Imagine you’re writing a document, responding to an email, or writing a quick memo. You have a story you’d like to tell written out in your head: We should do X, Y costs this much, and we’re planning on doing Z.

How you tell that story is all about anticipating questions and answering them before they’re asked.

One of the clearest differences between junior and senior employees is how they approach communication. Often, a junior employee will lay out the details that feel important to them, answer the questions important to them, and propose actions they would like to take.

This effectively screams, “I’m inexperienced!”

A senior employee, writing the same communication, lays out the details important for their audience. They answer the audience’s inevitable questions. They propose actions that can be understood by their audience and explain why the audience would care. They go a step further by anticipating and answering the clarification questions their audience will inevitably ask.

The one tool that makes all the difference is empathy—the ability to understand others from their perspective. This includes the ability to understand what information they’re interested in, what their needs are, what their priorities are, what information they already have, and what knowledge they don’t have. Essentially, empathy puts you on the side of your audience: I understand you. I can feel your needs. This is about you, not me.


I love developing new leaders at Amazon. When mentoring others on this topic, I always propose a simple tool to use to know when they’re nailing or missing the mark: If you get follow-up questions to your communication, you’ve made an error.

At Amazon, leaders are encouraged to be self-critical. In this situation, if we get follow-up questions to an email, it means we should assume we’ve failed to provide a complete communication. Similarly, if we receive a question that could have been answered in a document, we consider the document flawed.

The perfect document, email, or memo should require no follow-ups, other than the ones intended. If it requires replies, this is an opportunity to learn and communicate more clearly in the future.

Of course, it’s possible some questions couldn’t be anticipated, you’ll receive unreasonable data requests, or your audience might not have read your whole communication. Still, I believe a strong leader will assume they’ve failed by default, and a junior leader will assume the other person failed.


A common form of communication at Amazon is the “we have a problem” email. Usually, it’s a junior manager’s email to their leadership team: “FYI, the XYZ service is currently experiencing an outage. We believe the impact is minimal and will send an update later.”

What this says is: Not only is there a disaster, but it’s not under control.

Let’s look at the obvious questions that will be sent back immediately: What is the impact of this outage? Full outage or partial? Do we know what caused the outage? How do we measure minimal? What does “later” mean for the next update? Who’s going to send the update?

When coaching leaders on improving their communication, their frequent knee-jerk response is, “But, I was too busy to write a full explanation.” My answer is that providing a tiny bit of context does not take a long time, and the inevitable flood of follow-up questions is a much larger distraction. Also, now you’ve lost credibility and you’ve failed to reassure your audience that you know what their concerns are and can handle them.

Here’s an example of a senior manager’s email to their leadership team on the same topic: “FYI, the XYZ service is currently experiencing a 50 percent outage, approximately. We do not know the cause yet. Customers impacted are those registering for a new account. We do not yet know the number of impacted customers, but we’re investigating. Customers who attempt to register have a 50 percent chance of receiving a ‘try again later’ message, and they can click retry to complete their registration. I will send an update within one hour with our current status and further updates on the above.”

What this email says is: There might be a problem, but someone’s in charge.

The above email didn’t take significantly longer to write and it anticipated the inevitable questions. To break it down further, “We don’t know the cause” is significantly better than not mentioning the obvious question at all, and the statement removes the necessity of your audience emailing you back. You’ve clarified the impact to customers. You’ve set a concrete deadline for follow up, so no one is left hanging. You’ve identified yourself as the person following up, so there is clear ownership over the communication. Basically, the manager here has answered pending questions and likely bought an hour to figure out what the heck happened.


When writing a document, there’s more time to think. But also, your audience will have higher expectations and have more time to come up with questions. This requires multiple levels of empathy.

Similar to the “Five Whys” when writing a document, continue to ask questions from your audience’s point of view until you feel you’ve exhausted all reasonable questions. For example, take this statement: “Younger children use applications less often than older children.” Keep clarifying, using the Five Whys as a guide:

  1. Children ages 2–6 use applications less often than children ages 7–12.
  2. Children ages 2–6 use applications 23 percent of time spent compared to 38 percent of children ages 7–12.
  3. New FAQ item referenced in a footnote: “Time spent on content types by age is XYZ.”
  4. New FAQ item referenced in a footnote: “Top content used by each age group is XYZ.”

It is often clear when you’re reading a document written by a senior employee versus a junior employee. After reading a senior employee’s document, you’re focused on the big questions the document presented to you; for example, should we approve the recommended option A or consider option B for our long-term strategy? When you’re reading a junior employee’s document, you’re likely to get tangled in follow-up questions, clarifications still needed, and missing data. I’ve been in dozens of meetings that needed to be rescheduled for a second hour due to a document that was not clear.


Learning the skill of empathy is one of the easiest ways to improve your communication. It’s about being clear and anticipating how other people think. Consider what your peers, junior team members, and leaders know, think, and need. Remove additional work from the desks of your peers and management because you empathize with their needs. Once you’ve demonstrated that you care for them, you will spend your valuable time on the important topics, and less time clarifying what you should have done properly the first time.

“Maybe part of our formal education should be training in empathy. Imagine how different the world would be if, in fact, that were reading, writing, arithmetic, empathy.”—Neil deGrasse Tyson