What Have You Learned from a Project that Didn't Go as Planned?
When projects don't go as planned, the lessons learned can be invaluable for future success. Enterprise Product & Technology Leaders and Founders share their hard-earned wisdom in handling such situations. From communicating transparently and adapting to defining clear communication and expectations, discover five key insights from top experts. Get ready to explore the first insight on the importance of transparent communication and adaptation, and the last five on setting clear expectations.
- Communicate Transparently and Adapt
- Leave Breathing Room for Creativity
- Conduct Postmortems and Premortems
- Balance Coaching and Directive Management
- Define Clear Communication and Expectations
Communicate Transparently and Adapt
A key lesson from a project that didn't go as planned is the importance of transparent communication and adaptability. When unexpected delays arise, or there is a blocker on the delivery-critical path, failing to proactively communicate openly with key stakeholders can lead to stakeholder frustration and mistrust in delivery. Regular, fact/data-based updates proved crucial in building trust and focusing on solutions.
Another critical insight was the need for flexibility over rigidity. Sticking to the original plan despite challenges led to rushed decisions. Embracing agility—reprioritizing and pivoting—helped deliver greater value.
Leadership isn't just about steering projects to success but guiding teams through failure with transparency, resilience, and a focus on growth.
Leave Breathing Room for Creativity
During one project, we got so focused on optimizing every step that we hit an unexpected roadblock, and no one had the space to think creatively. I remember sitting with the team, realizing we'd built a system so tight there was no room for new ideas. That moment taught me to always leave some breathing room in any plan. It's often in those unplanned spaces where the best solutions emerge.
Conduct Postmortems and Premortems
It's always a good idea to conduct a postmortem following project completion because it will be eye-opening for both the leader and the team. Importantly, be sure to treat the postmortem as a true learning opportunity—not a finger-pointing exercise. Too many leaders fall into the "whose fault is this" trap, which leads to a deterioration of psychological safety on the team.
In addition to postmortems, consider running a premortem meeting. Many leaders miss this opportunity, but premortems can be helpful in several ways:
Identify Risks Early: Teams imagine the project has failed and brainstorm potential reasons. This surfaces blind spots before they become issues.
Encourage Psychological Safety: By framing it as "predicting failure," team members feel safe sharing concerns without fear of judgment.
Prioritize Mitigation: Rank risks by likelihood and impact, then create actionable plans to address top threats.
Strengthen Collaboration & Resilience: Cross-functional perspectives foster creative solutions and build alignment across teams. Planning for potential future challenges allows teams to be resilient when those challenges do surface.
Balance Coaching and Directive Management
I learned that there is a big difference between coaching and directive management, and when it’s best to use either approach.
During projects that aren't going to plan, you have less leeway to allow more junior members to learn from failures and use a project as a learning lesson for personal growth.
During critical projects that are not going to plan, you need to take a more directive approach with team members who may not yet have the knowledge and experience to solve certain problems.
Coaching—where you allow the team member to set more of the trajectory and just be there to guide them in a more hands-off approach—is usually better for less-critical projects, or at least projects that are currently going well.
Define Clear Communication and Expectations
A key leadership lesson I learned from a project that didn't go as planned is the importance of clear communication and defined expectations. In a previous project aimed at launching a new software tool, we faced significant setbacks due to misunderstandings among team members about their roles and responsibilities. Initially, we were excited about the project, but as it progressed, it became evident that the lack of a well-defined project scope led to confusion and misalignment.
This experience taught me that establishing a comprehensive project charter at the outset is crucial. It should clearly outline objectives, deliverables, and success criteria while ensuring all stakeholders are on the same page. Moving forward, I prioritized regular check-ins and updates to foster open communication, which helped align efforts and mitigate risks.
For anyone leading projects, I recommend investing time in creating a detailed project plan and encouraging an environment where team members feel comfortable voicing concerns or asking for clarification. This proactive approach can significantly enhance collaboration and ultimately lead to more successful outcomes.
