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How To Have Difficult Conversations With Your Team

Written by: Mariela De La Mora, Executive Contributor

Executive Contributors at Brainz Magazine are handpicked and invited to contribute because of their knowledge and valuable insight within their area of expertise.


The number one most common topic I get asked about, especially by new people managers, is: “how do I have difficult conversations with my team members?” If you’ve also wondered, you are not alone in feeling challenged by this. All leaders, whether you’re a people manager or CEO, need to have tough conversations at some point. But there are ways to make those conversations as productive and painless as possible.

Reasons for difficult conversations:

  • Poor performance

  • Conflict within the team

  • Lack of communication

  • Negative feedback from peers

  • Layoffs or corporate restructures

As uncomfortable as these conversations can be, there are many benefits to having them. They can bring your teams closer together, invite them to problem-solve with you, and create a culture of leadership. When done effectively, they build trust and tell your team that they can approach you about anything.

Why difficult conversations are necessary:

  • Companies need effective communication to succeed and thrive.

  • 83% of employees appreciate receiving feedback, whether it’s positive or negative

  • You cannot lead by avoiding discomfort

  • You get better with practice!

Before having the conversation, you should reframe the idea that it needs to be difficult. Try not to get too worked up or anxious - it could turn out to not be a difficult conversation at all! Make sure to gather the facts and specific examples, and be prepared to offer resources or support if needed. Remember, approach the conversation knowing you both have the same end goal.

4 steps to navigating difficult conversations with your team:

1. Set expectations

Make sure you tell them ahead of time what you will be talking about, so that they don’t feel blindsided. Setting expectations for the conversation helps the information be better received and gives the other person time to mentally prepare. Schedule a time, and hold the conversation in private. If you’re doing it in person, book out a private room, or take them out for coffee outside of the office.

2. Check your assumptions

Take some time to reflect on the situation yourself. Were expectations actually set and clear? What assumptions had you made? How can you do your best to table those and go into the conversation with a clean mind?

3. Be specific

17% of employees feel that the feedback they receive is not specific enough. Avoid generalizations and provide specific examples to back up the feedback you are giving.

4. Focus on the solution, not the person

Instead of asking, “Why did you do this?” reframe the questions as: “Can you help me understand what happened?” And be open to feedback you were not expecting. You want to focus on the solution, not the problem, and make it a dialogue by asking for their help to decide what should happen to rectify it.

As with anything, you get better with practice. The purpose of these conversations is to build better relationships with your team and to “call them in” vs “call them out.” You’re on the same team, and hold the same vision. Remember that, lead with that, and you’ll be surprised at how much these conversations will reveal.


Mariela De La Mora, Executive Contributor Brainz Magazine

Mariela is a Life Coach and certified EQ Leadership Coach who helps women of color become powerhouse leaders of purpose-driven brands. Her mission is to help women of color break glass ceilings by healing the generational trauma and cultural conditioning holding them back from becoming the leader they can be.

She was named one of the top 10 leadership coaches by Yahoo Finance and has coached 6 and 7-figure CEOs and even leaders in the United Nations.

She previously spent 15 years in marketing while leading teams across the globe. As a 1st generation Mexican American, she was often the only woman of color in senior leadership and had to break past systemic and mindset barriers to do it.

She now helps women bridge that gap through trauma-informed life coaching and emotional intelligence development, so they can fully step into their power and lead with intention.



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