Everyone has had at least one, but typically multiple, bad experiences with technical documentation. There really is an easy way to fix bad documentation. Hire someone that has a good base technical knowledge with strong writing skills and include them in the business. The best writer has probably done more than just writing - while this maybe not reflected in a previous job title, it will be apparent in the skill set and aspects of previous job functions. You can test this knowledge by having the writer explain code, describe the product or service from a previous job, or write about a topic related to your product or service.
If you are fortunate enough to find a strong writer with a good technical background - maximize this resource. If you really want to make you documentation stand out, include your technical writer in every single aspect of the company. The best technical writers are included in development meetings, help address support issues, assist sales and marketing with content, and develop and conduct quality reviews, product testing, and training. More importantly, the best technical writers can do all of this and speak the speak of not only the company, but the product or service being provided.
Crazy, right? The best job that I ever had had me doing support, testing, training, and writing -> I still remember aspects of this product because I was probably more involved in it than most other people in my department.
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