top of page

Difficult Conversations 101

Having uncomfortable conversations at work is never easy. This is especially true for people who are afraid of conflict and would do anything possible to avoid it.

However, avoiding difficult conversations can actually lead to dysfunction and lack of performance, which can ultimately have a negative impact on a team and the business as a whole.

It is estimated that workplace conflict affects not only morale and productivity, but also turnover. A major study found that employees spend an average 2.8 hours a week dealing with conflict.

Instead of avoiding difficult conversations, find the courage to start confronting people in a constructive way, with skill and empathy.

Below we look at how to overcome fear of conflict and successfully approach uncomfortable conversations.

Before -

Choose the right place to have the conversation.

Calling people 'into your office' may not be the best strategy.

Sitting in your own turf, behind your desk, shifts the balance of power too much on your side.

Even simple body language, such as leaning forward toward the person rather than leaning back on your chair, can carry a subtle message of your positive intentions; i.e., "We're in this together. Let's problem solve so that we have a better workplace."

Consider holding the meeting in a neutral place such as a meeting room where you can sit adjacent to each other without the desk as a barrier. Don't exclude the coffee shop.


Before -

Step Into Their Shoes

Step into the other person's shoes to see where they come from.

  • What factors could be driving them to act/say/do things the way they are doing?

  • Why would you consider your stance to be the right one if you were them?

  • What is the other person looking to get out of the situation?

Knowing these viewpoints will help you create a win-win situation and deliver the message in a calm manner.


Before -

Remember to Pre-Position

Know how to begin.

Some people put off having the conversation because they don't know how to start.

The best way to start is with a direct approach. "John, I would like to talk with you about what happened at the meeting this morning when Bob asked about the missed deadline.

Let's grab a cup of coffee tomorrow morning to chat."

Or: "Linda, I want to go over some of the issues with XYZ customer and some concerns that I have. Let's meet tomorrow morning to problem-solve."

Being upfront is the authentic and respectful approach.

You don't want to ambush people by surprising them about the nature of the "chat." Make sure your tone of voice signals discussion and not inquisition, exploration and not punishment.


Before -

Focus On Creating Value

Confrontation suggests meeting someone face-to-face with hostile intent.

Examine what your true intent to having this meeting is.

If your intent is potentially hurtful to the other person, how can you look at this conversation differently?

Ask yourself, how can this conversation create value for me, for the other person, and for the company?


Before -

Understand Why This Is Important To You

If you need to have a conversation that is difficult for you, start with asking yourself why you really need to have the conversation.

  • Is it more difficult having the conversation or keeping the status quo?

  • You have the status quo now, so why bother?

When you can answer that question for yourself, you may find the conversation is not as difficult as you fear.


Before -

Be Confident But Open To Change

Before reaching out to the person who needs confronting, make sure you are not the one in the wrong.

If you go into a conversation expecting an issue, that's what you're going to get.

Have good intentions in your confrontation. Seek mediation if necessary.

Remember that your reputation will precede you, so communicate clearly and professionally.


Before -

Be Objective And Compassionate

Before you have the meeting, sit up straight, think of something positive, and take a deep breath.

You'll get through it.

Keep the conversation focused objectively, and share both insights and opportunities to improve.

You may want to start by saying, "I need to tell you something that might be difficult to hear."

Be compassionate to yourself and the person who is receiving your feedback.

Start -

Stick To The Facts

  • First, get clear on your intention/desired outcome.

  • Next, write out what happened and be sure to keep it factual.

  • Next, identify and take responsibility for your part in the situation. It will help avoid repeating an unwanted pattern.

With respect to approach, put yourself in the other person's shoes and think about how you'd want someone to approach you.

What would they say and how would they say it?


Start -

Show You Care

Wanting the best for the other person is a good place to start.

One of our basic needs is to be seen and cared for. Show interest in their feedback first, around the topic by asking,

  • "What are you doing well?"

  • "What are you not doing well?"

  • "What do you need to work on?"

  • "What do you need to change?"

Then give your feedback with the same questions. It's a two-way conversation and not a personal attack.


Start -

Make It Behavioural

Confront behaviour, not your assessment of their behaviour.

Confronting using inferences like "irresponsible," or "not a team player," causes defensiveness and makes success less likely.

Ask, "What is the evidence for my inference?" and confront on that behaviour.

Use, "When you do X, it causes me to think you are Y."

Plan before and maybe even practice so you keep your composure.


Start -

Use 'I' Statements

Starting your sentences with "I" avoids put-downs, judgement and blame, which are key to keeping your composure.

  • First, describe their behaviour by using, "When I hear you say..."

  • Then explain the feelings or thoughts it creates: "I feel/think ..."

  • Then note the effect their behaviour has: "It impacts..." I-statements promote a willingness to find a solution and seek constructive change without conflict.

During -

Prepare And Role Play

Most people hate to role play, yet it is an effective way to prepare for and practice tough conversations.

Write down what you want to say and be clear on the goal of the conversation: What do you want someone to leave with as an "a-ha" or action item?

Then, role play with a trusted peer.

He/she can give you feedback on what you say and how you say it. This helps build skills for future discussions.


During -


GRIT stands for Generosity, Respect, Integrity And Truth.

No one likes to be confronted. Most appreciate being helped.

When engaging in a conversation to help, our intent will come from a better place.

We won't feel like we're confronting the person, and our composure aligns more naturally.

I find it helpful to have an opening statement that portrays my intent. And then commit to being fully present and helpful throughout the dialogue.


During -

Be comfortable with silence

There will be moments in the conversation where a silence occurs.

Don't rush to fill it with words. Just as the pause between musical notes helps us appreciate the music, so the periodic silence in the conversation allows us to hear what was said and lets the message sink in.

A pause also has a calming effect and can help us connect better.

For example, if you are an extrovert, you're likely uncomfortable with silence, as you're used to thinking while you're speaking. This can be perceived as steamrolling or overbearing, especially if the other party is an introvert.

Introverts want to think before they speak. Stop talking and allow them their moment—it can lead to a better outcome. 

Ending -

Be consistent

Ensure that your objective is fair and that you are using a consistent approach.

For example, if the person thinks you have one set of rules for this person and a different set for another, you'll be perceived as showing favouritism.

Nothing erodes a relationship faster than perceived inequality. 

Employees have long-term memories of how you handled situations in the past. Aim for consistency in your leadership approach.

We trust a leader who is consistent because we don't have to second-guess where they stand on important issues such as culture, corporate values and acceptable behaviours.


Ending -

Preserve the relationship.

A leader who has high emotional intelligence is always mindful to limit any collateral damage to a relationship. It takes years to build bridges with people and only minutes to blow them up.

Think about how the conversation can fix the situation, without erecting an irreparable wall between you and the person. 

There are two keys to having productive difficult conversations:



Preparation is key.

Try to bear this in mind when the need arises.


ACAS have produced an excellent guide to this subject that can be accessed HERE

2 views0 comments


bottom of page