How would you stand up to your boss without committing career suicide?
How would you critique your colleague’s work?
How would you confront your loved one about the abuse problem?
These are difficult, but crucial conversations.
Do you tend to avoid them, go silent and shutdown? Or perhaps you tend to lose cool, and go violent and emotional? Could you handle these conversations better?
I can give you some hints for improvement, at least point you in the right direction.
Here you are:

There are only a few books which had a significant impact on my life. One of them is “Crucial Conversations: Tools for Talking When Stakes Are High” by Kerry Patterson, Joseph Grenny, Ron McMillan, and Al Switzler.
You would think that “crucial conversations when stakes are high” are conversations where everyone is calm, composed, and hyper-attentive. In reality, when stakes are high, people often become irrational, emotional, and deaf. The higher the stakes, the more likely the conversation will turn ugly.
That was my first “A-ha!” moment from the book, and there are many more like that in there. I highly recommend the publication – I gifted it to a lot of my friends. It will give you a framework and tools to handle difficult conversations.
Here is my summary of the most powerful insights:
1) Learn to look. Look for then you or others move from dialogue into silence or violence.
2) Make it safe. If the dialogue has stopped, then do something to restore safety.
More than once, I had difficult stakeholders, who would go violent, offend me or my teammates, call names, discredit, etc. Instead of going defensive, or silent (with labelling like “oh, they are just d-head”)… I would recognise that dialogue has stopped, and most likely safety is an issue. In a professional setting, safety issues are usually someone’s reputation or resources. So, I would be curious and try to identify what the real issue is, and how my actions may threaten someone to look bad in front of others, or perhaps I am demanding significant effort or time from their side. There are several ways to restore safety. Once you notice the issue, it is easy to find the correct action.
By doing that, I would be able to pinpoint the source of tension, address it, and resolve the conflict. That does not mean bowing and bending to others’ demands. It’s totally possible to be frank and respectful at the same time. Often it means just providing reassurances, addressing their concern in some form or shape, or small concessions from both sides. The change in behaviour and relief would be so strong that you would start gifting the book to your friends as well.
Nowadays, I don’t get into many situations like that. I’d like to think that I am getting better at listening and anticipating safety issues.
When having a difficult conversation, it is also important to separate facts from the story, watch for villain/victim narratives, and ask the other to share their view. Here is how would you structure a conversation with a micro-managing boss, for example:
- Have a private 1:1 setting to ensure the safety of your boss’ reputation
- State the facts: “On this day you asked me to run all client emails past you, on that day you made 10 back-and-forth modifications of my report, on that day you corrected me in a team meeting for a minor matter”
- Tell your story: “All that makes me feel uncomfortable, and it looks like you don’t have enough trust in me”
- Ask their story: “How does it look/feel from your side?” “What are your thoughts?”
- Dialogue. Look if it moves away from being dialogue. Restore safety if required.
- Finish with an agreement: For example – if the boss lost trust due to past errors on your side, then you may have an agreement that they will give you a chance to restore trust by giving you autonomy in certain areas while retaining, perhaps some oversight in other areas.
That will give you what you want. And here is one more gem from the book – know what you want. You don’t want to “win” or be “right”. You want concrete results like freedom of actions, fair treatment, or productive relationship.