The Hidden Pitfalls of Project Failure: Lessons from a Tech Partner
Organisations often embark on software implementation projects to improve efficiency, enhance visibility, and drive better decision-making. Despite these objectives, many technology projects face significant hurdles. There are consistent trends across industries that can derail implementations, but with early identification and the right remediation measures, these challenges can be overcome.
In this article, Briana Hughes, our General Manager, Commercial Sector consulting, draws on her years of experience working with a range of organisations to highlight the common pitfalls encountered when implementing Project and Portfolio Management solutions (and tech projects generally) and how your organisation can avoid these to make your next implementation successful.
Here are Briana’s top observations on why implementations fail and ways to ensure project success.
1. Unclear Requirements: Setting Yourself Up for Failure
You cannot build a house without blueprints, and you cannot implement software effectively without clear requirements. Many organisations assume they know what they need, but when asked to document requirements, they struggle to articulate them in detail.
Solution: Begin with a comprehensive discovery phase, engaging key stakeholders to identify pain points and define desired outcomes. Clearly document these insights in a way that both your business and implementation partner can understand, ensuring alignment from the start. Engage with key subject matter experts for their expertise, but balance this by thinking outside the box—what works today may not be the best path forward for the future.
In my current role at Sensei, we collaborate closely with clients during the Discover and Align phase of implementations to refine our clients’ requirements, capture measurable benefits, and establish a clear roadmap for both immediate and long-term success, ultimately assisting you in improving the way you work.
2. Inability to Clearly Define Your Challenges
In my most recent role, which focuses on the delivery of PPM, and Work Management systems, the solution is intended to address business problems. However, if these problems are not clearly articulated, there is a risk of implementing an incorrect solution or even worse, automating inefficiencies. Every organisation encounters unique challenges and openly identifying them ensures that the implementation team has a comprehensive understanding of what needs to be addressed.
Solution: Prioritise business challenges over system features by using a structured framework to uncover and define them. A simple yet effective approach is the Problem-Impact-Need (PIN) Framework:
- Problem: What specific issue or bottleneck are we facing?
- Impact: How does this problem affect efficiency, decision-making, or outcomes?
- Need: What must change to resolve this issue?
Work through this framework with key stakeholders to capture pain points, ensuring your system is configured to drive meaningful improvements and deliver real business value.
3. Lack of Business Buy-In: Overcoming the PMO Perception Problem
PPM implementations are often driven by the Project Management Office (PMO), but the challenge is that not everyone values project management. Many business teams see projects as costly, slow, and prone to failure, leading to scepticism about the PMO’s role and the system’s importance. Without business buy-in, adoption will be an uphill battle, leading to resistance, delays, and ultimately, project failure.
A key aspect often underestimated is the physical time and capacity required from the business to make the implementation a success. Transformation projects demand more than just approval—they require meaningful engagement, input, and time investment from key stakeholders. Too often, organisations miscalculate the workload involved, assuming the implementation team will handle everything. However, business participation is crucial for providing requirements, testing, training, and driving adoption. Without this, even the best-designed solution will struggle to deliver value.
Solution: Shift the conversation from “Why project management?” to “How does this system help the business?” Secure executive sponsorship early and frame the benefits in business terms—how the system will enable better decision-making, improve visibility, and reduce wasted effort. Identify influential champions from different departments who can advocate for the system’s value, helping to change perceptions and build momentum for adoption.
Additionally, organisations should plan for the time commitment required. Your implementation provider can help outline the activities and level of involvement needed, giving you a clear picture of what to expect before your project starts.
4. The One-Person Show: A Single Point of Failure
All too often, one person is solely responsible for defining requirements, testing, and adoption. When this happens, the project reflects only their perspective, missing the broader organisational needs.
Solution: Form a cross-functional team with representatives from various departments to align configurations with business objectives and promote shared ownership for smoother adoption. Engage team members at key phases—analysts for requirements gathering, super users for testing, and department leads for adoption—allowing them to balance project involvement with their daily responsibilities. Implement feedback loops through testing sessions, surveys, and pilot programs for continuous improvement. Maintain regular communication via updates, town halls, and targeted training to keep stakeholders informed and engaged.
5. Trying to Do Too Much on Day One: The All-or-Nothing Trap
A common pitfall I see in PPM implementations is organisations getting excited about all the possibilities and trying to roll out every feature and automate everything from day one. On the surface, it makes sense—why not take full advantage of everything the system can do right away? But this approach almost always leads to frustration, resistance, and poor adoption. Moving to a new system is already a big shift, and throwing too much at users—whether it’s automation, new processes, or a stack of extra functionality they didn’t have before—creates unnecessary complexity. Just because a system can do something doesn’t mean it should on day one. More functionality doesn’t automatically mean more efficiency—if users aren’t ready for it, you’re just making their jobs harder.
Solution: Rather than trying to do everything at once, take a Minimum Viable Product (MVP) approach—start with the core functionality, get users comfortable, and then expand gradually. A phased rollout allows you to test, refine, and introduce new features based on real-world use, rather than assumptions. The best implementations evolve alongside the business. Once teams start using the system, they’ll uncover new opportunities, and your implementation partner will be able to provide solutions that further improve the way you work—often these are opportunities that weren’t even considered at the start. By keeping things simple early on and scaling up strategically, you create a system that drives real value and sets users up for long-term success.
6. Skipping User Acceptance Testing (UAT): Do not Serve the Dish Without Tasting It
Many organisations assume that if the software “works,” it will seamlessly fit into their business. But without testing real-life scenarios, hidden issues will surface post-launch, leading to frustration, resistance, and a system that does not deliver what you need.
Think of it like working with a chef to design a new menu. They can use the best ingredients, follow your preferences, and craft what they believe is the perfect dish. But if you never taste it before serving, how can you be sure it meets your expectations? If the dish flops, is it fair to blame the chef when you never tested it yourself?
The same principle applies to your PPM system or any other implementation. A great implementation partner will support you through requirements, technical testing, and UAT—but staying actively engaged is key to ensuring the system meets your needs. If gaps are only discovered after go-live, it can be frustrating for everyone involved. Rather than placing blame, fostering collaboration throughout the process helps build a solution that truly works for your organisation. Implementation teams are most effective when UAT is approached with care, helping to identify and resolve issues early for a smoother transition and long-term success.
Solution: Never skip UAT. Have end-users test the system using real data and actual business workflows before go-live. This step is essential for uncovering gaps, validating processes, and ensuring the system aligns with your business needs. A strong partner will provide valuable support, but the success of the system depends on your active commitment and involvement in making it work for your organisation.
7. Treating Your Implementation Vendor as Just a supplier, not a True Partner
Your implementation partner’s ultimate goal aligns with yours: delivering a successful project that leads to tangible business improvements and the desired benefits. However, many organisations fail to fully leverage their vendor’s expertise by treating them as mere suppliers rather than strategic partners. This often results in missed opportunities for optimising processes, fine-tuning configurations, and addressing potential issues early in the project.
Solution: Shift your perspective and treat your implementation vendor as a true strategic partner. Vendors bring valuable insights from their experience across multiple implementations, knowing what works and what does not. By engaging them in open discussions, being receptive to their recommendations, and working collaboratively, you can drive better outcomes and ensure the project’s long-term success. Their expertise is an asset to your business transformation—tapping into it fosters a partnership that benefits both parties and contributes to smoother execution and greater results. And remember, implementation is often not the end of the journey—it’s just the beginning.
Final Thoughts: Avoiding the Common Traps
PPM software implementations, and technology implementations in general, do not always fail because of the technology itself—they often fail due to inadequate planning, lack of engagement, and an inability to adapt. By proactively addressing these common challenges, you can significantly increase the likelihood of delivering lasting value to the business.
If you’d like to find out how we can help make your next PPM platform transition a smooth one, get in touch.
