How To Handle Difficult Conversations

18th Oct 2022

How To Handle Difficult Conversations

‘Hard skills help you find jobs, but soft skills will help keep them.’ 

Knowing how to approach and handle difficult conversations is a vital ‘soft’ skill that will help you better navigate the workplace and the world beyond it. 

Inspired by the book ‘Crucial Conversations - Tools for Talking When the Stakes are High’, we've got some top skills for avoiding conflict and handling tough conversations.

So, if quality of life, the health of the organisations you are part of (work or personal), and the strength of relationships seem like something you may be interested in, then this might be of use to you.

What are Crucial Conversations?

Crucial Conversations are encounters that find themselves at an intersection between opposing opinions, strong emotions & high stakes. Some examples of these would be; 

  • Asking a colleague to repay a loan 
  • Talking with your boss about not getting an increase or bonus 

Or scenarios that take place outside of work, such as; 

  • Talking to your teenager about breaking curfew consistently, lying, or not doing homework. 

Crucial conversations stem from disappointment. They are required when there was a missed commitment, broken promise, missed expectation or other bad behaviour. It all starts with 'Why didn't you do what you were supposed to do?' and 'Why didn't you behave the way you were supposed to behave?' These moments are going to happen. The problem isn't that these moments occur. 

The problem is that we are unsure of how to address them. The framework for a crucial conversation is simple. What you do BEFORE, DURING, and AFTER

Let’s breakdown what needs to happen at each step; 


Two important steps to follow when approaching a crucial conversation are; 

1. Master your story - When someone behaves in a certain way, we are likely to create our reasoning for why they did it. This then leads to a feeling and a reaction - all of which was fabricated in our heads. This will often influence how we approach the conversation before we know any of the facts. A rule to live by is ‘get curious before you get angry’. Wait until you know exactly why something happened before you start to make judgements. 

2. Address the right problem - If you do not address the problem, the issue will never be resolved. Let’s use the example of a teenager missing curfew. Would you be angry that they arrived at 11 PM? Or would you be angry that they broke a promise that was made? The time is irrelevant. The main issue is that they failed to uphold their side of the deal, and the trust you gave them has been taken advantage of. 

The ability to reduce an infraction to its bare essence takes patience and precision. People often don't have time to unbundle the problem as there are too many emotions involved. The rule is that you must distil the issue to a single sentence before you talk. 


The three steps to follow during the interaction are; 

1. Confront with safety - Your behaviour in the first few seconds of an interaction sets the tone for everything that follows. You have no more than a sentence or two to set the climate. It's known as The Hazardous Half Minute. Your choice of words, tone, and demeanor can be used to show mutual respect and create safety between participants. A safe atmosphere ensures that all parties will be comfortable to engage without being defensive. This can also be achieved by creating a mutual purpose (us instead of you). Lastly, ensure that these conversations take place in private. 

2. Describe the gap - Start with only the facts. Describe WHAT happened. Not your assumptions as to WHY it happened. Then describe the gap/difference between their expected behaviour and what took place. Lastly, end with a simple diagnostic question such as “Why did this happen?”. This will ensure that the safety you have created is maintained and will allow them to share the reasoning behind their behaviour. 

3. Diagnose - The way someone responds to your description of the gap will determine what you do next. Now you need to diagnose the underlying cause of the problem. Is it a matter of motivation, ability, or both? It is important to understand that everyone is motivated by different things. Discovering what motivates a particular person will be your greatest point of leverage in making them realize their errors and adjusting their behaviour. Do not use short term fixes such as perks or power. Every time we compel people to bend to our will, it creates a lonely work environment. Be careful with perks as it takes attention away from the legitimate reason to do something. 

4. Agree on a plan - Now you need a plan! Agree on who will do what, and by when. It is then important to set up a follow-up time to check how things are going. Simply end with ‘Can I rely on you to...?’. 


1. Follow up -  It is vital that you follow up to ensure that both parties have stuck to the plan. Following up will also allow you to reanalyse the situation and ensure that any additional gaps in ability or motivation can be address and corrected. 

2. Praise - If expectations are now being met, it is vital to reinforce that behaviour with acknowledgement and praise. Do not underestimate how powerful these words can be.

By following these steps, you will be able to navigate difficult conversations with precision.