12 Mistakes to Avoid in Difficult Conversations

Sometimes a difficult conversation needs to happen. But even when the signs are all there, we may avoid them because we’re fearful of the outcome. Meanwhile, something remains askew because of our reluctance to address it.

With preparation and practice, however, you can be more confident in addressing a difficult issue. To help you get started, here are 10 mistakes to avoid:

Shying away from disagreement. Many people are conflict averse. But what if you view disagreement not as conflict but as an opportunity to explore a different perspective? Lean into those conversations and try to understand the other side by exploring and questioning. Then look for the common ground where a solution can grow.

Letting your emotions rule your behavior. If a difficult conversation needs to happen, leave any anger, frustration or irritation you may be feeling out of the dialogue. If necessary, find a way to express and release your feelings ahead of time—but make sure you can calm yourself down before the conversation occurs.

Pushing your views onto others. The last thing you want to do is force your agenda, thoughts and point of view on others, because that will only create something to push back against. Shift your focus to understanding the conflict, and you will find the other person will likely be much more open to your perspective.

Not saying what you mean to say. If you’re inconsistent in the things you voice and do, trust will be eroded and difficult conversations will become even more difficult. If you want dialogues instead of monologues, make sure you’re a leader that people can count on.

Taking others’ behavior personally. If you take things personally andcannot separate the person from the behavior, you’ll have a hard time understanding and addressing their priorities. Remember, at the core it’s about them, not you.

Falling into a combative dialogue. Don’t let conversations turn into a zero-sum game with a winner and a loser. Combativeness will defeat any attempt to find middle ground; instead it will keep you both stuck where you were at the start.

Getting caught up in the tone rather than the content. Some people are disrespectful in their delivery of a message, and often they are unaware of the negative impact of their tone. If that happens, make it a point to focus on the content of the message instead of the tone.

Speaking aggressively. An aggressive stance makes a difficult conversation even harder, putting off the other person or even shutting them down altogether. Learn to keep your tone neutral and to simply state what you want. With practice, you can learn to focus on the outcome.

Making assumptions about the situation. We all make assumptions. In a difficult conversation, an optimist will assume that any disagreement is just a misunderstanding between two well-intentioned people. A pessimist, on the other hand, may feel it’s an attack. Be aware of your own biases and limits going in.

Losing sight of the objective. The key in any tough talk is to always keep sight of the objective. Doing so will help keep the conversation on track. When you stick to your goals, you can push through any conversation without getting lost.

Catching people off guard. Never catch people off guard—it makes them uncomfortable. When disagreements flare, make it a point to connect. You’ll be more likely to navigate to a productive outcome and emerge with your relationship intact.

Avoiding feedback. If people want to share with you what they are feeling and thinking, listen. Tuning out necessary feedback can make it harder to connect and communicate, making the conversation even more difficult.

Most people try to avoid difficult conversations because they worry about damaging a relationship. But often these conversations make relationships stronger, because the best relationships are those in which you can share all your views, even the hard ones.

Lead from within: Difficult conversations requires skill, but avoiding them is costly.


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Lolly Daskal is one of the most sought-after executive leadership coaches in the world. Her extensive cross-cultural expertise spans 14 countries, six languages and hundreds of companies. As founder and CEO of Lead From Within, her proprietary leadership program is engineered to be a catalyst for leaders who want to enhance performance and make a meaningful difference in their companies, their lives, and the world.

Of Lolly’s many awards and accolades, Lolly was designated a Top-50 Leadership and Management Expert by Inc. magazine. Huffington Post honored Lolly with the title of The Most Inspiring Woman in the World. Her writing has appeared in HBR, Inc.com, Fast Company (Ask The Expert), Huffington Post, and Psychology Today, and others. Her newest book, The Leadership Gap: What Gets Between You and Your Greatness has become a national bestseller.

  1. Danny Dukes

    09. Oct, 2019

    Disagreements prompt necessary conversations. Ignoring this won’t make for a palatable solution.

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