The UX of emails — how to write emails for high level executives

office email

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NOTE: if you are a long time CEO or executive, you already know everything in this post. If you are not, read on.

In 2013, I worked with How to Web, as program manager for their startup program: Startup Spotlight.

It was a deal making program, 2-day bootcamp and pitching competition for startups from Central and Eastern Europe. We would select 32 startups and facilitate meetings between them and 60 to 90 mentors. The mentors were high level executives or entrepreneurs. All the meetings were tailored for them to help them meet partners and hopefully end in deals to accelerate their growth.

I joined to help on the operational and the content side. I was the guy who had to “do the things”. I was keen on getting shit done, be as efficient as possible and make sure we get the project done on specs and on time. I expected to be evaluated based on how specific the implementation is.

Much to my surprise, the CEO at the time (Bogdan) was extremely specific about the emails I sent to potential mentors and guests. He had the harshest things to say about how bad my emails were and we spent the longest time improving them.

This was the top priority!

My emails were gold, it had all the details and was extremely specific.

Just check out this example.

Subject: “Invitation to Startup Spotlight”

Email Body:

Hello Mr. X,

My name is George, and I am the program manager for Startup Spotlight. Startup Spotlight is a startup bootcamp and competition… program description here.

Here you will be meeting 32 startups from CEE that have been selected… startup details here.

The program will be in Bucharest during 20–21st of November during the How to Web conference which… conference details here.

We will cover the transportation and accommodation cost… insert logistic details here.

We would love to have you over as a mentor. Please confirm if you are available.

All the best,
George Dita

[contact details here]

My email was polite, and had all the necessary details to make a decision: location, time, logistics, content, etc. And it was all in one place. But no, the CEO wanted me to write them the most “impolite” emails ever. They looked like this:

Subject: “Invitation to Startup Spotlight 21st of November
Email body:

Hi HugeCompanyCEO,

It would be our pleasure to have you as a mentor for Startup Spotlight (insert program link here) on the 20–21st of November in Bucharest.
During the mentoring you will be meeting part of the finalist teams for Startup Spotlight in 20 minute sessions. The sessions are at [location] in each of the two days between 6pm and 8pm.

We would love to have you, we await your reply.

Thank you,

Of course I am being sarcastic. My email was missing the most important things. The response from HugeCompanyCEO was “Sure!”. The response from Mr X… never came. The email was bad!

Why was that?

Because emails have an UX of their own, depending on who you are writing to. And writing to a CEO or a high level executive it is really different than writing to someone in an operational position.

I wrote that email for someone like myself. Someone that needs all the details to be able to implement. They do not care about that, they do not care about who I am, they care about what I can do for them and what I am offering.

Find out how to best give this information below.

The basics

1. Put everything in the subject line

They get at least 20–50 emails per day, excluding spam. They will only open those that have a clear call to action and are of interest. Get all the essential information in the title, otherwise you will wait for the weekend to get any type of reply.

a. Is it an event invitation? Put the date and time in the subject: Invitation on at location Y.
b. Do you want a meeting? Start the subject with: Meeting Request for X.
c. Need a confirmation from them? Add [Action Required] at the beginning of the subject.
d. Is it actually urgent (for them, not for you)? Start the subject with [Urgent][Action Required] Need X.
e. Writing a thank you note? Subject: Thank you for the intro to X.

2. Keep it short — respect is better than politeness

Time is their most important asset. Respect their time. If you make the emails as short and as concise as possible: do it. They will appreciate it and they will understand that you “get” them. The first thing you let go when you are under time pressure is: politeness. You become very directive: do this, help me with that, go there, etc.

Understand that and respect it: that is empathy.

Leave out any logistics and other details aside. They will ask for those later, or most likely they do not even care because someone else handles this for them.

3. Emphasise what matters.

Make sure your email has a clear structure.

What I usually do is I structure my emails in 3 big blocks:
a. What I need
b. What they get (or why I need it)
c. Any information they require to give me what I need.

I use bold for the most important parts of the email: dates, requests, actions. For example I emphasise what I need from them: please confirm by Tuesday, give us your restrictions by end of this week, etc.

4. Don’t suck up

Most executives know what they want and sucking up or flattering will not work. They already have enough self esteem that some email flattering will not work, it will just annoy them. Also it wastes their time.

When you meet them in person, use your regular charm. But not before that.

The details

Short answers from them is good

I remember one entrepreneur Mr. “M”, that always replied with “ok”. Mr. “M” only said “ok” to the invitation email I sent him, or “can’t go”. No matter how many followups I send him, with the location, his calendar, the startups he will see, he never replied to any of them. I was terrified that he may not show up, or he forgot. He always showed up and was prepared with all the details I sent him.

Time is extremely important for these people, but more important is their word. They did not get where they are by breaking promises. If they say they will do something, they will do it. A clear and short answer from them is solid. They will do as they say.

If by exceptions they are the type to break promises, you will find out very fast from all the other execs.

Do not worry if they CC someone else in

No one starts at the top, and no one gets to the top alone. When you are writing to someone who is higher in the professional hierarchy than you, you probably want to establish a personal relation with that person. Expect them to CC someone else in.

Don’t take it personally, it just means they trust their team. If they care enough to reply, that is a good sign.

Discussing important things

Going an extra level, when asking for important things, worry if they do not involve anyone else in the conversation. Usually entrepreneurs and high level execs have partners and core teams that they work with. No one gets to the top alone and they have to rely on others to help them get there.

Usually we see only one part of the team: “The Face”. That is his or hers job. Look pretty, give the direction, take the punches when they come.

Expect them to talk with their partners about what you are asking and with their team. If you want them to be a trusted partner of yours, they should have other people that they trust already and which they consult. Worry if they don’t.

Now start writing!

Image credit: unsplash-logoWalter Walraven


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