An Actionable Approach to Tough Issues Even Timid Leaders can Employ

The worst agonies of leadership are self-inflicted.

Poor results and toxic environments are often the result of misplaced tolerance.


Silent tolerance is unspoken approval.

What happens when you avoid tough issues:

#1. Unintentional affirmation of negative behaviors.

Silent tolerance is unspoken approval.

Teams embrace negative behaviors that leaders tolerate.

Tolerance is endorsement. Endorsement becomes encouragement. Negative behaviors allowed in moderation eventually become harmful patterns and destructive habits.

#2. Temporary comfort from false compassion.

Tolerance of negative behaviors isn’t compassion.

Real compassion confronts. False compassion avoids. Kim Scott calls false compassion ‘ruinous empathy’ in her book, Radical Candor.

It’s cowardice, not compassion, to silently permit self-inflicted injury.

#3. Nagging frustration and escalating stress.

Everyone who avoids tough issues experiences nagging frustration.

Addressing frustration:

  1. What’s frustrating about this? Listen and affirm. Don’t solve.
  2. How have you tried to resolve this frustration? If the answer is nothing, go to #3. If they’ve tried and failed, go to #4.
  3. What have you tried to resolve this issue?
  4. What else might you try?
  5. How can I help? Only ask this question if you’re prepared to help someone address their tough issue.

Tip: Use the above questions to reflect on your own nagging frustrations.

Stay open to the idea that you contribute to the nagging frustration of others.

#4. Squandered potential and misspent resources.

Unaddressed issues distract from peak performance.

You’re never at your best when you avoid tough issues.

An actionable approach to tough issues:

  1. Ask questions before casting blame or offering solutions. Forward-facing curiosity is freedom to bring up tough issues.
  2. Always seek to advantage others and your organization. Causing harm is never an option.
  3. Define positive outcomes before developing solutions. What do you want?
  4. Generate multiple solutions before choosing a simple path forward.

The negative issue you ignore control you.

Tolerating tough issues becomes learned helplessness.

Bonus material:

Managing in the Gray (Book)

5 Steps to Tackling Difficult Conversations (CCL)

Resolve Your Toughest Work Problems with 5 Questions (HBSWK)