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The Psychology of Executive Coaching

June 23, 2021

Barry Stern

in BLOG

How companies can think strategically about the psychology of executive coaching, and leverage it for better business results.


There’s one thing executives tell us they are craving to help them develop: external coaching. In this year’s Global Leadership Forecast, it topped the list as the number one request from leaders to help them get better at their jobs. While not a panacea, an external coach with a unique unbiased perspective, armed with the right tools and techniques, can make a dramatic difference in performance. By understanding key aspects of the psychology of executive coaching, you and your executive team can get the most out of an external coaching relationship.

Personally, most of my 35-year career has been in a leadership role and much at the executive level. Along the way, I’ve also been an executive coach and been coached myself. This multifaceted perspective has left me with some lessons to share about executive coaching.

In this blog, I’ll also explain my personal psychology of executive coaching and discuss my thoughts on what great executive coaching looks like, why it works, and why we need it. Additionally, I’ll reflect on what I’ve learned from the many executives I’ve had the pleasure of coaching.


Defining Executive Coaching

I’m often surprised by how people think of executive coaching. Historically, I’ve found that some think of it as a last-ditch effort to rescue a failing executive. Although turnarounds are possible, more often the coach in such a situation is being introduced too late in the game. Habits and relationships have too often calcified over many years, and the likelihood of success is much lower.

Nowadays, many enlightened HR colleagues recognize that earlier is better. For example, calling in an executive coach before a large career step occurs, before a business needs to be turned around, or when a huge internal restructuring has changed the game. On the flip side, some executives think of it more as a therapy or a more general life coaching session (which it’s definitely not!).

So let’s be clear about how we define executive coaching at DDI: At heart, executive coaching is a partnership designed to deliver thought-provoking insight, feedback, and suggestions that help executives perform at their peak potential. The end goal? To help executives drive positive shifts in their performance, derive more satisfaction and personal development from their work, and drive business results.


How an Executive Coach Helps

At these high levels, executives frequently find themselves surprisingly exposed and vulnerable. Many times they have gotten to where they are primarily because of their technical expertise. And while they have learned to rely less on that as they have progressed through the ranks, the cracks in their development are amplified because of their visibility and implications.

For many new executives, they are now in charge of the strategic plan for their business. While they may have participated in this exercise before, they now have to “set the table” and get people in their division excited about it. Not only that, but that plan might go to the C-suite, and if it’s business critical, may even be discussed at the board level.

How do they safely address what feels to them like a gaping hole sure to reveal their inadequacies? A great partnership with a manager helps a lot (in fact it is crucial). But an external coach, who can say in essence, “What you are going through is in many ways something I see all the time,” speaks volumes.

Additionally, an external coach can take it further, saying, “Let’s put a finer point on it, and then pinpoint precisely what you can do to meet this challenge.” This can be an especially empowering conversation for the executive. So, ultimately, it’s critical that the executive coaching relationship is based on trust, rooted in science, and delivers on business goals.


The Psychology of Executive Coaching

Executive coaching sometimes gets a bad rap in that nearly anyone can use the descriptor. Lots of former CEOs, executives, or even movie stars and athletes rebrand themselves as executive coaches after they retire. But great executive coaching needs to be rooted in some solid principles of psychology. While not comprehensive, here are some thoughts on such an approach:


Triangulate upon “truth” about the individual.

The psychology of executive coaching should include getting the executive’s perspective on themselves and gaining data on them from others in the workplace (typically from interviews and/or 360 surveys). This also includes the use of solid scientific assessment as well as high-quality, validated personality assessments. (At DDI, we develop our own personality assessments or work with trusted instruments such as the Hogan Inventories.)

Whenever feasible, add virtual or face-to-face acceleration center data to gain behavioral scientific evidence. This will give you and the individual further behavioral evidence of the current skill set. Do as much of the above as reasonable given the expense and the position to deepen understanding of the individual.

It continues to impress me how often I hear, “I’ve had some of this done before, but never pulled together like this. It is extremely insightful to get such a comprehensive picture. And I’m surprised at some of what I’m hearing and thinking.”


Leverage solid intellectual capital.

I’m fortunate to be tapped into a wealth of research-based intellectual capital. So, for example, when I’m helping an executive put words to her business challenges, I can efficiently pull from DDI’s comprehensive library of 30+ business drivers which ultimately get footed to critical competencies necessary for success.

I usually choose to keep the “HR speak” out of the dialogue, but pulling from that list puts both of us on a solid research foundation from which to build. I also have a library of pitfalls that executives typically fall into as well as catalysts which potentially avoid those pitfalls and propel individuals towards success.

I’m extremely rewarded by the clarity executives gain from simply talking through the challenges they feel and others see in a highly specific and guided manner. That grounding provides the basis for much of the prioritization and work to follow.


Work at the “key action” level.  

Focus on what an individual can say or do to amplify a strength, or compensate or develop a weakness. Sometimes this is not so obvious.

Take “building informal networks” for example. Sure, a natural ability and desire to connect with people is a real help. However, if overused, it also runs the risk of being a huge time sink. Less obvious might be taking the time to build a networking plan based on the information or expertise needed from others and scanning the environment based on who can provide it.


Recognize that some things are harder to develop than others.

There are huge individual differences in our wiring. Some executives are, for example, much more social than others. Strategies such as going to company or community-based events or doing regular “walkabouts” come naturally to them as a way of networking.

But to others also with a need to connect deeper into the organization yet much less social, more purposeful meetings with a mutual exchange of ideas and even resources are a better way to go. There are many different ways to achieve the same goals.


Summarize and make all commitments time bound.   

No description of the psychology of executive coaching would be complete without stressing the importance of overt commitments. I try to summarize agreements along the way. Also, all agreements end with what an individual is going to do (and if appropriate, the minimum number of times they are going to do it) and when it will be completed. This creates a verbal contract both with themselves and with me, and increases the likelihood of it actually getting done.


What Are the Goals of Executive Coaching?

Every executive coach can list the generic goals of a coaching engagement. They’ll tell you about generating self-insight, focusing on key leadership skills, and improving business performance.

And of course, you need to include key stakeholders, such as the executive’s manager and even an HR representative, in setting those goals as well. These additional viewpoints help to give the coach a full view of the situation, and generate shared goals for the executive’s success.

But when we talk about the psychology of executive coaching, there are a few key lessons I’ve learned about goal setting that make a huge impact:

1. Get real about the development appetite.

Years ago, I began the coaching process with a man likely in his late 50s. The relationship began with a comprehensive set of personality inventories coupled with a wide swath of behavioral feedback. I went through my usual routine of doing a deep dive review of his data and creating insightful questions.

In this case, he certainly was impressed with the level of insight I had into his personality, performance drivers, and derailers. His exact words were, “Yup, you nailed me.” Great!

Then came the kicker. “Barry, I gotta tell you, I am who I am. The company is making me talk to you. I’m not going to change. I don’t want my boss’s job or any other one around here. I like what I do reasonably well. All I want is to retire from this place in peace in a few years.”

While it’s great to work with executives who are highly motivated to grow, a low appetite for development isn’t a deal breaker. But it does mean you have to shift your strategy.

This executive did care about his legacy. He wanted to leave the company in better shape through his knowledge transfer. He also wanted a smooth transition, and to retain the deep professional relationships that had turned personal throughout his career.

The result of this focused approach? For his remaining years, he became less angry, more focused on giving, and glided into the next phase.

It’s important to understand why the person is here to be coached. Do they truly want behavioral change or to develop more quickly? Where is the common ground between what they want and what their company wants from them? How much passion are they bringing to the table that fits into a conventional definition of career development?

2. Every conversation must have an objective.

Years ago, when I was a frontline sales leader, one of my top producers used the phrase “just having lunch” to characterize aimless discussions that did not further her sales process. Sometimes, executives think of leadership coaching conversations the same way. It’s a chance to chat about whatever is on their minds.

But a good executive coach doesn’t let that happen. Anytime I am unclear on my objectives for a coaching conversation, I become a less effective coach. Sometimes these objectives are overt and shared. For example, the shared objective for my recent discussion with an executive was to discuss a long-term valuable employee 20 years her senior whose contributions had significantly diminished.

But sometimes, my objectives are more covert. For instance, sometimes my conversations are to determine whether an individual’s self-perception is consistent with the perceptions of others, where they differ, and what would have the most impact to work on.

The bottom line? Executive coaches should have an objective for each coaching conversation, whether shared or private. The objective may be one around getting to the root of how the executive must change to get the most impact. Or the goal of a discussion could be about how change will be measured, or defining indicators of progress and success. The coach should always take notes, and as appropriate, document agreements.

3. Authenticity is key to achieving goals.

One of the keys behind the psychology of executive coaching is to not waste time trying to change people to be something they are not. Rather, help them reach their goals in ways that align with their authentic selves.

I recently worked with a brilliant executive-level scientist who spoke only her version of “truth.” An introvert, she’s drained if she has to interact with others too much in a day. She also values work in the lab over networking with people. Most of all, she’s turned off by peers who spend too much time “grandstanding.”

To her, their jokes and speculations hog airtime and muddy the clean waters of scientific progress. But she also notices that these “grandstanding” peers tend to be more productive because of the way they harness and align organizational energy. Meanwhile, she struggles to get the followership she needs to accomplish her agenda.

Within our coaching conversations, she realized her frustrations were based in her desire to turn herself into someone she was not wired to be. She was not going to convert into a raging extrovert. She couldn’t slap on a smile to imitate those who naturally networked. But she could focus on a few key individuals deeply, who could help her accomplish her goals and for whom she had something to offer.

She also came to realize that “personal needs,” such as the need to be recognized for accomplishments, were very important to many around her. And like many introverts, once she put on her “personal needs lens,” she was a great listener.

Over time, she learned to develop her brand of visibility and networking, and to create a deeper well of support for her efforts. More success, always feeling like it was around the corner, had started to come her way when she started being the best version of her authentic self. It is the job of the coach to help the coachee get there!

4. Be prepared to throw hypotheses out the window.

Often, when I interview stakeholders at the start of a coaching engagement, they are quite sure about what the executive’s challenges are. These hypotheses are often a good place to guide early questions. But it turns out, they aren’t always correct.

I also always look for any inconsistencies in any feedback data I get about an executive. For example, “Barry is easy to work with,” versus, “Barry digs his heels in too often when he needs to consider another viewpoint.” Discrepancy of information is a rich vein to tap.

By digging in, a great coach can often get to the heart of the problem. And it often uncovers related but unexpected issues. For example, it might be that there’s misalignment across the whole team that’s causing the issue. The important thing is that the coach, executive, and their stakeholders need to be prepared for surprises. Their goals may change entirely.

How Executive Coaching Can Change a Company

One of the biggest mistakes I see companies make is thinking that executive coaching is about an individual. It’s not. While it’s a personal journey, it’s really about how their transformation ripples across the organization.

That’s why it’s so important to think strategically about the psychology of executive coaching and the outcomes you’re really looking to drive. Because this isn’t a therapy session or an opportunity to “just have lunch.” It’s a thoughtful process that will cascade better performance throughout the organization.


Learn more about DDI’s Executive Coaching.

Barry Stern is a former senior executive at DDI enjoying semi-retirement while loving coaching executives in individual and team contexts. He currently resides in Cleveland, Ohio where in the summer he can be spotted wandering the streets on his motorcycle, playing with his dog, or practicing tai chi poorly.

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