Dear Yogesh,
I serve as senior leaderl for a complex global organization. One of my direct reports has been with me since my previous company, and she has consistently been outstanding. She began her journey as an admin, progressed to a paralegal role, and—with my encouragement—successfully completed law school and passed the bar. She is now a staff attorney.
She remains highly reliable, responsive, and skilled at building relationships across business units. She also demonstrates strong judgment in knowing when to escalate issues.
Recently, I encouraged her to present a report she led to our executive team. Unfortunately, things didn’t go as expected. She repeatedly postponed rehearsal sessions, citing legitimate work pressures, and despite multiple requests, never shared a draft of her presentation in advance.
On the day of the presentation, she unexpectedly called in sick—something she has never done before—and asked me to present on her behalf. Her deck was solid, though I had to make some last-minute adjustments to tailor it for the audience.
Since then, I’ve tried to discuss the situation with her, but she seems to be avoiding the conversation.
I believe she has tremendous potential—even the capability to step into my role one day or become a general counsel elsewhere. However, to grow, she will need to become comfortable presenting to senior leaders. At present, she struggles even in smaller team settings.
How can I support her in overcoming this barrier? Am I pushing her too far?
Tushar
Dear Tushar,
You may be asking the wrong question.
While you’ve clearly been a supportive and encouraging leader, it’s possible that you are envisioning a future for your employee that she may not yet see for herself—or may not feel ready to pursue. It’s also possible that, as a highly self-sufficient performer, she isn’t accustomed to asking for help and may not even know how to begin.
Her behavior—avoidance, delays, reluctance to seek support, and ultimately stepping away at the critical moment—strongly suggests a deep discomfort, possibly even a fear of public speaking. For individuals who are used to excelling, confronting an area of weakness can feel especially daunting.
In the SLII® framework, learning any new skill follows a progression. Individuals often begin as enthusiastic beginners, then encounter challenges and become disillusioned learners. With time and support, they evolve into capable but cautious contributors, and eventually into confident, self-reliant achievers.
In this situation, it’s possible that you applied a leadership approach suited for someone at a more advanced stage—when, in fact, she may still be in the early or middle phases of development in this specific skill.
The key now is to have an open and direct conversation. While she may be avoiding it, it’s important that you gently but firmly create the space to talk. Let her know you want to understand what happened and explore her career aspirations.
During that conversation:
- Reassure her that her growth path is her choice, and she won’t be judged either way
- Ask her what she truly wants for her future
- Be ready to offer support aligned with her comfort and readiness
If she does want to grow in this area, you can co-create a gradual development plan—starting with low-stakes opportunities and building up over time. Encourage her to present to peers first, then smaller leadership groups, and eventually larger audiences as her confidence improves.
You might also suggest structured support, such as joining Toastmasters International or working with a coach who specializes in presentation skills.
Ultimately, the only way to truly understand what’s going on is to ask—and to listen without judgment.
Your role is to continue being her advocate and supporter, not to shape her into a version of success that reflects your expectations. When you respect her pace and choices, you create the conditions for her to grow authentically—and sustainably.
Best wishes,
Yogesh