HBR On Leadership

Episode: Setting Goals for Your Team When the Path Isn’t Clear
Date: December 10, 2025
Host: Amanda Kersey
Coach: Muriel Wilkins
Guest ("Mo"): Pseudonym for a higher ed leader transitioning to managing managers

Overview: Navigating Ambiguous Times as a New Leader of Leaders

This episode of "HBR On Leadership" features a real coaching session with “Mo,” an experienced higher education leader facing new challenges: for the first time, she is a manager of managers in a rapidly changing organization. The central theme is how to set and pace goals for her team amid strategic ambiguity (uncertainty in upper-level direction and frequent leadership changes), all while keeping her own and her team's actions aligned for long-term impact.

Mo and executive coach Muriel Wilkins explore how to plan, prioritize, and avoid paralysis in the face of uncertainty, balancing action with adaptability. The conversation evolves from tactical scheduling questions to deeper reflections on legacy, impact, realistic optimism, and leading through ambiguity.

Key Discussion Points & Insights

1. The Challenge: Setting Team Goals When Strategy Is Unclear

• Recent Change: Mo’s role expanded after an organizational restructure—she’s managing managers for the first time, with multiple departments now reporting to her ([02:10]-[03:04]).
• Current Reality: Mo’s ambitious, multi-year goals (e.g., changing institutional culture for student readiness) depend on buy-in from many collaborators across campus ([03:56]-[05:37]).
• Her Main Questions:
  • What’s the right pace or time frame for long-haul goals?
  • How should she allocate her own time?
  • How can she measure progress when outcomes are far in the future?

2. Wrestling with Pacing, Ownership, and Control ([05:55]-[08:42])

• Mo’s Uncertainty: Lacks confidence about whether she’s structuring her time and her team’s time “the right way.”
• Coach’s Insight: “You’re looking for the formula...I don’t know if there is a formula. You’ve gotta create your own, and it’s a hypothesis.” (Wilkins, [07:53])

Reverse Engineering from Outcomes

• Parallels to Student Advising: Mo helps students map out long-term success by breaking it down ("reverse engineering"); the same logic applies to team/institutional goals ([08:27]-[09:11]).
• Actionable Step: Paint a clear picture of future success and work backwards to identify milestones, partnerships, and actions needed ([09:20]-[10:15]).

3. Leading in a Holding Pattern vs. Making Progress ([10:34]-[16:05])

• Ambiguity Source: Organizational leadership in flux—Mo’s division is between permanent leaders, making strategic priorities uncertain ([10:59]-[11:29]).
• Wilkins' Choice Framework: Mo must decide—stay in a holding pattern until new direction comes, or move ahead with provisional plans knowing they may need to pivot ([13:19]-[15:23]):
  • “You can’t be in a holding pattern and head towards your destination at the same time. It’s physically impossible.” (Wilkins, [13:53])
• Mo’s Decision: Lean towards proactive planning—even if new leadership changes the direction, she’s ready to adjust ([14:30]-[15:16]).

4. Collaborators, Buy-In, and Managing Dependencies ([18:39]-[24:06])

• Dependency Reality: Key collaborators have autonomy; their buy-in is crucial, and timing is largely outside Mo’s control ([18:42]-[19:34]).
• Coach’s Shift: Focus not just on how many collaborative conversations Mo has, but the quality and “alignment” created ([22:48]-[23:54]):
  • “Alignment, gaining alignment, is a function of both quality and quantity, with probably a higher index on quality.” (Wilkins, [23:54])
• Tactical Advice: Instead of cramming conversations into busy weeks, re-prioritize strategic relationship-building as a key leadership function ([29:34]-[29:53]):
  • “If strategic planning and the strategic conversations are your priority, it should be the reverse. That should be in your calendar. And then you’re looking to squeeze in the other stuff.” (Wilkins, [29:30])

5. From Time Optimist to Realistic Optimist ([36:25]-[39:00])

• Mo’s Self-realization: She describes being a “time optimist” (always believing more can fit in), versus a colleague’s “time realist” approach ([36:13]-[36:26]).
• Coach’s Synthesis: The path is “realistic optimism”—hold an ambitious vision, but make choices within time’s real constraints. The leader’s calendar is the present (realism) and the vision is the future (optimism) ([38:47]-[39:00]):
  • “The reality part is in the present and the optimist part is in the future...They’re not mutually exclusive.” (Wilkins, [38:47])

6. Prioritization, Milestones, and Defining Success ([40:18]-[56:36])

• Break the Problem Down: Big, ambiguous goals need to be translated into shorter timeframes and measurable milestones ([50:05]-[51:11]).
• Practical Step: Identify what would count as “success” in the next 12–24 months, not just at the final vision ([55:44]-[56:23]):
  • “Trying to make smaller goals and name what those milestones are is just going to be so helpful...The phrase ‘boiling the ocean’ comes up—of course I want to boil the ocean...But just remembering that you can’t and figuring out, okay, what could be done in 12 months and...then measure the path, measure success in those smaller time frames.” (Mo, [55:44]-[56:33])
• Legacy & Long-term Impact: Mo admits urgency stems from the finite time left in her career—impact must outlast her tenure ([44:32]-[46:33]):
  • “The formula you’re solving for is: what should I be spending my energy on in the next couple of years to ensure that it has impact beyond those years?” (Wilkins, [46:20])
• Letting Go of Endless ‘Doing’: The real mark of leadership at scale is enabling others and building systems, not just personal effort ([37:45]-[38:09]).

Notable Quotes & Memorable Moments

• “We are meeting because there are some goals we have as a team that cannot be accomplished in a single year or semester...it's hard to know what is the right pace to do this work...and how do we know if we're measuring progress in the right way? These are the questions I struggle with almost daily.”
  — Mo ([03:56]-[05:37])

• “You’re looking for the formula...I don’t know if there is a formula. Mo. I think you gotta create your own formula, and it’s a hypothesis.”
  — Muriel Wilkins ([07:53])

• “If strategic planning and the strategic conversations are your priority, it should be the reverse. That should be in your calendar. And then you’re looking to squeeze in the other stuff.”
  — Muriel Wilkins ([29:30])

• "There is such a thing that is known as a realistic optimist.... The optimism part: having a vision that you’re pushing forward towards… The realistic part is what can be done within the context."
  — Muriel Wilkins ([36:26])

• “What is more important to you? That you’re doing the work or that the work is getting done?”
  — Muriel Wilkins ([37:45])

• “Every student, 100% of them. That’s why this is the top priority.... if we get it right, then every student going forward is impacted.”
  — Mo ([47:08]-[47:21])

• “Maybe instead of asking yourself, ‘Am I doing enough?’ The question could be, ‘Am I doing what’s aligned with the longer vision?’ ... Are you doing and is it aligned? That's it.”
  — Muriel Wilkins ([51:49]-[52:09])

Timestamps for Key Segments

• [02:10] Mo describes her expanded role and new challenge of managing managers
• [03:56] Mo shares her struggles with ambiguous, long-term goals and pacing
• [07:53] "There is no formula"—discussion of leadership as hypothesis testing
• [13:53] Wilkins’ holding pattern vs. moving forward analogy
• [23:54] “Alignment is a function of both quality and quantity” in collaborations
• [29:30] Advice to schedule priorities before filling the calendar
• [36:26] Introduction of the “realistic optimist” approach
• [46:20] The real legacy question: energy for impact beyond Mo’s tenure
• [51:49] Shift from "enough" to "alignment" with vision
• [55:44] Mo’s practical takeaway: smaller, well-defined milestones

Flow and Tone

The tone is reflective, candid, and supportive. Mo brings vulnerability (“am I doing this right?”), and Wilkins responds with empathy, directness, and new mental frameworks—often using higher-ed and aviation analogies to help Mo see her own situation more clearly. The energy vacillates between the tactical ("how many conversations should I have per week?") and the philosophical (leadership, legacy, choosing priorities amid limited time).

Guidance for Listeners

If you’re leading a team in times of ambiguity, or you’ve newly scaled into ‘managing managers,’ takeaways from this episode include:

• Reverse engineer your success: Start with the desired outcome, break it into tangible milestones, and work backward
• Replace “enough” with “aligned”: Periodically check if your work (and your team’s) aligns to the long-term vision—even if you aren’t accomplishing everything
• Schedule your priorities: Block time upfront for the work that will move the needle, rather than squeezing it in around urgent tasks
• Balance optimism and realism: See yourself as a “realistic optimist” who can hold an ambitious vision while making tough weekly choices
• Embrace the limitations of control: Prioritize partnership quality, not just quantity, and let go of things you genuinely cannot influence
• Legacy is about systems and culture: Focus your efforts on work and alliances that will outlast your span of control or tenure

Final Reflection

Mo leaves the session with a framework for action and a sense of permission: prioritize short-term milestones that add up to long-term impact, schedule accordingly, and accept that not everything can (or should) be accomplished at once. Leadership, especially in uncertain times, is less about the “perfect formula” and more about learning, adapting, and empowering others for results you might not even see.

Notable Quote for Inspiration:
“What you’re doing with these kids in school, you’re planting the seed...you might never see the impact, but you have to trust that it’s going to be there—that you’ve done what you needed to do in alignment with them being able to be successful in the world as alums.”
— Muriel Wilkins ([53:39])