Underperformance is one of the most painful challenges leaders face.
You don't want to crush someone's confidence. You don't want to damage the relationship. But you also can't ignore it — the rest of the team notices, productivity suffers, and your credibility takes a hit.
The good news? Most underperformance can be turned around with the right approach. Here's how to do it.
Diagnose Before You Prescribe
Not All Underperformance Is the Same
Before you say anything, you need to understand what's actually happening. Underperformance usually falls into one of four categories:
- Can't do it: They lack the skills, knowledge, or experience
- Won't do it: They're motivated but choose not to put in the effort
- Don't know why: They don't understand the importance or purpose
- Something else: Personal issues, burnout, health problems, family crisis
Your diagnostic checklist:
- Gather specific data: What exactly is missing? When did it start? How often?
- Check resources: Do they have the tools, information, and authority to succeed?
- Review training: Were they properly onboarded and trained for this role?
- Look for patterns: Is this isolated to one area or showing up everywhere?
- Consider context: Has anything changed recently in their life or work environment?
The Eisenhower Principle: Dwight Eisenhower was known for his ability to diagnose situations quickly and accurately before taking action. He'd spend hours understanding the full picture, then act decisively. "The hardest battle is always the one within your own mind." Know your facts before you speak.
The Motivation Conversation Framework
A Structure That Works
Once you've diagnosed the situation, have a direct but compassionate conversation:
- State observations factually: "I've noticed X has happened Y times"
- Express concern, not judgment: "I'm concerned because I know you're capable of more"
- Ask open-ended questions: "What's making this challenging?" "What support do you need?"
- Listen actively: Give them space to share. Don't interrupt or defend.
- Collaborate on solutions: What will change? What timeline makes sense?
- Set clear expectations: Document what success looks like and when you'll review progress
The Roosevelt Approach: Theodore Roosevelt believed in being both firm and fair. He'd never sugarcoat problems, but he'd also treat people with dignity. "Do what you can, with what you have, where you are." Assume positive intent until proven otherwise.
Motivation Strategies That Actually Work
Connect Work to Purpose
People perform better when they understand why their work matters. Explain how their role contributes to the team's goals, the company's mission, and the customer's success.
Example script:
- "I want to show you how your work on X directly impacts our customers."
- "When you deliver quality work here, it enables the whole team to succeed."
- "Your contributions matter because Y."
Remove Obstacles
Sometimes underperformance comes from friction points you haven't noticed. Ask what's getting in their way and commit to removing those barriers.
This could mean better tools, clearer processes, additional training, or simply giving them more autonomy to work in their preferred style.
Create Small Wins
If someone's been struggling, they may have lost confidence. Break larger goals into smaller, achievable milestones so they can experience success regularly.
Key principle: Momentum builds motivation. Each small win creates evidence that they can succeed, which fuels the drive to keep going.
Recognize Effort and Progress
Celebrate improvements, even incremental ones. Public recognition for a job well done can be incredibly motivating for people who've been struggling.
What NOT to Do
1. Assuming Malice
Most underperformance isn't intentional sabotage. Start with curiosity, not accusation. There's almost always a reason behind the behavior.
2. Comparing to Others
Don't say "Why can't you be more like Sarah?" This creates resentment and damages trust. Focus on their individual performance against expectations.
3. Waiting Too Long
Every day you delay makes it harder. Address performance issues within days, not weeks. The longer you wait, the more it affects the team and the harder the turnaround becomes.
4. Making Empty Threats
If you say "this could cost you your job" and nothing happens, you lose credibility. Only make consequences you're willing and able to enforce.
5. Doing It Over Email
These conversations need to happen in person or via video call. Tone gets lost in text, and important nuance disappears.
The Hard Truth About Tenure
Sometimes, despite your best efforts, someone won't turn around. And that's okay.
You cannot force motivation onto someone who doesn't want it. You cannot coach skill gaps that won't close. You cannot fix a fundamental mismatch between person and role.
In these cases, the kindest thing you can do is acknowledge the reality and part ways professionally. This protects the team, preserves your credibility, and gives the person a chance to find a role where they'll actually thrive.
The MacArthur Rule: General Douglas MacArthur said: "There is no security on this earth — only opportunity." Sometimes the best leadership decision is helping someone find a better fit elsewhere.
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Talk to Cabinet Free →Frequently Asked Questions
What are the first steps when an employee starts underperforming?
Gather specific data about their performance gaps, schedule a private conversation to understand what's going on, look for patterns, check if they have the right resources and training, and listen for personal issues that might be affecting their work.
How do you know if motivation is the real problem?
Motivation isn't the issue if the person lacks skills, clarity, or resources. Ask yourself: Do they know what to do? Do they have the tools to do it? Can they do it? If the answer to all three is yes but they still aren't performing, then it's likely a motivation or engagement issue.
What's the best way to give feedback to someone who's disengaged?
Use curiosity-driven questions rather than accusations. Ask "What's making this challenging?" instead of "Why aren't you doing better?" Focus on the impact of their performance on the team, express your desire to help them succeed, and collaborate on solutions.
When should you consider letting someone go?
After you've provided clear expectations, adequate support, reasonable timeframes for improvement, and documented conversations — and there's still no change. Also consider letting them go if their behavior is toxic to the team or if the role fundamentally doesn't match their strengths.
How long should you give someone to improve?
Typically 30-60 days, depending on the severity of the issue and the complexity of the required changes. Set clear milestones along the way so you both know whether progress is being made.