Written by Amna Tariq-Buchholz
A delivery management expert's guide to identifying and solving common project execution problems before they derail your transformation
When Good Strategies Face Weak Execution
“Our teams are working hard ... however, our timelines keep slipping. We don’t know why and need help!”
I often hear this on transformation engagements - from scaling startups to Fortune 500s. Everyone’s committed.
Leadership is sharp.
The strategy makes sense.
The talent is in place.
However, when it comes to the outcomes, clients are facing:
Slipping deadlines
Frustrated teams
Confused stakeholders
A creeping sense that something foundational is off.
The Real Problem Isn’t What You Think
After nearly two decades of leading delivery efforts across hundreds of transformation efforts, I’ve seen common patterns emerge signaling early signs of execution breakdown.
Here’s the truth: it’s rarely about bad strategy or bad people.
It’s what happens when strong strategies meet weak execution: small, compounding issues quietly build up until they’re impossible to ignore.
Think of it like a small leak in your roof – barely noticeable at first, but eventually it brings down the ceiling.
The good news? The warning signs always show up first. If you know what to look for, you can course-correct before your transformation or change portfolio is irreversibly derailed.
The $2 Trillion Cost of Poor Project Delivery
Before we dive into the warning signs, let's establish why this matters. Nearly every 10 seconds, USD $1 million is wasted by companies worldwide due to poor execution of business strategy - approximately $2 trillion annually. (1)
According to the Standish Group, organizations with effective project management practices have 28 times less financial waste through improved execution. We’re talking about USD $122 million wasted for each USD $1 billion invested in low-maturity organizations versus only USD $4 million with high maturity. (2)
And what’s behind that gap? The research is clear: it’s not the strategy or the technology – it's execution. The leading cause of failure include unclear requirements, limited user involvement, and poor planning, all of which points to breakdowns in how projects are delivered.
And the real cost isn't just financial. It's the opportunity cost of delayed market entry, the impact on team morale, and the erosion of stakeholder confidence that can take years to rebuild.
Here are 7 of the most common warning signs we’ve encountered on transformations that are faltering.
Warning Sign #1: Progress Reports Say "Green," While Nothing Is Actually Moving
This is perhaps the most insidious warning sign as it's designed to hide itself – a phenomenon also commonly referred to as “watermelon reporting.” It describes a project
that appears green in status reports, while serious issues beneath the surface (the “red inside”) are quietly putting it at risk.
In one earlier engagement with a major financial organization, my team reviewed several status reports showing consistent "green" ratings across critical workstreams. However, when we dug into tactical level deliverables, we discovered major milestones were not completed on time, pushing actual launch timelines out by months.
We see this pattern usually emerge when reporting becomes a performative process without deep understanding of expectations. Oftentimes, teams might feel intense pressure to show progress during reporting cycles, especially in high-visibility transformation projects. And, rather than surfacing the problems early on, they err towards reporting optimistically, with the hope of solving issues before the next update cycle.
In the industry, we tend to refer to these behaviours as the "reporting theater" - and it's especially common in organizations where there’s a culture of punishing the messenger of bad news.
Resolving this pattern comes down to addressing the root causes underlying such behaviours and may require multiple approaches from ensuring objective and commonly understood metrics are used to manage/report transformation health along with normalizing and encouraging escalation of issues causing blockage to progress.
Warning Sign #2: Teams Are Constantly Working Overtime and Experiencing Burnout
We once worked with a fintech company where the development team averaged 60+ hours weekly, with weekend work completely normalized. The team started off dedicated, however, as exhaustion started to set in, morale dipped, mistakes became more common and team attrition started to rise.
Leadership saw these long hours as a sign of commitment. On a sustained basis, we saw it as a structural failure.
The reality: We see chronic overtime less a symptom of dedication and more a sign of poor planning and resource allocation alongside conflicting priorities during execution. Scope creep can also be a contributing factor which dilutes the original goals. When teams spend
more time reacting than planning, they fall into a "reactive chaos" spiral where every day becomes focused on putting out fires rather than building sustainable progress.
Solving these situations requires focus and patience to restore sustainable delivery rhythms through proper planning, realistic capacity management, and eliminating inefficiencies. A team always performs better when they're well-rested and properly supported than when they're running on adrenaline and caffeine!
Warning Sign #3: Your JIRA Board (Work Backlog) Is Overflowing with No Clear Priorities
One of our client’s development team's JIRA board had over 400 active tickets – with a team of eight resources only! The backlog was a mix of bugs, features, technical debt, and many (many) tasks. The team was struggling with understanding which ticket should be worked on first and how to prioritize if resources needed to be redeployed towards higher priority work. They were clearly busy, but weren't making meaningful progress towards key business goals.
As we unpacked the challenge, it was a reminder that while Agile delivery is an effective way to deliver value with speed, without the right knowledge, mindset and guardrails, it can descend into chaos quickly. In this case, the Agile pod was missing key roles like an Agile Coach or Scrum Master. These roles were critical to drive common understanding and approach within the technical pod for planning and defining work (e.g. through effective Sprint Planning) alongside governance that ensures the team only takes on work they realistically complete.
Warning Sign #4: Stakeholders Don't Know What's Being Delivered or When
Sometimes, we see transformations where key stakeholders are unclear and confused about what is happening when. This creates a domino effect with a significant impact - if a stakeholder group that is required to adopt the change is operationally not ready while the project team is ready to launch, you’ve got a recipe for failure.
This can be caused due to many reasons including not completing a sufficient stakeholder impact analysis resulting in missing important stakeholders. Other factors driving this
could be due to the governance not effectively tailoring and channeling information based on stakeholder needs.
Upfront planning that identifies all key stakeholders and establishes tailored communication plans builds visibility, traceability, and trust — essential building blocks for ultimate project success.
Warning Sign #5: Blockers and Risks Keep Catching You by Surprise
A mid-sized company brought us in during their first ERP implementation after continuously running into unexpected blockers and setbacks. This was raising red flags as they were only four months into the implementation with the launch date already moved out by two months as a result, impacting financial targets and colleague experience.
The truth about “surprises” is that they aren’t actually surprises! Teams would be aware about them, however without the right risk oversight governance and attitude, they stay buried until they become blockers.
With the right cadences and mindset (e.g. using ROAM boards), risk management becomes a proactive vs reactive exercise helping minimize the unknowns and potential blockers. This includes establishing clear escalation paths for emerging risks and fostering a culture where raising concerns early is encouraged and rewarded, not penalized.
Warning Sign #6: People Say the Transformation Is "Strategic," However, Only a Few Are Actually Onboard
AI is being hailed as the biggest disruptor of our generation with many businesses racing to find ways for it to drive benefits. We’re seeing numerous GenAI solutions being launched across organizations with the goal of unlocking value through speed and optimization.
Having said that, strategy alone doesn’t guarantee success. At one client, a well-executed GenAI tool had all the right ingredients- strong technical launch, clear use case, and leadership buy-in. Yet, two months post-rollout, they weren’t seeing the usage and adoption they had hoped for. Teams were continuing to stay with old behavior patterns: using internal knowledge sources (be it intranet, fellow colleagues or even archived email threads!) to complete tasks.
The lesson? Transformations that require behavior change must be treated as people-first initiatives.
This use case illustrated the need for incorporating people change management as a critical workstream in the execution of any transformation. Any transformation which requires people to change and/or adopt new behaviours is a process – missing or speeding through the change steps slows down progress towards delivering outcomes (vs outputs).
Warning Sign #7: Your Team Is Talented, But No One Actually Owns Delivery
So many client transformation teams have brilliant architects, experienced developers, talented business analysts, and knowledgeable subject matter experts. What is often missing is someone explicitly responsible for ensuring the team successfully delivers against its objectives.
This creates a diffusion of responsibility where the team members assume someone else is handling coordination, integration, and overall execution. The result? Duplicated effort, missed handoffs, and no clear accountability for delivering overarching outcomes.
In some teams, this gap can be somewhat supported through blended support by a Project Manager, a Scrum Master, or a Product Owner. However, there still remains a gap on accountability of who manages the delivery from end to end.
With the right skillset and structure, it is possible to create a single point of contact accountable for end-to-end delivery success - someone empowered to coordinate across functions, manage risks, and keep the team aligned. To make this effective, explicitly assign delivery ownership, ensure they have the authority and skills to lead, and establish clear success metrics with regular checkpoints to stay on track.
The Path Forward: Implementing Delivery as a Service (DaaS)
Over the years, we’ve seen firsthand how organizations regain control and confidence of their change transformation initiatives by bringing in structured delivery support. When an organization isn’t able to resolve that internally, we can help with what we call Delivery as a Service (DaaS).
It’s not about inserting rigid templates or overwhelming teams with processes and governance. It’s about meeting each organization where they are and building tailored delivery systems that help our clients successfully achieve their outcomes, minus the chaos or excessive overhead.
Each business has unique needs. The focus should be on establishing rhythm, transparency, and ownership in a structure that adapts to your business context. These builds trust across all levels, allowing leadership to connect strategy with execution without letting the details fall through the cracks.
The impact? Clearer priorities. Fewer surprises. Teams that move with purpose. And most importantly, outcomes that reflect your original goals.
Take Action: Next Steps
If you recognize your organization in any of these warning signs, remember that you’re not alone – and you don't have to fix it alone. These patterns are common, predictable, and solvable. However, they require experienced guidance to resolve effectively.
Immediate Actions You Can Take
Assess: Review your active projects against these seven warning signs to identify those at risk
Prioritize: Identify the issues that could derail your most critical initiatives
Engage: Consider bringing in experienced delivery leadership – internal or external
Invest: Start building delivery management capabilities within your organization
Measure what matters: Establish and monitor metrics that help you identify problems before they become crises
At the end of the day, a solid strategy and a great team deserve better than chaos. They deserve successful outcomes – and the bridge between intent (strategy) and impact (outcome) is where Delivery Excellence lives!
Ready to transform your execution abilities? Let’s talk.
We are a team of delivery transformation SMEs with decades of experience at top tier consulting firms and clients across various industries and geographies. We help organizations turn transformation into traction – the kind that looks like visible progress, aligned teams, and forward momentum on the outcomes that matter. That means no more stalled initiatives, no more overwhelmed teams, and no more stakeholder confusion.
Just confident execution, delivered with clarity. What sets us apart is a flexible service model combined with a distinct Delivery Excellence approach built on three core principles:
Long-term commitment to client success: we focus not only on delivering value during the engagement, but on building capabilities that last well beyond it.
Ownership over Oversight mindset: we don’t just monitor progress; we drive it.
Adaptability: a model designed to meet you where you are, flexing with your needs as they evolve. If you’re curious to learn how to help your organization achieve it’s transformation goals, we’d be happy to connect. Contact me to discuss how professional delivery management through our Delivery as a Service model can help your organization succeed.
If you’re curious to learn how to help your organization achieve it’s transformation goals, we’d be happy to connect.
Contact me to discuss how professional delivery management through our Delivery as a Service model can help your organization succeed.
References
Project Management Institute (PMI). Pulse of the Profession: The High Cost of Low Performance. PMI Global Report.
The Standish Group International. (2024). CHAOS Report 2024: Beyond Infinity. The Standish Group.
Deloitte. (2024). Future of Work in Technology: 2024 Survey. Deloitte Insights.
Prosci. (2024). Best Practices in Change Management - 12th Edition. Prosci Benchmarking Report.
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