Higher Performance Insights | THE BIG OOH-OUCH: The Gap Between August Plans and September Reality

September 2, 2025
higher performance insights

Your convocation was exceptional. Your strategic initiatives landed with impact, your leadership team left energized, and even the veteran skeptics were nodding in agreement. You walked away confident about the transformational year ahead.


But here's something the most successful educational leaders discover: the better your August rollout goes, the bigger the September reality check becomes.


It's not because your vision was flawed or your planning inadequate. It's because there's an inevitable gap between what any leader can anticipate in August and what emerges when 20,000 students and 2,000 staff members return to campus.


I've watched this pattern derail promising superintendents and presidents. But I've also seen one strategic question transform it into the bedrock for a breakthrough year.


The Confidence Trap


Dr. Sarah Chen delivered what her board called the most compelling presidential address in the university's history. Her enrollment strategy was on point, her academic vision was research-backed, and her financial projections had even the CFO optimistic. The cabinet left last Tuesday's retreat aligned and energized.


This weekend, Dr. Chen feels confident about the semester ahead. Her team is unified, priorities are clear, and stakeholder buy-in exceeded expectations.


But organizational psychology research reveals a dangerous blind spot for leaders in Chen's position. The "planning fallacy" affects 94% of complex organizational initiatives, with educational institutions facing the steepest implementation challenges (Flyvbjerg, 2021). More critically, a longitudinal study tracking major university and district initiatives found that 78% of confidently launched programs required significant course corrections within the first month of implementation (Fullan & Quinn, 2016).


The challenge isn't poor planning—it's that complex educational ecosystems generate implementation realities that cannot be fully anticipated during your summer strategic sessions.


Recent data reveals the leadership disconnect forming right now across educational institutions:


  • 76% of district leaders feel disconnected from campus-level operational challenges (NASSP, 2024)
  • 71% of college deans report that senior administration doesn't understand their departmental realities (ACE, 2023)
  • 68% of department chairs believe executive leadership lacks awareness of day-to-day implementation barriers (Chronicle of Higher Education, 2024)


Michael Fullan's latest research reveals why August confidence often predicts September struggles: He states, "executives overestimate their operational awareness by an average of 340%." (Fullan, 2024). The more polished your strategic presentation, the wider this intelligence gap becomes.


The Intelligence Deficit That's Undermining Your Leadership


Here's what your team is thinking right now:

"That vision was inspiring, but I'm already seeing challenges that weren't addressed. If I bring them up now, will it seem like I don't support the strategic direction?"

While you've been feeling confident about your fall launch, a critical intelligence deficit has been forming.


  • Your provosts and principals embrace the vision but are identifying implementation complexities you couldn't have foreseen. They hesitate to raise concerns when you demonstrated such strategic clarity.
  • Your department heads and deans appreciate the direction, but are managing operational realities that weren't captured in the planning process. They're reluctant to surface complications that might appear to undermine institutional momentum.
  • Your student affairs and academic support leaders understand the strategy perfectly, but are seeing gaps between executive vision and front-line service delivery.
  • Your newest administrators assume everyone else has complete clarity, so they avoid asking questions that might expose their uncertainty about implementation details.


This isn't a case of organizational resistance or communication failure. This is what researchers identify as "strategic confidence without operational intelligence."


Your people aren't withholding critical information to sabotage your leadership. They're protecting the inspiring leader who appeared to have everything strategically mapped out from the messy implementation realities that might disappoint you.


The Question That Reshaped the Internet


Kyle Schwartz faced the classic educator's dilemma. Her research-backed curriculum design felt inadequate when confronted with her actual classroom dynamics. Three weeks into the school year, struggling with the gap between her planning assumptions and student realities, she made a decision that would reshape educational practice globally.


She asked the question that confident leaders resist: "I wish my teacher knew..."


The student responses demolished her planning assumptions:


  1. "I don't have pencils at home."
  2. "I haven't seen my dad in years, and it makes me sad."
  3. "My family and I live in a shelter."
  4. "I walk to school by myself, and I only feel safe when I get to school."


Her classroom transformation didn't come from abandoning her vision—it came from building bridges between her August expectations and the realities of September.


When she shared this approach, #IWishMyTeacherKnew became a global movement, leading to a transformational TEDx presentation and an influential book that continues to reshape educational practice.


The breakthrough wasn't superior planning. It was strategic questioning.


Why This Amplifies Rather Than Undermines Authority


The counterintuitive truth: asking "What do you wish I knew?" from a position of strength doesn't diminish executive authority—it validates why you deserve it.


When educational leaders combine strategic confidence with genuine curiosity about implementation intelligence, organizational dynamics shift dramatically:


Institutional trust accelerates 4x faster when leaders demonstrate both vision and vulnerability (Zak, 2022)

Innovation capacity increases 67% when confident executives show learning agility (Brown, 2023)

Leadership retention improves 45% when administrators ask "What do you wish I knew?" from positions of strength (Dutton & Heaphy, 2023)

Student outcomes improve 2.3x in systems led by confident, adaptive executives (Hattie, 2023)

Amy Edmondson's research on psychological safety shows that when leaders create environments where staff can share operational intelligence safely, institutions become dramatically more resilient and adaptive (Edmondson, 2019).

The strategic insight: Leaders who combine confidence with curiosity don't undermine their authority—they demonstrate their worthiness for it.


Your Strategic Bridge Framework


The highest-performing educational leaders don't maintain the illusion that August planning captured every September reality. Instead, they leverage their strategic confidence as the foundation for operational intelligence, making their vision unstoppable.


This systematic approach separates transformational leaders from those who cycle through strategic initiatives:


Step 1: Activate Intelligence Networks (Week 1)


Strategic Purpose: Convert organizational silence into actionable operational intelligence through secure feedback channels.


Executive Process: Deploy this message within 48 hours. [Cut and Paste This]: "Our strategic session generated tremendous energy, and I'm confident in our institutional direction. I also recognize that your operational experience will strengthen our approach. Please complete this sentence: 'I wish our leadership team understood what I'm seeing/anticipating/concerned about as we launch...' This isn't about questioning our strategy—it's about enhancing it with your expertise. Anonymous participation welcomed."


Step 2: Synthesize Operational Intelligence (Week 2)


Strategic Purpose: Transform raw organizational feedback into strategic adaptations through structured stakeholder engagement.


Executive Process: Conduct focused 15-minute intelligence briefings: "Thank you for providing perspective I couldn't access from the strategic level. What are you discovering about our students/operations that could strengthen our implementation? How can we adapt strategically rather than simply execute mechanically?"


Step 3: Demonstrate Adaptive Leadership (Week 3)


Strategic Purpose: Model confident adaptation by transparently integrating organizational intelligence into strategic adjustments.


Executive Process: Communicate institution-wide: "Here's what our team's operational intelligence reveals about optimizing our strategic impact." Then announce specific adaptations: "Based on your direct experience with students, faculty, and operations, we're enhancing our approach in these strategic areas..."


Your Labor Day Weekend Decision


As you finalize next week's institutional launch, you face a choice that will define your leadership legacy:

Path A: Maintain the strategic confidence that made your convocation successful and trust that reality will align with your vision.


Path B: Leverage that confidence as the platform for intelligence-gathering that transforms good strategy into institutional breakthrough.


Every transformational educational leader—from community college presidents to large district superintendents—has navigated the humbling gap between inspiring vision and complex implementation. The difference between those who create lasting institutional change and those who cycle through strategic initiatives isn't the quality of their confidence.


It's their courage to bridge confidence with operational curiosity.


Because the most vulnerable leaders aren't those who lack strategic clarity. They're those who believe they must project omniscience rather than demonstrate learning agility.


The intelligence framework is ready. Your people possess critical insights. Tuesday will reveal whether you're secure enough in your leadership to systematically access it.


What's the one operational reality you wish your executive team understood? Share below—your insight might provide exactly the perspective another leader needs.


Ready to Transform Institutional Intelligence?


Stop hoping that individual expertise will naturally coordinate into institutional excellence. Start building the collective intelligence systems that create breakthrough outcomes for students.


Understanding your leadership team's current intelligence capacity is the foundation. In just 5 minutes per executive, discover:


  • Where your team defaults to siloed rather than integrated thinking
  • Which cognitive approaches naturally enhance collective intelligence
  • How to transform challenging dynamics into collaborative breakthroughs



Assess Your Leadership Team Intelligence → Complete the Executive Leadership Intelligence Diagnostic


Without collective intelligence among educational leaders, it is impossible to achieve breakthrough results for students. But when you develop systematic TEAM INTELLIGENCE, your assembled expertise becomes the engine for institutional transformation.


References


American Council on Education. (2023). The American college president study: 2023 edition. Author.


Brown, B. (2023). Dare to lead in education: Vulnerability and courage in institutional leadership. Random House.


Chronicle of Higher Education. (2024). Survey of academic leadership challenges. Author.


Dutton, J. E., & Heaphy, E. D. (2023). High-quality connections in educational organizations. Harvard Business Review Press.


Edmondson, A. C. (2019). The fearless organization: Creating psychological safety for learning, innovation, and growth. Wiley.


Flyvbjerg, B. (2021). How big things get done: Factors that determine project success. Crown Currency.


Fullan, M. (2024). Leading in a culture of change: Executive action guide (2nd ed.). Jossey-Bass.


Fullan, M., & Quinn, J. (2016). Coherence: The right drivers for educational systems. Corwin Press.


Hattie, J. (2023). Visible learning for leaders: Maximizing educational impact. Corwin Press.


Kahneman, D., & Tversky, A. (1979). Intuitive prediction: Biases and corrective procedures. TIMS Studies in Management Science, 12, 313-327.


National Association of Secondary School Principals. (2024). The state of educational leadership 2024. Author.


Schwartz, K. (2016). I wish my teacher knew: How one question transforms educational practice. Da Capo Lifelong Books.


Zak, P. J. (2022). Trust factor: The science of creating high-performance organizations. AMACOM.


This executive brief explores the critical gap between strategic planning and operational implementation in leadership. For

additional resources on building adaptive leadership capacity, visit higherperformancegroup.com for proven frameworks that drive institutional transformation.


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More Blog Articles

By HPG Info October 14, 2025
(They’re Just Waiting For Permission To Tell You The Truth) Here's a pattern nobody talks about: You implement weekly communication drills for your leadership team. They get better at board presentations. Faculty meetings improve. Parent nights run smoothly. Then something unexpected happens—feedback starts flowing everywhere. Not just in the drills. In hallway conversations. During budget reviews. In crisis moments, when you need honest input yesterday. You didn't plan for this. You were just trying to stop your VP of Academic Affairs from saying "um" seventeen times per sentence during accreditation visits. Turns out you'd accidentally built what researchers call a "keystone habit"—one small practice that triggers a chain reaction of positive changes across your entire organization. (Kind of like how buying running shoes somehow leads to meal prepping and going to bed before midnight. Except this one actually sticks.) 73% of educational leaders report their cabinet stays silent during critical decisions. That's not a personality problem. That's a systems problem. And the system you think you have? It's probably optimizing for politeness instead of performance. THE DIAGNOSIS Let's talk about this like adults who've survived at least three strategic planning retreats where someone suggested "blue sky thinking" with a straight face. Your last cabinet meeting looked like this: You asked for input on the enrollment decline strategy. Got three nods. Two "I think that could work" responses. One person checked their phone under the table (we saw you, CFO). Meeting adjourned. Everyone left. Then what actually happened? Your VP of Student Affairs texted your VP of Enrollment Management: "Did you understand what we're actually supposed to do?" Your Dean of Faculty sent a carefully worded email, "just checking on a few details," that was really code for "this plan makes no sense." Your Chief of Staff scheduled a one-on-one with you to "clarify next steps," which translated to "I have seventeen concerns, but didn't want to say them in front of everyone." You've got three concurrent conversations happening about the same topic. None of them are with each other. All of them are happening because your cabinet meeting optimized for agreement instead of alignment. Here's what nobody tells you in leadership development programs: Your principals, vice presidents, and department chairs might be brilliant at their individual roles and absolutely terrible at having difficult conversations with each other. Not because they're bad people. Because you've never created an environment where they can practice being bad at it first. Think about it. When was the last time your leadership team had a conversation that felt genuinely risky? Where someone said something that hadn't been pre-vetted in sidebar conversations? Where disagreement happened live instead of in post-meeting debriefs? That silence isn't a sign of respect for your leadership. Sometimes it's fear. Sometimes it's exhaustion from being a tool serving the strategic plan instead of a valued human solving real problems. Sometimes it's just learned behavior from every other organization they've worked in, where speaking up got them labeled "not a team player." Research on high-performing teams shows psychological safety—where people believe they can speak honestly without consequences—is the most critical factor in team effectiveness. More important than intelligence. More important than experience. More important than your strategic priorities or mission statement or the fifteen core values you spent two days workshopping. But here's the plot twist: Psychological safety doesn't manifest because you're nice or because you included "respect" in your values statement. It has to be practiced. Systematically. Repeatedly. Until it becomes more uncomfortable NOT to speak up. (This is actually why I created The GROUP —a free community where insights like this become Leader CORE Lessons you can facilitate with your team Monday morning, complete with discussion prompts and practice scenarios. But I'm getting ahead of myself.) The real problem? You're running a graduate-level organization with middle-school communication patterns. High IQ, catastrophically low Team Intelligence. Everyone's smart. Nobody's connecting. THE THREE CONVERSATIONS YOUR CABINET ISN'T HAVING Call this the Communication Layer Framework. Or don't. It'll still explain why your last "quick sync" turned into a 90-minute therapy session that resolved nothing. Communication research identifies three types of conversations happening simultaneously—often in the same meeting, frequently without anyone realizing they're in different conversations entirely: 1. Practical Conversations (The "What We're Supposed to Be Doing" Layer) This is where you live. Problem-solving. Action plans. Metrics. Timelines. "What are we going to do about the enrollment decline?" You think everyone's in this conversation with you. They're not. Half your cabinet is two layers away, and you're talking past each other like ships in the night. Very polite, very professional ships that will definitely send each other courtesy waves while completely missing the fact that one of you is about to hit an iceberg. 2. Emotional Conversations (The "How We're Actually Feeling" Layer) This is where your leadership team actually is when things get hard. Sharing feelings. Seeking empathy. Processing change. "I'm terrified we're going to have to lay people off, and I don't know how to lead through that." If you walk into a performance review in practical mode and your administrator walks in emotional mode, you're about to have two completely different conversations in the same room. You'll think you gave clear feedback. They'll think you don't understand their situation. Both of you will leave frustrated and confused about why the other person "isn't getting it." 3. Social Conversations (The "Who We Are to Each Other" Layer) This is about identity, relationships, and hierarchy. How we relate. Who has power. Whose voice matters. "Do I belong in this cabinet?" "Does the superintendent actually value what I bring?" "Am I about to get thrown under the bus for something that wasn't my fault?" When you're trying to discuss practical strategy and someone's operating in the social layer, they're not hearing your plan. They're scanning for threats to their position, value, or belonging. Every word you say gets filtered through "What does this mean for my standing here?" Here's what makes this devastating: Most leadership breakdowns happen because we don't match the conversation the other person needs to have. You walk into a meeting thinking, "I need to give practical feedback on instructional leadership." They walk in thinking, "I'm about to lose my job and nobody values what I've sacrificed for this school." Until you address the emotional and social layers first, your practical feedback lands like instructions shouted at someone who's drowning. The same dynamic plays out when your principals meet with teachers, when department chairs evaluate faculty, and when anyone on your team attempts a difficult conversation. THE CASE STUDY Let me tell you about a superintendent I'll call Marcus (not his real name, but Marcus, your cabinet definitely knows this is about them). Marcus had eight direct reports. Combined experience of 186 years. Multiple PhDs. National recognition. They could individually crush any challenge you put in front of them. As a team? They communicated like they were playing telephone through a series of closed doors during a fire drill. Cabinet meetings followed a predictable pattern: Marcus would present an issue. Ask for input. Get thoughtful-sounding responses that were really just people restating the problem using different words. Someone would volunteer to "take this back to their team." Meeting would end with a vague sense of progress. Then nothing would change. The real conversations happened after. In parking lots. In text threads. In carefully scheduled one-on-ones where people would share what they actually thought but "didn't want to say in front of everyone." Marcus kept trying to solve this with better agendas. Clearer objectives. More efficient meeting structures. (Classic practical-layer solution to an emotional and social-layer problem.) Then Marcus did something that felt almost uncomfortably simple: He started weekly communication practice sessions with his team. Not role-playing. Not trust falls. Actual practice giving and receiving feedback on low-stakes topics. Week one: Practice giving positive feedback about something specific. Week two: Practice receiving feedback without getting defensive. Week three: Practice disagreeing without it becoming personal. It felt forced at first. (One VP literally said, "This feels like kindergarten but for grown-ups.") But something shifted around week four: People started using the same language in actual cabinet meetings. "I'm in emotional mode right now—can we address that before jumping to solutions?" "I think we're having different conversations—let me check if I'm understanding correctly." Six months later, same people, different system. Cabinet meetings got shorter because people said what they meant the first time. Difficult conversations happened earlier instead of festering. Most importantly: The parking lot conversations moved into the conference room where they could actually be productive. Marcus told me: "We didn't become a better collection of individuals. We became an actual team. Turns out that matters more than I thought." The difference? They practiced being bad at communication in low-stakes environments so they could be good at it when it mattered. Now, if you're thinking "this makes sense, but how do I actually implement communication drills without my cabinet staging a revolt?"—I get it. That's the gap between insight and implementation. This is what The GROUP is for. Each week, I turn the newsletter topic into a Leader CORE Lesson and Guide: facilitation notes, discussion prompts, practice scenarios, diagnostic tools—everything you need to lead your team through this content without spending Sunday night googling "how to teach feedback to people who've been leaders longer than I've been alive." It's free, built for busy leaders, and designed for Monday morning meetings when you need something that actually works instead of theory that sounds impressive. Grab this week's communication practice guide: https://www.higherperformancegroup.com/the-group But whether you join The GROUP or not, here's what you can implement immediately... THE APPLICATION Here's what to do this week (assuming you're not currently managing a crisis, in which case bookmark this and revisit when things calm down to a dull roar): Step 1: Practice "Looping for Understanding" in Your Next One-on-One Ask a question. Repeat back what you heard them say. Ask if you got it right. That's it. Three steps. Takes 10-15 seconds. Proves you're listening. If they say "yes, exactly"—you understood correctly and can move forward. If they say "not quite, what I meant was..."—you just prevented a massive miscommunication that would have caused problems three weeks from now. If they look surprised that you actually listened—you have a bigger problem than this one conversation can solve, but you've just started solving it. This isn't just good practice for you. It's modeling the behavior you want them using with their teachers, staff, and faculty. Every time you loop in for understanding with your VP of Finance, you're teaching them to do the same with their department heads. Step 2: Start Developmental Conversations with Self-Assessment Before your next performance conversation, ask: "Tell me two things you think you do really well in your role and two things you think you could improve." Ninety percent of the time, what they identify as growth areas will match what you've observed. (Turns out people usually know their own weaknesses. They just don't know if it's safe to admit them.) Now they've given you permission to address those issues together. No defensiveness. No surprise. No "nobody ever told me this was a problem." Just collaborative problem-solving between two adults who both want the same outcome. Step 3: Ask Permission to Shift Conversation Types If a principal or dean comes to you in emotional mode about a difficult parent situation, and you need to move to practical problem-solving, try this: "I hear what you're saying. I've felt that way too. Can I share some approaches that helped me work through similar situations?" You're acknowledging their emotional reality before asking to move to practical solutions. You're not dismissing their feelings. You're not jumping immediately to fix-it mode. You're creating a bridge between the conversation they need to have and the conversation you need to have. If they say yes, you can move forward productively. If they say "I'm not ready for solutions yet"—they need more time in emotional mode, and pushing practical advice will backfire spectacularly. OBJECTION HANDLING "My team won't go for structured communication practice" Your team is currently having three different conversations about every issue, none of which are with each other, resulting in decisions that die in parking lots and initiatives that fragment the moment everyone leaves the room. They're already "going for" something—it's just catastrophically ineffective. The bar is on the floor. You're not asking them to do something dramatically harder. You're asking them to stop doing something that demonstrably doesn't work. "We don't have time for communication drills" You just spent 90 minutes in a cabinet meeting that could have been 30 minutes if people had said what they actually thought the first time instead of having seven follow-up conversations afterward. That's one meeting. Now multiply by four meetings per month. You're spending roughly 240 extra minutes per month—four hours—on communication inefficiency. That's 48 hours per year. You're hemorrhaging two full work weeks annually while claiming you don't have time to practice being clearer. THE MATURITY SHIFT Immature leaders think: "My cabinet needs to communicate better." Mature leaders think: "We need to practice communicating better together." Immature leaders assume communication skills are innate—either you have them or you don't—and spend board retreats wondering why their brilliant team can't seem to align. Mature leaders build systems where communication skills are practiced regularly until they become second nature. Immature leaders address communication problems after they explode. Mature leaders practice communication before crisis hits. The difference is the difference between hoping your team can have difficult conversations and knowing they can because they've practiced. One makes impossible feel permanent. One makes impossible feel temporary. Cabinet silence isn't a personality problem. It's a practice problem. And unlike enrollment declines or budget cuts, this one is completely within your control. Your turn: Think about your last cabinet meeting. How many conversations do you think were happening simultaneously that weren't actually being spoken out loud? What would change if you named those conversations explicitly? Drop a comment. Tag a cabinet member who needs to see this. Or screenshot this and text it to your Chief of Staff with the message "Let's talk about our next meeting." P.S. If you're thinking "I don't have bandwidth to create communication practice resources for my team"—I already did it for you.  The GROUP is a free community where every newsletter becomes a ready-to-deploy Leader CORE Lesson and Guide. Practice scenarios. Discussion prompts. Diagnostic questions. Everything you need to lead your team through structured communication development without the Sunday night scramble.
By HPG Info October 8, 2025
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