1. Predict the future.
When assigning projects, cover the questions that other supervisors forget to address but associates always need answered: What models should I follow? How much time should I spend before first contacting you? What do you plan to do with the work product I submit?
2. Look them in the eye.
Ask newer attorneys to meet with you for five minutes after each major assignment to address big-picture writing issues. Reviewing suggestions about specific sections—or even just one paragraph—is far better than spouting such generalities as “your writing needs improvement” or “you need to be clearer.”
3. Start soft.
Having trouble finding something positive to say? Ask yourself what you’d like to hear from a client who was dissatisfied with your work or with the disposition of a dispute. Compliment even the most misguided intentions: “It looks as though you tried to be comprehensive and thorough here.”
4. Turn the tables.
Help newer attorneys identify and solve their own writing problems. “What was your goal in framing the issue this way?” “How does this provision protect our client’s interests in the deal?” “What would you say if I asked you to sum up this document over the phone?”
5. Triage time.
Distinguish between your key writing goals and your idiosyncratic preferences. Before you make a change, ask yourself if it’s a fix that all senior attorneys would make, or if reasonable minds could disagree. Newer attorneys often see style quirks as proof that they shouldn’t even bother trying since you’re going to rewrite everything anyway. Focus on what matters most.