Following up: One simple key to your success

Bethany Crystal
4 min readSep 6, 2021


You’d be surprised how many people suck at following up.

When I was at Union Square Ventures, I probably got introduced to something like 500 people who I met in person, shared a brief connection with, passed on some advice or an introduction, and then never heard from again.

What’s frustrating about this is that at the end of nearly every conversation I have, I always explicitly ask, “Will you check back in a few weeks and let me know how it’s going? I’d really love to hear.” But for the vast majority of people out there, that one brief moment was the beginning and the end of our relationship. This is a major missed opportunity.

Over the same course of time, I can count on one hand the number of people who did the opposite — who checked in, who followed up, and stayed in touch. They have kept me apprised on their careers, keep me in the loop before major job transitions and in general seem interested in building a relationship in the long term. And despite having tens of thousands of people in my Gmail contacts list, it’s those half-dozen that, for me, rise to the top. They understand the value of connection, and the prize of following up.

Here’s the thing: Following up is never really about the initial problem. It may start there, of course, but it’s really your great opportunity to pivot the conversation and connection to the next level. It’s the best way to unlock your network and build an ad hoc advisory circle around you for years to come. The better you get at this, the easier it’ll be for you to “tap your network” when you need to down the road.

It’s in my personal best follow-ups (and I’m talking, over months or years) that I’ve had great things come out of them: Jobs, volunteer opportunities, invitations, connection. There are people I met in a one-off, and those who I fight to stay in touch with. It doesn’t need to happen often, but it does need to happen about once a year to some level in order for it to stay fresh.

This is an art, not a science, but here are some best practices I’ve tried to establish over the years after my first conversation with someone new who gave me advice.

  • The first follow-up: A thank you
    This is sadly becoming a bygone practice, but I’m still a little old school. I don’t think you have to thank every person for every meeting with you (particularly business meetings among peers). But I do think, if you’re the one who initiated and you’re the one who requested advice, it’s very appropriate to send a note the next day.
  • The second follow-up: 3–6 weeks later
    This is the one that really lands for me but the one so few people tend to do. Let’s be honest: We’re busy people and sometimes I forget someone I met last month — particularly if I was in any way feeling rushed or busy that day. But this allows just enough time to pass that you’re not annoying, but also guaranteeing that I’ll still have some memory of what we spoke about. This is also the easiest layup of a follow-up to do: Just tell me how things went with whatever we talked about. Did you have the conversation with your manager? Decide to go down a different path in your career? Did you meet with other VCs and accept a term sheet? Even if you didn’t take any advice I gave you, if you’re interested in staying connected, this is the surefire way to get that foot in the door.
  • The third follow-up: 4–6 months later
    After the one-two punch of the first two, you can start to ease up on your cadence of communications. I do think one additional touchbase a couple of months later is the best way to stay on someone’s radar at least throughout a single six-month period. (Therefore maximizing their odd that they will remember you when it counts.) For this one, you have a few options: Check in again about that thing you spoke about before (but only share meaningful updates here), or maybe spend 5–10 minutes seeing what they’ve been up to online during this time and try to offer them something in return. Maybe they launched a new business or took on a new role. Maybe you saw they moved to a new city and you just want to drop them a restaurant recommendation of a place you love. Doesn’t have to be anything major. But it does have to be impactful.

After this period — three touchpoints over six month, you’ve set yourself up for a long relationship ahead. (Assuming, of course that your emails are being received and responded to.) After this point, in another 6–12 months, for instance, you can likely invite that person out for coffee and they’ll say yes. You can ping them again to check in on something else. You can offer your help or network on a new project they are working on. All the great things you probably do already with any professional connections.

If this seems simple, it’s because it is. Just set reminders, stay in touch, and you’ll see the benefits pay off.

If this seems hard, it’s because it is. With a million different things flying around, who’s got the time and energy to put toward this type of thing?

I’ll tell you who — people who are serious about the trajectory of their careers and businesses. And that could be you, too.

Originally published at Dry Erase.



Bethany Crystal

A little bit web2, a little bit web3… Today’s projects: @Bolster & @Zeitgeist_xyz , board @CompSci_High ; ex @USV , @StackOverflow , alum of @Northwes