Every tech organization faces challenges as it grows. What starts as a speedy team delivering features quickly can gradually transform into something that feels slow, opaque, and frustrating. This is normal to a certain extent – and also not dangerous when it is recognized and tackled by the responsible tech-leaders in a timely manner. The question I want to discuss today is: when do growing pains become systemic issues that require bigger changes, some kind of a reset or external help?
Having built and led engineering teams for over 15 years, working with my own organization and many partners, I have seen certain patterns emerge repeatedly and on multiple levels. More importantly, I’ve learned to recognize the warning signs before they become critical failures.
I will be talking a lot about technology leaders in this article – and just to make it clear: this includes a lot of different groups of people. Engineering managers, agile coaches, product owners and product managers are usually part of the conversation. I am not trying to blame any of those groups, usually they are all trying hard to do their best – while missing the tools and experience to do so efficiently.
Here are five indicators that your tech leadership team might need help, along with what is usually happening beneath the surface.
1. Deliverables Are Consistently Delayed – And Nobody Really Knows Why
This is perhaps the most visible symptom, but also the most misunderstood. When delivery dates consistently slip and the reasons feel vague or circular (“we underestimated the complexity,” “there were unexpected dependencies,” “the requirements changed”), you are usually looking at a planning and estimation problem, not a team capability issue.
What is really happening: Your tech leadership lacks the frameworks and processes to break down complex work into predictable chunks. They are making commitments based on gut feelings rather than historical data and systematic analysis. Maybe they don’t even understand that what they are saying is understood as commitment from the other side. The constant surprises are not random – they are the inevitable result of insufficient technical discovery and planning discipline.
The deeper issue is often that technical leaders don’t know how to say “we need two weeks to properly scope this before we can give you a somehow reliable estimate.” Instead, they provide optimistic guesses under pressure, setting everyone up for disappointment.
2. Trust and Transparency Have Eroded Between Product and Engineering
When product managers start using phrases like “the engineering team is a black box” or engineers consistently feel like they are being asked to deliver the impossible, you have lost the foundation of effective product development. This usually manifests as product management making commitments without engineering input, or engineering pushing back on everything as a defensive mechanism.
What is really happening: Your organization lacks established rituals and communication patterns that create mutual understanding. Product doesn’t understand the technical constraints and tradeoffs engineers face daily. Engineering doesn’t understand the market pressures and customer needs driving product decisions.
This isn’t about personalities – it’s about systems. When trust breaks down, it’s usually because there aren’t clear, consistent ways for both sides to share their perspectives and make decisions together. The resulting dynamic becomes toxic – and collaboration suffers.
3. There’s a Growing Gap Between What the Organization Needs and What R&D Delivers
This manifests when sales teams start making excuses for missing features, customer success struggles with product limitations, or marketing can’t confidently promote your technical capabilities. The usual engineering response is to push back harder, pointing to resource constraints and competing priorities.
What is really happening: your R&D leadership (once again: this includes product management, product owners and engineering managers) isn’t effectively translating business needs into technical strategy. They’re operating in reactive mode, responding to the loudest voice rather than systematically prioritizing based on strategic value. The constant push back isn’t stubbornness – it’s a symptom of leaders who don’t have frameworks for making and communicating difficult tradeoff decisions.
The most telling sign is when engineering leadership can’t articulate why they’re saying no to certain requests or what it would take to say yes. They’re managing tactically rather than strategically, resorting to the only thing they feel they can still do – pushing back, rather than being creative themselves.
4. Roles Are Unclear and People Aren’t Operating at Their Full Potential
This is often most visible with roles like Scrum Masters, who end up functioning as team assistants rather than process improvement catalysts. But it extends throughout the organization – senior engineers doing junior work, managers spending all their time in the weeds instead of developing their teams, product owners who aren’t actually empowered to make decisions.
What’s really happening: Your leadership team hasn’t invested in defining roles clearly or doesn’t have the management skills to coach people into their full potential. Role clarity isn’t just about job descriptions – it’s about helping people understand how their role evolves as they grow and how it interfaces with other roles on the team.
When a Scrum Master is reduced to taking meeting notes instead of identifying and resolving team impediments, it usually means management doesn’t understand the value that role can provide or how to set that person up for success.
5. Engineers Don’t Understand or Stand Behind What They’re Building
When your engineers can’t explain why the feature they’re building matters to customers, or when they consistently question the value of their work, you have an alignment and communication problem. This often presents as engineers suggesting alternative solutions that miss the business context or being disengaged from product discussions.
What’s really happening: Your technical leadership isn’t effectively communicating context and purpose. Engineers are smart people who want their work to matter – when they don’t understand the ‘why’ behind their tasks, it’s usually because leadership hasn’t created systems to share that context consistently.
This also happens when engineers are excluded from customer conversations and business strategy discussions. They end up optimizing for technical elegance rather than customer value because they don’t have visibility into what customers actually need.
The Common Thread: Management Fundamentals Are Missing
If you recognize multiple signs from this list, the underlying issue is usually the same: your technical leaders are missing fundamental management and leadership skills. They’re great individual contributors who were promoted based on technical excellence, but never received proper training in planning, communication, delegation, and strategic thinking.
This isn’t criticism – it’s reality for most growing tech companies 😉. The skills that make someone an excellent engineer are different from the skills that make someone an excellent engineering leader. Without proper development and coaching, even the best potential leaders will struggle with these challenges.
What Actually Helps
The good news is that these are all solvable problems. The bad news is that they won’t solve themselves. Here’s what typically makes the difference:
Leadership coaching and development – Your technical leaders need to develop new skills in strategic thinking, communication, and team development. This isn’t something they will usually figure out through trial and error while running a demanding organization. They are usually extremely smart people – with very little time to spare to invest into their own development.
Process and framework implementation – Successful teams have systematic approaches to planning, decision-making, and communication. These aren’t bureaucratic overhead – they’re the tools that enable transparency and predictability.
External perspective – Sometimes you need someone from outside your organization to identify blind spots and help implement changes. Fresh eyes can see patterns that are invisible to people inside the system.
The key insight is that these issues compound over time. The longer you wait to address them, the more entrenched they become and the harder they are to fix. But with proper support and commitment to change, most tech-organizations can transform into being an enabler again, rather than a source of frustration. If you need help with this transformation – feel free to get in touch!
