By Matthew Gaiser

One of the more profitable areas of freelance writing is the advisory and instructional space. People are willing to pay to learn how to do things better and frequently read blogs that help them do better work. That means the blogs are willing to pay a relative premium for such posts.

I write for Stack Overflow, a technology blog that pays $500 for posts like Have better meetings—in person or remote or How to onboard yourself when your employer doesn’t. This article discusses the pitch I used to publish the former one.

Both of my pitches have been built with five major components. The title, why the article matters, why I am the person to write the article, a quick outline of what I wish to cover, and where examples of my previous writing can be seen.

Part 1: The Title

The title is essentially a half-sentence pitch to the reader about what the article is about and what they will gain from reading it. I tend to prefer the precise and verbose, so concise and punchy titles are not my strong point. I admit this at the start, simply because editors are usually comfortable changing the titles to suit the audience. Some companies even try several different titles for a short period and see which one generates the most reads.

Focus on finding a 5-10 word sentence or phrase which effectively conveys your topic. If you cannot think of something perfect, that is usually fine because the editor will probably want to change it anyway. Do not get attached.

What I wrote in my pitch to Stack Overflow:

Suggested Title: How to Have Effective Conversations with Non-Technicals When You Can’t Be In the Room (Again, I could use some help with the title)

Part 2: Why the Topic/Article Matters

Instructional blog posts can be written on many different topics, but if the instructional is not relevant to the publication or it is only useful to a small subset of people, it is not worth publishing. Consider this piece. On a site about freelance writing, it is a perfect fit but on Stack Overflow, it would be barely relevant but perhaps still passable (I am not sure they would pay for it though) and on a site about economic theory, it would have no value.

In this section, you want to make a case for why what you have to say would be interesting to the readers of that blog. That case does not need to be explicit. Instead, it could just simply reference a recent discussion on the site or even some commonly known pain points.

What I wrote in my pitch to Stack Overflow:

Rationale: The bane of my work is poor requirements. It is extremely frustrating and wasteful to be halfway through building something only then to realize that a requirement does not make sense.  This is exacerbated by the fact that our product owner and many of the stakeholders are in a different office, so we need to extract a lot of clarifying information through email and Microsoft Teams. Working remotely makes communication more difficult, so doing it ineffectively becomes crippling rather than just a waste of time.

The argument I made heavily relies on common experiences among software developers. We have all dealt with poor requirements in our careers. If your topic is not as commonly known to the site readership, it will require more explanation.

Part 3: Why You are the One to Write It

Publications rely on their credibility to survive and attract readers. When you pitch a publication, you are generally asking them to share their credibility with you. They are risking their reputation on your instructional article being accurate.

Because of this risk, they want to know why you are qualified to tell others how to do a particular thing. You do not need a degree in the topic. A good anecdote of how you solved the problem you wish to talk about can work perfectly fine.

What I wrote in my pitch to Stack Overflow:

Why I am the one to write it: I work in enterprise software on a team of developers who have limited experience in the domain (nobody on my project has been at the company for more than a year) and we have had many issues working with a non-technical product owner. I sometimes have to lead the sprint review meetings and wrangle decisions from non-technicals. The product owner and many of the key stakeholders are also often located in a different office, making them effectively remote much of the time anyway.

Part 4: Your Proposed Outline of Topics

Instructional articles usually consist of a set of clear steps. They could be sequential or they could be in no particular order (this like post). It is helpful to give the editor a clear idea of what exactly it is you want to cover as then they can imagine how the entire article would read. Confused people who feel uncertain say no. People who are confident in what they are buying say yes.

What I put in my pitch to Stack Overflow:

Sample Structure with topics:

• Try to understand the domain. It is more difficult to chit chat in Teams over the small details. — Start by finding more common ground.
• Outline the key information at the top of the email/message.  — A bit on structuring that
• Write clearly and split the text into easily digestible bits. – A paragraph on writing clearly.
• Use analogies. — One to one is like having one parent with one child at the zoo. One to many is like having 3 children which is a great deal more complicated.
• Clarify with boolean questions. Keep asking questions that should get definite answers until you get definite answers.
• Present 2-3 choices and force a choice.
• Use mockups and drawings
• End the conversation with a final yes or no. Think of this as the return statement of the conversation.

I am not sure how open you would be to including informative images, but I would be happy to get on Slack and create some examples of effective conversations. A lot of this is really just on effective communication and is applicable advice whether or not one is remote, so I am not sure whether it follows your topic closely enough.

I just listed the major sub-headings which would be part of the article. That is all that was required. In the case of this particular instructional article, each sub-heading was one action item for having better meetings. 

Part 5:  Evidence of Your Writing Skill

Evidence that you can write well is extremely valuable when you make a pitch to a blog. For many publications, the editor is juggling several articles at once.

A writer who can deliver a piece that needs minimal editing is more valuable to them than a writer whose work will require substantial revision. They only have so many hours in a day and the fewer of them that you require, the better.  In your pitch, you want to provide the editor with confidence that what you write will be something they can quickly publish.

Ideally, that evidence would consist of well-received prior blog posts, but if you are new to the freelance writing world, there are alternatives.

I used my Quora profile when I originally pitched Stack Overflow, but I have known people to use essays from school, their own blog posts, or even some writing from Reddit.

What I put in my pitch to Stack Overflow:

I wrote a previous article for you: https://stackoverflow.blog/2020/02/24/how-to-onboard-yourself-when-your-employer-doesnt/. I am also a regular writer on Quora (https://www.quora.com/profile/Matthew-Gaiser-1), Workplace (https://workplace.stackexchange.com/users/111291/matthew-gaiser), and have won a variety of essay contests over the years. 

The result of all this (and a few rounds of edits)  was this article here: https://stackoverflow.blog/2020/04/30/have-better-meetings-in-person-or-remote/.  

Instructional pitches do not need to be complex or highly creative. The goal of an instructional post is to convey a better way of accomplishing a task most straightforwardly. That lets the pitch for them be straightforward as well.