Brandon Whelply wearing a suit with his hands folded and partially covering his face

How does an engineer become a business leader? More importantly, how do we enable today’s technologists to become tomorrow’s leaders?

Photos by Louis Tinsley
Cracking the Silicon Ceiling
by Brandon Whelply

ow does an engineer become a business leader? More importantly, how do we enable today’s technologists to become tomorrow’s leaders?

Engineering, at its core, is just using the context of technology to solve business challenges. It’s a craft that can’t be perfected and requires practitioners to continually educate, and reeducate, themselves to find the newest and most efficient ways to solve complicated problems. The language of engineering is robust, and the team collaboration is extremely nuanced. The engineering community has revolutionized business processes and redefined the way we think about incremental product development. All that said, why don’t we see more members of the technology community represented in the ranks of senior leadership in business? Aren’t innovation, problem-solving, diligence, collaboration skills, discipline, and process improvement supposed to be some of the most cherished traits in business leadership?

I began my career in the technology service industry in 2006, at the bottom of the consulting food chain, as a junior Java developer. I have spent significant time on seemingly every rung of the ladder between junior developer and VP. I’ve worked at big companies, mid-sized, and startups. I’ve written code, designed complex architectures, led large programs, balanced department budgets, hired, fired, and marketed services on countless sales calls. But when I reflect on my journey, one thing remains as true today as it was seventeen years ago: There is still no well-beaten path to the executive ranks when you begin as a technologist.

I believe the root cause of this challenge resides in a handful of institutional, educational, and social factors observed in the majority of workplaces.

The Pitfalls of Siloing

There’s a career ceiling in tech somewhere around the architect level where you can move no further without understanding many peripheral elements of business operations. Because traditional, non-tech business units are normally codependent on other groups, they allow for more horizontal visibility. For example, marketing generally collaborates with sales, accounting and finance work together, legal has optics on contracts, HR and recruiting depend on one another. You get the point.

I believe the nature of these more traditional roles allow for intuitive career mobility and provide high-level context on how decisions are being made outside of an employee’s purview. Engineering business units, however, tend to operate in a black hole. Normally one or two people speak on behalf of an entire engineering business unit, and senior stakeholders often treat teams like an expensive black box where problems go in one side and technical solutions pop out the other. In other words, generally engineers are only exposed to other engineers.

I spent the first seven years of my career with zero exposure to business units that were not technical in nature. It wasn’t until I was a program manager, about eight years into my career, that I first glanced at a budget, reviewed a statement of work, or had a conversation related to a prospective sale or expansion. I think we’re doing ourselves a huge disservice by siloing the rank and file at tech firms from basic PnL concepts simply because it’s not necessary. I believe the context is incredibly important. It helps technologists understand their role in the larger business ecosystem.

(De)Emphasis on Communication Skills

Between my undergraduate education in computer science and time spent as a developer, I spent nearly a decade in computing learning next to nothing about effective communication in a business environment. My first six months in a project management role were a huge struggle. I had no practice in effectively communicating with my team, clients, and supervisors. It took months of humble on-the-job learning until my communication skills caught up to the baseline expectations of the role.

Upon reflection, I’ve reached one conclusion: Business communication skills are the most under-trained and undervalued skills among engineers. Emphasis on business because engineers are, by trade, outstanding communicators in their own way—think whiteboards, diagramming, peer reviews, etc. Unfortunately, we’ve educated and reinforced generations of technologists to value only their contributions behind the keyboard and armed few with the skills needed to be successful standing in front of the room.

Subsequently, I still invest a great deal of time and effort to improve my business communication skills even after a decade of managerial experience because I believe I started out so far behind the curve. Worse yet, the big-picture result of this deemphasis on business communication has created a very real language barrier between leadership and its engineering teams since few people can translate business needs into tech speak and vice versa.

Culture and Perception
I could dedicate the entire article to this topic, but I’ll keep it brief. There are well-established and antiquated biases which make it hard for many executives and senior leaders to envision technology contributors in leadership roles. Listed are some real quotes I’ve heard past CXOs say in staffing discussions:

“Don’t you think [he/she] is a little too ‘hands-on-keyboard’ to be interacting directly with clients?”

“No. This program manager needs to be more buttoned-down than [long-time development manager].”

or my favorite:

“Developers don’t want to be project managers.”

When these stigmas are applied in the workplace, they create unnecessary boundaries built around imagined limitations.

Brass Tax
I can’t tell you how many times I’ve seen technologists miss opportunities because their teams were so dependent on them. Good engineers are extremely hard to come by and promotions require replacements. Moreover, there is very little incentive to move a high-performing (and profitable) engineer out of their current role and into something that’s more managerial or business-aligned. It introduces multiple risks: First, the engineering team may be less productive or suffer from a quality drop-off after losing one of their top performers. Second, there’s no assurance that the engineer will be able to perform the duties of his or her new role.

This all brings us to the billion-dollar question: How do we improve and plow through these roadblocks? It starts with us, the leadership. Since I don’t believe we can unilaterally alter industry-wide systems, processes, and perceptions, let’s explore some ways we can enable talent to be successful in this complex professional/social ecosystem.

Brandon Whelply standing by street with cars and business in background
Upon reflection, I’ve reached one conclusion: Business communication skills are the most under-trained and undervalued skills among engineers. Emphasis on business because engineers are, by trade, outstanding communicators in their own way—think whiteboards, diagramming, peer reviews, etc.
Discuss Careers Openly and Broadly

Most of the time when I ask an engineer where they want to take their career, I get one of three responses: architect, lead, or “I’m fine where I’m at.” In fairness, all three are terrific options, but I’ve heard these answers so many times I don’t believe many engineers know they have other options. As leaders, it is important that we invest in our employees’ career paths. For example, you already know they can code, so figure out where their top soft skills reside. Are they social? Impressively analytical? Insanely quick learners? Understanding their skills allows you to plant seeds of how they could be valuable in other spaces. At minimum, show them that their world is bigger than just architect, lead, or “doing just fine.” Whether it be in sales, finance, delivery management, or something else, a strong technical background can be a massive differentiator from other peers in the field. Seriously, just imagine a world where all tech sales executives were actual technologists by trade. I’m not saying it would bring forth world peace, but it could.

Lastly, let’s stop being shy about business communication skills. When you’re providing feedback to an employee regarding performance, it’s okay to ask them to work on their communication skills the same way you would ask them to improve on a given technical discipline. Be non-judgmental in tone, provide specifics, and be prepared to help. A lot of people just need a nudge to get started down a better path. Recently I had a former employee thank me for advice I gave him a few years ago regarding his communication skills. In this employee’s case, he would occasionally sound robotic and uncertain when reporting progress updates to executives because he was trying too hard to dress up the language and use fancy words. My advice to him was to keep the ten-cent words in his back pocket and try to say more with less. This coaching moment lasted maybe ten seconds, but according to him it was instrumental in shaping the way he communicated with others moving forward.

Make Talent Replaceable

One of the best pieces of professional advice I have ever received is that a good leaders make themselves replaceable. In other words, if you move on from your role, you should ensure that at least one person is capable of performing your duties. After all, if you can’t be replaced then you’ll never get promoted. You’re just creating a log jam for yourself and everyone in line behind you. This becomes especially important in the technical ecosystem. All too often teams will have one or two high-performers that function as the go-to resource for just about everything. Perform succession planning and emphasize cross-training your team by asking people to step out of their comfort zone and perform some of the duties normally done by said high performers.

Take Mentorship Seriously
Technology suffers from a terrible shortage of dedicated mentors. Probably because mentorship requires a lot of time, which we don’t have, and patience, which is all too often worn thin. Even worse, there’s little business incentive: mentorship doesn’t directly generate revenue and is seldom recognized. Nonetheless, we all need to commit to being good citizens of the technology community and play our part in helping the willing develop the skills we all had to learn the hard way. Engage with protégés personally and empathetically; stop being a boss and start being a coach. Be a true volunteer. Few things in my career have been more personally rewarding than helping people ascend to their true potential in the workplace, and when I think back on it, probably 90 percent of the guidance I’ve provided to past protégés has been related to soft skill practices such as dealing with difficult personalities and negotiating complicated political situations. Let the gurus on Stack Overflow and YouTube grow their technical skills and save your counsel for the lessons learned outside of books and internet forums.

Facilitation of mentorship is vital as well. I’m constantly on the hunt for senior employees willing and able to mentor. When I find these people, I immediately work to find them a more junior “buddy.” I’m not working to create a formalized mentorship framework or drive any sort of agenda on what mentorship should be within the context of our business. I just connect people who stand to benefit from one another and let them form their own mentor-mentee relationship organically.

Be a true volunteer. Few things in my career have been more personally rewarding than helping people ascend to their true potential in the workplace…
In closing, I’d like to challenge readers to spend time thinking about the benefits of investing in the career growth of the talent-rich pool of innovators and problem solvers at their company. Could it help better align sales and delivery? Save money? Better inform leadership? Increase time to market? Improve communication? Prevent contracts with poor vendors?

I believe the answer to all these questions is “yes,” but first we’ll need to find ways to close the knowledge gaps between traditional business units and technology teams so we can capably position the technically adept as decision makers.

Brandon Whelply headshot
Brandon Whelply is a career technology professional with seventeen years of experience in the technology services industry. Specializing in enterprise data integration, cloud infrastructure, and DevOps, he has developed, designed, overseen delivery, and built digital services practices supporting over 100 public and private sector clients. He is currently the vice president of technology at Apisero (a recent NTT Data acquisition) focused on aligning with Apisero clients to ensure they realize their technical visions.