𝗕𝗲𝘆𝗼𝗻𝗱 𝗦𝗺𝗮𝗹𝗹 𝗧𝗮𝗹𝗸: 𝗛𝗼𝘄 𝗗𝗲𝗲𝗽𝗲𝗿 𝗖𝗼𝗻𝘃𝗲𝗿𝘀𝗮𝘁𝗶𝗼𝗻𝘀 𝗗𝗿𝗶𝘃𝗲 𝗚𝗿𝗼𝘄𝘁𝗵

Evan* is a quiet and introspective entrepreneur who feels at odds with the fast-paced, extroverted world of startups. Growing up, he was fascinated by video games—first playing them for countless hours, then creating them. He spent hours alone coding and solving complex problems.

At age 14, his mother was diagnosed with pancreatic cancer. It spread quickly, and she passed away within a year. He was struck by both the disease's aggressive nature and the compassionate doctors and nurses who took the time to comfort his mother. Her best days followed the right treatment and consideration.

Devastated, Evan immersed himself in studying biology at school and home. As a high school senior, he presented scientific papers at three national science fairs, earning second place at one fair for demonstrating how technology and human care can work together to improve patient outcomes. In college, he double-majored in computer science and biology. After graduating, Evan wrestled with choosing between medical school (the desired path from most of his family) and starting a company (where his head landed every night). His aunt—his mother's only sister—told him his mother would want him to pursue his passion.

Evan's startup, HealthMind, developed AI-powered tools with an intuitive interface for patients, practitioners, and administrators. The platform streamlined administrative tasks while providing clear insights into treatment plans and self-care methods. Users valued how it translated complex medical and insurance terminology into straightforward terms and actionable steps.

However, as the company grew, Evan faced a significant challenge: effectively communicating his vision and progress to stakeholders, including investors, team members, and potential clients. He struggled to convey ideas clearly and confidently, often feeling overwhelmed by the pressure to be more outgoing and charismatic, especially when meeting people as part of larger groups. He wondered if others thought he was incompetent, which only increased his anxiety.

After checking with his team, other founders, and several investors, Evan decided to leverage his strengths by focusing on written communication and hiring a writing coach skilled at conveying ideas simply. Before meetings and discussions, he would prepare clear notes, describe his objectives, and prepare a couple of solid questions.

Evan also implemented weekly small-group sessions where everyone could share their thoughts openly. These meetings, which were limited to five people, gave him valuable input and opportunities to practice communication. This shift transformed group meetings from anxiety-inducing discussions of countless topics into focused sessions exploring one or two strategic plans.

HealthMind's innovative AI tools began making a tangible impact in the healthcare sector, earning recognition and respect from industry leaders. The team applied their small-group approach to focus groups with existing and potential clients, using their feedback to improve their process and the product.

Evan's journey taught him a valuable lesson: success in entrepreneurship isn't about conforming to others' expectations of being outgoing and charismatic. Instead, it's about embracing your authentic self and using your natural strengths to build a team and create systems that amplify your abilities. He already enjoyed meaningful conversations, and through effective preparation, he could foster many more.

Why Improve Communication?

As an introvert, I envy the image of Ralph Waldo Emerson writing by his isolated pond.

Yet effective communication is essential when working with various and numerous stakeholders. Strong communication enhances problem-solving, sparks new ideas, builds community, and reduces risks.

“Good communication is the bridge

between confusion and clarity.”

– Nat Turner

As you strive to build product-market fit, scale your operations, and grow your business, you'll interact with many people, including your team, investors, customers, vendors, and others. Your ability to work effectively with them will accelerate your growth.

Clear communication helps stakeholders understand and support your direction. Here's why:

• Collaboration. Sharing wins and lessons learned builds momentum. When you discuss goals and mutual interests openly, you encourage others to match your candor, thus encouraging valuable insights and preventing future problems.

  
  

• Learning. Explaining your objectives reinforces your own understanding since teaching is a powerful way to learn. Through discussion, you may also uncover potential flaws in your thinking.

  
  

• Community. Fostering a group that loves your business is the fastest path to growth. This community-building requires clearly communicating your vision and how to achieve it, even when facing perceived skepticism and real problems.

  
  

• Prevention. Building relationships helps to discourage misunderstandings. Confusion can cause problems. Once, I wrote a lengthy email but omitted the word "not" in one sentence. This error led to a week-long misunderstanding, during which someone thought I was unhappy with their performance and complained to others. I could see how reading that one line was confusing. Fortunately, we eventually talked it through.

“Effective teamwork begins and

ends with communication.”

– Mike Krzyzewski

Start the Conversation

Here are some effective ways to build better communication with people you are meeting for the first time. These guidelines help create a foundation for interaction, reducing nervousness and allowing you to focus more on the other person.

• Discover mutual interests

• Ask many questions

• Apply a unique approach

• Amplify your audience

• Create a feedback loop

Discover Mutual Interests

Effective communication conveys a sense of alignment. While business decisions are driven by value, price, and personal interest, they work best when all parties share a clear connection to the brand and vision.

Listening, empathizing, and understanding are vital—they help you better connect your vision with others' needs. Ask people questions about their history, interests, and hobbies. Try to ask three different questions and then follow up, which will we'll discuss next.

Ask More Questions

Many conversations resemble tennis matches, where each person volleys a question, gets an answer, and then asks another question. Often, the second question is about a new topic, even if their last response almost begs for a follow-up question.

Instead, do your best to follow up three times on what someone says. Here’s an example.

You: Did you see the latest film, ____?

Them: No, I don’t really care for that type of movie

You: Oh, what type of films do you like?

Them: Answers

You: What was your favorite film in the ___ genre?

Them: Answers

You: Why did you like it so much?

Them: Answers

The last answer may reveal something interesting about their interests, much more than the first couple of questions.

The last few are open-ended questions, where someone has to respond with more than Yes/No. Pose open-ended questions as much as possible to keep the conversation moving.

Know Your Audience

There are different paths to connect with others as everyone comes to a conversation from various backgrounds and experiences.

I learned this lesson when I got into trouble by using the same communication style with different stakeholders. While working at a fast-growing ecommerce company in New York City, where most employees worked in the office, I became accustomed to the local style of communication—clear and firm, with a touch of humor that New Yorkers find jocular but others might consider rough.

When a large Midwestern firm acquired our company, I maintained my communication style during visits from their leadership team, delivering direct answers with my usual edge. Our CEO later informed me that this approach wasn't well-received. He shared that he had needed to adjust his communication style with them and advised me to do the same. This revelation became an unexpected but valuable lesson.

When engaging with your stakeholders, you should consider carefully what information they need, how often they need to receive it, and which format will be most effective. This thoughtful approach will foster stronger connections and lead to more productive responses.

Amplify Your Audience

A passionate, positive community is crucial for exponential growth. These supporters will attract new customers, promote your business, and drive referrals. Help them understand your growth plans and how they can contribute to your company's success.

As a founder, make an effort to align your conversations with your objectives, especially at company meetings, demonstrations, and conferences. For example, when Evan from HealthMind (story at the beginning of the chapter) attends conferences, he may ask attendees about their views on the health tech market's direction and the most impressive solutions they've seen in the past year. Their responses allow him to discuss HealthMind, gather feedback, and identify potential referrals.

Create a Feedback Loop

The best way to improve any skill is through honest, constructive feedback.

Seek specific feedback about your communication style and approach. Try questions like, "How could I have led that meeting more effectively?" or “What question were you expecting me to ask but I didn’t?”

When a person doesn't understand what you're explaining, switch to another approach, such as giving a quick demo or letting them play with the product for a couple of days. These approaches help visual and hands-on learners, respectively.

Finally, don’t be discouraged if your communication is not improving. Instead, consider another approach—asking a team member to help you practice, working with a coach, or joining a group like Toastmasters to develop your skills.

Level Up the Discussion

You can focus on deepening relationships with open-ended questions that encourage vulnerability and deepen relationships.

“Communication is the real work of leadership.”

— Nitin Nohria 

While these questions are meant for existing working relationships, you may get more comfortable using them with new people too.

Here are questions that lead to great conversations:

• What's the most important thing I should know about you?

• What excites you right now? 

• What is something incredible about you that even some of your friends don't realize?

• What’s the best thing that happened to you last/this year?    

• What’s a challenge you’re wrestling with?

• What makes you smile when you get up in the morning? 

You should be prepared to match their vulnerability or risk more in the interest of building a more meaningful connection and getting advice.

These questions should delight your conversation partners, who are equally eager to move beyond small talk. Keep in mind that some people may shy away from deeper conversations, so read the room and adjust accordingly.

Business Growth

When relationships move beyond surface-level exchanges, they become the foundation for trust and loyalty—essential ingredients for business growth.

Through deeper conversations, people truly understand each other's values, motivations, and challenges, reinforcing their connections. This connection creates stronger bonds which foster partnership and shared purpose. In business, this means gaining valuable customers, partners, investors, and other stakeholders. These bonds also encourage effective collaboration in teams so people become more willing to share ideas, take risks, and support each other's success.

Ultimately, businesses that prioritize authentic, meaningful dialogue set themselves apart by building on a foundation of growth, loyalty, and lasting impact.

Key Takeaway: Introverted founders may struggle to convey their vision and progress to stakeholders, especially in meetings. By embracing their natural strengths and adopting new strategies, introverts can cultivate strong relationships and foster business growth.

How Can I Keep Learning? List two or three of your communication strengths and one area for improvement. Then, develop an action plan that both leverages your existing strengths and reaches out to at least one person for help.

* Evan's story is a fictional account inspired by various people and situations I've encountered over the years. It was created to provide another perspective on this topic.

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Build Scale Grow solves problems for fast-growing startups, specializing in Social Impact, EdTech, and Health Tech and focusing on Introverted Founders.

I wrote this post with AI editing. Photo by Helena Lopes.

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