Technology + Management + Innovation

The Sisyphean Challenge of Senior Technology Leadership

by Jake Bennett

Technology managers find themselves between a rock and a hard place, forced to choose between focusing on technical depth or leadership excellence. A potential solution comes from an unlikely source.

Sisyphus pushing a rock up a hill

A workplace dynamic I’ve always found fascinating is the instinctual need for people to size up the technical depth of a technology leader upon first introduction. The hands-on technologists in the room want to determine if the manager understands what they do on a day-to-day basis. The non-technical people want to asses if she’ll be able to communicate clearly, or if she speaks in technical gibberish.

This social dynamic is a natural side effect of the dual nature of the senior technology leadership role. On the one hand, technology managers must create and operate code and infrastructure, which requires detailed, technical knowledge. On the other hand, they must translate technical concepts into business strategy and manage a team, which requires communication and leadership skills.

The challenge for senior technology leaders is that we can’t do both perfectly. Therefore, the goal of the CTO and other senior technology leaders is to strike the right balance between technical depth and business leadership, based on the size and focus of the company. However, this is easier said that done.

Focusing on Technology Depth

As a technology leader, you can never be too technical. We rely on technology managers to make the right technical decisions and resolve technical problems quickly when they arise. The deeper their technical chops, the better they’ll be able perform these duties.

However, this mantra comes with a proviso. As a technology manager, you can never be too technical, provided however, that you spend sufficient time and focus on your leadership responsibilities, which are your first priority. And herein lies the paradox of senior technology leadership: to do your job well, you need to dive deep into the technology, but if you spend too much time diving deep into the technology, you’ll lose your ability to be an effective leader. So what’s a technology manager to do?


Seven Practical Technology Leadership Principles

by Jake Bennett

Being a great technologist requires very different skills than being a great technology leader. The key to making the transition is adopting the right mindset.

Super Hero Illustration

Technical managers are often promoted to their positions of leadership by rising through the ranks—more so than most other disciplines. This is a practical move considering that business decisions today increasingly hinge on the nuanced details of underlying technology. Technology leaders need to assess technical options, align recommendations with business requirements and communicate these decisions to non-technical stakeholders. If technology managers don’t understand the technology at a detailed level, it’s difficult for them to make the right call.

The challenge is that being a great engineer doesn’t automatically translate into being a great leader. Leadership—technical or otherwise—is not something one is born with; it is a skill that is developed over a lifetime. Unfortunately, many companies don’t have management training programs in place to cultivate leaders as they move up the org chart. And for those that do, these trainings are typically generic and conceptual. General management training is an important first step, but it is insufficient by itself to prepare technology leaders for the tactical challenges that await them on a day-to-day basis in their new role.

To help new technical managers through the transition from individual contributor to leader, I often work with them to adopt a new set of non-technical skills. Although everyone is different, I’ve found that the principles outlined below provide a strong foundation for becoming an effective technology leader—that is, one who is able lead a team, implement change and consistently achieve results.

1. Adopt a Business Mindset and Develop Empathy

As an individual contributor, it is acceptable to view technology through a purely engineering lens. You have the luxury of focusing on the “how” and not the “why.” This means that as a contributor, you can indulge in technology religion, propose solutions without regard to business impact, and leave it to management to sort out the practical considerations of the real world. When you become a leader, however, you no longer have this luxury. You are now “management.” This means you need to make decisions based on the messy realities of the business, which requires considering financial constraints, organizational culture, office politics, human foibles, and business results.

New managers often make the mistake of making the case for their initiatives in technical terms, rather than business terms, and they become frustrated when they fail to receive the proper support. They expect the business to instinctively adopt a technical perspective, instead of realizing that it’s their job to reframe their proposals from the standpoint of the business.

The best way to overcome this mistake is to take the time to understand the business metrics that the company cares about the most, and the pain points felt by other departments. This requires empathy—a critical skill for effective leadership. Technology managers should talk to their colleagues and listen to their challenges. They should unpack the key metrics of the business, and understand the forces that drive them. They must summon the quantitative and analytical skills they have developed as engineers and apply them toward a new set managerial problems. Once they have done this, then they can make their case as a business leader rather than a technologist, and they can start engaging in a constructive dialog with the business.



Eight Reasons Why Agile Motivates Project Teams

by Jake Bennett

Research proves what software developers already know: Agile projects are more fun and inspiring to work on. In this article, we review the science that explains why Agile fosters greater motivation.

Scrum Board

A few weeks ago, I finished conducting a series of video retrospectives with several POP team members who recently completed Agile/Scrum projects. The goal of these one-on-one interviews was to elicit the kinds of critical insights that can only be discovered through in-the-trenches experience. By video recording the conversations, it allowed me to quickly distribute these Agile learnings to the larger agency in easy-to-digest bites.

It was great listening to the team talk about their Scrum experiences, but what struck me the most was the universal belief among the people I talked to that Agile projects were more fun and motivating than Waterfall projects. I wouldn’t have considered this a pattern if the people I interviewed had all worked on the same project. But the team members I spoke with worked on a variety of different projects, ranging from e-commerce sites, to mobile apps, to frontend-focused work. Furthermore, the participants came from different departments, including design, development, project management and QA. Yet despite these differences, it was clear that everyone I talked to shared one thing in common: they all had a much higher level of satisfaction and motivation when working on Agile projects. So for me the big question was: Why? What was it about Agile that fostered greater motivation and better performance than a typical Waterfall project?

Money certainly didn’t have anything to do with it. None of the team members I spoke with were compensated any more or less based on their participation on an Agile project. But the fact that money wasn’t the answer didn’t come as a surprise. Decades of research has debunked the myth that money motivates employees, despite corporate America’s obsession with performance-based pay. So if not money then, what?

The truth is that there isn’t any one aspect of Scrum that increases motivation. But when you dig into the research behind employee motivation it becomes pretty clear that there are several aspects of Scrum that do. To better understand why, let’s dive into the research.

1. Setting Goals

One of the most powerful motivators for employees is simply setting clear goals. According to Stephen Robbins, professor and author of The Essentials of Organizational Behavior, the research is definitive—setting goals works: “Considerable evidence supports goal-setting theory. This theory states that intentions—expressed as goals—can be a major source of work motivation. We can say with a considerable degree of confidence that specific goals lead to increased performance; that difficult goals, when accepted, result in higher performance than easy goals; and that feedback leads to higher performance than no feedback.” Fortunately, we’ve already been told that setting actionable goals is good, which is why managers focus on goal-setting during the annual employee review process. But this isn’t enough. Clear and challenging project-based goals occur more frequently and are usually more tangible and satisfying than amorphous yearly career goals. So having employees work on Scrum projects throughout the year can help bolster morale in between the reviews.



Traditional Project Management is 100 Years Old. It’s Time to Upgrade.

by Jake Bennett

Project management as it’s practiced today is a throwback from the industrial revolution and it hinders innovation in today’s fast-paced, digitally-disruptive world. Agile project management is it’s logical successor, but managers need to embrace it as more than just a software methodology.

Gnatt Chart Screen

Don’t worry—we’ve all done it. If fact, most of us are still are doing it. Actually, most of us are doing it and still think it’s okay to do it.

 Part 3 in a 3 Part Series

  1. Is Your Company Operating from an Industrial-Era Playbook?
  2. Why Performance-Based Compensation Doesn’t Work
  3. Traditional Project Management Needs and Upgrade

No, I’m not talking about sneaking in a little TMZ while we’re at work. I’m talking about using Microsoft Project or Excel to make a project plan—something far worse for productivity than the worker time lost by following the latest celebrity break-ups.

Okay, I admit it: I use Microsoft Project Gantt charts at POP for planning small internal projects. And this isn’t really a problem because the time horizon for these projects is short, the complexity manageable, the impact of delays relatively minor, and the amount of uncertainty fairly limited. In short, it’s a simple tool for a simple problem.

But what happens when the project gets more complicated? When the environment in which the product operates is constantly changing? When deliverables are complex and require significant collaboration across teams and partners? When money is on the line and people’s careers hang in the balance? That’s when the Gantt chart starts to break down.

Under these stressful circumstances (which are the norm for many digital initiatives), it’s natural for our desire to exert control to increase, and with it, our desire to seek familiar artifacts that give us a feeling of control. When the going gets tough, the tough make project plans. Unfortunately, feeling in control and being in control aren’t the same thing. No doubt the ancient tribes who performed elaborate rituals to control the weather felt in-control, even though they weren’t.



Welcome to the 21st Century: Why Performance-Based Compensation Doesn’t Work Today

by Jake Bennett

The science is crystal clear: performance-based compensation hasn’t worked for decades. So why is business still addicted to it?



Almost all companies today have a compensation program for at least some employees based on performance. From CEOs who are awarded bonuses for hitting a target share price to bike messengers who are paid by the delivery, performance-based compensation is widespread today.

Part 2 in a 3 Part Series

  1. Is Your Company Operating from an Industrial-Era Playbook?
  2. Why Performance-Based Compensation Doesn’t Work
  3. Traditional Project Management Needs and Upgrade

Clearly, given the ubiquity of performance-based compensation, one would assume that a great of deal of research has been conducted to assess the efficacy of this model. Why would all of these smart business leaders follow practices that don’t work? That would be crazy. And if you made that assumption you would at least be partially correct: decades of research have been conducted to determine if performance-based compensation works. The problem is that, according to author Alfie Kohn writing for the Harvard Business Review, the research all confirms the opposite conclusion:

As for productivity, at least two dozen studies over the last three decades have conclusively shown that people who expect to receive a reward for completing a task or for doing that task successfully simply do not perform as well as those who expect no reward at all.

Huh? Say what? That doesn’t make intuitive sense. And what about the father of scientific management, Fredrick Taylor? Was he wrong about the motivation of piece rates? Actually, as it turns out, he wasn’t. Contemporary research supports his conclusion that performance-based compensation for piecemeal work increases productivity. The problem is that the tasks performed by modern day professionals are no longer piecemeal. We’re not in the 1900s anymore. Piece rates worked for industrial era factories when employees worked on simple products as they moved down the production line. And they also work for workers like bike messengers, who fulfill simple tasks. But most businesses today aren’t dealing with simple tasks. They are responsible for managing incredibly complex systems staffed with a highly educated workforce. So why would we think the same piece rate principle applies?

In fact, performance-based compensation for complex tasks actually reduces productivity. According Dr. Bernd Irlenbusch from the London School of Economics, in a 2009 study of 51 corporate pay-for-performance plans: “We find that financial incentives…can result in a negative impact on overall performance.”

Come again? But that makes no sense. Why would people perform worse when they are paid for their performance?



Is Your Company Unwittingly Operating from an Industrial-Era Playbook?

by Jake Bennett

Many core business practices commonplace today are rooted in techniques developed during the turn of the twentieth century and are hindering companies from staying competitive in a business environment characterized by extreme uncertainty.

A natural result of human evolution is the desire for man to establish control over the world around him. Ever since the earliest days of civilization, long before science, man conducted rituals to foretell the future and performed ceremonies to control the environment. Fortunately for us, we learned a thing or two along the way, developed science, and switched from rain dances to irrigation systems.

Part 1 in a 3 Part Series

  1. Is Your Company Operating from an Industrial-Era Playbook?
  2. Why Performance-Based Compensation Doesn’t Work
  3. Traditional Project Management Needs and Upgrade

In fact, we were so successful using science to control our world, it was only a matter of time before we applied scientific principles to business. In the early 1900s, management pioneers like Fredrick Taylor, Henri Fayol and Henry Gantt led the charge. Taylor, acknowledged as the father of scientific management, realized that factory workers became more productive when their compensation was tied to their output, and thus developed the concept of piece rates. Fayol, considered the father of modern business administration and project management, defined the five essential functions of project management:

  1. To forecast and plan
  2. To organize
  3. To command or direct
  4. To coordinate

Henry Gantt developed the famous Gantt chart, allowing plant supervisors to monitor factory production to determine if output was on schedule.

Oh, those were good days for management. The items being produced were relatively simple (as Henry Ford famously said, “Any customer can have a car painted any color that he wants so long as it is black”). The processes required to build products were fairly straightforward. And even though the workforce was not well educated, they were easy enough to control with new management techniques in place. But most importantly of all, technology advanced at a leisurely pace, and things didn’t change too quickly.

Sadly, those simple times are over. Today businesses are faced with a much trickier landscape:

Back Then Today
Products were simple and mechanically oriented. Products are highly complex and software oriented.
Work was piecemeal. Components could be developed independently. Work must be done in teams. Components are highly interconnected.
The workforce was largely uneducated. The workforce is highly educated.
Data collection was costly and limited Data collection is cheap and far reaching
Technical advancement happened slowly. The pace of technological change is insane. Entire business models become obsolete in a matter of years.

Despite these major and obvious differences, companies today are still employing many key practices created during the industrial era. These practices are based on long-held assumptions rooted in 1900s thinking:

  • Management knows what’s best for the company, while workers are merely self-interested actors
  • The activities of workers must be tightly controlled
  • The environment in which production occurs is relatively stable

We’ll explore two critical businesses practices–employee compensation and project management–to uncover our hidden industrial-era habits.


Never Ending Digital Disruption is the New Normal

by Jake Bennett

Technological change is increasing at a such crazy pace, the disrupters themselves are facing existential threats from new upstarts. How can established companies hope to compete in this new world of constant change?

The rate at which technology is advancing is increasing at an exponential rate.

At first glance, this is not new news. We all know that technology is changing quickly. The Internet came along and transformed the business landscape. Old guard companies like Blockbuster (est. 1985), Tower Records (est. 1960), Newsweek (est. 1933), Barnes & Noble (est. 1873) and Best Buy (est. 1966) got hammered. Then came the iPhone. The era of the smart phone began. Now, a new round of disruption is underway, threatening another wave a companies. But who is in the cross hairs now? How about these “old school” companies:

  • Zynga (est. 2007) – The premier social gaming company was a Wall Street darling as recently as 2012. Now it is facing steep revenue declines and a plummeting stock price as users shift to mobile gaming.
  • Facebook (est. 2004) – Stumbling after its rocky IPO, Facebook made some huge defensive purchases (Instagram for $1 Billion, Occulus VR for $2 Billion, WhatsApp for $19 Billion) to combat the tide of users migrating from desktop to mobile. The strategy seems to be working for now. Investors delighted in seeing 62% of Facebook revenue coming from mobile in the Q2 2014 earnings report.
  • Apple iTunes (est. 2001) – The arch disrupter who pioneered downloadable music, is itself undergoing an existential disruption as people move from purchasing music to subscribing to it. Apple’s purchase of Beat’s Electronics for $3 Billion—which included the Beats Music subscription business—was an expensive hedge against the changing trend.

What’s particularly disconcerting about this recent wave of technological change, however, is the lifespan of the businesses being disrupted. The Internet decimated companies whose lifespans were measured in centuries and half-centuries. This latest round of change, in contrast, is disrupting businesses whose lifespans are measured in decades and half-decades. The upstarts themselves are facing existential threats only a few years after inception. Scary.

And if the innovators are born with an expiration date, how can established businesses ever hope to compete in this crazy new death match? If you are a retailer, and have seen the carnage caused by digital disruption, you are probably asking yourself: How can I remain competitive against the innovation engines of companies like Amazon, Gilt, Zappos,Square Space, Wanelo and Polyvore? Does it require rolling the dice on billion dollar acquisitions?

I don’t think it does. But it does requires a shift in mindset. For starters, companies need to stop using a playbook developed at the turn of the Twentieth Century.