𝗜𝗻𝘃𝗶𝘀𝗶𝗯𝗹𝗲 𝗕𝗮𝗿𝗿𝗶𝗲𝗿𝘀: 𝗛𝗼𝘄 𝘁𝗼 𝗢𝘃𝗲𝗿𝗰𝗼𝗺𝗲 𝗛𝗶𝗱𝗱𝗲𝗻 𝗢𝗯𝘀𝘁𝗮𝗰𝗹𝗲𝘀

Two Tales of Two Startups

I once worked as head of operations at a digital marketing company. During the digital marketing boom, they built online branding solutions for several notable Fortune 500 companies and were poised to grow immensely.

Starting with just $5,000, in just five years, they grew the company to $3M in annual revenue. Aiming to reach $10M, they hired seven senior leaders to help with the transition. Each leader brought at least a decade of deep expertise in their respective areas.

Soon, these leaders presented new ideas for growth. They proposed changes to marketing, branding, and the business model, plus an employee incentive plan tied to ambitious targets. The founders rejected all these proposals without meaningful feedback. Within two years, all the directors had left, and the company shut down 18 months after that.

While ingenuity, perseverance, and meticulous attention to detail had helped the founders reach $3M, they couldn't see how their rigid leadership style was stalling growth—ultimately leading to the company's demise. They could have either maintained their existing size without hiring senior directors and had a nice lifestyle business or adapted their leadership approach to align with their ambitious goals.

Contrast this experience with my first startup, an e-commerce company that streamlined bill payments. The value proposition resonated strongly with both clients and their customers, leading to annual doublings in revenue and headcount.

I joined as employee number 32. When the team grew beyond 100 people, the founders recognized the need to shift their leadership style. Instead of weighing in on every decision, they learned to delegate and trust their leadership team's problem-solving abilities. Though visibly tempted to jump in, they held back, knowing the leadership team needed to develop these capabilities independently. They offered guidance when asked but deliberately stayed out of routine discussions to avoid hampering their leaders' growth.

My role shifted dramatically from head of business operations one year to client relations the next and then to director of payment processing the third year. The founders could see my transferrable skills (organization, communication, and project management) as more critical than industry experience. My situation also applied to other leaders there as they grew into new roles and responsibilities to keep the company moving forward quickly.

With a versatile leadership team supported by the founders, the company thrived by expanding its offerings, entering new industries, and streamlining implementation. Their success culminated in a rewarding acquisition by First Data Corporation.

Addressing Blind Spots

Blind spots are cognitive biases, unrecognized weaknesses, or overlooked areas in the business. They can stem from internal factors, like limited knowledge or experience, or external factors, such as shifting market trends or technological advances.

When left unchecked, blind spots can hinder growth, lead to poor decisions, and increase the risk of business setbacks—especially during periods of company growth.

For introverted founders, recognizing and addressing blind spots is crucial for maintaining a competitive edge and ensuring lasting success. These founders often encounter anxiety and hesitation in unique ways. When surrounded by extroverted leaders, investors, or peers, they might question whether their approach is wrong.

"To be yourself in a world that is constantly

trying to make you something else

is the greatest accomplishment."

— Ralph Waldo Emerson

The key is distinguishing between an approach that is different and one that is ineffective.

Challenges for Introverts

Consider these potential blind spots and how they may affect you and your business.

Self-Promotion: Introverts often struggle with self-promotion. This struggle can lead them to underestimate their achievements and receive less recognition from potential talent, customers, and investors.

Feedback: While introverts may hesitate to seek input, doing so is essential for growth. There's a clear distinction between natural introversion and recognizing when interaction is necessary for valuable input.

Decision-Making: Introverts typically take a reflective approach to deciding. While this thoughtfulness can be an asset, it may lead to overthinking and delayed decisions.

Strategies for Identifying Blind Spots

It's nearly impossible to "see what we can't see." The following approaches will help you seek different perspectives and recognize your blind spots.

Ask the Hard Questions: Gather feedback from diverse sources, including team members, investors, and customers. Seek out people with varied skills, work backgrounds, and across generations. Ask each person to share one strength they see in you and one area for improvement. This balanced approach demonstrates openness to both praise and constructive feedback. If someone seems hesitant to offer criticism, share a story about how past feedback helped you grow.

Mentors or Coaches: These people should know you and your business well and be willing to provide candid, critical feedback for your development. Balance your initial questions between specific challenges, like managing employee issues, and broader strategic concerns, such as identifying new markets. Since most professionals specialize in either tactical or strategic guidance, adjust your future questions based on their initial responses.

Continuous Learning: Attend conferences, take courses, and conduct research to stay alert to new blind spots as your business evolves. Keep an open mind to new ideas instead of dismissing them outright. Reading fiction can offer fresh perspectives by showing familiar scenarios through unexpected lenses and allowing you to consider new possibilities unencumbered by the current reality.

As your company gains traction, embracing new ideas becomes more challenging. More and more people will assume you have everything figured out. Yet, making time for learning remains crucial at every stage of growth since successful businesses continually evolve.

Key Takeaway: While introverts possess valuable strengths like deep listening and thoughtful decision-making, these traits can obscure their view of other essential startup leadership behaviors. Identifying and addressing blind spots is crucial for success.

How Can I Keep Learning? Try one of the "Strategies for Identifying Blind Spots" listed above in the next two weeks to discover potential insights. Besides potentially learning something new about yourself, this effort shows others your willingness to learn, which could be valuable as they approach you later on with useful ideas and observations.

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90% of startups fail. 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 Amine M'siouri who can be found here.

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