The First 90 Days with an Executive Coach

The initial 90 days of executive coaching establish the foundation for transformational leadership development. Three critical elements contribute to the success of the entire engagement: trust-building, strategic alignment, and early momentum.

Months 0-1: Building Trust

Every coaching relationship begins with uncertainty. Leaders often feel vulnerable sharing challenges with someone new, while coaches must quickly understand complex organizational dynamics and personal leadership styles. The first month for the coach is about creating trust and a safe container for honest dialogue, by:

• Establishing confidentiality as a mutual, non-negotiable commitment that protects both candid conversations and sensitive organizational information

• Creating psychological safety through consistent presence, genuine listening, and demonstrating that the coach understands the leader: his/her strengths and opportunities, what is important for the leader to achieve.

• Conducting discovery through structured conversations, stakeholder interviews, and assessment tools to understand context, strengths, and developmental opportunities

The Client's primary responsibilities are to show up to coaching with an open and honest mindset, including:

• Sharing openly and thoughtfully

• Following through on commitments between sessions to build mutual accountability

• Providing honest feedback on the coaching process

Months 1-2: Strategic Alignment

With initial trust and rapport established and deepening, the focus of coaching can shift to strategic clarity. This phase requires balancing the leader's personal development aspirations with organizational needs and stakeholder expectations. It includes moving from broad developmental themes to specific, actionable focus areas. For both coach and client, attention shifts to clarifying priorities:

Identify 2-3 key development areas with measurable leadership behaviors that can be observed and practiced in real workplace situations.

• Align with stakeholders (e.g., manager and/or HR partner) through structured conversations that respect confidentiality while ensuring organizational support and clarity of expectations

• Define success metrics and progress indicators that are meaningful to leader and organization

• Position managers as allies, creating a supportive ecosystem for the leader's growth journey

Months 2-3: Early Wins & Momentum

By month three, the coaching relationship has matured enough for deeper work, and leaders can begin experiencing the compound effect of consistent focus and practice. These aren't dramatic transformations but meaningful, smaller shifts in how they show up as leaders. At this stage, leaders can typically expect to experience:

1. Enhanced self-awareness in daily leadership situations, including recognizing patterns and triggers in real-time

2. Increased confidence navigating complex challenges, with new tools and perspectives for difficult conversations and decisions

3. More intentional decision-making and reflection, moving from reactive to responsive leadership

These early wins strengthen the client’s motivation and build confidence for tackling more complex developmental challenges. They also validate the investment to the organization and stakeholders.

The Importance of Cadence

Leadership development isn't a one-time event—it's a practice that requires consistent reinforcement. Regular sessions every 2-3 weeks maintain momentum through continuous cycles of experimentation, reflection, and refinement.

Conclusion

The first 90 days create a unique convergence of rapport, focus, and momentum. When trust, clear priorities, and consistent engagement align, they establish the conditions for sustained leadership transformation that extends far beyond the initial coaching engagement.

References

• Boyatzis, R. E., Smith, M., & Blaize, N. (2006). Developing Sustainable Leaders Through Coaching and Compassion. Academy of Management Learning & Education, 5(1), 8–24.

• de Haan, E., Duckworth, A., Birch, D., & Jones, C. (2016). Executive coaching outcome research: The contribution of common factors such as relationship, personality match, and self-efficacy. Consulting Psychology Journal: Practice and Research, 68(3), 189–207.

• Ericsson, K. A., Krampe, R. T., & Tesch-Römer, C. (1993). The role of deliberate practice in the acquisition of expert performance. Psychological Review, 100(3), 363–406.

• Grant, A. M. (2014). The efficacy of executive coaching in times of organisational change. Journal of Change Management, 14(2), 258–280.

• Luthans, F., & Peterson, S. J. (2003). 360-degree feedback with systematic coaching: Empirical analysis suggests a winning combination. Human Resource Management, 42(3), 243–256.