Tricky Conversations

Things don’t turn to custard suddenly. We usually arrive in that place slowly – one failed or 'failed to have' conversation at a time. 

Nobody likes to have them. Mostly we avoid having them because nobody has taught us how. We fear that we will get it wrong, make it worse, or get criticised. We hope it will go away or someone else will do it. So what do we do if a tricky conversation has our name on it?



  • Disruptive behaviour improves
  • People re-engage and actively participate when underlying issues get addressed
  • Things left unattended don’t pollute other parts of the organisation - niggles don’t turn into elephants 
  • The tone of the organisation goes from being prickly or ‘dull’ to alive and interactive
  • Everyone can breathe out when assumptions are dispelled and misunderstandings are straightened out – no more walking on egg shells

Types of tricky conversations

  •     Performance management
  •     When mistakes keep happening
  •     Asking for what we want
  •     The elephant in the room conversations 
  •     Revisiting a rubbish conversation
  •     When we screw up
  •     With your manager or boss
  •     When we disagree
  •     Unhappy customer / client
At its core, what Jane does is open up honest conversations, in a real-world, practical manner. What my staff and I took away could be used immediately. Actually, I keep a copy of the seminar summary notes in my desk and look it over before any tricky conversation.
— Tim O’Connor, Principal, Auckland Grammar School