Tag Archives: difficult conversations at work
June 5, 2024 How to Set the Stage for a Tough Conversation (4 Ways)

As a leader, tough conversations are inevitable. There will come a point when you’ll need to deliver some less-than-great news, provide negative feedback, or make a difficult request. And avoiding these types of tough conversations is NOT the answer. In many cases, the more you delay, the more difficult the discussion will be once you eventually have it.
However, it IS possible to effectively set the stage for tough interactions. This will help to soften any difficult blows and provide a safe space for feedback, commentary, and questions. Let’s talk about four ways to set the stage for tough conversations.
Choose an Appropriate Time and Setting
Where and when you decide to meet can make a huge difference. When talking about a sensitive issue, it is best to find a quiet, comfortable, and private place to speak. Make sure to choose a time when both parties will be free from distractions and able to focus on the conversation. This will ensure a more productive and respectful dialogue. By setting the stage appropriately, you create an atmosphere conducive to open communication and problem-solving. Additionally, being mindful of the environment can help create a sense of safety and comfort, encouraging honesty and transparency during tough conversations.
Be Transparent
When inviting someone to engage in a difficult conversation, it is usually best to be transparent and clear about the purpose of the conversation. This transparency will help to avoid confusion and set the right expectations. Clearly stating the reason for the discussion allows both parties to prepare mentally and emotionally. It also establishes trust and shows respect for the other person’s time and feelings. Open communication from the start fosters a more constructive and meaningful dialogue.
Prepare
Before engaging in the conversation, it is essential to prepare yourself for a variety of questions and reactions. Anticipate what the other person might ask or what pushback they might have. Consider different scenarios and prepare appropriate responses. I encourage you to practice out loud in front of a mirror, even if that seems a little odd at the time! It really does help. This preparation will help you stay composed and focused during the conversation. Being mentally ready for various outcomes demonstrates your commitment to handling the tough conversation effectively. Moreover, preparation allows you to convey your message clearly and logically, reducing the chances of misunderstandings or conflicts. Remember, the more prepared you are, the more confident you’ll be in navigating challenging discussions.
Commit to Empathy
In my experience, the most productive conversations are ones in which both parties feel that they are listened to, respected, and understood. Make a commitment to enter the conversation with empathy. That means actively listening, asking appropriate questions, and aiming for understanding. Ensuring that both parties feel heard and valued fosters a collaborative environment where tough conversations can lead to growth and improved relationships. By showing empathy, you create a safe space for open dialogue, allowing each person to express themselves honestly and without judgment.
Remember, the goal of these conversations is not only to address challenges but also to strengthen trust and understanding between individuals. Practicing empathy can transform difficult discussions into opportunities for positive change and progress.
While it’s never fun to engage in a tough conversation, it is often necessary to do so in order to clear the air, make positive progress, and/or benefit the organization. By approaching your difficult conversations with empathy and tact, you can create a more positive outcome that leads to growth and understanding.
MARGARET SMITH IS A CAREER COACH, AUTHOR, INSIGHTS® DISCOVERY (AND DEEPER DISCOVERY) LICENSED PRACTITIONER, AND FOUNDER OF UXL. SHE HOSTS WORKSHOPS FOR PEOPLE WHO NEED CAREER OR PERSONAL GUIDANCE.
CHECK OUT MARGARET’S ONLINE LEADERSHIP COURSE.
Tags: difficult conversations at work, engaging in difficult conversations, how to deal with tough conversations, Margaret Smith business coach, margaret smith career coach, set stage for tough conversations
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May 19, 2021 Keep Calm…and Dare to Have Difficult Conversations

It’s no surprise that many of us tend to avoid difficult conversations. Why would we want to make ourselves uncomfortable or become the subject of someone’s wrath? Why would we want to potentially open a can of worms?
Though difficult conversations are just that—difficult—they are also sometimes necessary for improving the present climate or paving the way to a better future. Though you may be reluctant, or even a little scared, to engage in difficult conversations, oftentimes they are necessary and can actually improve things, going forward.
Here are 4 reasons to dare to hold difficult conversations:
[NOTE: In past blog posts I’ve talked about how to prepare for difficult conversations. See this post about the D4 Model and this newsletter about the 5 P’s of Courage for more…]
1. They can set the record straight
In many workplaces, rumors fly and reality can get twisted or obscured. If you’re in a situation where you’re uncertain of the truth, it’s best to sit down with the people involved and get to the bottom of it. It might be as simple as figuring out who was in charge of a certain report or who neglected to contact a client when that needed to happen. The purpose of this conversation isn’t to place blame, but rather to uncover the truth and begin to problem solve.
This type of conversation can also help you put safeguards in place so that the same unfortunate situation doesn’t happen again. It’s possible that it’s no one’s “fault” and the system simply needs a bit of an overhaul.
2. They can provide forward motion
Sometimes when we fail to confront a difficult situation, that can lead to stagnation. The office might be so hung up or distracted by a single person’s (or a group of people’s) actions that it becomes their primary focus. To get the wagon wheel out of the rut, you need to face the situation head-on and engage in a potentially difficult conversation(s).
EXAMPLE: Let’s say Kim hasn’t been turning in her reports on time, which, in turn affects the rest of her team’s progress. Everyone is upset and productivity is down. To get past this rut, you’ll have to bite the bullet and have a conversation with Kim. It could be that Kim was unaware of her responsibilities or didn’t understand the dominoes affect her tardiness was having. It’s possible Kim has felt unsupported or unmotivated lately (in which case, maybe she’s in the wrong role). Regardless, having this conversation can help move your entire team from a place of stagnation to forward movement and problem-solving.
3. They can start dialogues
You may not truly understand someone’s actions, or what is going on in their head, until you speak with them. It’s possible a situation is more complex than you realized (for instance, maybe someone is constantly late for their 8 a.m. Zoom meetings because they have to drop their kids off at daycare). It’s also possible that the other person hasn’t understood the consequences of their recent actions. Sitting down and having a conversation can help create a bridge of understanding. It can open dialogues and help both sides understand what is broken and how to go about fixing things.
4. They can earn you respect, as a leader
Effective leaders have to make hard decisions and engage in difficult conversations regularly. That’s the reality. If you gain a reputation as someone who avoids problems and lets things “work themselves out,” you won’t gain much respect. If, however, you are known to tackle problems head-on and address issues as soon as you notice them, you’ll be seen as a proactive leader who has a real stake in the wellbeing of your team. What’s more, people will come to understand that you will hold others accountable for their actions and you will act in the best interest of the team. Your people will know you have their backs.
Instead of shying away from difficult conversations, embrace them! Start seeing them as opportunities to have fruitful conversations that move your team forward. Tough conversations can be uncomfortable or daunting, but the rewards are ultimately worth it. This comes with the territory when you’re a leader, and it’s a good idea to make lemonade with whatever lemons the workplace throws at you.
MARGARET SMITH IS A CAREER COACH, AUTHOR, INSIGHTS® DISCOVERY (AND DEEPER DISCOVERY) LICENSED PRACTITIONER, AND FOUNDER OF UXL. SHE HOSTS WORKSHOPS FOR PEOPLE WHO NEED CAREER OR PERSONAL GUIDANCE.
CHECK OUT MARGARET’S ONLINE LEADERSHIP COURSE.
Tags: difficult conversations at work, having difficult conversations, leadership and difficult conversations, Margaret Smith business coach, margaret smith career coach, navigating tough conversations
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