The 5 Ws of Journalism, Applied to Tech Buying


Rudyard Kipling may have spent part of his life as a journalist, but it was his work as a poet that provided the most useful guidance for other editors, reporters, and even today’s tech buyers.

“I keep six honest serving men,” Kipling wrote in the first line of his poem of the same name. “They taught me all I knew. Their names were What and Why and When and How and Where and Who.”

In just one stanza, Kipling had outlined a framework for reporting on almost any story. These ‘5 Ws of journalism,” as they’ve become known, remind journalists of all the sorts of questions they should ask as they make sense of breaking news. Reporters often try to pack in answers to as many “Ws” as possible in their lede, while the rest of an article often delves into the “How” Kipling mentioned.

The value of the 5 Ws isn’t limited to journalists, though. They can be just as helpful to the CIOs, CTOs, and other IT professionals in tech buying—working behind the scenes at major publishers to develop a better tech stack. It’s by no means an easy process.

According to market research firm Forrester, 86% of B2B purchases stall during the buying process. There are a lot of factors, but it probably doesn’t help that 13 people within an organization are involved in the buying decision on average, with 89% of purchases involving two or more departments. This means even simple buying decisions can get buried in due diligence.

If you find yourself stuck in a prolonged purchase cycle, it may be time to look at the 5 Ws in a new light—where you’re not trying to report the news but make an investment that will lead to good news for your organization.

Try to focus on:

The ‘what’

Whether it’s an emerging artificial intelligence (AI) platform, a new martech tool, or just the latest smartphone, organizations have sometimes been accused of succumbing to Shiny Object Syndrome. 

Publishers rarely have the budget to indulge in technology for technology’s sake, but as an IT leader, you still need to make the “what” behind every purchase clear. What will your investment accomplish?

In some cases this needs to be broken down into short-term vs. long-term outcomes. For example, a survey from KMPG found 58% of organizations still face weekly disruptions due to flaws in their legacy systems. That should make reducing tech debt by migrating a core system like your CMS a no-brainer, but there could be more to your “what.”

Beyond simply reducing performance breakdowns, set goals and targets based on key business objectives. The Association of Online Publishers’ latest report shows that 50% of media organizations are focused on driving subscriptions, with branded content following close behind at 45%. This explains why 52% plan to increase the content they produce in 2025.

Compare this data to your own organization. If the objectives are similar, begin gathering data to benchmark your current state as you look for technology that will achieve them.

The ‘why’

When you’re presenting a proposed purchase to your boss or other stakeholders, they’ll expect you to tell them all the same thing: Why this platform or solution over the others? Depending on the price tag, they might also wonder why it’s worth the money.

Your response needs to cover the fundamentals here:

Take advantage of any publicly available content to prepare you for these discussions. A solid buyer’s guide will give you plenty of “whys” that justify selecting your preferred solution.

The ‘when’

The phrase “timing is everything” should be revised to read “the timeline is everything,” at least if you’re investing in new technology.

What you want to avoid is the classic psychological tactic that parents use on their children, which is to avoid saying “No” in favor of a “Not yet.” This is a way of keeping on good terms with the person whose ask is being turned down while essentially sticking with the status quo.

There will always be looming acquisitions, new product launches, and other items that will get to the top of the C-suite agenda. Your job is not to challenge any of these other priorities but to educate leadership teams about the trade-off they might experience if they keep your purchase on the back burner.

Instead of focusing on innovation, for instance, 43% of CIOs say changing business conditions forces them to redirect their efforts elsewhere. This likely includes maintaining aging software and infrastructure. If publishers’ future depends on providing best-in-class technology to support the journalism they do, the time to move forward with strategic IT investments is now.

The ‘where’

Once you begin rolling out any kind of technology solution, people will expect to see results. The question is whether those results will manifest themselves within your back-office operations, on the front lines where your customers or audience engage with you, or both.

You can talk about this by identifying the business functions that will see the value of new technology first. A new CMS can make life a lot easier for the editorial department, for instance, but also for those in IT and developers who have an easier platform to manage and build upon. You could also broadly talk about this as the employee experience (EX) you’re enhancing with better technology.

The customer experience (CX) in the media sector is not limited to readers or viewers but also brand partners who monetize journalism through advertising and sponsored content.

EX and CX are both important and sometimes, a single investment can address them both. When SWI swissinfo.ch migrated its news service to WordPress and WordPress VIP, for example, the CX benefits included the ability to automatically translate content into 10 languages. Internally, SWI was able to develop custom blocks that make it easier for content creators to arrange content across its site.

The ‘who’

You’re not just bringing new technology into your organizations. You’re also introducing a new set of relationships. This not only includes the vendor providing a solution but third parties like agencies and partners who can assist with any heavy lifting a migration or upgrade requires.

Provide all the relevant details about the ecosystem you can draw upon to anyone who needs to weigh in on the ultimate buying decision.

The best tech companies also offer professional services teams that can help you take the next step in your digital journey as a publisher. These are the “Who” you turn to for improving site performance and fuelling growth, planning for high-traffic events, and architectural consulting that addresses integration and optimization challenges.

And don’t forget the ‘how’

Working through the 5 Ws of journalism is a great way to break out of due diligence limbo and move forward with modernization initiatives by addressing the most common questions and concerns.

Taking the next step is the “How,” but fortunately that’s pretty easy.You’ll feel more confident in your IT investments—and talking about them to others—when you’ve seen them in action for yourself. If you’re interested in WordPress VIP, for instance, schedule a demo to learn more.

Headshot of writer, Shane Schick

Shane Schick, Founder—360 Magazine

Shane Schick is a longtime technology journalist serving business leaders ranging from CIOs and CMOs to CEOs. His work has appeared in Yahoo Finance, the Globe & Mail and many other publications. Shane is currently the founder of a customer experience design publication called 360 Magazine. He lives in Toronto. 



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