Startup Curious
Startup Curious Podcast
Should I send a second email?
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Should I send a second email?

Welcome back to Startup Curious, where we discuss things you should know if you’re thinking about working for or starting a startup.

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Today I want to discuss the importance of following up, and how to do it well. Whether you’re waiting to hear back from a recruiter, potential customer or your boss, it can be a little nerve wracking to send a second message if they haven’t replied to your first. You don’t want to be a nuisance! And it’s easy to get carried away and assume the other person isn’t replying to you because they aren’t interested in what you have to say, or they secretly hate you or… any other number of things.

The truth is - people are busy. A lot of the time when they don’t respond to you, it’s not because they’re purposefully avoiding you. It’s often because your message slipped through the cracks. Maybe they forgot to hit send on a draft, maybe they read your message but forgot to mark it as unread again so they would remember to reply, maybe they told themselves they’d reply tomorrow and then never got the chance… everyone deals with so much communication, on so many different channels, it’s only natural that things will get lost in the shuffle.

However, following up can really pay off! When it comes to cold outreach, it can take a few messages before someone responds and turns into a customer. When it comes to dealing with recruiters, it can save you a bunch of anxiety waiting to find out if you got the job. When it comes to bosses and co-workers, it can unblock you faster.

So, the general advice I have for you here is: always follow up at least once… but put a little thought into it.

First, give the person a reasonable amount of time to reply. This is pretty dependent on the situation, but for non-urgent issues, then giving 3-4 days is reasonable. If there’s any timing considerations, like deadlines, then that should be taken into account. 

There are very few cases where it’s appropriate to send a follow-up in the same business day. Exceptions would be if someone has promised you a response by end of day, or if there’s some kind of high stakes issue being discussed where time is of the essence. 

When you’re doing cold outreach, you should likely give even more time - maybe even a week or two. Following up too quickly with a stranger can be perceived as spammy and leave you more likely to be blocked or reported as spam.

Also, when following up, make sure you’re polite! It can be frustrating to not get a response, especially if not having the response is keeping you from getting something done. However, remember that everyone is busy and just because something is a high priority to you, doesn’t mean it is to them.

Finally, consider if there’s additional information you can include in your follow-up that may be helpful. For instance, if you’re waiting to hear back from a recruiter and you’ve gotten an offer from another company - let them know that so they can re-prioritze their reply. If you’re doing cold outreach, maybe include some information about your company that you didn’t have in the first message to help the potential customer decide if you’re a good fit for them. Now, for internal matters with co-workers and bosses this is often less necessary - a quick “Hey, just wanted to check on the status of this, thanks!” may be all you need.

One other thing to note when it comes to internal follow-ups: pay attention to your company’s culture here. If you notice that email tends to go unanswered, but people are more responsive on Slack, then get used to Slack. If people tend to send one email and then walk over to people’s desks if they don’t get a response in a few hours… it’s usually okay to do that too. And as you start to get to know the individuals you work with, pay attention to what each of their preferences are here and adjust accordingly. It’ll pay off!

Okay, we’ll wrap up there for today. Now, if you have any follow-ups to do… block some time on your calendar to get them done!

Thank you for joining us today! If you found this episode useful, please remember to subscribe and share. Our goal is to make startups more approachable for everyone and the only way we can do that is to get the word out!

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If you have a topic you’d like to learn more about, or you’re a founder who would like their story featured on this show, send me an email at v@thescrappyoperator.com.

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Startup Curious
Startup Curious Podcast
What you should know if you're interested in starting or working at a startup.