When organizations invest in coaching on behalf of their leaders, the outcomes are relatively more defined – in that there is usually a business impact that they are hoping out of it. At the beginning of the coaching engagement, significant time goes into stakeholder alignment, establishing agreements, and having the leader fully onboard in a way that is meaningful to them while also realizing the hopes of their sponsors.
When I am speaking with the sponsors, this includes confidentiality, key outcomes, budgets, indicators of positive movement, check-ins etc. When I speak to the leader, I focus on the leader’s sense of autonomy in entering the coaching relationship, and their integrity in how they show up inside the relationship. Because the sponsorship is coming from the organization’s budgets, it removes any financial discomfort with the investment, and the leader is able to focus on the coaching itself.
When a leader chooses to invest out of their own pocket, the stakes can feel different to them. They are investing in their own evolution, perhaps with abstract hopes for their future, and meaningful yet sometimes vague motivations. So in the initial conversations, they are considering the coaching relationship both as a sponsor and as the coachee. These are different frames to look from, and fears around making significant financial investments often surface and collide with desires for a different future.
As someone who has invested in my own coaches over the years, and having committed financial sums that were far beyond my comfort zone, I have an appreciation for what this feels like. Because I understand the weight of this commitment, I deliberately slow down the initial conversations and allow enough space for their true desires to unfold.
Sometimes, there is a bit of coaching involved before we decide if it is a good idea for us to commit to a coaching relationship. These dialogues become a testing ground where I am looking for specific patterns to determine if they are ready for the kind of transformative work I offer.
I look for patterns of thinking that suggest they have a baseline of self-awareness, reflective capacity, openness of mind, and the psychological maturity to understand things deeply in their essence.
This is as opposed to patterns of thinking that suggest that they are wanting shortcuts and quick fixes, or are completely looking to me to be their savior.
I’ve also noticed that I work best with leaders who are successful on paper. This is because they have generally applied themselves with enough rigor and intellectual depth for them to enjoy the success they did, at whatever level is meaningful to them. They also usually tend to be in positions of responsibility and power, though not necessarily.
So these initial conversations become a sort of testing ground for fit, where I am filtering for clients that I can make the biggest difference with. As a result of this, the vast majority of leaders I work with tend to be navigating the apparent duality of wanting material results while also wanting meditativeness, peace of mind and other more abstract qualities. They are also usually afraid that if they pick one fully, they will have to give up on the other.
These are the leaders I describe as navigating the frontier between inner stillness and outer impact. Here, part of our work becomes exploring the non-duality between the material and the so-called spiritual world, and understanding how these are two sides of the same coin. We inquire into their identity, their relationship to the systems they operate in, explore the base line quality of life experience that they would love to have, and the material desires they want to create alongside. We open the possibility that these are simultaneously coexisting realities, and champion their ability to experience this for themselves.
In this way, we ensure that they are not holding their sense of wellbeing hostage to their material results, which paradoxically allows them to achieve their material results with far less friction. Creating these results becomes enjoyable rather than effortful, because they are now creating from a different space – of aliveness and inspired energy- rather than from a sense of lack and desperation.
With leaders who are their own sponsors, this allows them to release any discomfort around the investment. With leaders who are being sponsored by their organization, this opens up the possibility of bringing their whole self and life to the coaching relationship, without losing perspective and fixating on the organizational goals to an unhelpful degree.
