You ask your board, your team, your advisors what they think. They tell you to keep going. Of course they do. That's what supportive sounds like.
The problem: support and accuracy are different things. And in strategic decision-making, you need accuracy.
Daniel Kahneman described what he needed from his research partner Richard Thaler: "A friend who really loves them but does not care much about hurt feelings in the moment." If a Nobel laureate in decision-making needs external perspective, so does everyone else.
The Permission Problem
When you ask for advice, you're usually asking for reassurance. The advisor picks up on that signal. Without an explicit agreement to the contrary, they default to telling you what you want to hear.
This isn't malicious. It's social. People want to maintain relationships. They want to be supportive. Delivering unwanted truth creates friction.
The result is systematic optimism bias in the advice you receive. Everyone agrees the strategy is working because disagreeing is socially costly.
Permission is a contract. Without it, advisors default to comfort over accuracy.
Kahneman got value from Thaler because Kahneman explicitly gave permission to hear what he didn't want to hear.
The Structured Feedback Method
Silicon Valley investor Ron Conway developed a method for giving founders honest feedback without triggering defensive responses:
Step 1: Name the possibility of exit. "I think you should seriously consider winding this down." Put the option on the table without demanding agreement.
Step 2: When they push back, retreat. "You might be right—you know the business better than I do." This keeps the relationship intact and the conversation open.
Step 3: Define near-term success together. "What would need to be true in six weeks for you to feel confident continuing? Let's write it down."
Step 4: Set a revisit date. "If those benchmarks aren't met by [date], we have this conversation again." Creates accountability without immediate pressure.
The critical insight: steps 3 and 4 create permission for future honesty. Once you've agreed on benchmarks together, you've earned the right to be direct when they fail.
Why Brutal Honesty Fails
The opposite extreme doesn't work either. Research shows that unsolicited brutal feedback often triggers defensive doubling down rather than course correction.
Someone asking "what do you think?" isn't necessarily granting permission to deliver hard truths. The request often means "please validate what I've already decided." Responding with blunt criticism triggers identity defense rather than reflection.
"If you want to help, don't drop truth-bombs. Build a process that earns permission."
Building the Permission Structure
Effective truth-telling relationships require explicit permission. Some operational phrases:
- "I'm not looking for reassurance. I'm looking for accuracy."
- "If your honest assessment is that we should exit, I want you to say it."
- "If I get defensive, don't retreat immediately—help me slow down and look at the data."
- "Can we set specific benchmarks and a review date? I want your honest assessment against those criteria."
These phrases work because they pre-authorise discomfort. They tell the advisor: your job isn't to protect my feelings.
Don't Command—Help Them See
Even with permission, telling someone what to do often backfires. Command triggers resistance. Questions trigger ownership.
A trusted advisor doesn't say "you should exit." They ask questions that surface the conclusion:
- "If this were a new investment opportunity at current terms, would you take it?"
- "What result would make you confident we should continue? What result would make you furious we didn't exit earlier?"
- "What are we giving up by staying in this position? What else could we do with these resources?"
- "If an outside observer saw this data, what would they conclude?"
These questions translate the situation into expected value terms without triggering the defensiveness that direct advice provokes.
Institutional Design
Individual relationships matter, but institutional structure matters more. Some design principles:
Independent Board Members
Board members without operational involvement have fewer identity investments to protect. They can ask hard questions without social cost.
Devil's Advocate Roles
Assign someone the explicit job of arguing the exit case. Their role gives permission to voice what others are thinking but won't say.
External Reviews
Periodic assessment by parties outside the organisation. They're not contaminated by the internal narrative and can see what insiders cannot.
Retrospective Dignity
How an organisation treats people who advocate for exits matters. If arguing for exit creates career risk, honest feedback will be rare. If it's valued as rigorous thinking, it will be common.
1. Identify Your Advisor
Who has enough distance to see clearly and enough stake to care about accuracy?
2. Grant Explicit Permission
Use specific language: "I want your honest assessment, not reassurance. If the data says exit, I want to hear it."
3. Set Shared Criteria
Agree on benchmarks together. Write them down. This creates the basis for future honesty.
4. Schedule Review
Set a specific date to evaluate against criteria. Don't leave timing ambiguous.
5. Receive Without Defense
When feedback comes, don't argue. Ask clarifying questions. Understand before responding.
The Meta-Level
At the deepest level, getting honest feedback requires believing that accurate information is more valuable than comfortable information. Many operators say they want truth but react defensively when they get it.
The question to ask yourself: do you actually want to know if this isn't working? Or do you want validation that it is?
If you want validation, you'll get it. Everyone will tell you what you want to hear. But you'll keep investing in positions that should have been exited, wondering why the results don't match the optimism.
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This article is for educational purposes and does not constitute business or professional advice. Strategic decisions should be made with appropriate professional counsel.