There is a natural tendency, over the course of a long advisory relationship, for the advice to become more comfortable. The adviser learns what the client responds well to. The client learns what kind of input the adviser tends to provide. A shared vocabulary develops. The relationship becomes easier, which is, up to a point, a sign that it is working.
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Beyond that point, it is actually a sign that something important has been lost.

The Comfort Gradient

The problem is not that long advisory relationships become dishonest. We need to reframe our understanding of successful relationships. Acknowledging when they become selective in ways that are difficult to detect from inside the relationship. The adviser, unconsciously, begins to weight their observations towards the ones they know will land well. The client, unconsciously, begins to discount the observations that challenge their existing position. This is not because they dismiss them, but because the relationship has become too comfortable for the adviser to make them forcefully enough.
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This is the comfort gradient. It develops slowly, it is never deliberate, and it produces advice that is technically accurate but strategically deficient. This requires decentring because the most important input an adviser can provide is the one the client most needs to hear, not the one they most want to.

The Value of Productive Friction

The advisory relationships that produce the best outcomes over time are not the most harmonious ones. Keuk Consulting finds that they are more often the ones where both parties have enough mutual respect to sustain disagreement. One where the relationship maintains static – the adviser is confident enough in the relationship to deliver an unwelcome conclusion, and the client is secure enough in the adviser's intentions to receive it without defensiveness.
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This is productive friction. It requires a specific kind of trust that comes from an adviser always leading with honesty, not supportiveness. The client who has that kind of relationship with their adviser has something that cannot be replicated by any amount of research or analysis: where they have a person in the room who will tell them what they actually think.

A Practical Test

There is a straightforward way to assess whether an advisory relationship has retained its productive friction: think of the last significant decision the client made that the adviser had reservations about. Did the adviser express those reservations clearly, specifically, and with enough persistence to ensure they were genuinely considered? Or did they note them briefly and defer to the client's preference?
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If the answer is the latter, the relationship has begun to drift towards comfort. That is not a reason to end it. See this as an opportunity to reset it. A moment to have an explicit conversation about what the advisory relationship is for and to re-establish the expectation that honest, direct counsel is the standard both parties are committed to.
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The adviser who agrees with you consistently is not a trusted partner. They are a clouded mirror. The one worth keeping is the one who, on occasion, makes the conversation harder because they know that is precisely what the situation requires.