Avoiding the same mistakes (over and over again)
No leader wants to deal with project failure, yet every portfolio has a few battle scars—initiatives that spiraled out of control, missed the mark, or quietly disappeared from dashboards with little explanation. Failure happens. The bigger issue? When teams don’t take the time to learn from it, setting themselves up to make the same mistakes all over again.
The best organizations don’t just move on from failure—they study it, document it, and use it to improve how they manage portfolios. According to Gartner’s Program and Portfolio Management Practices for Turbulent Times report, companies that invest in value management and continuous learning are far better at avoiding repeat failures. They build systems that expose weak points before they become full-blown crises, ensuring every project—whether a success or a struggle—teaches them something useful.
So how do you turn painful lessons into strategic advantage? It starts with capturing insights, strengthening collaboration, and fostering a culture of continuous learning.
Making post-mortems actually worth it
When a project underperforms (or completely implodes), the instinct is often to just move on—especially in fast-paced environments where there’s always something new demanding attention. But skipping reflection guarantees one thing: future projects will stumble over the same obstacles.
That’s why strong portfolio leaders make post-mortems a priority, not an afterthought. These aren’t just “what went wrong?” sessions. They’re about fact-based analysis that surfaces real insights teams can apply moving forward.
A good post-mortem doesn’t just rehash timelines and assign blame. It asks the right questions to get to the heart of the issue:
- What worked well, and why?
- What barriers did we encounter, and were they avoidable?
- How can we adjust next time to improve outcomes?
Digging into the root causes—instead of just surface-level symptoms like “we missed a deadline”—helps teams address systemic issues rather than just firefighting individual problems. Documenting lessons learned in a structured way ensures they don’t get lost in meeting notes no one will ever read. After all, the goal isn’t just to reflect—it’s to ensure the next project benefits from what you’ve already figured out the hard way.
When collaboration breaks down, projects follow
Not every failure is the result of poor execution. Sometimes, it comes down to a communication breakdown between teams and stakeholders. Misaligned expectations, unclear ownership, and shifting priorities can doom a project before work even begins.
Portfolio managers often assume alignment happens organically, but in reality, it takes deliberate effort. Without clear definitions of success, accountability, and decision-making authority, teams end up working at cross-purposes.
The best way to prevent this? Set the foundation early.
- Facilitate alignment workshops at the start of major initiatives to establish a shared understanding of goals and priorities.
- Clarify roles with frameworks like RACI (Responsible, Accountable, Consulted, Informed) to eliminate confusion over decision-making authority.
- Maintain a single source of truth for project data to avoid conflicting information that derails progress.
When projects go sideways, a lack of alignment is often the culprit. The more upfront clarity teams have, the less time they spend navigating misunderstandings and chasing miscommunication.
This is where OnePlan can help. By centralizing portfolio visibility, it enables teams to track priorities, communicate corporate strategy, and provide real-time resource transparency.
“Using OnePlan, we’re able to have that one source of truth across multiple portfolios. We are able to report & visualize the information and use those insights in order to make key business decisions.” – Linda Hadden, Innovation Program Manager- ChampionX
Teams like ChampionX are using OnePlan for that source of truth to ensure everyone works from the same playbook instead of a scattered collection of tools and spreadsheets.
Building a culture where teams actually learn
Organizations that continuously learn and adapt don’t just survive turbulent times—they thrive in them. The challenge? Too many companies treat learning as an individual responsibility instead of an embedded team discipline.
If continuous learning isn’t baked into how portfolios are managed, mistakes will repeat themselves, valuable insights will disappear, and teams will operate in silos—reinventing the wheel every time a problem arises. Strong leaders prevent this by making learning an ongoing practice.
Here are just a few ways to make it stick:
- Conduct quarterly retrospectives. Portfolio-wide performance reviews keep teams from waiting until a crisis forces change.
- Establish mentorship programs. Senior leaders have hard-won insights—build opportunities for them to pass that knowledge down.
- Create knowledge-sharing forums. Give project managers a space to exchange insights, challenges, and best practices across departments.
Capturing lessons is only half the equation—applying them is what makes the difference. A structured retrospective framework can help teams reflect on both qualitative insights (team dynamics, collaboration) and quantitative outcomes (ROI, efficiency gains), ensuring continuous improvement is actually measurable.
Turning insights into action
Failure is only wasted if nothing is learned from it.
The strongest portfolios aren’t failure-proof—but they are failure-resistant because they continuously improve. The teams that invest in learning, alignment, and adaptation are the ones that recover faster, execute better, and make smarter decisions over time.
When markets shift, and priorities change, the best leaders aren’t the ones who avoid missteps entirely. They’re the ones who see every challenge as an opportunity to get better. The question is: will your team repeat past mistakes, or use them as fuel to build a stronger, more innovative portfolio?
