Breaking the Cycle of Software Delivery Delays
Strategies for Leadership, Sales, Product Management and Engineering Teams
For most businesses, large or small, software delivery is accompanied by delays, late nights, and the inevitable frustrations that come with them.
In the article Why does it feel like product features take forever to ship, we explored the key reasons behind software product delays. While the topic is far too complex to capture in a single list, one key takeaway remains:
Delays are rarely caused by engineering teams alone. Instead, they arise from a tangled web of organizational challenges.
Misaligned priorities, communication breakdowns, technical debt, and other systemic issues ripple across the company, affecting both engineering teams and stakeholders.
Until these deeper issues are addressed, delays will remain a recurring challenge.
How to Keep Software Delivery on Track
Delays in software delivery are not an engineering problem only — they’re a shared responsibility.
From leadership to business stakeholders, product managers, and engineering teams, every part of the organization has a role to play in addressing this challenge.
Leadership’s Role: Culture as the Foundation
Change starts with culture. Culture sets the tone for how teams behave, communicate, and how ambitious goals they set.
A strong, cohesive, ambitious, and blameless culture sets the foundation of high productivity and timely delivery.
Here are key areas where leadership can make a difference:
1. Breaking Down Silos
How well do your sales, product, and engineering teams understand each other?
A sales rep is unlikely to grasp the intricacies of a technical challenge. But can they empathize when an engineer says, “We’re at high risk of a delay”?
Similarly, are engineers confident enough to raise red flags without fear? And can they empathize with the sales team’s urgency and pressure to deliver the next feature release?
Transparency and psychological safety have shown to be the number one factor for high productivity. Without it, teams retreat into silos, withhold information or avoid critical conversations. When that happens, delays become inevitable.
If your teams operate in silos, it’s time to break the walls.
Organize cross-functional workshops where teams learn about each other’s challenges.
Share dashboards and data across teams to increase transparency and foster alignment.
Publicly encourage open dialogue and reward transparency.
2. Teams Accountable to Outcomes
If your business teams define what to built, while success for engineering teams is measured by timely execution only, it’s a red flag.
When decision-making rests entirely with stakeholders, technical solutions are rarely optimal, inefficiencies and delays are inevitable.
Shift the focus from output (features, timelines) to outcomes (business impact, user behavior).
Instead of requesting: “Deliver Feature X by next month?”
ask: “How can we achieve the desired user behavior or business impact?”
Empower product and engineering teams to deliver on clear outcomes.
This makes them better positioned to find innovative, efficient solutions that achieve the same goals with optimal technical resources.
3. Focus on Big, Clear Goals
If you want to drive meaningful progress, set bold and clear goals.
Leaders should define clear goals, inspire their teams, and align everyone around a shared vision.
The guiding principle here is: less is more. When there are too many initiatives, all labeled as equally important, people often fail to feel a sense of urgency for any of them. But when one key goal is emphasized, it becomes a unifying focus, orienting teams toward solving the same challenge.
When coffee chats and informal conversations revolve around the same goal, you know you’ve achieved focus. At that point, teams aren’t just working together—they’re working toward a shared vision.
4. Data-Informed Culture
Data increases transparency. It highlights risks and potential delays by making progress measurable and visible.
When discussions between IT and business teams are backed by data, personal biases are removed, shifting the focus from opinions to solutions.
Research shows that Data-mature organizations achieve 2.5 times better business outcomes than their less mature counterparts. This underscores the impact of embracing data-driven practices.
Integrating data starts from creating a data-informed culture. Leaders must set a high standard by emphasizing the use of data to track progress and measure outcomes. They should create an environment where teams are empowered to leverage data—not just for tracking progress but also for steering product roadmaps and making informed decisions.
5. A Culture of Quality
Engineering productivity and quality go hand in hand. Scalable architecture, automated processes or adopting new technologies are key to accelerating product development.
But quality doesn’t come for free.
Engineers need the mental space and time to innovate and improve. A constant pressure to deliver quickly erodes quality, leading to higher costs, slower progress, and unexpected delays down the line.
While maintaining quality is a core responsibility of engineering teams, leadership plays a crucial role in supporting this effort. This involves fostering quality awareness across teams, pushing for modern tools and technologies, and recognizing when strategic investments—like a major system migration—are necessary.
When leadership backs quality, teams are empowered to build better, faster, and more sustainable solutions.
Sales Role: Align Customer Needs With Product Strategy
Sales teams are the frontline of customer interaction. They bring new demand and ideas for product features.
Their role isn’t just about closing deals—it’s about aligning customer needs with the product strategy and maximizing satisfaction with what the product can realistically deliver.
Here are key principles to follow:
1. Communicate Value, Not Features
Customers request specific features, but the real value is understanding Why they need them. Without digging deeper, the true problem the feature is meant to solve may remain hidden.
Ask questions:
What problem are the users trying to solve?
How will this feature change their behavior or workflow?
Will it help them make better decisions?
Focus the communication (both with the customer and the product teams) on value. Avoid getting into a discussion about a rigid feature description or specific implementation. Let the product team decide how to deliver the value in a most effective way.
2. Stay Close to the Product Roadmap
Customers often ask for specific features with great enthusiasm. Resist the urge to immediately say "Yes" unless it aligns with the next priority on your product roadmap.
Being overly flexible with customer requests doesn’t necessarily make you customer-centric—it can signal that your product’s sustainability and scalability are at risk.
Here’s an interesting phenomenon: what seems urgent today often loses its relevance within a day or two. Instead of rushing to commit, take a step back and consider:
Would this feature truly address the customer’s current top priorities?
Is this request a strategic step for your product? Does it align with your roadmap and provide value for other customers?
If the feature’s value is questionable or misaligned with your strategy, redirect the conversation. Highlight for example an upcoming feature that offers even greater value and supports your customer’s goals. This approach not only keeps customers excited about what’s to come but also makes life easier for your product teams by avoiding unnecessary detours.
Check out Ben Yoskovitz's guide for practical tips on navigating sales conversations without derailing the product roadmap, How Do You Decide to Build a Feature to Close a Deal?
3. Avoid Time Commitments
New features are rarely as simple as they seem.
Delivery involves more than writing code—it includes testing, deployment, maintenance, and handling unforeseen challenges along the way. Data indicates that the effort spent on maintaining a feature over its lifetime is about five times greater than the effort required to build it.
Avoid promising timelines without consulting the engineering team. Try to keep promises as much as possible realistic to maintain credibility with both customers and internal teams.
Product Manager’s Role: Clarity, Prioritization and Focus
Product Managers (PMs) sit at the intersection of business, engineering, and customer needs. Their role is to prioritise smartly and ensure focused execution.
Here’s how PMs can contribute.
1. Set Clear Priorities and Focus
Is your roadmap cluttered with various initiatives and you don’t feel it’s connected to the reality?
If so, step back. Cut the nice-to haves and all distracting items on your roadmap and highlight the few initiatives that would generate highest value.
Clean and simple roadmap is what will keep teams focused and motivated.
2. Clear and Transparent Communication
Miscommunication leads to rework, missed expectations, and unrealistic timelines.
For product teams: Make sure engineers have a clear understanding of prioritized goals and expectations. Keep product requirements concise, well-documented, and specific. Shorten feedback loops to avoid unnecessary back-and-forth.
Practical tip: Never leave a discussion with ambiguity. If there’s even a hint of misalignment or confusion, address it immediately—ambiguity almost always leads to mistakes and delays.
For stakeholders: Be upfront about what’s feasible, what’s at risk, and the trade-offs involved. Transparent communication builds trust and reduces last-minute surprises.
3. Ambitious Yet Realistic Planning
PMs should champion challenging but realistic planning that considers technical complexities and potential risks.
Work closely with engineering to estimate timelines based on actual effort and anticipated challenges. Agree on must-have goals but also stretched goals.
Keep it balanced. Overly conservative plans can kill innovation, while overly ambitious plans can demoralize teams. Strive for ambitious yet realistic goals to keeps the team challenged without overwhelming them.
Engineering Role: Quality and Waste Reduction
Engineering teams are at the heart of product delivery. They might not control every factor influencing delays, but they have the power to make significant improvements.
Here are a few key principles for engineering teams to excel:
1. Focus on Quality
A low-quality product creates a long-term technical debt that hampers your ability to deliver effectively.
While it may be tempting to cut corners under tight deadlines, shortcuts should be the exception, not the norm. Left unchecked, technical debt can quickly escalate, slowing down progress and increasing costs.
The same applies to the software development process itself. Software development is often accompanied with waste, from task switching and inter-team dependencies to manual processes and vague requirements.
Building waste reduction into your sprint routine by dedicating 10–15% of each sprint on fixes inefficiencies can make a big difference. This could include automating repetitive tasks, clarifying requirements upfront, or simplifying workflows.
Keep high product standards. This boosts productivity but also overall team satisfaction.
2. Communicate Risks Early and Back Them With Data
Engineers are often the first to identify risks that could impact timelines or create bottlenecks.
Don’t wait until it’s too late to raise concerns. Share high-risk areas as early as possible. If you feel your voice isn’t being heard, work on the clarity of your message.
Here’s how to make your message resonate:
Use simple language to explain risks. Avoid focusing on the technical details; instead, emphasize the business impact.
For example: "If we proceed with this architectural decision, it could increase maintenance costs and delay future releases by six months."
Support your concerns with data to add credibility.
For example, highlight how a suboptimal architectural choice today could double workload or create delays down the line.
Not every concern will immediately become a top priority, but creating awareness is key. When the decision-makers understand the real implications of a flagged issue, they can balance it against the other business priorities. What might seem like a lower concern today could be the next quarter’s most urgent initiative.
3. Master Planning
Accurate planning is a tough challenges in engineering, but it’s critical.
Whether you use story points, velocity metrics, or other estimation tools, the key is to continuously refine and improve your planning process. Start simple—use basic time estimates—and focus on improving accuracy with each iteration.
Most importantly, plan for the unexpected. Build in buffers for unforeseen hiccups and avoid relying solely on best-case scenarios. The goal is to strike a balance: set realistic, achievable targets while keeping them challenging enough to inspire teams to push their limits.
Wrap Up
While systemic challenges require collective effort, you don’t have to wait for the perfect scenario to start making an impact.
Begin with what you can control.
If you’re an engineer, raise risks early, improve the clarity of your communication, and stay committed to quality.
If you’re a product manager, review your roadmap critically and speak up if it feels unachievable.
Small actions can inspire others and create momentum. When your manager recognizes the value of your small initiative, it can ripple upward, encouraging leadership to set bigger goals and drive meaningful change.
By applying these strategies, you’re not just reducing delays—you’re laying the foundation for trust, innovation, and excellence across your organization.
What’s one small step you can take today?
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