How to have a difficult conversation with your boss
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How to have a difficult conversation with your boss

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How to have a difficult conversation with your boss

By Stephanie Vozza

Being called into the boss’s office for a private conversation is intimidating. The request can leave you worried about your job security. If you aren’t happy at work, however, you may be the one who wants to initiate a discussion. That’s intimidating, too, due to the inherent power dynamics at play, says Shelly Tygielski, coauthor of How We Ended Racism: Realizing a New Possibility in One Generation and founder of the grassroots aid organization, Pandemic of Love.

“The superior-subordinate relationship can naturally intensify feelings of vulnerability and apprehension when broaching challenging topics,” she says. “First and foremost, it’s crucial to recognize and respect the hierarchical structure within the organization. This doesn’t mean suppressing valid concerns, but rather framing them in a manner that’s constructive and solution-oriented.”

Nicole Bianchi, author of Five Tough Talks: How to Lead Brave Conversations for Exceptional Results, says talking to your boss about something difficult is probably the most dreaded conversation. “The conversations you have down or to the side [of the hierarchical chart] are tough,” she says. “But the toughest is the one you have to have up.”

Instead of remaining unhappy or quitting, address your concerns with your boss by taking these five steps:

1. MAKE SURE EXPECTATIONS ARE SET

The first foundational conversation every employee should have with their leader should be about expectations. “It’s common to talk about the what, but sometimes we don’t get to the how,” says Bianchi. “We often have expectations in our mind, but we never articulate them. That’s where misunderstandings start to happen.”

If your leader doesn’t initiate this conversation with you early on, take the reins, says Bianchi. “If you ever need to challenge your leader and give them feedback, how are you going to do that?” she says. “Having that conversation makes sure everyone understands their role.”

2. BE CLEAR ON THE FACTS

It’s easy to become influenced by your biases, derailing the conversation. Instead, go into the discussion with a firm grasp of what’s true, says Justin Michael Williams, coauthor of?How We Ended Racism. He suggests creating two columns on a sheet of paper. On the left side, write “Here are the facts,” and on the right side, write “Here are the assumptions and stories I’m making up.” List inarguable facts on the left side, remembering that feelings aren’t facts. Then, note your feelings, emotions, biases, and stories on the right side.

“Once you get all that down on the page, it will bring you to the final question, ‘What realizations have you come to now that you have separated the facts and stories?’” says Williams.?“If we don’t take the time to understand the difference between facts, biases, and stories, we end up pointing the finger of blame at each other and arguing over whose biases are more important.”

3. CONSIDER THE OUTCOME YOU WANT

Once expectations are clear and you’ve separated feelings from facts, identify your objectives and goals for the conversation.

“Get clear,” says Bianchi. “What are you looking for in the situation? What’s your intent by having this conversation? And then go deeper. How are you feeling about it? How might they be feeling about it?”

We often enter difficult conversations with a premeditated idea of what we’d like the outcome to be, leaving no space for collaboration, says Williams.

“The best solutions arise when both parties can explore ideas for solutions together,” he says. “Otherwise, the person you’re speaking with will feel like something is being forced upon them, and that never works in the long run. It often ignites a pattern of shame, blame, and guilt. Forcing your solution onto a person or trying to elicit an action that they aren’t authentically on board to take leads to empty actions.”?

4. PRACTICE THE CONVERSATION

People tend to be less confident when speaking off the cuff. Bianchi suggests being clear on the message you want to say by creating a script. Once you’ve got your words down, run through the conversation aloud.

“You can practice in front of a mirror or with somebody you know and trust who can give you feedback on how things are landing,” she says.

5. APPROACH YOUR?BOSS?

Don’t wait too long for a conversation. If you notice something different with your leader, it’s best to address it immediately instead of ruminating. Start the conversation with, “I want to share something with you that you may not be seeing,” and ask for permission to share your thoughts, suggests Bianchi. “It assumes positive intent,” she says.

Instead of going into the conversation on the attack, call your boss forward, says Tygielski. “When you call someone forward, you are essentially inviting them into a dialogue where concerns can be shared openly, feedback can be given without judgment, and both parties can work together to find a solution or understanding,” she says. “This is different from calling someone out, which often implies pointing out someone’s flaws or mistakes in a confrontational manner.”

To call your boss forward, approach them with respect, take a solution-oriented mindset, and choose the timing wisely. “When this concept is applied to a professional setting, especially when dealing with superiors like one’s boss, it becomes even more critical,” says Tygielski. “Engaging in a conversation with a boss requires a careful balance of honesty, tact, and professionalism.”

While swift action is beneficial, Bianchi says some conversations need deeper preparation. “Take a couple of days to prepare and get ready,” she says.

Instead of accusations and blame, take an open mindset, says Williams.?“Sharing your emotions and how you feel about something opens a space of vulnerability and connection,” he says. “This is the space that’s needed for real change to occur.”


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Melvin Hendrix

Collaborative Agronomic Partnerships Consultant; Solutions Creator

1 年

What's interesting to me is how zero comments have been made to this article. Either the substance is so good, no response is necessary. Or, so irrelevant that engaging is not worth the time. Neither of these, of course, is true. What is true is that some workplaces are toxic, and the person(s) that can fix the issues are part of the problem or the main cause of the toxicity. Having worked in a variety of environments, including the aforementioned, the strategy discussed here works primarily where communication is open. In the first instance, an employee should be looking for an alternative situation.

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