I recently had a "coffee meeting" with a global leader in my field. It had been booked almost three months earlier and had me (happily) taking a car, plane, train, and jitney each way to meet her. We hadn't explicitly set an agenda or defined the purpose of our chat—but all the effort to make it happen was well worth it.
The truth is that these informal meetings can sometimes prove the most consequential of your career. But it's easy to be deceived by the casualness of an invitation to grab a coffee and imagine these opportunities are less important than they can be. They aren't actually job interviews or pitch meetings, but they're more intentional than chance conversations at networking events.
And that makes them hard to navigate. To find out how to do it, I spoke to four pros in the art of the coffee meeting: a super fundraiser for a global endowment; a top salesperson in the tech sector; a political powerhouse, and the head of business development for an international consultancy. Each agreed to share their tips with me as long as I don't identify them or their brands.
Here's what they advised.
Meeting experts recommend creating a hard agenda with stated desired outcomes. But that's not the best approach when it comes to the casual coffee meeting.
"The challenge that many people have is that they struggle to balance the opportunity that the meeting represents with the ostensible 'social' facade," says Super Fundraiser. "You need to clearly articulate to yourself what you want to achieve, but if you lead with that, the risk is that you will come off as pushy. It's key to put in the bonding small-talk time before coming to the 'ask' in meetings like this."
Instead, she advises "writing out how you would like this meeting to unfold and why—clarity and focus is key." But then, "Take it slow. As busy as this person is, they have agreed to meet you and given you this slot of time. Take confidence from that, and focus on building the relationship before worrying about your ask or next steps."
Studies show that employers and managers hire people they feel a "spark" or connection with; competence and qualifications alone are seldom the decisive factor. And it's no surprise why: We simply prefer working with people we actually like.
So how do you give a subtle boost to your likability during a first-time, casual meeting?
"You have to find some point of personal connection," insists the Tech Sales Star. "If you do enough research, there has to be something to build on. Read what they've written, ask around in your network, and, ideally, try to find a non-professional similarity. This could be a passion project, a charitable organization you are both involved with, or even an activity that both your kids do."
"Be subtle in how you work this in," he cautions. "The key to successful relationship building is to make it feel natural and unforced. Like you are genuinely making a friend."
Just like in an interview or team meeting, asking a thoughtful question can help you stand out, even if your query isn't geared to any previously established meeting goals.
"A strategically powerful question is one that both showcases your research and understanding but also indicates some insight into their analytical frame," says the Political Powerhouse. "Don't be afraid to affably ask questions that challenge an assumption. I often agree with the outcome but ask about the 'why' behind it."
Her two key recommendations:
- Ask "open-ended questions that direct the flow of the conversation to how you might be able to add value."
- "Be prepared to answer the question yourself, given what you know or understand of the situation."
P.T. Barnum famously advised, "Always leave them wanting more." And research from Harvard Business Review bears that out. It turns out that knowing when to end a meeting directly impacts sales and revenue generation—trying to oversell it leads to diminishing returns.
"No matter how well the conversation is going," the International Business Development Leader tells me, "I deliberately end the meeting when they are interested but still have questions or ideas they want to explore. This increases the odds of picking up the conversation in a second call or meeting, which both tightens the relationship and usually leads to bigger decisions being made in my favor."
To wrap up a conversation gracefully and leave on a high note, try this:
- Book a second meeting right after your coffee meeting so you genuinely have to leave, eliminating the risk or temptation to stay longer than planned.
- Practice your exit lines, so you can leave confidently.
All four of the experts I spoke to agreed that an effective follow-up within the next day or two was essential to advancing the relationship.
"Maybe it's my legal background, but always nicely get whatever it is in writing!" recommends the Tech Sales Star. "The email should reiterate any commitments or suggested next steps, and [it] makes sure everyone is on the same page." But keep the tone friendly and conversational, he says—just the way the meeting started.
I would add, based on my own experience, that it's okay to be excited to meet someone you professionally admire and to let that show. Obviously, don't be gushy or creepy about it, but a little well-placed enthusiasm is always more appealing than bland professionalism. After all, that's why you're "just grabbing a coffee" and not "setting up a meeting," right?