How to Have Those Tough Conversations.


Woman at work overwhelmed with head in hands

Wouldn’t it be great if we never had to have tough conversations. After all, most of us don’t like conversations that can feel awkward, let alone potentially confronting. It intimidates our psyche and it can challenge our equilibrium.


Let’s be honest. Most of us want to enjoy life, getting along with everyone, and never having to deal with conversations that have the potential to be uncomfortable.


When we know we have to have a challenging discussion with our boss, co-worker, partner, friend or child (especially an adolescent one), our anxiety levels have the potential to increase considerably.


Conversations are how we build relationships, and sooner or later, we will have to have one that takes us out of our comfort zone. So, ultimately, it comes down to how we deal with them.


The hardest part of those tough conversations can be simply getting up the courage to begin.


So why do we need courage? Often we are fearful of the impact we may have on the relationship. Will the other person to become upset? Think badly of us? Use their (perceived) power against us?


It’s no wonder that our perceptions of what the outcome could be might in turn bring on concern and panic that we’ll get it wrong. But we can’t bury our heads in the sand and believe that it will all just go away. Instead, we need to be open minded about the outcome.


So, where do you start?


Get yourself into the right mindset.


Work through any triggers that have been activated that don’t belong to this situation, and identify feelings that may hold you back from starting the conversation.


Imagine the other person’s position in this conversation. How will it appear to them? Ask yourself:

  • What do I want to achieve as a result of having the conversation?

  • What outcome can I live with.

  • How may I have inadvertently contributed to the problem?

  • Is the other person even aware that there is a problem?

Being able to answer these questions will help you work on the most productive outcome for all concerned.


Above all, you need to go into the conversation with a positive, calm and collaborative attitude.


Be prepared to listen.

Active listening is a crucial component to achieving a positive and equitable outcome for all.


“Seek first to understand, before being understood.” - Franklyn Covey

Someone who feels listened to is usually more willing to hear what we have to say. So we need to frame things in a way that will open the doors to constructive dialogue.

Be prepared also to compromise. You won’t discover this until you have listened to the other party and understood their views.


Throughout your preparations, never make any assumptions about how the other person or persons will react or what their attitude will be.


For example, if the conversation is regarding your feelings of being disrespected, intimidation or being ignored, don’t assume this is because the other person has negative feelings toward you. Often, the other person isn’t even aware their actions have had such an impact.


It would help if you discovered the underlying cause of the issue. You may think you know. However, problems can often have deeper origins, and you need to work these out beforehand.

If you have prepared well, you will be able to conduct yourself with confidence and ease.


The Conversation.

Now you are ready.


Tip: Where possible, hold the tough conversation in a timely manner and in a neutral space.


Don’t spring the conversation on the other person. Where possible give them time to prepare. Tell the other person you would like to understand their perspective of the situation and to be able to share your own perspective. Asking questions and acknowledging their responses shows them that you are listening.


You want to be direct and upfront about the matter, while keep the conversation meaningful and non-accusatory. No-one likes to feel backed into a corner.


Approaching the conversation in a confident and respectful manner with the intention of ‘mutual problem-solving’ rather than ‘being right’, also enables you to gain the other person’s trust and have an open dialogue with a mutually acceptable outcome.


Ensure that each party has felt heard, including yourself. If you need to apologise, then do so. And by doing so, you demonstrate your honesty and also humility.


Wrapping Up.

Ensure that all parties have had the opportunity to share their thoughts and feelings.


Agree a way forward and how you will ensure your relationship stays intact and built on mutual respect.


Even if you can’t reach a mutual agreement, make sure you leave with the same calmness you came in with. Don’t burn bridges; that is a total waste of energy and just builds a wall between you.


You cannot control how those you’re speaking to will react. However, by being prepared, you have more chance of hearing and being heard, being understood and reaching a satisfactory conclusion than you would if you just waded into a tough conversation without any forethought or planning.

And if you want some support to help you get there, fill in your details on the CONTACT page and let’s talk.