How to Navigate Difficult Conversations with Superiors

Conversations with superiors about sensitive or difficult topics can be daunting. But these conversations are a part of life and a successful career, so rather than shy away from them, develop skills that will help you feel comfortable approaching and navigating them effectively and confidently.

The Setup

You first should determine the person with whom to have a conversation. Do some research and make sure the person has the ability, either directly or indirectly, to accomplish your desired goal. For example, if you want to switch practice groups, make sure the person can make that happen. If you want a compensation adjustment, make sure the person can give you a raise (or at least has the ear of the person who can). If the person cannot meaningfully change things, your conversation likely will not be very productive from the outset.

Once you identify the right person, let them know you would like to schedule a meeting. How this should be done depends on your relationship with that person. If it is someone in your office, reaching out in person or over the phone may be fine. If it is someone with whom you have limited interaction, an email may be more appropriate.

The purpose of this initial contact is simply to request a meeting and set the table for a more meaningful conversation. Preview the topic and offer your availability for a meeting. Doing so will convey that the topic is important to you and will give the person notice and an opportunity to prepare, at least mentally, for the conversation. Once scheduled, send a calendar invite and, if possible, have the conversation in person, ideally in a neutral place (such as a conference room) to help limit distractions.

The Conversation

At the outset of your meeting, thank the person for taking the time to meet. Lawyers are busy, so simply acknowledging that the person is giving up time to meet with you shows that you recognize that they care. Clearly state your reason for the meeting and your intended goal or outcome, and be prepared with your ask. Explain why the topic is important to you personally and why it should be important to that person and the firm. For example, if you desire to switch practice groups, explain how you believe the other practice area aligns better with your skill set or interests, ultimately benefiting the firm. If you are having issues with a colleague, explain how that affects you and ultimately harms the firm.

Using data also can be persuasive. For instance, if you are seeking a raise and the market compensation recently has increased in your area, cite that data and frame it in the context of the firm: “We are going to struggle to attract and retain associates if we do not increase compensation to be more aligned with comparable firms in the area.” This shows that you care about the firm’s overall success and not just your personal gain.

Finally, “calm, cool, and collected” is a good mantra, but don’t be afraid to express genuine emotion as a signal that the topic is important to you.

The Closing

After your discussion, send the person an email thanking them for meeting with you and hearing you out. If you commit to providing follow-up information, such as additional examples or data to support your cause, follow through on that promptly and in an organized manner. Don’t have a successful meeting only to drop the ball on the follow-up!

Having difficult conversations can be, well, difficult. But, if you don’t ask, you won’t receive. Preparation and confidence when delivering your message are key to making conversations less difficult and more effective.