The Leadership Coaching Dilemma: Contextual Coaching Is the Answer

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In January 2013, a new Chief Talent Officer took his Senior Leadership Team seat at a Fortune 100 Manhattan-based international financial services firm.

Before the chair was warm he had cancelled every one of the firm’s dozens of leadership coaching engagements taking place around the world. Such a sweeping, immediate, and disruptive gesture smacks of support from the CEO (if it wasn’t the CEO’s idea to begin with).

You can imagine the conversation:

Any organizational benefit as a result?

CEO: “Is all of this leadership coaching improving anything? We’re paying a fortune.”

CTO: “Let me check and get back to you.”

An hour later, after the new CTO had asked a few critical questions of the HR, L&D, and OD people who had been managing leadership coaching for the firm, he poked his head in the CEO’s door.

CTO: “I’m told the majority of people receiving coaching are apparently enjoying it.”

CEO:Is the organization deriving any enterprise-wide benefit?”

CTO: “There is no process or platform in place to track it or consolidate the data.”

CEO: “Then let’s put a stop to it until we can approach this investment strategically.”

CTO: “Done.”

Leadership coaching: the tail wagging the dog

This oversimplified scenario is not far from a verbatim record of how the conversation might have gone moments before the plug got pulled earlier this year.

It seems that leadership coaching, which has blossomed in popularity over the past decade, has somehow become the tail that is wagging the dog. Many organizations have been subsidizing leadership coaching engagements with no platform, systemic structure for identifying and capturing enterprise-wide trends and patterns, nor anyone responsible for analyzing and reporting to upper management on key strategic themes or metrics.

Leadership coaching might be delivering huge returns for the beaucoup dollars being invested. But, who can tell?

Coaching, as it is customarily practiced, usually takes place behind a veil of secrecy or on a desert island where what is revealed under the palm tree remains forever buried beneath the palm tree.

One thing is sure: if there is no way to establish a contextual framework for the leadership coaching — systematically and strategically capturing the abundance of organizational data disclosed in the coaching process — enormously valuable information is being washed down the gutter, blown away in the breeze, or shredded.

Contextual coaching is the answer

Is it any wonder that coaching engagements are beginning to be second-guessed by senior leadership? In a field dominated by life coaches who rarely held executive positions, and former HR executives who never saw a P&L statement, it’s not surprising that the voice of the organization too often gets lost as the coach and coaching client enter a cone of silence to conduct their mysterious business.

Great coaching might be taking place and leaders might be experiencing breakthroughs of one sort or another in such isolation, but how can one tell? Moreover, who is ensuring consistency and continuity in coaching across the organization?

Enter Contextual Coaching, or coaching in the context of the organization if you prefer. The keys to aligning what individuals do best with what their organizations need most are simple:

  • The individual being coached and the organization are co-clients. The voices of each must be represented if the engagement is to add value to both.
  • A coaching coalition must be formed from Day One that includes the coach, the individual being coached, the manager of the individual being coached, and the sponsor of the coaching engagement (typically from HR, L&D, or OD).
  • The patterns and trends that emerge as multiple coaching engagements take place across the organization need to be captured, analyzed, and reported without compromising individual engagement confidentiality.

The relationship is the true client

Like marriage and family therapy, the individual being coached and the organization paying for the coaching engagement are not the true clients; the relationship between them is the client. Without the voice of the organization being kept alive and well in the engagement, the whole process, such as it is, can easily, and often does, become all about the individual.

Yet, the individual being coached will be declared successful or not successful only in the context of the organization. The coaching engagement will lose most, if not all, of its power and meaning, if the voice of the organization is muted, lost, or never accounted for.

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Coaches should never be surrogate managers. The coaching coalition is a critical alliance between the coach, the manager of the individual being coached, the individual being coached, and the corporate sponsor of the coaching engagement. The latter three people need to take over after the coach is gone.

To ensure sustainability of the positive outcomes from coaching, managers of the individuals being coached and their HR, L&D, and/or OD partners need to learn how to best support the behavior change that takes place during the engagement. In a Contextual Coaching process, the entire coalition learns from the engagement and is better prepared to sustain it as a result.

A question of the right balance

Coaching reports must be set up in such a way that the presenting issues that give rise to the coaching needs are balanced by a consistent and structured assessment of how aware and effective the individual being coached is regarding the organization’s strategy, structure, communications style, culture, and other critical expectations that define the organization and its Talent Strategy.

Leadership coaching reports must be seamless regardless of where on the planet the engagement takes place and they must capture and chronicle growth opportunities for the individual leader as well as the organization as a whole. One without the other is money left on the table.

CTO: “Without an architectural rendering of this organization’s strategic agenda to work from, leadership coaching engagements are like watching the construction of a skyscraper through a knot hole in the plywood construction fence.”

CEO: “Agreed. A myopic view of an organization the size of ours not only has limited value, it can be dangerously misleading. When you can show me how we can align all of the leadership coaching engagements with the strategic direction of our business, I’ll be all in for coaching our leaders. Until then, No context — no coaching.”

  • Edmund_Jones

    Leadership is one of the vital part of an organization and there are many people those who want to perform well in their organization so it is better that we carry on the coaching of the particular event. So it is better that leadership coaching is highly vital for the people that first they need to is the contextual leadership coaching.

  • Alagappan

    Really enjoyed reading this article. Provided real context for coaching executives and future leaders in organizations. I will be buying your book ‘coaching connections’. Do you have a coaching blog that you write on regularly. I would be happy to be on your mailing list. My email id is ‘’. Thanks