Why Don't We Mentor Software Management?

Why Engineering Management Fails Us

In recent years, companies have seen a significant impact from neglecting manager mentorship. For example, a survey found that organizations lacking effective leadership programs had a turnover rate nearly 30% higher than those with robust training initiatives. Moreover, failed projects cost businesses millions, underscoring the urgent need for improved leadership development. (Project Management Institute, 2022). This article addresses a core challenge in engineering management, spanning all levels and titles: we do not adequately mentor or prepare leaders to succeed. While I use the general term "management" throughout, the crucial question is whether we equip anyone assuming leadership, from manager to vice president, with the support and skills for true leadership impact. Crucially, executive decisions and priorities play a defining role in shaping the mentorship culture within organizations. (Reeves, 2024). Executives must recognize their direct influence and accountability in fostering an environment that prioritizes the development of leaders. By aligning their strategies and expectations with this goal, they can ensure the cultivation of effective mentors and robust leadership at all levels.

We often assume management naturally grasps leadership, having risen through company ranks. Directors and vice presidents—those leading managers—are often promoted for reasons unrelated to team-building or leadership ability. Some excelled as individual contributors; others were promoted to fill vacancies, or chose for their strong opinions or polished interview skills. The selection process often prioritizes superficial qualities over team-building and leadership skills—the qualities that truly impact organizations.

Upper management expects new managers to deliver results and reach set goals. Management must help their teams perform at their best, ensuring the right people are in the right roles at the right time. The focus is on matching skills and experience to advance effectively. But is the difference between leading and managing—crucial for success—always clear to new managers? Consider two examples: Sam, an individual contributor who climbed the ranks through outstanding technical skills, struggled to transition into his new leadership role. He continued to focus on his tasks, failing to inspire his team or create a cohesive vision. Meanwhile, Alex, another individual contributor who was mentored upon promotion, understood the nuances of leadership. She actively engaged with her team to build trust and guide them through challenges, resulting in a more motivated and high-performing group. These contrasting vignettes highlight the significance of mentorship in cultivating genuine leadership skills.

Surface-Level Management vs. Real Leadership

Managing is not intuitive, nor learned by proximity. Most new managers lack a model, guidance, or feedback. They inherit responsibilities without a clear understanding of what "good" looks like, thereby undermining their ability to lead. Management is not mere oversight—it is shaping direction, building clarity, and fostering resilience. Without mentorship, these fundamentals are neglected, and management effectiveness suffers.

Mentorship and Explicit Teaching

We train engineers, designers, and sales reps. For managers? HR compliance training, then left to sink or swim. Problems soon appear: misaligned teams, stalled careers, unclear priorities, culture drift, and attrition. Not from lack of care, but from never being taught how to manage. The real challenge is handling the many scenarios that come with leading people, products, and organizations—not just tasks. The system turns out coordinators, not real leaders.

Too often, coordinators focus on surface-level work, such as task trackers, definitions of "done," and one-on-one schedules. While these tools assist, they are not the core of the work. This distinction is crucial as we consider how management's reliance on process impacts leadership. When management uses tools as a substitute for vision or philosophy, they become masters of ceremony, facilitating activity without shaping direction. The result is motion without meaning, leadership as ritual, not substance.

Effective management is not accidental; it is developed through mentorship and constructive feedback. Management needs intentional development—space to think, support to grow, and clear examples to follow. Teaching the fundamentals and not assuming prior knowledge is essential. Mentorship and explicit instruction are essential for achieving management success.

To address this, consider conducting a quick self-audit to evaluate a recent meeting. Reflect on whether it was more ceremony or impact-driven. This simple exercise can reveal hidden tendencies to prioritize process over meaningful results, encouraging self-reflection without demanding much time.

When we invest in management, teams become stronger, systems more resilient, and urgent issues less common. This investment in management development yields measurable business outcomes, including improved employee retention, enhanced innovation, and improved financial performance. By fostering a culture that nurtures leadership skills, organizations can reduce turnover rates, stimulate innovative solutions, and achieve higher profitability. (Psicosmart Editorial Team, 2024). In contrast, neglecting management leads to compounding dysfunction. Without targeted guidance, management does not self-correct, plateaus quickly, and their teams pay the price. The key takeaway is clear: management development is crucial for team and organizational health.

Real Leadership

Suzy Welch said, "If you're a manager or a leader and all you do is dream big dreams and talk about the future in lofty visionary terms and you don't actually get anything done, everyone is going to hate you.”

Welch adds that management's job is to move between the why and the how—sometimes in one conversation, always in the same day. Effective managers balance vision with execution.

Many managers act as messengers, relaying "This is what the team says," or taking the message back to teams: "This is what upper management says," while remaining neutral. They fail to help both sides understand each other. Upper management doesn’t know what’s needed or why. Teams don’t understand upper management’s concerns or why they’re pulled in different directions. I’ve personally experienced this with my leaders, and it ended with incorrect assumptions, poor perceptions, knee-jerk reactions, and people being fired.

Welch cautions against neutrality in management. "The worst thing in the world is a fingerprintless [manager]. Leave no sign of what you really believe. Everybody comes to resent that. You sort of agree with the last person in the room. You've got to have conviction," (Welch, 2025).

The Leadership Shortcut Myth

Compounding the problem, software often places non-technical management over highly technical teams. We wouldn’t put someone with no finance background in charge of accounting. We wouldn’t put someone with no medical training in charge of surgeons. Yet in software, this is common. This disconnect introduces new risks, especially as technical complexity is reduced to delivery tracking. Engineering becomes a black box. Critical decisions are made without context, leaving the team to explain fundamentals to someone who lacks the language. The effect is predictable: decisions slow down, trust erodes, and the team learns to lower expectations. The risks become deeply personal when you experience them firsthand. I watched a new vice president, who had never worked in the company and had only consulted on security for other organizations, step in and dictate a wholesale change to our core database technology. There was no clear benefit outlined—only assumptions and personal conviction. The cost? Millions of dollars, years to implement, and a tremendous disruption to teams who had spent years building around the existing foundation. This wasn’t just a technical misstep; it was a decision that eroded trust, undermined the expertise of those who knew the system best, and ultimately offered no meaningful return—if not a negative one. When ego and inexperience drive critical choices, everyone pays the price, and the team sees firsthand how quickly trust and momentum can be lost.

Why Do Experienced People Get Overlooked?

Why is it that those who have spent years developing their craft within engineering are often overlooked for promotion in favor of those from other backgrounds and even other companies? Not only individual contributors, but also management are overlooked. Even when individuals have invested the time, gained in-depth domain expertise, and are well-liked, they can still be passed over for leadership roles. These patterns prompt questions about how organizations perceive and promote talent. Sometimes, organizations mistake familiarity with tools or processes for readiness to lead, or they prioritize polished communication over the patient accumulation of experience. In other cases, individuals who have mastered the functional aspects of management get labeled as "managers," while others—sometimes with less direct experience—are seen as "leaders." What sets these groups apart? And why do many qualified individuals remain stuck, despite their contributions and commitment?

It often comes down to perception and narrative. Some are called leaders because they inspire, share a clear vision, or steer through ambiguity, no matter their background. Others, despite technical skill, are seen as managers who keep things running. Leadership and management aren’t mutually exclusive, but organizations often confuse them, missing opportunities to develop both. For experienced staff, a lack of mentorship and clear growth paths gets in the way—not their ability. This is why teaching and mentorship matter: they turn expertise into visible leadership, ensuring experience is valued, not overlooked.

The Real Risks of Shallow Technical Leadership

Throughout my career, I have worked with many leaders who came from non-technical backgrounds. Some were promoted simply because a more fitting position wasn’t available, and while their knowledge of the business side was valuable, their experience in software product development was limited. One individual, for example, had transitioned from a finance role to vice president of engineering in just a year. They were a quick study, eager to learn, and their work ethic was second to none—qualities that earned them respect and advancement. However, even with strong aptitude and dedication, there is no shortcut to mastering a discipline as complex as software leadership, which can take over a decade to truly understand. As a result, even the most capable individuals often need to rely heavily on the expertise of those around them, echoing the perspectives of their managers and architects. This isn’t a failure on their part, but rather a reflection of the depth and time required to develop real fluency in a new domain. So, what does this mean if deep understanding cannot be accelerated? Are we equipping and promoting the right people to lead technical teams, or are we asking too much, too soon?

Organizational Structure

At the manager level, the common failure is mistaking activity for leadership. They focus on tickets closed, meetings held, and ceremonies executed. However, without mentorship, they lack the skills to coach, guide, or align their work with a broader perspective. They are pushers and are likely to become micromanagers. They spend all their time telling team members to do more work more quickly. They never get out of the trenches, climb a hill, and fully flesh out what they are asking the team to accomplish. The result: teams work hard but don’t always work on what matters.

At the director level, the problem shifts. Directors manage managers, yet many never learn to build managers into leaders. When directors step up, they become force multipliers, translating company strategy into actionable and inspiring goals, empowering managers, and removing organizational roadblocks. They champion product and customer outcomes, building a healthy and sustainable culture by modeling trust, transparency, and collaboration.

When directors fail to fulfill these responsibilities, the effects ripple throughout the organization. Misalignment and confusion set in as teams lack a clear vision or priorities. The leadership pipeline stagnates because managers and leaders don’t receive adequate growth opportunities. Persistent bottlenecks and cross-team issues go unresolved. Teams focus on output, not outcomes, and engineering is measured by velocity rather than customer value. Culture erodes, burnout increases, and top talent disengages or leaves.

The difference is not subtle—great directors provide clarity, remove friction, and grow leaders. When they do not, teams drift, delivery stalls, and the best performers look elsewhere. The impact is felt in every product launch, every customer interaction, and every stand-up meeting.

At the vice president level, the gap becomes strategic. VPs must align engineering with the business, translating the company’s mission into a compelling and actionable technology vision. When VPs get this right, they excite and unite the organization, architecting a structure that scales, anticipating growth needs, and ensuring the right leaders are in place. They champion a culture of accountability, trust, and learning, and they act as the bridge between engineering and the rest of the executive team—advocating for engineering, negotiating priorities, and ensuring alignment with product, design, and business units. They invest in the next generation of leaders, mentoring directors and building a healthy succession pipeline.

But when VPs lack the technical depth to understand tradeoffs or the leadership grounding to articulate and reinforce a clear vision, everything downstream suffers. This strategic misalignment leads to fractured director focus, which in turn produces tactical, short-sighted managers. The end result is disengaged teams and a culture where process is prioritized over product excellence. VPs who fail to mentor directors or model what great leadership looks like allow weak fundamentals to cascade through the organization. Instead of being true stewards of engineering and culture, they become process operators—reactive, focused on reporting and status rather than impact and growth. The belief that their role is only "big picture" is a trap; VPs must actively shape both strategy and the leaders who execute it. When this does not happen, trust erodes, the management chain stagnates, and the entire organization feels the pain—from missed opportunities to the slow loss of top talent.

Measuring What Matters

We give new managers a team, a dashboard, a roadmap, and meetings, expecting them to transform culture and drive execution. But we rarely offer real mentorship or guidance. To bridge this gap, organizations could implement structured mentorship initiatives that include pairing new managers with seasoned leaders for regular mentoring sessions. Additionally, executives could champion specific programs such as leadership workshops and peer-led learning circles, encouraging managers to exchange experiences and learn from one another. If we want impactful management, how do we measure it—and are we preparing leaders for the job?

Function-based measurement is most common. These methods—tracking tasks on Kanban boards or similar systems—measure planned, current, and completed work. SCRUM, Safe, and other tracking systems have been used for decades. Still, none of these indicate whether our work makes an impact or how we should change. Think of the success stories you’ve read, and none of them state, in effect, “Once we loaded up on ceremonies, bureaucracy, and process, we found outlandish success.” No, the success stories read, “Once we removed ceremonies and processes and started collaborating on delivering what mattered, we found outlandish success.”

Measuring outcomes isn’t as straightforward as tracking tasks or hitting milestones. Sometimes you follow the plan exactly and still miss the mark—other times you deviate from the plan but achieve the right result. Which scenario is preferable? The first shows disciplined execution without true impact; the second, impact without a repeatable process. The real challenge is to build teams and systems that can deliver meaningful outcomes consistently, learning from both successes and failures. Outcome-based measurement pushes managers to look past busywork and ask: Did we actually move the needle for our customers and our business?

If you want to know if your team is winning, look beyond the to-do list. Internally, real success shows up in fewer bugs, faster recovery, fresh ideas, and driving innovation. It also shows up in non-technical ways, including a team that’s engaged, sticks around, actually learns from one another, and has the ability to collaborate across functions. Effective engineering managers foster a culture where teams deliver value, adapt quickly, and support one another’s growth. (Zuber, 2021)

External (customer-focused) measurements emphasize the real impact a team’s work has in the world, including improved user satisfaction, higher adoption rates, faster time-to-value for new features, and positive feedback from end-users. Both technical and non-technical measures matter, from the quality of released software to the trust and loyalty built with customers. Together, these metrics provide a holistic picture of whether a team is not just busy, but truly effective—delivering meaningful results for the organization and those it serves.

It’s common to hear management express concerns like, “We aren’t moving fast enough,” “the quality isn’t there,” or “we need to do more.” Yet behind these statements often lies a lack of clarity about the underlying issues and a gap in actionable solutions. These frustrations may indicate problems with team effectiveness, product quality, or customer impact, but without specific, meaningful measurements, it’s challenging to pinpoint what’s truly holding the team back. Instead of merely voicing dissatisfaction, effective managers work to identify the root causes, whether technical or non-technical, and use targeted, holistic metrics to guide improvement. The challenge is not just to recognize that something feels off, but to make the invisible visible, turning vague frustrations into focused strategies for success.

Leading for Real Impact

Management is not a simple job. It is not about telling someone what to do or giving a vision and then following up on when they will complete it. It’s about being able to do both. Going from a big idea to a small task and back again. Middle management too often gets stuck in the middle ground. They are messengers who are neutral. As Welch puts it, “When you’re a messenger, you sort of drop the bomb. ...And then you sort of stand there and you act like Switzerland. You’re neutral. You’ve got to have conviction,” (Welch, 2025)

Mentorship is not a nicety, but rather a missing discipline in management. By failing to provide structured mentorship, organizations hinder the leadership development of directors and vice presidents, who are then unable to train the next layer. This perpetuates stagnation at all levels—the core argument being that true leadership cannot develop in a system that neglects mentorship.

Management are multipliers. But only if we teach them how. Without that teaching, they remain custodians of process rather than builders of culture and direction. To unlock real management impact, prioritize and invest in effective mentorship now.

References

Project Management Institute. (2022). Pulse of the Profession: Success Rates Rise: Transforming the High Cost of Low Performance. https://www.pmi.org

Reeves, M. (2024, February 14). Mentoring for Success: Strategies for Organizational Growth. https://www.togetherplatform.com/blog/mentoring-for-success-strategies-for-organizational-growth

Zuber, I. (2021). Inside Our Engineering Mentorship Program and How It Helps Our Engineers Grow. https://buffer.com/resources/engineering-mentorship/

Psicosmart Editorial Team. (2024, August 28). How can mentoring programs enhance leadership development within organizations? (n.d.). Psicosmart.pro. https://blogs.psicosmart.pro/blog-how-can-mentoring-programs-enhance-leadership-development-within-organizations-87000

Browning, J. (2025). The Rise of the Lanager: Why Leadership and Management Can’t be Split. Retrieved from https://bigthink.com/plus/the-rise-of-the-lanager-why-leadership-and-management-cant-be-split/

Welch, S. (2025). Why Having a Vision Isn’t Enough to Be an Effective Leader. Retrieved from https://youtu.be/23hhZbvFoBs?feature=shared