I think one of the common mistakes that entrepreneurs make in their first meeting with investors is that they talk too much. Entrepreneurs like to just give some sort of freeform description of their business that anticipates all potential questions, and is sort of like a closing argument in a trial. They speak for 15 or 20 minutes, maybe even with the assistance of PowerPoint slides, just talking and talking and talking, and the angel has zoned out or has missed something really important. I think this approach, though very common, is much less effective than a real conversation. I think an entrepreneur that listens and asks questions is going to create a more engaged experience. So after the first two minutes of describing what it is you do, pause for a moment and ask what the investors reaction to that two minute description is. I think a two-way conversation is much more engaging; it’s more likely to help me understand or help an investor understand what it is the company is doing. And many times the investor is going to be turned off within the first few minutes, not because you’re doing anything wrong, but it’s simply not a match. Your goal is to find an investor that’s a match and not convince someone to invest like a lawyer arguing a case. So find out soon in the time that you’re spending with an investor whether they’re interested in what you’re doing, and if they’re not take advantage of your remaining time together to get referrals to other investors that might be, or to get feedback on your pitch. And many times I’ve seen an entrepreneur do this, and then while the angel is giving feedback about the pitch suddenly they start to convince themselves that they’re interested in the entrepreneur’s pitch that they originally weren’t interested in at all. And to me, that underlies how much engagement makes a big difference. And so try to foster engagement. It will help you close a deal, but it could also help you get useful feedback and referrals to other investors.

The end of the meeting is an opportunity to really foster engagement. Ask the investor what the next steps should be. Do set up a clear timetable for following up with the angel. Then you have a template that you can follow and you can reference in further conversations. And if you ever perceive the ball not moving along the path that you all laid out at that meeting, you can honestly ask the angel why. And it’s an opportunity for the angel to either change the plan toward an investment or to say that they’re becoming less interested and maybe are no longer committed to a path toward investing. You don’t want to be so relentless in your pursuit of convincing the investor to invest that you drive them away and cause them to stop returning your phone calls or your emails. At the same time, you want to be persistent in maintaining engagement, and that’s a subtle balance to maintain. The best approach is to be open your communication and at all times refer back to the template of how you agreed you were going to follow up with the investor, and give them an opportunity to opt out. If they don’t opt out, it’s up to you to stay persistent until they have been so passive-aggressive in their lack of response that they’re basically communicating that they’re not interested. But often if you stay gentle and open in your engagement, and give the investor a clear off-ramp to disengage, they will stay engaged with you either moving toward a potential investment or remaining a resource for you as a referral to other investors or as an advisor to your company.