The 3 Mistakes You’re Making with Difficult Conversations

Difficult conversations are the ones we have when there is something at stake.

It could be asking for a raise, firing an employee or something as simple as asking a co-worker not to talk over you. Difficult conversations are difficult because
you risk losing something, whether mentally, emotionally, or financially. And the most challenging part? There’s no avoiding them.

The more senior you get, the greater the demands of your role and the greater the chance of having more difficult conversations. Although there’s no way to hide from these conversations, there are ways to help you navigate your way through them.

In this blog post, I will be sharing the top 3 most common mistakes I see people make as they encounter difficult conversations and how to improve them.

Mistake 1 : All or Nothing

Difficult conversations activate the fight or flight response. This shift impairs our creativity because we are not thinking in cooperative terms – we are thinking in safety or scarcity terms. This is a very natural response. However, it doesn’t have to be this all-or-nothing mentality. There are other outcomes to be factored in, and the trick is to pause and ask yourself…

  • What is the middle ground between the best and worst-case scenario? I usually remind my executive coaching clients that possibilities open up with we leave catastrophic thinking behind. It’s about leaving the scarcity mindset and activating the creative mindset. When the stakes are higher, making this switch can be more challenging. But, without exploring the middle ground outcomes, your conversation can degenerate quickly, and it may become a show of strength rather than a means to an end.
  • Is there anything I can add to the mix that the other party will value and this need not be related to the current situation but perhaps a different context that is equally valid or valuable for the other party ?
  • Know your limits – In business school, we have a concept called BATNA, Better Than No Alternative. It’s a good way of understanding the bare minimum viable outcome for you, one that won’t leave you bleeding. Then you have an anchor from which you can work and realize that many options exist between all or nothing.

Mistake 2: Personalizing It

In a difficult conversation, it’s easy to assume that you’re winning or you’re losing. While it’s true that the outcome has a lot to do with you and how you conduct yourself, the truth is that, to some extent, it has nothing to do with you. The other person could be…

  • Afraid to admit their fears
  • Playing out other options in their head that they want to share with you
  • Having a bad day and now you’re the target of their emotions

Difficult conversations are complicated, and personalizing them only makes them more difficult. The Universe does not revolve around you. Perfectionists especially, tend to make this mistake because they take responsibility for the positive outcome of a conversation and can end up blaming themselves excessively if things go wrong.. So, let me repeat, it takes two to tango.

You can only take ownership of how you show up. The response is not in your control. Sometimes despite your best efforts, you will not win. The opposite is also true. Sometimes, without trying hard, the conversation’s outcome is amazing. Learn to create boundaries surrounding what is under your control: your emotions, voice, and needs. Not their response.

Mistake 3: Losing Sight of The Big Picture

It’s easy to get caught up on the here and now when having a difficult conversation. We tend to start obsessing over the choice of words of the other person or the style in which they have delivered the message. It’s easy to do this because we want the difficult conversation to end quickly. However, always pay attention to what is not being said.

  • What is the bigger picture? Think of 5 weeks, 5 months and 5 years from now and how much does this matter in the larger scheme of things ?
  • Are there ways of getting the same outcome through a different means without making this conversation be the end all and be all of your desires. This type of tunnel vision will only increase the scarcity mindset. Sometimes there is more than one way of getting exactly what you want. A client of mine was very keen on a promotion but the relationship with the supervisor was always getting in the way. He found a different project in the company which was high profile and challenging. He raised his hand for it and shone publicly in front of so many people that there was no choice for the company but to give him that promotion. Everything need not be a direct confrontation.
  • What motivates the person to accept or reject the opinion you’re offering? One thing that can help focus on the big picture, is asking yourself am I thinking about the outcome satisfaction of the other person as much as myself ? This will shift the energy of the conversation and how you show up.. Humanize the other person the way you would like to be humanized. Find out a little more about who they are and where they come from and their current circumstances. Sometimes finding out about people and their journey allows us to see them beyond just adversaries for an outcome. Chances are they are just as worried about this as you or maybe they have a blind spot which requires some compassion rather than seeing them as a nemesis out to get you (unless you have tangible proof that this is the case !)

Walk a mile in their shoes and think of how they may be interpreting your ask or your feedback.

Marcia Reynolds, the author of The Discomfort Zone, suggests that you listen to the other person not just with your head but also with your heart and gut. Be truly present to the experience of the other without being overtaken by it. There is such a thing as over empathy or over-identification in a difficult conversation. It’s all about balancing your needs with theirs to find a deeper respect for where they come from and the big picture.

Difficult Conversations In Real Life

One of my clients was worried about having a difficult conversation with his boss because he felt if he went to her with the problem, she would see him as less capable, and by giving her the bad news, he would be letting her down. He was taking ‘over responsibility’ on all fronts – the resources, the process, the outcomes.

By applying the no personalization rule, he recognized that he did not create the problem at hand. Consequently, it could not be solved by him alone because it was an issue of a lack of resources that the organization itself faced. It was also important to note the bigger picture. Had the bad news gone unreported, the boss would ultimately blame him and may have even accused him of hiding the truth.

He was mindful not to see the conversation as having an all-or-nothing outcome going into the conversation. To help him do this, he created timelines for how long it would be before the situation went from bad to worse, so long as his boss did not step up to support the team.

He also suggested stopping gap arrangements until she could come up with the relevant resources. This alone allowed him to keep his identity as a proactive subordinate and her identity as the boss who had greater power to influence resources. In the end, he was able to make light of a difficult conversation so that there was a positive outcome for both parties involved.

As you can imagine, these 3 tips can be used in virtually any situation, as shown by my client. Understanding how to handle difficult conversations is a skill that will carry you throughout your career. And, as mentioned, those difficult conversations aren’t going anywhere, so it’s best to learn how you can get the most from them.

Parting Thoughts

One of the most essential pieces of advice that I can give surrounding difficult conversations is to recognize that avoiding them will not make the issues at hand go away. Dealing with a problem head-on means experiencing discomfort once as opposed to experiencing it at a deeper level and potentially at a large scale had it been avoided in the first place.

You know what common mistakes people make during difficult conversations, and now, you have the tools to overcome them. Remember, lose the all-or-nothing mentality, don’t personalize it, and see the bigger picture. Break down the issues of the conversation into rational and emotional, and devise a plan to tackle them.

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