What this article is about :
Are you a leader looking to elevate your impact during program checkpoints? Discover how to transform these critical meetings into opportunities for strategic oversight and team empowerment. Learn the common mistakes leaders make and the actionable strategies to ensure that your involvement drives progress and fosters a collaborative environment.
This is the follow up to the article about checkpoints published June 24 2025 : https://kaleo-performance.com/en/program-checkpoints-navigating-product-development-with-program-progress/
Opening: The Checkpoint Clash
The air in the conference room was thick with tension. The program manager, Sarah, presented the latest update on Project Phoenix. Budget overruns, delayed timelines, and a key supplier issue hung heavy in the slides. But instead of listening, the VP of Engineering launched into how to make better slide wording and content. Then, the Head of Marketing grilled Sarah about how she was planning to execute a new marketing campaign she hadn’t even been briefed on. In addition, the Head of Purchasing declared the transition to a new production plant, a recent initiative that he wanted this program to lead. What started as a critical check-in devolved into a frustrating verbal exchange with an onslaught of new objectives and unclear path forward on program risks and issues. Sound familiar?
The Power (and Peril) of Checkpoints
Checkpoints are crucial decision points in any program. They’re designed to:
• Assess Progress: Understand where the program stands against its objectives and planned milestones.
• Validate Assumptions: Ensure the initial assumptions driving the program remain valid.
• Identify and Mitigate Risks: Proactively uncover potential roadblocks and plan mitigation strategies.
• Enable Course Correction: Make informed decisions about whether to continue as planned, adjust scope, reallocate resources, or even pivot direction.
The expectation is that checkpoints provide a focused opportunity for strategic oversight and informed decision-making. However, even with best of intentions, leaders unintentionally derail these meetings. Here are three of the most disruptive and avoidable mistakes we commonly see.
Theme 1: The “Expert Interrogation” Leadership Attitude – Embrace Servant Leadership
• The Problem: Many leaders view checkpoints as opportunities to showcase their expertise, interrogate the program team, or impose their own solutions. They come in with pre-conceived notions and are resistant to new information. This creates a defensive atmosphere, stifles open communication, and undermines the team’s autonomy.
• The Solution: Adopt a servant leadership mindset. Instead of asking “What are youdoing wrong?”, ask “What’s needed? How can we help?” The checkpoint is not the time to set new expectations or drastically change direction without a clear understanding of the consequences. Focus on understanding the challenges the team is facing and offering support, resources, and guidance. Your goal is to empower the team to overcome obstacles and deliver results.
Example: Instead of saying, “This timeline is unacceptable! We need to accelerate everything,” try, “I see the timeline is tight. What are the biggest constraints preventing you from meeting the original schedule? What resources or support could help alleviate those constraints?”
Theme 2: Lack of Checkpoint Preparation – Understanding the Product Lifecycle, Checkpoint Intent, and Awareness of Program Objectives
• The Problem: Leaders have great authority but often attend checkpoints without properly preparing, lacking a deep understanding of both the true intent of that checkpoint, and the program’s objectives, key risks, and recent developments. This can lead to uninformed questions, irrelevant tangents, and potential changing of objectives. Moreover, leaders can come with their own bias as to expected outcome, have hidden agendas, or try to command silo objectives. This undermines the entire checkpoint process, pollutes the evaluation process, and prevents objective assessment, leading to disruption and delay of Program progress.
• The Solution: Come prepared by doing your homework! A deep understanding of the product development and checkpoint process is critical. Also, review program charter, objectives, risk register, and any pre-read materials provided by the program manager. Understand the program’s key performance indicators (KPIs) and how they are trending. If you don’t understand something, ask for clarification before the meeting.
Example: Before the checkpoint, ensure you understand the true intent of this checkpoint – what milestones should be achieved, what decisions are being made? Also review the program’s risk register and focus on understanding the potential impact of the top three risks. Be prepared to discuss potential mitigation strategies and resource needs if those risks materialize.
Theme 3: Failure to Understand the Implications of Program Risk – Look Beyond the Surface
• The Problem: Leaders often focus on the immediate status updates without fully grasping the potential downstream implications of identified risks or delays. They also often underestimate or downgrade the severity of a risk or fail to anticipate its cascading effects.
• The Solution: Go beyond the surface-level information. Ask probing questions about the potential impact of risks on other areas of the program, related projects, or the overall business strategy. Understand the intended course of action if a risk occurs and evaluate its feasibility. Evaluate if this is a risk, or has it evolved into a real issue. Review and challenge assumptions and encourage the team to think critically about potential worst-case scenarios. Be prepared to activate organizational help if needed.
Example: If the program is facing a potential delay in a key software integration, ask: “What are the implications of this delay on the launch date? How will it affect the marketing campaign? What contingency plans are in place to mitigate the impact on our customers?”
Conclusion: Becoming a Checkpoint Champion
By embracing servant leadership, diligently preparing for checkpoints, and deeply understanding risks and implications, leaders can transform these meetings from sources of frustration into powerful engines of progress. You have a critical role to play in providing strategic oversight, offering valuable insights, marshalling other organizational resources to help when needed, and empowering your program teams to succeed.
What are your experiences with leadership involvement in program checkpoints? Share your tips and challenges in the comments below!
Interesting to read all articles of Kaleo ‘s blog : https://kaleo-performance.com/en/blog-en/
