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A Senior Director’s Coaching Journey

What do we know about a journey?

Imagine a journey you might take in an unfamiliar country – I remember such a journey in the countryside of Ireland many years ago. Something about those back roads of Ireland give you a sense of history and mystery – you can round a bend and be faced suddenly with an enormous castle centuries old, or drop into a pub where a bread roll is the size of an entire loaf at home. You can follow the stone walls that separate farms for miles and never have an accurate sense of where one farm ends and another begins.

The countryside of Ireland is not neat and tidy ---and the experience of “going where the road takes you” is exhilarating--- as long as you are available to experience it.

I think we know three things about any journey; one, a journey takes time – we seldom measure a journey in minutes;  two, a journey is unpredictable – at the start, we are seldom 100% sure of the outcome; and three, a journey is not linear – it can contain loops and concentric circles and be iterative in nature.

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I recently had the privilege of coaching a Bay Area senior IT Director who made the decision to take a journey of self development through executive coaching. Her coaching journey over 9 months contained the three elements above and I asked her to reflect and write about the experience so that others contemplating taking the coaching journey might have some sign-posts.

She initially began the journey focusing on 3 development areas called out by her CIO boss and supported by her recent 360 Feedback Report. Her focus began with an acceptance of and commitment to those 3 areas (strategic thinking, delegation and executive influence) while at the same time she questioned if these were the right areas of focus. Might there be a root cause under all 3 of these areas that wasn’t yet apparent?

As her coach, I saw her willingness and her hesitation/questioning – I felt it was a healthy stance when faced with a potentially very personal and protracted investment.

This senior director also had a couple goals for her journey in addition to developing in these three areas. They were: to have greater confidence in her direct reports and to be considered for promotion.

As with any journey, the unpredictability factor came into play along the way and at the end. While she came to understand strategic thinking at a much deeper level, the “root” included letting go and re-imagining her role as a leader. These we discussed many times in different ways. What was the payoff for letting go? How does one remind oneself to do it? How do you recognize when you’ve been seduced back into the weeds?

In the end, this senior director needed to “feel” it at a gut level --- needed to feel what it’s like to be “on my game” at a strategic level and to feel in control --- as well as what it’s like to move from the tactical to the strategic and still be authentic.

One of her victories at the end of the coaching engagement was when she took charge of a meeting with her rather assertive and vocal boss, and confidently presented the strategic direction for her organization. She felt herself being confident and congruent and I saw her shine with determination and courage. Her boss was visibly impressed. And by the way, she was exercising perfect executive influence.

It was at this point that we stopped talking about strategic thinking, and she embodied it.

Another learning that came through the coaching, in addition to those explicitly outlined in the beginning included a greater understanding of her boss’s style and approach. This freed up energy for this director so that she could respond more to the substance of her boss’s communications, vs. the delivery.

As she put it: My single most important learning was simply regaining confidence in myself and gaining insight into what was really important for me to feel successful. 

Also at the end of the engagement, she had plans in place to assess all of her direct reports and to increase the specificity of her expectations so that she could delegate more successfully, and with greater confidence.

She reported her learning around the key objectives this way: “… (an) important action, or perhaps inaction, is that I stopped rescuing my direct reports for things that are their responsibility. I provide leadership and guidance, but do not dive into the weeds to solve problems for them. This actually translates into another action, which is I now have the ability to spend more time thinking about leading the organization and what is important more holistically rather than being consumed by the tactical issues and the “day to day”.”

What advice would this senior director give to leaders contemplating a journey of executive coaching?

“First and foremost find a coach you “connect” with. Consider coaching a gift, not a “punishment” for not being perfect, and then embrace the opportunity and let your guard down. (not the easiest thing for me, but important in the process).”

Has she gotten that promotion yet?

The journey is not over – she has not yet been promoted but she is well on her way – it is clear that her commitment to learning through coaching is positioning her to achieve those goals --- it is just around the bend!

, San Jose Leadership Examiner

Rita Graziano is an executive coach, providing leadership coaching as well as career ddvocacy consultation to many organizations. She has coached hundreds of leaders and helped thousands of individuals to make the highest possible professional contribution while achieving true job satisfaction. ...

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