campaign has driven 256 million clicks – that is triple the engagement we've seen from similar campaigns in the past" (i.e. indexed against historical benchmarks)
"Our software processes 350,000 transactions everyday – that means 1 out of every 3 purchases goes through us" (i.e. indexed against the total "pie")

Remember: when it comes to datapoints, bigger isn't always better. Contextualizing is about reducing mental tax and fatigue for your audience – not increasing it.

▌ #3 Redefine the yardstick.

Contextualizing isn’t just about finding benchmarks for revenue, profit, or users.

Sometimes it’s about turning the game on its head, so YOU can define what you deem to be the right “context.”

For instance, imagine that you represent a small (but fast-growing) market, and you're trying to secure resourcing for future growth.

You won't get very far if you simply talk about dollars and cents in their rawest forms. You're too small to matter (for now).

But consider the attention you could land by proposing new "yardsticks," such as:

...your market's contribution to incremental growth
...your market's headcount efficiency
...your market's speed of execution

The thing to realize about contextualizing is this: it's not always about remixing existing datapoints. That only takes you so far.

Instead, if you think of contextualizing as reframing – it then opens up a lot of possibilities.

In our example above, our audience is almost always wired to only pay attention to markets that are already big today. We're not in that bucket – but that doesn't mean we don't have a case.

So to give ourselves a fighting chance? The onus is on us to reset the context and challenge our stakeholders to consider our argument from another angle. That's what it means to "redefine the yardstick."

Of course, let's be clear: contextualizing is not about hiding unfavorable metrics. Nor is it about wilful ignorance of competing arguments.

Rather, it's about finding low-lift ways to access your audience's mindspace – so that you at least give yourself a chance to "sell."

Sure, you may not be successful in the end – but that is categorically better than being rejected outright at the door.

▌ #4 Explain with timeframes.

Contextualizing is not always about volume and quantity. Talking about timeframes can easily bring your narrative to life.

And there's actually two ways to go about this.

The first way is this: contextualize by talking about the before and after. Tell your audience what's changed.

So instead of saying:

"Thanks to the new software, our employees now spend less than an hour a quarter filing expense reports..."

It's much more powerful to say:

"Thanks to the new software, our employees went from having to waste 5 hours a quarter dealing with expenses to less than 1 hour a quarter."

Of course, you can also make use of principle #2, e.g. –

"Thanks to the new software, our employees now spend 80% less time filing expense reports."

Meanwhile, the second way is this: contextualize by focusing on speed.

For instance, instead of just saying:

“Investing in this initiative could help us achieve x% product adoption."

Try saying:

"Investing in this initiative could help us reach product adoption goals 2 years ahead of schedule."

▌ #5 Paint the "but-for" picture.

Contextualizing isn't only about measuring what we can see. Sometimes it's about what we can't.

And in those cases, you can be more persuasive by painting the "but-for" picture, a.k.a. the counterfactual.

For instance, instead of saying:

"We monetised in this market too late and missed out on a lot of growth..."

It's much more persuasive to say:

"Had we started monetising in this market 3 years ago, we would've had a $100M ARR contributor to our business today."

You can also paint a counterfactual picture of the future, and bring the opportunity cost into your narrative.

For instance, instead of simply saying:

"If we prioritize launching feature X by end of year, we could grow revenue by an additional 2~3%..."

Consider saying:

"If we do not launch feature X by end of year, we risk leaving $10~20 million ARR on the table..."

Of course, this is where you need to be careful. Painting a picture of the counterfactual doesn't give you the right to fabricate the counterfactual.

So if you intend to contextualize this way? Make sure your assumptions are solid in order to protect your credibility.

Extended Reading

Contextualizing is especially critical when it comes to building exec-ready slides. And over the years at Google, I've developed specific principles on how to do so.

Feel free to grab it below (3000+ downloads so far):