Find The Win-Win Opportunity

You’re reading an excerpt of Great Founders Write, by Ben Putano, writer, entrepreneur, and book publisher. He’s the founder of Damn Gravity Media, a publishing house that inspires and educates tomorrow’s great founders. Purchase now for lifetime access to the book and on-demand video course.

How to Persuade Without Losing Your Soul

My junior year of college was an odd one.

Living in my fraternity house, I’d regularly stay up until 3:00 or 4:00 a.m. with my friends. Then I’d be up at 6:00 a.m. to head to work at Northwestern Mutual, an insurance and wealth management company. I was an intern, but not the type that made coffee runs and collected mail. I was a licensed insurance agent.

At 7:00 a.m., I’d be in the office for our agent meeting and to hit the phones. The first hour of every day was spent cold-calling strangers to talk about death and money. Like I said, it was an odd year.

But this experience taught me the art of persuasion. I was a college student (and not a very good one) trying to sell life insurance to doctors, lawyers, and families with small kids. Why would they even take a meeting, let alone buy something from me?

It wasn’t easy, but I ended up in the top 10% of agent interns in the country that year. It was my first taste of making real money (which was quickly wasted), but the lessons learned were far more valuable. As a founder, I use the skills I acquired from that internship every single day.

Great Founders Persuade—Ethically

A founder’s job can be distilled to two tasks:

1. To build

2. To persuade

Founders build products, audiences, processes, and teams. For many founders (especially those without a sales background) this is where they stop. “Build it, and they will come” is still a pervasive mindset, even if the founder knows it’s not true. Deep down, they hope it’s true, because building is what they’re good at. Building is in their comfort zone.

What’s not in their comfort zone? Persuasion.

Let’s take a quiz. On a Scale of 1–10, how comfortable are you with persuading others? Be honest. A 10 means you aren’t just comfortable—you find joy in it—whereas a 1 means you avoid persuasion at all costs.

Most founders fall somewhere in the middle. Persuasion is a necessary evil. They do it when they need to, but they avoid it when they can.

Why are so many people uncomfortable with persuasion? Because they confuse persuasion with manipulation. The two things couldn’t be more different. Persuasion is the art of finding common ground with someone—a win-win solution. Manipulation is a tactic used to trick a person into a one-sided deal.

Persuasion is rooted in empathy. You need to put yourself in the other person’s shoes. The most persuasive people are also the most empathetic. Manipulation is rooted in narcissism. Manipulators don’t care about the other person. They are just out for themselves.

The most persuasive people believe deeply in their cause. Their conviction is palpable. They want nothing more than to see their vision become a reality. Manipulators don’t really believe in what they’re selling. They’re in it for the money and power.

The first step to becoming more persuasive is believing there is such a thing as ethical persuasion. If you think persuasion is inherently wrong, you’ll never get comfortable with it. To ensure you’re persuading ethically and not slipping into manipulation, consider what makes persuasion ethical.

Ethical persuasion has the four following characteristics:

1. Conviction. Do I believe deeply in my business and services?

2. Honesty. If an objective third party looked at my position, would they conclude that I’m being honest and transparent?

3. Win-Win. Is this in the best interest of the other party? If not, how do I create a win-win situation?

4. Choice. Does the other person still have a choice? Be sure you aren’t backing them into a corner or putting an uncomfortable amount of pressure on them. Ethical persuaders are ok with the final decision no matter what.

Have I persuaded you that ethical persuasion is possible? Good, now let’s talk about how to do it.

4 Steps to Ethical Persuasion

According to research by USC Professor Jay Conger (which first appeared in the Harvard Business Review), there are four steps to becoming more persuasive in the workplace:

1. Establish credibility

2. Find common ground

3. Use vivid examples

4. Connect emotionally

While this research was conducted on corporate organizations, it applies to startups as well. Let’s look at each through the lens of a founder:

1. Establish Credibility

Founders inherit a certain level of credibility in their own companies. This is called positional credibility—authority earned by the nature of their role.

But positional credibility can backfire if abused. Founders who demand or manipulate, rather than persuade, are not long for the startup world. Your smartest employees will leave, and you’ll be stuck with yes-people who don’t know what they’re doing. Don’t rely on positional credibility.

Real credibility is established by deep experience, sound decision-making, listening to feedback, and consistently showing up and doing the work.

Credibility is not universal, either. As a technical founder, you have credibility on development decisions, but maybe not marketing or sales decisions. You may have deep experience in one industry (e.g., hospitality), but what happens when your startup pivots to micro-office space? Credibility must be earned in every vertical and every function of the company.

So what do you do when you find yourself wading into an area where you lack credibility? You borrow it. Before presenting your case to the team or investors, build a coalition of people who have deep credibility in that specific area. Ask them questions about the feasibility of your idea, what roadblocks may occur, and why (or why not) the company should take this direction. If the experts are on board, ask them to vouch for your decision. Borrow their credibility to supplement yours.

How do you establish credibility when writing? Same as you would in a presentation or board meeting. Answer the question, “Why should we listen to you on this subject?” If you have earned credibility, say why. “I’ve spent fifteen years in the commercial real estate market.” If you haven’t earned credibility, cite sources who have it. “Jeanne Gang is a world-renowned architect. Together we developed this plan.”

Once you’ve earned or borrowed the credibility you need, turn your attention to those on the other side of the table.

2. Find Common Ground

The crux of ethical persuasion is finding common ground—a win-win scenario. Your goal isn’t to create the absolute best deal for yourself, but to find a solution that both parties can be satisfied with. You want others to walk away feeling like they could work with you again. Play the long game.

Finding common ground is an act of empathy. Let’s revisit the empathy-building questions we asked in Know Thy Reader:

1. Who am I writing to?

2. What do they want?

3. What do they need?

4. What stands in their way?

5. How can I help?

6. Why should they care?

For persuasion, one more question to ask is: “What objections will the other party have?”

Let’s say you think you need to shut down a poor-performing product: the Ultra Widget. It’s not worth the time and resources your team is putting into it. You need to put more energy toward your best-performing tool (we’ll call it the Super Widget). But the Ultra Widget team still believes in its potential and doesn’t want to give it up. How do you persuade them it’s best to shut it down?

As a founder, you have two options.

Option one: Mandate they shut it down and move on. This path may be quick, but you also risk pissing off a lot of people.

Option two: Make your case. Let’s use the questions above to craft a persuasive message:

1. Who am I writing to?

   The Ultra Widget team: Raj, Cecily, and Stephen. They’ve been working on Ultra Widget for nine months.

2. What do they want?

   The Ultra Widget team wants to continue working on Ultra Widget. It was Stephen’s idea in the first place. He recruited Raj and Cecily early on to build it. They believe it can become a game-changing tool for the industry. They want just six more months to prove its value.

3. What do they need?

   The team needs to feel successful. By shutting down Ultra Widget, they may feel like they wasted nine months of work on nothing.

4. What stands in their way?

   Mountain: Ultra Widget has about one-third of the daily active users as the company’s most popular tool, Super Widget. Worse yet, user growth has slowed to a crawl.

   Villain: They’ve developed a “failure is not an option” mindset. Raj, Cecily, and Stephen are convinced that if Ultra Widget fails, they will be seen as failures by the company and that they may even lose their jobs. They believe their reputations are at stake.

5. How can I help?

   First, the team needs to know a product failure is not personal failure. Are scientists upset when an experiment fails? Of course not! They’re elated because they learned something new. The team needs to know their jobs are safe and their time working on Ultra Widget was NOT wasted.

   Plus, it hasn’t been all bad with Ultra Widget. The team has learned valuable consumer insights and they’ve developed a few innovative features. We can try to incorporate Ultra Widget’s most popular features into Super Widget.

6. Why should they care?

   The Ultra Widget team did not fail. They exemplified the startup’s mission and are a testament to the incredible things they are building together. Even though Ultra Widget did not succeed, we can use it to propel Super Widget’s user growth. If we’re all rowing in the same direction, we’ll reach our ultimate goal—an IPO—faster.

7. What objections will they have?

   • “What will six more months hurt?”

   It’s just not Ultra Widget’s slow growth that’s a concern. We also need to consider Super Widget’s massive growth. We see this as the opportunity for us, and we need all hands on deck to succeed. We can’t waste any more time pulling in different directions.

   • “What will we tell Ultra Widget’s best users?”

   We’re incorporating UW’s best features into Super Widget. It will be better than ever. But at the end of the day, we can’t make everyone happy.

   • “What will we do now?”

   We need you on the Super Widget team.

   Notice how we found common ground with the Ultra Widget team. We framed the decision to shut down Ultra Widget as a win-win. The company can now grow faster, and the Ultra Widget team will contribute to this.

Finding this amicable solution wouldn’t have been possible without deep empathy. As a founder, you need to understand the emotional impact of your decisions. The best persuaders take emotions into account—they don’t try to bulldoze over them in the name of logic and efficiency.

3. Use Vivid Examples

Sara Blakely had a problem. Before her brand of shapewear, Spanx, became a household name—and before she became the first self-made female billionaire in the US—Blakely couldn’t even get her product into stores.

Early customers absolutely loved their Spanx. It solved a problem that long plagued women’s clothing, one that many women had found homemade solutions for. But when trying to explain the problem to department store buyers, it never clicked.

On the hit podcast, How I Built This with Guy Raz, Blakely shared the story of how she finally got Spanx into Macy’s. While meeting with the department store’s senior buyer, Blakely couldn’t get her to understand the value proposition. Despite the sales figures and customer testimonials, the senior buyer was not convinced.

Finally, out of desperation, Blakely decided to literally show her what Spanx could do. She took the buyer to the nearest restroom and stepped into the stall. She stepped out no longer wearing Spanx under her dress. The senior buyer could instantly see the difference in the way Blakely’s dress fit her. Macy’s started selling Spanx immediately.

Blakely, like all great persuaders, understood that vivid examples are more convincing than numbers.

As a writer, you can use stories to add vivid examples to your work. I opened this book with a story about Benjamin Franklin. If you remember anything from reading Great Founders Write, I would bet it’s that story (but I hope it’s much more). Stories stick in our brains better than facts and figures, which makes them potent tools for persuasion.

Don’t get me wrong: numbers are still critical to crafting a persuasive argument. But they aren’t enough on their own. Use numbers to justify your argument, not make it.

4. Connect Emotionally

Suneel Gupta—entrepreneur and author of Backable— spent years researching what it takes to raise venture capital. Gupta saw that some founders had that “It” factor … but what was it?

After years of researching the question, Gupta discovered that the most persuasive founders had one thing in common: conviction. They believed deeply in their cause and company.

Contrary to popular belief, people aren’t persuaded by logic—they’re convinced by emotion. People want to see you are emotionally committed to your venture. You don’t just believe it in your head—you believe it in your heart and soul.

But emotion is a two-way street. You also need to understand the emotional state of your audience. What type of energy should you use to present your new idea? Should you go in strong and opinionated, or soft and guiding? If you get the emotional tone wrong, you’ll lose your audience immediately.

Go back to the section Know Thy Reader, question #3: What does your audience need? Do they need reassurance that they’re livelihood is safe? Are they craving novelty or self-expression? Use this question to probe the emotional state of your audience and connect with them on their level.

Practicing Persuasion

Persuasion is an art. Like all art, it’s rooted in empathy. Your goal is not to win, but to create a win-win scenario for you and others involved.

There’s one last thing to keep in mind about persuasion: it takes practice. As a life insurance agent, I would literally role-play sales conversations with my boss to hone my persuasion skills. We’d also review after meetings and phone calls to identify what I did well and where I could improve.

I recommend keeping a journal of your persuasive conversations. Record the details of the situation, what went well, and where you could improve. What objections came up? What did you learn about the other party that could help you create a better win-win solution? What facts or vivid examples could you add to strengthen your position?

When you really believe in something, persuasion will no longer feel like a necessary evil. It will feel like a natural step in the journey of building your vision.