Storytelling for dummies — P2 — Crafting your story (with bias towards startups)

8 min readMar 17, 2020


In the first installment of this 3 part series on storytelling we spoke about THE LEVERS OF GOOD STORYTELLING, that is, connecting to mission and amplifying human emotion.

It’s about connecting, as humans

Storytelling is the not-so-secret ingredient that makes the difference between being a manager and being a leader, between closing a customer and winning a lifelong fan.

It’s about conveying a message clearly and simply. It’s about connecting with your audience not as customers, executives or investors, but as humans.

“We took pride in the fact that reviewers talked mainly about the way ‘Toy Story’ made them feel and not about the computer wizardry that enabled us to get it up on the screen,” Ed Catmull, co-founder of Pixar, recounts. “We believed that this was the direct result of our always keeping story as our guiding light.”

For startups and founders, being persuasive is as important as having vision.

Often times, we trust leaders not because their vision is perfect, but because they have it under control. They communicate clearly without giving us all the answers. What most people think of as vision is actually persuasion.

People remember a totally random sample of the information you give them about what you do. It won’t always be the best sample, or the summary you wish you could hand them. It’s a random set of data.

Yet, people pack presentations with every selling point they can think of. But that’s actually the worst thing to do. You want to construct a message that — when sampled at any point — reinforces your argument and remains persuasive. Keep it to the highlight reel and stick to a very short, simple message that you repeat in different ways again and again. When there are fewer things to remember, your audience is more likely to remember what matters.

To tell stories that persuade, emphasize possibility and potential. It must be crystal clear why the product you’re selling is not only different but better. Building a persuasive, bulletproof narrative that will grab people’s attention, get them to question existing solutions, and ultimately convince them that not using your product is costing them big. To do this, generate gaps of ignorance in the audience and fill them with our idea.

Trouble is, most tech operators express themselves with complexity, nuance, facts and figures. Talk to users in their own language. Use concepts and processes that your users are familiar with in order to communicate software designs as naturally as possible.

CRAFT YOUR STORY Less Text, More Visuals

When you have visuals on the screen or use visual language and not a lot of text, you make people dependent on you as the presenter to know what’s going on. You have the authority in the room. The slides never will.

When you put up a slide covered with text, you are literally giving up your power to shape a story and command attention. If your goal is to show there is a lot of room in the marketplace, using visuals engages in this idea while entertaining your audience at the same time. Give yourself the space to riff, to move anecdotes around, and respond to the mood and reactions in the room.

Remember, as natural as you want things to seem, you’ve laid out a very carefully and intentionally crafted story. There is drama. There is an arc. There are points you need to make. It isn’t like a regular conversation at all. When you practice in front of people, what grabs them? When do you see the emotion on their faces? How can you double down on those remarks?

Put me “in the room” anecdotes that provide a tactile sense of experience, take your audience on a journey, and create drama. Sometimes, the most important stories are the ones that are told within your organization. When you have a well-crafted, specific, controversial or non-obvious company story, it can guide everything from whom you shouldn’t hire to how you settle arguments.

— you should only write down your story if you are willing to make it controversial and memorable.

Similarly, moments of reflection should be scattered throughout your talk to grab attention, create intimacy with your audience, and give them a window into your process. It might say something like, “I knew we were onto something the moment I met Sandy and she said this one thing.” This cues the client to pay attention.”

If a sentence includes a mini-cliffhanger, raising a question in your mind. Your audience reads on because they want to find out the answer: What’s different? Why does the traffic spike? When an author raises questions, readers want to know the answers. That’s how you keep them hooked.

Tell your audience ‘this is a point that is important to me’ to tell them ‘this is a point that should be important to you.’ Finding that “lock” that authentically intersects your story with someone else’s is what makes persuasion happen. It enables you to establish rapport, build relationships, and earn trust from your audience so that they see you as truly in the same tribe.

I will always recall one of the first pitch days I attended. Three startups were invited, all boasting latest world-changing technologies. Today, I can only recall one of those pitches. It was for a company our community later invested in. The founder was developing sensors for autonomous driving cars, but, in his 10-minute pitch slot, there was never any mention of how — he took the time to emphasize the WHY. He was a renowned university professor, and at an advanced age, decided to leave the comfort of an academic post to initiate a startup. A loved family member sadly suffered a terrible traffic incident, and he had unique insight into a technology that could minimize the risk of similar accidents happening to others. His story had, depth, meaning and purpose. It also served a goal, to convey to us that he possessed the knowledge to execute his idea, and his personal story convinced us that he will persevere the trials and tribulations of a startup to get to his target. The room was sold.

I am a fan of the Problem — Solution — Specifics narrative framework:

Conflict is the force that drives a story. No conflict, no story.

What matters to storytellers is that audiences won’t be interested in a story if there is no conflict. Conflict sparks interest. Customers won’t be interested in your story, if it isn’t relevant to a ‘conflict’ or problem they are struggling with.

Identify your problem: What are the pain points you want to solve? Who has them? How are they currently solved or not?

Solution: What has changed to make new solutions to your problem available? How does your new solution work to solve the problem?

Specifics: What are the quantitative and qualitative proof points that validate your argument?

Once you have this framework mapped out, you can start filling in each section with the information that will make the biggest difference for prospective customers’ specific situation — product-market-fit is all about customer success.

What’s the Problem?

Finding new customers for your local business is hard. With all the time you spend running your business, who has time to figure out how to drive new business through the door? But if you don’t grow your customer base to find new, repeat customers, how can you get off the hamster wheel and grow your business?”

Notice how colloquial the language is. Your explanation of the problem needs to be clear above all else, and shouldn’t be overly elaborate or packed with jargon. It should be built to relate directly to the person with the problem.

Who has the problem?

You want to make sure you’re talking to the right person (the one who needs your product and has the power to buy it) Your number one goal is to focus on the people who are purely responsible for eliminating these pain points — the jobs-to-be-done — not necessarily the CEO.

What is the problem costing?

A good rule of thumb to make sure you’re targeting who has budgetary control of the resources allocated to solve the pain points your product fixes. The easiest way to do this is to shed light on all the money they’re losing because of the problem you’d solve. Sometimes these costs are very concrete: A company is paying for a ton of data storage, let’s say, and your solution is storage virtualization that will be much less expensive. With a little research, you can estimate dollars saved. When it comes to qualifying clients, the best sign that you can and should go after someone is if they are already spending budget to bridge the gap.

It can also be opportunity cost: Your solution may allow a company to do something much more effectively and capture more revenue. For example, maybe you build software that lets sales reps get more done in the same amount of time. Now, instead of closing eight deals at an average value of $8K a month, they can close 10 deals a month — a 25% bump and $16K more revenue per rep per month. These types of boosts can be harder to prove but are very compelling to customers.

You have to be able to demonstrate thorough market knowledge, and show a delta between what people have now and what you can do for them. To make your solution a contender, you have to identify where this process is weak and where it breaks.

Customers want a resource, not just an answer. If they can ask you questions about the broader market or issue — not just specific to your product — and you can come back with smart, well-researched responses, they’re more likely to see you as an asset and trust your opinion.

What changed? Why Now?

Being able to explain what has changed in the technology or marketplace will not only strengthen your narrative’s realism, it will also make you appear more informed and forward-looking than your competition.

Once you’ve explained what’s changed to clear a path for your product, you need to explain how you’re harnessing this change to do something no one else is doing better. The most critical thing is knowing how to easily explain this in an understandable way to your prospect.

You should know the general metrics by which existing solutions are measured and the qualitative comparisons you can use to help people understand what you’re doing quickly and easily. The language you use has to be familiar, simple, and speak directly to what your audience values.

Numbers are your sales narrative’s best friend

You should be able to say something as simple as, ‘Our offering does more X’ or ‘Our offering requires less Y,’ where X and Y are known and important.

To really strengthen your narrative, you should look at the many metrics that exist closer to the actual work, not just people’s goals. Not just KPIs, but Jobs-to-be-Done. They probably have more to do with the day-to-day than quarterly results.

Qualitative information — client testimonials, etc. — can be very compelling, but you want to back them up with metrics whenever possible. Get customer testimonials that highlight numbers, not just adjectives.

A recent testimonial for a cloud based solution I received was that it transferred decision-making from back office to front office. A client question no longer needed back-office analytics, with a two-day turnaround time to be responded to — a sleek real-time dashboard placed the narrative literally in the palm of the sales team. The new solution was a no-brainer. It was not the technology that sold, but the customer success narrative.

This post is part of a 3-series about storytelling:
Part 1 — its purpose and history
Part 2 — crafting your story (with bias towards startups)
Part 3 — tips and techniques to equip storytelling into your utility belt

For more information —



AdiG Early stage company advisory and startup fund raising. Human connections that build relationships, add value and move the needle