The Most Important Question You’ll Ever Ask in a First Meeting

So what’s your question?”

Two years ago, Michael Kislin, a financial adviser I had met at an event I had spoken at, met with me for the first time in my offices. I get solicited a lot for meetings with financial advisers and commercial real estate professionals, and so my guard is always up when they ask to meet with me. But Michael seemed like a nice enough guy and promised that he wouldn’t take more than fifteen minutes, that he had just one real question for me, and that he wouldn’t try to sell me anything. It seemed like an offer I couldn’t refuse.

Still, when it came time to meet and he sat down in front of me, I was nervous. Would he somehow try to sneakily sell me? What did he want from me? And what was this mysterious one question he wanted to ask me? We exchanged small talk, and he told me a little about his business. He was establishing a niche as a financial adviser to tech start-up entrepreneurs. Although many of his clients weren’t wealthy yet, his idea was to build relationships with them all now so that as some of them did succeed and amass wealth, he’d be there to help them (and make money, of course). Then the moment of truth came. I asked Michael what his one big question was, and he replied:

“How can I help you?”

Frankly, I wasn’t sure at first how he could help me. But then I had an idea. I told him about my latest start-up venture, Likeable Local, and said I could use some introductions to early-stage technology investors. He asked me a bunch of questions to learn more about the specifics of whom I was looking to reach. Then we wrapped up the conversation, and he said he’d be in touch, but only if it was with something that could be helpful. No sales pitch. No gimmicks. Michael just sincerely promised to follow up if and only if he could actually help me. And that he did. The next week, Michael introduced me via email to three different early-stage tech investors he thought I would want to meet. Although I didn’t end up taking investment money from any of those three individuals, I did genuinely feel very grateful to Michael. As a result, when I called to thank him, I asked him to tell me more about what he did. As he told me about his business, it dawned on me that I did have a need for a financial adviser. I soon became a client of Michael’s, and my wife and I have been working with him ever since. He didn’t try to sell me, he didn’t try to persuade me, and he didn’t try to trick me. The idea to hire him had not been his but mine. All because of one question.

My father-in-law, the Honorable Steven Fisher, always taught me to “show your friendship first.” What he meant by that is that you should show the other party you’re there to help him, that you care, before you even consider asking something of him in return. There’s no better way to show that you care about the person you’re meeting with than to genuinely, authentically ask her what you can do to help.

There are two possibilities for what can happen when you ask, “How can I help you?”:

  1. The person will tell you, giving you an opportunity to help, after which he will feel indebted to you, connected to you, and appreciative of you, and will eventually feel compelled to return the favor and help you one day.
  2. The person will decline politely, probably because she doesn’t know how you can help her, but will feel that you care and feel connected to you and be much more emotionally invested in helping you eventually, even if you never have to lift a finger for her.

Either way, by establishing that you care and that you’re there to help, you’ll gain trust and eventually influence. So, the most important question you’ll ever ask is: “How can I help you?”

If it seems simple, that’s because it is. It doesn’t matter whether it’s a customer, a prospect, or a colleague you’re meeting with: We all like to be cared about, and we all can use some help. Just make sure you’re genuine and never contrived or inauthentic when you ask, and of course be sure to follow through on anything you promise or commit to. Also, ideally, make sure the other person knows a little about you and your network, expertise, and sphere of influence so that when you ask him how you can help, you are fully equipped with the tools to provide any help he asks for. You also should do your research about the other party so that you know, going in, various ways you could help. One of the greatest ways to help people is to introduce them to other people (more on that later).

The best part about “How can I help you?” is the long-lasting effects of that one simple question. Case in point: Not only am I still a happy client of Michael Kislin’s, I appreciate his ability to show his friendship first so much that I’ve introduced him to several people who have become his clients. I hope that’s just the beginning of the ways I can help him.




Dave Kerpen is an entrepreneur, speaker and bestselling author.  He is the founder and CEO of Likeable Local, a social media software company, and the chairman and cofounder of Likeable Media, an award-winning content marketing firm for brands.  He is among the most popular writers in LinkedIn’s Influencer program, is one of the most read contributors for  You can visit him at  And you can purchase his terrific book “The Art of People” by clicking “HERE” .


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