Making Hard Decisions as a Founder
Some decisions are just hard. Here's how to navigate the toughest calls.
Easy decisions aren’t what you’re paid for. The hard decisions—the ones with no clear right answer, where something is lost either way, where you’re deciding in the dark—these define your journey as a founder. Learning to make hard decisions well is one of the most valuable skills you can develop.
What Makes Decisions Hard
Uncertainty
Not enough information:
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Can’t predict outcomes
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Experts disagree
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Data is incomplete
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Future is unknowable
Trade-offs
No win-win available:
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Every option costs something
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Gains and losses on each side
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Can’t have it all
High Stakes
Significant consequences:
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Big impact if wrong
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Difficult to reverse
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Affects many people
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Company rides on it
Values Conflict
Competing principles:
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Loyalty vs. performance
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Short-term vs. long-term
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Individual vs. team
Emotional Weight
Decisions that hurt:
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Letting people go
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Closing projects
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Abandoning products
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Disappointing people
Types of Hard Decisions
People Decisions
The hardest often involve people:
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Firing someone
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Promoting (or not)
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Founder conflicts
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Salary and equity
Strategic Decisions
Direction choices:
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Pivoting
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Shutting down a product
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Entering new markets
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Major investments
Resource Decisions
Allocation choices:
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Where to cut
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What to fund
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Who to hire
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What to stop
Ethical Decisions
Right and wrong:
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Competitive practices
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Customer treatment
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Information sharing
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Value conflicts
A Framework for Hard Decisions
1. Define the Decision
Be clear about:
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What exactly am I deciding?
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What are the options?
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What’s the deadline?
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Who’s affected?
Clarity enables better thinking.
2. Gather Information
Get what you need:
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Relevant data
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Expert opinions
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Different perspectives
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Comparable situations
But don’t use gathering as procrastination.
3. Understand Trade-offs
For each option:
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What do we gain?
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What do we lose?
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What’s the risk?
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What’s reversible?
4. Consider Principles
What matters most:
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Company values
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Personal ethics
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Long-term vision
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Key stakeholders
5. Check for Bias
Are you being influenced by:
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Sunk costs
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Optimism bias
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Confirmation bias
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Status quo preference
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Personal attachment
6. Decide
Make the call:
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With available information
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Accepting uncertainty
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Committing fully
Indecision is often worse than imperfect decision.
7. Communicate and Execute
After deciding:
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Explain the decision
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Acknowledge trade-offs
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Commit to implementation
8. Learn
Whatever happens:
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Did it work?
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What would you do differently?
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What did you learn?
Decision-Making Aids
The Regret Test
Imagine future you:
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“Will I regret not doing this?”
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“Will I regret doing this?”
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Which regret is more tolerable?
The Newspaper Test
Two versions:
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“Would I be comfortable if this decision was published?”
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Both for ethical check and quality check
The Advisor Test
What would a trusted advisor say?
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Someone whose judgment you respect
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What would they recommend?
The Pre-mortem
Imagine the decision failed:
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What caused it?
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Could you have predicted this?
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Does that change your decision?
The Default Test
If you had to decide right now:
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What would you choose?
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Trust your instinct, then validate
Specific Hard Decision Types
Firing Someone
Perhaps the hardest:
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Have they had clear feedback?
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Have they had opportunity to improve?
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Is the decision fair?
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What’s the impact of not acting?
Act when it’s clear. Waiting rarely helps.
Pivoting
Changing direction:
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What’s the evidence for change?
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What are you giving up?
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Is it a true pivot or giving up too soon?
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Are you running from problems or toward opportunity?
Shutting Down
Ending something:
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Is there a viable path forward?
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What’s the cost of continuing?
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Are you seeing clearly?
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What do stakeholders deserve?
Co-founder Issues
Relationship problems:
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Can this be resolved?
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What’s best for the company?
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What’s fair to both parties?
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What happens if you don’t act?
Common Mistakes
Decision Avoidance
Not deciding:
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Hoping the problem resolves
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Kicking the can
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Analysis paralysis
Not deciding is deciding (usually for the worse).
Deciding in Isolation
Not getting input:
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Missing information
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Bias unchecked
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Blind spots
Get perspective before deciding.
Optimism Bias
Assuming best case:
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Discounting risks
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Ignoring warning signs
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Planning for success only
Consider realistic and downside scenarios.
Sunk Cost Fallacy
Continuing because of past investment:
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“We’ve already spent so much…”
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Ignoring that it’s gone
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Evaluating future based on past
Decide based on future, not past costs.
Deciding for Wrong Reasons
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To avoid discomfort
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To please someone
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Because it’s easier
Decide based on what’s right, not what’s easy.
After the Decision
Living with Uncertainty
You may never know if it was right:
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Counterfactual is unknowable
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Made best decision with available info
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Can’t second-guess forever
When Decisions Prove Wrong
If it was the wrong call:
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Acknowledge it
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Learn from it
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Adjust course
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Don’t dwell
Building Confidence
Each hard decision builds capability:
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You’ve done it before
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You can do it again
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Experience compounds
Key Takeaways
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Hard decisions involve uncertainty, trade-offs, high stakes, and emotional weight
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People decisions are often the hardest: firing, co-founder issues, team changes
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Framework: define clearly, gather info, understand trade-offs, check bias, decide, execute, learn
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The regret test: which regret is more tolerable?
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Not deciding is deciding—usually for the worse
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Sunk costs are irrelevant: decide based on future, not past investment
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Get perspective before deciding; isolation leads to blind spots
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You may never know if it was “right”—you made the best decision with available info
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When decisions prove wrong: acknowledge, learn, adjust, don’t dwell
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Each hard decision builds capability; experience compounds
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