November 2015
By Keith Boyd

Image: © Andrew Rich/

Keith Boyd has over 15 years of experience as a content professional. He formerly managed the developer documentation team in the Cloud and Enterprise (C&E) division at Microsoft, and previously held the same role in Windows. He recently joined the Microsoft Learning team as a Business Development Director for the Microsoft Virtual Academy.




The (content) innovator’s dilemma

Content professionals are under constant pressure to innovate, yet there’s significant tension between innovation and nailing the fundamentals. Principal Director at Microsoft Keith Boyd describes those tensions by comparing Windows releases and their relative level of focus on fundamentals vs. innovation. His key observation after managing content teams at Microsoft for over 15 years: You can’t have it both ways – you have to make a choice.

The story of Windows: finding the right balance

I joined Microsoft 15 years ago as a Software Test Engineer supporting Internet Explorer 5.5. At the time, it was the best browser on the market – Netscape was in full decline, and it was years before the industry would regroup and begin competing actively again with Microsoft for browser supremacy. Windows 2000 was state-of-the-art in the enterprise, and while Windows ME was the current offering for consumers, the majority steered clear, preferring the relative stability and familiarity of Windows 98. Windows 98 may not have been recognized for being innovative, but it was recognized at the time for being fundamentally sound. Much like Windows 2000.

2001 brought the world Windows XP, arguably the most loved version of Windows ever, and still powering millions of PCs worldwide. While introducing some innovative features (most notably the new “Aero” user interface), Windows XP became so beloved because it nailed the fundamentals and offered sufficient innovation to satisfy power users. Because XP utilized the more robust Windows NT kernel, it provided users a more resilient and reliable computing experience. It was a big step up from any of the Windows 9x family (95, 98, and ME).

Alas, riding the high of XP, the Windows team shot for the moon and missed with Windows Vista. Whereas XP was all about nailing the fundamentals of the computing experience, Windows Vista was about pushing the boundaries of innovation. Sadly, Vista failed on both fronts, offering little in the way of genuine innovation and regressing the fundamentals of the computing experience. It was the worst of both worlds, and Microsoft’s competitors took full advantage.

Shortly after the release of Vista, a new management team was brought in to take the reins and fix Windows’ damaged reputation. Three years later, the much-beloved Windows 7 was released. Why was it so well received? Because it got back to basics. Everything just worked. Microsoft was on a path to repair the damage that had been done by Windows Vista, not by doing anything radical, but by focusing on the fundamentals.

Unfortunately, the period of relative calm didn’t last long. Apple released the first iPhone shortly after the release of Windows 7, sending Microsoft leaders and executives quickly back to the drawing board. They conceived of another moon shot – Windows 8. Much like Windows Vista before it, Windows 8 was a release that focused on innovative new features and radical changes to the Windows user experience. The changes ended up being so radical that mainstream users couldn’t adapt. Instead of stanching the bleeding, it accelerated the trend towards competitors’ devices and services. Windows 8 was another black eye for Microsoft.


Nailing the fundamentals

As a content manager at Microsoft in the Windows division throughout this journey, I had a great vantage point on the wild gyrations between platform innovation and basic fundamentals. With benefit of hindsight, it’s clear that releases like Windows XP and Windows 7, where the company made a conscious effort to focus on the basics, were successful – both in the marketplace, and in the court of public opinion. Releases that attempted to redefine the computing experience in new and novel ways like Windows Vista and Windows 8 failed to excite consumers or enterprises or ignite a virtuous upgrade cycle like Windows XP and Windows 7.

It’s probably not a surprise that content strategy for each of these releases tended to skew toward the ambition of the release. With Windows XP and Windows 7, the focus was on nailing the fundamentals – excellent reference material, clear and concise technical overviews, and tutorials for key scenarios of interest to the audience. For Windows Vista and Windows 8, we had greater ambition. Windows Vista saw the content professionals at Microsoft pushing the boundaries – attempting new content types, new metadata taxonomies, comprehensive end-to-end samples, new media experiments, etc. Windows 8 was similar in the scope of its ambition – samples for every new Application Programming Interface (API), radical new content types, and heavier investments in video and other media. In both cases, much like the product team, we lost focus. The volume of content was high, as was our ambition for delighting customers, but the quality was necessarily lower. Quality was lower because we attempted these ambitious strategies without the benefit of sufficient additional contract resources or FTE staffing. The result was an unfocused content strategy that left our developer customers in a lurch, unable to realize the value promised them by these new releases of Windows. We could point to novel new experiences, but had a hard time defending the basics. Both releases suffered in the marketplace, and content strategy was partly to blame.

Figure 1 graphically demonstrates the balance of effort in each release of Windows content. The ratings for percentage of effort are subjective – I can’t find a way to actually quantify this. But they’re based on my well-informed opinion as a leader and manager for each release.

Figure 1: Innovation vs. fundamentals: balance of effort per release.
Windows market share data courtesy of NETMARKETSHARE.


As you can see in the legend, the blue line represents the percentage of effort expended in each release for creating novel or innovative content types and experiences. The orange line represents the percentage of effort focused on nailing the basics. The gray represents the current market share for each of the versions of Windows. While correlation does not necessarily imply causation, I do believe that great fundamental content experiences affect the rate of adoption of a platform or service. Note the inverse relationship between the focus on content innovation and market share. Coincidence?

Here’s another graphic that I use to help my teams understand these fundamental tensions:

Figure 2: Fundamental quality or novel experiences? Make your decision and
live with the consequenses.


Unless you work in an environment where money grows on trees, you’re likely to experience these dual constraints in your role as a content professional. Make no mistake that your executives will want to have it both ways – amazing fundamental quality and novel new experiences that catch your competition off guard and delight your customers. In my experience, these tensions are irreconcilable – you have to make a bet and live with the consequences. My advice is to consciously make a bet on either the top-left or bottom-right quadrant and live with the consequences. Defend your decision with your executive team, and if you decide to focus on fundamentals, use the lessons learned from all those releases of Windows to your advantage and to justify your decision.


Tips for nailing the fundamentals

A content strategy predicated on innovation may be the near-term envy of your competition, but it tends to be rather shallow when it comes to depth of material and may hinder long-term adoption. A content strategy based on solid fundamentals may disappoint your executives initially, but may also lead to longer-term success and happier customers. Finding the right balance between these opposing constraints is difficult, and to this day in my career I’ve had a hard time finding the “sweet spot” between the two opposing concerns. But that doesn’t mean you shouldn’t try. Here are three tips you can use to make sure you’re really focused on great fundamental experiences.


1. Know your customers, inside and out

The very best way to know that you’re nailing the fundamentals is to know your customers. You need to have walked a mile in their shoes and tested the product or service from their perspective. Gather as much data as you can about your target customers – how do you expect them to use the product? What are the boundary conditions? That is, what are the scenarios that are less common, but still core to the product or service? Enumerate the scenarios associated with your product or service, and then rate them in priority from 1 (highest) to 3 (lowest). Those scenarios that are ranked 1 are critical to customer success, those ranked 2 are important for customer adoption and satisfaction. Those ranked 3 are nice to have – get to them if you can, but recognize that they aren’t necessary for a great fundamental experience. It’s better to put the effort into really nailing the higher priority scenarios. Absolutely nail the scenarios ranked one, get to as many twos as you can, and leave the threes behind, at least for now. If it turns out a three actually should have been a one, you’ll find out when you…


2. Validate your assumptions

You’ve gathered the data, and walked a mile in their shoes. Now what? Get out into the field and talk to customers. Validate your assumptions about their usage patterns, and test your assumptions about scenario prioritization. There is no better tool than meeting with customers face-to-face to discuss content strategy – it’s amazing how those conversations can illuminate new ideas and challenge your assumptions around use cases. If you lack the ability to get in front of customers face-to-face, online polling and surveying can be used. Just make sure you include actual external customers. Validating your assumptions using internal customers can yield a content strategy biased toward your organization’s business strategy, which is exactly what you’re trying to avoid.


3. Less is more

One of the most valuable lessons I’ve learned in my career is that when it comes to content, less is almost always more. Intentionally produce fewer, higher-quality topics focused on the right core scenarios, instead of more lower-quality topics that cover the breadth of scenarios your product or service can support. If you’ve done your homework and validated your assumptions, your list of scenarios should illuminate what content is vital to customer success, and what content is nice to have. Once you’ve shipped your product or service, listen carefully to your customer feedback to identify where customers are struggling. Only then should you “fill in the gaps” with additional content, to cover the critical customer scenarios you were unable to anticipate. Face it, most of your customers don’t actually want to read your content, regardless of how good it is! Give them less to read, and they’re going to be happier customers.


Choose your path

In my experience shipping content for multiple versions of Windows, I’ve learned that fighting the temptation to do something glitzy and eye-catching and, instead, focusing on nailing the basics, yielded the best possible outcome for my customers. Those releases where we focused on fundamentals like Windows XP and Windows 7 have always been hits. Innovation and novelty always left a sour taste in our customers’ mouths. Which path should you choose? Just ask the engineers behind Windows 10. They went back to the basics, and the world responded exactly how I had anticipated – positively.

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#1 Eric wrote at Wed, Nov 04 answer

Great article, Keith! One minor nitpick: XP didn't have Aero, it had the much-derided Luna ("Windows FP"). Aero came in with Vista.

#2 Keith Boyd wrote at Mon, Nov 16 answer homepage

You are correct, Eric! After all these years my code names are starting to bleed together. Thanks for taking the time to point it out.