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Module 7: Team Leadership & Coaching

Handle difficult conversations, provide constructive feedback, motivate teams, and develop leadership communication skills.

📚 Week 4 🎯 Intermediate

🎯 What You'll Master

Navigate difficult conversations with confidence and empathy
Deliver constructive feedback that motivates instead of demotivates
Develop coaching scripts for underperforming team members
Build recognition messages that authentically boost team morale

The Leadership Communication Gap

Project Managers are expected to lead teams without formal authority—no hiring/firing power, no direct reports, yet responsible for performance, morale, and outcomes. The hardest part? Having difficult conversations you're not trained for.

⚠️ The PM Leadership Paradox

What PMs Avoid (But Shouldn't):

Result: Issues fester, resentment builds, projects suffer—all because we delay tough conversations.

ChatGPT acts as your leadership coach—helping you prepare for difficult conversations, craft feedback that lands well, and develop communication strategies that build trust instead of burning bridges.

💬 1. Handling Difficult Conversations

The key to difficult conversations is preparation. ChatGPT helps you anticipate reactions, plan your approach, and stay calm when emotions run high.

The 4-Step Difficult Conversation Framework

1️⃣ Open with Empathy

Acknowledge the other person's perspective first

Example: "I know you've been working incredibly hard..."

2️⃣ State the Facts

Describe the situation objectively, without judgment

Example: "The last 3 milestones were delivered 2-4 days late..."

3️⃣ Explain the Impact

Show how the behavior affects the team/project

Example: "This creates downstream delays for QA and blocks launch..."

4️⃣ Collaborate on Solutions

Invite them to problem-solve with you

Example: "What support do you need to hit deadlines going forward?"

ChatGPT Conversation Prep Prompt

Help me prepare for a difficult conversation with a team member:

Situation:
Sarah is a senior backend developer who's been missing deadlines consistently for 3 weeks. 
She's technically brilliant but seems disengaged lately. Other team members are picking up 
her slack and it's causing resentment.

Background:
- Missed 3 consecutive milestones (2-5 days late each)
- Daily standups: says "everything's fine" but doesn't provide specifics
- Code quality remains high, but velocity is down 40%
- I suspect she's burned out or dealing with personal issues

My Concerns:
- Don't want to sound accusatory (she's a valuable team member)
- Need to address the pattern without damaging our relationship
- Other devs are starting to complain
- Project timeline is at risk

Help me:
1. Draft an opening statement that's empathetic but direct
2. Anticipate her possible reactions and how to respond
3. Suggest questions to uncover root cause
4. Create a collaborative action plan framework
5. Identify what support I can offer

Tone: Supportive but firm, focused on solutions not blame

✨ AI-Generated Conversation Guide:

🗣️ Opening Statement (Empathy + Facts)

✅ What to Say:
"Sarah, thanks for making time to talk. I want to check in with you because I've noticed some changes in the past few weeks that I'm concerned about. You're one of our strongest developers, and I value your contributions enormously. At the same time, I've noticed that the last three milestones—authentication module, payment integration, and API documentation—were each delivered 2-5 days behind schedule. I know you're working hard, and I'm not questioning your effort. But I wanted to talk with you directly to understand what's going on and how I can support you."

❌ What NOT to Say:

"Sarah, you've been missing every deadline lately. The team is complaining and I need you to get back on track. Is something wrong?"

Why this fails: Starts with accusation, invites defensiveness, sounds like you're responding to team complaints rather than genuine concern.

🎭 Anticipating Reactions & Responses

Reaction 1: Defensive ("I'm doing my best!")

Your Response:
"I absolutely believe that, and I'm not questioning your effort at all. You're one of the hardest-working people on this team. That's actually why I'm concerned—if someone as capable as you is struggling to meet timelines, it tells me something systemic might be wrong. Can you help me understand what's blocking you?"

Reaction 2: Deflection ("The requirements keep changing")

Your Response:
"That's a really valid point, and I appreciate you bringing it up. Scope creep has been an issue. Let's absolutely address that. But even accounting for those changes, we're seeing a pattern that's different from your usual pace. Is there something else contributing to this?"

Reaction 3: Opens Up ("I'm honestly just burned out")

Your Response:
"Thank you for being honest with me. Burnout is real, and I want to make sure we address it before it gets worse. What would help right now? Should we look at redistributing some of your tasks, giving you a break after this sprint, or adjusting expectations for the next few weeks?"

🤝 Collaborative Action Plan Framework:

Questions to Ask:

  1. "What's the biggest obstacle preventing you from hitting your deadlines?"
  2. "On a scale of 1-10, how manageable does your workload feel right now?"
  3. "Is there anything happening outside of work that I should be aware of? (You don't have to share details, but it helps me understand how to support you)"
  4. "What would success look like for you over the next 2-3 weeks?"

Support You Can Offer:

  • Workload Adjustment: "I can reassign the API testing to Mike to lighten your plate"
  • Time Off: "Take Friday off to recharge—no questions asked"
  • Flexible Schedule: "If you need to shift your hours or work remotely more, that's fine"
  • Pair Programming: "Want to pair with another dev on complex tasks to speed things up?"
  • Weekly Check-ins: "Let's do a quick 1-on-1 every Monday to catch issues early"

📝 2. Delivering Constructive Feedback

Feedback is only useful if it's specific, actionable, and delivered in a way that motivates improvement. Generic praise ("Great job!") or vague criticism ("Your code needs work") doesn't help anyone grow.

The SBI Feedback Model (Situation-Behavior-Impact)

📊 How SBI Works:

  1. Situation: Describe when and where the behavior occurred (context)
  2. Behavior: Describe the specific, observable action (facts, not judgments)
  3. Impact: Explain the result of that behavior (consequences)

Why it works: Removes emotion, focuses on facts, shows real-world consequences.

ChatGPT Feedback Generation Prompt

Generate constructive feedback using the SBI (Situation-Behavior-Impact) model:

Person: Junior developer (Alex)
Context: Sprint retrospective revealed communication issues

Behaviors to Address:
1. Doesn't speak up in daily standups (says "no blockers" even when stuck)
2. Submits PRs without context/descriptions
3. Asks questions via DM instead of in team channels (others can't learn)

My Goal:
- Encourage better communication habits
- Don't discourage asking questions (that's good!)
- Show how these behaviors impact the team
- Provide specific actions they can take

Tone: Supportive coaching, growth-oriented

Generate:
1. SBI feedback for each behavior
2. Specific actions Alex can take to improve
3. Positive examples of good communication to model
4. Follow-up plan to track progress

✨ AI-Generated Feedback Framework:

📌 Feedback #1: Speaking Up in Standups

Situation: "In the last three daily standups..."

Behavior: "...you said 'no blockers' each time, but later I found out you were stuck on the authentication bug for 2 days."

Impact: "This meant you lost 2 days of productivity when someone could have helped you in 20 minutes. It also delayed the feature for the entire team."

✅ Specific Actions to Improve:

  • In standups: "If you've been stuck on something for more than 2 hours, say so—even if you think you'll figure it out"
  • Use this phrase: "I'm working on [X], and I could use a quick sanity check on [Y]"
  • Reframe 'blockers': It's not a sign of weakness—it's how teams stay unblocked

📌 Feedback #2: Pull Request Descriptions

Situation: "When you submitted the user profile PR yesterday..."

Behavior: "...the description was empty, and the title just said 'user profile updates'"

Impact: "The reviewer (Sarah) had to spend 30 extra minutes reading through the code to understand what changed and why. It also makes it harder for us to track changes in the future."

✅ Specific Actions to Improve:

  • PR Template: Use this format:
    • What: Brief summary of changes
    • Why: Problem you're solving or feature you're adding
    • How: Key technical decisions
    • Testing: How you verified it works
  • Good example: "Show Alex Sarah's recent PR as a model"

📌 Feedback #3: Asking Questions Publicly

Situation: "Over the past 2 weeks..."

Behavior: "...you've DMed me and other developers with technical questions instead of posting in #engineering-help"

Impact: "This means other juniors don't benefit from the answers, and we end up answering the same questions multiple times. Also, it limits who can help you—sometimes someone else has a better answer."

✅ Specific Actions to Improve:

  • Default to public channels: Post questions in #engineering-help first
  • DMs are fine for: Sensitive topics, personal issues, or follow-ups to public threads
  • Bonus: When you figure something out, post the solution publicly so others learn

📈 Follow-Up Plan (Next 2 Weeks):

  1. Week 1: Daily check-in after standup ("How's it going? Any blockers today?")
  2. Week 2: Review Alex's last 3 PRs—are descriptions improving?
  3. Week 2: Monitor #engineering-help—is Alex asking questions publicly?
  4. End of Week 2: Quick 1-on-1: "How are the communication changes feeling? Any challenges?"

🏆 3. Recognition & Motivation Messages

Recognition is one of the most underutilized leadership tools. When done well, it boosts morale, reinforces positive behaviors, and builds team culture. When done poorly (generic "good job!" messages), it feels hollow.

What Makes Recognition Effective?

✅ Effective Recognition:

  • Specific: References exact actions
  • Timely: Given soon after the achievement
  • Impact-Focused: Shows why it mattered
  • Public (when appropriate): Shared with team/company
  • Authentic: Genuinely felt, not formulaic

❌ Ineffective Recognition:

  • Vague: "Great work on the project!"
  • Late: Recognition 2 months after the fact
  • Generic: Copy-paste messages
  • Private only: No team visibility
  • Insincere: Feels like checkbox exercise

ChatGPT Recognition Prompt

Write a team recognition message for someone who went above and beyond:

Person: Maria (UX Designer)
Achievement: Completely redesigned the checkout flow in 3 days (originally estimated 2 weeks)

Context:
- We had a tight deadline (investor demo in 5 days)
- Original design had 8 steps; Maria simplified it to 3
- She worked late nights and weekends without being asked
- User testing showed 40% increase in completion rate
- Other designers helped, but Maria drove the effort

Audience: Public announcement in company Slack channel

Tone: Grateful, specific about impact, celebrates team collaboration

Include:
- Specific actions Maria took
- Business impact of the work
- Personal qualities demonstrated
- Thank other team members who helped
- Emoji and energy (but keep professional)

✨ AI-Generated Recognition Message:

🎉 HUGE shoutout to Maria for absolutely crushing the checkout redesign! 🎉

With only 5 days until our investor demo, Maria took on what was scoped as a 2-week project and delivered it in 3 days—without sacrificing quality or cutting corners.

What she did:

  • Simplified our 8-step checkout flow down to 3 steps (massive UX win)
  • Ran guerrilla user testing with 12 customers over the weekend to validate the design
  • Collaborated closely with Dev and Product to ensure feasibility
  • Created high-fidelity prototypes that the dev team could implement immediately

The impact: User testing showed a 40% increase in checkout completion rates. This redesign is going to directly boost revenue and customer satisfaction. 🚀

Maria—your dedication, creativity, and problem-solving under pressure were incredible to watch. You didn't just meet the deadline; you delivered something that's genuinely better than what we originally planned.

Also want to recognize Priya and Jake for jumping in to help with user testing and feedback sessions. Team effort all the way. 💪

Thank you, Maria. This is the kind of work that makes our team exceptional. 🙌

💡 Why This Works:

  • Specificity: Lists exactly what Maria did (not just "great job")
  • Impact: Quantifies results (40% completion rate increase)
  • Context: Explains the tight timeline and pressure
  • Collaboration: Acknowledges others who helped
  • Qualities: Highlights dedication, creativity, problem-solving
  • Tone: Enthusiastic and genuine (emoji use is appropriate for Slack culture)

🎯 Practice Exercise: The Underperformer Coaching Conversation

Scenario:

You manage a 10-person development team. One developer, Tom, has been underperforming for 6 weeks. He's a mid-level dev (3 years experience) who was previously solid but is now:

You need to have a coaching conversation tomorrow. Your goal is to understand what's wrong, set clear expectations, and create an improvement plan—without demotivating him further or coming across as punitive.

Your Task:

  1. Prep your opening: Write the first 2-3 sentences using the empathy + facts framework
  2. Anticipate 3 reactions: How will you respond to defensiveness, excuses, or shutting down?
  3. Create an improvement plan: What specific actions and timeline?
  4. Define support: What can you offer to help Tom succeed?

💡 Use This Prompt:

Help me prepare for an underperformance coaching conversation:

Team Member: Tom (mid-level developer, 3 years experience)
Duration of Issue: 6 weeks
Previous Performance: Solid, reliable

Current Issues:
- Velocity down 30-50% (used to complete 8 story points/sprint, now 4-5)
- Code quality declining (3 bugs found in last 2 PRs, normally none)
- Disengaged in meetings (camera off, minimal participation)
- Team members complaining about picking up his work

Possible Causes (Unknown):
- Personal issues?
- Burnout?
- Bored with current work?
- Looking for new job?
- Technical skill gap?

My Goals:
1. Understand root cause without prying into personal life
2. Set clear performance expectations
3. Create 30-day improvement plan
4. Offer support while holding accountability
5. Avoid being punitive or demotivating

Generate:
1. Opening statement (empathetic but direct)
2. 3 possible reactions and how to respond
3. Questions to uncover root cause
4. 30-day improvement plan with milestones
5. Support I can offer vs. expectations I must hold
View Sample Coaching Plan ↓

Sample AI-Generated Coaching Framework:

✅ Opening Statement:
"Tom, I wanted to talk with you because I care about your success on this team, and I've noticed some changes over the past 6 weeks that concern me. You've been a reliable, solid contributor for a long time, so this isn't your usual pattern. Your velocity has dropped from about 8 story points per sprint to 4-5, and we've seen a few quality issues in recent PRs that aren't typical for you. I also notice you seem less engaged in meetings lately. I'm not here to criticize—I want to understand what's going on and figure out how I can support you. Can you help me understand what's changed?"

30-Day Improvement Plan:

📅 Week 1-2: Diagnosis & Quick Wins

  • Action: Daily 10-min check-ins to identify blockers
  • Goal: Complete 6 story points (vs current 4-5)
  • Success: Zero bugs found in code review

📅 Week 3-4: Momentum Building

  • Action: Reduce check-ins to 3x/week
  • Goal: Complete 7 story points
  • Success: Participates actively in 2+ team meetings

📅 End of Month Review:

  • Metrics: Velocity back to 8 story points, code quality improved, engagement up
  • If successful: Continue with monthly check-ins
  • If unsuccessful: Escalate to manager, discuss PIP options

🎓 Key Takeaways

🚀 What You've Mastered

You can now prepare for difficult conversations with confidence, deliver constructive feedback that motivates improvement, and recognize team members in ways that build genuine morale. AI acts as your leadership coach, helping you navigate the human side of project management.

Next up: Module 8 will show you how to run efficient meetings, capture action items, and create documentation that actually gets read.

📝 Knowledge Check

Test your understanding of AI for team leadership!

1. How can AI support team leadership?

A) By replacing all leadership functions
B) By providing coaching insights and communication suggestions
C) By making all team decisions
D) Leadership doesn't need AI

2. What can AI help with in performance feedback?

A) Delivering feedback automatically
B) Avoiding difficult conversations
C) Structuring constructive, balanced feedback
D) Eliminating need for 1-on-1s

3. How should AI be used in team motivation?

A) Suggesting recognition approaches and team-building ideas
B) Replacing personal connection
C) Automating all motivation
D) Motivation doesn't involve AI

4. What is important when using AI for leadership?

A) Let AI handle all team interactions
B) Avoid personal judgment
C) Follow AI suggestions blindly
D) Balance AI insights with empathy and human connection

5. How can AI assist with conflict resolution?

A) By avoiding conflicts
B) By suggesting mediation strategies and neutral phrasing
C) By making decisions for the team
D) Conflicts cannot involve AI