5 lessons I’ve learned from coaching writing

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My work as a technical writer sometimes means that I have to coach solutions architects and other technical people in the fine arts of writing. It’s a part of my work that I’ve come to find a new appreciation for over the past few years.

Here are some lessons I’ve learned:

1. Technical people hate to write, but there are reasons why

There’s a stereotype that technical people can’t write, and there’s much truth to that statement. I’ve had the fortune to work with some technical people who can write and write well. When I’ve brought up the roots of their writing hate, more than one person pointed back to some negative high school or college experience with a teacher. Another frequent response was being too busy.

2. Keep it simple for the non-writer

My rule for coaching a non-writer is to keep it simple for them. Figuring out just how to keep things simple for the non-writer happens on a case-by-case basis for me at least. Here’s a sampling of some things I’ve done in the past:

  • Encourage the non-writer to focus on being methodical and to break down what they are writing about on a whiteboard or on a piece of scratch paper
  • Encourage the logical thinking side of the technical person because of the role it plays in writing technical content
  • Tell them that the semicolon isn’t their friend so use Short paragraphs and sentences to improve clarity in their writing
  • Ask them what they need from me to be successful in writing the document and adjust my coaching approach with them

3. Encourage the non-writer to iterate on writing

I always advise anybody I coach writing to iterate upon what they write and sit on their drafts at least a day before they revise them if they have the time. It’s something I do as a writer, and I often relate my own experience with using this practice myself.

Depending on the person, I also encourage them to write a draft without editing until the draft is complete.

4. Introduce the non-writer to machine editing

Self-editing for non-writers takes time and practice for non-writers in my experience. I’m always happy to recommend machine editing tools to these people. HemingwayApp — which highlights lengthy and verbose sentences — and also Grammarly to non-writers I’m working with on a project. While these apps and others like them can’t replace a human editor, they can help serve as another set of checks for a non-writer who might not yet be confident in their writing skills.

I use that fact that AI is underlying today’s machine editing tools to make it more attractive to non-writers who’d benefit from the technology.

5. Deliver constructive and actionable reviews of what they write

It’s hard to not write in the IT industry and not have some bad experiences with document reviewers and editors. My aim is always to deliver constructive and actionable reviews of documents from non-writers that add value to their document and them.

It’s important to be seen as a collaborator, not as their freshman comp teacher. Part of this collaboration comes from being conversant in technology the document is supposed to cover. You can instantly lose credibility as a writing coach when you try to mold writing to fit your lack of understanding. You gain credibility when you write constructive comments with intelligent questions.

Final thoughts

While I dare say that writing does bring me joy in many circumstances, the same can’t be said for technical staff. I’ve made it my mission as a coach to offer the people I’m helping a positive experience with writing.


I’m a technical writer and content development manager living and working in Northern Virginia. Over my career, I’ve written bylined articles for ITSearchOperations, DevOps Agenda, Mobile Business Insights, CNET TechRepublic, and others. My areas of interest include cloud computing, DevOps, enterprise mobility, and collaboration tools. Follow me on Twitter: @willkelly.

5 things about task lists

When I was freelancing full-time, I gave lots of thought to task lists (in particular my own) because I was managing lots of small projects like articles and blog posts. Task lists kept me on track to meet multiple deadlines every week. On top of that, I’ve written about productivity apps like task list apps for WebWorkerDaily and TechRepublic in the past.

Like many people out there, I try to refine my workflow and tools so I can be as productive as possible and create replicable processes that help mitigate errors and improve the quality of my work.

  1. The road to productivity is paved with discarded iOS task management apps.
  2. Simplicity is in the eye of the beholder.
  3. Productivity is in the eye of the beholder.
  4. Task lists once a traditionally personal affair are now meeting the cloud in tools like Asana where they can be extended to whole project teams.
  5. Some people are better organized electronically than in hard copy, the reverse is also true.

How do task lists impact your productivity?

5 types of people you interview as a technical writer

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Long ago I came to see people as the greater challenge to my work as a technical writer more so than the technology I was writing about. It’s not that I don’t like people. I just came to see people in technology organizations

Here are the five types of people you interview as a technical writer (in no particular order):

1. The poseur

Over my career as a technical writer and freelance technology writer, I’ve had the opportunity to interview a lot of whip-smart people — some brilliant — and I’ve learned a lot from them over the years. I’ve grown fascinated by people’s “tells” especially the one type of interviewee I call the Poseur. Here are some of their characteristics:

  • Beats their chest about being a technologist
  • Abides by the rule that he who talks the most must be smart
  • Dismisses questions they can’t answer by changing the subject or lame excuses

Now mind you there’s more than one type of poseur. You might get lucky and find one who defers technical writer interviews to their employees politely. There’s no harm in these people — they can be great connectors — for technical writers. It’s the ones who lack self-actualization that can cause problems on content development projects as they become a blocker to success to save face and fight politically to prove their own relevance.

2. The old school geek/true believer

While so many folks fall for the mythos of snake people as the be all end all technology experts, give me an old-school geek with gray hair any day as a subject matter expert. I’m talking about the person who has been there, seen it, and done it.

While interviewing some old school geeks/true believers can mean having to put up some guard rails for the interview because they do have their war stories. Old school geeks are often the ones who respect technical writers with some domain knowledge about what they are writing about versus a generalist who’s not really vested in technology.

3. The product person

In my travels as a technical writer, I’ve come to see that there are just product people. They may hold the formal title of product manager, sometimes they might just be an accidental product manager — a product-focused person sometimes a developer — who has a vision for the product they are developing.

My favorite type of product person to interview is somebody who’s had a lot of customer contact and are very aware of the competitive landscape. These people can be a treat to me as a technical writer. I especially enjoy interviewing product people for articles I’m writing.

4. The services person

A services person understands the delivery side of the business versus the product. They may or may not be technologists by trade. I commonly encounter the services person in industries such as financial services, government, and telecommunications where security, compliance, and dare I say bureaucracy is the order of the day.

My favorite way to interview a person is in front of a whiteboard where they can break processes and procedures down while they are telling they are dropping some knowledge on me.

5. The evangelist

While I usually don’t see too many of what I call the evangelist when I wrote technical documentation, I do see them when I write articles, blog posts, and white papers. While I like interviewing the evangelist, it can always be a balancing act in my experience. You can encounter a poseur trying to impersonate an evangelist.

Interviewing an evangelist can be challenging. Some come into a media interview with a definite corporate line they want to push even if you are writing a vendor agnostic thought leadership piece. On the bright side, their enthusiasm can be contagious, and that can shine through in their interview answers.

In my experience, natural evangelists are few and far between, but you can cultivate evangelists. I saw that done when I was freelancing for CNET TechRepublic, I saw a corporate CEO go from a very rough interview to one of my go-to sources on a subject in about two years.

Final thoughts

While my passion for technology keeps me going as a technical writer — on the good and bad days — people also keep my interest in projects. It could be the people and personalities I work with on a daily basis or the people I interview for articles.


I’m a technical writer and content development manager living and working in Northern Virginia. Over my career, I’ve written bylined articles for ITSearchOperations, DevOps Agenda, Mobile Business Insights, CNET TechRepublic, and others. My areas of interest include cloud computing, DevOps, enterprise mobility, and collaboration tools. Follow me on Twitter: @willkelly.

Writing topics I hope to tackle in 2019

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I had a nice week off between Christmas and New Years. Too often in the past, I’d forget to slow down for a couple of days to catch my breath, reflect,, and make plans for the next year. One thing I thought about was what writing topics I want to tackle in 2019.

Here are some writing topics that have my attention going into the new year.

Continue reading “Writing topics I hope to tackle in 2019”