Five Tips for Supervising Associates

Every once in a while, I get contacted by a former writing student asking for assistance with a new writing challenge – being an effective supervisor. In particular, they are looking for help on how to use my coaching techniques to provide better writing feedback to their junior associates.

If you are interested in my advice on this topic, read on for five tips on how to coach your associates to achieve meaningful improvement in their writing.

Tip 1: Show them quality writing

As you know, young associates tend to produce their advice by copying/pasting text from the law as well as from sample advice in your firm’s files. Unfortunately, this combination is oftentimes a recipe for creating a masterpiece of painfully complex writing due to (i) the inability of legislatures to produce comprehensible laws and (ii) some of the advice in your firm’s files is – to put it politely – not that great from a stylistic perspective.

If you want to help your young colleagues avoid picking up bad habits, why not provide them with a few examples of quality writing to learn from? In this case, I recommend providing a few explanations to them about why you think such examples are so stellar.

Tip 2: Give them actionable advice

When you are feeling especially overburdened and tired, it’s easy to provide feedback on writing that is accurate, but also utterly unusable. For example, if you tell them that a sentence is long and complicated, you are probably right about this feeling – but how are they supposed to use such vague intelligence?

Instead, try to control your instincts and limit your comments to specific advice that is immediately actionable and easy to repeat in the future (e.g. make sure you address the client’s question in the first three paragraphs). If you still think it’s important to communicate your frustration about problems lacking immediately actionable advice, I recommend setting aside the problems to a later point when you have the time and energy to sit down and with the associate and collaborate on a solution to the problem.

Tip 3: Recommend Resources

When I was an associate, my best supervisors were the ones that went out of the way to provide me with the resources for solving my own writing problems. Usually these supervisors would recommend that I check out some useful writing resource. For example, in our Chicago office, the lawyers liked to frequently refer to the classic writing style guide The Elements of Style (aka Strunk & White).

Tip 4: Help them switch perspectives

I’ve learned the most about writing well by playing the role of an editor. In this role, not only is it a lot easier to feel the problem with a given piece of writing but it also forces you to find the solution to the problem.

You can greatly boost the writing development of your associates by asking them to switch perspectives and assume the role of a supervisor. If you would like to try this out, I recommend two different options. First, you can give them a short piece of painful prose and ask them to edit it for style. Second, you can have your associates engage in peer review by asking them to edit the writing of their colleagues.

With either of the above approaches, you will definitely help them understand the importance of producing clear writing. As an added bonus, they will also be more appreciative of your efforts as their supervisor.

Tips 5: Prioritize their learning

Last, but not least, you want to make sure that you prioritize their opportunities to develop themselves. In particular, I recommend that you explicitly communicate the importance for them to attend and participate in your firm’s L&D programs. Such communications will reduce the likelihood that they will skip out on important learning programs due to a misbelief that you only care about client work.