How to Perfect the Coffee Meeting

By Rebecca Lovell, originally published on The Riveter

With all the incredible assets we have in Seattle, I’d like to think the secret sauce of the local startup scene is coffee: not just because we’re so highly caffeinated, but because the city is filled with mentors who will have a cup of coffee with you as you pursue your passion. There’s an art to the coffee meeting — whether it’s a literal or metaphorical latte — and done well, it can be the beginning of a meaningful connection that can truly benefit both people involved.

In the last 15 years, I’ve partaken in hundreds of such meetings where the intent is to seek or provide support (or both). And not just because as a Seattle native it’s in my DNA to love coffee, but because the desire to do the most good for the most people drives my career. I always WANT to say yes when someone suggests coffee. That said, I’ve experienced the tension of truly wanting to help, while often worrying that I’ll underdeliver (do I have the ability to do what’s asked of me? And if so, how can I carve out the time to do it?)

That tension is a real issue for women in the workplace. Particularly in male-dominated industries (aka, every place I’ve worked for the last 25 years), women pay a “tax.” We are expected to mentor others — to be the coaches, the connectors — above and beyond all the responsibilities we share with our male counterparts. We do it because we WANT to help, and we know that representation matters.  So how can you balance that tension and advocate for yourself?

I’d love to provide perspective from both angles — mentee and mentor — and make an exception in sharing some do’s and don’ts. As a mentor, my mantra is I won’t tell you how to live your life, so let’s just call them “lessons learned.”

In 2005, my hero Phyllis Campbell came to guest speak in my class (she was leading the Seattle Foundation at the time, and I was convinced that was the career path I wanted to pursue).  After class I waltzed up to her and said “Ms. Campbell, I really enjoyed your talk, and if you’ve got 20 minutes, I’d love to buy you a cup of coffee and get your advice on the development role within nonprofit organizations.”  She responded: “call me Phyllis, and you’re a student so you don’t have any money — let me buy the coffee.”  Fourteen years later, I still consider her a mentor. I can tell you most of the reason she said yes is because she is truly a delightful and generous person. But now that I’ve been on the receiving end of hundreds of asks for coffee, thankfully there are a few things I did that made it easier for her to say yes.

How to ask a mentor for advice

1. Ask her for advice, not help. Asking for help I would reserve for say, if I’d fallen down a well and were desperate for assistance. Asking for help can engender pity, and that’s not the foundation of the kind of relationship I wanted to develop. Asking for advice, rather, acknowledges the mentor’s expertise (it also feels good to be considered an expert!)

2. Put guardrails around the ask: 20 minutes (so it’s time-bound), specific (the development role), and set expectations for the meeting (transparent agenda). In my heart, I wanted to say, “Phyllis you’re my hero, would you be my mentor?” but that likely wouldn’t have gone the way I wanted. Without relationship context, when I’ve been approached with the ask “be my mentor,” I find it paralyzing and intimidating — I don’t know what they expect, I’m not sure if I have the expertise or time.

3. Do your homework: Research your coffee date’s profile (thanks, LinkedIn!), tailor your questions to their expertise, and get a sense of their relationships in the community. Informational interviews and coffee meetings often lead to introductions — and don’t be afraid to ask who else they think you should meet.

How to be a good mentor

Shifting gears to the mentor perspective, I have a deeply-rooted philosophy that we should not *tell* others what to do, and that is for at least three reasons.:

1. Having agency in your own life and ownership of your decisions is critical to your well-being and success.  

2. You have the answers within, and a mentor’s role is to be diligent in unlocking them. 

3. Good entrepreneurs seek advice and input from the market. Great entrepreneurs know what advice to ignore.  

 Therefore….

Don’t tell people what to do (like I’m doing now), but ask questions.

Share a *relevant* story where appropriate — they’ll draw their own conclusions, and depending on the story, it can make you more relatable, vulnerable, accessible, and pave the way for more authentic conversations.

Get to know the person well enough to determine if you can make a recommendation or just a referral.  Either may help, but a vouch carries much more weight than a simple introduction.

Beyond the coffee meeting:

1. The double opt-in: Treat your network like gold. If you offer to make an introduction, ensure that both parties agree before connecting them.

2. The forwardable:  Before you reach out to your contact, ask your “mentee” for a 2-3 sentence email you can forward to the desired contact seeking permission to connect.  Not only does that lighten the load, it’s a strong signal of your mentee’s willingness and ability to follow through. If they don’t follow-up on this ask, who’s to say they’ll follow up with your contact?

3. Time-blocking: Though I’m far from fully committed to this discipline, I have found operational efficiencies in picking a consistent half-day per week for coffee meetings, and stay in one place, office-hours style, to reduce/eliminate travel time.  In managing my time, I block out as much time for prep and follow-up as I do for the actual meeting (2 hours of coffee meetings per week translates to 4 hours total).

Having had the incredible opportunity to meet with hundreds of entrepreneurs over the years, active listening (on both sides of the table) is the key ingredient, much more so than caffeine.  Serving as a mentor has absolutely helped me grow; answering probing questions has been a great forcing function for me to process my own experiences. So drink up! We can learn a lot from each other!