Download PDF
Engagement : Trust : Culture

Leadership Conversation Guide

Questions every executive search consultant should feel comfortable asking.

Beyond the Appointment

Executive search firms have always been trusted advisers during critical leadership decisions. Increasingly, however, clients are asking broader questions that sit alongside executive search.

  • Questions about leadership capability.
  • Succession.
  • Retention.
  • Burnout.
  • Team effectiveness.
  • Executive transition.
  • Employee engagement.
  • Psychological safety.
  • Organisational performance.

These conversations already exist. The challenge isn't recognising them...it's knowing how to explore them. This guide is not about selling leadership consulting. It simply helps consultants ask better questions. Questions that deepen client relationships. Questions that uncover organisational priorities. Questions that position the consultant as a broader strategic adviser. Some conversations may naturally lead to executive search.

Others may identify opportunities where leadership advisory can support the client. Either outcome strengthens the relationship

Understanding the Organisation

  • What are the three biggest people challenges your executive team is facing over the next 12 months?
  • Where do you believe leadership capability is helping–or constraining–the achievement of your strategy?
  • What concerns are keeping your executive team awake at night?
Guide to L&D +OD conversations

Leadership

  • How do you currently develop newly appointed leaders?
  • Do your executives receive structured coaching?
  • If so...How is success measured?
  • What support do leaders receive during their first 100 days?
  • How do you identify future leaders?
  • How confident are you in your succession pipeline?

Engagement

  • Do you measure employee engagement?
  • If yes...
    • annually?
    • quarterly?
    • pulse?
  • Who owns the engagement results?
  • What are the three biggest themes emerging from your engagement surveys?
  • Have engagement scores improved over the last three years?
  • How do your engagement results compare with your industry?
  • What actions changed because of the survey?

Wellbeing

  • Do you monitor EAP utilisation?
  • Are there trends emerging?
  • How do you measure burnout?
  • What does absenteeism tell you?
  • What is your average sick leave?
Guide to L&D +OD conversations

Attrition

  • What is annual voluntary attrition?
  • How does it compare with your industry?
  • Which groups leave most frequently?
    • graduates
    • women
    • leaders
    • technical specialists
    • new hires
  • What is your regrettable attrition?

Leadership Hygiene

  • Do leaders hold regular one-to-ones?
  • How often do they receive upward feedback?
  • How clear are role expectations?
  • How often are development plans reviewed?
  • Do leaders spend more time directing–or coaching?
  • How are difficult conversations handled?
  • How consistently are promotions assessed?

Psychological Safety

  • How comfortable do people feel challenging senior leaders?
  • Have you assessed psychological safety?
  • Are you familiar with ISO 45003?
  • How are psychosocial risks monitored?
  • Have psychosocial hazards appeared on your Board Risk Register?

Talent

  • Do you run formal talent reviews?
  • How do you identify key-person risk?
  • Which critical roles have no ready successor?
  • What percentage of senior appointments are internal?
  • Do you map future capability requirements?