The Coaching Engagement Is Often Won or Lost Before the First Session

The fate of most executive coaching engagements is determined not in the coaching room, but in the weeks before the coach and coachee meet for the first time. This is not a comfortable observation for those who have invested heavily in coach selection, coachee readiness programmes, and sophisticated 360 instruments. But the evidence, accumulated across thousands of coaching engagements in organisations of every size and sector, points consistently in one direction: THE CONTRACTING PHASE IS WHERE COACHING MOST CONSISTENTLY FAILS, and the failure is rarely recognised as such until the engagement is already in difficulty.

What inadequate contracting looks like is familiar to anyone who has worked inside large organisations. The HR Business Partner recommends a coach. The sponsor, typically the coachee’s direct manager or a senior HR leader, approves the engagement and provides a brief, often verbal, description of what they are hoping the coaching will address. The coach meets the coachee, they agree on a development theme or two, and the sessions begin. Six months later, the HR Business Partner asks the coachee whether they found the coaching useful. The coachee says yes. The sponsor is not formally consulted. No one has verified whether the stakeholder experience of the leader has changed. The engagement is recorded as successful, and the pattern repeats.

The problem is not that any of the individual steps in this sequence are wrong. The problem is that the three conversations that must happen before a coaching engagement can work have not happened at all. These are the sponsor conversation, the leader’s reframing conversation, and the goal architecture conversation. Each is distinct in purpose and requires a different quality of attention. None can be adequately substituted by an intake form or a development plan template.

The sponsor conversation is the most consistently underinvested conversation in executive coaching, and its absence creates problems that no amount of skilled coaching can fully correct. The sponsor, whether a direct manager, HR leader, or member of the executive committee, has a specific set of expectations about what the coaching is for and what it will produce. Those expectations are not always aligned with what coaching can actually deliver. When the misalignment is not surfaced and resolved before the engagement begins, it becomes a slow-burning source of disappointment and, eventually, of wasted investment.

What sponsors typically want from coaching is behavioural change that is observable, specific, and relatively rapid. They want the leader to “be more collaborative with the cross-functional teams,” to “speak up more decisively in the executive committee,” to “manage the team without the micromanagement that is creating turnover.” These are legitimate expectations. What they often do not account for is the timeline of genuine behavioural change, the conditions under which that change is most likely to occur, and the active role that the sponsor themselves must play in creating those conditions.

A productive sponsor conversation clarifies three things. First, it establishes the specific behavioural outcomes the sponsor expects, described in observable, stakeholder-perceptible terms. Second, it establishes what the sponsor will do differently to support the leader’s development, because coaching conducted in an unsupportive or actively undermining environment is structurally constrained. Third, it establishes the accountability architecture: how progress will be measured, by whom, and at what intervals. A sponsor who is not willing to participate in a mid-point review and an end-of-engagement assessment has not, in any meaningful sense, sponsored the coaching. They have merely approved a budget line.

In Indian organisations, the sponsor conversation is particularly challenging because of the cultural dynamics around hierarchy and the assumption that development is the responsibility of the individual being developed. Senior leaders who commission coaching for their direct reports sometimes regard the idea that they themselves have a role to play in supporting that development as an unwelcome additional burden. The conversation that reframes the sponsor’s role from approver to active stakeholder is not always comfortable. It is, however, essential to the quality of the outcome.

The second conversation that must happen before coaching can work is the conversation with the leader being coached about the nature and purpose of the engagement. This conversation is particularly critical, and particularly often neglected, in cases where coaching has been commissioned in response to a performance concern or a significant piece of developmental feedback. In these cases, the leader may receive the communication that coaching has been arranged for them as something between an instruction and a warning. The coaching is, at least in their experience, mandatory rather than voluntary. And mandatory coaching, as the research consistently demonstrates, produces significantly worse outcomes than coaching that is genuinely sought.

The dynamics of mandatory coaching are predictable and worth understanding clearly. The coachee arrives at the first session with a complex internal orientation: part of them wants to demonstrate that they are cooperative and open to development, because they understand that their continued career progress may be associated with a positive outcome from the coaching. Another part of them is defensive, because the implicit message behind mandatory coaching is that something about them is not good enough. A third part is strategic, working out what the coach will report back to the sponsor and calibrating their disclosure accordingly. None of these orientations is conducive to the kind of honest, vulnerable engagement that genuine coaching requires.

The leader’s reframing conversation is the conversation that addresses these dynamics directly, before the first coaching session, by establishing a different frame for the engagement entirely. The frame is not “you have been sent to coaching because there is something wrong with you.” The frame is “you are being given access to a confidential, high-quality developmental resource at a stage in your career when the complexity of what you are navigating genuinely warrants it.” This is not a manipulation of the truth. For senior leaders in complex organisations, it is the truth. The reframing conversation makes that truth visible and accessible, and it changes the quality of engagement from the first session.

The third pre-engagement conversation that most coaching programmes skip or handle inadequately is the goal architecture conversation: the structured dialogue about what the coaching is actually trying to produce, for whom, and how that will be measured. This conversation is complicated by the fact that the language organisations typically bring to goal-setting, the language of SMART goals and key performance indicators, is often poorly suited to the nature of developmental coaching goals.

Behavioural and developmental goals are not always easily quantifiable. “Being more strategic in the room” is not a SMART goal. Neither is “developing greater executive presence,” “building more authentic stakeholder relationships,” or “leading through influence rather than authority.” These are genuine and important developmental outcomes, and they resist the kind of precise measurement that organisations comfortable with KPI frameworks find reassuring. The temptation, when the SMART framework is applied to coaching goals, is to convert these genuine developmental outcomes into proxy goals that are measurable but not meaningful, or meaningful but not measurable.

A productive goal architecture conversation for executive coaching works differently. It begins with the stakeholder experience: what specific behaviours, if they changed, would most meaningfully improve the stakeholder’s experience of the leader? It then identifies the conditions under which those behaviours would most valuably manifest, because behavioural change that does not transfer to the relevant professional contexts is not, in any organisational sense, change at all. Finally, it establishes a measurement approach that is anchored in stakeholder observation rather than self-report, and that will be applied at specific points in the engagement rather than left to an end-of-programme survey.

The goal architecture conversation also surfaces, early, the tension that sometimes exists between the developmental goals the leader cares about and the organisational goals the sponsor has defined. This tension is not always resolvable, and when it is not, it is better to know that before the coaching begins than to discover it six months in, when both the coach and the coachee have invested significant time and trust in a set of conversations that the sponsor regards as peripheral to what they commissioned.

RK

Founder & Principal Consultant, ProventusHR

RK holds the Master Certified Coach (MCC) credential from the ICF and is a Certified Practitioner of the Marshall Goldsmith Stakeholder Centred Coaching methodology. He has facilitated over 400 leadership, culture, and coaching programmes across India’s most complex organisations.

About the Author

Rama Krishna (RK)

Founder Director, ProventusHR  ·  MGSCC Master Coach  ·  NDA Alumnus

Founder of ProventusHR and principal architect of ExperienceLearning and REEL|Life. 25+ years across leadership advisory, executive coaching, and experiential design across 14 industries. 9x Brandon Hall HCM Excellence Award winner (2022 to 2025).

Full Profile ›