Difficult Conversations

Speaker: Paul Kenny (@PaulKennyOL)

The success of your business depends on your ability to step up and have the difficult conversations.

When you hire smart people with strong opinions–which you should–then the success of your business depends on your ability to manage those people by having difficult conversations.

What makes a conversation difficult?

  • Standards are challenged
    • Leaders set standards: behaviors, processes, etc.
  • Impediments to progress
  • Clash of perspective
    • Just a few degrees of difference can make a huge difference down the line
  • Emotionally difficult to process
  • Ego depleting

Reasons for Difficult Conversations

  • Priorities
  • Performance & Reward
  • Promises
  • Zones of Control
  • Perceived Lack of Effort
  • Unpopular Tasks
  • Technical Differences

Conversations Exacerbated By

  • Customer Demands
  • Stress
  • Opinions
  • Work Style
  • Clash of Egos
  • Personal Loyalties
  • Tactical Differences

The web of human interactions in your business is the mode complex issue you will face. The answers to all your product & customer issues begin here.

Difficult conversations can help to avoid common startup failures.

As leaders, the organization around us is defined as much by what we don’t do and don’t say as much as what we do do and do say.

Small issues can become totemic–symbols of larger issues. People may mention these smaller issues, but they reflect larger issues.

With unspoken conversations, the situation rarely gets better, it just gets later. Though we often rationalize that the situation will get better.

Unresolved issues divide staff and create cliques. People are by nature, tribal. They will choose sides when there is an open unresolved issue.

In any business, we can have discussion in three zones:

  1. Zone of Comfortable Debate
  2. Zone of Uncomfortable Debate
  3. Heart of the Matter: The Elephant in the Room

A sign of a strategically mature business is one that has become able to have conversations in the zone of uncomfortable debate. Most startups don’t fail because people are dumb. They fail because people don’t want to have an uncomfortable debate critical to the business.

Why do we not have difficult conversations?

Our colleagues are our friends.

Every time you have a difficult conversation, there is a perceived time penalty and a perceived talent penalty.

To avoid difficult conversations, we do mind-reading and create catastrophic scenarios.

Tactics for Difficult Conversations

  1. Develop Perspective
    1. Often it’s not whether we paint the product red or blue. It’s about how we approach the problem
    2. Learn the preferences of how people like to interact
  2. Be Aware of Your State
    1. Everybody goes into every conversation in a particular state. If you or the other person go into the conversation in a specific state, you tend to match specific behavior patterns:
      1. Wisdom -> Sage
      2. Clarity -> Visionary
      3. Creativity -> Magician
      4. Balance -> Steward
      5. Stress -> Warrior (take the offensive)
      6. Anxiety -> Politician (tell people what they want to hear)
      7. Fear -> Casualty (play the victim – learned helplessness)
  3. Always Have the Conversation (Never Procrastinate)
  4. Remember You Can Only Change Behaviors
    • Cannot ask people to be more motivated
    • People generally don’t do behaviors for no reason
  5. Take Responsibility for Your Perception & Feelings
    • Don’t fudge the issue by saying “others have noticed”. If you noticed it, take responsibility and say “I noticed”. Focus on:
      • What I noticed
      • What I believe
      • How I feel
    • Focus on the behavior, the observable actions, not the underlying motivations. For example:
      • Behavior: I noticed this
      • Consequences: This is the consequences
      • Options: These are our options to fix the problem
      • Next Steps: These are our next steps
  6. Create Team Rules
    • Easier to hold people to rules & standards they created themselves
  7. Find Interesting New Ways To Address Contentious Issues
  8. Make Process Reviews As Regular as Progress Reviews
  9. Don’t Be Afraid To Ask a Third Party to Help
  10. Stay Adaptable (Position vs Principle)
    • Never forget to listen

Courage is what it takes to stand up and speak; courage is also what it takes to sit down and listen. – Winston Churchill

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