Step 2: Identify a Request
Identifying a concrete request keeps the conversation focused on actionable solutions rather than abstract feelings or perceptions. Asking someone to take a specific step is often far more effective and achievable than trying to change their mindset or emotions. Even in conversations where one or both people have new insights or awareness, including action items creates momentum and increases the value and impact of the conversation.
Develop a list of possible actions the person could take to improve the situation. Consider enlisting a creative colleague to help brainstorm alternatives. If the other person declines or seems uncomfortable with your request, view it as an opportunity for further discussion and mutual understanding. Invite the other person to share their own ideas regarding actions that could help address the issue. For example:
Golf Outing Exclusion (Mike’s Situation)
“Mike, would you be willing to host another golf outing in a few months where beginners are explicitly welcomed and encouraged to attend?”
“Would you attend the upcoming firm outing and make an extra effort to connect with all the new partners?”
Unfair Translation Requests (Min’s Situation)
“Can we establish clear guidelines for ordering translations and then address that in our next team meeting?”
“Moving forward, I would appreciate it if I were not asked to do translation work, as it is outside my role.”
“All Lives Matter” Comment
“Would you be willing to have coffee with me sometime next week so that we can have an open conversation about the phrase ‘Black Lives Matter’?”
“Would you be willing to watch this short video?”
Step 3: Set the Foundation for a Constructive Conversation
If you have a very strong relationship with the person, the following questions may be less critical to the success of your conversation. However, in most cases, considering these preparatory topics will help you determine the best approach and frame the discussion constructively. Even if you don’t articulate these elements explicitly, they will shape your mindset and influence how you engage in the conversation.
While none of the topics below specifically address managing emotions, reflecting on them can often help diffuse anger or other negative feelings. However, if you find yourself too upset to engage constructively, consider these tips for managing emotions before a difficult conversation.
What Do You Like or Respect About the Person?
People can sense respect, and there is no way to fake it. That’s why it’s important to identify at least one quality you genuinely appreciate or admire about the other person and keep it in mind as you prepare for the conversation. Whether or not you choose to mention it directly, focusing on their positive traits will help you relate to one another. Even if you find the person difficult, identify at least one positive quality. For example:
“Mike is hardworking and committed to the firm’s success.”
Genuine respect shifts your tone in subtle ways that make the conversation more productive.
What Do They Care About?
Virtually anything that the other person cares about or considers important can provide a good starting point for the conversation. A lawyer’s sense of belonging — an aspect of psychological safety — affects business outcomes.
Think about how the person acts and the topics they raise in meetings and in their casual conversations. These provide clues that indicate their values. Look particularly for shared interests, such as firm growth, client satisfaction, or business development. Once you identified one of their values, orient the conversation around that topic. For example:
“We all want to make sure this firm is as successful as possible, and having a fair compensation system is important for retaining the best partners.”
What Is Your Role in the Situation, If Any?
Taking responsibility for even a tiny part of the situation can make the conversation far more productive. These discussions often carry a high risk of the other person feeling criticized, so offering even a minor apology can help create an atmosphere of collaboration and mutual problem-solving rather than one of blame and defensiveness.
Think about if there is anything you could have said or done to create clearer expectations or policies. If you had addressed the issue earlier, could it have prevented the situation from escalating? For example:
“I’m sorry for not raising this concern earlier, since that may have prevented some of the stress about this.”
What Is the Person’s Perspective?
If you want people to understand your perspective, a great starting point is to first understand theirs. Take time to think through your questions in advance so that you can ask them at the right moment in the conversation. What do you want to learn or understand from the conversation? Use open-ended questions. Avoid leading questions. For example:
“What factors do you think are leading to women partners having lower compensation than male partners?”
Turning Difficult Conversations into Meaningful Change
Addressing DEIB-related issues in the workplace is not always easy, but these conversations are essential for building a more inclusive and equitable environment. Thinking through the key elements outlined above will help you craft your message and approach discussions with curiosity and respect. By taking the foundational step of thoroughly preparing for difficult conversations, your discussions can lead to better policies, more inclusive practices, and a stronger, more cohesive firm culture.