How Great Leaders Handle Difficult Conversations


Even though communication is the lifeblood of any organization, it’s difficult to find a company that doesn’t have its breakdowns in this area. Part of a leader’s job is to keep these to a minimum and handle effectively.

In reality, most people avoid conflicts and the confrontations required to deal with them not because they lack the will, but because they lack courage to overcome that fear of “what if” and the potential of something unproductive.

No one is immune to workplace tensions- It is inevitable that you will have some challenging conversations with colleagues or customers.

When we need to have a difficult conversation with someone—we always have that gut feeling of resistance. Fear and contemplation drowns that inner voice and we put the conversation off.

Meanwhile the other person continues to provide substandard performance, miss deadlines, engage in interpersonal conflicts and contributes to a toxic culture.

The consequence of not having that uncomfortable conversation is costly.

A  recent study by Accenture revealing that, even in this challenging economic climate, 35 percent of employees leave their jobs voluntarily because of internal politics and conflict.

Judith E Glaser in her recent book about Conversational Intelligence says that, “…confronting another person with difficult conversations brings up potentially volatile emotions, so we move with caution and keep our real feelings close to our chest. In the most extreme cases, when we are faced with situations that stir up highly charged emotional content, most of the tension and drama is actually taking place in our own minds. “


 Here are four ways to reach a constructive outcome, no matter how tough things can get:

 Focus on Building Trust: Every difficult conversation is an opportunity to improve the circle of trust. Assumptions and doubts block the development of trust. The key to trust is understanding the imperfections of every person. To trust is to create a safe space for the other person to be who they are.

As a leader you need to help open the individual’s mind to see solutions to problems, to get “out of the self- imposed limitation” and perceive solutions.

Demonstrate Empathy: A leader seeks first to understand than to be understood. Sincere and selfless way. Showing empathy and understanding, will lead to the development of mutual trust allowing individuals to open up their mind and heart and derive all the possible benefits to help move them towards their a better relationship.

Listen well: Not only to what the person is saying but what he/she is feeling. To create clarity and to let people know you’re genuinely listening, validate what they’re feeling — and ask them to do the same.

In fact, take a few moments to listen to their side of the story first before sharing yours, and always demonstrate you are genuinely interested in hearing their story. Difficult conversations are emotional and you need to get a good appreciation of the underlying issues that drive the emotions.

Co-Create Solutions: Work together on a common solution to the conflict you both facing. This is a really great opportunity to collaborate and open up to new possibilities. With Co-Creating, each person is accountable to pull their weight into a constructive solution that can bring a win- win to both parties.

What about you? How do you handle difficult conversations with your colleagues or other relationships? if you like to watch a great interview about having healthy conversations, check the link below

6 thoughts on “How Great Leaders Handle Difficult Conversations

  1. Sadly the cartoon is more truth than fiction. I’ve never been able to figure out the logic behind shading the truth and not having an open and honest conversation, or several. The outcome is no less devastating. Open dialog puts situations in the light where they can be dealt with. The next few months could prove uncomfortable, but no less than the declaration above – I have to cut her loose. The sever is immediate, but the suffering still started long ago, and now will contaminate the healing process as well.

    1. TKTM — The way I see it is that people don’t know how to talk. Even leaders. If I have a problem with someone’s performance, I should not begin with a You-Statement. It is bad form, in my opinion, to begin by saying “Your design is sloppy and you come in late to work.” Instead of the You-statements, I find it more helpful to use observation language coupled with I-statements. Managers & leaders need to learn this because it keeps the evaluation from being an attack. So what does “observation langauge and I-statements” look like? Glad you asked. It would be a statement like this. “The design expectations are X and what I see does not meet the expectations. What can you do to have the design meet expectations?” Or “What is needed to meet the design expectations?” <– language like this accomodates that the answer might be a problem in the system. What is needed is direct coaching in the area of communication and I-statements. I don't think there is any way an evaluation can go wrong if both parties stick to the candid way of communicating observation language and I-statements.

      1. I love your approach. What I find to be essential is also asking how the person feels about their work. It gives them the opportunity to assess their own work and both parties may have a better understanding of why the results were sub-standard. It could be as simple as a disconnect – the employee didn’t understand the specs. It could be a deficit – the employee doesn’t have the knowledge or skill at this point to meet expectation. It could be a defect – the tools / training were wrong. Or it could be attitude (employee’s or manager’s)- which is destined to be lose/lose for everyone unless adjustments are made.

  2. Love the toon above and the notion that a difficult conversation is the opportunity for trust building. Sounds like it’s actually a blessed golden opportunity given that conflicts will assuredly arise as you spoke.

    WIth respect to focusing on building trust, what might be and example of how to do that?

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