How to make difficult conversations easy

“He has asked me for a pay rise and I just don’t know how to say no.”

This was what I was asked in a coaching session earlier today. The person I was coaching is an established, credible and senior leader within her company.

The fact is, no matter what leadership level you sit on, difficult conversations are… difficult.

We will all encounter difficult conversations within our lifetimes, whether we are in a leadership role or not. So it is best to be prepared when they ultimately arrive in your life!

Here are four simple ideas, that if implemented successfully, will improve the output of any difficult conversation you have to orchestrate:

Remove Emotion


The number one factor of why difficult conversations turn into a verbal car-crash is… Being emotionally driven.

By definition, a challenging conversation will be emotive for at least one person (probably both people). As the instigator of the conversation, you will have adrenaline coursing through your veins. Your emotions will feel like they have just stepped up a gear, as your body goes into “fight or flight” mode. This is not helpful.

What is helpful is to, in a calm and mindful manner, focus on the facts. Rather than focusing our energy into how we feel. By doing this, the conversation has a good chance of remaining factual and real.

Reality is vital if you want a positive outcome to the discussion!

The single best way to lower your emotional levels before a difficult conversation – Preparation.

Understand the facts and rehearse the conversation. Physically practise saying what you want to say. The more you practise, the better you will get and the less emotional you will feel! Therefore, even if you have adrenaline pumping through your veins at the moment of truth, you will still be able to deliver the facts in a calm manner… because you have rehearsed it perfectly.

Also, it is powerful to rehearse the conversation with a focus on service.

When the conversation priority is a positive outcome for all concerned (not just a positive outcome for you!), you will have to alter your style and become less defensive. This approach has great benefits – it will lower the defences of the person you are talking to, thus lowering their emotional levels and it will enable you to talk in a frank and factual way, without it appearing as an attack.

A good strategy for a difficult conversation!

Understand you don’t know everything

You only know your facts… that is all.

When you understand this, it will allow you to focus on conclusions rather than delivery.

What I mean by this is that it is far better to be focused on a positive outcome, rather than being singularly focused on getting your side of the story heard.

So many people go into difficult conversations, bursting to say their piece. Bursting so much that it gets fired out like a machine gun… a surefire way to ruin the rest of the conversation.

If you enter the conversation with your main priority as a positive action resulting from it… then you will be more likely to listen… you will be more likely to understand… and you will be more receptive to the right course of action.

“If there is any one secret of success, it lies in the ability to get the other person’s point of view and see things from that person’s angle as well as from your own.”

Henry Ford


Make sure your facts are facts

This is the oldest advice in the book of giving feedback, but there is a very good reason for this… because it is true!

The bottom line – Your facts have to have been observed and checked by you, if not you are setting yourself up to fail. The moment you rely on second hand information, the conversation will spiral out of control.

Again this is why preparation is so important. If you don’t do your homework properly, you are asking for trouble.

Give time and space

a_god_of_time_and_space__remake__by_cherryorchid-d6xum80.pngI have seen people utilse all the advice above, but then all that great work is destroyed with this common mistake… a tight time limit on the conversation.

You can make great strides, but if you have to cut the meeting off because of something else you have booked in to do, then you may as well not have bothered starting the discussion.

To rectify this you should plan and prepare for the discussion to go twice as long as you anticipate. If it is difficult for you, then it is difficult for them. Show them respect by giving them the time and space they need. They probably haven’t done all the preparation you have, so give them the opportunity to work through it properly.

If you do this, you automatically get two benefits:

  1. Shows that you are interested in them and a positive outcome, which will reduce their emotional levels.
  2. Allows autonomy – You give the person the time to come up with the right response, through their own judgement rather than emotion – 99.9% of the time they will develop a brilliant solution.

Putting it all together

We will all have to face difficult conversations in our lives… and they are going to be difficult!

You can make them much easier if you plan and prepare

  1. Remove the emotion, rehearse and aim to serve.
  2. You don’t know everything, so focus on outcome rather than saying your bit.
  3. Ensure your facts have been observed by you.
  4. Give time and space to work it through properly.

What to do when you have been let down by someone you trust

I have recently been badly let down…

The person in question was in a situation which was difficult for her, she was highly stressed and appeared to be making herself ill.

So I listened, I supported, I trusted, I guided. I even went above the call of duty and threw myself in the firing line for her.

My action worked – her stressful situation dissipated and, in the moments when I took the heat away, she turned on me – blaming me for it all and informing everyone that would listen, that she was faultless. She quickly distanced myself from her and then she attempted to muscle in on the good work I created for her company!

How would you respond if this was you?

The probability is you will have experienced a similar situation like this in your life. Where someone you trust, fails to reciprocate that trust and lets you down.  When this happens it is understandable that your response would be emotional and negative.

The unfortunate truth is that responding this way rarely helps anyone. Especially you.

The reaction that will serve you best will help you move on and be able to trust again quickly and wholeheartedly. Here is how:


“Forgiveness says you are given another chance to make a new beginning.”

Desmond Tutu

Holding resentment inside only hurts one person – you. The last person who needs to be hurt by you is you, so you have to rid yourself of resentment.

Resentment is like drinking poison and hoping your enemy will die. The poison will do nothing to your enemy, but will kill you!

Forgiveness can seem hard… Why should you forgive someone who has hurt you? The reason you should is because forgiveness isn’t just about the antagonist, it’s about allowing yourself to stop hurting… and you deserve that.

Be your best self

20141223140914-give-gift-your-presenceSometimes when we feel we have been let down it is easy to close ourselves off to the world.

Who is this behaviour serving? Nobody, that’s who.

The past is the past. It cannot be changed, you can only learn from it. The one thing that is an absolute certainty in life is that if you want the future to be brighter, you have to bring your best self to the game.

Be bigger, be better and be bolder… be your best self and you will bring the best out of the present and the future.

Expect the best in others

Just because one person has let you down, it doesn’t mean the world is full of evil, untrustworthy people. 99.9% of people have the desire to be nice, kind and helpful individuals. Don’t close down your opportunities to connect deeply with others, just because one person has broken your trust.

If you expect the best from others, your behaviours will adapt accordingly and you will engage with the world in a positive fashion… and guess what? Engaging positively with those around you will, 99.9% of the time, result in positive outcomes!

Surround yourself with positive people

When-you-surround-yourself-with-positive-loving-peopleIt is said that you are the average of the 5 people you spend the most time with. So who do you want to be and who do you want to be surrounded by?

This is a choice – seek out the people who have aspirations and goals like you. The people you admire. The people you can trust.

Don’t get sucked in by people who are self obsessed, negative or selfish… It will drain you. Instead look up at those people who soar… and choose to fly with them.

Putting it all together

The bottom line is that some people will hurt you – NEVER let that stop you being the wonderful and authentic person you are.

Be the best version of you!


Two Simple Steps That Will Help You Build Strong Relationships… Today.

This is a video I have created, about how to create deep and meaningful relationships with those around you. Being able to connect quickly and authentically is such a powerful life skill and has massive benefits to you and the world around you.

These three strategies have literally changed my life, by vastly improving the relationships I have at work, at home and socially.

Hopefully, this advice can help you:

How Small Talk is Big Talk

Over the last few months, I have been researching a lot of books and literature about the different levels we interact at and the common consensus is we work and communicate on five levels, which are all equally important.

Re-charge – Relaxing and reflecting, this is normally conducted by ourselves and is about mentally refreshing.

Chit-chat – Basic social interactions about trivial matters.

Deep 1-1 conversations – Being fully present, emotionally and intellectually engaged with someone who shares similar values.

Multi-tasking– Focusing on a number of tasks at a given time (you probably spend a lot of time in this zone whilst working!)

Flow – One subject, with deep focus and attention. 

While conducting this research, I realised I have a problem with one of these levels.
My problem was with small talk… Chit-chat… Gossip… Tittle-tattel… those conversations that are conducted socially and are usually about superficial matters.

I personally have found these types of conversations the hardest to give my full self too. I think that is because until discovering their importance I held them in low esteem. I felt this type of interaction held little value or worth and therefore would try to skip the small talk and get onto deeper, more meaningful topics.

What I have learnt since is that chit-chat is vital for building relationships and trust… The idea of discussing in depth subjects with someone you haven’t had even a small connection with previously is a big turn-off for most people.

For me this meant that I rarely had deep and meaningful conversations with many people because I tried to jump right into them, without first connecting on a more surface level. Therefore the impact I had on many people was that I was either a bit intense or just plain weird.


The fact of the matter is, small talk is easy. You won’t go too far wrong if you pay genuine attention, listen well and ask clarifying questions. We can all do it. It’s just that some of us undervalue this level of communication because of the appearance of its lacking depth.

The best analogy I have been told about small talk is to view it like trying on a relationship. Just like you would try on clothes in a store. Small talk is a risk free environment where you can assess each other in a non-threatening or judging way, to see if you have rapport and get along.

If you do, then the deeper more meaningful conversations will follow… If you don’t, both parties can remain at this slightly superficial level with no harm done to anyones feelings.

If you want the big talk, the meaningful talk, then pay attention to the small talk, it is the doorway to deep, authentic connection.

How to deal with really annoying people!

Earlier this week, I spent time with two perfectly pleasant individuals who, on the surface appeared to really dislike each other. No matter what they discussed, it always seemed to finish in a disagreement and sometimes they disagreed before the discussion started!

Upon reviewing this with them both individually, they said that they found the other person really difficult, challenging and stubborn.

This reminded me of the times I have found certain people in my life particularly challenging, rude and sometimes obnoxious. We all have these people in our lives, even now someone has popped into your head while reading this!

What we normally do with these people is either to fight fire with fire, defending our cause to the death and reflecting the rude behaviour they showed. Or we retract inwardly, making our interactions the minimum they have to be.

It may come as a surprise, but I have discovered neither is a good strategy!

A few years ago, I decided this had to change, that I had to change. I did lots of research and I interviewed people who are saintly when interacting with others. Here is what I have learnt and maybe these approaches can help you deal with that really annoying person in your life:

1. Understand what a difficult person is.


In its simplest terms, this will be a person who has a different perception or perspective than you and will communicate that in a way that pokes at your value system.

For example, if a key value you hold is respectfulness and you believe that the way to demonstrate respect is listening to the other person without interruption – then you find that someone who continually interrupts you with disagreements to your perspective, you are highly likely going to find that person difficult to deal with.

So with that in mind, it is important to appreciate the fact that other people can have a different perspective than you AND YOU CAN BOTH BE RIGHT.

2. Ask “What is going on in their world at the moment?”

The overwhelming majority of people will see themselves as ‘the good guys’ and do not deliberately spend their lives trying to be a difficult, obnoxious person! The reality is that there will normally be an external stress or pressure somewhere in that person’s life to cause the bad behaviour. Except this and you can easily stop taking their actions as a personal attack.

One particular example of this has stuck with me. I once opened a door to get into a building and a woman walking the other way barged past me without a word. I was offended by this rude behaviour instantly and sarcastically shouted “Thank you” in her general direction. I later found out that she had just been told that her son had been in a serious car accident and was rushing to the hospital to find out if he was okay. Who was the difficult and obnoxious person?

3. Ask “What does this person need?”

As described above, bad behaviour is rarely a hobby for people, so understanding that the difficult person you are dealing with will need something in that moment is important. Do they need a break from the discussion? Do they need to be listened to? Or maybe they need encouragement?

4. Listen to understand… Don’t listen to defend!


Listening to defend is letting the other person speak, just so you can gather more information to argue your point! This is literally useless and will not improve the relationship one bit!

It is common sense that understanding others point of view is critical in building relationships, rapport, gaining trust and creating a collaborative working relationship. Common sense is sometimes just not common practice. The key factor here is to take accountability to understand them first, don’t expect them to listen to you first.

5. Clearly communicate your own perspective.

Again this sounds obvious, but this is a common mistake.We assume everyone knows what we know and see what we see.

Don’t assume they see ANYTHING the same as you – people are not mind readers, don’t expect them to be.

I remember a time that I had an argument with my then girlfriend about the colour we should paint the bathroom (Yes -really). Anyway just based on the fact that we were stood in different places in the room, we couldn’t agree on the colour. We literally had a fight about this until I stood in the same place and she was, then I realised that the colour I liked looked awful when the light hit it a certain way!

I assumed she could see the same as what I could see… Never assume!

I hope you enjoyed this post and it help’s you in your relationships with those difficult, annoying people in your life! Remember it’s only fair to share, so please share this post!!