Why are difficult conversations so difficult? These 5 steps will help you nail the next one

Are you fearing starting a difficult conversation?  

If you answered ‘yes’, the news is that you are not the only one!  

A difficult conversation is a type of conversation where negative experiences, behaviours or uncomfortable topics will be discussed. These conversations aim to create a mutual understanding, build awareness, and start a process of change and improvement. It is not about winning or putting the other person down, but about getting out of an unpleasant situation and maintaining respect and dignity.

Sounds easy, positive, and constructive, so why are difficult conversations so difficult?  

One study from 2019 shows that more than 80 per cent of workers are avoiding at least one difficult conversation at work—a conversation they know is important but are dreading. In the same study, one in four people have put off their scary conversation for 6 months, one in 10 for an entire year, and another one in 10 admit to avoiding the conversation for more than two years. (VitalSmart, Crucial Learning)

Difficult conversations are even more difficult when the team is working remotely. Some of the leaders I work with share that they never met their team members face to face, and don’t know them that well, so they don’t feel comfortable enough challenging them when needed.

What are the main barriers for leaders to start a difficult conversation?

When working with leaders, the most mentioned reasons for delaying difficult conversations vary, but the following are present in almost all cases:

• The fear that they will upset someone. It is not easy to predict the reaction of the other person. What if they get upset or angry, and the leader doesn’t know how to navigate through the emotions? What if the behaviour in question worsens as an outcome of the conversation? At least now they know how to manage this – what if they need to take more difficult decisions after this conversation?

• The person might leave the company. It is an employee’s market out there, the tail end of the ‘Great Resignation’ and the rediscovery of ‘Quiet Quitting’. Yes, this is a real risk and leaders are afraid to challenge certain behaviours because the person might leave, and they cannot find a replacement. But what if they stay and continue working the same way?

• “I don’t feel prepared and confident holding such conversations”. This is a very valid one! Especially if the organisation doesn’t have a culture of open and constant feedback, leaders are not trained and the only time feedback is provided is during performance appraisal (yes, such organisations still exist).

Difficult and costly conversations

Avoiding difficult conversations is a costly ‘solution’.  It costs time, money and resources, and you might start seeing other employees leaving because things don’t go well.

The cost is not in money only but in decreased morale, engagement, trust, safety, and creativity.

The good news is that you can get better at giving constructive feedback and dealing with difficult conversations. It will take time and courage, and is best if there is someone more experienced or knowledgeable walking this journey with you. This can be a coach or a mentor.

“It usually takes me more than three weeks to prepare a good impromptu speech.” – Mark Twain

Preparation is the key!  

These are a few questions that will help you to prepare yourself before starting a difficult conversation. They will guide you on how to approach the situation, what to be aware of and what to avoid doing or saying. They are not a ‘panacea’ but a good start in how to not postpone difficult conversations.

1. What is the aim of the conversation? Think about what you want to get out of this situation and what the other parts want. Are you able to approach this conversation without blame or ego, and instead focus on solutions?

• Contribution. What is your contribution to the situation? Who else contributed to the situation? Consider why this conversation is difficult for you.

• Triggers. Think about what your current personal temperature is. When you know your temperature, you can be more aware of any potential triggers that might start you off on the wrong side of the conversation.

• Timing. How do you know when to have a difficult conversation? What do you need to have in place, so the time is right?

• Knowledge. What are the gaps in your knowledge about the situation and others involved? What else do you need to know before starting the confrontation?

Bonus tip – Treat difficult conversations as an opportunity. After all, they are a learning opportunity; the more you take the chance to practice, the easier it will get. Reflect on the conversation, the situation, and the outcome. What went well, what can you do differently next time? Self-reflection and self-awareness are key elements in leadership. You can find more about this in my previous article: 4 tips on how to build self-awareness and become a more inspiring and authentic leader