Persuasiveness as a skill

Being persuasive is a skill that enables entrepreneurs to be good at the many hats they wear; here's how persuasiveness breaks down and how it can be fortified

I often hear people claim that founders need to be good at sales and good at storytelling. While it’s hard to deny that these are essential skills, I think they miss the mark of the high-level skill that they’re both linked to: persuasiveness. Entrepreneurs who are persuasive are able to convince other to accept a desired way of thinking.

Founders need to exercise their persuasion skills frequently, across the many hats they wear. A founder who is persuasive will end up being good at sales, fundraising, recruiting, managing a board, managing a team, and more.

So what does it look like to be good at persuasion? There are many different recipes for being persuasive, and everyone’s recipe will be a little different. But they boil down to five ingredients: intellectual honesty, empathy, reasoning, storytelling, and charisma.

  1. Intellectual Honesty is the practice of seeking the truth – regardless of if it aligns with your personal beliefs or that you want to be true. People who are truth-seeking and objective will be able to based their arguments in the objective hard truths. They’re able to objectively assess the viability of their own arguments, and therefore are able to root their arguments in objectivity and maintain a high bar for what claims they can make with conviction. If a founder indexes high on intellectual honesty, then their arguments can persuade even some of the most skeptical people. If persuasiveness is getting someone to accept a desired way of thinking, then intellectual honesty ensures that the desired way of thinking is, well, correct.

  2. Empathy is the ability to understand someone else’s feelings and motivations. In some ways, practicing empathy is applying intellectual honesty to the person sitting across the table. Rather than pushing arguments on them, high-empathy people are able to understand the conditions and truth behind someone else’s motivations. Empathy discovers what the person across the table actually wants – not what you want them to want. With fundraising, I find that founders who fundraise with empathy for the investors usually do really well. Rather than trying to shove their pitches down the throats of the people on the other side of the table, they start from a place of understanding for an investor’s motivations and incentives, and can talk about their startup (and deal) in a way that addresses the investor’s needs. Empathy helps you understand the people are talking to so that you can know what it will take to get them aligned to your way of thinking.

  3. Reasoning is the ability to think about something in a logical, sensible way. It builds on intellectual honesty. While intellectual honesty results in the acceptance of the objective truth, reasoning enables you to use those objective truths to construct arguments that are highly logical and can stand up to scrutiny. Strong reasoning also results in strong objective-handling and conversational persuasiveness. People with strong reasoning skills can answer follow-up questions or address concerns that pop-up in ways that are highly logical and therefore finish the job of getting someone aligned to your way of thinking. Strong reasoning also makes your persuasiveness scale. People with strong reasoning skills can write essays, emails, or decks that persuade people even when they’re not in the room.

  4. Storytelling is the ability to reveal something in a way that captures the audience’s attention. Being a good-enough storyteller ensures you can capture someone’s attention long enough for your intellectual honesty, empathy, and reasoning to get to work and persuade them. Someone who rates highly on those first three ingredients but has no storytelling abilities may struggle to persuade – they may have the strongest, most reasonable argument, but if the audience is too bored by the argument to read it or listen to it, then they won’t be persuaded.

  5. Charisma is the charm that makes others enjoy being around or listening to someone. Charisma is the icing on the cake of persuasiveness. It can make someone incredibly persuasive only if the rest of the cake’s ingredients (intellectual honesty, empathy, reasoning, and storytelling) are there. Otherwise it’s just a pile of icing. People who index high on charisma and storytelling without intellectual honesty, reasoning, or empathy may end up leading cults or finding themselves in prison. WeWork’s Adam Neumann and Fyre Festival’s Billy McFarland were both incredibly charismatic founders indexed low on intellectual honesty and reasoning. While they were incredibly persuasive for a while, persuasiveness based on charisma alone is not sustainable and the clock runs out eventually. Not all founders need to be incredibly charismatic. But a baseline level of charisma – where others enjoy hearing what you have to say – can be a force multiplier on persuasiveness.

So if these are the ingredients to being persuasive, how do you build these skills? While sometimes these skills are forged in the fire of trying to build something, there are two ways that aspiring founders can build these skills any time throughout their careers, regardless of their current job: (1) writing and (2) community building.

  • Writing: Writing an essay is a practice in trying to persuade the reader to accept your way of thinking. Writing fortifies your intellectual honesty, reasoning, and storytelling. While verbal arguments are easy to make, writing something coherent and persuasive pushes you to be more truth-seeking and to construct your argument in a way that’s highly logical and can stand up to scrutiny. At places like Amazon, the people who are most persuasive are those who can write compelling arguments – whether it be in emails or in longer-form narratives. Especially if you already index high on charisma, then focusing on writing can turn you into a much more persuasive person. And I’m not just talking about easy twitter threads – I’m talking essays. 

  • Community building: Building a community builds charisma and storytelling. In order to create an online or offline community that people want to engage with, the leader of the community needs to have enough charisma for people to want to show up in the first place, and have the storytelling ability to explain why a community should exist. New communities require that the founder establish the community guidelines, expectations, and purpose of the community with their own presence and actions first. The early members of a community likely will join purely by the persuasiveness (and charisma) of the founder of the community.

Persuasiveness is one of the most valuable skills someone building an entrepreneurial career can have. While being “good at sales” is something that entrepreneurs may use whenever they need to tell, being persuasive is something that entrepreneurs will use every day in a variety of disciplines. And it’s not just an innate thing that you either have or you don’t – it’s a skill that anyone can build by working on the underlying ingredients.