In the days leading up to my first office hour as a Student Caseworker with the uOttawa Startup Law Clinic, I spent time reviewing the information and documents the startup founder had shared with the Clinic, researching the issues I thought might come up, and preparing questions to help guide the meeting. By the time I joined the Zoom call, I felt prepared, although admittedly still a little nervous.

There was one thing I could not prepare for in quite the same way: the conversation itself. I did not know exactly what the founder would ask or where their answers might lead.

Preparing a Map, Not a Route

I entered the meeting with prepared questions and an idea of how I might work through them, but I quickly found that the founder’s answers were shaping what made sense to ask next. I had to pivot, asking follow-up questions I had not prepared in advance and moving past questions that had already been answered through the course of the discussion.

My notes became reference points rather than a sequence I needed to follow. The research I had done beforehand still mattered, but in a different way than I had expected. It gave me a foundation to draw on as issues emerged, while the founder’s answers supplied context that I could not have anticipated beforehand.

By the end of the conversation, I understood my preparation less as a route I was supposed to follow and more as a map I could use to navigate a conversation I could not predict.

When More Information Is Not Necessarily Better

The office hour also highlighted an interesting contrast with the way I am accustomed to approaching problems in law school. In an academic setting, there is often an incentive to be comprehensive: spot another issue, consider another argument, add another qualification. There is value in demonstrating that you have considered a problem from every angle.

Speaking with a founder changed the objective. The challenge was to decide what was relevant to the question being asked and explain it clearly enough to be useful, rather than communicate everything that could possibly be said about a legal issue.

That balance was not always obvious. Sometimes more context was helpful; other times, adding every related consideration would only make the central point harder to see. I had to consider what the founder actually needed from the conversation alongside the accuracy of the information I was providing.

Deciding what would be useful also meant recognizing when I could not confidently answer a question on the spot. When that happened, saying, “I’ll look into that and follow up” allowed the conversation to keep moving while giving me the opportunity to research the issue properly afterward. I could then return to the question with a more considered response.

After the Office Hour

After the meeting, I prepared a written summary of what we had discussed, addressed the outstanding questions, and included links to relevant materials for further reference.

Preparing the follow-up gave me an opportunity to revisit the meeting at a different pace. During the conversation, my attention had been on listening closely and responding in real time. Sitting down with my notes afterward, I could look at the discussion as a whole and be more deliberate about what deserved emphasis. Some points warranted a closer look, while others seemed less important in hindsight.

Having that time also changed how I thought about the follow-up itself. It was more than a record of what had been said during the meeting. It was an opportunity to build on the conversation and leave the founder with a useful written resource they could refer back to afterward.

What I’ll Carry Into the Next Office Hour

My first office hour gave me the opportunity to see what preparation looks like once a real conversation begins. The questions I had prepared and the research I had done gave me a foundation, but drawing on that foundation in the moment required judgment in ways I could not fully anticipate beforehand.

Exercising that judgment is a skill I will continue developing through the Clinic. Going into my next office hour, I will prepare just as carefully, with a better sense of what it means to put that preparation into practice.