You walk into the coffee shop with a pop in your step. This is the meeting you’ve been waiting for all week. The guy whose blogs you’ve been reading for months, who you’ve tried to get three separate intros to, who finally took one and agreed to get coffee with you.
You click instantly, you sit down, your sentences falling into the others at such a pace that you don’t even have time to jot down a single word in your notebook. You’re completing each other’s thoughts, you’re sharing the same world views, you’re swapping stories of people you both know. And then, with total nonchalance, he pops the question: “So, how can I be helpful?” And you wonder what it possibly was in that coffee that’s causing this giant lump in your throat.
Asking for something of value, especially of those whose accomplishments and time we respect the most, is a very difficult thing for most of us to do. There’s a natural selfishness in the act that arouses every bit of the shyness that you thought you’d overcome. Who am I to request a favor of you, we wonder. Isn’t it enough that you’ve given me the past hour of your time? How can I be greedy enough to want more?
But here’s the truth: the person on the other end of the conversation likely took the meeting because they believed you’d be someone they’d like to get to know. They may have appreciated what you’re working on or who you knew in common. They very likely had a number of people who helped them become successful, and in you they might see an earlier version of themselves. So don’t be shy – you’re there for a very good reason, and now’s the time to make the most of the opportunity.
Four thoughts that will help you nail the ask:
1. Do your research: Even before you initially reach out to this person, you should be familiar with who they are and how they could be helpful to you. What’s their current role and primary occupation? Where were they before? What sorts of career shifts have they taken and what might that say about them? What networks do you share? What have they recently blogged about/tweeted/said in public appearances?
All of these points come together in some form of a story (though be careful not to create your own narrative on someone else’s career), and being able to casually make the point that you respect your subject enough to have done your homework on them goes an exceptionally long way in impressing them. After all, any of us who make such information public – our LinkedIn profile, our tweets, our blog – expect that someone doing the work to reach out to us will have taken five minutes to look at them.
Keep in mind that their previous meeting could’ve been with someone who did a ton of homework and came extraordinarily well-prepared, and if you haven’t, you can guess which of the two follow-up emails they’ll put more effort into.
2. Know what you’re asking for: In business, help can pretty much be defined within three categories:
a. Advice: on product, on strategy, on recruiting, on management, etc.
b. Money: usually just investment or sales.
c. Introductions: usually to other people who could provide one of the above.
3. Be shameless but be realistic: There are two failure scenarios at the end of a successful meeting (one way to measure it is by how hard either party is trying to wrap it up – if your subject is delaying their next one to wrap up yours or running beyond your budgeted time, you’re in great shape). One is having an ask that is so broad that they have no idea how to actually help you, and the other is stumbling your way through the ask that it’s clear you lack the confidence to act upon whatever they might offer (not having an ask at all = you’re a rookie). If you’re an entrepreneur, you probably have a number of areas where you could use help. Narrow down your list to the five where you need the most help, and overlay that with the five where you think they’d be able to offer the most help. Across those sets of five, you’ll likely find a couple of areas of overlap. Go into the meeting with one primary area where you have a couple of concrete action items for them: intros to people that you know they know, an investment, or product feedback on an area that you know they’re good at. And then have a couple of other areas that you could mention and see whether they pounce. If you think you’ll be too hesitant or shy to make the ask, keep it simple and practice it a couple of times. And don’t ask for something too audacious – taking a junior manager at Salesforce out for coffee doesn’t make it likely that they’ll introduce you to Marc Benioff.
4. Be gracious and return the favor: While you may think of yourself as a lowly entrepreneur who couldn’t possibly be helpful to someone like who you’re talking to, you probably have a number of potential introductions to offer them. If they’re an investor, you could introduce them to amazing entrepreneurs you know, a great Meetup to check out, or the incredibly helpful app you just found. You might know of a good workspace or class or even a coffeeshop or wine bar they might like. You can always send them an interesting article that you recently read that speaks to some part of your conversation. As you build your network, you’ll find that some of the people you know might be ones you can introduce them to as well. At the very least, the follow-up email, the LinkedIn connection, and the Twitter follow (and occasional retweet?) go a long way, especially when done with genuine respect and in good faith. After all, you should be looking to build a long-term professional relationship with your subject, and not just looking for a quick connection to someone else. That may not materialize – we’re all busy – but the intent counts for a lot.
If you keep the thoughts above in mind, you’ll ace your next ask, and you’ll soon be hearing people’s asks more often than you’re delivering them!