The Art of Communication: Why I Sent a Shakespearean Email for a Software Release

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In the world of software development, effective communication is just as crucial as well-written code. A poorly worded email can cause unnecessary friction, delay a release, or create misunderstandings that ripple across an entire project. That’s why, when it came time to send a routine request to stage a web services deployment, I decided to take an unconventional approach—I sent it in Shakespearean English.

Why?

Because I knew my audience.

The Challenge: A Difficult-to-Work-With Deployer

My company has a person responsible for deploying software releases to our staging environment. He’s talented, but he’s also notoriously difficult to work with. Requests must be precise, and ambiguity can lead to unnecessary delays, pushback, or frustration.

Knowing this, I could have approached the situation with dry, formal language—something like:

Please deploy BigSoftwarePackage (version 1.14.33) to staging. Let me know if any issues arise.

This would have been clear and professional, but it also would have set a tone of pure business. Given past experiences, this could have made the interaction feel transactional, cold, and rigid—leaving no room for goodwill if issues arose.

The Strategy: Humor as a Communication Tool

Instead, I took a different route. I crafted a Shakespearean-style email, complete with phrases like “The hour is nigh, and we stand ready to set forth this work unto the staging realm.”

I did this for three reasons:

  1. Shared Nerd Culture – I knew this person was a nerd and would likely appreciate the humor. A little levity can go a long way in softening a traditionally dry or tense exchange.
  2. AI Recognition – The message was so absurdly different from my regular emails that I knew he would suspect I used AI to generate it. That subtle recognition added another layer of humor.
  3. Goodwill Before Potential Conflict – If there were issues with the deployment, follow-up emails wouldn’t feel like an escalating argument. Instead, we’d already established a lighthearted tone, making troubleshooting feel like a collaborative effort rather than a chore.

The Lesson: Know Your Audience

Good communication isn’t just about what you say—it’s about how you say it and who you’re saying it to. Adjusting your language, tone, and medium to fit the situation can drastically improve outcomes and relationships.

In this case, the Shakespearean email served as an icebreaker, helping mitigate risks I already anticipated. Instead of needing to smooth things over after a misunderstanding, I proactively crafted a message that set a positive tone from the start.

The Takeaway

Whether you’re writing an email, a Slack message, or a formal document, consider the human on the other end. What kind of communication style will make them most receptive? How can you foster goodwill before problems arise?

Sometimes, the best way to ensure smooth collaboration is to throw in a little Shakespeare.