“Clear is kind.” Brené Brown
A surprising number of leadership challenges begin at the moment a leader forms a clear picture of success and assumes, often unconsciously, that picture is shared.
The senior leaders I have worked with over the years spend decades developing expertise, judgment, and pattern recognition. They learn to anticipate risks, identify opportunities, understand stakeholder dynamics, and recognize quality and scalability at a glance. Much of this knowledge becomes deeply internalized. What once required deliberate thought eventually feels self-evident and this creates a subtle leadership challenge.
The more experienced we become, the easier it is to mistake personal clarity for collective understanding.
Brené Brown describes a stealth expectation as an expectation that remains unspoken while carrying the emotional force of an agreement. The expectation exists fully in one person’s mind, complete with standards, assumptions, context, and desired outcomes. Others move forward with a different picture, often unaware that a more detailed version exists.
The resulting tension tends to build as work progresses, energy is invested, conversations move forward and deliverables arrive. A reaction emerges from this cadence that tends to catch others off guard because the genuine effort and outcomes somehow fell short of what the leader envisioned.
At this point, many organizations begin examining execution and my approach is often to do a deep inquiry into communication.
Chris Argyris’ work on the Ladder of Inference offers insight into why stealth expectations occur so frequently. Argyris observed that human beings continuously move from observation to interpretation, selecting data, assigning meaning, making assumptions, drawing conclusions, and forming beliefs. The process unfolds rapidly and largely outside conscious awareness.
Leaders often climb this ladder with remarkable speed because experience allows them to recognize patterns quickly. As they review a project update or consider a proposal assumptions fill the space between what is present and what is absent. Assumptions may sound internally like, ”the team understands the stakeholder landscape, the risks are obvious, the political implications are clear, we all know what success looks like.”
By the time these assumptions crystallize into expectations, they feel entirely reasonable and in many cases, they are reasonable. The challenge is the team never had access to the leader’s full thought process and simultaneously an invisible expectation has entered the system.
Slowly, as this gap becomes wider, team members receive feedback based on criteria they did not know existed. Leaders begin investing additional time reviewing work, refining direction, and revisiting conversations that seemed straightforward from the beginning. Over time, confidence starts to erode on both sides of the relationship. I have worked with leaders navigating this gap who start to question the judgment of those on the project and I have worked with team members who begin to question themselves, and as trust slowly erodes, it becomes clear that capability is typically not the problem. The issue is that one person is evaluating work against a picture that was never fully painted.
This dynamic becomes particularly important in leadership cultures that value autonomy and accountability. Most leaders want teams that think independently, exercise sound judgment, and take ownership. These qualities emerge when expectations are visible enough to support intelligent decision-making. People cannot consistently exercise judgment against standards they cannot see.
Brown offers a practical discipline she calls painting done. I call it envisioned future. Either way, in my experience working with senior leaders, it is one of the most powerful tools available. The reason for its success is that it tends to unearth the stealth expectations before they gain momentum and brings them into the light.
Painting done asks leaders to describe success with sufficient richness that others can see the finished picture before they begin the work. The conversation includes context, purpose, intended impact, stakeholder considerations, constraints, and the reasoning that informs the leader’s expectations. It also includes a vision of what success will look like, feel like, sounds like and who will be celebrating.
Painting done is ultimately an exercise in making thinking visible. It invites leaders to externalize assumptions that experience has taught them to carry internally.
Several practices can strengthen this discipline.
Surface the Invisible Criteria
Before assigning significant work, pause long enough to identify the standards operating beneath the request.
Ask yourself:
- What would make this outcome exceptional?
- What concerns would immediately lower my confidence in the result?
- What assumptions am I making about what this person already understands?
These questions often reveal expectations that have not yet entered the conversation.
Distinguish the Task from the Purpose
The most powerful leadership communication comes when people understand why the work matters.
Consider sharing:
- What decision will this work influence?
- Who will rely on the outcome?
- What larger objective does it support?
- Why is this important now?
Context strengthens judgment because it allows people to make informed choices throughout the process.
Examine Your Own Ladder
The Ladder of Inference becomes particularly valuable when setting expectations and also when they are not met.
Before concluding that expectations were missed, consider:
- What did I actually observe?
- What assumptions shaped my interpretation?
- Which expectations were explicitly discussed?
- Which expectations remained stealth?
This practice frequently uncovers opportunities for greater clarity and stronger partnership.
Invite Shared Definition
One of the most effective ways to test alignment involves asking others to describe success from their perspective before work begins (painting done, envisioned future or whatever title you love).
Questions such as:
- What do you believe matters most here?
- Where do you see ambiguity?
- What is your ‘why’ for working on this project?
- What challenges do you anticipate?
- What are the outcomes you envision celebrating and with whom? When?
What makes stealth expectations particularly consequential for senior leaders is that they accumulate alongside expertise. Years of experience compress knowledge into instinct and strategic considerations become second nature. Organizational context feels like the very air some leaders breathe and therefore the capabilities that strengthen leadership judgment can also make expectations increasingly difficult to see.
Painting done requires a different form of leadership presence because it asks leaders to translate instinct into language and creating the conditions for others to meet them. The strongest leaders I know communicate expectations with remarkable transparency. They help others understand the landscape surrounding a decision rather than offering only the destination. This clarity generates confidence and when team members feel confident they take more ownership and accountability for the success of the whole.
At times I have worked with leaders who wonder if their expectations are unreasonable or if their expectations are too high. The deeper question is whether the people around us have been given access to the picture we are using to evaluate success.
Once the picture becomes visible, the entire energy shifts. Many thought leaders in history have expressed a similar idea, that stealth expectations are resentments under construction.
So I will leave you with this question… What picture are you currently asking others to paint that only you can see?
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