Keep Progress on Track with Regular Check-Ins

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Keep Progress on Track with Regular Check-Ins

Optimise Progress Through Regular Check-Ins

Introduction to Regular Check-Ins

Regular check-ins are essential for keeping individuals on track, providing ongoing support, and ensuring that the plan remains aligned with development needs. They can also mitigate the Dunning-Kruger effect and Impostor Syndrome by providing realistic assessments of one’s skills and progress.

Set a Schedule for Check-Ins

Determine a schedule for regular check-ins. The frequency can vary depending on the goals and milestones. Having a set schedule creates structure and accountability.

Example: A software engineer sets a weekly check-in with a mentor to discuss progress in learning a new programming language. Without regular check-ins, the engineer might overestimate their proficiency or underestimate it due to cognitive biases.

Prepare for the Check-In

Before each check-in, individuals should prepare by reviewing milestones, evaluating progress, and considering challenges. Preparation makes the check-in more focused and productive.


  • List achievements since the last check-in.

  • Provide specific examples of challenges faced.

  • Consider what support might be needed.

Conduct the Check-In

During the check-in, engage in an open conversation about progress and challenges.

  1. Review milestones and progress.

  2. Discuss challenges, and brainstorm solutions.

  3. Compare self-perception with evaluations.

  4. Review feedback from evaluations.

  5. Discuss additional support or resources.

  6. Reflect on the overall journey and growth.

Adjust the Plan as Needed

Based on discussions, adjust milestones, evaluation criteria, or other aspects of the plan.

Concrete Actions:

  • If a milestone is repeatedly missed, break it into smaller, more manageable steps.

  • If new challenges arise, incorporate them into the plan with strategies to overcome them.

  • If the feedback indicates skill improvement, consider raising the bar for subsequent milestones.

Set Goals for the Next Check-In

Before concluding the check-in, set specific objectives to be achieved by the next check-in. This keeps the momentum going and provides a clear focus for the coming period.

Example: If during a check-in you realize that you have been consistently missing your milestones, it may indicate that your initial plan was too ambitious. Setting more realistic goals for the next check-in can help balance ambition with achievability.

Document the Check-In

Keep a record of what was discussed during the check-in, including any adjustments made to the plan, and the goals set for the next check-in. This documentation can help monitor progress over time and ensure accountability.

Exercise: Self-Reflection Journal

Keep a journal to document your thoughts, achievements, and challenges between check-ins. Reflect on how close or far you are from achieving milestones, and what might be causing any discrepancies.

Relevance: This exercise helps to maintain a continuous engagement with one’s progress, even between check-ins. It serves as a tool for self-awareness and can be particularly insightful in identifying instances of Dunning-Kruger or Impostor Syndrome.


  • "The Making of a Manager" by Julie Zhuo: This book includes insights on how to conduct effective check-ins.

  • "Radical Candor" by Kim Scott: Offers guidance on how to have honest and helpful conversations.

  • Agile project management tools like Jira or Trello for tracking progress.


Regular check-ins are a pivotal element of any successful development plan. They not only provide the necessary structure for continuous progress but also facilitate a realistic understanding of one’s abilities and achievements. Especially in the context of cognitive biases such as the Dunning-Kruger effect and Impostor Syndrome, regular check-ins can function as an external reality check. This, in turn, helps individuals calibrate their self-assessment and progressively grow in alignment with their goals.

As an ongoing process, it’s crucial to remember that learning and development are dynamic. Staying adaptable and open to change is imperative for true growth. This leads us to the next vital step in this series, which is milestone adjustment. This step focuses on the significance of allowing milestones to be dynamically adjusted based on feedback and evaluations and encourages individuals to maintain flexibility in their learning paths.

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