Communication Mistakes to Avoid in A Difficult Conversation

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Some time or another everyone faces a time when a difficult conversation is necessary. It’s in those moments that your true leadership is tested.

You may be dealing with an underperforming employee, disagreeing with a spouse, or negotiating with a client. Difficult conversations come in all forms, but they have one thing in common: They’re not easy.

We all enjoy challenging others, helping them find their potential, motivating and inspiring them. But sometimes what we are called to do involves conveying bad news in challenging times—and our role as leaders is to have the courage to do it in a spirit of learning and exploration.

When the conversation is difficult and the stakes are high, the same communication mistakes that can create problems for you at any time become especially important.

Here’s a refresher course on how not to make things even harder:

Don’t assume. Don’t assume that people know what is going on—or that they know anything. As a leader, it’s your job to bring as much clarity as possible, so start at the beginning. People are looking to you to know what is going on and to share it with them concisely, clearly, and with candor. While you don’t want to provide irrelevant details that are likely to distract and confuse people, telling a story that everyone can understand with information they can comprehend will keep your credibility high.

Don’t hide your feelings. When times are tough, emotions are raw. And when you’re feeling overwhelmed, you might attempt to hide your feelings out of fear of looking weak or vulnerable. But showing your emotions (ideally without losing it) lets those around us know there’s strength in vulnerability. A tender heart is as important as a tough mind.

Don’t ignore who you are. Sometimes to save face we act like what is happening around us isn’t what’s happening within us. That approach never serves anyone; it just makes you look and sound disconnected, disoriented and disheartening.

Don’t shut down. When conversations are difficult, bring a mindset of inquiry. Be open to hearing what the other person has to say and observing how they seem to be feeling. A good leader remains open and seeks a greater truth in any situation. This approach puts everyone at ease and helps keep people at their best.

Don’t judge. People are going to have a reaction to your message. Be the kind of leader who listens to the meaning of what people are not saying. Listen to the silence between the words not spoken. Listen to the feeling behind the words that are spoken.

Communicating well is difficult, especially when emotions are running high and no one is at their best.

But the more you can remain the leader who leads from within, the one who is open-minded and open-hearted, the better you will be able to connect and engage with your team even in the worst of times.

Lead From Within: When situations are difficult, conversation is difficult. Trials test who we are and what we will do; they test our warriorship as leaders, drawing us to awaken our empathetic mind and our sympathetic heart. And when we do, we will be the kind of leaders we were meant to be.


N A T I O N A L   B E S T S E L L E R
The Leadership Gap: What Gets Between You and Your Greatness

After decades of coaching powerful executives around the world, Lolly Daskal has observed that leaders rise to their positions relying on a specific set of values and traits. But in time, every executive reaches a point when their performance suffers and failure persists. Very few understand why or how to prevent it.

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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,, 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. Susan Mary Malone

    16. Jun, 2015

    These are great tips, Lolly. I came of age at a time in business when women were instructed to hide their feelings! We were told to be more like men. I can only laugh now, thinking of those times! But I had to learn to actually be authentic with my feelings (and still sometimes have to fight it). It’s great to get that validation from your post!
    Thank You!

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  2. Duncan M.

    16. Jun, 2015

    Difficult conversations usually lead to a partial or complete shut down. It is sometimes easier to assume than to actually find the root of the problem. These are great pieces of advice that guide to the sole purpose to lead from within.

    Reply to this comment
  3. Matthews Otalike

    16. Jun, 2015

    This is another introspective piece from Lolly. Of course communication mistakes compound already tense relationships in the workplace. From experience I thought that a leader that leads from the standpoint of a door mat (humble) can appreciate the emotions of the led (EQ) with empathy. It creates resonance among the led leading to trust building and harmonious working relationship and environment.

    Lolly thanks for this too.


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  4. Garren Fagaragan

    16. Jun, 2015

    Aloha Lolly,

    Another wonderful post, filled with ideas to reflect, contemplate and implement for positive change within.

    Thank you for the refreshing refresher!
    I appreciate it.


    Reply to this comment
  5. arcnubia

    16. Jun, 2015


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  6. Panteli Tritchew

    17. Jun, 2015

    I do believe that God (or the Universe) provides. If we are facing a difficult conversation, it means that that is exactly what we need for our next level of growth. If we understand that “our role as leaders is to have the courage to do it in a spirit of learning and exploration,” that allows us to pass that test and go on to the next one. Hence, growth. And no one said it would be easy. That why they are, after all, called “tests.” 😉 Great reminders, Lolly. Sending warm thoughts from Vancouver!

    Reply to this comment
  7. Sanjay Rakecha

    20. Jun, 2015

    Very useful post

    Reply to this comment
  8. Matthews Otalike

    20. Jun, 2015

    I keep coming back to this post again and again, seeing it as a personal epistle from Lolly. It’s enriching.

    Reply to this comment
  9. Dawold Chishti

    22. Jun, 2015

    Great tools for stressful interactions, however requisite skills may be blended for positive results. Wonderful post once again you have shared. Thanks, Lolly!

    Reply to this comment
  10. Brian Wozniak

    25. Jun, 2015

    Good post. I especially like the “mindset of inquiry”. Just gaining a better understanding can help break down a lot of the tension. Clarity is necessary, not always agreement.

    Reply to this comment
  11. Ray Brown

    27. Jun, 2015

    This post ties in very well with your friendship/leadership observations. Being strong enough to be authentic, yet vulnerable and true to your values is where we’d all like to be. In times when difficult conversations are necessary it’s even more important to hold on to the fundamentals of relationship management.

    Reply to this comment
  12. Daniel

    30. Jun, 2015

    Great post! Thanks!
    A good tip for delivering bad news, which I have found very useful, is to say the bad news statement first, followed by a “but…” and saying something possitive. This will get the message through, but will deminish any hard feelings or emotions.
    E.g. “Steve, I am afraid that we will not be able to renew your contract with us; but I want you to know that I will do my absolute best to connect you with my network so you can find another job easily.”

    This tip is specially useful when you don’t want to hurt the feelings of the receiver, or you would like to keep the relationship in good terms.

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  13. Majed Badra

    04. Jul, 2015

    Great article Lolly. One of the biggest mistakes I see in communication is when people go on the offensive to start out a conversation. The other person will immediately shut down and go on the defensive. This type of conversation will not usually end well and nothing gets accomplished. In crucial conversations where stakes are high, it is important to start out a conversation by sharing your side of the story in a respectful and calm matter, and asking the other party what their thoughts are? What is your desired result from the conversation?


    Majed Badra

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  14. Haider abbas

    02. Aug, 2015

    Best article I have ever seen. And also most helpful and useful in our daily life not only for enterprising. Great

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  15. Peter Zvirinsky

    15. Aug, 2015

    Wonderful hints. I recall such hard situation when solving issues with a client over email. Your five tips work not only in fact to face talk. I found them even more important in indirect communication. There it is harder to see the feelings, so wrong assumption of a reader can lead to big troubles.

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  16. Riaz A. Malik

    11. Oct, 2016

    Fantastic advice through a detailed viewpoint. Will certainly adopt the methodology. So much knowledge from Lolly – I am honored and lucky to have found her. WISH I could be her stundent all my life . I am still! Buck up Lolly.

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  17. Tarun Bhatt

    20. Dec, 2016

    Great article Lolly, especially the Don’t ignore who you are, Don’t shut down, Don’t judge. I.e. be a good listener.

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