Shift From Time Optimism to Realistic Optimism for Ambiguous Leadership
TL;DR
- Leading in ambiguity requires shifting from a "time optimist" mindset to a "realistic optimist" by prioritizing strategic conversations and aligning them with long-term vision, not just immediate tasks.
- Defining success in shorter, achievable timeframes (12-24 months) provides measurable milestones that build confidence and ensure progress toward larger, multi-year strategic goals.
- The urgency to achieve a legacy within a finite career necessitates focusing energy on high-impact priorities that will have residual effects beyond one's tenure.
- Effective leadership in complex environments involves initiating strategic alignment with collaborators, recognizing that gaining buy-in and execution requires both quality conversations and sufficient quantity.
- Organizational culture change is a multi-generational effort, demanding patience and a realistic understanding that significant shifts take time, similar to individual habit formation.
- When managing managers, the leader's focus must shift from personal task completion to ensuring the work gets done through effective delegation and prioritization of strategic initiatives.
Deep Dive
A leader managing managers for the first time faces a critical challenge in setting team goals when external factors and future leadership create inherent uncertainty. This situation demands a shift from reactive planning to proactive, realistic optimism, focusing on establishing clear, shorter-term milestones aligned with a long-term vision to ensure sustained impact beyond immediate constraints.
The core tension for leaders in ambiguous environments lies in balancing the impulse to act with the need for clarity, particularly when their own career timelines create a sense of urgency. This leader, Mo, grapples with setting pace and measuring progress for multi-year, collaborative goals, exacerbated by an interim organizational leadership. The implication is that attempting to define success solely through distant, multi-year objectives in such fluid conditions leads to frustration and a feeling of inadequacy. The solution involves reverse-engineering the ultimate vision into achievable, shorter-term milestones, thereby creating a tangible path for progress and a more realistic definition of "enough." This approach allows for agility, accommodating potential shifts in institutional strategy while maintaining forward momentum.
The second-order implications of this leadership challenge are profound. When leaders are uncertain about timing and pace due to external dependencies, they can become paralyzed by the sheer scope of their goals, leading to a "holding pattern" that saps energy and delays progress. This uncertainty also impacts personal confidence, as the leader questions the efficacy of their time allocation. The critical insight is that leadership in such situations requires embracing ambiguity not as a barrier, but as a context for strategic action. By adopting a "realistic optimist" mindset, leaders can acknowledge present limitations while holding onto future vision. This involves prioritizing strategic conversations and relationship-building, understanding that quality and quantity of collaborative efforts are both crucial. For this leader, her urgency is driven by a finite career timeline, framing the challenge as creating a lasting legacy. This reframes the question from "am I doing enough now" to "is what I'm doing aligned with the longer-term vision and impact." The ultimate takeaway is that effective leadership amidst uncertainty hinges on breaking down large, distant goals into manageable, shorter-term objectives, fostering progress and confidence by focusing on alignment and impact rather than immediate, exhaustive achievement.
Action Items
- Create 12-24 month success milestones: Define 2-3 measurable outcomes for strategic initiatives to track progress and assess "enough" work.
- Draft strategic initiative framework: Outline 3-5 core components for new initiatives to ensure alignment with institutional priorities.
- Implement 4-5 weekly hours for strategic conversations: Block dedicated time to initiate alignment discussions with key collaborators.
- Measure collaborator impact on timing: For 3-5 key initiatives, quantify the influence of external partners on project timelines.
- Develop realistic optimism approach: Integrate future vision with present capacity by defining achievable steps for strategic goals.
Key Quotes
"We are meeting because there are some goals we have as a team that cannot be accomplished in a single year or a single semester they are going to take years of effort and work they're also going to take multiple collaborators our team cannot do it alone so we're relying on so many partnerships and collaborations and so that is a lot to keep track of and also to know what is the right pace you know what is the right amount to get done in one year toward a goal that i mean i can set a timeframe on it and say we want to have this done in three years but some of it is outside of our control because of all these multiple collaborators and so it's hard to know what is the right pace to do this work what is the right timeline to even project and guess might be the right time to allow us to start to achieve some of these goals and what is the right allotment of my time so this is the first time that i have been in this more strategic role as opposed to just doing and managing and so i'm just still trying to figure out what is the right allotment of my time what is the right timeframe to put on these goals and how do we know if we're measuring progress in the right way these are the questions that i struggle with almost daily"
The leader, Mo, articulates a core challenge: setting and pacing long-term, collaborative goals in a role that requires strategic thinking rather than direct execution. Mo struggles with determining the appropriate pace and timeline for these goals, especially when external collaborators and shifting institutional priorities create uncertainty. This highlights the difficulty of managing complex, multi-year objectives when progress is not solely within one's control.
"I think the question that you asked much earlier in the conversation just made me realize i teach people how to do this every day and yet and yet right if we would only listen to our inner teacher and yet oh it's the challenge that i've been struggling with"
Muriel Wilkins points out Mo's realization that she possesses the knowledge she seeks, as she teaches similar principles to others daily. This quote underscores the common human tendency to externalize solutions or struggle with applying learned principles to one's own situation. Mo's challenge lies in internalizing and acting upon the very strategies she advocates for.
"So what you're struggling with is making a choice right but why is making a choice hard for you i think because there is so much that we could be doing there is so much that we already do and i don't want to stop doing those things but yet i have the appetite for us to do more and i have never a team who i work with i learned a phrase from her that i'm a time optimist she is a time realist it's a being a time realist versus a time optimist i'm a time optimist and so i think that there should be more time to do more and there should be more opportunity to do more as we try to serve our students in the best possible way and a time realist would say you got to make a choice there's only so many things you can do because there isn't enough time so the time optimist that i am doesn't like that answer and doesn't want to hear that answer wants to continue to just push ahead and to try to keep adding more and more which is unrealistic"
Muriel Wilkins identifies Mo's core struggle as making choices due to her "time optimist" perspective, which leads her to believe more can be accomplished than is realistically possible. Mo's desire to do more and her reluctance to stop existing activities create a conflict with the finite nature of time. This highlights the tension between ambition and the practical constraints of resource allocation.
"So 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 yes so when we frame it that way how does that inform where you should be spending your time does it inform it any differently"
Muriel Wilkins reframes Mo's challenge from "how to pace goals" to "what to prioritize for lasting impact," especially given Mo's finite career timeline. This shift in perspective encourages Mo to focus her energy on activities that will create a residual effect beyond her tenure. The question prompts Mo to consider how this new framing influences her decision-making regarding time and effort allocation.
"I think enough looks like defining success maybe in smaller chunks so that it's easier to know yes this was enough like we we were able to define what success would look like in year one and either we did or we came close i think in a way by making the time frames smaller instead of realizing that the time frame is eight to ten years like figuring out what would success look like in 12 to 24 months what could we call that if we get considered a win if we were able to do x within 12 to 24 months i think that would be more helpful than trying to have this very large goal that has a very long time frame because it's hard to know within a shorter time frame was it enough did we get anything done if you're constantly looking out so far ahead"
Mo articulates a breakthrough in defining "enough" by suggesting success should be measured in smaller, more manageable chunks rather than a distant, overarching goal. By breaking down long-term objectives into 12-24 month milestones, Mo believes it will be easier to assess progress and determine if sufficient effort has been made. This approach aims to reduce the feeling of being overwhelmed by the vastness of the ultimate goal.
Resources
External Resources
Books
- "CEO Excellence" by McKinsey & Company - Mentioned as the source of the framework "CEO for All Seasons."
People
- Muriel Wilkins - Host of the podcast "Coaching Real Leaders."
- T-Nehisi Coates - Author mentioned in relation to his writings on the "march towards justice."
Podcasts & Audio
- HBR On Leadership - The podcast series featuring this episode.
- Coaching Real Leaders - The specific podcast series from which this episode is drawn.
Other Resources
- CEO for All Seasons - A framework for navigating leadership phases.
- Realistic Optimism - A concept discussed as a balanced approach to leadership.