Having a Difficult Conversation with Your Legal Team

Forget Hopeful Subtleties and Get to the Point

Be direct in a difficult conversation with a legal team member
nullplus/E+/Getty Images.

It’s not exactly a trade secret that many lawyers are not exactly the best supervisors. Managerial skills are not something we typically picked up in law school, and the role models we may have worked for are likely to have been less than ideal anyway. The first time I served as a project manager as a lawyer, every conversation with team members was difficult for me given my lack of managerial experience and the fact that my team was made up of my peers.

I’d hesitate just in asking someone to do something and definitely didn’t provide pertinent feedback when the deliverable fell short of my expectations. Too often, I’d just make corrections myself and move on. I was frustrated and even somewhat annoyed to have been given the responsibility for managing a project that I hadn’t sought or volunteered for. As much as I should have appreciated that my own managers thought me up to the task, I begrudged the fact that I had to undertake it. I didn’t want to be a manager; I wanted to practice law.

I’ve learned. That hope-for-the-best-while-subtly-asking-for-help approach might work, maybe, for a little while, but there just isn’t enough time to doodle around hoping your team will absorb merely by osmosis what you want, need, and expect. You are going to need to instruct them with greater precision than you probably ever imagined. You will probably need to guide them more than once.

Even as managing the day-to-day routine of a legal team may become easier, it may be a greater while before difficult conversations with individual team members become painless. Difficult conversations tend to be needed when there has been a failure in performance of some sort — whether it’s by a member of the team, by the supervisor (you), or by upper management generally.

These are the sorts of conversations where a grim reality will need to be conveyed and a request for behavior that is modified must be made.

Of course, the subject of the conversation very much will drive the tenor and content of any difficult meeting. Even so, the following tips can help you reach the outcome you want while clarifying for the legal team member exactly what is expected.

1. Prioritize

Before having the conversation, identify for yourself the best possible result that you would like to achieve. It may be that a paralegal becomes more thorough in his research or that a secretary becomes more professional in her interactions with clients. It could be that a younger lawyer takes greater responsibility for bringing in work. Presumably, the best-case scenario is that the team member strengthens his performance and does not quit. Identifying what you want the outcome to be will make it easier for you to achieve it.

2. Practice

Review various scenarios likely to occur during the conversation and rehearse your responses to those. Is the team member likely to give excuses as to his poor performance, blame others, blame you, or just flat-out refuse to make a change? Anticipate the team member’s possible responses and be prepared to address them.

3. Display Candor

Let the team member know that you are the bearer of bad news. If you can, you might cushion the news with a bit of a compliment. (“I know you tried hard on a tough deadline, but that brief could not be presented to the client.”) If you’ve had similar conversations with the team member before, though, and change in the direction you want it is still not occurring, now is the time to be more straightforward. You might begin, “We are having this conversation today because we’ve talked in the past about how your legal analyses are sometimes lacking in accuracy.” Then explain why the situation is intolerable — how it impacts the firm’s reputation, how a client has been or could be impacted negatively, how even the firm itself may no longer be sustainable with this quality of work product.

4. Provide Context

Review how you’ve gotten to that point — whether you’re talking about shrinking firm revenues or poor quality service. Be as precise and as candid as you can be given business considerations, client confidentiality, and legal and privacy concerns. If a team member can understand why the situation is as it is and how his performance fits into the organization as a whole (“when you miss vital caselaw, other members of the team have to scrutinize and even redo your work, which drives up expenses”), he may be much more accepting of the need for change.

5. Listen

Allow some time for explanations, excuses, or general whining. Acknowledge that the situation is challenging, make additional suggestions for changes in behavior, and then propose that the team member uses past performance as a learning opportunity. In short, leave the past in the past and specify how the situation will change moving forward.

6. Set Goals

Let the team member know what the next steps are and what the consequences will be if those measures are not taken. Will the team member be reassigned, given additional training, or let go if performance does not improve?

7. Establish a Deadline

Set a date to revisit this issue, whether it’s in a few days, a week, or six months. Even if you do not meet formally about this matter again, be certain to follow up either in informal interactions or by email. Be encouraging where the team member makes a positive change, and provide guidance where additional improvement is needed.

Difficult conversations are just that: difficult. Avoiding them or soft-pedaling the seriousness of these talks isn’t likely to improve the situation. Get right to it: explain the problem, specify expectations and a timetable for meeting them, and then follow up.