5 Questions Every Disheartened Leader Should Ask Themselves Before Giving Up Or Giving In

March 1, 2022

Dear Disheartened Leader,


Being THE leader isn’t the easiest thing in the world. But it's not the hardest thing either.


You’re not alone. The “ER” in the middle of the word lead•ER•ship is there on purpose. It is not supposed to be easy.


If you’re really leading, there’s rarely a season that isn’t filled with “ER.”


You solve a problem, two more pop up. You resolve them, and out of the corner of your eye, spot the next one.

As a campus leader for over 30 years, I get it.


After seeing leader after leader struggle with discouragement and wanting to throw in the towel long before their calling ran out, I wanted to write this note.


None of us really feel like the most successful person on earth. I surely don’t and you don’t need to fake it either.


And even though things are going well for HPG, and we have so much to be thankful for, I spend too many days wondering whether I’m missing something or feeling like we should be making more progress than we should.


You know what it’s like… The weight of:


  • Budget and expenses.
  • People who promise the moon but can’t even deliver the earth.
  • New people who say they’re in and then walk away.
  • Feeling like you are always under a microscope.
  • Not being where you thought you would be at this point in your life.
  • Uncertainty. Constant uncertainty.
  • Chronic struggles with talented team members who just don’t want to wear the team jersey.
  • Knowing your system isn’t perfect and wishing it would be but knowing it won’t ever be.
  • Lack of gratitude from those whom you are bending over backward to serve.
  • Feeling let down by others.
  • Feeling like you are letting yourself down.
  • Seeing other people’s practice and believing they have it easier than you do.


And on and on and on it goes…


This is the stuff of leadership they never teach you in graduate school.

I want you to know something. The discouragement you feel inside is real and coming from somewhere. Think about this and let this sink in for a minute today: The happiest and healthiest people are those whose expectations meet reality.


What do you do with that?


Here are five questions every disheartened leader should ask themselves before giving up or giving in.


1. What do I expect my system to give me?

No team or system will ever give you ultimate peace, fulfillment, joy, purpose, or anything like that. If you are expecting that from being a leader, you won’t find it.


If you are constantly discouraged or frustrated about your system, it might be because you are hoping it will give you something only your conscience can give you. That is called PEACE.


When you look to people or things to give you what only your faith can give you, you’re signed up for a dash of misery.


2. Who do I hope will affirm me?

This is a big one.


We all look for affirmation from people.


Here’s something someone told me a long time ago that I really don’t like because it’s so true: Never expect the people you lead to affirm you. 


It’s not fair to them. And ultimately, it’s not fair to you.


Your job is to lead them, not to get them to applaud you.


Hey, if it happens…awesome. Consider that a bonus. But if you keep looking to others for praise, you’ll end up sliding down the slippery slope under question 3…


3. Who am I trying to please?

You will never fully please the people you serve. It’s impossible because we are imperfect people (and so are they).


If you are trying to please other leaders or get recognized, you will be miserable. You can never keep up with anyone else’s expectations. And you’ll let yourself, your family, and ultimately your team down.


If you focused on being liked, you won’t lead. Your insistence on pleasing everyone will mean you ultimately please no one.

Not to mention yourself.


4. How honest am I being with myself and others?

If you stuff your leadership failures and missed expectations instead of dealing with them, you will implode or explode one day. Your discouragement and mine often come from stuffing things we should just admit and deal with.


If you have a problem with another person, be completely honest with them. If you are mad at somebody, tell them.

If somebody let you down, let them now. If you have let yourself down, tell a friend.


Lying and pretending lead to misery. Just say it. I have done this numerous times and it’s terrible up front but so freeing in the end.


And you know what? Much of the time you end up redeeming the relationship.


If you won’t be honest with others, you also won’t be able to truly lead them.


5. What lie am I believing?

Gurus make it seem so easy, don’t they? Go to their conference or buy their product and all your problems disappear. Did you ever buy into that lie at some point?


Chances are you thought leadership would be easier. Well, that’s just silly.


Identify the lie you are believing, and you will crush some of the discouragement. The lie that storytellers sell you is really killing your spirit. We only need to look at history to discover that leadership was rarely ever easy.


Your discouragement isn’t just discouragement. It’s a symptom of something deeper going on. If you want to create a healthy culture across your system, you can’t be angry all the time. You can’t be frustrated 24/7. Take a step today & answer these questions honestly.


I believe it will help you beat your discouragement and get back on the growth track.


It’s propaganda to say leadership is easy. What’s true is that humble, determined, committed leadership is worth it.


Everyone deserves to live in a community served by healthy teams and highly reliable systems.


P.S. Whenever you are ready here are the 2 best ways I can help you:


1) Get your FREE guide: 5 Evidence-Based Practices to Reclaim More Team Engagement with Less Effort: www.higherperformancegroup.com/reclaim


2) Schedule a Call. Let’s talk about the obstacles (and opportunities) that you & your team are currently facing.  www.higherperformancegroup.com/schedule

More Blog Articles

By HPG Info October 8, 2025
Your Institution Has 18 Months, and Here's What 23 Leaders Did on October 1st to Model the Way Forward "We've got about 18 months to figure this thing out." That's the window educational leaders have to transform proactively—or be forced to transform reactively in survival mode. On October 1st, 2025, twenty-three district superintendents and college presidents stopped planning alone and started building together. Not the leaders waiting for perfect strategic plans. Not the ones defending comfortable systems. The BUILDERS—leaders whose institutions have grown enrollment 15-40% despite demographic headwinds, who've launched partnerships generating $50M+ in regional economic impact, who've redesigned curricula around employer needs that traditional institutions haven't touched. What emerged in those 60 minutes wasn't comfortable. It was clarifying. Here's what 1.7 million lost higher education students and 1.2 million departed K-12 students since 2019 actually tell us: Students didn't drop out. They opted out. Traditional education lost not because our teaching failed, but because our thinking stayed small while the world moved fast. The market already voted. And it didn't vote for more performance optics. The Four Types of Leaders DR. JOE HILL opened with a framework that landed hard:  Four types of leaders populate education today. Coasters worship stability and avoid controversy. Climbers optimize metrics but often overlook whether those metrics matter to students. Dreamers create gorgeous strategic plans that rarely launch. And Builders —rare, hungry, idealistic—who possess what Hill calls "moral ambition."
By HPG Info September 30, 2025
The New POWER Model To Break Through Your Institutional Stranglehold What if I told you that right now, as you read this, a 16-year-old with a $47 smartphone is getting a better physics education than students at $80,000-per-year private schools? And what if the real threat to education isn't the technology that makes this possible—but the army of insiders desperately protecting their preferences? Picture this scene, happening in your institution right now: While a teenager in rural Kenya outscores Ivy League applicants using AI that costs $47, your innovation committee is on month six of debating whether ChatGPT should be "allowed" in classrooms. Who's really in that room? The union rep protecting job security. The department chair defending territorial boundaries. The IT director gatekeeping technology budgets. The compliance officer citing policies written in 1987. The parent board members clutching their own college experiences like religious texts. Notice who's missing? Students. The ones we claim to serve. The uncomfortable truth: Every disrupted institution dies the same way—not from external threats, but from internal antibodies attacking their own cure. The Resistance Playbook -The Seven Horsemen of Educational Stagnation 1. The Union Wall: "This wasn't collectively bargained" 2. The Compliance Shield: "State standards don't allow it" 3. The Equity Trap: "Not every student has access" (while ignoring that current inequality) 4. The Safety Theater: "What about screen time/data privacy/cheating?" 5. The Budget Fortress: "We don't have funds" (for $60/year AI that replaces $50/hour tutoring) 6. The Committee Quicksand: "Let's form a task force to study this" 7. The Tradition Anchor: "We've always done it this way—and look at our alumni" Each of these sounds responsible. Each is actually sabotage. Your Counter-Intelligence Manual: The POWER Framework P - Preempt with Pilot Programs The Resistance: "We need district-wide consensus first" Your Move: Start with 5% of students as an "experimental pilot." Call it "action research." Make it opt-in. Document everything. Power Principle: Small wins bypass big resistance. By the time committees notice, you'll have data they can't ignore. Real Example: A principal in Texas started an AI tutoring "study" with 30 struggling math students. No announcements. No permissions beyond standard research protocols. Results after 60 days: 73% improvement in test scores. The school board that would have said "no" suddenly wanted it district-wide. O - Orchestrate Unlikely Alliances The Resistance: Traditional power brokers uniting against change Your Move: Build a coalition of the overlooked: · Parents of struggling students (they're desperate for anything that works) · Young teachers (they're already using AI secretly) · Local employers (they know graduates aren't prepared) · Students themselves (give them a voice before they vote with their feet) Power Principle: When students and employers align, bureaucrats lose their cover. Tactical Nugget: Create a "Future Ready Task Force" with 60% external stakeholders. Internal resisters can't dominate a room they don't control. W - Weaponize Their Own Data The Resistance: "Our current approach is working fine" Your Move: Deploy the Mirror Strategy: · Pull your institution's own strategic plan (look for "innovation" and "21st-century skills") · Document the gap between rhetoric and reality · Present AI as fulfilling THEIR stated goals Power Principle: People can't argue against their own published commitments. Script for Your Next Meeting: "I'm confused. Our strategic plan says we're committed to personalized learning. Here's a solution that delivers exactly that for $60 per student. Help me understand why we wouldn't want to achieve our own goals?" E - Establish Facts on the Ground The Resistance: "We need to wait for policy guidance" Your Move: While they're waiting for permission, you're creating reality: · Get teachers to "supplement" with AI tools (not "replace" anything) · Frame as "supporting" traditional teaching (not "transforming" it) · Use their language: "differentiated instruction," "scaffolding," "engagement" Power Principle: Policy follows practice, never the reverse. The Jujitsu Move: When resistance emerges, ask: "Are you suggesting we stop helping struggling students while we wait for bureaucratic approval?" R - Reframe the Risk Conversation The Resistance: "What if something goes wrong?" Your Move: Flip the risk narrative: · "What's the risk of NOT adapting while our students fall further behind?" · "Which lawsuit scares you more: Using AI, or failing students for an AI world?" · "Show me the damage from innovation. I'll show you the carnage from stagnation." Power Principle: Make inaction scarier than action. The Data Bomb: Share enrollment projections. Show competitor schools adopting AI. Calculate lost tuition/funding. Make status quo feel like standing on burning ground. Three Ways Leaders Are Breaking the Power Structure The Parallel Program Strategy One superintendent facing union resistance: Created an "optional enhanced learning program" running parallel to traditional classes. Parents could opt in. Teachers could volunteer for extra pay. Within one semester, 70% opted in. The union couldn't fight what members were choosing. The Budget Jujitsu Approach A principal denied AI funding: Calculated the cost of current failure—summer school, remedial classes, dropout recovery. Showed AI would save 3x its cost. Framed it as "fiscal responsibility." The same board that said "we can't afford it" suddenly couldn't afford NOT to do it. The Grassroots Inevitability Method A department chair at a major university: Knew faculty senate would block any top-down change. Instead, got three professors to run "independent experiments" with AI. Published results internally. Other professors demanded access. By the time administration noticed, faculty were driving the change themselves. The Nuclear Option: The Student Uprising Strategy When all else fails, remember: Students have ultimate power—they can leave. The Activation Sequence: 1. Survey students about their AI use (spoiler: it's already 90%+) 2. Share what competitor schools are offering 3. Ask: "Should we prepare you for the future or the past?" 4. Let them present to the board (boards fear students more than faculty) The Penn State Precedent: Students created their own AI learning collaborative when administration dragged feet. 300 members in week one. The university suddenly found urgency. Your 30-Day Power Shift Playbook Week 1: Map the Resistance · Identify your three biggest blockers · Document their stated concerns · Find contradictions in their positions Week 2: Build Your Shadow Cabinet · Recruit three innovative teachers · Connect with five frustrated parents · Engage ten ambitious students Week 3: Launch Your Trojan Horse · Start your "pilot program" · Frame it as "research" · Make participation voluntary Week 4: Create Irreversible Momentum · Share early wins broadly · Get testimonials from students/parents · Present to board as "update" not "request" The Conversation That Changes Everything Script for Your Next Leadership Meeting: "I need clarity on our priorities. Are we primarily serving: · Student success or adult comfort? · Future readiness or present convenience? · Learning outcomes or institutional traditions? Because AI is forcing us to choose. And our students are watching." The Answer to Our Opening Question Remember that 16-year-old in Kenya with her $47 education? She's not winning because she has better technology. She's winning because she has no bureaucracy to protect, no union contracts to honor, no traditions to defend, no committees to consult. She has only one concern: Learning. The power struggle in education isn't about AI. It's about who we really serve—the students demanding transformation or the system demanding preservation. The leaders who survive won't be the ones who managed the resistance. They'll be the ones who made resistance irrelevant by creating unstoppable momentum. Your Courage Checkpoint Three questions that determine your next decade: 1. When did you last make a decision that scared your biggest donors/board members but thrilled your students? 2. If your own child could choose between your institution and an AI-powered alternative, what would they choose? (Be honest.) 3. Are you willing to be the villain in the old story to be the hero in the new one? The Leadership Moment That Will Define You You have 18 months before the choice gets made for you. The committee won't save you. The board won't lead this. The union won't embrace it. The parents won't understand it at first. But the students? They're already there, waiting for you to catch up. Your move, boss. READY TO RECLAIM YOUR VOICE IN THIS REVOLUTION? Stop letting committee-approved messages dilute your vision for transformation. Start speaking human again—because that's what makes revolutionaries out of educators. Just as the Overton Window has shattered in education, the window of acceptable leadership communication has expanded. Yet, most educational leaders are still trapped in conference room-speak, while their institutions face an existential transformation. The first step is discovering how your authentic voice got lost. In just 5 minutes, you can uncover: · Where institutional polish killed your ability to inspire real change · Which of your natural communication styles your teachers and students actually crave · How to transform policy memos into messages that create movements  → Take the 5-Minute Authentic Leadership Communication Assessment
Show More