Coaching Real Leaders – Episode Summary

Episode: How Do I Handle So Much Organizational Uncertainty?
Host: Muriel Wilkins (Harvard Business Review)
Air Date: November 3, 2025
Podcast Theme: Leadership coaching in moments of organizational change

Overview

This episode of Coaching Real Leaders captures an intimate, honest coaching session between host and executive coach Muriel Wilkins and "Maggie," a long-tenured leader at a company transitioning from startup to scale. Maggie’s core struggle is navigating career uncertainty caused by a rapidly shifting organizational structure, new leadership, and changing role expectations. The episode explores how leaders can find steady ground, redefine their value, and proactively shape their own trajectory during turbulent times.

Key Discussion Points & Insights

1. Maggie’s Background and the Emerging Challenge

[01:21 – 04:03]

• Maggie has been with her company since its early startup days, rising through multiple roles as the organization grew.
• The company is now entering a new era with significant scaling, new executive leadership, and a shift toward specialized roles.
• Maggie questions her fit and future:

  "Am I who this organization needs long term? Is there a place for me in this organization long term?" – Maggie, [01:59]

• She feels uncertain due to vague expectations, changing priorities, and being less “in the room” than before.

2. Transition from Generalist to Specialist Roles

[04:03 – 08:38]

• Historically, Maggie advanced by taking on whatever the company needed—“raising her hand” for new, undefined challenges.
• Now, there’s more value placed on specialization, and fewer ambiguous spaces to fill.
• She notes she’s not receiving much feedback from new leadership, fueling her uncertainty:

  "I'm not sure, am I hitting the mark, am I not? …I'm not getting that feedback from new leadership that I don't know well and that doesn't know me well." – Maggie, [07:07]

3. The Nature of Organizational Uncertainty

[08:28 – 10:11]

• Muriel reframes the lack of clarity:

  "There's a lot of change and people discovering right now because they are new to the company, which is really not personal." – Muriel, [09:11]

• The organization, like a patient at the doctor, is being diagnosed before new direction can be set.

4. Coping on the “Precipice” – Grounding Strategies

[10:55 – 15:33]

• The discussion introduces the metaphor of standing “on the precipice.”
• Muriel asks Maggie what would give her stronger footing during this interim period:
  • Learning how larger, scaled companies work
  • Understanding the new leadership’s vision (which is still emerging)
  • Developing an internal metric for success—measuring progress without relying on external validation.
• Muriel’s actionable suggestion: Set short-term, self-defined goals to create a daily/weekly North Star:

  "Are my two feet still on the ground? …What would make this week successful?" – Muriel, [14:20]

5. Focusing on the Controllable—Short-Term Framing

[15:33 – 16:44]

• Maggie acknowledges she is usually future-oriented and strategic but must now bring things back to the present and operate in “shorter-term frameworks,” e.g., weekly goals and visible, trackable wins.

6. Redefining Value: From “Doing It All” to Specialization

[20:18 – 25:02]

• Muriel challenges Maggie to articulate what she wants if given the chance to design her ideal role.
• Maggie reflects she’s always derived value from being the go-to person for everything, but this no longer aligns with the company’s needs.
• Muriel prompts her to redefine “value” outside of taking on more and more:

  "If up until now you've defined your value as doing it all, what could be the new way that you could define your value?" – Muriel, [22:24]

7. Identifying Her Unique “White Space” and Building Confidence

[25:02 – 32:29]

• Maggie recognizes areas where she’s one of few with specific expertise—her “white space.” She admits letting go of responsibility elsewhere will be difficult but necessary.
• Muriel guides her to catalog both what she knows and her learning agility:

  "The confidence doesn't come from whether you know something or don't know it. The confidence comes from whether you believe you have the ability to learn those things." – Muriel, [32:24]

• Maggie feels energized by learning and agrees to shift her focus to both her known strengths and growth areas.

8. Leveraging Relationships and Ecosystem Support

[36:14 – 38:21]

• Maggie shares her mixed feelings about confiding in peers (owing to trust concerns), and her limited relationship-building with newcomers.
• Muriel encourages being more intentional and strategic about relationship-building and considering presenting her own vision to new leadership—even if it feels risky.

9. Risk, Action, and Accepting the Range of Outcomes

[39:04 – 44:13]

• Maggie hesitates to offer bold recommendations for fear they’ll be misaligned or highlight her inexperience.
• Muriel reframes: The risk exists regardless, so why not be proactive? She encourages Maggie to own her narrative and demonstrate leadership by proposing focused contributions.
• The session explores the “worst case” of needing to seek a new role; Maggie feels overwhelmed by this but sees it as manageable and part of honoring herself and her journey.

10. Integrating Learning and Action—The “Precipice Era”

[45:59 – 51:08]

• Muriel reiterates the power of focusing on what one can control right now—measuring progress, documenting changes, focusing on a few high-value areas, and building relationships.
• They name and accept the “precipice era” as a valid, even fertile, leadership phase:

  "So much can be done in the precipice era. …There's so much to be done in the staying." – Muriel, [50:49]

• Maggie leaves with a framework for goal-setting, self-reflection, and an acceptance of the ambiguity.

Notable Quotes and Memorable Moments

• Defining Uncertainty:

  "There's a lot of I don't knows." – Muriel, [08:01]

• Short-Term Focus:

  "What would make today a success? What would make this week successful?" – Muriel, [14:20]

• Letting Go:

  "If up until now you've defined your value as doing it all, what could be the new way that you could define your value that isn’t I do it all?" – Muriel, [22:24]

• Growth Mindset:

  "The confidence doesn't come from whether you know something or don't know it. The confidence comes from whether you believe you have the ability to learn those things." – Muriel, [32:21-32:24]

• The Power of Agency:

  "What I'm advocating for is to see that you have choice and you have different paths you can walk down." – Muriel, [40:46]

• Purpose and Self-Honor:

  “In what way do you honor yourself in whatever next chapter that is.” – Muriel, [45:24]

• The Value of Staying:

  "So much can be done in the precipice era. …There's so much to be done in the staying." – Muriel, [50:49]

Important Timestamps

| Segment | Time | |----------------------------------------------|-----------| | Maggie’s career context and challenge arises | [01:21] | | Discussion of changing company needs | [04:03] | | The “precipice” metaphor introduced | [10:55] | | Self-defined success & short-term focus | [13:31] | | Redefining value: specialization needed | [21:37] | | Courage & confidence in ambiguity | [32:21] | | Relationship building in flux | [36:14] | | Facing worst-case scenario | [43:00] | | Acceptance and next steps | [47:41] | | The power of the “precipice era” | [50:49] |

Actionable Takeaways

• Embrace Short-Term Wins: Define and measure success week-by-week to sustain confidence and a sense of grounding amidst flux.
• Redefine Value: Reflect on shifting from a generalist “do it all” mode to identifying and leaning into specific high-needs (“white space”) areas.
• Catalog Strengths & Growth Areas: Write down both what you know well and areas where you can learn, reinforcing both expertise and growth mindset.
• Intentionally Build Relationships: Reach out purposely to new and established colleagues, and consider sharing your emerging vision even when unsure.
• Take Agency: Instead of waiting for clarity, create it—narrate your value, propose focused roles, and “walk off the precipice” by choosing a proactive path.
• Accept the Precipice: Honor the ambiguity and use the transition time as a real phase for learning, experimenting, and personal clarity.

Tone & Final Reflection

The episode’s tone is empathetic, practical, and empowering. Maggie’s vulnerability is matched by Muriel’s nuanced questioning and steady optimism. The “precipice” is acknowledged as both daunting and full of possibility, and the session closes with a sense of strength found in small, consistent action and authentic self-leadership—regardless of organizational uncertainty.