Every day you have dozens of conversations, and each week a few of those are with people you don't catch up with on a regular basis. Believe it or not, one of those conversions can turn into a project.

From Bradley Jacobs, Mylance Founder and CEO

How this happened to me

I was in New York visiting family and working from a co-working space. It turns out, the co-working space was actually an early stage start-up that was turning restaurant spaces into working spaces during the day.

Given how small the company was, the Head of Operations of the company happened to be there, and sponsored a Happy Hour for the folks working there. I was curious about their business, so I went over to talk to him. We got to chatting about the company, how they'd originally tested their model, and I started asking questions about how they were thinking about expansion, launch, and scale. As I asked curious questions, I dove into areas where I'd become an expert at Uber.

As we talked, I asked questions and listened intently to his answers. As we went on, he started to have fewer thoughts about the deeper areas, and he eventually turned it around on me, asking me what I thought they could do. This was the perfect entry - I could answer his question, reference my Uber experience (I launched Miami and Milan for Uber Eats, and launched Uber Freight in the US), and help him think about how he'd scale the business efficiently.

Without an intention of selling myself, I gave him tangible thoughts for his business, I validated myself and my experience, and I teased a way I could help with their business.

As the conversation wound down, he gave me his card and told me to email him to set up time to talk to see if we could work something out.

How asking questions helps you scope out a project

Asking questions not only validated me as an expert, but it also helped me learn a ton about their business. I learned where they're doing well, where they're struggling, what they've tried thus far, their fundraising status, details about their team, etc. All of this information gave me detail into what a potential project could look like for us.

While you can find out information simply by asking them what their business goals are or what keeps them up at night, there are two specific tactics I've used repeatedly to get the client to elaborate further.

Mirror - mimic the last 1-3 words of the end of their sentence. They’ll likely explain further. 

Example:

• Client: “Our marketing department is really holding on by a thread.”
• You: “Holding on by a thread?”
• Client: “Yeah well, we lost Jenn to maternity leave, and haven't been able to find a great replacement. We need someone ASAP.”

Label - label what they’re saying by starting with “it seems like...” and they’ll likely elaborate if you’re right or if you’re slightly off, and you can hone in on what’s really going on.

Example: 

• Client: “We had to fire our head of marketing because he wasn’t getting the job done and now we’re struggling to calculate CAC”
• You: “Got it. It seems like you’re frustrated with tracking around your current marketing efforts.”
• Client: "That's right. It's been frustrating as we've been through 4 marketers in the last year, and we're not seeing the growth we need to hit our Series A target."

By doing this, your client is almost guaranteed to elaborate on their issue, which helps you dive further into their challenges, and thus where you can help them. Take great notes here, and try to write down as many of their words as possible. Use their words in your proposal -> it will resonate strongly with them.

Try these two techniques every day. Try them the next time you're catching up with your friend, partner or parent. You’ll see that the person you're talking to simply elaborates on their previous point, and you learn more. You can do this for hours!

You end up getting much much more information out of someone, and they feel great while they’re doing it because they feel totally heard by you! You're building an emotional connection with them just by asking curious questions. It may feel awkward at first. However, the other person won’t think twice about it.