The Kitchen Cabinet Advisory Board
Assemble 3-5 trusted advisors who will tell you what they really think, not what you want to hear
Galloway advocates assembling a personal advisory board of trusted people who know you well and are willing to give you honest, sometimes uncomfortable feedback. The greatest value of your kitchen cabinet is not their recommended course of action but the questions they ask, which pressure-test your reasoning. Their primary virtue is that they are not you. As Galloway puts it, it is difficult to read the label from inside the bottle. This becomes increasingly critical as you gain wealth and power, because fewer people will reliably tell you what they really think.
- The most valuable advisors are those who will tell you what they actually think, not what you want to hear.
- It is difficult to read the label from inside the bottle, so outside perspective is structurally necessary.
- The questions advisors ask pressure-test your reasoning more than the conclusions they hand you.
- Wealth and power systematically reduce honest feedback, making trusted external voices more critical over time.
- A small group of people who know you well beats a large network of people who know you superficially.
- Identify 3-5 people with relevant experience and willingness to be honestLook for people who have depth of experience, know you personally, and have demonstrated willingness to disagree with you. They do not need to be in your industry. Diversity of perspective is the primary virtue. Prioritize people who have told you uncomfortable truths in the past.
- Formalize the relationship with explicit asksDo not keep the advisory relationship vague. Tell each person explicitly that you value their perspective and want to periodically run decisions by them. Set a cadence for check-ins. The formality signals that you take their input seriously and creates mutual accountability.
- Use the cabinet to pressure-test decisions, not make them for youBring specific decisions or dilemmas to your advisors. Present your reasoning and intended course of action, then listen to the questions they ask more than the answers they give. The goal is to identify blind spots in your thinking, not to outsource the decision.
- Specifically use the cabinet for quit-or-persist decisionsGalloway emphasizes that knowing when to quit is an art. Your kitchen cabinet is invaluable for distinguishing between difficulty that can be overcome (persist) and gravity problems that cannot (quit). They can see patterns in your situation that you cannot see from inside it.
Galloway founded Red Envelope, an e-commerce company, in 1997. It failed slowly over ten years, consuming the majority of his net worth. In contrast, his next venture Brand Farm recognized within six months that the concept no longer made sense after the dot-com bust, shut down the parent business, and everyone moved on. He explicitly identifies knowing when to quit as a skill his kitchen cabinet could have sharpened earlier.
Galloway advocates assembling a personal advisory board of trusted people who know you well and are willing to give you honest, sometimes uncomfortable feedback. The greatest value of your kitchen cabinet is not their recommended course of action but the questions they ask, which pressure-test your reasoning. Their primary virtue is that they are not you. As Galloway puts it, it is difficult to read the label from inside the bottle. This becomes increasingly critical as you gain wealth and power