James, a country CEO, is rebuilding a brand's presence in a market it exited more than a decade ago. With no local team, no existing infrastructure and the need to build everything from scratch, he must create momentum while aligning sceptical stakeholders across the organisation. Priya has just been promoted to head of corporate marketing at a private-equity-backed company preparing to be acquired. She has just months to shape a compelling transformation agenda for the future owner while establishing herself in a more strategic leadership role. 

These situations aren’t hypothetical. James and Priya (names have been changed for confidentiality) are two of the senior leaders who attended a recent INSEAD alumni pilot offering mentoring to executives leading a change mission. Over a six-month period, 25 pairs of experienced alumni mentors from the Executive Master in Change programme were matched with Global Executive MBA mentees facing major change.

Participants like James and Priya shared a common thread: none of them required someone to tell them what to do. What they needed was someone who could explore complex challenges with them without prematurely jumping to overly simplified solutions. This called for a rethinking of what mentoring can offer and shaped the central design approach of this global initiative.

Why traditional mentoring models break down

Research on why workplace mentoring programmes underdeliver points to a familiar set of causes: limited communication about who can access them, narrow eligibility often reserved for early-career or rising high-potential employees, and mentors too stretched to engage meaningfully.

Although mentoring is common in the early career stages, isolation becomes the norm as people move up the ladder. At the pinnacle, few CEOs report having a peer group who can offer support in vulnerable moments. Most leaders are going it alone and carrying more with a shorter runway.

In 2025, CEO turnovers hit a record high with 234 departures globally (up 16%), while average tenure fell to 7.1 years, down from 8.3 in 2021. A study of 109 CEOs from major Canadian organisations revealed that their loneliness didn't arise from a lack of contacts; it came from not trusting their board or seniors. This data points to a paradox: the higher leaders rise, the less opportunities they have for reflection.

Like James and Priya, most leaders aren’t short of expertise. What they often lack is the space to reflect: intentional time, and the permission and trained support to help them think out loud about a problem before they act. It’s a gap that many mentees themselves don’t realise at first, as they show up hoping their mentor will simply tell them what’s worked for them in the past, or affirm what their AI tools have already “advised” them to do. Neither fully addresses what’s actually going on beneath the surface of a difficult change: the anxiety of not yet knowing the nature of the challenge and its possible solutions, while feeling the pressure to look like you do.

Containment, not control

In this pilot, we framed mentoring less as a vehicle for guidance and more as a space for containment and co-thinking. In this context, containment means to hold and transform the raw anxieties and emotional distress of change into something safe and manageable. The aim wasn’t to provide answers but to create a reflective partnership in which leaders could think more expansively, creatively and clearly about the challenges they faced in the process of change.

This may explain why mentoring is becoming more – not less – relevant in an era of AI. Information, frameworks and expert advice have never been easier to access. What’s scarce is a trusted relationship where a leader can confidentially and actively think through the nuanced complexity of their situation. That’s the principle at the core of the pilot's design: The mentor's job isn’t to resolve the mentee's uncertainty, but to help contain it and to support them as they think through their challenges – as a steady, non-judgemental presence who shares their experiences and pitfalls – while the mentee works out their next move on their own.

One mentee shared: “[It was] helpful to have an independent senior professional to talk to who understands my context but is not too close to it as to be biased. This allowed me to be frank and [for] my mentor to be candid in his feedback.”

On the part of mentors, they need to resist familiar traps like the instinct to reassure, to offer solutions too quickly or to demonstrate expertise. These well-intentioned interventions could end up shutting out the very reflective space the mentoring relationship is designed to create.

Designing mentoring for reflection

Containment creates the conditions for leaders to reflect: the time, safety and distance to examine doubt, frustration and competing interpretations before turning them into decisions. Rather than treating uncertainty as a problem to be solved through advice, the pilot treated it as something to be explored before taking action. This reoriented familiar mentoring practices – experience-sharing, challenge and support – towards the needs of senior executives leading complex change.

Creating this space requires more than basic registration and matching. The programme was designed to support mentors in the relational work of mentoring, including listening before advising, asking before telling and helping mentees separate what they knew from what they feared, assumed or had not yet understood. Mentors could still share experience and offer candid feedback, but not before the mentee had the opportunity to make sense of the situation on their own terms.

The support infrastructure began with recruitment and onboarding and continued through regular check-ins, peer supervision and one-to-one support from the programme directors when difficult situations arose. These mechanisms helped mentors reflect on their own responses – including the fear of being judged, pressure to meet unrealistic expectations and doubts about their performance – to keep in check their reflexes of responding by reassuring, advising or taking over.

This matters because containment isn’t simply a quality that one person provides to another; it’s a condition created between people. It depends on trust, attention, boundaries and sufficient structure to make candour possible, combined with enough flexibility to work with each mentee’s changing goals and circumstances.

Transparency about the programme’s objectives helped the pairs establish reciprocal relationships quickly. Within that framework, each pair could negotiate how to approach the relationship as new challenges emerged over time. The result was not a standardised mentoring conversation, but a consistent set of conditions under which leaders could think more expansively, creatively and clearly.

Designing effective mentoring programmes, especially at senior levels, is less about optimising structure than about protecting the conditions that enable reflection. Organisations investing in mentoring at scale keep reaching for the same fix: better matching algorithms, tighter metrics and more oversight. Although technology may keep getting better at giving quick answers, it’s no replacement for sitting with someone while they work out what they actually think. This pilot suggests real value was never in the technical machinery; it’s in the relational and psychological space mentoring is meant to provide – which can get crowded out too easily.