Why You Should Take That Coffee Meeting

I’m busy.

There, I said it.

My days seem over-loaded. Sometimes I am literally panting while I go from meeting to meeting. I’m hustling to an extreme degree, and somehow the hours just keep getting shorter.

I have a feeling, though, that I’m not in the minority here.

Somehow we have all become busy beyond belief. We travel. We have side gigs. We are starting families, or caring for aging parents, or sometimes both. We are in night school. We’re taking on new hobbies. We generally are being total badasses.

Then we get an email in our inbox — “up for a coffee chat? I’d like to pick your brain.”

Lately, I’ve seen so many complaints from successful, interesting people. They get these messages from others asking to pick their brain, and they think to themselves, “why should I do this? Are they just looking for a freebie? Shouldn’t I be charging for my time?”

I get it. We’re all busy. Our time is worth money. We can’t just be giving our hard-earned lessons away for the price of a tall cappuccino. Right?

But something irks me about this kind of response. I feel incredibly indebted to the dozens (hundreds?) of people who have offered their time to me while I have grown my career. The four-time female founder who insisted on buying my coffee. The finance guru who offered a few insights as I sharpened my pitch deck. The businesswoman who interviewed me in a small restaurant off the highway when I was applying for Wellesley. Where would I be if they had asked me for money in exchange for their wisdom?

Though I’m certainly not perfect, I try to pay these moments forward by making myself available as often as I can for a coffee date. I realize I won’t always have the ability or the capacity, but being open to these spontaneous moments makes me richer in both tangible and intangible ways.

But even I forget sometimes how useful they can be.

The other day I caught myself questioning an upcoming meeting again. I had agreed to have coffee with a friend of a friend who wanted to talk a bit about Wanderful. I wasn’t sure why, or what I’d get out of it. I thought more than once about canceling — I was grossly behind on my deadlines and had a “to do” list that seemed to extend all the way out the door. But I had agreed to something and I guilted myself into sticking with a commitment.

It was easily one of the best meetings I’d had all week.

If you find yourself with an invitation on the calendar and are questioning if it’s worth it, take a moment to reflect on some of the below outcomes that may occur from saying yes to an hour of your time.

Ideal: This person has exactly what you need

Of course, the single-best outcome that can happen from a coffee meeting is that you find out that this person is equally useful to you as you are to them, whether you’re looking for funding, a new distributor, a realtor, or whatever else.

A quick look at their LinkedIn page may help you identify their areas of expertise — but if you don’t see anything, don’t be discouraged. I have on a number of occasions noticed that someone’s LinkedIn page doesn’t even begin to address the wealth of information they have on a topic that’s of significant interest to me.

More likely: This person is connected to someone who has exactly what you need

Okay, most likely this person isn’t going to be the gatekeeper to your next big win.

But that’s okay. Never underestimate second- or even third-degree connections. If you give some of your own hard-earned advice, you should be surprised if your coffee buddy doesn’t offer his or her help in return. Be ready to tell them about what you’re working on, in case they can connect you with someone in their network. Even if the person doesn’t work in your field of business, we all know people through family, friends, school, our kids, you name it.

Having a personal intro to the person you could use help from may be all the difference between actually getting that help and having that request fall into a “spam” filter.

If you’ve already looked at your future coffee buddy’s LinkedIn profile, don’t be afraid to check out who their connections are too. Though you definitely don’t want to be abrupt (“Let’s cut to the chase here: You know Susan and I want to meet with her” might not work on a new contact), you can use your goals to direct the conversation after you’ve offered your expertise.

This person is a potential customer or partner

I’ve lost count of how many times I’ve sat down with someone only to realize that they should be a member of Wanderful, or a hostess in our network, or a sponsor at the Women in Travel Summit, or any other form of collaborator in our community.

If someone has taken enough of an interest in you to invite you for a cup of coffee to pick your brain, they likely operate at least in some part in the space you’re in. Here’s a chance to invite them even more deeply into your world by building a working relationship.

This person is simply an interesting person and a new friend

Okay, I’ll admit it. It’s entirely possible that this person will not be much of any immediate help to you. I mean, you’re the one meeting with them anyway, right?

But what if you hit it off? What if this person ends up being a super fascinating, fun, kind person? What if you decide — gasp — that you might actually be friends?

One thing I hear possibly more than the complaint that we’re not charging for our coffee dates is the complaint that as adults it’s impossible to make friends. Well, here’s your chance. Here’s someone who you could invite to your Friendsgiving. Or to your New Years party. Or a double date with your partners. Or…get ready for it…for a follow-up cup of coffee.

You get an opportunity to practice your pitch, and to talk through your business model out loud to a listening ear.

Maybe this person has nothing to offer you, and no connections. Maybe this person isn’t really the type of friend you’re looking for, and maybe they’re not going to be a customer or partner anytime soon (or maybe they already are one).

Here’s what you will always get: an opportunity to test a new way to talk about your business. An opportunity to hone your story and your pitch with no risk. An opportunity to think through something out loud that you might not have thought through before. Use this as an opportunity for you to test your business on someone who is willing to listen to you and provide feedback. As a sole founder, being able to talk through my business out loud with another person is one of those cherished opportunities that I can always use more of.

You get to give back.

And finally, lest we forget the whole reason we’re meeting with someone in the first place: to help them out. To offer some advice. Let this be your chance to pay it forward for all of the other times inspiring people have sat down with you and shared their candid perspective. Let this be your opportunity to feel grateful that someone now sees you as this inspiring figure.

Embrace it. Breathe it in. Enjoy the moment of being the wise sage and not asking for help all the time. Recognize that we are all here to help each other as much as we can, and that you are doing your part.

And if none of that works, at least you got a nice cup of coffee, a few minutes away from starting at a screen, a few more steps logged in your FitBit, and some fresh air.

Life is about more than just logging the gives and takes.