The UX of emails — how to write emails for high level executives
NOTE: if you are 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 to get 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 possible 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 top priority!
My emails were gold, it had all the details and was extremely specific. Just check it out.
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,
George
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 -
Put everything in the title
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 dd.mm at location Y.
b. 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.
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.
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.
