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  • Toby Sinclair

How To Lead Difficult Conversations

Updated: Mar 9, 2022

“When it comes to risky, controversial, and emotional conversations, skilled people find a way to get all relevant information (from themselves and others) out into the open.”

Kerry Patterson - Crucial Conversations

Difficult Conversations

Working on complex problems, in complex environments means that difficult conversations are inevitable. In fact, research has shown that encouraging the right conflict can lead to better product outcomes.

Common difficult conversations in the workplace include:

  • Poor employee performance or behaviour

  • Complaints and grievances

  • Giving bad news, such as ending employment or advising unsuccessful job applicants

  • Addressing conflict

  • Communicating tough business decisions.

The overriding emotion in most difficult conversations is fear and anxiety. Fear that you might upset someone, cause them emotional harm or negative consequences. This can create a huge amount of anxiety before, during and after a difficult conversation.

The result. Most leaders suck at difficult conversations.

Instead, leaders avoid them:

  • “I don’t want to hurt anyone’s feelings”

  • “Now is not the time”

  • “Everyone makes mistakes sometimes”

  • “I don’t have time”

  • ‘‘What’s the point, there’s never a good outcome”

  • “The problem will fix itself – just give it time”

When leaders avoid difficult conversations it has three side effects.

  1. The problem usually gets worse over time.

  2. The problem becomes normalised and people feel less incentivised to solve it. Compounding the problem further.

  3. Learning reduces. When the leader fails to role model handling difficult conversations well, the rest of the organisation don’t learn either.

Learning a few coaching skills can help you navigate these difficult conversations more gracefully.

Books To Navigate Hard Conversations

How Coaching Helps

Professional coaches are experts at having difficult conversations. They master a few skills to better navigate the tough moments. It doesn’t make the conversations easy, but the outcomes are typically better for everyone involved.

Because of this, it’s common for the most difficult conversations to be outsourced to a professional coach.

This is not optimal.

Instead, leaders need to learn how to become better at having difficult conversations.

There is no hiding the fact that these conversations will happen often and are required to reach high performance.

“The obstacle in the path becomes the path. Never forget, within every obstacle is an opportunity to improve our condition.”

The Obstacle Is The Way by Ryan Holiday

Learning how to coach

Leaders can learn from professional coaches how to navigate difficult conversations.

You don’t need to become a coach.

There are three skills you can copy from professional coaches. Listening, Asking and Sensing.

Here is how they help and how you can start using them today.


Every leader likes to think they are a “good listener” but very few are “great”.

In difficult conversations, you need to be a great listener. The challenge. It is in these moments listening is hardest.

In High Conflict, we have many more errors in judgement. It's hard to be curious whilst you are outraged.

The environment in which you have a conversation will influence how difficult it is.

To make it easier, prime the environment for listening. If virtual, close down email and notifications. Ask your team member to do the same. Find a time during the day that works for both. If you are doing it in person, find a neutral space. Outside the office often works and walk-and-talk can help.

Another way to listen better is using a technique called Looping. This is when you summarise and reflect back on what you have heard. It demonstrates to the other person that you have heard them. It also buys you time, stopping you from rushing to respond.

Looping is useful when there’s a misunderstanding you need to clear up. Looping follows a simple five-stage formula.

  1. When the other person has said something that you’re confused or unsure about, summarize what that person has said, and ask whether you’ve got it right.

  2. The other person will either confirm that you’ve got it right or will clarify what you’ve got wrong.

  3. You should then summarize what the other person has said including the new information, and ask that person to confirm you understand.

  4. The other person will either confirm that you understand or not.

  5. If you do understand, consider asking for more information. If you don’t understand, go back to stage one.


In high-pressure moments it’s easy to believe you must tell. To resolve the situation you need to “tell it how it is”. Direct and clear communication is important. But needs to be balanced.

In Radical Candor, Kim Scott shares a model for giving feedback. In difficult conversations, you need to find the balance of caring personally and challenging directly.

“Listen, Challenge, Commit. A strong leader has the humility to listen, the confidence to challenge, and the wisdom to know when to quit arguing and to get on board.”

Radical Candor by Kim Scott

It might seem counter-intuitive but difficult conversations asking questions can often lead to better outcomes. Making conversations two-way rather than one.

Asking a few questions has the following benefits:

  • It creates shared understanding. By asking and listening you’ll learn new information.

  • It demonstrates caring. That you want to hear and understand what the other person says.

  • It helps pace the conversation. Enable everyone involved to talk and share.

It’s important to avoid these common mistakes when asking questions.

The best way to ask more is to practice it in low-pressure moments. The one-on-one is a manager's best time to practice asking more questions.

My two favourite questions are:

  • What do you want to explore? Ask this at the start

  • What was most useful for you? Ask this at the end

When you become more comfortable asking questions, it becomes easier to ask them in high-pressure moments.

Coaching Toolkit


In difficult conversations, it’s important to stay present and aware.

This means being aware on four levels:

  • What's going on for you?

  • What's going on for the other person?

  • What's going on in the relationship?

  • What's going on in the wider system?

It is your ability to sense that guides you on how to act.

Difficult conversations share many characteristics but there is no single “best practice”. You can do the “right thing” and get the wrong result.

Being situationally aware helps you identify the most appropriate response. When to ask vs tell. when to speak vs listen. When to challenge vs care.

The challenge.

In high-pressure moments your senses will be alert to threats. Therefore it’s easy for defensive behaviours to take hold.

One way to reduce the threat response is to breathe. Take a few deep breathes to calm your body and mind. You are then more likely to listen and be open to asking questions.

Preparing for the conversation

If you’ve read this far, I’m sure there is a difficult conversation you’d like to have.

A little preparation can help ease your fears and increase your chances of success.

Here are 3 questions to help you prepare:

  • How will you prime the environment for listening?

  • What questions could you ask during the conversation? (write them on a post-it note)

  • How will you stay present and aware?


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