Podcast | Best Christian Workplaces

457: Moving Through the Tunnel: A Harvard Expert's Guide to Difficult Conversations

Written by Best Christian Workplaces | August, 25 2025

What if the way we give and receive feedback could unlock healthier relationships and stronger workplace cultures? In this conversation, Sheila Heen—Harvard Law School lecturer, co-author of Thanks for the Feedback, and expert on negotiation and communication—shares powerful insights into why feedback is so hard and how leaders can navigate it with wisdom and grace.


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In this episode:

Guest Introduction & Background

  • Sheila Heen: Founder of Triad Consulting Group, Harvard Law School lecturer since 1995. (00:54)
  • 20+ years with Harvard Negotiation Project developing negotiation theory. (00:59)
  • Co-author of NYT bestseller "Difficult Conversations: How to Discuss What Matters Most." (01:18)
  • Specializes in emotionally charged negotiations and strained relationships. (01:05)

The Foundation: Why Difficult Conversations Matter

Organizational Change Reality

  • Ability to handle difficult conversations is prerequisite to organizational change. (01:43)
  • Globalized competition and technology create rapid change requiring adaptation. (02:35)
  • Change "finds us" regardless of organization size or market reach. (02:50)
  • Leaders increasingly need collaboration and influence skills across cultures and functions. (03:13)

Current Leadership Challenges

  • Many leaders feel "at a loss" about developing necessary collaborative skills. (03:47)
  • Technical capabilities alone insufficient for modern organizational needs. (03:53)
  • Change requires working across differences, cultures, and functions. (03:18)

The Structure of Difficult Conversations

The Three Internal Conversations

Every difficult conversation involves three simultaneous internal dialogues: (05:14)

1. The "What Happened?" Conversation

  • Our story about the situation: What we believe we're right about. (05:39)
  • Blame assignment: Whose fault it is (others or ourselves). (05:40)
  • Intention attribution: Why others are acting this way (clueless, controlling, difficult). (06:00)

2. The "Feelings" Conversation

  • Managing strong emotions not supposed to show at work. (06:41)
  • Feelings include: frustration, betrayal, confusion, sadness, fear, guilt. (06:47)
  • Emotions "leak out" through tone, body language, facial expressions. (06:58)

3. The "Identity" Conversation (Deepest Level)

  • What the situation suggests about us personally. (07:20)
  • Questions like: Am I a good leader? Am I valued? Am I competent? Am I worthy? (07:28)
  • These identity concerns fuel strong feelings and defensive stories. (07:38)

Moving Through the Tunnel: From Stuck to Solutions

The Problem with "Tunnel Vision"

  • We wear "blinders" looking for magic words to make others agree. (09:42)
  • Focus becomes getting them to see we're right rather than understanding differences. (10:11)
  • This approach keeps us stuck in unproductive patterns. (10:27)

Al's Personal Example: Bad News Conversations

  • Situation: Had to deliver disappointing news about not having a position for someone. (10:58)
  • Identity fear: Worried about disappointing others. (11:13)
  • Lesson: Had "blinders on" - didn't consider setup, other's emotions, or engagement. (11:26)

Key Insight on Bad News Delivery

  • If people aren't upset during bad news conversations, we may not be clear enough. (12:08)
  • Most people want bad news delivered: up front, straight, with willingness to hear impact. (13:37)
  • We often "tiptoe around" instead of following our own advice about directness. (13:47)

Creating Learning Conversations

Purpose Shift: The Game Changer

  • From: "I need to prove I'm right and get you to agree" (14:45)
  • To: "I want to understand why we see this differently" (15:03)

Learning Conversation Benefits

  • Better understanding of complete picture. (15:55)
  • Relationship improvement even without agreement. (16:02)
  • Opens possibility for genuine problem-solving. (16:43)
  • Both parties learn about each other's perspectives. (16:11)
  • Sometimes shifts our own perspective with new information. (16:17)

The Key Question

"Why do we see this differently?" - This simple question transforms dynamics

Christian Organizations & "Nice" Culture Challenges

The Politeness Trap

  • Well-intentioned desire to be nice and kind. (17:36)
  • Actual result: Handling conflict in ways that make things worse. (17:42)
  • Pattern: Indirect communication → triangulation → underground conflict. (17:51)

Example of Dysfunction

  • Instead of direct feedback: "You didn't deliver weekend work, what happened?" (18:24)
  • Polite version: "How was your weekend?" → "Busy" → No resolution. (18:29)
  • Consequence: Vent to others, create reputation problems, new people get "warned." (18:42)

The Matthew 18 Principle

  • Going direct is actually more kind than letting issues fester. (19:58)
  • Avoiding direct conversation creates underground conflict and unfair reputations. (20:10)
  • True kindness requires honest, direct engagement. (20:15)

Leadership Responsibility in Difficult Conversations

Patrick Lencioni's Point

  • It's the responsibility of servant leaders to have difficult conversations. (21:05)
  • Many leaders lack desire or courage to address issues directly. (21:13)

Identity Shift for Leaders

  • Old story: "I'm the person everyone loves working for." (21:46)
  • New story: "My job is to equip people to work well together." (22:22)
  • Servant leadership role: Catch issues early, name problems, bring people together. (22:42)
  • Key question: "How can we improve this?" (22:47)

Early Detection Approach

  • Spot problems early rather than waiting. (23:04)
  • Name issues directly but constructively. (23:19)
  • Focus on learning, growth, and change mindset. (23:06) 

Consequences of Avoiding Difficult Conversations

Organizational Costs

  • Innovation suffers: Blaming culture prevents risk-taking (24:22)
  • Employee disengagement: Unfairness perceptions, carrying others' workloads. (24:35)
  • Ripple effects: When bosses don't get along, it affects entire organization. (25:16)
  • High transaction costs: Work-arounds, blame avoidance, inefficiency. (25:54)
  • Talent loss: People leave rather than deal with dysfunction. (25:58)
  • Bottom line impact: Affects clients, customers, and service delivery. (26:51)

The Two-Layer Problem

Organizations typically face:

  1. Surface layer: Business issues (strategy, deadlines, client acquisition). (27:31)
  2. Deeper layer: How people feel treated in daily work interactions. (27:45)

Common mistake: Trying to solve feeling problems with business pep talks (28:17)

The Role of Emotions in Workplace Success

Feelings Drive Performance

  • People bring their "best selves" when they feel accepted and challenged. (29:01)
  • Ignoring emotions means people leave part of themselves at home. (29:25)
  • Result: Squandering huge percentage of available talent and capabilities. (29:32)

Professional Emotional Intelligence

  • Not about heated arguments or emotional blame. (30:28)
  • Focus: Reflective conversations about what's working/not working. (30:48)
  • Problem-solving approach that remains professional and direct. (31:14)
  • Addressing frustrations and anxieties constructively. (31:07)

Joint Contribution: Breaking Down Complex Conflicts

Moving Beyond Blame

  • Key shift: From blame to "joint contribution." (31:58)
  • Recognition: Everyone contributed something to current situation. (32:12)
  • Not about: Equal blame or fault-finding. (32:33)
  • About: Understanding how we got here and what needs to change. (32:54)

Contribution Analysis

  • What did each person do or fail to do? (32:16)
  • What external factors contributed? (market changes, resource constraints) (32:59)
  • How can we change contributions to get different results? (33:16)
  • Benefit: Enhances accountability without blame costs (33:29)

Essential Outcomes of Learning Conversations

Workplace Experience Transformation

  • Confidence: "Whatever happens, I'm not alone," (34:54)
  • Team unity: "We're all on the same team and will figure it out." (35:06)
  • Learning mindset: Being wrong isn't a big deal if we learn and improve. (35:41)
  • Early problem detection: Issues caught before becoming crises. (35:38)
  • Diverse solutions: Capitalizing on different perspectives and ideas. (35:40)

Business Benefits

  • Client satisfaction: Better outcomes and positive interactions even when problems occur. (35:52)
  • Talent magnet effect: People want to work where every interaction is positive. (35:57)
  • Competitive advantage: Especially important in low unemployment environment. (36:05)

Success Story Example

Contractor Turnaround

  • Contractor expected to be fired (38:03)
  • Used difficult conversation principles to prepare differently (37:40)
  • Result: Client changed mind, saying "You handled this so well, let's give it another shot" (38:09)
  • Demonstrates power of approaching conversations with learning mindset (38:27)

Personal Growth & Practical Application

Sheila's Personal Insights

  • Even experts fall into same traps: focusing on being right, blaming others (40:00)
  • Humility: Recognizing we all do things we advise against (40:10)
  • Progress: Having difficult conversations earlier in process (40:15)
  • Result: Fewer conversations escalate to crisis level (40:55)

Al's Key Learning

  • Leadership involves "moving to problems quickly." (41:30)
  • Don't back away from issues - engage them early. (41:35)
  • Earlier engagement prevents bigger problems later. (41:39)

     

Separating Intentions from Impact

Key Distinction

  • Assumption: Most people are well-intentioned, trying to do their best. (42:44)
  • Reality: Good intentions can still create negative impacts. (42:50)
  • Approach: "I don't know your intentions, but let's talk about the impact." (43:01)

Benefits of This Approach

  • Reduces defensiveness in conversations. (43:18)
  • Focuses on solvable problems (impact) rather than unprovable motivations. (43:10)
  • Gives people grace while still addressing real issues. (42:57)
  • Works whether intentions are good or not. (43:35)

The Invitation Approach

  • Key insight: Can only control ourselves, not others. (45:04)
  • Strategy: Invite others into different kind of conversation. (45:09)
  • Persistence: Keep offering better invitations for dialogue. (45:18)
  • Hope: It's rarely too late to turn around decades of frustration. (45:23)

Practical Implementation Advice

Starting Point for Complex Situations

  1. Map contributions: How did everyone contribute to current situation?
  2. Include external factors: What circumstances beyond individual control played a role?
  3. Identify changeable elements: What could each person do differently?
  4. Focus on future: What changes would create different results?

Resources for Further Learning

  • Website: triadlearning.com or diffcon.com
  • "Help Yourself" section: Additional reading, guides, worksheets
  • Book: "Difficult Conversations: How to Discuss What Matters Most"

Final Encouragement

The goal isn't to control or change others, but to invite them into more productive conversations. Even long-standing conflicts and damaged relationships can be turned around through persistent, skillful invitations to engage differently. The key is focusing on what we can control - our own approach and invitation to dialogue.



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