{"id":1912,"date":"2026-04-08T00:24:59","date_gmt":"2026-04-08T00:24:59","guid":{"rendered":"https:\/\/yankagolemin.com\/?p=1912"},"modified":"2026-06-20T00:28:00","modified_gmt":"2026-06-20T00:28:00","slug":"why-advice-fails-at-the-top","status":"publish","type":"post","link":"https:\/\/yankagolemin.com\/?p=1912","title":{"rendered":"Why Advice Fails at the Top"},"content":{"rendered":"\t\t
\n\t\t\t\t
\n\t\t\t\t
\n\t\t\t\t\t

Why Advice Fails at the Top<\/h2>\t\t\t\t<\/div>\n\t\t\t\t
\n\t\t\t\t\t\t\t\t\t

Senior leaders are often the worst-advised people in any organisation. Not for lack of advisors \u2014 because everyone around them has something to lose from candour.<\/p>\t\t\t\t\t\t\t\t<\/div>\n\t\t\t\t

\n\t\t\t\t\t\t\t\t\t

There is a peculiar irony at the top of most organisations. The further someone rises, the more advisors accumulate around them \u2014 consultants, bankers, lawyers, coaches, board members, a widening circle of people whose formal role is to provide counsel. And yet the quality of advice a person actually receives tends to decline as they rise, not improve. This is not a paradox. It is a structural feature of seniority, and understanding why it happens matters more than almost anything else I have observed in advising people at this level.<\/p>

The mechanism is simple enough to state and difficult enough to fix that most organisations never manage it. Every advisor surrounding a senior leader has a relationship to protect, a future engagement to secure, or a position within the organisation that depends, to some degree, on the leader’s continued goodwill. This is true of external consultants who want the next contract, internal executives who report into the leader’s structure, and even board members whose own standing is bound up with the leader’s success. None of these people are acting in bad faith. They are responding rationally to an incentive structure that makes candour expensive and agreement cheap. The result is an advisory environment that is wide in volume and narrow in honesty \u2014 many voices, most of them calibrated, consciously or not, toward what will be well received.<\/p>\t\t\t\t\t\t\t\t<\/div>\n\t\t\t\t

\n\t\t\t\t\t\t\t\t\t

An advisory environment that is wide in volume and narrow in honesty \u2014 many voices, most of them calibrated toward what will be well received.<\/p>\t\t\t\t\t\t\t\t<\/div>\n\t\t\t\t

\n\t\t\t\t\t\t\t\t\t

I have watched this dynamic operate at close range in situations of real consequence, and what is striking is how rarely it looks like flattery in any crude sense. It is subtler than that. It shows up as a tendency to frame difficult information in its most palatable version. It shows up as advisors waiting for the leader to indicate a preference before fully forming their own view, then discovering, with apparent independence, that their analysis happens to align with it. It shows up as genuine concerns being raised once, gently, and then not repeated when the leader’s body language suggests they were not well received. None of this is dishonesty in the way the word is usually meant. It is something closer to a slow, mutual negotiation toward the version of the truth that is least costly for everyone in the room to say.<\/p>

The leader, for their part, rarely experiences this as a problem, because the mechanism is largely invisible from the inside. What they experience instead is a steady stream of advice that seems to confirm the wisdom of their instincts more often than not \u2014 which feels, reasonably, like validation rather than distortion. The less visible cost is that their model of their own judgment becomes increasingly disconnected from how that judgment is actually being received and processed by the people around them. They begin to mistake the absence of disagreement for the absence of doubt. The two are not the same, and the gap between them is precisely where the most expensive mistakes tend to originate.<\/p><\/div>\t\t\t\t\t\t\t\t<\/div>\n\t\t\t\t

\n\t\t\t\t\t\t\t\t\t

They begin to mistake the absence of disagreement for the absence of doubt.<\/p>\t\t\t\t\t\t\t\t<\/div>\n\t\t\t\t

\n\t\t\t\t\t\t\t\t\t

What makes this difficult to solve through conventional means is that most of the obvious remedies do not actually address the underlying incentive. Hiring more advisors does not help if the new advisors face the same structural pressure as the old ones. Explicitly asking for honest feedback does not help much either, because the people being asked still bear the cost of providing it, regardless of how sincerely the invitation was extended \u2014 and they know, correctly, that the invitation can be withdrawn. Even board structures designed specifically to provide independent oversight are not immune; board members who depend on the leader’s support for their own continued role, or whose other professional relationships intersect with the leader’s network, are subject to a milder version of the same pressure.<\/p>

The condition that actually produces candour is structural independence, not goodwill or good intentions. An advisor who has nothing to gain from being agreed with and nothing to lose from being disagreed with is rare, specifically because almost every advisory relationship is embedded in some network of ongoing professional or financial interest. This is not a criticism of any individual advisor’s character. It is an observation about what incentive structures reliably produce, regardless of the character of the people inside them. The few advisory relationships that escape this pattern tend to share a common feature: the advisor’s continued engagement does not depend on the leader’s approval of any particular piece of advice, and the advisor has deliberately limited their own exposure to the kind of ongoing interest that would make candour costly.<\/p>

This is a harder thing to build than it sounds, because it requires the leader to actively resist the natural pull toward advisors who make them feel more certain, and to seek out the rarer kind who are willing to leave them less certain, more often, in service of a clearer eventual picture. Most leaders, understandably, do not seek this out deliberately \u2014 it tends to arrive, if it arrives at all, through a relationship that predates their seniority, or through a deliberate and somewhat uncomfortable choice to bring in someone whose only stake in the relationship is the quality of the judgment they provide. The leaders I have seen navigate high-stakes decisions most successfully are, almost without exception, the ones who have at least one such relationship in place before the decision that requires it arrives. By the time the need is obvious, it is usually too late to build the independence the moment requires.<\/p><\/div><\/div>\t\t\t\t\t\t\t\t<\/div>\n\t\t\t\t

\n\t\t\t\t\t\t\t
\n\t\t\t\n\t\t\t\t\t\t<\/span>\n\t\t<\/div>\n\t\t\t\t\t\t<\/div>\n\t\t\t\t
\n\t\t\t\t\t\t\t\t\t

Yanka Golemin provides private counsel to founders and principals navigating high-consequence decisions. Inquiries: counsel-inquiry@yankagolemin.com<\/p>\t\t\t\t\t\t\t\t<\/div>\n\t\t\t\t

\n\t\t\t\t\t\t\t
\n\t\t\t\n\t\t\t\t\t\t<\/span>\n\t\t<\/div>\n\t\t\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t\t\t<\/div>\n\t\t","protected":false},"excerpt":{"rendered":"

Why Advice Fails at the Top Senior leaders are often the worst-advised people in any organisation. Not for lack of advisors \u2014 because everyone around them has something to lose from candour. There is a peculiar irony at the top of most organisations. The further someone rises, the more advisors accumulate around them \u2014 consultants, bankers, lawyers, coaches, board members, a widening circle of people whose formal role is to provide counsel. And yet the quality of advice a person actually receives tends to decline as they rise, not improve. This is not a paradox. It is a structural feature of seniority, and understanding why it happens matters more than almost anything else I have observed in advising people at this level. The mechanism is simple enough to state and difficult enough to fix that most organisations never manage it. Every advisor surrounding a senior leader has a relationship to protect, a future engagement to secure, or a position within the organisation that depends, to some degree, on the leader’s continued goodwill. This is true of external consultants who want the next contract, internal executives who report into the leader’s structure, and even board members whose own standing is bound up with the leader’s success. None of these people are acting in bad faith. They are responding rationally to an incentive structure that makes candour expensive and agreement cheap. The result is an advisory environment that is wide in volume and narrow in honesty \u2014 many voices, most of them calibrated, consciously or not, toward what will be well received. An advisory environment that is wide in volume and narrow in honesty \u2014 many voices, most of them calibrated toward what will be well received. I have watched this dynamic operate at close range in situations of real consequence, and what is striking is how rarely it looks like flattery in any crude sense. It is subtler than that. It shows up as a tendency to frame difficult information in its most palatable version. It shows up as advisors waiting for the leader to indicate a preference before fully forming their own view, then discovering, with apparent independence, that their analysis happens to align with it. It shows up as genuine concerns being raised once, gently, and then not repeated when the leader’s body language suggests they were not well received. None of this is dishonesty in the way the word is usually meant. It is something closer to a slow, mutual negotiation toward the version of the truth that is least costly for everyone in the room to say. The leader, for their part, rarely experiences this as a problem, because the mechanism is largely invisible from the inside. What they experience instead is a steady stream of advice that seems to confirm the wisdom of their instincts more often than not \u2014 which feels, reasonably, like validation rather than distortion. The less visible cost is that their model of their own judgment becomes increasingly disconnected from how that judgment is actually being received and processed by the people around them. They begin to mistake the absence of disagreement for the absence of doubt. The two are not the same, and the gap between them is precisely where the most expensive mistakes tend to originate. They begin to mistake the absence of disagreement for the absence of doubt. What makes this difficult to solve through conventional means is that most of the obvious remedies do not actually address the underlying incentive. Hiring more advisors does not help if the new advisors face the same structural pressure as the old ones. Explicitly asking for honest feedback does not help much either, because the people being asked still bear the cost of providing it, regardless of how sincerely the invitation was extended \u2014 and they know, correctly, that the invitation can be withdrawn. Even board structures designed specifically to provide independent oversight are not immune; board members who depend on the leader’s support for their own continued role, or whose other professional relationships intersect with the leader’s network, are subject to a milder version of the same pressure. The condition that actually produces candour is structural independence, not goodwill or good intentions. An advisor who has nothing to gain from being agreed with and nothing to lose from being disagreed with is rare, specifically because almost every advisory relationship is embedded in some network of ongoing professional or financial interest. This is not a criticism of any individual advisor’s character. It is an observation about what incentive structures reliably produce, regardless of the character of the people inside them. The few advisory relationships that escape this pattern tend to share a common feature: the advisor’s continued engagement does not depend on the leader’s approval of any particular piece of advice, and the advisor has deliberately limited their own exposure to the kind of ongoing interest that would make candour costly. This is a harder thing to build than it sounds, because it requires the leader to actively resist the natural pull toward advisors who make them feel more certain, and to seek out the rarer kind who are willing to leave them less certain, more often, in service of a clearer eventual picture. Most leaders, understandably, do not seek this out deliberately \u2014 it tends to arrive, if it arrives at all, through a relationship that predates their seniority, or through a deliberate and somewhat uncomfortable choice to bring in someone whose only stake in the relationship is the quality of the judgment they provide. The leaders I have seen navigate high-stakes decisions most successfully are, almost without exception, the ones who have at least one such relationship in place before the decision that requires it arrives. By the time the need is obvious, it is usually too late to build the independence the moment requires. Yanka Golemin provides private counsel to founders and principals navigating high-consequence decisions. Inquiries: counsel-inquiry@yankagolemin.com<\/p>\n","protected":false},"author":1,"featured_media":0,"comment_status":"closed","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[29],"tags":[],"class_list":["post-1912","post","type-post","status-publish","format-standard","hentry","category-counsel"],"acf":[],"_links":{"self":[{"href":"https:\/\/yankagolemin.com\/index.php?rest_route=\/wp\/v2\/posts\/1912","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/yankagolemin.com\/index.php?rest_route=\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/yankagolemin.com\/index.php?rest_route=\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/yankagolemin.com\/index.php?rest_route=\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/yankagolemin.com\/index.php?rest_route=%2Fwp%2Fv2%2Fcomments&post=1912"}],"version-history":[{"count":4,"href":"https:\/\/yankagolemin.com\/index.php?rest_route=\/wp\/v2\/posts\/1912\/revisions"}],"predecessor-version":[{"id":1916,"href":"https:\/\/yankagolemin.com\/index.php?rest_route=\/wp\/v2\/posts\/1912\/revisions\/1916"}],"wp:attachment":[{"href":"https:\/\/yankagolemin.com\/index.php?rest_route=%2Fwp%2Fv2%2Fmedia&parent=1912"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/yankagolemin.com\/index.php?rest_route=%2Fwp%2Fv2%2Fcategories&post=1912"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/yankagolemin.com\/index.php?rest_route=%2Fwp%2Fv2%2Ftags&post=1912"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}