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Guidelines for Startup CEOs working effectively with their Board of Directors

1. Never surprise the BOD or Advisors with bad news. If something breaks, do not wait for the board meeting.
Call each board member individually. Explain what happened and your plan to solve it.  Own the situation.
On the other hand, it’s ok to surprise the BOD with good news – and get their feedback on how to further build the business from it.
Realize, trust grows when there are little or no surprises – and evaporates when a major issue, cost, loss, or risk occurs that wasn’t anticipated.  

2. Be very thoughtful and insightful. And never be defensive. 
Since good board members are trying to help, recognize their feedback comes from a good place and you have an opportunity to fast-track learning from their experiences.
When people try to help and the response is defensiveness a pernicious cycle starts. Don’t let this slippering slope happen.  
To address challenging situations, be open to ideas and to criticism. Be creative / innovative. Really think about them.
Be a very good listener and open your mind to their suggestions.  
And to help the cause, be good at asking questions to demonstrate your insight and seriousness to get past the challenge(s).

3. While you may not have to implement their suggestions or do what they say,  you must think very carefully about them.
Plus demonstrate a thorough understanding of the situation, strong look ahead, the ability to effectively communicate at different levels, etc.   
Your obligation is to listen carefully and think thoroughly. Then do what you think best.
If their idea is better than yours, do it. If it is not, explain why.
And, show them how you thought about it and how you used their ideas to sharpen your thinking.  
It is unusual for a board member to know your business better than you do. You and your team live it every day.
The board brings context, pattern matching, wisdom and governance…  
Your job, as CEO, is to lead.

Why is effective CEO / BOD collaboration important ?

To improve the probability of venture success by being good at  –

  1. leveraging different and complimenting competencies for advantage
  2. perceiving and managing risk
  3. creating new value – for Customers and the business
  4. getting market traction / ramping sales
  5. stakeholders becoming more sophisticated in business, strategic thinking, achieving superior outcomes, monetizing value creation, etc.

Given the potential of startups to create significant new opportunities and wealth – it’s essential the CEO collaborate effectively with their BOD (as indicated above).  

March 3, 2026  –  CAIL Venture Investing Commentary    info@cail.com    www.cail.com    905-940-9000