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 September 15, 2026
Not the parking-lot kind. The kind that happens in the room. I want to say something that will get me uninvited from a few conferences this year: the calmest cabinet meeting in your building this month was probably the most dishonest one. Nobody lied in that meeting. Everyone in the room agreed to something nobody actually believed, and called it professionalism. There's a scene near the start of 12 Angry Men where eleven jurors vote guilty in under two minutes. Nobody's examined the knife. Nobody's questioned the witness. They just want to make the four o'clock ballgame, and a fast unanimous vote looks exactly like agreement. Patrick Lencioni named the real version of that back in 2002, and the label still fits: artificial harmony. Your cabinet runs its own eleven-to-one vote most weeks, and it doesn't need a jury box to do it. Here's the uncomfortable part. A cabinet with zero visible conflict almost always has the same explanation: something real never got said out loud. THE DIAGNOSIS Let's talk about this like adults who've sat through a “great meeting” that solved nothing. You know the meeting where the budget gets flagged as a concern, everyone nods that they'll “look into their numbers,” and six weeks later the same number resurfaces, because nobody said out loud whose number it was to fix. You know the one where two VPs have been quietly furious with each other since March over a staffing decision, and you can feel it every week in how carefully they avoid each other, and you've decided not to name it because naming it feels like starting something. You know the one where a board member's pet initiative gets full-throated public support in the room, then gets picked apart, sentence by sentence, in the parking lot the second the meeting adjourns. That parking lot conversation is where your cabinet's real meeting is actually happening. The one with the agenda is theater. We call it Consent Theater: everyone performs alignment in the room, and almost nobody in the room actually feels it. I know the exhaustion of being the only person who can feel the thing nobody's saying. It's a specific kind of lonely: watching six capable adults nod in unison at a decision you already know three of them will quietly work around by Thursday. (This is the exact gap THE TEAM INSTITUTE was built to close: the collective architecture that makes disagreement safe enough to happen in the room, in real time, instead of surfacing later in a one-on-one, a group text, or the parking lot. Most leadership development still trains individuals to argue better. This trains the room to hold the argument without breaking. More on that in a moment.) Here's the diagnosis. This is an EQ problem, specifically the part of EQ nobody trains: the capacity to host real disagreement without the room falling apart. Most leadership development sharpens IQ. Almost none of it builds a team's tolerance for productive friction. TQ = IQ × EQ × PQ. Skip that capacity, and you're not getting a calmer team. You're multiplying by something close to zero. THE REAL-FIGHT LITMUS (Or: How to Tell a Real Fight From a Tantrum, in Under Ten Seconds) Call this the Real-Fight Litmus. Or don't — it'll still explain why your cabinet's least professional-sounding argument last year was probably its most valuable ten minutes, while last month's perfectly polite meeting produced exactly nothing. Not all workplace drama is the same. There's melodrama, and there's the real thing, and most leaders never learned to tell them apart, so they shut down both the same way. Three checks separate them. The Stakes Check. Is this about the mission, the budget, the students, the decision, or is it about who gets credit and whose feelings got bruised three weeks ago? Real conflict is anchored to something the institution actually needs solved. (IQ's job: knowing whether the fight is even worth having.) The Address Check. Is it being said to the person it's about, in the room, right now, or about that person, to someone else, later? Real conflict happens at the table. Manufactured drama happens in the parking lot, the group text, the hallway pull-aside that somehow never includes the actual person. (EQ's job: whether the team has the nerve to say it to the face instead of the back.) The Landing Check. Does it end with a decision, an owner, and a next step, or does it just end, unresolved, waiting to resurface next month wearing a different disguise? (PQ's job: reading the room accurately enough to know when the real issue has actually surfaced.) Miss any one, and per the formula, you're multiplying by something close to zero: all the emotional energy of a real fight, none of the resolution. THE CASE STUDY This is a composite, drawn from patterns across our work with 987 leadership teams , not one specific superintendent's story. Picture a seven-person cabinet known among peer districts as “the calm one.” Internally, two departments hadn't fully trusted each other in over a year, since a staffing reallocation neither side felt was handled fairly. Nobody had said that sentence out loud with both of them in the room. Instead, it surfaced everywhere else: in one-on-ones with the superintendent, in the politely cold exchanges in shared meetings, in a joint enrollment-outreach grant the two departments had quietly stopped planning together — fourteen months and counting. The turning point came in one meeting when the superintendent named it directly: “I think there's an unresolved staffing decision between these two departments, and I'd rather we have that conversation here, today, than everywhere else.” Twenty-five uncomfortable minutes followed, then something the cabinet hadn't had in over a year: a resolution, with an owner and a next step, that both departments could name identically when asked separately. The grant application was back on both departments' calendars within three weeks. Six months later, joint planning had gone from an occasional truce to a standing agenda item. Same seven people. One real fight, finally allowed to land where it belonged. THE APPLICATION Here's what to do Monday morning (assuming you're not already mid-crisis, in which case, do this Tuesday): Step 1: Run the Litmus on Your Last Meeting (15 minutes). Pull last week's cabinet agenda. For each item that generated any friction at all, ask the three checks: was it about the mission, or about ego? Was it said in the room, or about someone elsewhere? Did it land on a decision, or did it just stop? If most items pass all three, you have real conflict already, and you're ahead of most cabinets. If most items fail the Address Check, you have a parking-lot cabinet, and the real meeting is happening somewhere you're not. Step 2: Name One Unresolved Thing, Out Loud, In the Room (20 minutes at your next meeting). Pick the one disagreement everyone already knows about but nobody has said directly to the people involved. Say it plainly, the way the superintendent did above: name what you've noticed, and invite the actual conversation, in the room, this week, not “offline.” This will feel like the least professional five minutes you've had in months. It's also the most useful. Step 3: Build a Team Norm for the Address Check (ongoing). Agree, as a cabinet, on one rule: disagreements about a colleague's decision get raised to that colleague, not about them. Practicing this once doesn't undo a year of parking-lot conversations. Practicing it every week, for a few months, does. “We don't have time for this.” You're already spending it. The latest workplace research puts the average manager at over four hours a week managing workplace conflict — more than 230 hours a year. That number doesn't change based on whether you have the real fight or not. It just changes whether that time produces an actual decision, or more meetings about the meeting. “This will make our meetings feel less professional.” Maybe for the first few. But Google's own multi-year Project Aristotle study found one trait separated its highest-performing teams from the rest: psychological safety, the freedom to disagree openly without fear of looking bad in the room. Politeness never made the list. You've been chasing the wrong variable. THE MATURITY SHIFT Immature leaders think: “A good meeting is one where nobody gets upset.” Mature leaders think: “A good meeting is one where the real thing finally got said.” Immature leaders protect the room from conflict, and call it culture. Mature leaders protect the room's capacity to have the conflict, and call it trust. The gap runs deeper than temperament. Somewhere along the way, we convinced an entire generation of leaders that a quiet room is a healthy room. Lencioni named the pattern in 2002. Twenty-four years and a mountain of team-performance research later, most cabinets still run on the original assumption: calm equals healthy. Every eleven-to-one vote your cabinet takes without a single dissenting question is a choice, made weekly, about whether the real disagreement happens in the room or goes and finds somewhere else to live. Your turn: think of the disagreement your cabinet is currently avoiding in the name of staying “professional.” Where is it actually living right now? A one-on-one? A group text? Somebody's resignation letter draft? Name it in the comments. I'll wait. If artificial harmony has been running your cabinet's meetings, and after this issue you don't believe “calm” and “healthy” are the same thing anymore, then what's missing is architecture: the collective skill of hosting real disagreement without the room, or the relationships in it, falling apart. This is what THE TEAM INSTITUTE builds. It's an eight-month program for full leadership cabinets — superintendents and university presidents and the people who sit across the table from them — built around exactly this kind of collective muscle: knowing which fights are real, having them where they belong, and landing them on an actual decision. Across 987 leadership teams, cabinets that did this work saw performance improve roughly 3x and engagement rise 29%, without an increase in burnout, which is usually the quiet cost of every other leadership initiative that just asks people to try harder. Start with the Team Intelligence Assessment. It'll tell you, plainly, whether your cabinet's calm is real or borrowed: https://www.higherperformancegroup.com/tq-assessment Whether or not this is the season for that step, here's a smaller one that costs nothing: repost this with the disagreement your cabinet has been calling “fine” for longer than it should have, tag the colleague who already knows exactly which one you mean, or drop your own version in the comments. Somebody else's cabinet needs to hear that they're not the only one avoiding the same conversation. Follow DR. JOE HILL and Higher Performance Group | THE TEAM INSTITUTE
By HPG Info September 7, 2026
Fluent. Confident. Wrong. In that order. Every cabinet meeting I've sat in since the second week of June has opened with some version of the same sentence: "The board wants to know our AI plan." Nobody's arguing AI matters. That fight's over. What almost nobody's asking is the question underneath it: the one that actually decides whether this fall helps your cabinet or quietly wrecks it. Before you put a machine on the payroll as your cabinet's newest ghostwriter, have you checked what it already believes about you? Here's what nobody tells a team of senior leaders walking into its first AI rollout: the tool doesn't create your team's judgment. It ghostwrites it, fluently, into every board memo and parent email and strategic plan you hand it, sounding exactly as confident in the ones that are wrong as the ones that are right. Two stories explain what's actually at stake this fall. One's old. One's brand new. Together, they're the whole problem. THE SENTENCE In third grade, a teacher tried to stop a boy from getting bullied. He'd been held back in reading, had migraines nobody diagnosed, and needed things repeated more than his classmates did. So she stepped in, pointed at him in front of the whole room, and said the thing she thought would protect him: "Leave that kid alone. That's the boy with the broken brain." She meant it kindly. He heard two words. Broken brain became the sentence he ran, silently, for the next decade: every time he wasn't picked for a team, every time he failed a test, every time he took the back-row seat hoping nobody would call on him. That kid grew up to be Jim Kwik, now one of the most recognized names in learning and memory training on the planet, the guy Fortune 500 companies and elite athletes call when they need to think faster under pressure. He told the story in a conversation earlier this year, and the line that stopped me wasn't the injury. It was what he said actually held him back: "Under stress, we don't rise to the level of our aspirations. We fall to the level of our stories, our systems, and our self-image." Not his intelligence. Not his skill. His self-image, inherited from a five-second sentence somebody else said, replaying under pressure for ten straight years. Now sit with the version your own cabinet is running. Maybe it's a board comment from three budget cycles ago that nobody's repeated out loud since, but everybody still quietly believes. Maybe it's a single paragraph an accreditation team wrote four years back that's still deciding what your provost thinks she's allowed to propose. Maybe it's simpler: a founding leader who once told this team they weren't ready for something, and nobody has tested whether that's still true. Here's the part that should actually worry you. Kwik didn't get better at learning by treating the injury. He got better by finding, and rewriting, the sentence. Your cabinet's talent isn't the variable in question here. It rarely is. The sentence running underneath the talent is. THE TURN Here's why this matters more this fall than any fall before it. For every year of your career until now, your cabinet's inherited sentence stayed mostly contained. It shaped a meeting here, a hesitation there, a proposal that quietly never got made. Slow damage, spread out over years. That containment is gone. Kwik, talking about the exact tools your board is asking about, put it plainly: "AI can scale and amplify. But it can only scale and amplify what a human brings to it." Feed it a clear, tested, collectively-owned judgment, and it multiplies your best thinking across every email, every plan, every decision your cabinet touches. Feed it an untested inherited sentence, and it does the exact same thing to that. (This is the exact gap THE TEAM INSTITUTE was built to close this fall: surfacing what the room already believes before the tool starts repeating it back at scale, which is different work than training your cabinet on the tool itself. Every vendor already offers that part. More on that in a moment.) TQ = IQ × EQ × PQ still holds. What's new is the multiplier. A cabinet with strong IQ and an untested self-image used to produce one flawed decision at a time. The same cabinet, with AI in the loop, can now produce that flawed decision a hundred different ways before lunch: in a strategic plan draft, a parent email, a board memo, and every version will read as confident, because the tool can't tell the difference between confidence and an old wound. THE OLD PLAYBOOK If you want proof this isn't just a Higher Performance Group observation, change management researchers are already redrawing the map. Kotter's 8-Step Change Model has run more transformations than any framework in modern management: create urgency, build a coalition, communicate the vision, empower people to act, anchor the gains. It's built for change that holds still long enough to sequence. A comparative model published this year in the Journal of AI, Robotics & Workplace Automation puts Kotter's eight steps next to a proposed AI Adoption Change Model, and the contrast is the whole argument in one picture. Source: Journal of AI, Robotics & Workplace Automation, Vol. 5 (2026), Henry Stewart Publications. Look at where each model starts. Kotter opens with urgency and a coalition, top-down, already decided. The AI model opens with exploring potential and discovering champions, bottom-up, still being tested. Kotter ends with anchoring the change in culture. The AI model ends with "cultivate AI-driven culture" and loops straight back into exploring again, because the tool never stops shipping new capability long enough for anything to get anchored. That's the structural version of what Kwik is describing at the individual level. AI adoption isn't a project you finish. It's a loop you run, and every pass through that loop amplifies whatever judgment your cabinet brought to it, tested or not. Which is exactly why the next five steps matter more than the eight above them. BUILD BEFORE YOU BORROW Kwik teaches a five-step discipline for exactly this problem, built for one person working with AI. It translates almost perfectly to a cabinet. You just have to run it as a room, not as one person with a laptop. Brainstorm first. Before anyone opens a tool, the cabinet talks through the problem out loud, together, with nothing feeding them an answer. This has nothing to do with whether the tool can be trusted. A room that's never practiced thinking together won't notice when the tool starts thinking for it instead. Understand the real problem. Most cabinets solve the presenting problem (enrollment's soft, a program's underperforming) instead of the one underneath it. Kwik's rule: spend the bulk of your time understanding what's actually broken before anyone reaches for a fix. AI is exceptionally good at answering the wrong question with total confidence. Imagine your own solution before you borrow one. Draft the cabinet's own answer first, even a rough one, before any tool sees the problem. This is the step almost every cabinet skips under deadline pressure, and it's the one that actually builds Team Intelligence. Skip it enough times, and the room stops being able to do it at all. Leverage the tool to stress-test, not to think for you. This is the one step where you deliberately fire the ghostwriter. Kwik's own practice: ask AI to argue against what the room already believes, to name the room's blind spots, to poke holes. Not "write our plan." "Tell us what's wrong with our plan." Different question, completely different outcome, and the only one of the five steps where you want the tool talking back instead of taking dictation. Decide, because the tool never has to live with it. AI has no stake in your decision. It doesn't sit in the parent meeting when the plan fails, or defend the budget line to the board. That accountability doesn't transfer, no matter how good the draft looks. Somebody in the room still has to own it. Five steps. None require new software. All five require your leaders to still be doing the thinking it's currently outsourcing, to the tool, or, just as often, to whichever one of you has quietly become the only person who does the real thinking before anyone else weighs in. (Kwik teaches this in far more depth than one newsletter can hold: his book Limitless and his Kwik Brain podcast go deep on the underlying discipline. No affiliation here, just work worth pointing you to.) THE CASE STUDY This is a composite, drawn from patterns across our work with 987 leadership teams , not one specific president's story. A university cabinet spent the spring drafting its first AI use policy the way most do: one dean built a draft using a chatbot over a weekend, and the cabinet spent forty minutes debating word choices in a document none of them had actually thought through together. The policy read confidently. Nobody in the room could say, if asked directly, what problem it was actually solving. Before the fall rollout, the cabinet ran Build Before You Borrow on that same policy, live, in one meeting. Brainstormed first, out loud, no laptops. Named the real problem: not "we need an AI policy" but "we don't yet agree on what we're willing to let a machine say on our behalf." Drafted their own answer as a room, in plain language, before any tool touched it. Only then brought a draft to AI, and only to argue against it. The resulting policy was four sentences shorter than the first one and, according to the cabinet, the first draft everyone in the room could actually explain from memory without looking at it. Same five people. One real conversation, finally had before the tool had it for them. THE FIRST MEETING You don't need a retreat for this. You need one meeting, early in the semester, run differently than the ones you've been running. Name the sentence (20 minutes). Ask your cabinet directly: what's something this institution believes about itself that nobody's tested in years? Write every answer down without editing them. You're not solving anything yet. You're finding out what you've all been quietly agreeing not to say. Run one live decision through Build Before You Borrow, out loud, before anyone opens a laptop (30 minutes). Pick a real one: the fall enrollment message, the AI policy itself, whatever's actually on this week's agenda. Brainstorm together first. Name the real problem. Draft your own answer as a room. Only then bring in a tool, and only to argue against what you just built. Agree, as a cabinet, on one rule for how AI gets used this year (10 minutes). Not a policy document. One sentence everyone says out loud and means: something like "nothing this tool wrote goes out first without a human draft underneath it." Whatever you land on, make it specific enough that you'd notice the day you broke it. If your first objection is that you don't have sixty extra minutes this month, you're already spending more than that reworking decisions that got made too fast, by whoever talked first in the room. This isn't additional time. It's the same time, spent before the mistake instead of after it. If your second objection is that your team will treat this as one more initiative, they're already operating under an initiative. It's just an unspoken one, and it's been running since before you took the job. THE MATURITY SHIFT Immature leaders think: "We need to move fast before we fall behind on AI." Mature leaders think: "We need to know what we actually believe before we teach a machine to say it for us." Immature leaders let the tool draft first and edit for tone. Mature leaders draft the room's own answer first and let the tool argue with it. Kwik calls the difference between these two postures victim mindset and heroic mindset: whether you let your hardest chapter keep narrating you, or you use it as fuel. It's a private decision about your own institution's story, one nobody else can make for you, and this fall, a machine is about to say that decision out loud, on schedule, to everyone. YOUR TURN Your cabinet is about to find out, in public, at scale, which story it's been running. No scandal required. A machine is about to say it back to everyone, fluently, on schedule, forever. Name it. What's the sentence your cabinet has been running that nobody's tested? Where did it come from, and is it even still true? You don't have to post the answer. But if you're willing to, I'd genuinely like to know what you find. If you already suspect which sentence it is, and you're wondering whether it's about to get amplified before you've even chosen a vendor: that's precisely what the TEAM INTELLIGENCE Assessment is built to surface. Fifteen minutes, no pitch, just a clear read on what your cabinet is actually working with before you put a machine in the room as your ghostwriter. higherperformancegroup.com/team-intelligence-assessment Across the 987 leadership teams we've studied, the cabinets that did this work before scaling anything (a new initiative, a new tool, a new plan) outperformed the ones that scaled first and diagnosed later, by a wide enough margin that "later" stopped being a viable strategy. The point is simple: make sure what gets sped up is actually worth repeating. If this is useful for someone else's first fall cabinet meeting, send it their way before their board asks the same question yours did. Tell them which sentence you found. Somebody in your network is about to let a machine ghostwrite a story they've never actually tested, and this might be the newsletter that stops them in time. Follow DR. JOE HILL and Higher Performance Group . — Dr. Joe Hill, Higher Performance Group | THE TEAM INSTITUTE
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