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Executive Insider

Difficult Conversations: We can work it out!

Shantha Mohan Ph.D.

“Try to see it my way Only time will tell if I am right or I am wrong.” – Lennon & McCartney

Wikipedia says when Paul McCartney wrote the lyrics for We Can Work It Out, he was probably thinking about his relationship with Jane Asher, his girlfriend at the time. John, who contributed to the middle eight, said in an interview, “In We Can Work It Out, Paul did the first half, I did the middle eight. But you’ve got Paul writing, ‘We can work it out / We can work it out’ – real optimistic, y’know, and me, impatient: ‘Life is very short, and there’s no time / For fussing and fighting, my friend.’”

Both Paul and John were right. In any difficult conversation, you need the optimism that it can be worked out. It is also true that we must feel the urgency in getting through such a conversation and go on to a resolution for the situation that created the need for it.

We encounter many such conversations in the workplace. How do we have them without damaging the relationship that exists between us?

Conversations We Dread

There are many workplace scenarios in which the need for difficult conversations arises.

Any conversation about compensation can be difficult, considering the topic of money makes us uncomfortable. Such discussions happen when recruiting for an open position and during promotions. Sometimes it occurs when a team member is unhappy with theirs and gives you an ultimatum that, without a raise, they will quit. 

Delivering periodic performance reviews can be challenging when an employee’s performance does not meet expectations. Even when the performance is good, when you suggest areas for improvement, the message may not be received well.  

In any teamwork, there will be conflicts and differences of opinion. As a leader, you must deal with conflicts to restore harmony so team members can work effectively.

Sometimes, a leader has to deal with a personal situation. A team member may be dealing with the death of a loved one or is going through a divorce. 

As we have seen recently, economic downturns force adjusting the workforce. Layoffs necessitate conversations that are extremely difficult and charged with emotions. 

Strategies for Working it Out

Here are three practical strategies for a leader to follow when dealing with difficult conversations.

  1. Prepare for the Conversation
    Create a plan for what you say, how you say it, and what you want to achieve with the conversation. Instead of having it all in your head, write it down, read it multiple times, and imagine yourself saying them. Come up with scenarios of what the responses might be, and practice how the conversation might evolve.Think about the environment where you want to have the conversation. For example, having it during a walk together might be better than sitting at a desk. The goal would be to reduce any interruption. In today’s remote working environment, we see many difficult conversations, such as layoffs happening over emails. If you have remote team members, you must have these conversations over video.

    Find the right time to have the conversation. If you have critical meetings coming right after the conversation, it might pressure you to close the discussion without a mutually agreed outcome prematurely.

    The strategies for preparation depend on the type of conversation. For example, in the case of a performance review, the preparation is not just before the meeting but starts at the beginning of the performance period. The manager or reviewer must have set clear expectations for the performance, knowledge of specific instances (more than one) when they were not met, how they can be remedied, training schedules to do so, etc.

    In the case of an exchange on compensation, you have to be aware of the market landscape, the value of the individual, the ability to offer a perk instead of an increased salary, budget constraints, limits to what can be provided reasonably without jeopardizing the entire team’s compensation structure. Similar preparation is required when you are on the other side of the conversation.

  2. Listen and Empathize
    In any conversation, listening to the other person is essential. More so in difficult conversations. Use active listening techniques such as repeating what you hear and confirming what is being said. Be attentive with your body language, such as nodding and saying you understand. Be sure to pose clarifying questions when you are not sure of the speaker’s intentions about statements they make.“Empathy is like a universal solvent. Any problem immersed in empathy becomes soluble.” – Simon Baron-Cohen

    When you respond to the person, do it from a position of empathy and respect. In your preparation, you would have gone through possible scenarios, and your responses should be such that the other person’s self-esteem is maintained and you phrase your answer appropriately.

    In the Medium article, “31 Empathetic Statements for When You Don’t Know What to Say,” Laura Click, Brand Strategist and Founder of Blue Kite provides examples of responses you can model yours after. These examples include acknowledging the other person’s pain, sharing how you feel, showing gratitude to be in the conversation, showing interest, and providing encouragement and support. She says, and I agree, that there is no script for showing empathy.

    You can use the examples in the article as a guide. Note that the statements have to come from your heart. Merely uttering the words without genuinely feeling them will harm your authenticity and relationship.

    Being calm and collected during the conversation will facilitate the exchange better than if you are emotional and agitated.

    In any difficult conversation, think about the situation as a challenge that must be addressed, and focus on it instead of the person involved.

  3. Communicate Clearly
    Difficult conversations are better in person and, if that is not possible, on video.Planning for the conversation can mold your thoughts into clear and concise communication, and delivering your thoughts well follows. However, no matter how much you prepare, you may not be able to anticipate all the twists and turns the conversation might take. Anticipate the unknown.

In Toastmasters, we have a section devoted to impromptu speaking called The Table Topics in every meeting. The person leading this section poses questions, and you have to come up with an answer on the spot. 

It helps us prepare for those instances when we must communicate without preparation. Even if you are not a Toastmaster, there is a framework for impromptu communication called PREPPoint (state it), Reason (explain it), Show Examples, and conclude the Point)—that can help you with your impromptu speaking. It can help you structure your thoughts and deliver your main point in a clear message.

For example, let’s say you are a manager with the dreaded task of informing someone in your team that they are being let go in a layoff.  

Point: Start with the fact that it is a layoff and does not reflect the individual’s abilities. Be sure to emphasize that it is a difficult situation. 


  1. State why the layoff is happening.
  2. Be transparent.
  3. Explain the market conditions, business climate, and the organization’s highly uncertain future outlook, which has necessitated the budget cuts leading to the layoff.

Example: Share any information that is not confidential such as declining revenues.

Point: Conclude by stating the central message while giving the individual time to absorb the news, offering support services, including career counseling to find a new job, details of severance pay, health insurance continuation, and your gratitude for the individual’s service and contributions. 

Consider Professional Help/Mediation

Some conversations may be too complex or challenging to deal with. They may benefit from third-party involvement. Consider getting professional help in such situations. There are mediators available to facilitate the discussions. They can help keep the topic focused on the problem, provide an objective viewpoint, and sometimes even offer information and advice that can remove roadblocks to resolving the conflict. 

It is important to note that you should do your due diligence to ensure the mediators are qualified and have a high reputation for fairness. More importantly, everyone involved agrees to use such a third party.


Remember the mantra, “We can Work It Out.” While the strategies outlined here can help, conversations have many nuances, and no cookie-cutter method exists to deal with all of them. Approach them carefully and prepare for them diligently. Your goal should be to come out of the discussion with a mutual agreement or, in some cases, an agreement to disagree, maintaining mutual respect. End the conversation with gratitude for the willingness of the participant to have the exchange and find a resolution. It will set the tone for the following discussions and sustain the relationship.

Written by Shantha Mohan Ph.D.

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CEOWORLD magazine - Latest - Executive Insider - Difficult Conversations: We can work it out!
Shantha Mohan Ph.D.
Shantha Mohan Ph.D. is an Executive In Residence at the Integrated Innovation Institute, Carnegie Mellon University. Before that, she was a global software engineering leader and entrepreneur, co-founding Retail Solutions Inc., a retail analytics company. Shantha also has over 20 years of experience focused on mission-critical systems to support semiconductor and other high-value-added manufacturing. She is the author of Roots and Wings - Inspiring stories of Indian Women in Engineering and is a co-author of Demystifying AI for The Enterprise - A Playbook for Business Value and Digital Transformation. Her book, Leadership Lessons with The Beatles, was published by Taylor & Francis in May 2022.

Shantha Mohan Ph.D. is an opinion columnist for the CEOWORLD magazine. Connect with her through LinkedIn. For more information, visit the author’s website.