Melissa Olsen
5 min readAug 23, 2020
Photo by Mimi Thian on Unsplash

Hard conversations are like invasive doctor appointments — we avoid them like the plague. According to a survey by CNBC, 7 out of 10 Americans avoid having difficult conversations at work, with the statistic even worse in smaller organisations like startups. With blurred role clarity and a lack of HR function, people feel they can’t have hard conversations safely, so they tend to not have them at all.

The result is festering issues that never get addressed or resolved and the enormous cost to productivity and stability that this causes. Apply that to conversations in personal lives involving relationships, and it’s easy to see how conflict and dispute build to irreparable levels.

In the past week I have:

  • had a conversation over a cup of tea with a friend who told me she is terminally ill,
  • comforted a friend who’s mother has recently passed away,
  • had on-going conversations with my parents about their end of life wishes,
  • coached a work colleague (in my paid job) on a performance issue,
  • had a difficult conversation (in my side gig startup) with a business partner who is struggling to understand the value proposition of the product we are selling, and
  • had a conversation with my teenage daughter about dealing with sexual predators.

Not one of the above conversations was easy, they were all extremely hard. I found myself digging very deep in my kit bag of communication skills, floundering at times to grasp at whatever I could come up with to make the words fit the situation.

Talking about death, in particular, can be exceptionally confronting but at the end of the day, it is merely a conversation between two people — an imparting and receiving of not only words but emotions, gestures and a meeting of minds that converge to help us understand and be understood.

The Cambridge English Dictionary defines a conversation as “an informal, usually private, talk in which two or more people exchange thoughts, feelings, or ideas, or in which news or information is given or discussed”.

The hard conversations I have had this past week were not conversations I relished having, but they were all presented to me and became necessary nonetheless. I found that if I framed them in my head as ‘just conversations’, it was easier and less intimidating going into the conversations. I didn’t allow myself to get caught up in the preparation and the content. I simply talked, and more importantly listened, from a place of truth, authenticity and vulnerability.

I discovered there were no right or wrong things to say. Whatever you say is your truth, coming from your version of reality and according to your moral compass. There is also the possibility that in some conversations, it is better to talk less and listen more. The urge to fill the breaks in conversations with unnecessary words allows greater room for awkwardness and error. Less is more in hard conversations.

So much of what we pre-empt in our head about having hard conversations assumes what is going to be said to us. We obsess about this and over-play the conversation in our head before it even happens! The truth is, we have no control over or even know what other people will say to us in hard conversations until we have them. How many times do we convince ourselves that there is no point in having a hard conversation with someone because we are convinced of what they are going to say!

So stop putting it off and start thinking about the hard conversations you need to have whether it be in business or your personal life. I hope my top 10 tips below will help you in paving the way for making the conversations less hard than they need to be. Good luck and be brave!

Tip 1: Simply a conversation

Remember, they are just conversations. Don’t avoid them because they are hard.

Tip 2: Desired outcome

Ask yourself what you want out of the conversation? What is the desired outcome and be clear about that outcome in your mind, especially when negotiating the sale of something or if you are negotiating a pay rise.

Tip 3: Openness and honesty

Speak openly and honestly. Tell people how you feel. Yes, the F word, FEEL, even in business conversations, there is still room for feelings! Don’t shy away from wearing your heart on your chest.

Tip 4: Lean in

Lean into the discomfort of the conversation. Resist the urge to shut down. It will pass — just say what you need to say. Sometimes just starting the conversation will be all it takes and the rest will follow.

Tip 5: Don’t assume

Don’t assume to know what the other person is thinking. Ask them what they are thinking? Ask as many questions as you need to establish the other person’s position and be prepared that the position may be vastly different from yours. Nine times out of ten, the answer will be a surprise, and you will come away thinking thank goodness I asked what the other person’s view or position was as I assumed they were thinking something completely different.

Tip 6: Body language

Be mindful of your body language. Crossing your arms and screwing up your face won’t pave the way for a smooth conversation!

Tip 7: Tone and manner

Be aware of tone and manner. Soften your speech and be careful not to use abrasive language.

Tip 8: Feelings

The good old chestnut of “when you do this, I feel _____” is always a good tool to use. It separates the behaviour from the person and removes blame.

Tip 9: Rules of engagement

If things get heated or aggressive, establish some rules of engagement. Be prepared to stop the conversation if certain rules are broken, eg. swearing or intimidation. Agree to revisit the conversation if there is a breach of rules and politely say you will not continue until things are back on track.

Tip 10: Offline only

Keep hard conversations offline. As best as you can, do not have online conversations, especially about difficult matters. Meet face to face or pick up the phone and have the conversation. So much nuance and critical parts of conversations are just not present in online exchanges.

This presents unique challenges in the times we are currently living in where sometimes face to face conversations are just not possible. If you must have a hard conversation virtually, Art Markman, PhD, the Annabel Irion Worsham Centennial Professor of Psychology and Marketing at the University of Texas has written a great article on ways to handle difficult conversations virtually.

Conclusion:

Hard conversations are just that — HARD. No-one likes to have them and so we end up avoiding them. We are all human, flawed in all our glory. Very few humans enjoy confrontation and discomfort.

Have the hard conversation anyway. It will enrich your relationships and open up a world of possibility. And trust me when I say you will feel a true unburdening and lightness once it is over.

Melissa Olsen

A tech entrepreneur of an emotion analytics platform; a real job in sales; a parent; a wife; a daughter; a sister and friend.