How To Have A Difficult Conversation With A Supervisor Who Supports A Toxic Work Culture In 4 Easy Steps

When you raise your voice, you raise your value.

Hi FairyGodMentor,

How do you have difficult conversations with a supervisor who has not found their “why” and promotes a toxic culture?

Yours Truly, Scared Silent

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Dear Scared Silent,

First, I want to acknowledge and celebrate your courage for reaching out, showing your ASK, and requesting support while working in a toxic work culture. It’s not easy and it’s evident that you desire to improve the quality of your work/life and others that may be negatively impacted.

To quote Mahatma Gandhi, “Be the change you wish to see in the world.” We have to power to make the positive change we’d like to see in the workplace by practicing self-advocacy. Self-advocacy means speaking up for your needs, communicating your goals, and making boundaries. It also fuels career and leadership growth.

Having difficult conversations with a supervisor, especially one who is not aligned with their purpose or “why” can be very intimidating and even scary. I’ve created some survival tips to help guide you and others on RISE to higher heights using this type of assertive communication:

Reflect: Gain clarity on your needs and limits. Understand what your limits are. Ask yourself: What do you need to do and feel your best at work?
Identify: Discover a time that works best to talk to your supervisor. I know that you’d rather avoid having this tough conversation, but nothing is going to change until you speak up. You are a priority! Make your needs an agenda item for your next one-on-one conversation or set up a separate time to discuss.
Strategize: Craft your conversation. It’s best to have a script prepared so that you can stay on topic, especially if emotions are running high. Create a specific script of your talking points that you want to cover. Be clear and concise. I worked with an executive who liked things “right and tight.” Keep that in mind when communicating with people-leaders. No fluff. Stick to facts. If you’re asking for a behavior or workload change, focus on the why (impact to you, your team, and business) behind the what (the ask/the feedback/etc.). Focus on the impact and not the person. How is this behavior or action impacting you, the team, and the organization? Don’t forget to frame the conversation with empathy. You’ll want to open the conversation setting the intention of collaboration and support. You’re having this discussion out of concern for the success of your professional relationship (if you have one), the team, and the overall success of the organization. Use “I” statements to fully express how you’re feeling so you’re not putting the receiver of the feedback on the defensive. It may sound like “I think we can both agree that we have a shared desire to make sure the team and the business are successful. And you want us to be productive, right? I’d like to share some insights on some recent behaviors I’ve witnessed and their impact on me and the team. Then, I’d like to discuss some solutions on how we can create more harmony in the workplace together.”
Execute: This is where the rubber meets the road. Prepare, speak, listen, and then clarify. Before you have this discussion, you’ll want to prepare to overcome any challenges you may face. Anticipate the questions that may be asked for clarity. Feedback is a gift. People may take it, use it, or throw it away. Based on what you shared about this leader, prepare yourself for some resistance and deflection (throwing things back onto you) that may take place.

You’ll want to practice for this type of conversation. Make sure to role-play with a trusted colleague or mentor. Stick to your script. Once you’ve said what you need to share with your supervisor, pause and listen for a response. Remember, this conversation intends to come from a place of collaboration and support. As a leader, (remember you don’t have to be a people manager to be a leader), you’ll want to focus on solutions, not the problems at hand. You’ll want to actively listen to what your supervisor has to say and then work together to come up with a solution that will work best for both of you. Real talk, the solution may mean working with a different leader or finding a new place to work, if that’s an option.

If you’ve tried to have this type of difficult conversation and the toxicity persists in the workplace, I would highly suggest you bubble this matter up to Human Resources. Ask to have them present to mediate future conversations, especially if you’ve tried to resolve this on your own.

Keep your receipts and take notes. Send a copy of what was discussed to your supervisor and Human Resources. This protects you and the organization.

I say this all of the time, Scared Silent: when you raise your voice, you raise your value. You have value and it’s important to voice your concerns and be heard. By reflecting on your needs and limits, identifying the right time to discuss, strategizing your conversation talking points, and executing your discussion by being fully prepared to overcome challenges, you’re on your way to fostering meaningful change in the workplace. Be the change!

You got this!

With love and light,

Your FairyGodMentor®

Joyel Crawford is an award-winning career and leadership development professional and the founder of Crawford Leadership Strategies, a consultancy that develops empowered, results-driven leaders through engaging leadership development coaching, training, and facilitation. She is the author of the best-selling book and audiobook Show Your Ask: Using Your Voice to Advocate for Yourself and Your Career.

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