Hi Andy + Emma — What’s a not-obnoxious way to keep in touch with a hiring manager after getting rejected?

I’ve been interviewing on and off for months. While I haven’t found the right fit yet, I have met some cool people in my field via various interview loops. I’d like to keep in touch with them (and maybe even get coffee one day??), but I worry my follow-ups sound like I’m asking to stay friends with an ex after getting dumped.

Is there a graceful way to approach this, or am I networking up the wrong tree?

Andy: I’m sorry that you’ve been interviewing off and on for months. That’s a grind — kudos to you for keeping sight of your goal. And for wanting to keep in touch with the interesting people you’ve met along the way! I wholeheartedly endorse this move.

Emma: Me too. I love your dating metaphor, but definitely wouldn’t compare these hiring managers to an ex who dumped you. I’d say it’s more along the lines of: Went on one date, didn’t feel the spark, and amicably parted ways.

…does that make asking to stay friends less awkward and vulnerable?

Andy: Maybe?

Emma: Putting yourself out there is putting yourself out there. It’s hard and brave, and there are exactly zero things wrong with sending a short, friendly email asking to grab a coffee.

I also clock your chances that they’ll say yes at about 22%.

Andy: It all depends on who you’re asking. Do they enjoy drinking coffee with a stranger? Do they have time? What’s in it for them? I know lots of people who would say: No, absolutely no, not much. I’m one of them. I might not even write back, but hey, that’s OK! It says more about me than whoever’s writing to me.

Emma: Totally. That’s what makes it such a non-obnoxious ask: It’s easy for someone who isn’t interested to do nothing. The graceful way to approach this is by simply asking, and not feeling rejected or diminished or resentful if there is no response.

Andy: You’re building your community of great people who you’d like to learn from and grow with. The people who belong in that network will write you back. So let’s get right down to it.

How to Write a “Let’s Get Coffee” Email to Someone You Met Only Once

There are five things that will make an email like this the most successful. It doesn’t matter if you’re writing to someone with more seniority than you, a direct peer, or even your junior. The same rules apply:

1. Short: Aim for casually straightforward and to the point — two brief paragraphs max. As intimidating as emails like this are to write, remember: This is not a big request. No need for long justifications or even mentioning how you didn’t get that job.

2. Specific + complimentary: You’ll be getting more out of this networking than they will, at least to start. Some authentic flattery is one way to balance the scale: you get to connect with a person you think is cool, and they get to feel good about themselves. We’ve talked about the qualities of a great compliment before. Now’s the time to put some of that into action.

3. Not too soon: This email is not a response to the “you didn’t get the job” email. Give yourself a month or six weeks to let that experience fully end before starting this new one. That will help keep it from seeming overly strategic — like you’re still gunning for the job, or expect them to help you get the next one.

4. Suggest a timeframe: Always propose a time, even if your schedule is wide open. It’s one of our rules for great emails. If your schedule is super tight, wait until it opens up a bit before trying to begin a networking relationship. It’s just good manners to be accommodating of the ask-ee’s schedule.

5. Email only once: You get to ask about once every 6+ months. Write a solid email and send it off. What they do with it is their choice.

Here are a few examples:

Start off with the ask:

Hi Andy,

Are you available for a coffee any day next week?

I was so impressed by my interview experience last month. I’ve been reflecting on how comfortable I felt talking through my past job experiences, and I think a lot of that came from your balance of interesting questions and candid commentary. I’m inspired!

I’d love to talk with you about how you approach interviewing.

Let me know,

Or, start with the compliments:

Hi Emma,

I really enjoyed talking with you at The Bent, especially how you challenged my thinking about the hiring programs I’ve put into place, and how my results lacked diversity. I’d never thought about it from that angle, and I’m glad I am now.

I’d love to learn more from you. Are you free to grab a drink at Rick’s on Main sometime, maybe this Friday?


This one isn’t specific, so it’s much less compelling:

Hi Andy,

It was great meeting you last month. I’d love to stay in touch. Are you free to grab a coffee next week?


Even one little specific makes it much more effective:

Hi Andy,

It was great meeting you last month — I’m still thinking about your metaphor of the octopus in the too-small aquarium. I’d love to stay in touch. Are you free to grab a coffee next week?


Emma: Good luck! I hope you get a few yes’s — which is making me think we should talk about how to prep for all the coffee-cum-informational interviews heading your way.

Andy: Next week!