By now, I've led countless initial calls with prospective portfolio companies, usually sticking to a tight pre-assigned 30 minutes, whether taking place online or in person. I've learned how to structure that half hour to make the absolute most of it. Near the close of a call last week, though, a founder asked me something I couldn't recall encountering before: "Where does your team struggle?"
I paused for a moment, gathered my thoughts, and reflecting on what we did in 2023 and what we've elected to bring with us into 2024, I answered the question with two distinct examples. After I finished, I asked if I'd sufficiently replied to the question. He said, "Yes, even more than I asked for. I only like to work with people who are willing to acknowledge they have weaknesses and areas to grow."
A palpable commonality, I've long maintained, resides at the intersection of the two halves - PR portfolio support and business development - of my active role. I must enter conversations with reporters and entrepreneurs alike, knowing well that the same five to eight questions that everyone else has posed before them will show up again with new contacts. And, based on experience, I am expected to arrive with considerable answers that don't seem or sound rehearsed.
What I've learned over the most recent chapter of my career is that the best PR people answer the questions - and they prepare their clients, too, to share more when others might have declined. There's usually a way to thread the needle, and to be more open, and the executives near and far who are admired most operate with both good judgment and striking transparency. As I prepare others to speak, I make sure to sip my prescribed medicine.
I recognize that I can make a strong first impression on the listener by coming with responses and solutions to the most common five to eight questions that will inevitably turn up. The first things are often the most critical things that pop to mind. I've also come to believe that I'll stand out more so from my peers with how I approach, tackle, and emphasize question number nine.
My evolution as a professional and my education in VC terminology is best spent these days on anticipating what I'm not being asked yet that I could be inquired of and solicited for at some point. Even if I may have to pause and then riff a bit in my reply to a question I haven't heard, I know that I'll be ready for that occasion, too.
