3 min read

Successful Leadership Transitions: Self-coaching Tool #4: Evaluate

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If you are a “next level” leader who is rising up into a role with higher levels of leadership responsibility, you must adopt new ways of thinking and acting, and more important, let go of old ways. This is fourth in a series describing 6 common pitfalls and key practices every emergent leader must pick up to cement their success based on best practices rolled into a framework called Rise Up™ Leadership Transitions.


RISE UP™:  RethinkInfluence.  Stretch.  Evaluate. Unleash. Prioritize.

Common Pitfall: 

No systematic method to monitor and measure progress; operate in a vacuum and under your own assumptions of success


Vulnerability to failure, slow to course correct, too easily swayed by louder voices; over attend to minority opinions, inability to track trends

Rise Up™ Strategy: 

Evaluate your progress through quality feedback

Feedback is a complex and vital topic to successful role transitions and when done poorly, often one of the biggest reasons for failure or derailment.  One complexity of unplanned transitions is   the lack of quality feedback provided, early and often in the transition.  Most of the time, there are no structured methods sponsored by the boss/company to help the transitioning leader reflect on and discuss their transition separate from their day to day responsibilities.  The void of feedback contributes to being too slow to react to correcting a direction you are going, wasting time and leaving higher priorities unattended to.

The second pitfall relates to the mindsets of the leader.  Many transitioning leaders are reluctant to ask for feedback for fear of looking insecure or weak to their boss or team.  Even when some leaders do receive feedback, their biases can filter the feedback, convincing them that they are doing better than they actually are.  It can also be easy to over weigh a comment from a trusted colleague about an opinion but not check that it is a theme shared by others. 

Milestone Meetings: 

Critical to Evaluating Your Progress:

Use this as a simple framework for how to prepare for a Milestone Meeting with your boss at 1, 3, 6 and 9 months to provide structure for focused, substantive discussions during your transition; to review progress, share feedback, and navigate challenges. 

  • What transition objectives have you accomplished ?(since the last Milestone)
  • What could you have done more effectively (since the last Milestone)?
  • What challenges are you currently experiencing? What will you do differently to manage them? 
  • What stakeholder issues do you need help strategizing on?
  • What resources do you need support with to be successful?
  • Provide feedback to Boss regarding effectiveness of their support since last Milestone. What do you need from him/her in the next 3 months?


Don’t succumb to sink or swim, go it alone transitions. 

Check out these blog posts to create successful leadership transitions for you and your company!

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