When your coach grows with you

Reflections on graduated coaching: how engaging with the same coach at different points in a career can result in mutual growth


In a classic coaching engagement, a coach works over a several-month period to support a high-potential leader as they shift into a role with increased scope and responsibility. In other cases, a coach may provide more urgent interventions focused on addressing short-term improvement opportunities holding back a talented professional. Support is provided, the engagement comes to a close, and both coach and client move on to new challenges.

However, this isn’t always the end of the story.  Some coaches and clients may come to work together again.  If the first engagement results in a trust-based relationship, a coach can end up working with the same client in several separate and sequential engagements over a substantial period of time, what I call “graduated” coaching.  As the client graduates by receiving formal recognition and promotion, the coach graduates the range and level of complexity of the coaching engagement to match the client’s expanded responsibilities and range of management control.

At the same time, the coach must graduate their approaches, raising their game to meet the more sophisticated development needs of their clients.  This can call for cultivating a deep understanding of client psychology, to explore the stories that clients tell about themselves and their organizations, and to gain perspective on the organization and team contexts which inform every decision, process, and outcome.  As coachee learns and evolves, so must the coach.

In my coaching practice, I spend about 50 percent of my time working with professional services firms.  These firms generally have a well-defined process for developing and promoting leaders.  Although the specific nomenclature varies, they typically are organized in Senior Manager, Rising Leader, and Senior Leader roles.  Over the course of a 2- to 5-year horizon I might work with a single client over three discrete graduated engagements, each calibrated to meet the demands of the leadership role the client occupies and customized to the specific strengths and development needs of the client.

Senior Manager coaching: driving performance

The context: I refer to this role as the “COO” of a professional services team that has been deployed on a client project.  My clients often consider this among their most satisfying roles because they have clear lanes of responsibility, sight lines on all aspects of the project, are the nerve center of the effort and so are managing up with senior client and team leadership, managing across with client and colleague peers, and managing down as the unquestioned “boss” of their team.  Everything flows through them and relies on them and so they can revel in the satisfaction of execution, organization, problem solving, client relationship building, team leadership.  They inherit a scope of work from their leaders and they work within those parameters to deliver the full impact of the opportunity.

The challenge: Senior Managers who I work with are generally experiencing struggles with: 1) working effectively with their leadership, with feedback often focused on an inability to provide clear top-down communications and sufficiently forward planning; 2) leading their teams effectively, by providing clearly defined “conditions of satisfaction”, working their teams to exhaustion by engaging in inefficient churn, or significantly underinvesting in people development.

Coaching approach: My coaching support for this role generally revolves around identifying one or more of those major categories and sub-categories, providing my clients with tools and concepts focused on communications and planning, execution, or people development, and then cultivating habits that will have a close-to-immediate positive impact on manager and team performance.  There is a strong reflective element to the coaching, but the goal is driving performance through execution, and so I prioritize a short Reflection, Ideation, Design, and Experiment cycle (a framework that I call RIDE), with a bias towards securing reps with learning.

Rising Leader coaching: ideation and definition

The context: If Senior Managers are the COOs of their projects, Rising Leaders are the CEO.  In this sense, their roles are much more tied to strategy than execution.  Rising Leaders are called upon to see the project from the proper elevation of leadership, enabling them to take in the big picture, and to project outward to the right horizon of leadership, often well beyond the sight lines of Senior Managers.  Rising Leaders stand in the future and bring their clients and colleagues along with them.  And they use the pattern recognition they have acquired over time to see around corners and to recognize opportunities and pitfalls that are far from obvious.

The challenge: When initiating a coaching engagement with a former Senior Manager who is now a Rising Leader, one starting point is to recognize that they now have to make sense of and manage more complexity and ambiguity than they did previously.  They are generally also more time constrained because they are often working on multiple projects simultaneously and therefore need to add value quickly and efficiently, and to develop the judgment of when to intervene and when to give their teams space to operate.

There’s a truism that leaders are promoted for how well they performed in their previous job rather than how well qualified they may be for their new job.  In a graduated coaching context, it’s important for me to remind my clients that what made them successful Senior Managers will not necessarily make them successful Rising Leaders, because the qualities and characteristics of Rising Leaders, though not totally incompatible with Senior Managers, are far from a perfect overlap.

Coaching approach: If in our first coaching engagement we were focused on ensuring daily and weekly execution, like slamming a set of doors down a hallway as each phase of the engagement is completed, my work with Rising Leaders is more about opening up new possibilities, both in terms of ideation and execution, cultivating a positive team gestalt, inspiring the team, pushing team and client thinking, and collaborating with Senior Leadership to contribute to the overall client service ecosystem.  I also spend a good deal of my time with these Rising Leaders, especially in their first year of a formal leadership role, helping them to define and design their personal strategy to achieve career fulfillment.

Senior Leader coaching: seeking wisdom

The context: If I’m reintroduced to a client I have worked with twice before, when I re-encounter them as a Senior Leader the requirements and patterns of leadership are scarcely recognizable compared to their previous roles.  Neither COO nor CEO of a single project, Senior Leaders are more akin to something like an Executive Chair, with both management and board responsibilities that translate, in their case, to managing and cultivating client relationships at the most senior levels, serving as a client counselor, and creating and nurturing the overall culture of the client service team, leading a set of Rising Leaders, and setting an overall leadership standard and direction for their organization at scale.

The challenge: If Senior Managers are focused on effective problem solving, and Rising Leaders are working to develop the judgment about when and where they engage their talents so as to add maximum value, Senior Leaders are generally seeking to operate in the domain of wisdom – which can take a variety of forms.

Coaching approach: In my experience, there is no adequate playbook for seeking to coach for wisdom. Coaches working in this rarefied domain must call upon their entire life experience – academic, intellectual, artistic, social, emotional, professional – and align that life experience with whatever path(s) their client may be pursuing, and possibly help their clients to discover paths they never imagined.

By the time one reaches this stage of coaching with a longtime client, something like genuine transformation from the original role and level of leadership becomes possible. Working with Senior Leaders in this way is in fact a process of co-discovery between coach and client and can be the most generative and satisfying form of coaching imaginable.


Daryl Ogden is the managing partner of Kenning Associates and a master coach.  Comments or questions? You can contact him here.