People Build Companies

How to Say “This Isn’t Working” (Without Ruining the Relationship)

Written by Steve Taylor | Mar 19, 2026 1:10:56 AM

The Goal 

You can tell someone the truth without tearing them down. Performance conversations should create clarity—not casualties. 

The Real Question 

How do I talk about underperformance without making things worse? 

🎯 The Clear Answer 

Avoiding hard conversations doesn’t protect people—it misleads them. Founders who lead with respect and clarity don’t wait until it’s unbearable. They address issues early, name them directly, and keep the door open for growth. Saying “this isn’t working” isn’t the problem. Saying nothing is. 

It’s not harsh to be honest. It’s harsh to pretend. 

🛠 Project Formula: How to Solve It 

Phase 1 – Lead with Clarity, Not Emotion 
→ “I want to talk about what’s not working and give you a fair shot to adjust.” 
→ Stick to observable behaviors and missed outcomes 
→ Outcome: The conversation is about performance—not personality 

Phase 2 – Show the Path Forward 
→ “Here’s what success needs to look like going forward.” 
→ “Here’s the support I’m offering, and what I’ll need from you.” 
→ Outcome: The employee knows what’s expected—and that change is possible 

Phase 3 – Set a Checkpoint 
→ “Let’s check in again on [date]. We’ll look at X, Y, and Z.” 
→ Reinforce accountability while keeping the tone open and clear 
→ Outcome: No ambiguity, no ghosting, no slow exits 

✏️ Action Step 

Use the Difficult Conversation Script to prepare your next performance discussion—and avoid passive buildup. 

🧠 Founder Lens 

You didn’t sign up to be a therapist. But you did sign up to lead. Avoidance feels nice in the moment—but it erodes your culture and your credibility. Say what needs to be said. Do it with respect. Then move forward. 

💬 Quote to Share 

“Leadership isn’t silence. It’s saying what’s real—and staying in the room.”