Challenges in Engineering Management

As a Fractional CTO across many businesses over the years, here are some of the common issues I find in engineering organizations and tech stacks: 𝗟𝗮𝗰𝗸 𝗼𝗳 𝗔𝗹𝗶𝗴𝗻𝗺𝗲𝗻𝘁 𝗯𝗲𝘁𝘄𝗲𝗲𝗻 𝗕𝘂𝘀𝗶𝗻𝗲𝘀𝘀 𝗮𝗻𝗱 𝗧𝗲𝗰𝗵 𝗚𝗼𝗮𝗹𝘀 → Engineering teams are often working in silos. → Business objectives get lost in translation. 💡Solution: Regular syncs between engineering and business teams to ensure alignment. 𝗧𝗲𝗰𝗵𝗻𝗶𝗰𝗮𝗹 𝗗𝗲𝗯𝘁 𝗔𝗰𝗰𝘂𝗺𝘂𝗹𝗮𝘁𝗶𝗼𝗻 → Quick fixes and hacks lead to longterm issues. → Scaling becomes a nightmare due to accumulated debt. 💡Solution: Implement a strategy to pay down technical debt incrementally. 𝗜𝗻𝗮𝗱𝗲𝗾𝘂𝗮𝘁𝗲 𝗗𝗼𝗰𝘂𝗺𝗲𝗻𝘁𝗮𝘁𝗶𝗼𝗻 → New hires struggle to get up to speed. → Knowledge is often tribal and not formally captured. 💡Solution: Invest in comprehensive documentation from the getgo. 𝗢𝘃𝗲𝗿𝗹𝘆 𝗖𝗼𝗺𝗽𝗹𝗲𝘅 𝗔𝗿𝗰𝗵𝗶𝘁𝗲𝗰𝘁𝘂𝗿𝗲𝘀 → Engineers often overengineer solutions. → Complexity leads to more bugs and slower development. 💡Solution: Aim for simplicity and clarity in your tech stack. 𝗣𝗼𝗼𝗿 𝗖𝗼𝗺𝗺𝘂𝗻𝗶𝗰𝗮𝘁𝗶𝗼𝗻 𝗖𝗵𝗮𝗻𝗻𝗲𝗹𝘀 → Teams often rely on inefficient methods for updates. → Important information gets lost or delayed. 💡Solution: Encourage sharing information early and often (and reward people for raising issues versus shooting the messenger). 𝗜𝗻𝘀𝘂𝗳𝗳𝗶𝗰𝗶𝗲𝗻𝘁 𝗧𝗲𝘀𝘁𝗶𝗻𝗴 𝗮𝗻𝗱 𝗤𝗔 → Bugs make it to production far too often. → Customer experience suffers as a result. 💡Solution: Invest in QA automation tools and build your tests to run automatically once versus manually testing everything with your QA team and Dev team every release. 𝗟𝗮𝗰𝗸 𝗼𝗳 𝗖𝗼𝗻𝘁𝗶𝗻𝘂𝗼𝘂𝘀 𝗟𝗲𝗮𝗿𝗻𝗶𝗻𝗴 → Tech evolves rapidly, but teams often don't. → Skills and knowledge become outdated quickly. 💡Solution: Foster a culture of continuous learning and improvement. 𝗜𝗻𝗳𝗹𝗲𝘅𝗶𝗯𝗹𝗲 𝗧𝗲𝗰𝗵 𝗦𝘁𝗮𝗰𝗸𝘀 → Older technologies often hinder innovation. → Migration to new stacks is seen as too disruptive. 💡Solution: Plan for gradual migration to more flexible technologies. 𝗦𝗲𝗰𝘂𝗿𝗶𝘁𝘆 𝗢𝘃𝗲𝗿𝘀𝗶𝗴𝗵𝘁𝘀 → Security is often an afterthought. → Vulnerabilities can lead to significant business risks. 💡Solution: Make security a foundational aspect of your development lifecycle and build it into your deployment pipeline. 𝗥𝗲𝘀𝗼𝘂𝗿𝗰𝗲 𝗖𝗼𝗻𝘀𝘁𝗿𝗮𝗶𝗻𝘁𝘀 → Teams are often under resourced. → Leads to burnout and turnover. 💡Solution: Track metrics like team velocity and apply pragmatism to workload assigned each sprint or development cycle. These issues are common but solvable. What challenges have you faced in your engineering organization? Let’s discuss!

As an advisor to tech scaleups, and a former CTO and SVP of Engineering,  I've often encountered a familiar CEO complaint: "Our engineering team is too slow!" However, focusing solely on increasing individual productivity is rarely the solution. Sometimes the answer is changing the organizational structure. 🔍 The Issue with Flat Structures: Time to market was a major problem in a scale-up I advised, even though they had a flat structure where 40+ engineers reported directly to the VP of engineering and all of them shared equal accountability to the delivery of the software. 🚧 The Consequences: Major overcommitment.  People raised their hands to take on work even if the group was super extended. There was nobody that fully understood the team’s capacity vs the actual workload they took on. This approach led to a lack of predictability, chronic delays, unhappy customers, and ultimately, a tarnished reputation. 🛠️ The Solution: Transitioning to a hierarchical structure with focused teams and accountable experienced leaders was the game-changer. This shift brought in clarity, accountability, and much-needed structure. 📈 The Results: Predictable schedules, improved customer satisfaction, and a thriving engineering culture. ✅ Takeaways for Your Organization: Examine your organization with critical eyes: Is your ownership and accountability structure clear? Are your teams sized and focused appropriately? Do your leaders have the authority to deliver effectively? For more on the case study and about building a sustainable, efficient, and customer-centric engineering team in the blog post. 💭 I'm curious to hear your thoughts: Have you faced similar challenges? How did you address them? Let's share insights and grow together! #EngineeringManagement #Leadership #Productivity  _______________ ➡️ I am Talila Millman, a fractional CTO,  a management advisor, and a leadership coach. I help CEOs and their C-suite grow profit and scale through optimal Product portfolio and an operating system for Product Management and Engineering excellence.  📘 My book The TRIUMPH Framework: 7 Steps to Leading Organizational Transformation will be published in Spring 2024 https://lnkd.in/eVYGkz-e

🚀 New Financial Year, New Challenges The start of a new financial year brings fresh expectations, new goals, and, of course, new hurdles. With AI evolving rapidly, it won’t be long before data-driven insights help us stay on track and make informed decisions. As teams and individuals are empowered to perform better and faster, it raises the big question: What does growth really mean for a company❓ As companies scale, engineering challenges evolve. What works with 30 engineers won’t work with 100, and what works with 100 often breaks at 1,000. I remember leading a small startup, moving fast like a Formula 1 pit crew —ideas to production in a day 🏎️. But as we grew, got acquired, and went public, we had to adjust and adopt new approaches to keep up. Challenges at Different Stages - 📃 Small Companies (30-100 Engineers) : The biggest hurdle here is often lack of clarity—constantly shifting priorities, unclear requirements, and a lack of established processes. 📑 Mid-Market Companies (100-300 Engineers) : At this stage, the focus shifts to talent acquisition and retention, scaling leadership, operational efficiency, and tech integration. 📚 Enterprise Companies (300+ Engineers) : For large organizations, visibility becomes crucial. Bureaucratic hurdles, lack of data visibility, and process bottlenecks are common issues that slow down progress. How to Overcome These Challenges 💡 1) For Small Companies - Set clear quarterly goals using frameworks like OKRs to ensure alignment. Use structured processes like user stories and product backlogs to clarify and align requirements. Foster collaboration through lightweight agile workflows, ensuring adaptability—like a jazz band where everyone plays their part 🎛️ 2) For Mid-Market Companies - Hiring fast without proper onboarding is a costly mistake. Recognize burnout risks and manage attrition effectively. Invest in leadership development, mentorship, and use data analytics to track efficiency. Make sure everything works like a well-oiled machine ⚙️ 3) For Enterprise Companies - Streamline processes by eliminating bottlenecks and automating tasks, like optimizing a highway system. Empower teams with autonomy, balancing innovation with tech debt—like creating a startup within a large organization. Invest in real-time data analytics for better decision-making and efficiency 🤝 The Key Takeaway : You can’t improve what you can’t see 👀 Clarity on priorities, progress, and bottlenecks is what separates high-performing engineering organizations from those that struggle. Effective communication and cross-functional collaboration are essential for success! Where is your company at right now? What challenges are you facing, and how are you addressing them? Let’s chat! #EngineeringLeadership #ScalingTech #OperationalExcellence

The Hidden Shift Every Engineering Manager Must Face When I transitioned into engineering management at Microsoft , I thought the key to success was rooted in my technical expertise. After all, I had spent years mastering code, designing solutions, and owning deliverables. But soon, I learned a lesson that reshaped my entire career. Early in my new role, I tackled the team’s technical challenges head-on, diving into problem-solving the same way I did as an engineer. Yet something felt off. Despite delivering solutions, I noticed gaps in team morale, alignment, and overall performance. One day, a mentor pulled me aside and said something that stuck with me: “You’re solving the wrong problems. Your job isn’t to code the solution—it’s to build the team that can do it better than you ever could.” That was my wake-up call. I realized that engineering management is 80% people and 20% engineering. My real role wasn’t just in technical delivery—it was in unlocking the potential of my team, fostering trust, and building alignment. Here’s what I wish I had known from the start: • Engineering management is about translation, not execution. Your primary task is to bridge strategy with systems, ensuring your team is aligned to business outcomes. • Your technical skills take a back seat to your leadership skills. You need to guide, coach, and empower—not micromanage. • Conflict resolution becomes more important than debugging code. Navigating team dynamics is the new challenge. At Amazon Connect today, I carry forward these lessons. The technical wins still matter, but the true legacy lies in the people I help grow and the culture I help shape. So here’s my question to you: What was your wake-up call when transitioning into leadership? What lesson reshaped how you approach your role? Let’s share our insights—because leadership, like engineering, is a skill you can always refine. #EngineeringLeadership #PeopleFirst #GrowthMindset

Why do enterprise implementation projects fail? I wish someone had given me an unfiltered, honest conversation about the true causes of project failures earlier in my career, instead of the sugar-coated corporate messages. I've had the privilege of being part of hundreds of programs, some soaring to success and others stumbling along the way. Regardless of the outcome, we've always owned our mistakes because growth lies in acknowledging them. Over time, patterns have emerged - patterns that those of us with a few "battle scars" recognize all too well. Integration is often the unsung hero or silent saboteur of tech projects. It quietly plays a massive role, yet rarely gets the credit or blame it deserves. Why? Because it's often the largest delivery effort and consequently, the longest. Any hiccup in integration, regardless of its source, ripples across the entire project timeline.    -Engineering Skill/Capability Gap    -Legacy Systems Knowledge Gap    -Misalignment/Misunderstanding of Requirements    -Poor or Missing Enterprise Architect Data conversion is another beast that deserves attention. It can be just as impactful and fraught with challenges as integration. One common pitfall is converting more data than necessary, a mistake that can lead to unnecessary complications and delays. Remember, convert only what's essential to get systems back online and operational.    -Misaligned Data Structures (or worse, incompatibility)    -Legacy Systems Knowledge Gap    -Engineering Skill/Capability Gap    -No Dedicated/Available Environment    -Insufficient Number of Conversion Cycles Business teams are typically forgiving when projects align with their goals. But misalignment, whether real or perceived, is a major red flag. While business organizations usually aren't the cause of failure, misalignment with their objectives can exponentially increase the chances of failure.    -Poor or Missing Business Systems Analyst(s)    -Ineffective Change Management    -Lack of Business Engagement    -IT Dictating Business Decisions Methodology, or the lack thereof, can feel like a myth at times. However, recognizing its importance is a telltale sign of a well-executed project. Toxicity arising within a project, without a clear methodology, can lead to strained relations among teams. Ensuring everyone understands the methodology's expectations and experiences is vital. Neglecting this issue can result in project pauses, reshuffles, reduced staffing, or even a complete halt.    -Smoke & Mirrors (ineffective or ignored methodology)    -Change in Leadership (project resets)    -Ineffective Change Management    -Poor Communication    -Lack of Authority from the Steering Committee We could keep going, we know there are other reasons too. Parting thoughts - If you find yourself caught in a never-ending loop of project resets and reviews, it's time to break free. The staggering costs associated with these start-and-stop cycles makes me nauseous. 💡💼

About a decade ago, I had one of the biggest moments of my career when I shifted from an engineer to a managerial position. I knew things would change in many ways but honestly, I didn’t realize the full extent of the change and many of my mentees have experienced the same. Everything from your role, responsibilities, and how your success is measured is redefined. 1. From Code to Collaboration: As an engineer, your work is all about writing code,  solving technical problems, and shipping features. But as a manager, your focus shifts to helping your team succeed  boosting their productivity, morale, and performance. Instead of writing code, you’re now removing blockers  and guiding the team to deliver results. 2. From Solving Code Problems to People Problems: Engineers deal with bugs, systems, and optimizations. Managers handle conflicts, motivation, and career growth. Your technical expertise still matters, but people skills like empathy and communication becomes just as important. 3. From Focused Work to Juggling Priorities: Engineers often have long stretches of focus time to dive deep into problems. Managers split their time between meetings, planning, feedback, and team development. Delegation and time management become key to handling this shift. 4. From Individual Impact to Team Impact: As an engineer, you directly contribute to building products. As a manager, your role is to enable the team making sure they have the tools, resources, and support they need to succeed. You’re no longer the one writing the code; you’re the one empowering others to deliver results. 5. From Details to the Big Picture: Engineers focus on specific tasks and problems. Managers have to zoom out aligning the team’s work with company goals and ensuring the technical direction supports the business strategy. 6. From Technical Skills to Emotional Intelligence: Engineers rely on logic and technical knowledge. Managers need emotional intelligence to build relationships, support their team, and create a positive environment. 7. From Personal Growth to Growing Others: As a manager, success isn’t about your growth anymore it’s about helping your team grow. You’ll spend time giving feedback, recognizing wins, and mentoring others to help them reach their potential. The journey from engineer to manager is a rewarding one, but it requires a mindset shift and the development of new skills.  – P.S: If you're a senior engineer, tech lead, or a new manager and looking to transition to more senior roles, I'm doing a free webinar soon, please fill out this form to register: https://lnkd.in/gZ7VcqMD

I posted this message in a discord community chat, and thought it might spark a healthy (or heated?) discussion: "Tons of companies need engineering help, and almost none of them understand what that means. There is a huge gap in millwork company leadership that understands both what the business needs and how to execute that effectively in engineering. I've made my entire career navigating this gap, and there's still a huge need for it. The problem is virtually all engineers that have the technical skills and knowledge are lacking in the soft skills to build effective relationships with company ownership, and their peer leaders to effectively support the business needs, and not getting bogged down in chasing efficiency and process for the sake of efficiency and process. In business, results are what matter, and most good engineers struggle with critical feedback and navigating the dynamics it takes to make the jump from individual contributor to managing a department while navigating the difficulties of budgets, personnel hiring and firing, and change management to get a team of people aligned into unified processes and standards. It takes both managing up and down, and stepping outside of your own perspective to see things from your owner and other peer leaders perspectives. Also, what is most efficient for you as an individual contributor may not be a repeatable and scalable process or workflow for your entire team. It teaks a very different set of skills and competencies to fill what.most companies need in engineering. And frankly most companies don't know what they need or how to articulate it. So it first takes earning their trust and showing them results in a way they are comfortable with to get to a point where they trust you to change systems and processes. Additionally, most owners are open to this but their next level down are not. An owner just wants results. Whereas most of their managers and leaders are constantly jockeying for job security and influence within the organization, so they are usually very resistant to someone coming in and possibly jeopardizing their position within the company. At the end of the day, building trust and relationships with the right people in any organization is the key to success. If you can do that, and solve problems for them consistently, then you will never run out of work."

Why Do Business and Engineering Teams Struggle to Align? One of the most common challenges I’ve seen—whether in early-stage startups or scaling companies—is the disconnect between business strategy and engineering execution. When this gap exists, things break down. Business leaders feel like engineering is moving too slowly. Engineers feel like priorities are constantly shifting. Product teams end up playing translator, and frustration builds on all sides. Deadlines slip, expectations aren’t met, and trust erodes. So what separates the companies that get this right? • Shared Language & Context – The best teams don’t just throw requirements over the wall. They make sure engineering understands business priorities, and business understands technical trade-offs. That requires constant communication, not just at the leadership level, but throughout the organization. • Clear Prioritization & Trade-offs – In high-functioning teams, new ideas don’t just become instant priorities. There’s a disciplined process for evaluating impact, stacking hands on what matters most, and making real trade-offs. • Strong Execution Culture – Business and engineering have to align not just on what to build, but how work gets done. That means clarity around milestones, iteration speed, and decision-making. • Trust & Accountability – When teams trust each other, they problem-solve together instead of pointing fingers. The best leaders create an environment where business and engineering are partners, not opposing forces. I’ve seen companies unlock massive value when they get this right—and the opposite when they don’t. Curious to hear from others: where have you seen this done well? #leadership #productmanagement #engineering #execution #businessstrategy