On Writing and Meetings

Big Company Problems

In tech, the size of your company shapes the sort of problems you’ll encounter in your job. In a startup, with relatively few people, ensuring you have enough folks to cover all the bases may be a big concern. In a large company (a so-called “enterprise”), you may have entire departments devoted to build pipelines, security, internal tools, reporting and more - technical competency isn’t always the problem, but deploying it effectively can be. Once an organization gets over a certain size, the “big company” problems will start to surface: too many meetings, silo-ed org structures, competing priorities, unclear direction, and so on. You’re putting more people in the boat but still trying to have everyone row in the same direction. It’s naturally more difficult.

Regardless of your role, the value of your communication skills goes up if you work in a larger company. The weight of more teams and departments gets heavier and heavier as an organization grows, and to cut through the overhead and administrative hoopla, you need to be able to think and write clearly. Sounds simple, right? In my experience, it’s not as easy in practice.

Meaningful Communication

Don’t confuse chatter with real communication. We all may be surrounded by meetings, emails, chat messages, and more during our workday, but some of this is just noise. Meaningful communication moves the ball forward.

If you’ve ever been in a multi-hour meeting where the only conclusion was to have follow-up “working sessions”, then you know what I’m talking about. This can happen because the original meeting had too many people, or the wrong people, or no specific agenda, or the questions to be answered weren’t laid out clearly, or perhaps relevant background material wasn’t sent out in advance (or no one read it until the meeting started).

If you’ve ever attended a demo or “sprint review” where someone was mumbling along about their burndown chart, then you know how useless this is. Slowly, laptop lids will open, phones will slide out of pockets, people will quietly peck away at something more meaningful to them, and everyone will pretend that the meeting was worthwhile. It wasn’t, and you should cancel the next one.

Seek first to understand, then to be understood.

So, in a big company, how do you communicate effectively? Sometimes lists are clearer than prose, so let’s have a crack at it:

• First, realize that in order to write clearly you must think clearly. Ask yourself what you are writing and why. Is it necessary? Could it be shorter? What’s the point? Do the people you’re sending it to really care?
• Recognize that you may be out of practice. Writing well is a skill like any other, and if it’s been a while since college, you may be rusty. Re-read what you write, trim it down, get to the point first, then provide explanation or context as necessary.
• Be able to dispassionately argue your point. There are counter arguments to your position, you should know them ahead of time, and ready to address them. Your job is not to “win” an argument, but to find the right solution for your team, company or customers. Be prepared to be wrong.
• When writing emails, do not enter the recipient list until the copy is complete (and edited). This helps prevent accidentally sending a draft, but also helps you focus on the message first.

Hiring process should include a writing sample.

If you help interview candidates, consider requesting a writing sample. Skip a few technical questions, and find out if someone can explain concisely why a service outage may have occurred, or if they can clearly present the reasoning behind a strategic change of course. This is especially crucial for executives - part of a leader’s role is to keep everyone on the same page, and this cannot always be done via town hall meetings. You must be able to write well.

Finally, on meetings:

• Never send a meeting invite without context. Always include a list of questions to be answered (and why), and links to relevant background material.
• Don’t use meetings as a time organization tool. If you get to the point where you don’t know what to do if a meeting isn’t scheduled, you have a problem.
• Written communication is self-documenting, unlike meetings which require minute-taking, or a recording (but no one really watches those, right?)
• Don’t ask to “have a chat” about something as a first reflex. Why does it have to be a chat? Just send the questions and start from there. Skip the “hi, how are you?” stuff and just ask what you need to ask, to whom it needs to be asked, and as succinctly as possible.

Exception!

A 1:1 chat does not fall under the Umbrella of Doom about meetings. Because it’s just two people talking, a 1:1 is informal and can be a great way to get ideas out without the forced formality of meetings. Some useful types of 1:1s include:

• Weekly/bi-weekly chat with your manager.
• Quarterly “skip level” chat with your manager’s manager. These can be a great opportunity to broaden your horizon and to understand problems outside your zone that the larger company is working on.
• Mentoring sessions (a must if you believe in software as a craft.)
• Sync-ups with others who share your role/title, but are in a different department.

So don’t fear 1:1s, they’re not really meetings!

That’s all, until next time, happy writing.