How To Face The Most Uncomfortable, High-Frequency Management Situations Head On

Read Time: 3 minutes.

I'm embarrassed to admit this, but I had been dodging Sarah's performance issues for months.

• She was loved by the team

• She was always willing to help

• She had her heart in the right place.

But her work wasn't meeting standards. I knew it. Everyone knew it.

Each week, I rationalized why it was ok to put off the conversation. She showed glimmers of improvement. I had bigger fish to fry.

As team members started covering for her, resentment built quietly. My lack of courage was causing distraction across the team.  

When I finally shared feedback on her growing list of mistakes, Sarah's first words were devastating:

"Why did you wait so long to tell me?"

I learned what most managers eventually learn:  

Avoiding hard conversations only makes them harder.

The temporary comfort of avoidance always comes with compound interest.

Here's how to handle the 15 most common and most challenging management situations directly, fairly, and effectively.

Performance Problems with Well-Liked Employees

Address it as a shared problem-solving exercise, not a confrontation. Schedule a dedicated meeting with a clear agenda: "I want to discuss some gaps between expectations and results." Focus on specific examples and create a clear, measurable improvement plan.

Resolving Interpersonal Conflicts

Don't. Start by being clear they need to resolve it directly. If that doesn't work, bring parties together with clear ground rules. Focus on future behavior changes rather than past grievances. Set explicit expectations about professional conduct and follow up within a week.

Delivering Negative Feedback

Make it immediate, specific, and tied to impact. Skip the compliment sandwich - it undermines credibility. State the issue, explain the impact, suggest an alternative approach, and confirm understanding.

Managing a High-Performer with an Attitude Problem

Frame the conversation around expanding their influence, not controlling their behavior. "Your technical skills are valuable, but your impact could be even greater if..." Set clear behavioral expectations.

Managing Poor Performers Who Try Hard

Focus on results, not effort. Identify specific capability shortcomings and provide training and support. Pair this with measurable milestones. Be clear about the consequences if they can't close the gaps.

Dealing with Chronic Complainers

Use management jujitsu and assign the responsibility of solving the problem. Hold them accountable for implementing their suggestions and gaining buy-in from others. Set boundaries on "chirping" without taking action.

Managing Personal Friction with Your Boss

Address issues directly with specific examples. Focus on results, but make sure you speak in their "love language." Propose solutions, not just problems. Write down key conversations and agreements.

Managing Unmotivated but Technically Competent Employees

Connect their work to the larger mission. Offer new challenges or team leadership opportunities. Be direct about engagement concerns and set clear expectations for participation. You can't dictate their energy, but you can encourage better outcomes.

Addressing Claims of Burnout from Team

Diagnose the source. Dig into specific examples of what's causing strain. Take immediate action if it's obvious overload. Create visible changes to workload or processes. Check temperature frequently.

Negotiating Conflicts over Resources/Priorities

Be honest: Can you say “No?” Focus on business impact, not team preferences. Search for creative win-win options. Escalate stuck conflicts to key stakeholders quickly. Show up with clearly documented trade-off decisions and their rationale.

Implementing Unpopular Policies

Explain the 'why' behind changes. Acknowledge the downsides openly. Get answers to questions if you don't have them. Focus on how to implement effectively rather than debating the policy itself.

Reconciling Demands from Different Stakeholders

Resolve what you can point-to-point. Bring parties together. Ensure everyone appreciates what's at stake. Surface must-dos and areas of flex. Bring in someone with authority over both areas to break deadlocks.

Managing through Major Change/Uncertainty

Communicate what you know, what you don't, and when you'll know more. Share your questions, uncover theirs. Focus on what remains constant. Create short-term wins and visibility. Overcommunicate in times of change.

Delivering Bad News to the Team

Be direct and brief with the news itself. Take questions, but dissuade complaining. Focus most of the conversation on the next steps. Follow up individually with the most impacted team members.

Inspiring Team When Missing Key Targets

Ask questions to understand why they're missing. Agree on needed support. Break work into smaller, winnable milestones. Celebrate effort toward improvement without compromising high standards.

What You Missed This Week

Did you miss this week’s MGMT Minute?

📌 We broke down 12 concrete actions for building trust.

1. How To Delegate Anything (And Everything)

2. How To Manage Your Boss

3. 16 Simple Ways Anyone Can Lead

4. Why Leaders Should Think Like Farmers

5. Boss vs Leader | 8 Moves That Make The Difference

6. 7 Questions To Ask In 1:1 Meetings

Our goal is to build a community of 1 million thoughtful, curious leaders.

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Thank you for reading. Appreciate you!

Dave & Mar