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Why Leadership Teams Need Different Conversations at Different Stages

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Why leadership teams need different conversations at different stages of growth, and why avoidance is the instinctive but incomplete explanation.

The symptom

Consider an organisation where an employee is managed out after two years, with no documented performance concerns anywhere in their file. The instinctive explanation is manager avoidance — a manager who found difficult conversations uncomfortable and quietly let a preventable situation run its course until the only remaining option was separation.

What leaders usually conclude

That explanation assumes the conversations never happened. It is a natural first assumption, because an empty file looks exactly like silence from the outside, and manager avoidance of difficult conversations is common enough to be a reasonable default guess. It also happens to be the more comfortable explanation for an organisation to reach, since it locates the failure in one identifiable person’s discomfort rather than in a communication process the wider organisation has never examined.

What the evidence suggests

Here, the conversations did happen — several times, in fact, raised verbally and framed gently. The employee, for their part, reports having genuinely understood these as minor observations rather than as performance issues requiring a change in direction. Feedback was given. It was not received as feedback. This is a meaningfully different failure from silence, and treating the two as interchangeable — both producing an empty file — obscures a distinction that matters for anyone trying to understand what actually went wrong and for whom.

This gap — between what a manager believes they communicated and what an employee understood — is exactly the space Amy Edmondson’s research on psychological safety helps explain, though not in the direction most people expect. Her Harvard Business School field study across 51 manufacturing teams found that psychological safety predicts learning behaviour, meaning people’s willingness to surface, question, and clarify what they’ve heard rather than simply accepting it. A gently framed piece of feedback, delivered in an environment where pushing back or asking “wait, is this serious?” doesn’t feel safe or normal, is far more likely to be absorbed as a minor comment than as a signal requiring real change — precisely because clarifying it would require the kind of open exchange that safety enables and its absence suppresses.

Michael Beer and Russell Eisenstat’s research on strategy implementation barriers adds a structural dimension: they identify unclear priorities and poor vertical communication among the “silent killers” that block organisations from learning — barriers that are, by their description, mutually reinforcing and often invisible to leadership precisely because no single instance looks like a failure. A manager who has genuinely raised a concern several times, gently, has done something that looks from above like adequate communication. Whether it functioned as communication depended on a second, harder-to-observe condition: whether the recipient had genuine room to ask what it actually meant.

Both employee and manager, in this scenario, were acting reasonably given what each could see. The manager delivered the message and could point to having done so, repeatedly. The employee heard something gentle and reasonably concluded it was minor, because gentleness is usually read as a signal of how serious something is, not just how it is being delivered. Neither party had any reliable way to detect the mismatch in real time, because detecting it would have required exactly the kind of open follow-up question that the mismatch itself was quietly discouraging.

Why the right conversation changes with stage

This is where organisational scale matters directly. In a very small organisation, feedback tends to happen inside an ongoing, high-frequency relationship — enough repeated, informal contact that ambiguity in any single exchange gets corrected naturally over time, through follow-up conversations neither party needs to schedule deliberately. As organisations grow and formal structure replaces some of that frequency, a single, gently framed conversation increasingly has to do the entire job on its own, with no natural mechanism to catch a misunderstanding before it compounds. The content of the message here did not need to change between a five-person team and a five-hundred-person one. What changed is how much weight a single exchange has to carry, and how much structural support exists to confirm whether it landed — which is precisely what shrinks as an organisation scales, unless something deliberately replaces it. The scenario above is a useful illustration of exactly this point: nothing about the manager’s intent or the employee’s good faith needed to be different for the same conversation to function well in a five-person team and fail silently in a five-hundred-person one.

For how this pattern presents in other kinds of organisation, see other sectors.

Questions worth considering

  1. After a difficult message is delivered, is there any mechanism to confirm what the other person actually understood — or is delivery treated as the end of the process?
  2. Would a gently framed comment, repeated several times, read as serious to someone hearing it for the first time?
  3. As this organisation has grown, has anything replaced the informal, high-frequency contact that used to catch misunderstandings naturally?
  4. If the employee in this scenario had been asked directly to summarise what they had just been told, would the gap have surfaced sooner?
  5. How would a manager know, in the moment, whether a gently delivered message had actually registered as serious?

More on this topic: Leadership.

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Sources

Michael Beer and Russell A. Eisenstat, “The Silent Killers of Strategy Implementation and Learning,” Sloan Management Review (now MIT Sloan Management Review), 41(4), 2000, pp. 29–40.

Amy C. Edmondson, “Psychological Safety and Learning Behavior in Work Teams,” Administrative Science Quarterly, 44(2), 1999, pp. 350–383.

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Frequently Asked Questions

Research on psychological safety suggests that whether feedback is understood as serious depends heavily on whether the recipient feels able to question or clarify it in the moment — a condition separate from how many times it was delivered or how it was worded.
It can look identical from the outside — an empty performance file either way. The distinguishing evidence is whether the conversations actually took place, which changes where the underlying issue is likely to be: in the delivery, or in whether it was safe to ask for clarification. The two require different responses, which is exactly why the distinction is worth establishing before assuming either one.
Smaller organisations often correct misunderstandings naturally through frequent informal contact. As formal structure replaces that frequency, a single conversation has to carry more weight with less natural opportunity to confirm it landed as intended.
That’s outside what this article covers. The aim here is to describe why gently delivered feedback can go unreceived, not to prescribe a specific communication method.
Yes, according to the page. In its example the conversations happened several times, raised verbally and framed gently, but the employee understood them as minor observations rather than performance issues. The page treats this as a meaningfully different failure from silence, even though both leave an empty file, and says treating them as interchangeable obscures the distinction.
Because gentleness is usually read as a signal of how serious something is, not only of how it is being delivered. The page says the employee reasonably concluded the observations were minor, while the manager could point to having raised them repeatedly. Both acted reasonably given what each could see, and neither had a reliable way to detect the mismatch in real time.
It assumes the conversations did not happen, which is a natural initial assumption because an empty file looks like silence and avoidance of difficult conversations is common. The page adds that it is also the more comfortable conclusion, locating the failure in one person’s discomfort rather than in a communication process the wider organisation has not examined.
They identified unclear priorities and poor vertical communication among the “silent killers” that block organisations from learning, barriers that are mutually reinforcing and often invisible to leadership because no single instance looks like a failure. The page notes that a manager who raised a concern several times appears to have communicated adequately; whether it functioned depended on whether the recipient had room to ask what it meant.