The HR Side Of Management: Having Difficult Conversations In The Workplace

By EverwiseJune 22, 2017

As you rise from junior staff to senior leader, you will undoubtedly come across situations where you disagree with your superiors.

For many, the knee jerk reaction to this kind of scenario is to shy away from confrontation. However, Jean-Francois Manzoni, professor of human resources and organizational development at INSEAD, advises that the key to dealing with these situations is to learn how to handle them in a way that produces “a better outcome: less pain for you, and less pain for the person you’re talking to.” The best teams thrive on productive disagreement.

We’ve broken down the essentials to approaching these conversations in order to achieve the productive outcome that you seek while also keeping your relationships intact:

Build trust

As Louis Pasteur famously said, “Fortune favors the prepared.” Communication can’t begin with confrontation. As the Harvard Business Review points out, effective communicators don’t wait for the need to disagree. They initiate numerous other separate conversations when the stakes are low and emotions are calm to agree with their bosses about how to manage those moments when they disagree. This kind of unwritten contract becomes a powerful reference point when emotions are running high. After all, a boss is much less likely to take offense at disagreement if he or she has invited it in the first place.

Focus on intent before content

Intention can make all the difference when it comes to difficult conversations. Set a constructive intention, keeping it positive and respectful. You’re not saying, “no.” You are offering up an alternate solution. One way you can do this is to ask for – and earn – permission to disagree.

When people get defensive, it’s typically because they believe your dissent is a threat to their goals. You can be much more candid about your opinions if you honor your boss’ position and frame those opinions in the context of a mutually beneficial purpose that you know your boss cares about. If you fail to lead with intent, you risk a misreading of signals and a negative response from your boss.

Remember: it’s not necessarily what you say, but how you say it. So keep your eyes on the goal and your intention front and center.

The keyword is: Tact

Tact, as Benjamin Franklin put it, is about “remembering not only to say the right thing in the right place, but far more difficult still, to leave unsaid the wrong thing at the tempting moment.”

When you confront your boss, the way you express your thoughts will pave the way for his/her response. You must carry yourself confidently: apologizing too much will detract from your boss taking you seriously. But not too confidently: arrogance will backfire in the same way. Plan the points that you want to communicate, keeping the issues front and center and keeping the personal out. This will enable you to be calm, clear, careful but firm, and most importantly, present, when you speak.

Prepare, but don’t script

As mentioned previously, it can help to plan what you want to say by jotting down notes and key points before your conversation. However, drafting something word for word is not the way to go. Conversations of any kind rarely go according to plan. So when your boss goes off script, if all you know are your specific words, you will lose your way. With this in mind, prepare your points, but anticipate a variety of possible responses. By preparing to be flexible and present in the conversation, you will avoid being distracted by specific phrases you think you should say.

Timing is King

Timing and tact go hand in hand. Are your boss’s mornings always busy? Is he or she often distracted? Then consider setting up a dedicated meeting in the afternoon to have your conversation. Similarly, give thought to whether you believe others will agree with you. If you think they will, perhaps wait to confront your boss and gather insights and experiences from them to inform your thinking and your argument when you do speak to your manager. Being thoughtful about all of these details will contribute to a successful, productive conversation.

Similarly, once you are in the midst of the conversation, keep in mind that not all arguments can be won. There’s a time and place for everything, and this time might not be yours. If you have followed these steps and are standing up for your argument but your boss refuses to consider it, at a certain point it might be worth respecting their decision and making sure they know that they still have your full support. Your graciousness will bolster the trust that allowed you to disagree in the first place and keep your relationship intact (and perhaps even stronger) moving forward.

Stay humble and open

In difficult conversations like this, it is critical to stay open-minded. As soon as solutions, judgments or conclusions come into your mind, it can very difficult to approach the situation with any kind of creativity. Emphasize that what you’re offering is still only an opinion. Keep this in mind, and remember to qualify statements with phrases like “this is just my opinion.” Your manager will be able to sense your humility and open-mindedness, and it will go a long way toward the conversation’s productivity.


It may be something as simple as a thank you for your manager’s time and consideration. Or, depending on how serious the conversation becomes, something as formal as company paperwork. But every difficult conversation deserves a follow-up of some sort. This will bolster the professionalism and respect you have showed your manager and pave the way for a continued open, honest stream of communication between the two of you moving forward.



About the Author

Everwise connects employees with the people, resources and feedback they need to be more productive and successful at every stage of their career. Request a Demo: https://www.geteverwise.com/requestdemo/

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