Introduction
Sometimes clients propose solutions that you know won't achieve their goals—or worse, will create serious problems. How you navigate these "that won't work" moments determines whether you're seen as a valuable advisor or an obstruction. The goal is to redirect without dismissing, educate without condescending, and arrive at better solutions collaboratively.
Why This Skill Matters
When handled poorly, clients feel dismissed, the relationship becomes adversarial, and poor solutions get implemented out of stubbornness. When handled well, clients appreciate your expertise, trust deepens, and better solutions emerge from collaboration.
Core Principles
- Validate their intent before challenging their approach
- Explain consequences rather than just saying "no"
- Offer alternatives that address their underlying goal
- Use questions to guide them toward realizations
- Maintain collaborative tone - it's "we" not "you vs. me"
Good Examples
Client: "Let's just store all user passwords in a spreadsheet so we can reset them easily."
Good Response: "I hear that password resets are a pain point you want to solve—that's a legitimate need. Let me explain why the spreadsheet approach would create serious problems, and then I'll suggest a better solution.
The risks: Storing passwords in plain text violates security best practices and regulations like GDPR. If that spreadsheet is ever accessed—by malware, a disgruntled employee, or a data breach—all user accounts are immediately compromised. You'd face significant legal and reputational consequences.
What we should do instead: Implement a secure password reset flow where users request a reset via email, receive a time-limited reset link, and create a new password. This is secure, industry-standard, and actually easier for users than contacting support.
I can build this as part of the authentication system with minimal additional time. This protects you legally, protects your users, and solves the pain point you identified. Does that approach work?"
Why It Works
Validates the underlying concern, explains consequences clearly, provides secure alternative, frames as solving their real problem.
Bad Examples
Bad Response: "That's a terrible idea. You can't do that. Just trust me."
Why It's Bad
Dismissive, provides no reasoning, doesn't offer alternatives, creates adversarial dynamic.
Tips for Developing This Skill
- Start with validation - "That's an interesting approach" or "I understand what you're trying to achieve"
- Use consequence framing - "If we do that, here's what would happen..."
- Provide better alternatives - Never just say no
- Ask guiding questions - "How would we handle [edge case]?" to surface issues
- Connect to their goals - "You want [goal], this alternative achieves that more effectively"
- Maintain respect - They're intelligent, just not domain experts
Connection to Other Skills
Combines gentle pushback, explaining complex concepts, instilling confidence, asking questions, and collaborative problem-solving to redirect without dismissing.
Action Items
- Next time a client proposes something problematic, use: "I see what you're trying to achieve. Let me share concerns and alternatives"
- Practice explaining consequences without sounding alarmist
- Build a library of better alternatives for common problematic requests
- Develop questions that help clients discover issues themselves