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Ichabod Crane and the Headless Email

What follows is a harrowing tale of a lost email searching for its head. It is a metaphor to remind us all of the importance of constantly seeking clarity in our emails to coworkers.

It was a dark, icy night in the winter of the town of Sleepy Hallway. Ichabod Crane, a regular townsman of Sleepy Hallway was out one evening. He could not sleep. He could not eat. He just could not find comfort. So he went for a walk to clear his mind in the midnight air. This of course was a time before the invention of electricity and cars, so there were no streetlights and roads paved with asphalt.  His house was a great distance away from anyone else, so he found himself walking alone on the dirt road. Though late, the night was whispering with sound. Animals were rustling in the bushes. Off in the distance an owl hooted. As he stumbled over the mixture of cobble and dust he ruminated on the dream that had woken him.

He felt uneasy, because it seemed as if he were needed, but in his dream he could not tell who needed him or why. He walked on for a bit and then noticed it. Silence. No leaves were crackling. No animals rustling. No wind blowing. No owl in the distance. He heard his footsteps. And there was something else. Horses? No one horse. He looked up and down the road to see nothing at first. A horse whinny. It came closer and closer, and faster and faster. The horse was absolutely exhausted and running at top speed. Ichabod saw something in the distance. As it came into clarity he could not believe his eyes.

The horse had a male rider on it, or so he thought. The male was huge and… he had no head? Ichabod rubbed his eyes and looked again. Nothing was on the male’s shoulders. But what Ichabod thought was even more strange, yes stranger than not having a head, was that it was holding out something. A large envelope. Once close enough, he could tell something was written in the From address, but nothing was in the To address. This enormous, envelope-wielding man stopped right in front of tiny little Ichabod. The horse snorted and breathed down upon him. Ichabod’s face moistened.

He was absolutely frozen in his shoes. The fear was overwhelming. The large man mounted upon this horse sucked in a large amount of air as if to say something amazing and great. He leaned down into Ichabod’s face, and Ichabod felt like this beast was looking into his soul. And it boomed with a powerful voice the likes of which Ichabod had never heard. It said, “…Hiya”, and then grew silent. It seemed to be waiting for Ichabod to respond.

Ichabod was truly confounded. He did not know what to say, so he only stared back. After a moment with nothing but the horse breathing, this mysterious horse-riding, envelope-waving man huffed, looked around, and sped off into the forest. As Ichabod watched it depart, he wondered, “What was that? What did it want?” After a few minutes of watching in the distance, Ichabod felt exhaustion over take him. So he wobbled back home and went to bed.

Uneasy, he had a terrible sleep for the rest of the night. Unfortunately for Ichabod, it did not finish there. The next week the same thing happened. He got up went out went for a confused walk and again was approached by the envelope man riding without an address. It waived the letter to him, and this time it leaned down him and growled, “…Bump.” It waited. Ichabod was still speechless. It once more rambled off into the distance. “Whatever can that mean?” Ichabod wondered. His fear had died down a bit this time. “What would cause this ghastly creature to be out so late? What was it looking for?” he wondered.

On the third week it ran up at the highest speed yet, stopped and grouched, “…Ping!” It waited for an answer. Ichabod had been thinking over this. He was a bit more confident this time and decided to pose a question. He could begin to tell the male wasn’t evil and scary. This… envelope man, this… “e-male”, as he called the horse rider was desperate. He spoke to it with an awkward breath, “Are you searching for someone? For me?”

This e-male looked at him and laughed with an unearthly diabolical happiness. The horse snorted fire from its nose and reared back! The e-male reached inside of the envelope, pulled out a letter, and handed it to Ichabod. Ichabod was not sure whether to reach for it. The e-male beckoned Ichabod to take the letter by wiggling it. Hesitantly Ichabod took the letter, opened it, and began to read the letter aloud. The message said, “We have a problem in town and we need all of you to come help us. Please attend at once. The problem is…” After finishing the letter Ichabod recognized that it was for him. It was also intended for many of his neighbors. He looked up at the “To” space on the address label to see it was empty. He recognized immediately that this frantic horse riding, headless e-male was looking for its recipient.

To this realization, Ichabod said, “Oh I did not know you were looking for me. You had no salutation.” The e-male groaned loudly and slouched as if to agree. “Did the one who sent you not know my name? Did he not take the time to be more specific? Did he dare send an urgent dispatch to a group of us and not address any of us? How long have you been out here, oh headless emale? How long have you been searching for your recipient? You and your horse look tired and frustrated. And now I see we are all late. Now I see because your sender did not address us by name and instead called out to us with generic phrases like “hiya”, “bump”, and “ping”, that he has caused confusion. He has caused delay. I did not know your message was intended for me until you have retried so many times.” The emale seemed to nod with his shoulders.

Ichabod was thoughtful. “I will go now to the town, and I will meet with your sender. It will take me a day or so, as I am not as fast as you. So please tell your sender one message for me. Tell him I am on my way, and next time to call me out by name. In doing so he will save everyone from lost time, confusion, and frustration.”

With that, the emale bowed to him thankfully, turned his grand horse and rode off back into the night. Ichabod heard the horse breath more easily as it traveled in a happy run back to the sender.

I often see people on big teams send an email to a large group, with everyone listed in the To field. This is a broadcast message intended to capture someone’s attention. For some reason, they believe that by placing five to ten people in the To list, the recipients know the email is intended for them and that everyone will jump to read it. Then that email will sit in their inboxes for a week or even a few weeks. I have seen nearly a month go by before the original sender “bumps” it. They will literally reply all and type one word: “bump”. The eventual result is that someone sees this bump. They then read the email and realize the email was for them. They reply all and say, “Oh, I am sorry I did not realize this message was for me.” Then they provide the answers the sender was originally seeking or do a task that should have been done a week before. This can happen quite regularly almost to the point of embarrassment for the team.

The best practice here is to always call out someone by name in your emails. Even if you have to list two or three people, do so, so that they understand you’re specifically talking to them. It is not abrupt to call people by name. However it does save your organization time and money to be specific when you are emailing a large group. By calling people out by name, they know to whom you’re talking. I encourage you to use a brick red color for names, so that people can quickly scan an email that is significantly long and still know whether you were talking to them. I have been doing this for years, and people, being very pattern-savvy, grow accustomed to the color indicating names.

Be specific, even in broadcasts, so that your email accomplishes the job it is intended to accomplish in a timely fashion. If you don’t have enough information to be specific to an individual, then call one of the people by name and ask for them to direct you to the correct person. If you don’t even have enough information for that, refer to the organization in general and ask for specific contacts.  For example, “Dear Jason or IT, I don’t know who to ask specifically for a solution to (this problem), but can you tell me who normally handles this for us? Thank you.”

Always call someone out, and you’ll get better results every time. When someone’s name is directly called out in an email, they are significantly more likely to respond even, if they tell you they are not the right person. By calling them out by name, you are inherently asking them to reply. More importantly, THEY hold themselves responsible and will generally try to help.

Don’t send “headless email” out into the cold, dark forest searching for their townsfolk. Tell them exactly where to go.