Whenever you’re in conflict with someone, there is one factor that can make the difference between damaging your relationship and deepening it. That factor is attitude.
~William James

It’s 4 am. The house is dark, and everyone is asleep; except you. Caught up in a maelstrom of thoughts and emotions you’re having imaginary conversations with work colleagues where you tell them precisely what you think of the poor presentation they sent you in preparation for a client meeting.

Fast forward to 4 pm. You stare frustrated at your laptop screen, fixing said presentation. In turns out that the 4 am imaginary conversation was just that: imaginary. When faced with your work colleagues in the morning, you backed off from having the tough talk, struggling to get any real feedback across and filled with anxiety. You make a cup of coffee and settle in for a long night of fixing other people’s work.
Why do we find it so difficult to have tough conversations at work?

Let’s face it; most of us find having tough conversations, tough. I believe that we often experience anxiety about these situations because of the number of unanswered “what if” questions in our minds. Fixating on a set of vague, potentially adverse outcomes allows our anxiety to increase exponentially, pushing us further away from constructive actions. The first gift we can give ourselves then is to write down all our “what if” questions like “what if the person gets angry”, “what if the person argues with us”, “what if they act against us in spite” or “what if I lose a friendship”. Once written down, you can sort these fears into two simple categories – those likely to happen and those unlikely to occur. Your efforts should be spent on mitigating reasonable fears or accepting them as a possible outcome that you are willing to face.

What is the payoff from having tough conversations?

Having tough conversations, especially in a work context, can have far-reaching benefits. These include opportunities to build better relationships, increase quality and outcomes, help build careers, help develop new skills and most importantly showing others that they are significant and valued.

These benefits are mostly achievable if tough conversations happen with the following guidelines in place:

  • Be specific: Vague criticism about someone’s performance or attitude is not useful as the receiving party cannot exercise their choice to change something. To make tough conversations truly transformative, you have to be prepared to be specific.
  • Statements: “You often make mistakes in communications” vs “When you sent that email with an incorrect quote to our client, it caused unnecessary rework. The client lost trust in us, and our reputation was tarnished.” You will notice that the second statement is straightforward and informs the person of both the behaviour and the consequences thereof. In this way, they know exactly how to adjust their behaviour in future.
  • Be Future-Focused: Helping someone work through ways of changing behaviour or outcomes in the future is where real transformation happens. This requires that you listen to their ideas with an open mind and hold space in the conversation to allow for challenge. I remember an incredibly transformative conversation with a colleague in a corporate setting where, as HRD, I had to address their interpersonal style at work which had resulted in a serious disciplinary process. By being specific, focusing on the impact of their behaviour and holding space for them, they were able to openly discuss their struggles as a parent of a child with autism and how this had negatively impacted their work. Ultimately, it helped them transfer to an area in the business more aligned to their skills where once they felt more in control, the style issues wholly disappeared. I have watched with immense joy how they have transformed their career and now own a successful business of their own.
  • Be Prepared: In the words of UCLA men’s basketball coach John Wooden, failing to prepare is preparing to fail. To get the best out of a tough conversation, you must prepare. Take some time to write down your fears, think about potential outcomes and plan a meaningful discussion. Good preparation is critical in preventing amygdala hijack, an intense, sudden emotional overreaction to situations (Goleman, 1996) that can be highly damaging in challenging conversations.
  • Be Kind: Of all the guidelines mentioned, I believe this one is the most important. When approaching a tough conversation, ask yourself first whether you are doing this out of kindness. If the answer is no, pause and ask yourself if your own negative emotions are standing in the way of a kind conversation and if you can resolve these first before having the conversation. In my experience, it is often the things left unsaid too long that creates such emotional noise that the opportunity for transformation gets lost.

The good news is that we can call learn to have transformative tough conversations. To help you prepare for your next tough talk, download this handy Conversation Preparation Worksheet. I also offer 30-minute virtual power sessions to help you prepare for or debrief in a safe, supporting coaching environment.

Good luck and please share your transformative, challenging conversation stories with us!



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