Don't Be Afraid of Questions

A Guest Post from Emily Logan Stedman

Today’s awesome guest post comes from one of my favorite LinkedIn Lawyers: Emily Logan Stedman. Emily is a Partner a Commercial Litigation Partner at Husch Blackwell in Milwaukee, Wisconsin. She regularly posts advice for junior lawyers to her more than 20,00 followers. Plus she was one of the most-downloaded episodes of 2024 on How I Lawyer (listen here). Here is Emily:

Ask more questions.

That is one of the most common refrains in the feedback attorneys give summer associates.

Ask more questions.

Summer projects often include limited context. How does the assignment fit into the bigger picture of the case or matter? You might not know. The assigning attorney might not tell you.

This often means that, as you begin, work through, and prepare to turn in the assignment, questions arise. Lots of them.

So why do summer associates hesitate to ask questions?

Fear.

We fear looking less knowledgeable. We fear appearing like we couldn’t figure it out ourselves. We fear bothering the assigning attorney with what we deem to be silly questions (hint: most are not silly).

Acknowledge that fear and ask anyway.

• First, ask clarifying questions immediately upon receiving the assignment.

• Second, ask questions when you get stuck.

• Third, ask questions after you review your draft of the final work product and before you turn it in.

Note: This requires that you use your time wisely and build in buffers, allowing you to put the work product down for an hour or more (overnight is best) instead of procrastinating right up until the deadline.

It is better to ask “dumb” questions early, than smart questions too late. (Again, few of your questions will actually be dumb ones.)

Partners, senior associates, and other assigning attorneys would much rather spend 10-30 minutes answering questions upfront and before you turn in the final work product than fixing work that went off track. By engaging with the work—really taking ownership of it—and asking questions, you demonstrate investment, you dodge avoidable mistakes, and you show that you’re thinking critically.

What makes questions good questions?

Do your homework. Show you’ve tried to solve the problem and preface your question with what you’ve already considered.

Bundle your questions. If possible, group related questions to avoid peppering the assigning attorney with a constant stream of emails.

Note: Email is best for complex questions that benefit from written responses. But, if the assigning attorney allows it, instant messages, phone calls, and office drop-ins work for quick clarifications.

Be concise and specific. The more targeted your question, the easier it is to answer.

What types of questions should you ask?

Process Questions

• How deep should I go?

• How many hours should I spend on the task?

• Who will read the final work and why?

• What are your formatting and style preferences?

• When is the deadline?

• Is that an external or internal deadline?

• Is it a soft or firm deadline?

• How do you prefer I communicate with you about this project?

• What matter number should I bill my time to?

• Are there billing requirements for my time-entry narratives?

Matter Questions

• Where should I start my research? (Where would you start?)

• Who else on this team can I go to with questions?

• Who else can I talk to, to learn more about this case?

• What documents would be helpful for me to review for greater context?

During the Work Questions

• I’ve reviewed [INSERT MATERIAL HERE] and cannot locate [INSERT MISSING INFORMATION HERE]. Where else do you suggest I look?

• I’ve used the following search terms and am coming up short. How would you modify the search terms? What do you think I’m missing?

• I’m running up against your estimated time to conduct this research. Should I summarize the findings for you now, or may I have [INSERT AMOUNT OF MORE TIME HERE] more hours to continue working?

After Assigning Attorney Reviews Work

• What could I have done better?

• What should I do differently next time?

A note here: not every attorney will be open to questions, responsive, or offer time to meet to address questions. If that happens to you:

• Try a different communication method

• Ask a senior associate or other attorney on the file for guidance

• Create a paper trail that explains what you’ve done and why more guidance is needed

What do you do with the answers to your questions?

• First, document the guidance. Take notes and summarize the answers in a follow-up communication to confirm your understanding (and create a reference for yourself).

• Second, apply the answers to future assignments. Show that you’re learning. You want to avoid asking the same question repeatedly.

• Third, share your experience and knowledge. If you learn something broadly useful, share it with your summer-associate colleagues.

Many summer associates worry about appearing incompetent or bothering busy attorneys. The opposite, though, is usually true: assigning attorneys respect associates who ask thoughtful questions and are frustrated by those who struggle in silence.

And, law firms are collaborative environments—the law is one giant ongoing group project.

Asking questions saves time and resources, and builds trust and demonstrates initiative.

You don’t know what you don’t know and there’s not much you “should” know at this stage.

Asking questions leads to learning and growth—it is not a weakness.

So: ask more questions.

Thanks again to Emily for this awesome advice. Keep standing out.