The First Ninety Days of a CHRO Advisory Engagement: What Gets Clarified

Every CHRO advisory engagement I have entered has begun with the same implicit question from the CHRO, usually unspoken in the first conversation but present in the quality of their attention and the specificity of what they choose to share: is this going to be useful, or is this going to be another conversation that produces good frameworks and no practical traction? The first ninety days of the engagement are, in my experience, the period in which that question gets answered. Not through a formal evaluation, but through the accumulation of moments where the advisory relationship either proves itself capable of addressing the real decisions the CHRO is carrying, or reveals itself to be operating at a level of abstraction that does not connect to the CHRO’s working reality.

I want to describe what the first ninety days of a CHRO advisory engagement actually look like, because the received description of executive advisory relationships, careful and structured and professionally detached, does not capture the quality of what needs to happen in those ninety days for the relationship to be genuinely useful. What needs to happen is a rapid and specific act of mutual understanding: the CHRO needs to understand what the advisory relationship can actually provide, and the advisor needs to understand the specific decisions, the specific relationships, and the specific structural constraints that are shaping the CHRO’s reality at this moment. Without that specific understanding, the advisory relationship operates on generalisations, and generalisations are not what CHROs need.

The first ninety days clarify several things that are not immediately visible in the initial conversations. They clarify the genuine strategic priorities of the CHRO versus the operational urgencies that consume most of their time. They clarify the specific relationships that are most enabling and most constraining in the CHRO’s context. They clarify the decisions that are actively open and those that are nominally open but have been effectively decided. And they clarify the CHRO’s own relationship with uncertainty and complexity, the way they think through decisions that do not have clear answers, the places where they have strong instincts and the places where they are genuinely unsure. KNOWING THESE THINGS SPECIFICALLY, rather than as general professional assessments, is what enables the advisory relationship to be useful rather than merely interesting.

The first month of a CHRO advisory engagement is a diagnostic phase, even if neither party explicitly names it as such. The CHRO is sharing decisions they are working through, relationships they are navigating, challenges they are facing, and the advisor is doing two things simultaneously: engaging substantively with the content the CHRO is sharing, and building a map of the CHRO’s world, specifically the patterns in what they raise and what they do not raise, the decisions they find easy and those they find genuinely difficult, the relationships they discuss with energy and those they discuss with guardedness.

What consistently emerges in this diagnostic phase, across every CHRO advisory engagement I have been part of, is a distinction between the presenting challenges and the underlying ones. The presenting challenge is typically the one that prompted the CHRO to seek advisory support in the first place: a specific strategic challenge, a relationship difficulty, a leadership team dynamic, a function restructuring. The underlying challenges are the structural and relational constraints that are making the presenting challenge more difficult than it would otherwise be. THE PRESENTING CHALLENGE CAN OFTEN BE RESOLVED with reasonable professional judgment. The underlying challenges require a different kind of attention, one that addresses the structural conditions rather than the presenting symptoms.

In one recent engagement, the presenting challenge was a tension in the executive team around a talent decision that had been made without sufficient consultation. The underlying challenge, which became visible over the first four weeks, was a pattern in the CHRO’s relationship with the executive team where she was consistently positioned as the person who raised concerns after decisions had been made, rather than as a voice that shaped decisions while they were still open. That positional pattern was not the result of the talent decision; it was the context in which the talent decision had occurred, and it was the thing that needed to be addressed if the CHRO’s strategic contribution was to change substantially. The talent decision conversation was resolved within a few weeks. The positional pattern took the full ninety days to begin to shift.

The first ninety days answer a set of questions that the CHRO may not have articulated explicitly but that are the structural foundation on which the advisory relationship’s usefulness depends. The first is the question of what the CHRO actually controls versus what they have influence over versus what they neither control nor influence but must navigate. This distinction is more contested than it appears, because CHROs vary significantly in how they assess their own sphere of influence, and CHROS WHO CONSISTENTLY OVERESTIMATE THEIR INFLUENCE make different kinds of strategic errors than those who underestimate it. Getting this picture specific and honest is one of the most practically useful things the first ninety days can produce.

The second question is where the CHRO’s own thinking is strongest and where it has systematic blind spots. This is not a coaching question about self-awareness; it is a strategic advisory question about where the CHRO needs the most substantive external input and where they need only a thinking partner to structure their own reasoning. CHROs with deep functional expertise and strong business acumen often have blind spots around their own relational dynamics and the way they are perceived by the executive team. CHROs with strong relational intelligence and high political awareness sometimes have blind spots around the functional rigour of HR practice design. Knowing which is the case changes the nature of the advisory intervention significantly.

The third question is about priorities: of all the things on the CHRO’s plate, which ones will have the most durable impact on the organisation’s capability and strategic direction, and which are urgent but not strategically significant? The first ninety days of the advisory relationship are partly an exercise in prioritisation, helping the CHRO step back from the operational urgency that consumes the diary and identify the two or three things that deserve sustained, high-quality attention over the following twelve to eighteen months.

Across the CHRO advisory engagements I have conducted, several structural challenges emerge with remarkable consistency in the first ninety days, regardless of sector or organisation size. They are worth naming explicitly because their consistency suggests they are structural properties of the CHRO role rather than individual circumstances.

The first is the absence of a clear mandate. Most CHROs know their formal responsibilities, but the strategic expectations of the role, what the CEO and board actually want from the CHRO beyond functional HR delivery, are often implicit rather than explicit, and implicit mandates are notoriously difficult to deliver against. Part of the advisory work in the first ninety days is helping the CHRO surface and clarify that mandate, which sometimes requires a structured conversation with the CEO that the CHRO has been deferring.

The second structural challenge that consistently emerges is the quality of the CHRO’s own team, specifically the gap between the team’s current capability and what the CHRO’s strategic ambitions for the function require. CHROS WHO ARE AMBITIOUS FOR THE FUNCTION’S STRATEGIC CONTRIBUTION but who are investing their time in compensating for the team’s capability gaps rather than in developing the team’s capability are in a structural bind that will eventually constrain their own effectiveness. The first ninety days of the advisory relationship almost always surface this, and the advisory work that follows is often significantly about the CHRO’s own team: who to develop, who to move, what capability to bring in.

The CHRO advisory relationship compounds in value over time, because the advisor’s contextual knowledge of the organisation, the relationships, and the CHRO’s own decision-making patterns becomes more specific and more actionable with each conversation. The difference between a three-month engagement and a twelve-month engagement is not simply more conversations; it is a qualitatively different level of precision in the advisory input, because the advisor is not working from a general model of CHRO challenges but from a detailed understanding of this CHRO’s specific context and the specific decisions they have navigated together.

By the end of the first ninety days, the best advisory relationships have produced a clear shared understanding of the CHRO’s strategic priorities for the following twelve months, the two or three relationships that most need attention and why, the specific capability gaps in the HR team that need to be addressed, and the structural challenges in the CHRO’s own position that need to be navigated. They have also produced a working rhythm, a cadence and format for the advisory conversations that fits the CHRO’s working reality rather than a predetermined structure. And they have produced, in most cases, at least one conversation or decision that the CHRO reports as having gone significantly better for the advisory preparation that preceded it.

THAT SPECIFIC INSTANCE, the conversation that went better or the decision that was made with greater clarity, is the most reliable early indicator of advisory effectiveness. It is more informative than any formal evaluation, because it tells both the CHRO and the advisor that the relationship is operating at the right level of specificity, connected to real decisions and real stakes, rather than at the level of professional reflection that is valuable but not urgently necessary.