Executive Coaching with a Retiree

“Everyone needs a coach. It doesn’t matter whether you’re a basketball player, a tennis player, a gymnast or a bridge player. We all need people who give us feedback. That’s how we improve.”

— Bill Gates

Following up on my previous post about “Work in Retirement,” I have been asked by other peers about what’s involved in my executive coaching gigs in retirement. I’ll dedicate this post to one of the ways I like to do these engagements, which is when done in conjunction with 360° interview-based assessments. Even though the specific nature of each engagement is private, there aren’t any real secrets to this methodology. If people are interested, I can also follow up this “getting started” post with more detail.

Why use a retiree as an executive coach?

I have found that pairing a retired executive like me with an operating executive in a coaching relationship can be a “win-win”  for both sides:

• For the retiree, it provides an opportunity to remain engaged with less day-to-day commitment and a potentially meaningful sense of legacy to pass wisdom to the next generation of leaders.

• For the operating executive, it provides objective and unbiased perspectives from someone with a deep understanding of business dynamics and strategy, outside the day-to-day operations of the business.

Personally, I’ve found the best coaching relationships occur when a company decides to support an executive in their coaching needs, in contrast to an executive hiring a coach personally. Company sponsorship can demonstrate the buy-in to reach out to other functions to build a 360° assessment of the executive, and I believe there are a number of other cultural benefits.

What does a first engagement look like?

I have personally found that it’s hard for people to work on too many areas of improvement at the same time in almost any discipline. 

While many haven’t been in an executive coaching program before, roughly 3 out of 4 people in the United States have taken some form of public speaking class. I personally did this in junior high, and I was even on the debate team in high school. I also took follow-on courses as a professional, including the famous Decker Communications and Duarte programs. I still know the things about public speaking that I need to improve on:  too many filler words, speaking too fast, excessive gestures, visual aids that are too busy, looking at my visual aids and not the audience, etc., but in each of these courses, the best thing I’ve been advised to do is focus on one or maybe two areas at a time. The same can be said for executive coaching.

So, how does one pick the right one or two things to work on in an initial development plan for an executive?

Sometimes, the executive has these one or two things in mind, and in some cases, I have done engagements where I just meet with the executive on a regular basis (e.g., weekly or biweekly) and base a development plan on what we discuss.

However, as mentioned above, I have personally found the best way to start is an interview-based 360° assessment.

What is a 360° assessment?

In this context, the assessment involves collecting feedback on the executive from their manager, peers, subordinates, and often subordinates of peers. The intention is to get a comprehensive view of strengths and weaknesses by gathering feedback from a holistic perspective.

While many coaching programs utilize a multiple-choice survey method, allowing for quantitative measurement and benchmarking, I have personally found that the interview approach provides a richer view of the executive and their role in the company, often with specific stories or anecdotes that can help not only provide a richer understanding but also a way to communicate more concretely both performance and development areas. The downside is that this takes time, but I’ve personally found that this investment is worth it.

In general, when I conduct interviews, I let interviewees know that I don’t share specific comments with the executive and that I only relay stories when the same feedback is provided by multiple interviewees. The executive’s most blatant blindspots always come through from multiple angles. To illustrate this, I explain to interviewees the Johari window.

What is the Johari window?

The Johari window illustrates that people’s blindspots are generally known to everyone except the person themselves. Given that a development program will focus on one or two areas, generally, the selected areas of improvement will be ones that are the most commonly reported!

Like many great frameworks, the Johari window is a 2x2 matrix. On one axis is what you know and on the other axis is what everyone else knows. Here’s the summary:

• What you know and what everyone else knows → Public

• What you know and what no one else knows → Private

• What you don’t know and what no one else knows → The Unknowable

• What you don’t know and what everyone else knows → Your blindspots

I have found that the best place for the executive to start their development is on their blind spots.

Why?

• Everyone else already knows the blindspots and can generally provide very specific examples of areas or situations that illustrate a need for improvement.

• The executive can build better self-awareness of how their actions, decisions, and behaviors impact others. This self-awareness can be helpful both professionally and personally.

• The executive disclosing to others what they’re working on in their coaching program will not be a surprise to others, and it creates accountability.

• It is relatively straight-forward for both the executive and the coach to check-in with interviewees on progress toward improvements after-the-fact to demonstrate to others that the executive is (or is not) taking the development program seriously.

I have also found that in addition to providing development opportunities for the executive, running this type of process demonstrates to other employees a culture of openness, professional development, better team dynamics, and continuous improvement.

Topics for interviewees

I personally like to have free-flowing conversations with interviewees, but I also keep a checklist of ground to cover. My basic outline, which I customize for each assignment, looks like this:

Setting the stage:

• Introduce myself

• Purpose of coaching assignment and assessment

• Confidentiality of individual comments

• Explanation of Johari window

The “meat” of the discussion:

• How you work together.

• Executive strengths and contributions.  Examples.

• Areas of improvement. Specific skills or behaviors that would enhance effectiveness.

• Leadership style.

• How the executive handles conflict.

• Communication with the team. How it could be improved.

• Team dynamics. Nature of executive contribution. Feedback and adaptability. Examples.

• Vision and strategy. Areas of improvement.

• Impact to organization.

• Potential for future growth and development.

With each interviewee, I keep detailed notes, which I keep private. I compile comments later and anonymize them to general themes, and then share with the executive to form the candidates for a development plan.

The Initial Development Plan

Once the themes are established, I work with the executive on one or two areas of improvement to drill into, with specific objectives and timelines. One objective is for the executive to communicate with others regarding what they are working on and some of their next steps to create accountability. We then work through regular meetings on proofpoints to demonstrate progress against those objectives. In general, executives are encouraged to seek feedback on their own progress with their peers, subordinates, and their boss. This is something that I, as a coach, like to do as well, albeit on a less frequent basis.

Most Common Themes

While each coaching assignment is private, here are some themes that have come through in my coaching experiences when using the 360° assessments and going deeper than the typical weekly 1-on-1 formats:

• Communication. Sometimes, executives need to talk less and listen more. In other cases, they need to talk more and be more present with their teams. Executives need to strike the right balance. As a coach, I’ve found that I can help solicit the feedback from others and also observe from the sidelines in company or group meetings. In modern work environments, Zoom and recorded conferences make it much easier for coaches to observe behaviors without affecting the systems.

• Empathy. Often, executives don’t know the impact that their actions, decisions, or behaviors have on others. I’ve found I’ve been able to raise awareness among executives with concrete storytelling based on the 360° interviews of verbal or nonverbal cues they give to their teams. Just having this awareness can go a long way toward executives improving relationships with others.

• Leadership and team-building. One real challenge is that executives often get to where they are because of their competence and not their leadership of others. Focusing on taking the steps to make the team work well can go a long way toward performance beyond help with competently competing specific tasks. I’ve been able, as a coach, to partner with executives to remind them to seek opportunities to enhance leadership and team building.

• Strategic thinking. It’s often easy for leaders to get caught up in the tactics alongside their teams, and many executive teams focus on delivering each other “read outs” of their execution to date. While everyone on their teams may be working hard, it’s typically up to the leader to be able to step back and take hard looks at the strategy. Sometimes, having an outside coach with a lot of other experiences can help create the space for executives to step back and think strategically.

• Coaching and developing others. Executives often need to balance the desire to “snow plow” for team members to remove obstacles versus coaching to enable their people to do it on their own. There’s a delicate balance here, as people can feel a great sense of accomplishment from overcoming obstacles knowing they have support, rather than feeling either abandoned by their leader or feeling that their leader is overpowering. This is a delicate balance, and I’ve found that a coach can sometimes help executives strike that balance. 

• Navigating ambiguity. When there’s ambiguity, leaders can unwittingly be seen as “flip flopping” or unable to provide direction. As a coach, I’ve provided different kinds of advice, including ways to communicate uncertainty, openness to ideas, as well as the need to often commit to a direction, even when uncertain, for some chance to learn more.

These are just a few examples, but I have found that executives have appreciated the work we do together.

Want to learn more?

Part of what I enjoy about being retired is having the time to reconnect with old colleagues and to discuss their issues. Feel free to reach out if you’re interested in doing executive coaching, using an executive coach (even if not me!), or perhaps even in improving your use of an existing executive coach. I’d be happy to talk through any of my experiences, or any of yours, as I’d love to learn more myself!

Feel free to message me!