How To Have a Difficult Conversation With Your Boss

How to have a difficult conversation with your boss
  1. Request a meeting. …
  2. Shift your mindset. …
  3. Gather your thoughts. …
  4. Be cognizant of your language and tone. …
  5. Address the issue directly. …
  6. Actively listen to your boss’s perspective. …
  7. Reach a resolution.

Management inevitably involves having difficult conversations, whether you’re informing a client that a project is running behind schedule or presiding over a performance review that lacks enthusiasm. How can you manage the exchange to go as smoothly as possible, how should you prepare for this type of discussion, and how do you find the right words in the moment?

What the Experts Have to Say Holly Weeks, author of Failure to Communicate, says, “We’ve all had bad experiences with these kinds of conversations in the past. Perhaps your direct report started crying during a performance review, your boss yelled at you during an argument, or your client hung up the phone on you. As a result, we tend to avoid them. But that’s not the right answer. After all, according to Jean-Francois Manzoni, professor of human resources and organizational development at INSEAD, “tough conversations are not black swans.” The trick, he says, is to figure out how to deal with them so that “a better outcome: less pain for you, and less pain for the person you’re talking to” results. Here’s how to have these difficult conversations and come away with what you need while still maintaining your relationships.

Change your perspective If you’re preparing for a conversation you’ve classified as “difficult,” you’re more likely to feel anxious and upset about it in the lead-up to the conversation. Manzoni recommends “framing it in a positive, less binary” manner as an alternative. For instance, you are having a productive conversation about development rather than providing negative performance feedback. You don’t say “no” to your boss; instead, you suggest a different course of action. Weeks claims that approaching a challenging conversation as if it were just another regular conversation helps it go more smoothly.

Breathe Manzoni asserts that you will be more adept at handling challenging conversations if you are calm and collected. Taking frequent breaks throughout the day to engage in “mindful breathing” is advised. This “refocuses” you and “enables you to take any blows” that may be directed at you. This technique also works well in the moment. For instance, if a coworker approaches you with a problem that could lead to a difficult conversation, step away from the situation—get a cup of coffee or take a quick lap around the office—and gather your thoughts.

Plan but don’t script It can be beneficial to prepare your remarks in advance by making notes and outlining your main points. Drafting a script, however, is a waste of time. Weeks asserts that there is a slim chance that things will go according to your plan. The exchange “becomes weirdly artificial” because your counterpart doesn’t know “his lines,” so when he deviates from them, you have no forward momentum. Your approach should be “flexible” and include “a repertoire of potential responses,” advises Weeks. She continues, “Your language should be straightforward, direct, and neutral.”

Recognize the viewpoint of your conversant Avoid entering a difficult conversation with a “my-way-or-the-highway” mentality. Weeks advises asking yourself two questions before bringing up the subject: “What is the problem, and what does the other person think is the problem?” If you are unsure of the other person’s perspective, “acknowledge that you don’t know, and ask,” she says. Show your counterpart “that you care,” says Manzoni. He continues, “Take time to process the other person’s words and tone,” and “express your interest in understanding how the other person feels.” Once you hear it, look for areas where your viewpoint and that of your counterpart coincide.

Be sympathetic, says Manzoni, “Experience tells us that these kinds of conversations frequently result in [strained] working relationships, which can be painful.” Therefore, it is wise to approach delicate subjects from a place of empathy. Be considerate; be compassionate. “You can manage to deliver difficult news in a courageous, honest, and fair way, even if it isn’t always pleasant,” ” At the same time, “do not emote,” says Weeks. The worst thing you can do, she advises, “is to beg for sympathy from your counterpart.” Sayings like “I feel so bad about saying this” or “This is really hard for me to do” are inappropriate, she advises. “Don’t play the victim. ”.

Manzoni advises attempting to “slow the pace” of the conversation in order to prevent tensions from escalating. Slowing your speech rate and pausing before answering the other person tends to “defuse negative emotion” from your counterpart and “gives you a chance to find the right words,” he says. The conversation always turns out better if you pay attention to what the other person is saying, he claims. “If you address the right issues, the conversation always turns out better.” Make sure your actions reinforce your words, adds Weeks. Saying “I hear you” while using a smartphone is disrespectful. ”.

Ask yourself, “Is there something I can give back?” before starting a conversation that will “put the other person in a difficult position or take something away from them,” advises Weeks. You could say, “I have written what I think is a strong recommendation for you; would you like to see it?” if you need to inform your boss that you can’t take on a specific assignment. If you need to lay off someone you’ve worked with for a while. “Be constructive,” says Manzoni. Nobody wants problems. “Offering options demonstrates respect for the other person and aids them in seeing a solution. ”.

Consider what went well and what didn’t after a difficult conversation in order to reflect and learn, advises Manzoni. “Reflect on the reasons behind your actions and consider alternative phrases you could have used.” Weeks also suggests observing how other people handle these circumstances and adopting their strategies. Learn to disarm yourself by acting out what you observe, she advises. “Having a successful difficult conversation is more than just a skill; it takes courage.” ”.

Case Study #1: Be direct, clear, and emotionless Tabatha Turman is the founder and CEO of Integrated Finance and Accounting Solutions, a financial company with clients in both the public and private sectors. She was aware that there was something wrong with a particular employee. He was kind and put in a lot of time, but his output was a problem, she claims. “He wasn’t right for the position he was in. ”.

After six months, she and her team tried a number of interventions, including having him work with a qualified coach, but she realized that something had to be done. We kept pushing the issue off, but I came to the realization that I would have to play the villain. ” She was going to have to lay him off.

Tabatha used her 20 years of experience as an army officer to prepare for the conversation. She claims, “I grew up in a military setting where there is no bluff.” “When you’re at work, you’re at work. You must remain resilient for those around you and distance yourself from your emotions. ”.

Her words were simple. He “was not a good fit,” she told the worker. She gave details about the severance package after explaining that the company would retain him until the end of the month. While the employee “wasn’t happy,” according to Tabatha, he accepted the layoff “like a trooper.” ”.

She reminded herself of her good intentions before even bringing up the subject with the employee. “Going into something like this, you need to have the right energy.” It won’t be a productive conversation if you’re coming from a place of frustration, which can happen because we’re all human. The best way for this person to hear the message must be considered.

Bob Bordone Teaches You How to Have a Difficult Conversation with Your Boss

Why it’s important to have difficult conversations with a manager

In order to improve whatever situation you’re addressing, it’s crucial to have difficult conversations with a manager. Even though having difficult conversations can be difficult, they can help you come to a successful conclusion. Having difficult conversations could result in:

How to have a difficult conversation with your boss

You can follow these steps to have a challenging conversation with your manager:

1. Request a meeting

Having difficult conversations with your manager in person is always a good idea because you can be sure that they are fully focused on you. It also guarantees that you’re approaching them at a time that works with their schedule and when they’re most likely to be open to hearing what you have to say.

Keep your message as brief as you can when you ask to speak with them privately. Say, “I would like to talk about my performance review,” for instance. When would be a good time for you?”.

2. Shift your mindset

Before speaking with your manager, you should first change your perspective. You’re more likely to feel upset or anxious before speaking to them if you already believe that the conversation will be challenging. Instead, try viewing the meeting as a chance for a fruitful conversation. It is likely to go the best and be the least stressful for you if you approach it as a regular conversation.

3. Gather your thoughts

It can be helpful to prepare your remarks before engaging in any difficult conversations. The best way to do this is to put your main talking points in writing before the conversation. Making notes of the key points you wish to discuss will enable you to be adaptable and ready with a range of potential responses depending on how the conversation develops.

It’s a good idea to consider potential solutions to your issue in advance as well. You can demonstrate to your boss that you gave the situation careful thought and that you want the meeting to be as fruitful as possible by coming prepared with a range of solutions. For instance, be ready to offer a workable alternative solution if you are struggling with your current workload or with a particular project.

4. Be cognizant of your language and tone

It’s crucial to be conscious of the language you use and the tone of your voice. You should speak in plain English with a neutral tone. It’s crucial to remember that maintaining composure can make difficult conversations go more smoothly and assist you in getting the desired outcome.

5. Address the issue directly

Start the conversation with your manager by outlining the purpose of the discussion right away. Additionally, it’s a good idea to express your gratitude for them meeting with you at this time. You could say, “Thank you so much for finding time in your schedule to talk, for instance.” I know you have a lot going on. I wanted to meet because I’ve been having trouble balancing work and life, and I wanted to talk about the possibility of working from home part-time. “.

You can contribute to creating a positive atmosphere for the meeting by expressing your gratitude right away. Additionally, you demonstrate your respect for their time by focusing the conversation right away on the reason for the meeting.

6. Actively listen to your bosss perspective

Ask your boss to share their thoughts on the situation after you’ve given them. They might share your worries or view the subject from a different angle. However, if you pay attention to what they have to say, you’ll be much more likely to address the proper problems and get a better outcome.

Pay attention to your own verbal and nonverbal cues as you listen to your boss’s feedback. You want to come off as receptive and willing to hear what they have to say. If you need to clarify something, do so, and if you don’t like their answer, you might want to elaborate. However, be careful to avoid becoming defensive.

7. Reach a resolution

Make note of any areas where your manager and you may hold opposing views, and try to negotiate a solution that both of you can accept. Ask if there are any specific objectives you can work toward that would persuade them to change their mind, for instance, if the conversation’s goal was to negotiate a salary increase and it is not possible at this time. If so, request a deadline for those objectives as well as a specific time when you can bring up the possibility of a raise.

The aim of the conversation should be to increase openness between you and your boss in order to achieve both of your objectives. A positive work environment and a more effective and productive team can result from open communication between you and your boss.


How do you talk to your boss that things bother you?

5 steps to help you navigate through difficult conversations
  1. Consider the situation from their perspective. We frequently find that conversations are challenging because we are fixated on our own point of view.
  2. Have a goal in mind, but be flexible. …
  3. Work on your listening skills. …
  4. Take care of yourself. …
  5. Brainstorm solutions together.

How do you make a conversation uncomfortable at work?

  1. Time Your Concerns Appropriately. Your first objective should be to voice your concerns in a respectful manner.
  2. Be Specific. …
  3. Be Objective, and Lose Your Emotional Attachments. …
  4. Come With Solutions in Mind. …
  5. Focus on the Positives. …
  6. Leave the Decision Up to the Boss. …
  7. Get Support If Necessary.

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