How to Handle Difficult Conversations at Work

How to Handle Difficult Conversations at Work

A practical, focused workshop for first-time managers who know a conversation matters but aren’t sure how to begin.


Walk away with a clear decision and a written plan you can actually use.

A practical, focused workshop for first-time managers who know a conversation matters but aren’t sure how to begin.


Walk away with a clear decision and a written plan you can actually use.

In this 60 minute workshop, you’ll decide whether the conversation is actually needed and leave with a simple, written plan for how to open it clearly and fairly. As well as a simple process you can use for future conversations.

Do you keep replaying a conversation in your head, knowing it needs to happen, but not quite sure how to start it?

Are you stuck between wanting to be clear and worrying it will damage the relationship?

Have you read advice on difficult conversations but struggled to apply it in real situations?

This Isn’t About Scripts Or Saying The “Perfect” Thing

You can find plenty of advice on difficult conversations. The missing piece is how to think before you speak. Most conversations go wrong not because people lack courage, but because they don’t have clarity about what’s really going on.

They’re not sure if the conversation is really needed, what the real issue is, how firm is fair, or what they’re responsible for. That leads to overthinking, softening, and avoidance.

This workshop helps you slow down and clarify your judgement so you can approach the conversation calmly and fairly — without making it worse.

What Others Are Saying

We believe in this work because we’ve seen the difference it makes.. Here’s what clients say about working with Andy. These testimonials are from coaching engagements.

  • I would strongly recommend Andy's coaching services to anyone who wants to increase their impact + performance in a way that prioritises integrity and self-awareness.

    Julian Ng

    Lawyer

    men's gray crew-neck shirt
  • I would recommend Andy without hesitation. He is an outstanding business coach, trustworthy, reliable and honest.

    Tim Lynas

    Chartered Surveyor

    Tim Lynas
  • I know a big part of the success of my company is because of Andy walking with me through this journey.

    Jay Tran

    Creative Director

    Jay Tran
  • He has a lot to offer and I would definitely recommend him to anyone who wants a coach.

    Cathy Bates

    Managing Director

    Cathy Bates
  • I would strongly recommend Andy's coaching services to anyone who wants to increase their impact + performance in a way that prioritises integrity and self-awareness.

    Julian Ng

    Lawyer

    men's gray crew-neck shirt
  • I would recommend Andy without hesitation. He is an outstanding business coach, trustworthy, reliable and honest.

    Tim Lynas

    Chartered Surveyor

    Tim Lynas
  • I know a big part of the success of my company is because of Andy walking with me through this journey.

    Jay Tran

    Creative Director

    Jay Tran
  • He has a lot to offer and I would definitely recommend him to anyone who wants a coach.

    Cathy Bates

    Managing Director

    Cathy Bates
  • I would strongly recommend Andy's coaching services to anyone who wants to increase their impact + performance in a way that prioritises integrity and self-awareness.

    Julian Ng

    Lawyer

    men's gray crew-neck shirt
  • I would recommend Andy without hesitation. He is an outstanding business coach, trustworthy, reliable and honest.

    Tim Lynas

    Chartered Surveyor

    Tim Lynas
  • I know a big part of the success of my company is because of Andy walking with me through this journey.

    Jay Tran

    Creative Director

    Jay Tran
  • He has a lot to offer and I would definitely recommend him to anyone who wants a coach.

    Cathy Bates

    Managing Director

    Cathy Bates
  • Working with Andy constantly felt like I had a cheerleader and someone to challenge me in the right ways.

    Junelle Ayetty

    Trainee Solicitor

    Junelle Ayetty
  • He coached me on how to improve people skills such as communication, presentation, people management. I would highly recommend him as a management guru.

    Dheeraj Kumar

    Mechanical Design Engineer

    Dheeraj Kumar
  • What Andy does is bring out the best in what you have to offer the world and to reach your true potential in life in whatever it is you want to achieve.

    T.C.

    Company Director

    Terry Chiu
  • To be coached by Andy is to be in safe hands, which makes courage seem more possible. I'm very pleased to commend him to individual clients and any organisation would be lucky to have him.

    Dr. Robert Nettleton

    Nurse, health visitor and educator

    Robert Nettleton
  • To be coached by Andy is to be in safe hands, which makes courage seem more possible. I'm very pleased to commend him to individual clients and any organisation would be lucky to have him.

    Dr. Robert Nettleton

    Nurse, health visitor and educator

    Robert Nettleton
  • Working with Andy constantly felt like I had a cheerleader and someone to challenge me in the right ways.

    Junelle Ayetty

    Trainee Solicitor

    Junelle Ayetty
  • He coached me on how to improve people skills such as communication, presentation, people management. I would highly recommend him as a management guru.

    Dheeraj Kumar

    Mechanical Design Engineer

    Dheeraj Kumar
  • What Andy does is bring out the best in what you have to offer the world and to reach your true potential in life in whatever it is you want to achieve.

    T.C.

    Company Director

    Terry Chiu
  • To be coached by Andy is to be in safe hands, which makes courage seem more possible. I'm very pleased to commend him to individual clients and any organisation would be lucky to have him.

    Dr. Robert Nettleton

    Nurse, health visitor and educator

    Robert Nettleton
  • To be coached by Andy is to be in safe hands, which makes courage seem more possible. I'm very pleased to commend him to individual clients and any organisation would be lucky to have him.

    Dr. Robert Nettleton

    Nurse, health visitor and educator

    Robert Nettleton
  • Working with Andy constantly felt like I had a cheerleader and someone to challenge me in the right ways.

    Junelle Ayetty

    Trainee Solicitor

    Junelle Ayetty
  • He coached me on how to improve people skills such as communication, presentation, people management. I would highly recommend him as a management guru.

    Dheeraj Kumar

    Mechanical Design Engineer

    Dheeraj Kumar
  • What Andy does is bring out the best in what you have to offer the world and to reach your true potential in life in whatever it is you want to achieve.

    T.C.

    Company Director

    Terry Chiu
  • To be coached by Andy is to be in safe hands, which makes courage seem more possible. I'm very pleased to commend him to individual clients and any organisation would be lucky to have him.

    Dr. Robert Nettleton

    Nurse, health visitor and educator

    Robert Nettleton
  • To be coached by Andy is to be in safe hands, which makes courage seem more possible. I'm very pleased to commend him to individual clients and any organisation would be lucky to have him.

    Dr. Robert Nettleton

    Nurse, health visitor and educator

    Robert Nettleton

What We'll Work Through

This workshop is deliberately focused.

Rather than trying to cover everything about difficult conversations, we’ll slow down and work through one clear preparation process together.

You'll leave with:

Clarity on whether this conversation needs to happen

Clarity on whether this conversation needs to happen

Clarity on whether this conversation needs to happen

A focused understanding of the real issue

A focused understanding of the real issue

A focused understanding of the real issue

A simple plan for how to open the conversation with confidence

A simple plan for how to open the conversation with confidence

A simple plan for how to open the conversation with confidence

A calm, simple opening — not a script, just a starter that feels grounded and fair

A calm, simple opening — not a script, just a starter that feels grounded and fair

A calm, simple opening — not a script, just a starter that feels grounded and fair

Throughout the session, the focus is on clear thinking before you speak. There’s no performance, no role-play, and no pressure.

You’ll leave with a written plan you can trust — and a way of preparing for future conversations when they come up.

In 60 minutes, you’ll know whether the conversation needs to happen, what it’s really about, and how you can open it in a way that’s fair, calm, and proportionate.

In 60 minutes, you’ll know whether the conversation needs to happen, what it’s really about, and how you can open it in a way that’s fair, calm, and proportionate.

In 60 minutes, you’ll know whether the conversation needs to happen, what it’s really about, and how you can open it in a way that’s fair, calm, and proportionate.

Hey There, I’m Andy Lee

I help first-time and accidental managers who were promoted for their technical skill — but never given clear guidance on the people side of the job.

Most of the managers I work with care deeply about doing the right thing, want to be fair, and take responsibility seriously. What they weren’t given was a clear way to think about the human side of daily work. I know that position well — I’ve been an accidental manager myself, and over the last 20 years I’ve supported managers in corporate environments, startups, and fast-moving teams.

What people tend to thank me for isn’t motivation or confidence tricks. It’s clarity — clarity about what actually matters in a situation, what their role requires, and how to take the next step calmly and confidently. This workshop is built on that same approach.

A calm, practical workshop to help you think clearly before a difficult conversation

A calm, practical workshop to help you think clearly before a difficult conversation

A calm, practical workshop to help you think clearly before a difficult conversation

Frequently Asked Questions

Frequently Asked Questions

Is this workshop suitable if I’m very new to management?

Is this about scripts or what to say word for word?

What if I already know I need to have the conversation?

Will this help if the other person reacts badly?

Is this therapy or coaching?

What’s included with the ticket?

Is this a sales pitch for something else?

What if I decide it’s not for me?

Is this workshop suitable if I’m very new to management?

Is this about scripts or what to say word for word?

What if I already know I need to have the conversation?

Will this help if the other person reacts badly?

Is this therapy or coaching?

What’s included with the ticket?

Is this a sales pitch for something else?

What if I decide it’s not for me?

Is this workshop suitable if I’m very new to management?

Is this about scripts or what to say word for word?

What if I already know I need to have the conversation?

Will this help if the other person reacts badly?

Is this therapy or coaching?

What’s included with the ticket?

Is this a sales pitch for something else?

What if I decide it’s not for me?