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

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Why Your Cabinet Is Exhausted and Your Results Are Flat LEADER INSIGHTS: Weekly Team Intelligence for Educational Leaders | Dr. Joe Hill | Higher Performance Group A superintendent I know — twenty-one years in education, relentlessly strategic, the kind of leader other leaders call when they're stuck — sat down at a regional convening last fall and said something I haven't stopped thinking about. "I feel like we're sprinting. Everybody's exhausted. Nobody can point to what changed." He wasn't describing failure. His district is moving. His board is happy. His cabinet shows up. He was describing something harder to name: the specific exhaustion of motion without transformation. 73% of educational leaders in our 987-team study report feeling perpetually behind — behind on initiatives, behind on trends, behind on where they think they should be by now. You're not behind. You've been playing the wrong game entirely. The institutions actually winning? They stopped playing catch-up years ago. They're running a fundamentally different game — with fundamentally different rules. And here's the plot twist: the game they're playing is actually simpler than the one you're exhausting yourself with right now. TQ = IQ × EQ × PQ. When your team's collective attention is fragmented across twenty-three initiatives, the PQ dimension — positional intelligence, the clarity about who does what and why — collapses toward zero. Anything multiplied by zero produces exactly the strategic outcomes you've been getting. The Diagnosis: Three Games, One Winner Let's talk about this like adults who've survived multiple strategic planning retreats and at least one initiative that died quietly in a Google Drive folder nobody checks anymore. There's a psychological phenomenon researchers call "temporal comparison bias" that explains why brilliant educational leaders — people who've built entire programs, navigated accreditation, turned around failing departments — feel perpetually three steps behind. Here's how it plays out in real time: Monday, 6:45 AM. You're scrolling LinkedIn before your first meeting. A superintendent three states over just announced a groundbreaking AI initiative. Your immediate thought: We should be doing that. Why aren't we doing that? Tuesday, 2:30 PM. Conference call with peer institutions. Someone mentions their new enrollment strategy showing "promising results." You add "explore enrollment strategy overhaul" to the list of seventeen other things you're currently "exploring." Wednesday, 10:00 AM. Cabinet meeting. Your VP of Academic Affairs wants to discuss three new program launches. Your CFO has concerns about falling behind on facilities. Your Provost is worried about losing ground in faculty development. By Friday, your strategic priorities list has grown from eight items to fourteen. None have moved forward. All are justified by fear of falling further behind. The institutions you think are "ahead" aren't managing more initiatives better. They're managing fewer with singular focus. That superintendent with the AI initiative? She killed four other initiatives to create space for it. You're not behind them. You're just carrying different weight. They're running a 5K. You're running a marathon with a 50-pound backpack and wondering why you can't keep pace. The real problem? You've been optimizing for coverage when you should be optimizing for impact. Coverage thinking: We need to be doing something in every area — enrollment, retention, innovation, facilities, faculty development, student experience, community engagement, technology, equity. Impact thinking: What's the one thing that, if we did it exceptionally well, would make everything else easier or unnecessary? Coverage creates the illusion of progress. Impact creates actual transformation. (This is exactly why The Team Institute exists — not to add more to your plate, but to help your entire leadership cabinet build the collective capacity to decide what belongs on the plate in the first place.) The Framework: The Three Games Call this the Strategic Games Framework. Or don't. It'll still explain why your last strategic plan produced a beautiful document that nobody references six months later. Every educational institution is playing one of three games. Most don't realize they have a choice. The ones winning? They chose deliberately. Game 1: The Comparison Game (Where 70% of leaders live) Success means keeping pace with everyone else. Winning looks like never falling too far behind the pack. Losing looks exactly the same as winning — just with more anxiety. Average strategic priorities per institution playing this game: 12 to 18. Average implementation completion rate: 34%. Leadership energy spent managing initiatives vs. actually transforming: 85% management, 15% transformation. This game is unwinnable. The moment you catch up, the benchmark moves. It's an infinite treadmill where "ahead" doesn't exist — only "less behind." The insidious part? It feels productive. Lots of meetings. Lots of planning. Lots of slide decks. Zero transformation. Game 2: The Innovation Game (Where 20% of disruptors live) Success means being first. Winning looks like conference keynotes and site visits from peer institutions. Losing looks like spectacular failures that become cautionary tales. The Innovation Game is seductive because it feels like leadership — you're not following, you're pioneering. But here's the trap: innovation without implementation infrastructure creates what I call pilot program purgatory — brilliant ideas that launch with fanfare, then quietly fade when the hard work of institutionalization begins. 8 to 12 new initiatives launched per year. 2 to 3 that survive past Year 2. 60% of cabinet capacity consumed managing "innovation." You're pioneering new approaches faster than your institution can absorb change. It's like trying to teach someone to swim by throwing them in the ocean during a storm. Technically teaching swimming. Practically creating trauma. Game 3: The Multiplication Game (Where the 10% who actually win live) Success means multiplying what already works. Winning produces consistent, compound growth that looks boring from the outside but transforms everything from the inside. Your strategy: Subtraction before addition. Multiplication before innovation. Depth before breadth. The institutions winning this game look unimpressive in conference presentations. No flashy AI initiatives (yet). No radical restructuring (yet). Instead: they took the three things they were already decent at and became exceptional at them. Then they built the capacity to add a fourth. That sequencing is everything. It's the TQ formula applied to institutional strategy — not scattered individual initiatives, but collective focus that compounds. IQ × EQ × PQ, multiplied at the team level, aimed at three things instead of twenty-three. The Case Study: Michael's $0 Transformation Let me tell you about a president I'll call Michael. (Not his real name — but Michael, your former Provost absolutely knows this story is about your first two years together, and she's probably nodding vigorously right now.) Michael led a regional public university: 11,000 students, seven colleges, a cabinet of 10 VPs averaging 21 years of experience each. Combined credentials that could staff a small think tank. Combined ability to finish what they started? Roughly equivalent to a book club that's been "reading" the same book for three years. What Michael inherited: 6 major strategic priorities. 23 sub-initiatives. 14 presidential task forces. 8 pilot programs in "evaluation." 147 action items. Zero clear accountability for whether any of it was working. His first six months were consumed by progress reports: "We had three focus groups." "We're gathering stakeholder input." "We're exploring best practices." Activity everywhere. Impact nowhere. Then Michael did something radical. He stopped playing the Comparison Game. He asked his cabinet one question: If we could only do three things exceptionally well over the next two years — three things that would demonstrably transform student outcomes — what would they be? The room went silent. His VP of Student Affairs said what everyone was thinking: "Are you saying we stop doing everything else?" "I'm saying we stop pretending we're doing everything else. Right now, we're doing 23 things at 40% quality. I'm proposing we do 3 things at 95% quality." Months 1–3: Eliminated 20 of 23 initiatives. Dissolved 11 of 14 task forces. Concentrated resources on three priorities: first-year experience transformation, career-connected learning, and faculty excellence in teaching. Months 4–12: Meetings dropped from 3.5 hours to 90 minutes. Decision velocity increased 4x. Implementation completion rate went from 34% to 89%. Year 2 results: First-year retention: +8.7% — largest single-year increase in school history Career placement within 6 months of graduation: +12.3% Faculty teaching excellence scores: +15% across all colleges Cabinet meeting time: cut in half Leadership team: "Finally feels like we're making progress instead of managing chaos" Same people. Same budget. Same external constraints. Same competitive environment. Different game. If you recognize the gap between your cabinet's talent and what you're actually producing together — and you suspect another individual development program won't close it — this is exactly what The TEAM INSTITUTE was built for. Not a workshop. Not a retreat. An 8-month sequential operating system your entire cabinet builds together, from trust to focused execution, applied to your actual strategic challenges. We don't fix people. We multiply systems. More on that below. The Application: Switching Games Here's what to do this week — assuming your calendar isn't already booked with meetings about meetings, in which case, that's actually your first problem: Step 1: The Brutal Subtraction Audit (90 minutes, next cabinet meeting) Put every current "strategic priority" on the board. Not just the official ones — the real ones. Every initiative people are actually working on. Every pilot being "evaluated." Every task force meeting monthly. Ask three questions about each: Does this produce measurable transformation in student outcomes — not stakeholder engagement, not data gathered, actual outcomes? Are we providing 70% or more of what this initiative actually needs to succeed, or are we setting people up to fail while calling it strategic? And does this build future capacity, or will it always require its own dedicated resources? Then force rank everything. Not 'these are all important.' Actual forced ranking. Stop at three. Everything below three? Stop doing it. Not 'deprioritize.' Not 'put on hold.' Stop. (Someone will invoke sunk cost: 'But we've already invested so much in X!' The investment is already gone. The question is whether you keep throwing resources at it. That's not strategy. That's loyalty to a decision that isn't working.) Step 2: The Capacity Calculation (30 minutes, solo) For each of your top three priorities, calculate the actual hours per week required — from the leadership team and from implementation teams — multiplied by 42 working weeks. Add all three together. Do you actually have that capacity, or are you assuming people will "make it work" by eliminating evenings and weekends? If the honest answer is no, you're still in the Addition Game. Reduce scope, eliminate something else, or accept that you're asking people to work unsustainably. Pick one. Step 3: The Multiplication Protocol (Ongoing) For the next 90 days, before adding any new initiative, task force, pilot, or "exploration," your cabinet must answer one question: What are we stopping to create space for this? Not "we'll find time." An actual answer. If you can't name what you're stopping, you can't start the new thing. Track two numbers: addition-to-subtraction ratio (1:1 or better means you're in the Multiplication Game) and implementation completion rate (below 50% means scattered attention producing scattered results; 80%+ means you've actually switched games). On the Objections: "But our board expects us to address all of these areas." Your board expects outcomes, not activity reports. What would happen if you walked in with this: "We focused all our capacity on three priorities. First-year retention is up 8.7%. Career placement is up 12.3%. Faculty excellence scores are up 15%." Boards don't micromanage success. They micromanage stagnation. Produce compound results and they stop asking why you're not doing more. The Maturity Shift On priorities: "We need to be doing more to stay competitive." → "We need to be doing less, exceptionally well, to actually transform." On activity: Confuses meetings completed with momentum. → Measures transformation produced, not initiatives launched. On the competition: Watches what peers are doing and adds to the list. → Watches what's working internally and multiplies it. On capacity: Assumes "we'll find time." Burns people out. Repeats. → Calculates actual capacity. Subtracts before adding. Compounds. You're not behind. You've been playing the wrong game. The Multiplication Game is harder to start — subtracting things you've invested in, having honest conversations about actual capacity, saying no to things that matter — but it's infinitely more sustainable. And the institutions winning it? They look boring from the outside and transformational from the inside. Your Turn: Which game is your cabinet actually playing? Drop one word in the comments: COMPARISON, INNOVATION, or MULTIPLICATION. Then tag a cabinet member who you think would answer differently than you would. That gap in perception? That's the data. Or screenshot the three game descriptions and text them to your leadership team with one question: "Which game are we actually playing right now?" Ready to Stop Playing Catch-Up? Here's what I know after studying 987 leadership teams across 43 states: the cabinet that can't agree on three priorities isn't struggling with strategy. It's struggling with trust. Without trust, subtraction conversations become political. Capacity calculations become weaponized. Forced ranking becomes a turf war. That's why the Multiplication Game isn't something you implement from a newsletter. You need your entire cabinet in the room, building the same foundation, in sequence — not a two-day retreat you'll never quite finish, but a sustained developmental arc that actually rewires how your team thinks together. That's what The TEAM INSTITUTE was built to do. The TEAM INSTITUTE is an 8-month journey that takes your cabinet from individually brilliant to collectively unstoppable — sequentially, through trust, empowerment, collaboration, and focused execution, each month building on the last. You can't skip trust and go straight to strategy. That's not leadership development. That's wishful thinking with a facilitator. The results from teams that complete the full sequence: 3x performance improvement. 29% higher engagement. 27% better organizational outcomes. Zero burnout increase. Not because we fixed anyone — because we changed the system they were operating in. The requirement is simple and non-negotiable: full cabinet participation. Partial engagement produces partial results. You cannot build team-level multiplication with individual-level development. That's the model that got you here. If you're a leader who sees the gap between your cabinet's talent and your collective results — and you're ready to stop treating that gap as a motivation problem — let's talk. Schedule a 30-minute consultation to explore whether The Team Institute is the right fit for your leadership context. This isn't a sales pitch. It's a conversation between people who refuse to accept that "busy" and "effective" mean the same thing. [LEARN MORE] higherperformancegroup.com [SCHEDULE CONSULTATION] Found value in this? Help other educational leaders find it: → Repost with your honest answer — which game is your cabinet actually playing? → Tag a leader who's exhausted from the Addition Game and ready to switch → Comment with the one initiative you know you should stop but haven't — naming it is the first step The more leaders who shift from addition to multiplication, the better our educational systems become. Follow DR. JOE HILL and Higher Performance Group for weekly Team Intelligence insights. Next issue: "Your Cabinet Mistakes Consensus for Alignment (And It's Killing Every Decision)" We'll explore why your leadership team spends three meetings nodding in agreement, then fragments in seventeen different directions the moment they leave the room. Spoiler: You don't have an alignment problem. You have a 'we've never actually defined what alignment means' problem. And the text messages your VPs send each other after cabinet meetings? Those are where your real strategic plan lives. Dr. Joe Hill | Higher Performance Group | The Team Institute higherperformancegroup.com
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