I no longer fear difficult conversations at work. And here’s why.

I remember just like it was yesterday. I was standing with my hands on my hips in the middle of my small office during a brutal heatwave. I was looking down at the young, upset man sitting on my weathered brown, leather couch. My office was normally a room I felt very comfortable in. But on this day, I didn’t.

That day I was having a very difficult conversation with this young man who was an employee. I’d had difficult conversations before with both customers and employees but this one was very different. When the conversation ended, I knew the sweat trickling down my back wasn’t from the stifling heat. I realized the sweat was because I knew nothing about how to have a proper difficult conversation at work. Everything I knew about having difficult conversations up to that day was based on what I had adapted from my personal life.

And in the work environment that simply wasn’t enough.

Customers, Colleagues, Team Members, and Bosses

What you’re going to learn in this article are universal tools that you can use in all types of difficult conversations that you need to have at work – with customers, with colleagues, with team members, and with bosses.

These tools are designed to help you build your confidence whenever you need to reach out to someone and have a challenging talk. And your new confidence will allow you to enter any difficult conversation at work and know that you can handle it, just fine.

Before the Difficult Conversation Part 1

A little prep work in advance of your challenging talk can make the world of difference. It lays the groundwork for a conversation that flows smoothly like a fresh paved road versus a talk that is bumpy like a pothole-filled road.

The tool that helps lay the foundation for a smooth difficult discussion is the Intro Statement.

The Intro Statement helps set the tone of the conversation. In just a few sentences, it raises the main issue that’s going to be the focus of the discussion and sets the agenda.

The Intro Statement includes:

  1. a quick lead in to start the conversation
  2. the main issue to be discussed
  3. a specific example that illustrates the main issue
  4. clarification of what’s at stake
  5. your contribution to this issue
  6. your wish to resolve the issue
  7. an invitation for the customer to respond

Here’s an example:

  1. The lead-in
    I appreciate you joining me on this call today.
  2. The main issue
    I wanted to talk to you about increasing the adoption of our platform across your team.
  3. A specific example that illustrates the main issue
    We’ve noticed that 5 people on your team regularly use our product but the remaining 11 rarely use it.
  4. Clarification of what’s at stake
    I’m concerned that you may never hit that ROI you’re looking for. There’s a real risk to our partnership if we’re being measured on our ability to drive that ROI.
  5. Your contribution to this issue
    Maybe the materials I’ve sent you weren’t specific enough to your situation.
  6. Your wish to resolve the issue
    Even though this might be a tough issue to address, I hope that we can have this conversation in an open and collaborative way so we can find some helpful solutions.
  7. Invite the customer to respond
    What do you think?

In the beginning, you’ll want to write this Intro Statement out and practice it. Writing out the Intro Statement gives you clarity on the issue at hand and identifies why this issue is so important to discuss and resolve.

As you can see, the Intro Statement is a simple tool that frames and focuses the conversation very clearly. It’s the foundation for a smooth discussion. Practice reading your Intro Statement out loud several times a day to get comfortable with its flow. When you read your Intro Statement at the beginning of your difficult conversation, you want it to sound as natural as possible.

Over time, the Intro Statement will become like second nature to you, and you won’t need to practice it at all.

But until then, practice, practice, practice becoming comfortable with your Intro Statement before every difficult conversation you’re about to have.

Before the Difficult Conversation Part 2

Just like getting nervous before public speaking, knowing you are about to enter a difficult conversation can raise a big range of emotions, from fear to anxiety. This is very normal and to be expected.

Most people feel very nervous about using the Intro Statement for the first time.

The first few times a person undertakes a new way of doing things, a lot of mental effort is required to remember the steps.

Just think back to the first time you drove a car – you were very consciously paying attention to a lot of things like your speed, your mirrors, where you were in the lane, where other cars were relative to your car, and how hard you had to step on the gas and the brake pedals.

Now you get in your car and just drive. Those things have now become unconscious because you’ve practiced driving so many times.

Having difficult conversations at work is no different than learning how to drive.

Eventually, you won’t have to spend so much focused mental energy using the tools you learned in this article. Instead, you’ll become more comfortable with having challenging discussions because you’ll have practiced using the tools. You will also become more confident too.

Until you become more comfortable having difficult conversations, here are some tools to help you prepare for your difficult conversation:

  1. Take a few deep breaths to calm your nerves
  2. Get water and have it near you
  3. Question any fears that might be popping into your head.
    Ask yourself:
    Are these fears true?
    Can I put them to the side for now?
  4. Practice your Intro Statement
  5. Remind yourself that, over time, having difficult conversations will become easier.

After the Difficult Conversation

Taking a few minutes after your difficult conversation to reflect will help you speed up becoming more comfortable and confident in your future challenging discussions.

Build in a 15-minute window after your first 5 conversations to debrief.

1. Give yourself a pat on the back
You did it!
You likely made mistakes and that’s ok.

Using the Intro Statement will feel very mechanical and hard at first. The more you practice using the Intro Statement, the more natural it will feel. (Remember, it’s just like driving a car for the first few times.)

2. Take a few minutes and ask yourself these 3 questions:

Did my Intro Statement sound natural or did I sound a bit awkward?
Did I let my fears rise up and affect the direction of the conversation?
Did I cover all the points in my Intro Statement?

Asking yourself these 3 questions will help you determine areas of opportunity for future challenging conversations.

3. What needs to be followed up?

a) If it’s appropriate, send a thank you note/email/message to the person(s) you just had the difficult conversation with. Let them know you appreciate the effort it took on their part to participate. You’d be surprised how this small gesture can deepen the relationship.

b) Write a list of follow-up items. Is there someone else you need to speak with about this situation? Did you promise to take certain actions? If so, write them down and be sure to follow up.

c) Are there any other actions or steps you need to take?


I wish I had these tools when I was having that difficult conversation all those years ago. That young employee sitting on my brown, leather couch in my sweltering office was my nephew. And I was giving him a warning about his attitude on the job.

If I had known about the Intro Statement and learned to calm myself down before the talk, I wouldn’t have let those fear-laden words just fall out of my mouth. Unfortunately, not having these tools lead to a damaged professional and personal relationship.

I now know better and do better.
And you can too.

Originally published in CS Insider.