Email etiquette for entrepreneurs: How to get busy people to care

This post originally appeared on the Crew blog.

The more time I spend working on my startup, the more time I seem to be spending in my inbox. Running a startup is pretty much synonymous with “sending lots of emails” I’ve realized (especially when you’re not the person writing lots of code).

The more emails I write, the more “rules” I come across for how to write them, too. Everyone seems to have their own specific ideas for best practices, but I’ve collected some of the more general trends in advice for various types of emails.

Asking for intros or favors

One thing email is used for is to ask each other for favors like introductions to potential employees, investors or customers. Here are some tips I’ve picked up for doing this:

1. Make the ask clear

Don’t be afraid to ask for what you want. Hiding your request in unrelated chatter won’t make the recipient less likely to say no, it’ll just make it harder for them to work out how they can help you (which could even make them more likely to say no). Iris Shoor from Takipi found this worked best in her experience:

When I started to cold email prospects I asked for feedback, thoughts or advice. It didn’t work. I found out that the more direct I am the more likely I am to get a meeting… When you’re seeking help, people are more likely to answer if they feel they can really help you.

What worked best for me was being very specific – scheduling a meeting for a specific week, asking to demo the product and if they’d like to install it on their servers.

The last time someone asked me to meet with them, they came right out and asked to meet with me to chat about work I’d done recently. There was no confusion on my part—I knew exactly what she wanted and simply needed to say yes or no. That’s how simple your ask should be.

2. Make your reasons clear

If you’re asking for a favor from someone who’s really busy or an intro to someone who’s constantly bombarded with requests, it can help to make your reason for requesting the favor clear.

This is where you can show off the research you’ve done (hopefully) and the fact that you’ve targeted your request at someone who you believe is a good fit, rather than sending out random intro requests which busy people probably won’t appreciate.

For instance, if you want an intro to someone who has lots of experience in marketing, explain that this is what you need help with. Or, if you have something in common with the person you’re trying to reach, such as being alumni of a school or organization, or if someone you respect has recommended them as a good person to talk to, make these reasons known so it’s clear you’re not going to waste their time if they agree to meet with you.

3. Make the request easy to follow up

If someone’s helping you out, you want to make it as easy for them as you can.

I’ve found that including a short paragraph about myself or my startup (depending on the nature of the request) that can easily be forwarded on saves the recipient the time and effort of explaining who I am and what I want when they set up the intro.

4. Check before doing an intro

This one makes complete sense to me now but never entered my mind when I first started making and asking for intros. If you make an intro before checking that both parties are keen, you can put them in a very awkward situation where one person may not have time, or simply isn’t interested in talking the intro, but you’ve already made the connection.

I’ve found you can develop much more trust by checking with both parties first and only making an intro if everyone is keen. I guess it’s a bit like the Tinder model, for email intros.

Following up

A tricky email to send is always the follow up after not getting a reply. It’s a fine line between following up politely and being annoying, so here are some tips for walking the line carefully.

1. Target your emails

To start with, target your emails carefully. You’ll have much more luck getting a response from someone who’s likely to be interested in the first place. You can do this easily enough with most journalists, investors and so on, since their interests are usually easy to find online.

From being on the receiving end of cold emails and follow ups, I’ve found that knowing why I was targeted makes me less likely to ignore an email since I can see that the sender has put the effort in to make sure I’m a good fit for what they’re after.

2. Add value

When you need to send a follow up email, it can be less intrusive if you add value each time.

For instance, you might point the recipient to another product or some news they might be interested in, or offer to help them with something. This means your email achieves its purpose—reminding them to respond—without being pushy or totally focused on you and your needs.

3. Know when to give up

This tip is a debatable one, because the best time to give up depends on who you talk to. Some will say you should never take no (or silence) for an answer, to the point of extremes in some cases. Others say if you don’t get a reply to a cold email after three or four days, move on.

Regardless of what you decide your rule of thumb is, if someone asks you to stop emailing them, that’s a clear pointer that you’d be overstepping the mark if you continued.

Reaching out to press

Trying to reach press can be one of the most tricky email situations for entrepreneurs. There’s no surefire way to get press about your company, but these tips might help get you closer.

1. Target leads

As I mentioned earlier, targeting your emails makes you more likely to get a reply. Crew co-founder Mikael’s written about this before, with some great advice based on his own experience. I really love this clever idea he wrote about:

Find leads through a competitor

One of the best ways to find targeted press leads for your industry is by searching for a competitor’s app URL and finding which journalists have written about them. Do this by:

• Going to http://www.alexa.com/
• Search the competitor’s app domain (i.e. fiftythree.com)
• Click “Sites Linking In”

2. Follow writers

A great tip I got from Buffer’s co-founder Leo is to get to know individual writers and journalists. This makes targeting your press outreach easier, because you already know writers who fit well with your product or business.

Mashable doesn’t cover you, a writer does! — Leo Widrich

Leo suggests following individual writers on social networks, keeping up with their work and engaging with them regularly. As you get to know writers individually, your name will become familiar to them so it’s less likely to get passed over in their inboxes—another benefit!

3. Say thanks

When you do get press coverage, don’t forget to follow up and say thanks. This could be as simple as a quick email or tweet saying thanks, or it could be following up with feedback about the coverage.

If you’ve found journalists who focus on your niche specifically, a great way to thank them for helping you is to keep them abreast of any new announcements about your company or news in your industry.

And of course don’t forget to read over your email before sending! Scott Britton has a great rule for checking if your email is ready to go:

Before you fire off a cold email, read it and ask yourself – would I want to have a conversation with a person who sent me this email? If the answer is no change it.

Email is very personal, and according to a lot of people, it’s broken and frustrating to use. Part of the problem with email comes from the fact that anyone who knows your address can fill up your inbox without your consent.

Above all, my advice as a sender of emails is to respect your recipient and try to offer them value in some way, in return for adding to their inbox count.

Read next: 3 Gmail tricks that can save you hours every week