The Art of Managing Expectations

You’re mentally drained. The discussion persists, growing quicker and louder with each round. It was meant to be the last item on the agenda. A short reflection on how the strategy was rolling out throughout the school, but it quickly degenerated into a shouting match, with each leader defending their position and blaming others.

You stop yourself from rolling your eyes, yet justify it as a suitable reaction to the theatrics and posturing. It continues much, much longer than you hoped, but eventually enough words have landed, and the heat has dissipated.

Glad it’s over, you're already thinking about how to handle the bruises and scars tomorrow.

It’s a fast dash to the supermarket to pick up dinner. You had a late pickup of your 3-year-old from daycare, exacerbated by horrendous traffic. You want something simple and quick, ready in under 10 minutes, that won’t cause a meltdown in a child who hates everything.

But the script isn’t ebbing and flowing as you imagined. A tantrum occurs; it seems today is the day toddlers stop sitting in trolleys. Instead, she wanders slowly through the store, captivated by even the smallest objects; it becomes clear that the haste you wish to apply is not equally valued.

And then that ‘A-ha’ moment.

Managing Expectations Is Harder Than It Sounds

The executive team and the toddler are obviously not the same problem. One desires to execute their strategy. The other has focused on a button in the dairy aisle that ‘moos’ whenever it’s pressed. But both collisions are driven by the same force.

Expectation.

Not the polite kind that appears in board papers. The private kind. The kind that lives in your head and feels so reasonable that it barely registers as an assumption at all.

You expected pace. You expected cooperation. You expected that what mattered to you would be obvious to the other party. In both settings, that confidence was misplaced.

The Trigger of Difficult Expectations

That is what makes managing expectations so difficult. Expectations do not arrive as neutral observations. They arrive loaded with biography, pressure, ego, values, fatigue, habits, and the occasional messiah complex. In executive teams, they also arrive dressed as virtue. Excellence. Accountability. Responsiveness. High performance. Urgency.

All noble words, but often dangerously elastic.

A school executive can sincerely agree on the value of excellence while meaning entirely different things by it. For one leader, excellence means polish. For another, speed. For another, innovation. For another, consistency and low error. And, for another, it means not burning the staff alive in the process.

Same word. Different religion.

That is why managing expectations is not the same as lowering standards. It is the discipline of making standards discussable. Amy Shoenthal makes a similar point in her piece on expectation-setting: teams perform better when expectations are clarified early rather than left to drift into disappointment and rework.

In schools, though, that drift is common. We assume shared language means shared meaning. It does not. It simply means everyone has learned the same vocabulary.

Setting Expectations in Strategic Execution

This is where strategic execution becomes revealing.

Planning is wonderfully forgiving. It allows people to nod at broad intentions and feel aligned. Execution is less sentimental. Execution asks what excellence looks like by Friday. It asks who owns the action, what quality is expected, how much consultation is enough, whether the timeline is real, and what gets sacrificed when resources run thin.

That is when private standards crawl out from under the floorboards.

One executive member thought the paper needed another week of refinement. Another thought it was already too slow. One thought a team had been poorly supported. Another thought they were being precious. One thought the initiative required broad consultation. Another thought, meetings were strangling it.

And now we are no longer discussing strategy.

We are discussing character. Who is committed? Who is difficult? Who “gets it”? Who always drops the ball?

Strategy has become personal because expectations stayed private for too long.

Conflict Can Assist Our Expectation Levels

This is also why some executive conflict is not a sign of dysfunction. Sometimes it is the first honest moment a team has had in months. Positive conflict matters. No school needs an executive team of nodding Labradors. But conflict only remains productive when the team has enough shared standards to argue about the work rather than attack the worth of the people doing it.

That is the distinction many teams miss.

McKinsey’s recent work on team effectiveness pushes against the lazy myths here. Team performance is too often blamed on personalities, chemistry, or the magical presence of one heroic leader. Their argument is sharper: context, structure, alignment, execution, and renewal matter because effective teams are built through behaviours and conditions, not wishful thinking. They also note that teams with a shared and meaningful vision are significantly more likely to outperform.

That should sound familiar to schools.

Executive tension is often treated as a people problem because it is more dramatic and much easier to gossip about over coffee. But much of it is structural. It emerges when broad values are not translated into observable standards. It grows when no one has agreed what “good enough” looks like, and it worsens when high performance is assumed to mean the same thing to everyone in the room.

It rarely does.

Some leaders define high performance as speed under pressure. Others define it as thoughtful judgment. And then others define it as visible output, or sustainable delivery, or high support with high standards.

You get the drift.

Forbes recently framed a related idea well: high expectations do not, by themselves, kill engagement. People disengage when pressure is not matched by clarity, support, psychological safety, and managerial capacity.

That matters in schools because executive teams often praise high performance while quietly rewarding overextension, ambiguity, and emotional endurance.

A team cannot stay healthy if every stretch target is treated as morally binding, every request is treated as urgent, and every resource constraint is treated as a minor inconvenience to be overcome with effort and caffeine.

Which brings us to the awkward bit.

Managing Resource Expectations

Not enough time, personnel, budget, space, energy… the list goes on.

Schools often speak about these as unfortunate constraints on the real work. But that flatters us. Resource limits are not just barriers. They are one of the clearest tests of what the school truly values.

Scarcity forces choice, and we know that choice reveals strategy.

Not every expectation deserves to survive contact with reality. Some expectations are inherited. Some are ego-driven. And some are nostalgic, belonging to a school that existed ten years ago, with a different culture and more room for waste.

An executive team’s job is not simply to keep everything alive. It is to decide what deserves oxygen.

Managing Expectations Requires Hard Conversations

This is the part that executive teams often resist.

It is one thing to talk about alignment in the abstract. It is another to discover that the person beside you has been using the same language as you, while meaning something quite different by it.

Excellence, urgency, accountability, support, and responsiveness.

These words look solid enough in a strategy document. In a live executive environment, they are far less stable. Each person hears them through their own pressure, standards, scars, and sense of what good leadership looks like.

That is why so much frustration inside executive teams feels personal long before anyone realises it is structural.

A leader might view a colleague as slow, while that colleague thinks they are being careful. One sees it as protecting quality, but the other sees it as causing delays. One believes they are respectful of staff capacity, while the other sees indecisiveness. These perceptions aren't driven by bad intentions but are shaped by each person's expectations.

Left untouched, that gap starts to do damage, not all at once. It appears in tone, in irritation, in the stories people begin telling themselves about one another. Not, “we have never really defined what this standard requires,” but, “they always do this.”

Managing Hard Conversations

If a team is going to have hard conversations well, it helps to follow a process rather than relying on personality, confidence, or who happens to speak first.

Here are some simple steps you can take to get the conversation started:

Name the pressure point
Be specific about the issue creating tension. Not “communication has broken down,” but “we seem to have different expectations about turnaround time, consultation, and what counts as a finished piece of work.”
Describe the observable pattern
Concentrate on observable actions rather than character judgments. Highlight recurring behaviours, delays, decisions, bottlenecks, or frustrations that the team can directly observe.
Surface private expectations
Ask each person to explain what they assumed was reasonable, necessary, high quality, urgent, or non-negotiable. This is often where the real divergence appears.
Test the meaning of shared language
Take words like excellence, responsiveness, support, accountability, or urgency and ask what they mean in practice. Teams often discover they have been using the same language with very different definitions.
Bring constraints into the room
Clarify the real limits around time, staffing, budget, energy, or capability. Hard conversations get healthier when reality is allowed to speak.
Identify the trade-offs
Ask about what can be done effectively, what might need to be postponed, what can be scaled back, and what should be discontinued. This helps prevent the discussion from becoming unrealistic.
Agree on a shared standard
Define clear, observable criteria for this issue instead of vague values, so people can practically work towards them.
Set decision rules
Clarify who makes decisions, what needs consultation, when to escalate issues, and how progress will be monitored. Without this clarity, the same tension reemerges, just in a different guise.
Check for genuine commitment
Before closing, ask whether everyone can support the agreed approach. Better to surface hesitation now than discover passive resistance later.
Revisit before resentment builds
Hard conversations often require follow-up. Revisit the agreement promptly to make adjustments before disappointment turns into blame.

Hard conversations are the only true solution. They aren't enjoyable, but they are necessary to shift expectations from feelings into clear language.

What does excellence mean when resources are limited? What degree of finish is truly necessary? How much consultation is sufficient before it turns into avoidance? What are we expecting people to handle that our current staffing, time, and budget cannot support?

Those are not side questions. They are central to execution.

Resource limits do not merely frustrate expectations; they also shape and expose them. They force a school to stop pretending every good thing can be pursued equally and at once. That is where executive strain often begins, because choices always leave someone disappointed.

It is often perceived as failure, but in reality, it is strategy working as intended.

Managing expectations is not about making everyone happy or draining conflict out of the room. It is the slower, more deliberate task of making hidden expectations visible before they harden into resentment. Once that resentment takes hold, people stop solving problems together. They start defending themselves.