Do you wanna write a blog post? Kicking off a blog-posting culture

One of the important things for us in the Otterize team, from very early on, was making blogging and quality content a core part of our team’s culture. We wanted to be able to share our story with our community - our experiences, successes, hardships, and lessons learned. We felt that, as a team building a product meant for developers, who better to tell our story than our own genuine developers and team?

But culture is never built just by making statements. Blogging did not come easy for most of our team, because most hadn’t written a single blog post before joining Otterize. We really needed a way to get the juices running and help push everyone towards their first post. That’s when I came up with the “_Do You Wanna Write a Blogpost? Writing your first blog post”_ workshop: a one-day all-hands joint effort for kick-starting our blog-posting culture.

Why blog post?

Writing blog posts is a great tool for personal development. First, it helps you own what you already know, by writing it down and proclaiming it as yours. Second, you get to help others, by sharing the knowledge you gained and adding your own thoughts and perspectives to it. Third, you get to learn by teaching. Writing content in a clear, concise, organized, and easy-to-read manner is a skill worth practicing. It forces you to really understand all the tiny details and sharp edges you never knew you didn’t know. Finally, improving your personal digital presence is a powerful tool in the digital era. Making yourself visible and putting yourself out there, with quality content to back up your resume, can generate some amazing personal growth and career opportunities.

As leaders of organizations or teams, providing tools and encouraging your team to generate content as part of their job is a win-win situation. Your organization benefits from better morale and team spirit, and from original content to back up your message. Quality technical content written directly by the people in your team will attract more people to join your team — it’s great for recruitment. Moreover, if you’re a business-to-developer product, your customers are much more likely to be inspired by what your own developers have to say than by curated marketing content. Last but not least, brainstorming, collaboration, peer-reviewing, and co-editing, all make a great team-building experience.

Setting the right goals

Research shows that the average blog post is around 1400 words, and takes about 4 hours to write. However, the truth is writing your first blog post typically takes much longer than that. Moreover, proofreading, peer-reviewing, and editing are all iterative processes that require extra time and resources. So careful planning and consideration are needed in order to make the best out of a single-day focused workshop.

Our first step was setting clear goals for the workshop. Our objective was that each team member ends up with 2-3 proposals by the end of the workshop day. Each proposal should extend a general idea into more than just a short description. This could be an outline, a few paragraphs, some bullets, or even a first draft. Anything that’s elaborate enough to get the juices running and force us to really think it through and put something on paper, while still keeping the required effort within some bounds so we can fit more than one proposal into a single day.

Next, we discussed the type of content we wanted to create. Some people find pure technical content more appealing, while others enjoy writing about soft skills or personal experiences. Some enjoy detailed descriptions of complex system architecture while others prefer a small side-project. My general take for personal blogs is that anything you’re passionate about is worth writing about. However, for a company-wide focused effort, alignment is important to make sure that the end result is compatible with the company’s needs and vision. At Otterize, a business-to-developer product, we wanted to write technical content which is interesting and useful for our developer crowd. And so we encouraged our team to go wild with their ideas and write about what’s genuinely appealing to them, but also asked everyone to try and come up with at least one proposal that is more on the technical side.

Finally, we made sure everyone knows that done is better than perfect (ask Sheryl Sandberg). None of the proposals are binding, no draft will be held against you. We assumed the results of the workshop will require more work. A LOT more work. In fact, time spent on perfecting your draft during the workshop day is time ill-spent. Spend that time on generating another proposal instead.

Kicking off together

And so, the much-anticipated workshop day arrived. The entire team joined, our meeting schedule was cleared, beers and pizzas were ordered, and we all joined forces in our large meeting room.

To kickstart our day and help bring down some barriers, we started our day with a “tips for writing your first blog post” talk (inspired by Dafna Mordechai’s workshop on “How to Write Your First Blog Post”). We talked about our motivation for writing blog posts, how to find inspiration for topics, some helpful preparation methods, and tips for generating meaningful, easy-to-read content. We discussed how painful the editing process can become, and knowingly left that part for later; for our single-day workshop, we planned 0 editing work.

We then had a group discussion about common traps & barriers in our writing process. If you’ve ever tried publishing anything I’m sure you’ve encountered them. These are tiny voices whispering in your ear before you even start writing. “What’s so special about my take on things?”, or “there’s already so much content about this topic, why would anyone be interested in what I have to say?”.

The thing about all of these traps is everyone experiences them. By discussing these traps together and acknowledging them, we were able to bring down our barriers and know we’re all in this together. This is part of the strength of blog-posting as part of a group effort, rather than on your own.

With that in mind, we followed with an all-hands brainstorming session. While some of us already had some ideas in mind, others could use some inspiration. And so the purpose of this session was to make sure that everybody leaves the room and heads for the day with at least one idea to start with. Beware: this part can take a while, but don’t let it waste too much of your precious workshop time. If you’re a large group you would probably want to split people up into smaller groups with some common background, to keep this brainstorming efficient. I also recommend you ask people to write down some ideas in the days leading up to the workshop so that they already have something in mind before the brainstorming session. You could also create a shared document where team members can share their ideas, so that others may be inspired to suggest their own topics.

And now, we write

All in all, our opening talk plus brainstorming session took an hour out of our day, which left us with some 5-6 focused writing hours. But, despite our high motivation when leaving the meeting room after our kickoff, still almost everyone encountered the infamous writer’s block. Some were still stuck on getting their ideas going, while others promptly stepped on all of the traps we’ve just discussed. Not to worry - that’s all very natural, especially when writing your first blog post.

To help everyone keep going, we anointed a small group of consultants, which we nicknamed our [rubber ducks](https://rubberduckdebugging.com/). These were a few of our team members whose primary objective throughout the day was to help others keep their brains going. Having an available person to talk to while writing your first blog post can make the difference between a half-baked cut-short blurb, and a full, coherent draft. Our rubber ducks were also proactive throughout the day — asking people how they’re doing, suggesting helpful insights, and reminding everyone of our common goals. Naturally, our ducks were left with much less writing time, but that’s ok because they were the exact people for whom writing comes more naturally.

At the end of our day, we shared some of our proposals in an all-hands demo session. Demos are a big part of our culture in Otterize — every other week we all get together for a happy-demo-hour to share our work with the rest of the team. So we were not gonna miss out on this opportunity to show off our blog post proposals to each other. Each participant gave a brief overview of one of their proposals, leaving some room for a round of much deserved applauses, followed by some peer feedback. This summed up an intensive yet extremely satisfying day, as agreed by everyone on the team. You could sense the team-culture-building energies flowing in our office space.

From raw drafts to full-featured blog posts

At the end of our workshop day, we had 13 proposals ready (with an average of over 2 per person). Even the most skeptical team members, those who didn’t believe they had it in them, ended up writing great proposals.

But we’re not done yet. Our first raw drafts definitely helped get things going, but there was still a long way between these drafts and actual blog posts. Over the course of a few weeks after our workshop day, we selected a handful of proposals and built them up to full-featured posts, which we’re intending to publish in our company blog. The selected proposals went through an iterative process of peer-reviewing and editing.

On the way, we learned that story-telling is hard. Most of our proposals needed careful feedback and a number of iterations before reaching a quality outline, with a concise story and clear messaging. In retrospect, we should’ve considered this step of outline review in advance, and given it a proper time and place in the process. Reviewing the story at an earlier stage, and clarifying what the story is and isn’t about, would have avoided the disappointment of having to throw content out after having spent significant effort writing it.

We also learned that some people find it easier to start with a list of bullets and expand from there, while for others writing long paragraphs and editing later comes more naturally. We needed to find a way that respects everyone’s styles while keeping an open mind for feedback and suggestions.

Finally, we learned that throwing everyone into the deep end after the workshop day wasn’t working for us. Most of us still needed some guidance and encouragement when building up our blog posts. Like any other effort, assigning clear goals and an owner helps. And so we declared our blog-posting champion (me!), who’ll overwatch this effort and make sure we keep on our good blog-posting work.

Keep the momentum going

Our workshop day’s primary objective was kicking off our blog posts, but it wasn’t just about that. Ultimately, our goal is to make blogging and content-generation part of the Otterize culture. To do this, we have to make sure this is not just a one-off. And so, we make sure we give it enough time by creating tasks for writing our blog posts and putting them in our backlog, prioritizing them among other tasks. We keep talking about our blog posts as part of our demo sessions and company updates. We opened a #blogposts channel in our Slack, where we share our drafts and ideas. We offer our ideas and feedback to one another, and encourage our colleagues to write more.

These and many others are our way of saying that, as a team, we consider content generation a vital part of our job. It’s not a sidekick. It’s not just a best-effort. It’s part of who we are. And so, all of this is just the beginning.