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Reflections on Leadership | Reflections on Coaching | Reflections on Strategy

Executive Coaching:
​Key Lessons Learned

Reflections on Coaching
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From my perspective, one of the most interesting engagements is the opportunity to coach a senior executive in an organisation. This is because it plays to one of my core beliefs which is that a leader is in a very privileged position by virtue of the impact he/she has on the lives of the people he/she leads and manages day in day out. As a coach, I am always grateful for the opportunity to make a contribution, no matter how small. In this short article, I aim to share three key lessons learned through successfully coaching a number of executives over the last twenty years.

Lesson Learned 1:
Remember that every coaching engagement is unique

It sounds like I am stating the obvious but it is easy to fall in the trap of ‘deja vu’!

Two executives may have, what appears at first, similar developmental goals but, if they are from two different organisations, you can bet that their respective developmental goals will shape up to be different.

It is therefore imperative that the coach stays open-minded throughout the whole coaching engagement and listens carefully about what is being said (or not!) about the broader organisational context.

Lesson Learned 2:
Focus primarily on the executive’s strengths

Most coaching engagements have one or more sponsors. In my experience, there is often pressure exerted on the coach by the sponsors, at times in a very subtle way, to focus on the executive’s areas for improvement or weaknesses as part of his/her development goals for the coaching engagement.

What I have found over the years is that focusing on the executive strengths is by far more effective and rewarding for the partnership between the executive and the coach for the following reasons:
  1. It breaks down defense mechanisms. Who likes to talk about one’s weaknesses or so-called areas for improvement? It is not great for one’s self-esteem and most people will try to avoid the subject anyway by building some kind of facade and/or justify their behaviours.
  2. Most weaknesses can actually be traced back to a strength which is being overdone. To illustrate this important point, I would like to share with you a real-life experience. I was once coached on my lack of delegation and tendency to micro-manage my team members. Interestingly, I have an eye for the details and am a perfectionist. I will look at a report and immediately will spot the typos, the omissions, the flaws and anything else which needs correcting way before anybody else. I would argue that this is a strength of mine. But what if I overdo this strength? Most likely, I will end up losing sight of the big picture while being caught up in the details, frustrating people around me by being overtly critical, micromanaging them or failing to delegate altogether - which is exactly what happened to me in the end. It was more rewarding when my coach focused on how I could leverage this strength of mine in a much more constructive way in the team as opposed to focusing on how I could learn to delegate. It is important to remember that leaders are not expected to be perfect; so if one decides to coach on weaknesses after all, then my suggestion is to engage in a conversation about what is the executive’s ‘acceptable weakness’!

Lesson Learned 3:
Aim to ask insightful questions to both the executive and his/her ‘eco-system’

In addition to the scheduled coaching sessions between the executive and his/her coach, most coaching engagements often start with an interview of the executive’s ‘eco-system i.e. the different stakeholders such as the executive’s manager, direct reports, peers...These interviews are critical to the success of the coaching engagement as they provide valuable insights into the executive’s developmental needs; therefore it is absolutely essential that the coach gets them right by asking insightful questions. Easily said but extremely difficult in practice! The three types of questions to ask are:
  1. Situation Questions e.g What? Who? When? Where? How?...These questions bring out factual answers. Although important to set the context for the coach, they have limited benefits for the coachee/interviewee as he/she is basically expressing facts that are already known to him/her.
  2. Motivation Questions e.g Why? What is the reason for...? These questions help engage the coachee/interviewee on a more personal level as they will reveal his/her values and belief systems and the motivation behind the facts. Also, they potentially start making the coachee/interviewee think about his/her answers and in that sense are relatively more insightful.
  3. Implication Questions e,g What if...? What is the best option of...? These questions can prove difficult to ask (for the coach) and to answer (for the coachee/interviewee). They help both explore the different options, barriers (to change) and move the conversation to the solution space which is much more positive in itself. These can be potentially very insightful and of benefit to both the coach and the coachee/interviewee.

It is essential to be perceived as a ‘trusted advisor’ during the whole coaching engagement; remembering these three lessons will undoubtedly contribute to this perception.

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