John StephensonYou Might Not Have a Leadership Problem. You Might Have an Expectation Problem.
Most leaders walk into a new role, a new business, or a new team expecting progress to look like a straight line. It rarely does. First comes excitement. Then confidence. Then reality. The strategy does not work. Someone quits. Revenue drops. The team pushes back. Something you thought you were good at suddenly exposes how much you still have to learn. And that is the moment a lot of leaders make the wrong diagnosis. Not this is hard, which would be accurate, but maybe I am not supposed to be here, which usually is not. That misdiagnosis ends more leadership runs than incompetence does.
I heard a message this week from Pastor Hope Flask that reframed this better than most leadership content I have read, and it did it without softening anything. Her central claim is that expectations function as a lens. Whatever you expected determines what the same set of facts means to you. Two leaders can face identical resistance in month four of a new role. The one who expected resistance reads it as terrain. The one who expected a clear runway reads it as a verdict. Same data, two completely different decisions, and the difference was set before either of them arrived.
Flask’s message is explicitly a message of faith, and it stays that way here. That is not me preserving the source material out of politeness. It is what I believe too, and I have stopped pretending otherwise in my own work. The business version of leadership writing usually sands the faith off to make the ideas portable, and what survives the sanding is a motivational poster. The faith is not decoration on this framework. It is the load-bearing wall. The third expectation is the one holding the first two up, which becomes obvious by the end.
Expectation One: Expect Battles. Do Not Confuse Opposition With Failure.
Flask makes a distinction that is easy to nod along with and hard to actually hold: there are two ways to get your expectations about opposition wrong, and they fail in opposite directions. Overestimate the opposition and you retreat prematurely, abandoning ground you could have held. Underestimate it and you walk in unprepared, which produces a different kind of collapse. Most leadership advice only addresses one of these, usually by telling you the obstacles are smaller than they look. That is half the problem, and solving half of it badly is how people end up blindsided.
The useful move is not to predict the size of the opposition correctly. You cannot. The useful move is to expect that there will be some, so that its arrival carries no information about whether you belong there. That is the whole function of the expectation. It decouples the presence of difficulty from the question of fit. A leader who has not done that work will spend the first hard quarter relitigating a decision they already made, which is the most expensive possible use of that quarter.
Expectation Two: Expect to Outgrow Your Current Skills
This is Flask’s strongest leadership observation, and it is the one that stings: what got you here may not equip you for what comes next. Not because you were underqualified before, but because the territory changed and the requirements changed with it. Her sharpest illustration is the contrast between a peacekeeper and a peacemaker.
Nearly every leader I know was promoted at least partly for peacekeeping. It reads as maturity. It makes you easy to work with. And it is exactly the skill that stops working the moment you are responsible for outcomes rather than atmosphere. The transition from peacekeeper to peacemaker is not a personality change. It is a capability you have to build on purpose, usually while already in the role that requires it, which is uncomfortable and also the only way it ever happens.
The broader principle generalizes past conflict. The individual contributor who gets promoted for output now needs to develop judgment about other people’s output. The founder who got traction on instinct now needs systems that work when they are not in the room. In each case the new requirement is not an upgrade of the old skill. It is a different skill, and the leader usually discovers this the hard way, about four months in, right as confidence is about to fall off a cliff.
Why Your Confidence Crashes in New Territory
Here is where Flask connects her message to something most business leaders already half-know and consistently misapply. The Dunning-Kruger curve is usually deployed as an insult, a way of saying someone is too stupid to know they are stupid. That is not what it is useful for. Read as a developmental sequence, it describes almost exactly what happens to a competent person entering territory they have not occupied before. The confidence spike is not arrogance. It is what not-knowing feels like from the inside. And the collapse that follows is not failure. It is the first accurate read you have had.
The stage worth dwelling on is stage four, and Flask’s treatment of it is the reason this framework is worth more than the standard version. The Valley of Despair is where people quit or get permanently stuck. Not because the work got harder at that specific moment, but because the interpretation turned. Confidence is at its lowest exactly when the picture is becoming most accurate, and almost nobody is prepared for that inversion. It feels like evidence. It is actually just the shape of the curve.
Her practical answer to the valley is mentorship. Experienced leaders who have been through the same sequence can tell you which stage you are standing in, and that information alone changes the decision. A leader in the valley who thinks they are failing quits. The same leader, told by someone credible that this is stage four and stage five comes next, stays. The work is identical. The expectation is what changed.
What the Three Expectations Look Like Together
Flask’s three expectations are not a checklist. They stack, and the third one is load-bearing for the other two.
The Part Most Leadership Content Will Not Say
Flask’s conclusion is where the faith foundation stops being background and starts being the actual argument. Her claim is that the promised land is not built on performance, giftedness, or experience. It rests on God’s promises. For a business audience that line can read as a pivot away from practical leadership. I would argue it is the most practical thing in the message, and here is why.
Every other foundation available to a leader fluctuates. Performance is the obvious one: it is a lagging measure of a dozen variables you partly control, and it will be bad sometimes for reasons that have nothing to do with you. Giftedness is real and also fixed, which means it runs out exactly when the territory exceeds it. Experience is accumulating but always behind, since by definition you have no experience in the territory you just entered. Build your confidence on any of the three and you have built it on something that will be lowest precisely when you need it most, which is in the valley.
Confidence changes.
Circumstances change.
Your foundation determines whether you keep moving.
That framing is my leadership adaptation of Flask’s point rather than her words. But the logic underneath it is hers, and it holds whether or not you share her faith. A leader whose sense of legitimacy is anchored to something outside their last quarter can survive a bad quarter. A leader whose legitimacy is the last quarter cannot, and will make increasingly defensive decisions to protect it. You have watched this happen. Possibly you have been it.
The valley is not a verdict. It is a stage, and it has a stage after it.
Difficulty in new territory is not information about whether you belong there. It is information about where you are on the curve. Leaders who expect battles stop reading resistance as rejection. Leaders who expect to outgrow their current skills stop reading inadequacy as disqualification. Leaders anchored in something beyond performance stop reading a bad quarter as an identity crisis.
Your expectations are set before you enter. They determine what every subsequent fact will mean to you. Which makes expectation-setting the highest-leverage work you can do at the start of anything.
Most leaders do not quit because the territory was too hard. They quit because nobody told them the valley was on the map.
Common Questions
What is the Valley of Despair in the Dunning-Kruger curve?
The Valley of Despair is the stage where confidence collapses after reality exposes how much you did not know, following the early confidence spike sometimes called Mount Stupid. It is where most people quit or get permanently stuck, because they misread the confidence drop as evidence they are not capable. In leadership terms the valley is not failure. It is the first moment you are seeing the role accurately, and mentorship from more experienced leaders is what most reliably carries people through it.
What is the difference between a peacekeeper and a peacemaker?
A peacekeeper suppresses conflict to maintain the appearance of calm. A peacemaker enters conflict and works toward genuine resolution. Pastor Hope Flask uses this contrast to show that new territory requires different capabilities than the ones that got you here. Peacekeeping is often rewarded in early leadership because it looks like harmony, but it defers problems rather than resolving them. Peacemaking costs more in the moment and is the skill most leaders have to build deliberately when they move into larger roles.
What are the three expectations for entering new territory?
Expect battles, because resistance is a normal feature of new ground rather than a signal you chose wrong. Expect to need new skills, because the capabilities that carried you into the territory are often not the ones required to hold it. Expect God’s faithfulness, which anchors confidence in something that does not fluctuate with performance, giftedness, or experience.
Why do leaders quit during the Valley of Despair?
Because they make the wrong diagnosis. When confidence collapses and difficulty increases, the instinctive reading is that the role was a mistake or that they are not capable. The alternative reading is that the discomfort is accurate self-assessment arriving for the first time. Flask notes that overestimating opposition causes leaders to retreat prematurely while underestimating it causes them to enter unprepared, and both are expectation failures rather than capability failures.
Who is Hope Flask?
Hope Flask is the Lead Pastor of Outside The Walls Church and Ministries in Newton, Kansas, a congregation she founded with her husband Tim in 2017, building on a music and worship ministry they started in 2015. She has over eleven years of experience in preaching, leading worship, and songwriting, and has been a member of Foursquare since 2020.
John Stephenson
