How to handle hard conversations with confidence

Words by Helen Snape

Ever been told ‘Be more assertive!’ Or maybe you have been sent on an assertive training course and it didn’t really help. You would rather jump into a pool of ice than engage in any conflict at work. You are not alone.

In this article I want to share with you some common myths that are held about how to feel confident having hard conversations at work. And then share with you what actually works, the three keys that go deeper than suggestions of what you might say or how to say it.

The Myths

Ignore how you feel -

How many times have you told yourself to just ignore how you are feeling about the situation, the other person, the conversation, and instead keep your focus on the task at hand and just fake feeling confident? Maybe you wear your power outfit and the heels that mean business.

Or maybe other people have said to you ‘Man up!’ or ‘Don’t be so emotional’ and so you ignored or minimised how you felt about what was happening.

The problem with this approach is that it cuts us off from both an important source of our truth and from our power: our feelings.

Not only does it cut us off from the information we need from our feelings, but other people can also tell when there is a discrepancy between what you feel and what you say. Maybe not consciously, but they can often tell that something is off. And then they won’t want to trust you.

It’s all about assertiveness –

Assertiveness training certainly has its place. It can be helpful in identifying different styles of communication and offering ideas and options for handling different scenarios, from being asked to stay late to handling criticism. It really is what some people need.

However, for some people, people like me, I liken it to a sticking plaster for an infected wound. It might make your work situation feel more comfortable for a while, but it doesn’t address the underlying issue.

Focus on the story -

Human beings love a good story. And we tell them all the time. About other people and about ourselves.

Phillip is mad with Catherine because she didn’t consult him about seating arrangements in a minor office re-organisation. He says it’s a matter of principle and that it demonstrates Catherine’s incompetence.

Catherine accuses Phillip of being over-sensitive and says she was just busy and got on with the re-organisation to get it off her plate.

When people are caught up in their own and others stories, they don’t have room to see beyond those stories and they are too busy defending their own position. So we need to get underneath the stories to find truth and connection.

The Three Keys to Confidence for Hard Conversations

Mind-Body Connection –

In order for you to accurately represent yourself, you need to know how you feel. In order to know how you really feel, you need to slow down, drop your attention below the chin and then ask ‘How am I feeling right now?’. And wait for the answer to come to you. Then, whether the other person likes what you are saying or not, you are communicating what is true for you.

In addition, your feelings are fuel for what you need to say or do. For example, if you feel angry about what someone has said, that anger will push you forward. This doesn’t mean that you should be led around by your feelings though.

I like to use the analogy of a car. Whilst you don’t want your emotions to be in the driving seat, you don’t want to lock them in the boot either. Your emotions are a valuable passenger who will give you helpful directions on what you need to say or do.

Self-Trust -

There are two distinct layers to confidence – our belief in our own abilities and the trust we have in ourselves. The top layer is our belief in our own abilities, which grow as we assess what we need to learn, we experiment, we seek opportunities to try out what we are learning and we commit to keep learning. It is like building a house, one brick at a time.

But if we lack confidence in ourselves, then when we exercise an ability and make a mistake or we receive criticism, even that confidence in our ability is knocked because we lack a firm foundation of trust in self.

If we don’t trust ourselves, we don’t have that firm foundation to build on. When we have built that foundation, we can make a mistake or hear criticism and our confidence remains intact.

You can start building that self-trust through self-discovery. Trust grows the more we know someone. You need to know yourself! And here I am talking about your true self, not the roles you might play in life, such as parent, employee, friend, child, sibling. Learn what you truly love and what you hate. Make a list of what you are good at and what is important to you.

You also need to stop listening to everyone else – your opinion of yourself is what matters most.

Turn to yourself as the best source of knowledge about yourself – no one knows you like you do.

Effective Communication -

Instead of getting caught up in the stories that we tell each other, find out what the unmet needs are. Both your own unmet needs and the other person’s.

In the example above, Phillip actually felt disrespected by Catherine not consulting him about the office re-organisation and what he needed was respect in that relationship.

Catherine was actually feeling overwhelmed with work and unappreciated by her colleagues, including Phillip. What she needed was appreciation for her organisational skills.

When you are clear on what your needs are, you can then communicate them clearly and simply. And the same goes with what you want. You can be clear on what is a ‘must have’, what is a strong preference, and what is a ‘cherry on the top’ for you.

This includes having boundaries about potentially difficult conversations. For example, you might ask for a time out if emotions in either party get too intense – remembering to be clear when you will return to the conversation.

This is the deep work to building confidence in having hard conversations. You can learn to stay connected to yourself and your feelings, build a firm foundation of self-trust and how to effectively communicate around yours and others needs and wants. Then you will find your confidence will naturally grow and even those hard conversations won’t seem so hard after all.


Helen Snape is a trauma-informed Healthy Relationships Coach who helps ‘good girls’ grow their guilt-free ‘No’ and find fulfilling relationships at home, at work and beyond, by building boundaries, confidence and effective communication skills.. Helen is also author of
‘Building Healthy Boundaries – an over-giver’s guide on when to say Yes and how to say No in Relationships’.