𝗕𝗼𝗮𝗿𝗱𝘀: 𝗘𝗹𝗲𝘃𝗮𝘁𝗲 𝗬𝗼𝘂𝗿 𝗘𝗻𝗴𝗮𝗴𝗲𝗺𝗲𝗻𝘁
- Benjamin
- Jul 23
- 9 min read
Updated: 4 days ago

Tobias'* father worked as an accountant and his mother as a librarian. From a young age, Tobias found solace in tinkering with computers and playing video games, often losing himself for hours in ways to optimize his setup to improve the gaming experience. While he excelled academically, he always felt out of place in social gatherings.
After college, Tobias joined a large tech firm which relied on gamification to increase customer engagement. He was valued for his development skills but overlooked in meetings. He became quietly frustrated with the sense that his ideas never got a fair hearing.
He wanted to create a space where he could explore his ideas around customer engagement, where thoughtful people like him could thrive, and where the best ideas—not the loudest voices—would shape the future.
Quick, initial success for his AI workflow startup led Tobias to raise money so he could increase development resources as well as spend on sales and marketing. After raising seed funding, he formed a board with two seasoned investors and a technical advisor who had mentored him.
A month later, Tobias faced his first formal board meeting. He dreaded the prospect of the meeting becoming adversarial and being (once again) drowned out by sharper, louder voices. He needed to find a way to make these meetings productive and collaborative, while staying true to his quiet, methodical nature.
At the advice of the technical advisor, Tobias scheduled one-on-one calls with each board member before the meeting. He asked about their goals, communication styles, and what they hoped to see. In each meeting, he explained his own approach: “I think best when I can reflect, so I’ll share materials in advance and welcome your questions before we meet. With major decisions, I want to hear everyone’s feedback, but may ask for time before making any decisions.”
Tobias used these conversations to align expectations. He learned that one board member was anxious about the company’s burn rate, while another wanted to discuss technical milestones. He adjusted the agenda to address these points directly and invited board members to send feedback on the deck ahead of time.
For the meeting, everything went as planned except one time. A product delay caused some debate. Tobias acknowledged the concern, summarized the differing viewpoints, and suggested a smaller group of him, the technical lead, and the concerned investor.
Since this was their first board meeting together, Tobias sought feedback. One investor commented, “This is the most effective board session I’ve attended in months.” The other offered that the meeting was different than most, but highly productive, and he was willing to adapt. Everyone mentioned that their contributions and next steps were clear.
Constructing Your Ideal Board Meeting
“If your cofounder is like a spouse,
then board members are like your in-laws.
You will see them regularly, they are hard to get rid of,
and they have an enormous impact on your company’s future.”
– Elad Gil
Board meetings can be a source of anxiety for many founders, regardless of personality type. Exposing your hard work to the scrutiny of people you respect can be stressful.
Board meetings may feel like an arena for extroverted performance. However, this post will encourage you to structure the time productively, prepare thoroughly, and leverage your natural strengths (deep thinking, careful listening, and thoughtful reflection).
This section covers the logistics of board meeting preparation, helping you create more meaningful interactions and maximize your time together.
Know Your Audience
Schedule one-on-one meetings with investors to get to know them on a deeper level. These low-pressure settings let you understand their perspectives, concerns, and what they want to know about the company and its challenges. Many topics from these initial conversations will come up again in group meetings, so you will know better what to expect.
Build personal connections, too. People naturally want to help those they like and relate to, and you'll often discover shared interests when you take the time to look.
Every investor can bring value beyond funding. They can connect you with key hires, partners, vendors, and potential clients. Some excel at refining business plans, financial models, or value propositions, while others provide invaluable advice and referrals during future funding rounds.
Discuss communication preferences early: ask board members how and when they prefer to be contacted, what information they need, and which situations require immediate attention. Understanding how they handle anger and deliver critical feedback helps prevent future tensions and allows you to find workable compromises. Also, offer your preferences for communication.
Finally, beware of investors who offer only positive feedback. It’s like eating chocolate—it definitely makes you feel good at the moment, but it’s unhealthy as a diet. Actively seek critical feedback.
You may explain that you can develop as a leader only by being pushed by people you respect, the same way that professional athletes, artists, and other leaders need coaches, mentors, and trainers to reach their peak performance.
While you won't act on every piece of advice, you should appreciate board members who offer constructive criticism. To reinforce what you want, you may offer an example of when someone told you uncomfortable feedback that you later appreciated, and you may insist that feedback is important to you to build a productive, long-term relationship.
"My best successes came on the heels of failures,
because I learned from them.
You need people who will tell you the truth,
not just what you want to hear."
— Howard Schultz
Prepare for the Meeting
Presentation. Consider these tips for building an effective presentation:
Avoid the temptation to give too much information. Less is more.
Keep your deck succinct so the board easily finds the essential information.
Link to supporting materials (collateral, demos, financial reports) for additional context.
Cover accomplishments, activities, plans, and expected outcomes. Rather than viewing this as bragging, treat it as an opportunity to share learning experiences.
Include meaningful visuals: charts, diagrams, and relevant images.
Offer real examples of lives impacted where possible to remind investors why they got involved initially.
Organization. Create a schedule that allows for plenty of time to cover the key issues. Block out time for yourself to think and relax before the meeting. You can also block time after the meeting to decompress. Recognize if you need to schedule a break during long sessions.
Communicating. Consult with attendees about their priority topics and metrics. When building the agenda, focus on two to four key issues to encourage meaningful discussion. Share KPIs and reports ahead of time and invite questions beforehand, allowing your meeting time to focus on larger themes.
"Board meetings should not be for the benefit of the board.
They should be for the benefit of the CEO and the senior team."
– Fred Wilson
Preparation. Help members prepare for each main topic with specific prompts. For instance, "Here are the options I've identified based on the information below. What alternatives would you suggest?" or "Please review these proposed product features and wireframes before we meet so we can focus our discussion on questions and opportunities."
Nemawashi
When approaching the board with critical issues, major projects, strategic pivots, or controversial decisions, consider using nemawashi.
Nemawashi is a consensus-building process that may be perfect for introverted leaders in some cases, especially with large projects, pivots, and controversial decisions.
While Western business cultures typically conduct open debate and decision-making during meetings, in Japan, key decisions are made through nemawashi before the official meeting, which then serves to formalize the agreed-upon consensus.
The process involves holding one-on-one or small group discussions with stakeholders before a formal meeting. The term literally means "preparing the roots" (as in preparing a tree for transplant), but in business, it refers to "laying the groundwork" for a proposal or group decision.
How nemawashi works:
Informal Discussions. The person proposing a change meets individually or in small groups with each member of the decision-making team and those affected by the decision.
Gathering Input. Through these discussions, the proposer collects feedback, addresses concerns, and refines the proposal.
Building Consensus. By the formal meeting, most objections have been resolved, and participants are aligned, making the meeting move along more smoothly.
In Japan, this approach prevents public disagreement or "loss of face" during group meetings, which is a cultural priority. For introverts, this process offers an effective way to guide meetings toward progress and tackle major challenges. It also encourages everyone's participation, including those who might hesitate to speak up in larger groups.
In the Meeting
Format. Focus the meeting on discussing major opportunities and challenges. Here's a suggested agenda:
Major accomplishments and challenges since the last meeting
Performance and KPIs (sent beforehand with a chance to answer any questions)
Strategic topic 1
Break and return with exercise (discussed below)
Strategic topic 2
Board decisions (e.g., granting options and compensation changes)
Levity. Include an engaging exercise that helps attendees connect and learn about each other or your company. This activity can ease tension and strengthen relationships.
Consider discussing your favorite cities, highlights from the past year, or personal role models. Make sure to pick a topic that will authentically interest you since the point is not to add a new layer of stress.
Collaborate. Treat all attendees as equal contributors to the meeting's success. While some may have more experience or achievements, everyone is working toward the same goal: finding the best solutions for the company. Use one-on-one discussions to share others' perspectives on this approach.
You may also offer an example of when someone unexpectedly provided you with useful insight to confirm that everyone can have useful ideas.
Engagement. If some Board members are quiet, draw them out. Consider using structured turn-taking or "round-the-room" discussions to ensure full participation. Also, encourage members to give you options, not simply answers.
For instance, instead of “What should I do?” ask: “How have you seen other founders handle this issue?” or “What are my options here?”
Tension. When differences arise, remember that some tension can be productive if it serves group collaboration rather than individual dominance. Monitor the discussion with two key points in mind.
First, ensure your opinion is being heard and respected. You can acknowledge the emotions and concerns, remind everyone that your time is limited and valuable, and insist you want these meetings to concentrate on growth and risk management.
Second, check whether the discussion is moving forward or going in circles. If it's the latter, I firmly suggest pausing the debate. You may suggest a smaller group develop recommendations to share in the next meeting or apply nemawashi (above) for you to propose the best solution.
After the Meeting
Improvement. Right after the meeting, while it's fresh in your mind, make notes about ways to improve communication and delivery. Also, list accomplishments from the meeting, whether new insights or ways you effectively conveyed information and managed everyone’s time together.
Communicate your positive observations about others, such as the team's preparation and accomplishments, as well as board members' ideas and recommendations. Your gratitude reinforces the right behavior and shows that you appreciate their help.
Following up. Embrace written or asynchronous communication for the next steps and clarifications. Capture the major decisions, ideas, next steps, and those responsible for future progress. Send these notes within two business days.
Feedback. Ask attendees for their impressions and pose the question, "What is one way the meeting could be better next time?" Creating an environment that welcomes honest feedback is particularly important during your first few meetings and with new attendees.
Sharing. Present the deck and key insights from the board meeting with your team to keep them informed. This communication helps the team understand the company’s direction, make well-informed decisions, and contribute ideas for growth, efficiency, and recruitment.
Crisis. Don't wait for the next meeting if an urgent issue arises. Reach out to investors for their perspectives and recommendations for addressing the issue. It's natural to feel anxious about discussing major problems. However, remember that most investors have seen dozens of crises directly or through their peers. They can typically maintain objectivity and offer support during challenging times.
Key Takeaway: Don't feel pressured to put on a show or become more extroverted. Instead, focus on being the most effective version of yourself as a leader, someone who is prepared, clear, and passionate about your company's future.
How Can I Keep Learning? From the strategies discussed above, choose one or two to implement in your next board meeting. If you haven't formed a board yet, determine how to best apply these principles when running leadership team or advisor meetings.
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* Tobias’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.
I wrote this post with AI editing.
What if the quietest person in the room is the one that changes the world?
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