After working with people for several years, you generally know them: their motivations and frustrations, their family members and hobbies, their working styles and goals. This knowledge—this organic intimacy—allows you to work more effectively with your colleagues. The question is: do you need to wait several years to learn all of this information by osmosis, or is there a more efficient way to pull this knowledge forward and expedite the effectiveness of your working relationships? The answer is, yes—you can kick start this on day one, even—through thoughtful, open-ended questions.

During typical one-on-one sessions between attorneys, the focus is often entirely on the tasks at hand: the brief due tomorrow, the issues list for a transaction, and so on. While these tactical conversations are necessary (and certainly productive), they rarely leave time for broader issues, such as career development and relationship management. To build trust, attorneys should also be using one-on-ones once a month (or once a quarter) to demonstrate interest in the person’s career, not just the task at hand. Deeper questions also invite vulnerability, which in turn reinforces psychological safety. Below is a list of questions to consider.

Motivations and Interests

●      Why did you take this job? What motivates you to come into work every day?

●      What type of work gives you the most energy? What feels exhausting or tedious?

●      Which projects coming down our pipeline seem most appealing to you?

●      How do you spend your time outside of work?

Growth and Goals

●      What development areas are you currently working on? Are there specific skills you hope to build?

●      What do you hope to achieve? What will that achievement unlock for you?

●      If you left this job, what would the reason be?

Communication Style

●      When are you generally available?

●      How quickly will you typically respond to email? When should I follow up?

●      Do you prefer questions by email, phone, or in-person? Do you like when people “pop in?”

●      What does “EOD”/”COB” mean? (e.g., 5pm, 8am next business day, etc.)

●      Will we conduct feedback sessions? How often? Do you expect two-way feedback?

Our Relationship

●      What does it look like when you are under stress? How can others help?

●      Think about your best team members or bosses. What made them stand out?

●      What are some things I may not know about you?

●      What drives you crazy? Pet peeves?