25 Hard-Won Insights from 25 Years in Digital

March 15, 2016 | John Berndt

old man with laptopTwenty-five years goes by very quickly—faster than we would have guessed! It happens in a cloud of memorable episodes, snapshot moments of clarity and challenges—and over time, some important insights shake out.  Hindsight is always 20/20 of course—humans are geniuses at making narratives out of chaos. Grab a drink and pull up a chair, as I take you on a journey a quarter of a century in the making! Maybe grab a few drinks actually, and a pizza; sifting through 25 years takes a little time…

What would have been helpful to know up front, that might have made a difference along the way? Always subject to revision in the light of new experiences, here are 25 important things I didn’t know diving into the digital pool:

1. Projects have a scope, but success is what matters.

A balance certainly exists, but what really matters is delivering value that is contextually relevant (even if the understanding of the context changes after we sign the contract) rather than adhering to a conception of the project that may have been premature. No one feels good about building websites and digital work that doesn’t have a remarkable outcome. With large projects particularly, there can be a danger of losing the thread of why the project exists in the first place. Don’t do that.

2. How people behave reflects in the quality of their digital work.

Over time, I’ve observed a strong correlation between character and quality of problem -solving. People who are divisive and reflexively self-promotional may be talented or have good ideas, but when it comes to execution, it usually occurs at half-mast. The combination of humility and curiosity wins the day.

3. Technologies don’t move in straight lines.

That déjà vu you feel may just be the laws of physics. It is typical that the evolution of technologies takes all sorts of branching paths, and new life breathes into old ideas by small technical changes. We’ve seen all sorts of technologies come back that we would never have imagined had legs: JavaScript, Web standards, XML, client/server computing and more. They all had more than one lifetime to work it out.

4. The full value of digital has (always) yet to be realized.

In digital, predictions of value generally are 5-10 years off reality, except when they arrive and seem utterly novel (though almost always a prediction 5-10 years before was popular and then forgotten). So many small pieces must align to realize the value. The process doesn’t seem to continue, and so many disorienting possibilities that are discussed today will have much more grounded meaning in the near term. At the same time, much of the value from digital also needs to be examined critically even after it shakes the world. We tend to experience it as an act of nature, but the direction and impact of technology is far from straightforward.

5. There are no final answers to UX questions.

What used to be called Information Architecture and is now more properly called usability and UX is a crucial discipline, with a ton of lore and some grounding in other areas like perceptual psychology and testing. However, it is not a science. Furthermore, it is a categorical error to believe in absolute answers to UX questions, which are always relative matters of balance and harm reduction, usually taking place within an overload of use cases, difficulties of testing methodologies, and shifting sands of user orientation. It is possible to get to be “better” or even “great” but not to “perfection.”

6. Content is an economic & a management problem.

Creating content is a major headache for digital projects and often a zone of opacity. This is partially for economic reasons; the content vendors that would solve this problem either don’t really exist, or where they do, often don’t have the bandwidth to do the required depth of work. The inappropriately light treatment of content is so epidemic that it has become invisible. It is the great unsolved problem of digital projects. Often, a severe under commitment to content exists at the management level or a misunderstanding of what is involved, which makes a kind of sense, since developing large amounts of content is qualitatively different from what most organizations do (aside from publishers and news outlets). Of all the clients, those two types of organizations are the ones that are least likely to have the content problem.

7. User behaviors & user expectations aren’t static over time.

What users could relate to in 1993 was dramatically different from 2003 or 2013 for that matter, and it is still changing. The humans that we design digital products for are culturally changing in relation to digital, and that changes what they can relate to. Usability is built on micro-digital-competencies, that is, knowing that an accordion might expand if clicked, understanding the component that one sees, distinguishing various levels of commitments implied by different interface elements and what is likely to follow them, knowing to scroll on a page, etc. The preparedness of audiences change over times in ways that are both unpredictable and messy, and these shifting sands have a huge impact on what works and what doesn’t in digital. We are designing for the ages: we are designing for rapidly evolving visual and interactive language competencies.   

8. Standards are what make everything possible in digital.

An inherent tension in digital endures between technical innovation and the clear, shared standards that allow more than one person to work on something—and which enable collective creation more generally over time. This dynamic plays out in a million different ways, but at its best, smart people design elegant standards that are understood by many. They also enable collective problem-solving and the advancement of digital development culture and standard capabilities. Spotting the standards that will be valuable and have high uptake is one of the more difficult aspects of digital. Some of the most promising ideas, like Java, look very questionable in retrospect, despite having driven many billions of dollars of development.

9. Great digital professionals are born & cultivated, not made.

The combination of attention to detail, flexibility of mind, stress management, and creative spark that make great professionals is extremely hard to find—and even harder to create from scratch through training. There are many very smart people who are just not made for it. Track record is also not the best predictor of performance, since so many aspects are obscure about how a particular project got done. The best have a combination of curiosity, passion, and an ability to process large amounts of information that may go unnoticed in environments that aren’t built to evoke them but then may flourish when someone takes a chance, based on a gut feeling. Hiring is by far the hardest part of creating and sustaining a successful and vibrant digital firm.

10. Getting the meaning out of data always involves falsifiable theories.

As in economics and scientific practice, getting meaning out of data is a murky business. It always involves pre-existing theories about what is possible. The most refined scientific pursuits continue to be ambiguous and uncertain, and in areas like Web analytics, optimization, and audience segmentation, the best practices are the ones that look for the hidden angles, but are highly skeptical and embrace the ambiguity.

11. A lot of professionals don’t get the methodological challenges of user testing.

Related to the point mentioned above, user testing, which is an extremely powerful technique, often struggles to be put into an appropriate context. People are right to do as much testing as they can (with as thoughtful methodologies as they can) but also need to temper their understanding with a view to the reality: even the most well-funded organizations struggle to execute as much testing as would achieve any kind of statistical significance. The best use of user testing is as a qualitative aid to a strong underlying usability practice, designed to bring in qualitative concerns that might be missed. Far too many “experts” believe that a tiny amount of testing somehow trumps that underlying practice—or supplants it.

12. You can’t balance conflicting digital imperatives until you really understand them.

Individual digital generalists have a justifiably bad reputation, but one can make a strong argument for broad cross-education among all the digital disciplines to allow for compromises between conflicting imperatives to be resolved maturely. Consider the opposing cases of designers building SEO-deadly Flash sites a decade ago, while SEO consultants rallied for keyword-crammed pages that were unusable to humans. How much waste could have been avoided if either party was motivated to understand the bigger picture? We can only find a way through by understanding the other side’s techniques and imperatives.

13. Subtle UX considerations define what digital formats “are.”

This is a difficult subtle point but an eerie one for anyone who puts the time in and tries to really understand the deep basis of similar but highly differentiated technologies. We see many technologies as radically different—say XML vs. an SQL database vs. a modern object oriented database—all made up of 0’s and 1’s where the differences are really defined by subtleties of the usability, features and efficiencies of how we are able to interact with them. We come to think (from habit) that a file system is very different from a database from the contents of a file, but what is the real difference? It’s mainly how we are allowed access to the content. A perspective is that all of the level divisions only exist by norms of usage, convention, and stipulation—and that is weird.

14. 90% of software never gets used, & at least half of that is a tragedy.

In digital, I see patience and engagement with tools as an extreme virtue. Being willing to really invest in reading documentation, training, discussion groups, and whatever else helps you understand the tools you use is an activity that pays huge dividends over time. Many times in my career I’ve finally understood some feature in software I use all the time that, if I had known about it the previous 10 years, would have saved me hundreds of hours (no joke). Sure, a lot of software is cruft and doesn’t work well, but humans routinely shoot themselves in the foot by not going another 20-30% deeper. I often wish I had!

15. Special projects & internal efforts need strong project management.

This one is obvious but took a long time to fully comprehend. It can be tempting in the crush of busy weeks to view special projects that crop up as tasks that are just handled in the flow of other work. The painful reality is that anything that is important needs a project manager and needs to be tracked or else it is likely to get lost in the fray.

16. Programmers can see “the big picture.”

I used to believe some of the cultural cliché’s about programmers until I arrived at the modern TBG development team, who I feel good about in nearly any kind of discussion, and who advocate for the big picture pretty much all the time. It is hard won to get there, but it isn’t a cultural absolute that developers have to be myopic.

17. Always cultivate strong mentors.

The best way to learn a lot of stuff fast is to find people who know 100 times more about it than you do. Such relationships can be worth many times their weight in conferences, research, reading, and colleagues. My career might never have afforded opportunities if it hadn’t been for a number of key figures (you know who you are) who I was lucky enough to become friends with—and then politely try to suck their brains dry (requisite zombie reference)!

18. Simplifying fads are always wrong at some level but also always reveal something.

In digital, an eternal pendulum swings between the desire to simplify what is “in front” of the user and the need for the user to be able to do (many) things. It swings back and forth, usually with a shell game like process where complexity is hidden with one hand, but re-emerges on the other side, as the pendulum swings back. An example is the absence of a visible file system on smartphones, where file-system-like attributes start to creep into individual apps. However, it isn’t the case that nothing is learned in this process (even if it isn’t what it seems to be on the surface) since in the process, lots of innovation around interfaces and form factors take place.

19. Democratic participation produces greater value.

To the extent team members can meaningfully influence outcomes, they will have much greater investment in projects, and it will have huge impacts on the thoroughgoing quality of efforts. Finding the right ways to balance group decision-making with the impersonal rigors of business is one of the greatest challenges of the current period.

20. The popularity of platforms & technologies unfortunately matters.

Technologies evolve at all different speeds—sometimes with rather short half-lives. There are promising flashes-in-the-pan and slow-and-unsexy winners. For both digital firms and their clients, technology choices add or subtract value partially in terms of the careers of those technologies, both in terms of how supported they are long-term, and also in term of the richness of culture. This is not necessarily a function of the quality of the underlying technology: in some cases a superior technology may languish while an inferior one flourishes for reasons that are complex and social. Unfortunately, paying close attention to this layer is crucial, since there are many scenarios that arise where the technically best may be the enemy of the good. On the other hand, occasionally technical comebacks of better technologies are consequential from time to time as well.

21. Different technology cultures parse skill sets differently.

When communicating across technical subcultures, language can be highly misleading—the same words have different meanings in different social contexts. Words like “UX,” “Taxonomy,” and “Information Architecture” have subtly different meanings in the subcultures of custom application development, Drupal development, and ASP.NET CMS implementation. Likewise, technologies impact the nature of resource roles in structural ways—as some technologies imply more abstracted UX development (theming) and more formal development cultures tend to drive separation of technical roles (into architect, developer, etc.). Understanding the differences between the use of terms and nuanced approach to development among various subcultures can have huge implications for understanding digital in general, including the competition between those subcultures.

22. Job descriptions are important.

Digital, by nature of its high rate of change and relative youth, has a tendency to produce generation after generation of “digital generalists.” Although such talented people can be extremely valuable in the realm of small projects, when projects reach any level of complexity, it becomes rather important to have clear areas of specialization. In turn, these specialists, if they are exceptional, are likely to thrive only if they achieve the conditions for their work to be meaningful, which means having clarity around their job descriptions and areas of influence. Current trends in methodology sometime erode the clarity that makes that possible, and that needs to be factored into building a sustainable digital operation.

23. Too many potential recruits are in training for interviews & nothing else.

Hiring is by far the most difficult part of contemporary digital practice, and it has been hard all along. A complicating factor is that our goal-driven, immediate-gratification, immediate-access society has made it easy for motivated applicants to train for the interview, rather than for the job. Even with multiple interviews, it is difficult to understand the reality of a person’s skills, experience and aptitudes. Finding talented people out there is like trying to find a rare species in a rainforest—surrounded in all direction by animal mimics, butterflies that look like wolves, and lizards that look like leaves. People have become too good at simulating other idealized people, and employers need to actually observe them doing work, solving problems, and interacting with others in real time to find out who they really are and how they perform. This phenomenon has intensified over the decades.

24. Don’t leave the advanced parts until the “next phase”—or they may never happen.

The range of digital capabilities is exploding, but many organizations have deep, deep infrastructural issues in their digital operations that threaten to eat up all the existing time and budget. These problems result in a situation where organizations are often deeply attracted to emerging areas like personalized content, targeted experience, multichannel user tracking, and advanced content marketing, but they are in danger of never getting to it. Part of the art of the possible is to balance these different imperatives, and a responsible modern firm helps their clients to accomplish both—avoiding a situation where the establishment of a baseline digital operation is at the expense of moving forward into the most promising new areas.

25. There is more randomness in opportunity than anyone wants to admit.

A final point, one that is as gnomic and hard to know what to do with as it is true. People are geniuses at retroactively crafting narratives from chaos, but the reality is, no one wants to admit how much pure randomness is involved in the development of business (or anything else one might care about). Meeting an individual person can generate years of activity; while a mistake can remove years of opportunity. It is both healthy and humbling to keep all of this in mind when one is trying to understand variables like talent, success, and even large-scale trends. The journey of any venture is an aggregate of filtered chaos.

Many of the points above might seem self-evident to some, but in some ways the main takeaway is that underlining these insights would have made a remarkable difference had they been understood 10 or 20 years earlier. Will they be of any use to anyone else in the coming years and new situations that unroll before us? Who knows? I’m too much of a skeptic to believe even my own best advice, but I certainly hope someone does! Here’s to the next 25 years at TBG!

About the Author

John Berndt

I'm CEO of TBG and I've been thinking about the Web in creative ways since the year it began.

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