How to Confront Situations You Should Have Dealt with Sooner

If you think it’s difficult to have a tough conversation today, waiting makes it worse.

Time makes elephants fat, complacent, and harder to confront.


It’s not patient to tolerate poor performance. It’s neglect.  Poor performance, bad behaviors, and difficult situations continue until leaders speak up.

Be patient after you bring up issues.

The conversation you should have had:

Kind candor and courageous vulnerability chart the path forward, when you should have said something sooner.

#1. Don’t lay the law down. Delay elevates frustration. Anger fuels courage. You end up sharing a piece of your mind you can’t afford to lose.

#2. Don’t speak to the whole team when there’s one offender. One person habitually leaves early, arrives late to meetings, or misses deadlines. Have a one-on-one, even though group comments feel safer.

#3. Meet resistance with courageous vulnerability. Tom habitually misses deadlines, for example. When you bring it up, he protests. “Why didn’t you say something sooner?”

Tom is right.

Don’t defend or explain. Apologize.

“You’re right Tom. I apologize for not bringing this up sooner. Tolerating this wasn’t fair to you or the team. I’m dealing with it now. Can we fix this?” Wait for Tom to say, “Yes.”

Resistance turns to participation with “Yes”.

4 Tips:

  1. Build positive relationships. Have lots of positive conversations.
  2. Bring up issues when issues are small. “I notice you missed your last deadline.”
    • What are you learning?
    • What will you do next time?
    • How can I help?
  3. Take excuses seriously. When Tom says, “I’m terrible with time management,” ask, “What would you like to do about that?”
  4. Develop a plan to solve issues. Don’t simply declare that you expect things to change.

Patience with poor performance eventually becomes permission to perform poorly. Approval becomes abuse.

How might leaders have the tough conversation they’ve been putting off?