“Begin with the end in mind.”
Stephen R. Covey, The 7 Habits of Highly Effective People
Email, text, DMs…all of these are easy to send and surprisingly easy to make hard to answer. When someone is busy, there are two challenges that drive a response: first is getting their interest, which presumably you have. The second is, structurally, how difficult is it for that person to respond.
I think about this a lot from the receiving side.
On a normal day, I may be in back-to-back meetings with only a few minutes between them to skim messages and respond. If the ask is clear, I can often answer quickly. If the request is buried in a wall of text, I probably cannot give it the attention it deserves in that short break, which means it waits until later, when I have time to sit down and reconstruct what is being asked.
That delay is not always about priority or willingness. It’s purely about – was this easy for me to understand what was needed from me, and was it easy for me to respond.
Over time, I have found a few habits that make messages easier on the person receiving them.
Keep It Short Enough To Read Now
The longer a message is, the more likely I am to make a quick decision to come back to it later, especially if I cannot immediately understand the importance, urgency, or point of it.
That is not because I do not care. It is because a long message asks for a different kind of attention. If I only have two minutes between meetings, I can answer a clear question, but I probably cannot unpack a long thread, infer the real ask, and figure out why this matters to me and what is needed from me.
Give The Message A Shape
Beyond the length of the message, making it easy to skim and understand the ask is critical. A message that contains several questions, a few implied decisions, and background that may or may not matter is more difficult to read and takes longer to respond. Contrast that with this simpler structure:
A useful message usually has three parts:
A useful message makes the next action easy to find.
- What this is about.
- The context the person needs – no more, and no less
- A specific decision or request.
That does not mean every message needs to be terse. The message should be as long as necessary to get the point across, but the shape of the message should be easy to follow.
Help The Reader Triage
For emails specifically, a subject line is very helpful. It helps the reader triage. I use TL;DR and a brief sentence at the start of slack messages to serve a similar purpose, especially when messaging executives and leadership.
“Question” is not very useful. “Decision needed on launch scope by Thursday” is useful. It tells the reader what kind of attention is required and when.
If the point of the message cannot fit into a clear subject line, the message may be trying to do too many things at once.
Frame The Decision
Vague requests create work for the recipient. Compare these two:
“Let me know what you think.”
vs.
“I recommend option B because it reduces release risk. Are you comfortable with that direction, or would you prefer we keep option A and move the date?”
The second version is easier to answer because it tries to layout specific decisions and tradeofffs related to the context provided. They can agree, disagree, or provide a longer response if they choose to.
Bring The Context With You
Before sending a message, ask what work you are pushing onto the reader.
Before sending a message, I try to ask: what work am I pushing onto the reader? Can I simplify this into either a yes or no, or a multiple choice decision?
Sometimes sending a message that is broad or open-ended is unavoidable. If the situation is complicated, the message may need more context. But often I can reduce the work by summarizing the relevant facts, naming the tradeoff, linking only the material that matters, or offering a set of reasonable options instead of an open-ended question.
This matters even more when writing to tertiary stakeholders or or people in other disciplines. They may care about the issue, but they do not have the same context I do, and it is easy to forget how much of the situation I am carrying around in my own head.
Make It Easy To Help
Good messages try to ease the burden on the reader by taking some of that work on myself, so it becomes easy and natural to respond and help me.
- Make the request clear.
- Make the context sufficient.
- Make the decision easy to find.
Sometimes that means a thoughtful paragraph. Sometimes it means a quick yes or no. And especially in text or chat, I try to frame my question so if we’re totally aligned, the only response needed is an emoji confirming the direction.