6,382 words ~ 20 min read

Six fundamental skills for founders

Six fundamental skills for founders

Skill 1: Become a better thinker

Our brains are wired to think in patterns, but it might be hurting your decision-making.

In normal times, being an entrepreneur can feel like constantly swimming upstream. Each day involves a continual onslaught of decisions, big and small, to be made by you and you alone. But in times of uncertainty, while businesses scramble to adjust to evolving markets and work conditions, entrepreneurs are facing more daily decisions than ever. It’s no wonder that according to the World Economic Forum, an average of 45% of adults globally said their mental and physical health has become worse in the past year.

As CEO of my company Jotform, it would be easy to slip into cruise control just to get through another jam-packed day; to keep swimming along and forget to think about how I’m thinking and making decisions. 

But unaware decision-making can lead to a less innovative, less productive and less inclusive workplace and ultimately hurt your business. That’s why it’s critical to recognize your current thinking patterns and how to do it better. Here are five expert-backed strategies to improve the quality of your thoughts.

1.1. Think about thinking

If you’re reading this chapter of our bootstrapping guide, then you’re already knocking out strategy number one. According to Ness Labs, metacognition — the practice of thinking about your thinking — helps you to analyze your thought processes and, in doing so, improves the quality of your thinking. And though it may sound complicated, metacognition simply requires carving out some space for self-reflection, which can be done through daily journaling, regularly checking in with your thought processes and practicing some of the techniques below. 

As long as you’re conscientious about how you think, you’re off to a good start. 

1.2. Be aware of loops

Many of us are familiar with behavioral loops — the way we automatically look both ways before crossing the street; or how your mouth waters when you walk into your favorite restaurant. Similar to these learned physical reactions, our minds develop certain “loops” as well.

Mental loops are not inherently bad — in fact, sometimes we need them to process the barrage of new information throughout the day. As Zat Rana writes, “Our brain is a pattern-seeking survival machine, and habits are how it ensures that we don’t have to think too hard about what to do when familiar situations arise, letting us conserve energy.”

But they can also lead to blind spots. Writes Rana, “Our brains have learned something in one context, so they mistakenly apply it to others, mixing up the triggers that lead to routine thoughts.” For example, you assume that a new business issue requires the same old solution, rather than searching for a better answer.

The way to counteract loops is to train our minds to think critically — reading books, hearing out conflicting opinions, educating yourself about divergent ways of perceiving the world. Also, you can practice different mental models, as explained below. 

1.3. Add to your mental model toolbox

As entrepreneur Charles Munger once said, “You’ve got to have models in your head. And you’ve got to array your experience both vicarious and direct on this latticework of models.”

In other words, we arrange new information based on the existing infrastructure in our brains. The good thing is, we can diversify the kinds of models available and that way, achieve a deeper and more nuanced understanding of that new information. One way to increase your available mental models is simply to study and practice them. Take, for example, the first principles mental model, which entails breaking down complicated problems into individual elements, then rebuilding them from the ground up. Or the inversion technique: Think about what you want, then, think of the opposite of what you want — a surefire way to achieve a new perspective.

Entrepreneurs can also try organizing employees in a way that ensures cross-fertilization of mental models. A few years ago at Jotform, our employees began working in small, cross-functional teams. Whereas a designer would see a challenge from one perspective, an engineer would come at it from a completely different angle. The results were undeniable — not only were employees happier and more motivated, but our products improved. 

On a personal level, expanding your mental model toolbox will help you make better decisions. 

1.4. Make diversity the rule not the exception

Of all the reasons to embrace diversity, here’s one: It will boost your thinking and your company’s innovation. Harvard Business Review authors analyzed more than 150 companies and found that after women join C-suites, they don’t just bring new perspectives, but they actually shift how the C-suite thinks about innovation, leading them to consider a wider variety of strategies for creating value. Importantly, the shift happened in particular where teams already had at least one woman. 

Having more diverse perspectives can make groups more open to change. And as any entrepreneur can tell you, change is integral to innovation. 

1.5. Remember emotional agility

As much as we’d all like to see ourselves as completely objective decision-makers, especially when it comes to our businesses, it’s undeniable that emotions play into our daily choices. While we might expect anger could lead to brash or impulsive decisions, it turns out that positive moods can affect our better judgment too. 

The key to overcoming this tendency is to develop awareness and practicing emotional agility. As Ness Labs explains, “Emotional agility encourages you to observe your inner world and to build resilience. Such a compassionate and honest relationship with your emotions will help in limiting their clouding effect on your judgement.” Not only that, emotional agility can relieve stress, reduce errors and improve job performance.

So, how can you become more emotionally agile? According to HBR, the key is to recognize your patterns; label your thoughts and emotions; accept them; and act on your values.

Our brains may be wired to work a certain way, but there are easy ways to rewire them to benefit ourselves and our businesses.

Skill 2: Grow your charisma

I wasn’t in the mood for small talk. I’d planned to use my early-morning flight from San Francisco to New York to catch up on emails and put finishing touches on a presentation.

10'000 Hours | Getty Images

So, naturally, I found myself seated next to a friendly traveler who started a conversation with me as soon as I pulled my laptop out of my bag.

“6 AM flights are the worst,” she said with a grin. “What are you headed out east for?”

I told her about the potential clients in NYC and my looming presentation, hoping she’d get the point. 

Instead, she empathized, sharing that her palms always sweat before presentations, and that she pretends the nervousness is excitement to make it through. “A few minutes in, and you’ll feel like you’re with old friends,” she said with a laugh. “So definitely don’t imagine them in their underwear.”

During the descent, my seatmate and I exchanged cards. I hadn’t made the connection at first, but I immediately recognized her name: She, too, was the CEO of a tech startup in the Bay Area, and she’d recently secured funding from well-known investors. 

After our in-flight conversation, I understood what kept me listening to her instead of working on my presentation: She had charisma.

Why entrepreneurs need charisma

Anyone can come up with an innovative idea for a business. To succeed, entrepreneurs also need to convince people to get excited about the vision.

Think about the most successful people in your industry. Successful entrepreneurs don’t do the work solo; they build teams that work hard because they believe in what they’re doing.

As one corporate coach explains, “As an entrepreneur and leader, one needs manpower. And these people take care of your business, when it comes to keeping your customers satisfied and happy with products and services.”

In other words, charismatic people can assemble groups. But it’s not just about building an amazing team. Landing investors, establishing a customer base, and building trust with the public all requires buy-in, which doesn’t just happen because you have a convincing story and a fancy slide deck. 

Charisma, or the ability to combine your confidence with warmth, is what draws people into your great idea and keeps them there. Magnetism isn’t just about charm, but sparking authentic connections with people, as my charismatic seatmate did on the early morning flight.

It might feel counterintuitive to focus more on people than numbers, but if you’re looking for long-term growth and success, building authentic relationships is the best way to build a business.

The good news is, researchers believe charisma is 50% inherent and 50% learned. So if this doesn’t come naturally to you, you can learn it. Here are three of the most effective ways to grow in charisma so you can grow your business along the way.

2.1. Nurture your relationships

Step one to growing in charisma: Care about people. 

People can see through hollow charm, and they can feel when they’re being used. So instead of empty lip service, focus on building real relationships with people you know and people you meet. 

Chances are, you already care about the people in your life. You might just need an extra push to show them. 

The simplest way to do that? Really listen. Ask questions, and pay attention to what’s beneath the surface. Remember the small details, like your co-worker’s birthday or your client’s favorite coffee order. 

What was so striking about my airplane chat was that my seatmate was actually paying attention. She noticed I was a bit anxious about my presentation, so she empathized with and encouraged me. 

Nurturing relationships is also about helping people grow. We all want to be around people who challenge us, encourage us, and help us become the best versions of ourselves.

When you notice what makes other people tick because you genuinely care, you can draw them into an activity connected to their passions — where they’ll be most effective and contribute most authentically.

2.2. Project confidence

Early on in my career, an old college classmate reached out to share a business idea with me with the hope I’d work with him. We emailed back and forth, and as much as I admired his excitement, I wasn’t sold. 

“So are you planning to bootstrap or get investments?” I asked, curious about his plan for getting started. 

“I’m not sure yet,” he replied. “But there’s a market for my idea, so I know it’ll work out.” 

It didn’t work out, and needless to say, I didn’t quit my job to help him.

To promote buy-in, you need to project confidence. People follow passionate leaders who know where they’re going. 

A 2017 article in The Guardian captures it well:

The charismatic can infect others with their own enthusiasm. They convince us, not only of their own self-belief, but make us feel more confident in ourselves too. As an entrepreneur, charisma is a winning formula for your personal brand. If you exude self-belief, angel investors, prospective clients, and the press will see your potential and be more included to invest in your story.

Keep in mind that confidence doesn’t mean perfection. You don’t have to have it all together. The key isn’t to project the lie that you won’t make mistakes, but that you’ll figure out how to navigate those mistakes because you’re invested in your vision and the people who contribute to it.

2.3. Find the sweet spot

Just as too little charisma can impact your growth as an entrepreneur, so can too much of it. A recent study from Ghent University found that there’s a sweet spot when it comes to charisma in leaders. 

Researchers found that when charisma increased in a leader, so did employees’ perception of their effectiveness. But leaders with both low and high charisma scores were viewed as less effective than those with “moderate” levels of charisma.

Why? People view their leaders as most effective when they can adapt to challenges. If your charisma is too low, you may not be as strategic and aggressive. On the flipside, if you’re too charming and people-focused, people might perceive you as lacking in actual job-related skills.

So while investing time and energy in your confidence and people skills can help your business, it shouldn’t be at the expense of your actual work. For all the time you spend networking and nurturing relationships, invest as much time with your head down, figuring out solutions and developing your product or service.

Like many areas of life, success in entrepreneurship is all about balance. None of us can do it perfectly, and your focus will naturally ebb and flow as your business grows. Start by giving your full attention to what’s — or who’s — in front of you.

Skill 3: Learn to sell anything

As a product manager first at Google, then Reddit and Pinterest, Tyler Odean knows a thing or two about the power of persuasion.

Robert Daly | Getty Images

The secret, he says, isn’t so much having a world-changing idea. It’s about getting people on the same page.

“The reality is that visionaries like Steve Jobs haven’t been successful because they thought of something amazing and original out of thin air," Odean said in a 2018 interview. “Rather, they were gifted at constantly persuading many people to follow them on their journey to something amazing and original.”

Odean has been giving talks on persuasion for years, drawing on the principles that psychologist Daniel Kahneman outlines in his book, Thinking Fast and Slow.

Kahneman argues that the brain has two systems for experiencing information: System 1 is fast, automatic, and mostly unconscious. System 2 is slow and deliberate, and requires deeper, more analytical thought.

When it comes to constructing an argument or message, being logically correct is not enough. While an idea may appeal to System 2, you need System 1 on board, too.

“When we look at what visionaries really succeed at, they give us a confident, consistent and coherent plan that makes us feel safe,” says Odean.

We trust them 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.

To be a successful entrepreneur entails much more than convincing people to buy your product or invest in your company. It means creating a deep network of connections who are enthusiastic about your idea and seeing it grow. Here are five ideas on how to start.

3.1. Establish credibility

In addition to pathos (the appeal to emotion), and logos (logical arguments), Aristotle believed that good character, or ethos, was one of the three main pillars of persuasive speech. This is because no matter how well-reasoned or logical an argument is, it won’t matter if the audience doesn’t trust the person making it.

In his now-famous TED Talk on reforming the criminal justice system, Human Rights Attorney Bryan Stevenson opens not with a list of degrees he’s earned or prestigious awards he’s won, but by saying: “I spend most of my time in jails, in prisons, on death row. I spend most of my time in very low-income communities in the projects and places where there’s a great deal of hopelessness.”

This information is far more important to listeners who don’t know who he is, or why they should trust what he’s saying.

Another integral component of establishing credibility, of course, is being honest. A single lie or misrepresentation can often be enough to cause permanent harm to a professional reputation.

As Warren Buffett said: “It takes 20 years to build a reputation and five minutes to ruin it.”

3.2. Really listen

When it comes to being persuasive, it’s important to show people that you can provide a real solution to a problem.

To do that effectively, you have to listen to your audience to really understand what they need and how you can help.

Most of us overestimate our ability to listen. But it’s an important skill to cultivate if we want to be persuasive.

When talking to someone, give them your full attention. Look them in the eye and use their name throughout the conversation. Don’t interrupt. This sends the message that you value that person and their opinion.

Moreover, research shows that if you want to persuade someone, it’s better to listen carefully and respond based on their perspective. With time, the trust that is built through careful listening will enable a leader to influence decisions.

3.3. Make your voice effective

One of the great things about the art of persuasion is that it hasn’t changed much in the last 2,000 years. That’s partially thanks to the fixed nature of our attention spans.

“Aristotle had discovered that there are fairly universal limits to the amount of information which any human can absorb and retain,” Edith Hall, a professor at King’s College, wrote in Aristotle’s Way. “When it comes to persuasion, less is always more.”

When making a point persuasively, Aristotle said that an argument should be expressed “as compactly and in as few words as possible.”

To do this, drop every extraneous word you can from every message you send. Because, according to Odean, if the argument you’re making is too dense, System 2 will be called in to analyze it, and System 1 won’t even have a chance to take a swing.

In that vein, Aristotle also observed that the first thing you say is the most important, since “attention slackens everywhere else rather than at the beginning.” In other words, open strong, since that’s when your audience is the most captive.

3.4. Tell a story

When appealing to childlike System 1, there’s almost nothing more effective than a well-told story. People pay attention differently when they’re hearing a narrative instead of just facts—especially when it applies directly to their interests. According to a 2014 analysis of the 500 most popular TED talks of all time, stories made up 65 percent of the average speaker’s talk.

How to use storytelling for persuasion? The key is to create connections between what your audience is thinking, what they already believe, and what you want them to believe. Layer in facts that will add credibility, using either yourself or someone you know.

As for picking a story, a good rule of thumb is that the most personal content is the most relatable.

As TED curator Chris Anderson put it, “The stories that can generate the best connection are stories about you personally or about people close to you. Tales of failure, awkwardness, misfortune, danger or disaster, told authentically, hastens deep engagement.”

3.5. Be confident

In order for others to believe in you, you have to believe in yourself.

It may sound hokey, but it’s true. Think about it: Are you more likely to believe in someone who appears anxious or unsure, or someone who speaks with authority?

When you speak, people begin to make decisions as a result of the way you communicate. To project confidence, speak calmly and in clear, straightforward sentences. The goal isn’t to sound like a robot, but a competent person who’s prepared and informed. Try to avoid filler adjectives such as “like,” “uh,” and “you know.” If it helps, map out what you intend to say before you say it.

Even if you’re filled with self-doubt, you can fake it — until, eventually, it feels genuine.

Skill 4: Master the art of asking questions

The art of proposing a question must be held of higher value than solving it.

Georg Cantor

We ask questions all the time. When is the presentation? Did you get my notes from the meeting? These are straightforward, fact-finding questions, and they get straight-forward, fact-based answers. (It’s at 3. Yes.) It shouldn’t be surprising that my company, Jotform, sees more than two million user questions per hour.

But a thoughtful, well-posed question has tremendous power; opening the doors to innovation, building cohesion among team members and shining light on the dark corners of misunderstanding. 

Even so, many of us still shy away from asking questions, despite how invaluable they can be. Experts offer several explanations for why this is: Some people are egocentric and more interested in sharing their own points of view. Others are overconfident, assuming they already know the answers. Then there’s the other end of the spectrum: Those who worry that they’ll ask the wrong question and be perceived as incompetent. 

“There are so many vulnerabilities surrounding this,” Warren Berger, author of A More Beautiful Question and The Book of Beautiful Questions, tells Forge. “It can really feel like questions are a dangerous thing.”

In fact, the opposite is true — the most successful people in the world ask questions constantly. If you’re not a natural question-asker, learning how can seem daunting. As the mathematician Georg Cantor points out in the quote above, asking good questions is an art. And with practice, it can be mastered. Here’s how to get started. 

4.1. Be specific 

Before you ask a question to someone else, it’s important to first figure out what you’re trying to learn. If you’re not sure, it’s unlikely that the person you’re asking will either. 

Most questions can be divided into three types: Factual, opinion or request. Each carries its own message. Asking a factual question shows that the other person has information we don’t; asking an opinion indicates we value their perspective; and making a request implies that we need help. Once you’ve gotten to the heart of what question you’re asking, consider who you’re asking, and whether they’re in the right position to answer it or not. 

As a leader, asking questions can feel like a giveaway that you don’t have all the answers. Which, obviously, you don’t. But far from projecting weakness, asking questions is actually not only a great way to gather valuable information; it shows your team that you respect and trust them. 

4.2. Don’t be afraid to clarify

It’s often the case that asking a single question isn’t enough. Maybe the answer was overly technical; maybe you realized that you didn’t ask the precise right question after all. It happens! 

If the answer you receive leaves room for ambiguity, you’ll need to clarify. Usually, these questions are either open, in which you ask the speaker to elaborate on part of their point; or closed, in which you repeat the ambiguous part of the message back and ask for confirmation that you understood it correctly. 

When asking for clarification, make it clear you’re simply trying to understand, rather than blame the answerer for answering poorly. After all, you’re both working toward the same goal, which is to understand each other. 

4.3. Conversation vs. interrogation

There’s a fine line between showing your interest in what someone has to say and making them feel like they’re being bombarded. Rather than asking questions at a machine gun clip, take some time after you’re answered to consider what you just heard. Remember, it’s a conversation, not an interrogation. 

Keeping questions open-ended is a good way to avoid “yes” or “no” answers, and also allow for more creative responses. According to Alison Wood Brooks and Leslie K. John, both professors at Harvard Business School, these kinds of questions can be “wellsprings of innovation.” 

On the other hand, survey design research has shown that “closed” questions can introduce bias and manipulation — leading the witness, so to speak. In one study, in which parents were asked what they considered  “the most important thing for children to prepare them in life,” 60 percent chose “to think for themselves” from a list of possible responses. In contrast, when the same question was asked in an open-ended format, only about five percent of parents gave a response along those lines. 

4.4. Find the right tone

Different circumstances call for different modes of questioning, and how you ask a question can be just as important as what you ask. Overly direct questions that seem to come from out of the blue can make people clam up, but beating around the bush can lead to frustration on both ends. Brooks and John found that people are actually more willing to reveal sensitive information when questions are asked in a decreasing order of intrusiveness — as long as the first question isn’t too sensitive. It’s a balance. 

The same goes for context. If you’re making an important request, you’ll want to pick a time when the other person isn’t in the middle of something else or in a noisy, crowded environment. 

4.5. Keep quiet

In general, it’s a good idea not to interrupt people while they’re talking to you. This becomes even more true when they’re trying to answer a question that you asked. Interrupting sends a clear message that you don’t value what they’re saying, and also keeps you from hearing what they might have said. 

If the conversation seems to be meandering from the topic you want to focus on, gently guide it back. There’s a difference between doing this and cutting someone off mid-sentence because you had a thought of your own to add. Save your own thoughts and questions for when the answerer is done talking — then, wait a beat beyond that to make sure they’ve truly finished their thought. Sometimes that extra pause yields the most important thing a person was going to say. 

Pe world around them — plus, people like them more. If you become a good question asker, there’s no end to People who ask questions have higher emotional intelligence and a greater understanding of the world around them — plus, people like them more. If you become a good question asker, there’s no end to the knowledge you have the power to unlock.

Skill 5: Get what you want from difficult people

According to research by Dr. Brinkman and Kirschner in Dealing with People You Can’t Stand, there are challenging personality types that make our lives harder:

  • The Tank: Confrontational and angry.
  • The Sniper: Makes you look foolish.
  • The Grenade: Explodes into fury out of nowhere.
  • The Know-It-All: Authoritative and things must be their way.
  • The Whiner: Points out everything wrong in vague terms.

You might now be thinking of a person to put one of these labels on.

They could be a friend, co-worker, customer, or family member (circa that tense Thanksgiving of 2016).

No matter what type of difficult personality they have, in the extreme you’ll experience what Robert I. Sutton, Professor of Management Science at the Stanford Engineering School, described in his graphically titled book:

Encounters with rude, insulting, and demeaning people undermine others’ performance — including their decision-making skills, productivity, and creativity.


Still, only about 10% of those you encounter are categorized as difficult, even if some days that number feels much larger.

How to handle difficult people

The other day I was standing behind a guy dressed in a tan suit at a coffee shop close to our Jotform offices.

He was on his phone while simultaneously rambling off a complex drink order. Between the mumbles at the barista and the chatter into his wireless earbuds, I think all of us waiting in line knew what was going to happen next.

At the end of the bar, he picks up his coffee, takes a sip and immediately loses it over ‘the extra foam’ now destined to ruin his day.

Unkind words were exploded across the counter, leaving the barista temporarily frozen.

A Tank, confrontational and angry, was on the loose and he might be bloated later.

I watched as the barista listened to what he said, put his head down and redelivered the order to the man in just a few moments.

He handed the cup over kindly, watched for his approval, nodded, and then went to his next order as the man walked out the door still talking on his phone.

The barista had gotten what he wanted.

He kept his goal in mind and by listening and then taking action in the face of verbal accosting — he got him to leave — which was his exact desire.

How do we get what we want despite the “difficults”?

Whether you’re communicating with any difficult personality, being in the moment with challenging people is hard.

At Jotform, we have over 10 million users and some of our difficult users give us a difficult time almost every single day.

I wanted to put together a few guidelines I use that help me diffuse situations from handling our customer relations and also from managing our team of over 300 employees.

5.1. Listen and understand the end goal

At first, the barista froze to avoid conflict, but we’re all hard-wired like that.

Every last one of our brains still defaults to fight-flight-freeze when something highly stressful or unsettling occurs. However, when a person is acting unreasonably right in front of you — being like the barista works perfectly.

He was able to not only move through this automatic response of fight-flight-freeze, but get clear on what he wanted and execute flawlessly.

Listening combined with intent to understand what is being sought, gives you the prime opportunity to end the interaction while achieving your goals.

The barista understood that no matter what the man said what he really wanted was to have his coffee the way he asked for it.

He listened past all the yelling to delineate how he could fix the situation while achieving his goal of watching him walk out the door. The feedback was harsh but this barista was a pro.

Now, we don’t hear much yelling at Jotform but we get challenging feedback online all the same.

Our forms are meant to help us and our customers meet their goals and mitigate these issues before they happen. However, difficult people show up in person and online to air their grievances.

5.2. Focus on what you can do something about

You may not be able to avoid what difficult people have to say but you have control over what you do, and more importantly, what you ask.

Asking questions puts you in the driver seat to let them air what they have to say while guiding them to what you can do anything about.

Difficult people, especially what Dr. Brinkman and Dr. Kirschner referred to as “whiners”, require a lot of directed questioning in order to come to understand their desires and what actions are available to you.

On the flip side, during this intense questioning, you may end up uncovering something about yourself you wouldn’t have known otherwise.

We decided to test this process this year by conducting face-to-face interviews with our users.

In one of our first interviews, we came up close and personal with the ‘whiner.’ They drained our time, providing vague descriptions while sprinkling it with unpleasant commentary.

We didn’t give up, we kept digging, always having in mind our goal of how we could create a better product.

An hour later, we struck gold. We found out this customer had been using Jotform as a productivity tool.

Jotform Cards

Customer after customer shared similar tales as our interviews continued over the following weeks.

By continually asking deeper questions of a difficult customer and not giving up, we not only found a new focus in 2018, we discovered the difference between challenging people and unpleasant comments.

5.3. Get clear between a difficult message and a difficult person

Earlier this year, a customer made several new feature requests and was pretty adamant about their unhappiness with our functionality in a support thread comment.

Good news: they felt comfortable enough to let us know where we didn’t meet their expectations.

Bad news: YIKES.

I didn’t take the grievances shared on our forum personally. I did, however, take it seriously.

I don’t usually jump into support discussions, but this was a critical moment to examine whether this person was being difficult, or giving us an opportunity for improvement.

Further, what if by challenging our platform and strategies, this customer was giving us a huge gift?

I needed to find out.

I saw this as an opportunity and stepped into the forum to respond to the customer’s experience. I provided details on what was going on with the platform that could be causing their issues and also offered my email address for further discussion.

It always helps to get clear between a difficult message and a difficult person.

What couldn’t be seen on the thread was we listening to their issues and ascertaining their end goals through deep diving questions.

Final words

You will always come across challenging people but by listening to them, asking questions, understanding their goal and focusing your actions, you can put ourself in the best position to succeed in getting what we want.

It won’t always happen in the most pleasant way, but keeping these guidelines in mind helped us handle challenging moments both with our users and within our organization, and hopefully they’ll help you grow, too.

So, don’t freeze and walk away but instead engage head-on with these personalities.

They will push you to innovate, make things better and fill in gaps you didn’t know were there before they arrived.

And I’d say that’s a gift worth getting at the expense of an uncomfortable confrontation, wouldn’t you?

Skill 6: Learn to disagree the right way

In 1956, a British doctor named Alice Stewart made an alarming discovery. Pregnant women who were exposed to X-rays, she found, were more likely to have children who would die from cancer.

Thomas Barwick | Getty Images

We know now that the radiation from X-rays is indeed harmful. But at the time, Stewart’s finding flew in the face of the accepted narrative about X-rays—that they were the paragon of modern scientific achievement, and that their use would improve lives, not harm them. 

Stewart published her findings, expecting a massive buzz. Instead, nothing happened. So set were the minds of the medical establishment that they dismissed Stewart’s assertion as unsound. But Stewart didn’t give up. Instead, she collaborated with a statistician named George Kneale, who said his job, simply, was “to prove Dr. Stewart wrong.”  In her 2012 TED Talk, Margaret Heffernan said of Kneale that,

“He actively sought disconfirmation. Different ways of looking at her models, at her statistics, different ways of crunching the data in order to disprove her. He saw his job as creating conflict around her theories. Because it was only by not being able to prove that she was wrong, that George could give Alice the confidence she needed to know that she was right.”

We often want to avoid disagreements because they can be messy and painful. But for a business to be truly successful, they’re absolutely necessary. Stewart allowed her theory to be stress-tested by someone intent on proving her wrong, and in doing so, changed the status quo (and saved countless lives in the process). Below, I explore how to foster an environment that welcomes debate, rather than discourages it. 

6.1. Create a safe atmosphere for disagreement 

According to one Survey Monkey study, only 58 percent of women and 68 percent of men said they felt they could express a dissenting opinion at work without negative consequences. That’s a lot of missed opportunity for potential growth. 

Of course, there is a time and place to disagree. The middle of a meeting with investors might not be the optimal time to tell your co-founder that you think her idea for the re-brand is garbage. 

Instead, be intentional about your forum. Consider establishing regular sit-downs where frank conversation is expected, and limit the scope and time to avoid getting off topic. Feedback should be constructive and non-emotional, without any tolerance for personal attacks. Remember, people are more receptive to criticism and debate when it’s factual and rooted in relevant examples. 

While it’s tempting to think that a lack of disagreements is the sign of a healthy workplace, the opposite is true. As Harvard Business Review contributor Liane Davey wrote, “If you think you’re ‘taking one for the team’ by not rocking the boat, you’re deluding yourself.”

“Teams need conflict to function effectively,” she says. “Conflict allows the team to come to terms with difficult situations, to synthesize diverse perspectives, and to make sure solutions are well thought-out.” Conflict may not be pleasant, but it is the source of true innovation. 

6.2. Be willing to change your mind 

Laying the groundwork for constructive debate really only works if everyone involved is open to having their minds changed. 

This isn’t always easy. Knowing this, PhD. Jim Stone laid out five steps to having a truly open-minded debate. 

The first two steps are to recognize our common humanity, and try to learn the story of how someone arrived at their viewpoint. "By default we tend to see a person who has different views as an opponent. And we fall into a 'debate' frame with them," Stone writes. Instead, try thinking in terms of what’s called a “dialogue frame,” which emphasizes what we have in common, rather than what we don’t. The second step builds on the first, allowing you to put yourself in the other person’s shoes. 

Next, make sure everyone involved feels safe rethinking their argument. “If you want the other person to open their mind, you have to make them feel safe doing so,” writes Stone. One of the best ways to do this is to establish outright that a change of heart is okay, saying something like, “I want to feel free to take things back if they don't hold up. And, of course, I'll give you permission to do that, too."

The fourth step is validating the other person’s experience so that they feel understood, which means not undermining or questioning whether they really feel how they say they do. That said, it’s totally possible — and often necessary — to validate while pushing back against their interpretation. 

The fifth and final step is never losing sight of the goal of the conversation. If you need to speak up to someone in a position of power, like a supervisor or investor, for example, make it clear that your objective, like theirs, is simply to advance the company’s mission.

6.3. Ask others their opinions 

Not all dissent is created equal. Surrounding yourself with experts and critical thinkers—especially those who think differently than you—will give you the chance to put your ideas to the test. Besides, asking the opinions of those around you shows trust and admiration of expertise, and people who ask for help are perceived as more competent than those who don’t. 

As Heffernan says in her talk, seeking out diverse opinions forces us to “resist the neurobiological drive, which means that we really prefer people mostly like ourselves.” 

It means we have to seek out people with different backgrounds, different disciplines, different ways of thinking and different experience, and find ways to engage with them,” she says. “That requires a lot of patience and a lot of energy.

6.4. Be intellectually honest

As the head of my startup, I may believe that I am right—but unless I can build consensus among my team, that often doesn’t matter. 

Being intellectually honest means striving for the truth, whether or not it jibes with your beliefs. In business, this means that decisions are rooted in facts, not by the position of the individual presenting it, writes Perry Tam, the co-founder of Storm8. 

“Truly great companies foster a culture of innovation, which is driven by collaboration and the ability to embrace change,” he writes. “The best companies have employees and leaders who have the curiosity to learn and improve—and an innate desire to discover a better and more efficient way of doing things.”

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