That’s why you can’t go wrong by asking a question. Then another. one left.

Recently, I was at the University of San Diego early to give a talk and walked into a networking event for the Knauss School of Business. I see more than 200 young men and women working in the room trying to decide what to do with the rest of their lives — or, where they’ll get their first job.

There are recruiters from large national companies looking to cater to this group. I met a young man from one of the top five consulting firms. We chatted – it turns out he might be a good fit for one of my companies – I asked him for his business card and he said he didn’t have one. Hey man, it’s a social event. I give him mine.

Rule number 2 says in my book “Baby I’m By Your Side”, “Networking is a profession. Be a pro at it.” This is baseline stuff. LinkedIn, shminkedIn, Facebooked, Instagramed, Tiktokked, airdrops — come on, even cavemen have business value.

This brings me to the next step, learning how to start and maintain a conversation. For this, I turned to Harvard assistant professor Alison Wood Brooks, who published a paper, “It’s Okay to Ask.”

People who ask questions, especially follow-up questions, “may be a better manager, get a better job, or even win a second date,” she said. The idea of ​​a follow-up question is powerful because it shows you’re engaging, You’re listening, you care (or you’re pretending you care), and more importantly, it clarifies what you’re talking about.

I always get the sales pitch. After I’ve listened, my pattern is to try and say to the host, “Let me make sure I understand. I think you’re saying…” This gives me the opportunity to ask follow-up questions to expand the conversation.

Brooks analyzed 368 sample transcripts containing six different types of questions, with 44 percent of the questions being follow-up questions. This is the most effective default option when trying to participate.

But you can’t throw it to another person without thinking, like your 4-year-old asking why the sky is blue, and then, why, why.

Stanford University did a study on speed dating and it showed that “if the participant asks one more question, he or she will successfully get a yes answer, I want to see you again.” I won’t touch on the third of agree track, but asking questions seems to lead to a higher likelihood of a positive outcome.

Good managers ask follow-up questions, and when they don’t – unfortunately because they don’t care what you have to say. You show disinterest when you just wave your arm and disconnect the conversation. You need to return the ball to stay in the game.

CEOs can explore deeper, more nuanced skills, specifically asking questions you already know the answers to. In this case, you’re looking for a way to make and deliver the answer back. You are looking for the level of emotional intelligence. You’re not asking math questions, you’re trying to gauge the comfort of the conversation.

When I was trying to hire a VP of business development, I was looking for a range of skills, one of which was being able to talk to potential clients and create a sense of comfort. This is a rapport issue, not a per-user pricing software issue.

Most importantly, in any conversation, you need to give back, and you need to provide answers, even to questions that weren’t directly asked. It’s a give-and-take game (which might be a good song title.) Brooks says you can train yourself to ask “leading questions,” which make it easier to follow up.

If you ask the right questions, miracles can happen. I was riding a ski lift with a buddy once, and when we got to the top, he had agreed to invest $200,000 in my first startup. It was sold for a good profit and he was happy.

Two follow ups and I headed to Black Diamond.

Rule No. 736: You don’t say it. Tell me tomorrow.

Senturia is a serial entrepreneur investing in early stage technology companies. Please email ideas to

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