How to have Difficult Conversations

How to have difficult conversations

In the previous episode (EP44) of The Root of All Business, I had the opportunity to have a discussion with Communication Skills Expert Clare Samuels on How to have Difficult Conversations.

Clare runs her own training company, No “i” in Clare, and uses actors, humour and expert facilitation to bring training to life. Her mission is to help people become more confident and effective communicators.

She spends her time working with lots of different companies in many various Industries; she is quick to point out, “it doesn’t matter where you work or what your role is, there will always be difficult conversations to have”.

Indeed, some of the typical ones she came across, are Managers wanting to get people on board with a new process. Facing their team’s resistance to change, it is easy for managers to feel frustrated they “aren’t just getting on with it”. Clare tells me there is something valuable in a Manager truly listening to why people aren’t buying into the process and sitting down to have a 1-1 discussion around this


Prepare to Face a Difficult Conversation

conversation between boss and employee

Some top tips from Clare:


1. Use emotional intelligence. Manage your own emotions since it can be challenging to have a conversation with somebody else. If you go in anxious, stressed, or worried, it can get to you no matter how much you persuade yourself that it won’t. It will be evident from your body language, and the other person will pick up on that straight away.

2. Be an active listener. Observe their body language, listen to their tone of voice, do not interrupt, ask lots and lots of questions, find out their point of view before going in with yours.

3. Get the message out straight away. Don’t beat around the bush or go round the houses. Let them know immediately the topic of the conversation.

4. Find a comfortable environment. Make sure you go somewhere where nobody else can hear you.

5. Don’t make assumptions. Never assume what the other person is feeling.


TIP: It isn’t necessary to mention the subject matter of the meeting because they might worry about it for days.


The Feedback Model

make a list of what to say

Clare shares her techniques on how to deal with difficult conversations – prepared without being prepared.

First of all, you have to be emotionally ready and have real clarity of what to say. Follow this AID Feedback Model and write down a list for each:

  • Action
  • Impact
  • Do

Here’s an example:

1. Action– “I have noticed, three times in the past week, you were 20 minutes late.”

2. Impact – “The rest of the team can’t complete the workload by the end of the day, and will have to stay late.”

3. Do – “What I’d love you to do is to come in on-time.”

Once you get the feedback out on the table with AID, the hardest part is done. 

You may just engage in a simple coaching conversation once an employee explains their reasons for the “action” part.


You and your boss

conversation between employee and boss

Go in with the factsHow?

Take as an example one of the common issues employees – pay-rise.

Your boss gives you recognition for doing a good job but does not reflect in your Pay/Bonus. Now you want to justify yourself for the value you add to the business and receive what you deserve.

If this is you – what would you do?

Book a meeting with your line manager and go in with the facts/ evidence. Explain the brilliant projects you have have been involved in or have led.

Furthermore, show the feedback you received from all around the Organisation. Show evidence proving where you’ve added value to the company and how your project has financially added to the profits.

Specify the years with no pay-rise, be honest about feeling demotivated, and be frank about not wanting to find another job elsewhere, then directly ask for the pay-rise.

Then, shut up and hear what they have to say.


Follow-up on the matter

I believe in the importance of processes reviewed and improved. So if methods are discussed in your conversation, be open for follow-ups.



Coaching Culture within every Organisation

Coaching Culture within every Organisation

Many people have transformed from consultants to coaches. Therefore, since coaching is in “fashion”, how about using it as an approach?

Notably, there are individuals called “accidental managers” that exist in many organisations. They get promoted for the position untrained – specifically with people-skills.

Consequently, such micro-managers with a “Tell” Style can cause an Organisation’s profit to drop. Why? Due to demotivated or disillusioned employees. People at the top may filter down their dogmatic or dictatorial attitude, and it affects their employees negatively.

Thus, the coaching approach is the key to organisational success because the people involved are more likely to be open to questioning or enquiry, and open for best practice and knowledge sharing.


See “lightbulb moments”


Practice the coaching culture and witness as everyone benefits from that. Coaching has its power for someone who thinks he cannot build a rapport.

I believe that everyone has a coach in them; if you get in that space, you can build good healthy connections because it’s an open-mind thing.

Be the person to say, “I’m here, I’m here to listen, I’ll ask you questions, I’m going to explore”.

It opens up people to share their knowledge. If more managers and more leaders did that, organisations would thrive.


When is having a difficult conversation pushing the line?

disappointed person

Not everyone is open to difficult conversations; they want to protect their space and protect their ego. Such individuals may not have that clear self-awareness. 

Take in a specific scenario:

As you address an issue on hygiene with a particular employee, that individual might put it the wrong way. The conversation would be toxic; they would carry on with that message in mind with everything they do or in how they are being treated.




To avoid this from happening, we should take accountability. That means that the message is coming from YOU, not from anyone else. Avoid the “everyone is saying that…” phrase.

Concerning disabilities/medical issues, have a conversation with HR before doing anything to your people. They have more to say than you do.




What difficult conversation has Clare ever had?

Years ago, Clare had a different business (which she has subsequently sold), and she went to make a proposal for a potential client. So, she’s accompanied by a consultant, Jack, with an area of expertise.

She chatted with him beforehand and told him she would bring him into the conversation halfway through so he can discuss his “expertise” bit.

Immediately they got in front of the client he talked over her. It was like, “I’m here, I’m gonna sell to you, I’m the expert, I’m the Alpha Male”.

She had to shut him up during the meeting and make a joke out of the fact he kept interrupting her – They got the job.

BUT it was difficult for Clare to give her feedback after, to tell “Jack” how he made her feel.

The hardest part was he was unaware of how he came over and of course was gutted he had offended her.

“The build-up was even harder than the actual conversation.”, Clare says.


successful conversations

Hence, in life, we will always have to face that difficult conversation moment. We just have to be prepared.

Let’s sum up the key lessons on how to have a difficult conversation.


For you and your employee:

1. Use emotional intelligence

2. Be an active listener

3. Get the message out straight away

4. Schedule enough time

5. Find a comfortable environment 

6. Don’t make assumptions


Follow the AID Feedback Model and write down a list for each:


  • Action (what happened)
  • Impact (effect on the Team, project, and business)
  • Do (what they should do the same or do differently)


For you and your boss:

 Go in with the facts\ evidence:

  1. Successful Projects
  2. Value contributed to the business
  3. Feedbacks from the Organisation


We hope you picked up some tips and strategies you can implement, and I would love to hear what difficult conversations you’ve had.


PS: Clare and I are in discussions about an online workshop – if you would like to save the date – block out 22nd of April in your diary. Also, reply to this Email or visit Here! Let me know the key topics that would add the most value for you so I can discuss them with her.



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