How Leaders Fail Their Teams

I’ve written before about the multitude of ways that teams end up failing themselves.

In The Math of Mediocrity, I explored how we temper our expectations of excellence when our wildest ideas and imagination meet the molasses of reality.

In The Dichotomy of Change Control and Quality Software, I touch on how processes designed to instill quality ultimately backfire and cause us to create lower quality, less usable, “stale” software that can’t adapt to our users and to the market.

Those two posts were written 3 years apart across two different companies.  A decade later, I am still navigating how to address these issues in enterprises and startups alike.  I don’t think my prescribed path out of mediocrity and the dichotomy of change control and quality (or lack thereof) has changed, my understanding of why teams find such a hard time taking the steps necessary to do so has changed.  I still think that the answer is training, smart process, modular architecture and frameworks, and automation; these tools allow teams to build speed, work fast, and do so with high confidence in quality.  The question is why teams find it so hard to make the shift.

The answer is the people and the problem is what Sacha Golob describes as conceptual inadequacy in his essay The Politics of Stupidity:

Looking back at the trenches, one of Field Marshal Haig’s contemporaries, Ian Hamilton, remarked that Haig had understood the Somme as “halted mobile operations”. Hamilton’s point is that the framework Haig used to understand the Western Front was taken from the cavalry war of his youth – it was a “mobile operation”, with the tiny caveat that nothing budged for months.

Haig’s outmoded framework for warfare meant he lacked the conceptual resources to make sense of what was actually happening around him. Such an inability to understand is not the same as mere error. We make errors for all kinds of reasons: if, in haste, I misread my watch, the cause is simply impatience. Haig’s misjudgements, on the other hand, assuming that Hamilton’s diagnosis was right, proceeded from his lacking the right conceptual tools for the job. This conceptual inadequacy is, for me, a paradigm form of stupidity – and here, one with tragic consequences.

Such systematic failures of understanding are a stubborn problem. If the difficulty at the Somme had been laziness, that could have been easily fixed: there was no shortage of energetic generals. But if Haig worked himself to the bone within the intellectual prison of the 19th-century military tradition, then solving the problem becomes harder: one would need to introduce a new conceptual framework and establish a sense of identity around it and military pride in it.

Golob so succinctly describes the problem I have seen over and over again: people in leadership positions who don’t know what they don’t know.  These individuals are obviously competent and rarely “dumb”, but make seemingly puzzling decisions that put the brakes on progress.  Why?  Because such individuals are operating on a broken conceptual framework of their field of professional expertise.  Corporate career trajectories ultimately mean that the people in leadership positions with the authority to make decisions are usually the individuals most removed from the day-to-day work performed by any team they lead.  And this usually means that these individuals are usually the most out of touch with how technologies and ideas evolve.

In stale organizations, this becomes a limiter to growth; the egos and authority of these individuals start to oppress growth, change, and progress because such individuals are operating on an “outmoded framework” in their field; they see their past success as proof of their superior knowledge and understanding while ignoring the forward march of technology.  These days, it’s rare that 1 year old documentation is relevant (especially if you are working on cloud (and who isn’t?!?)).  The days of massive tomes are over; the technology simply evolves far too quickly for such channels of dissemination to be effective and efficient; such books would be dated by the time they reach the shelves!

Facebook has created Docusaurus and open sourced their documentation engine.  Microsoft’s open source DocFx tool is used to author their documentation, which itself is open sourced.  Amazon also open sourced AWS’s documentation.  The pace of change in knowledge is accelerating, which necessitates new approaches to capturing and sharing this information.

This image is from one of my favorite slides I have in one of my presentations:

In the 90’s, one could be a rockstar on your way to being a dot-com era millionaire knowing just a handful of technologies.  Even through 2010, being proficient in just a handful of technologies was sufficient to command a high salary in tech.  A strong grasp of SQL, DHTML, and C# or Java could easily land you a six-figure job.  But the world has changed and the pace of that change has accelerated.  In 10 years time, we’ve gone from enterprises running bare metal to virtual servers to containers and to “serverless” technologies in the last few years.  If we look at the technologies that will dominate the enterprise landscape in the next 5-10 years, it is no longer possible to be in the vanguard without adapting and constantly learning.

At Microsoft, I think this is the biggest change that Satya Nadella brought.  In an Inc. article, Justin Bariso writes:

It’s been almost five years since Satya Nadella became the third chief executive of Microsoft. When he took over, the company was in the midst of an identity crisis. Many felt Microsoft had become lethargic, content to ride a rapidly dissipating wave of success while competitors charged forward with new, innovative ideas.

But in those five years, Nadella has conducted a stunning turnaround. With increased efforts on attracting young talent and changing the “old guard” culture…

The article is titled This Is the Book That Inspired Microsoft’s Turnaround and that book is Carol Dweck’s Growth Mindset (recommended!) and this is the key: the ability and drive to continue to grow, inquire, introspect, and learn.  It is the ability to acknowledge that one does not know what one does not know, but the goal should be to have a growth mindset to seek that knowledge without an ego and without shame.  In fact, when I interview candidates, this is one of the most important characteristics I seek: if they do not know the answer, will they stop and say they do not know the answer?  A candidate that acknowledges what he or she does not know can be trained in that knowledge.  On the other hand, a candidate unwilling to concede what they do not know can never take the first step to learning.  I have touched on this before in Effective Hiring for Small (or All) Teams; the candidates I value are those that have the potential for growth rather than the candidate that has embedded knowledge (ideally, the candidate has both!) because the landscape shifts so rapidly that embedded knowledge is outmoded if one cannot grow.

Coming back to Golob’s conceptual inadequacy, then, the answer is to shed one’s ego and shed one’s façade of expertise and constantly seek growth; rather than seeing shame in acknowledging a lack of knowledge, embrace this gap as an opportunity to grow and learn; Scott Hanselman is the poster boy for this mindset.  However, organizations need to find ways to foster this way of thinking and build incentive, compensation, and career advancement structures that reflect a focus on the ability to grow rather than the propensity to oppress.  Organizations need to see that lack of knowledge is not a failure, but the lack of drive to seek knowledge is the true failure.

As DeMarco and Lister write in Peopleware:

The propensity to lead without being given the authority to do so is what, in organizations, distinguishes people that can innovate and break free of the constraints that limit their competitors. Innovation is all about leadership, and leadership is all about innovation. The rarity of one is the direct result of the rarity of the other. (DeMarco, Lister, 2013)

Stale organizations confuse experience with leadership and use these ideas interchangeably.  What DeMarco and Lister propose is that leadership is the ability to innovate or foster innovation.  Leadership and innovation must go hand-in-hand and innovation can only flow from having a conceptual framework that is ready to meet new challenges.