7 Ways To Get Any Boss To Respond To Your Emails

Writing emails to big, successful people can be pretty intimidating.

What should I put on the subject line? When should I email him/her? Should I sound professional or should I play it cool?

These are all questions I take very seriously in my line of business (email marketing), because what you say and what you do matters. The moment you hit send, that’s it. There’s no going back.

With that said, let’s go over the best techniques to get the big bosses, the CEOs, the VIPs, and the high & mighties, to read your email AND respond back. It’ll take you some time to warm up and get into the groove of writing to important people, but once you get these big guys to reply, you can get anyone to as well.

Let’s start with the first.

1. Find out when they’re online

You can craft the PERFECT message, but if you send it at the wrong time (the time they’re sleeping, the time they receive mass bulks of email, the time they’re away), they might not even see it. Let alone, not bother to scroll to the bottom of the inbox because they’re just so…busy.

Now studies show that the best days to email people are Tuesdays to Thursdays. Time-wise, at 9–10am and from 12–2pm. This makes sense, because work pace slows down and that gives people more time to check their phones and messages.

Yet, everyone has their own schedule. So why follow the general rules for sending emails at a specific time frame when you’ll have more success if you know exactly when they’re active online? Do some research — record what time and day they respond to blog comments, tweet on Twitter, reply on Facebook posts. You’ll start to see a pattern of when they’re most active. And those are the best times you should send an email.

Note: avoid sending emails on Mondays (that’s when people’s inboxes are the fullest because of the weekend email accumulation).

2. Make it about them

The world revolves around me. Me, me, me. My favorite person: Me.
I don’t want email from you. I don’t want junk mail from you. I want me-mail.

Seth Godin

Everyone is still a kid at heart — we all want attention. We all want to feel special. If you want people to respond back to you, do yourself a favor and make the email 80% about them. Compliment them on their work, achievements, awards, skills, even their looks if that’s what works better. Use your best judgment. How to fine-tune that skill is to dig deep into their profile and find out their biggest passions and what’s most important to them. I suggest checking their “about” page, social media, and any personal blogs they’re writing on.

It helps too if you say their name. Because when you mention their name, it immediately catches their attention and anything you say after that will triple its effect. Compliments and offering something valuable would work best in this case.

3. Be human, forget traditional business manners

Remember what school taught us? How to communicate proper English — things like how to address business people (Dear Mr. Holmes) or using “professional” words to express your thoughts (I will call your office in a few days to inquire about the possibility of a meeting).

Scrape all that. What has worked decades ago can’t with today’s bright entrepreneurs. After all, a lot of them don’t even have college degrees. People like:

Arash Ferdowsi, co-founder of Dropbox.

Mark Zuckerberg, CEO of Facebook.

Daniel Ek, co-founder of Spotify

Bill Gates, CEO of Microsoft

Steve Jobs, co-founder of Apple

So why talk big when these guys are bigger? Be yourself. Personalize your email to the way you normally talk to your friends. They’ll notice immediately and will actually respect you for being who you are.

My golden tip: If what you say can apply to anyone, change it.

4. Cut to the point

CEOs, founders, entrepreneurs, business owners all have a busy life, which makes them value time a lot more than the average Joe. And because they have to deal with 10x more emails, they must filter what they need to read.

Mike Gould, a former Colorado State University faculty member who’s one of the authors of the research paper for better writing, said “When you’re talking about a business audience, people have 10 to 15 seconds to read a one-page letter.” In other words, every word you say matters and usually, your first line (which I’ll describe more later) determines whether they continue to read or end up trashing it. To avoid the worst, I’d suggest writing your whole message out first, then cutting down words you don’t need.

Extra Tips:
Use short sentences — a good length would be 5–15 words per sentence.

Break into short paragraphs — no one likes reading bulk essay-like paragraphs. It’s overwhelming. 2–5 sentences in a paragraph is ideal.

Shorten your subject line — aim for 6 to 10 words, as this generates a 21% open rate based on ShowMeLeads research. And, keep your subject line all in lower case letters — it’s casual and catchy, or let’s just say ‘clickable.’

5. Keep your words simple

Important people hate it when they read big words. It’s not because they have to cut time away from their work to google it (which they probably won’t have time for), but mostly because it makes you sound like a egotistic know-it-all. Remember, your goal is to get them to read your message, not make them feel like a 3rd grader struggling in literature class.

Keep it simple.

Don’t do: Your profile galvanized me, and I’d greatly anticipate the opportunity to interview you.

Do: I felt super inspired after reading your profile and wanted to see if I could interview you for my blog.”

6. Offer them something valuable

When I say offer, I don’t mean selling your products or services right off the bat. You’ll get marked as spam. Warm up to them first, then tell them you have something they might like, not something they might want. See the difference?

Eliminate all sounds of sale pitches:

  • Being overly enthusiastic
  • Starting out with infomercial talk (ex. have you been getting enough sleep? I think I have the perfect solution for you!)
  • Engaging with generic replies (ex. let me know if I can be of help to you)

Be genuine. Describe what you’re doing and how you can help them. Don’t ask anything back. You can always save that in the next email.

If you can’t think of non-salesy reasons, just say you’re giving them “x” out of admiration or because they’ve given you something — inspiration, new knowledge, experience of trying their product/service, etc.

7. Pay attention to these 3 points in your email

Subject line: the “eye catcher”

You have about 3–4 seconds to grab your readers’ attention and interest them enough to open and read your email. That said, you should spend more time thinking about what to put on your subject line than just the email content itself.

Check Miranda Paquet’s email subject lines examples for starters.

Should I make it creative or cut straight to the point?

To be honest, do a bit of both. You want it interesting enough for the reader to open your email, but at the same time, you want to make it clear what your email is all about.

For creative email subject lines, I recommend looking at Hubspot’s selected examples.

And if you look at Mailchimp’s email experiments, the more straightforward subject lines got higher open rates than the creative ones. Here’s one of the A/B test results they got:

Happy Holidays from [COMPANYNAME]: 60–87% open rates
[COMPANYNAME] Moves You Home for the Holidays: 1–14% open rates

First line: the “first impression”

Once you’ve gotten pass the first challenge (people opening your email), you need to follow through and spike up their interest. At the same time, you want to introduce who you are and why you’re reaching out to them.

So instead of the typical, “Hi, my name is…” try these good email opening lines.

Last line: the “gift wrap”

Last impression is just as important as the first. You want them to remember who you are. Crack a joke. Make a comment on current news.

If you want to ensure a response back, don’t close the conversation by saying, “thanks for your time reading this.” End it with an open-ended question, like “what do you think?” They will put them on the spot and naturally they’ll respond, otherwise they’d get that uncomfortable feeling of ignoring someone. this is going to be the last thing they remember (keep it powerful)

A Quick Fix For Bad Emails

You screwed up. Don’t panic — it’s not the end of the world. You can always start over by using an email alias.


Mastering the skill of talking to the big bosses does not come overnight. Keep practicing these email techniques, and you’ll get anyone to respond back without a doubt.

This article was written by Tiffany Sun, blogger at rabbut.com.


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Rabbut is all about automating and optimizing emails based on people’s habits. To know the latest tips & tricks on how you can be a better email sender, visit our blog.