Four Case Studies About How SkillGym Supports Leadership Coaching

Quite often executive coaches leverage the power of SkillGym to enhance the quality of their coaching sessions. In this article we explore four interesting case studies to see how well SkillGym can solve many challenges typical of executive and leadership coaching.
Andrea Laus
SkillGym CEO
19 min read


In another article (“Boosting leadership coaching with Digital Role Play“) I have already explored how powerful SkillGym can be when it comes to supporting executive and leadership coaching activity.

We have seen that there are several ways to leverage A.I. for the purpose of upskilling managers on conversation during and in between coaching session.


In this article we will explore to case studies taken from the field, to see in practical terms ho professionals around the world already take advantage of this amazing solution.



Joseph is an executive coach dedicated to helping leaders growing their interpersonal skills.
He is 46 years old, professional certified coach and has over 10 years of experience in the field.
He mostly works with companies belonging to the Fortune 500 and he coaches executives in their forties.


His coaching format is one of the most classical:

  • Define the pain by investigating the “as is”
  • Set goals and then work on the various sides of the pain by listening
  • Asking questions
  • Challenging with dedicated role play sessions and supporting the growth with powerful questions


Typically, the way he is used to measure the outcome of his work is by having either a structured feedback session or, where possible, a 360 focusing specifically on the area of interpersonal skills.
Of course, each case is a little different, however this is the way he describes his most typical way of doing.


The first signals that something was changing started to arrive around 9 months earlier, when some of his clients started to ask for a more and more recurring pattern of requests.

Joseph says: “at the beginning it was only one or two… but then it went on the rise”.

The most common requests were about finding a way to relate his activity to some performance indicator that could be tracked on the way. Joseph referred a specific sentence “they needed to see the needle move”.


“At the beginning it was only one or two… but then it went on the rise”


When those requests started to become more than just a wish, he realized that some thoughts was deserved as to how operating a shift in the way he was delivering.

So, he took the subject seriously around the idea of a more “move the needle” oriented coaching program, where he could identify a bounce of significant indicators to be defined, agreed upon and consistently monitored by means of some sort of digital tool.


The initial idea was to find a way to be able to steer the program on the way, according to the signal coming from such metrics and being able, at the same time to show a positive and encouraging progress together with a more predictable final outcome of the traditional ways of evaluation a coaching program.

Since Joseph was deeply into the interpersonal skill development and was absolutely convinced about the importance of Role Play as coaching strategy, he considered about searching in this field for techy tools that could help.


The choice went on SkillGym for its powerful way of delivering a library of stories to play with and enough data to be extracted from the digital tracking of its usage.

In this way Joseph could, at the same time, provide the coachee with consistent practice (since, according to him, improvement comes from the application of knowledge to practical situations) and collect enough information to build those metrics needed to move the needle.

In fact, he noticed that the platform was providing many types of different data, even more than what he could possibly handle.

And certainly, more than what he needed for his first attempt with this new strategy.


So, he decided to focus his attention on just two key metrics that seemed appropriated to provide meaningful information about the impact of his work.

The first was the level of CONFIDENCE with which the coachee was dealing with the conversation in the role play and the second was the level of AWARENESS with which the coachee was able to judge his own performance against the quality measured by the platform.

The way he packaged the Confidence measure was quite simple: the higher the overall score of the digital role play at the end of the conversation, the higher the confidence in the task.

He just made sure that such score was in fact measuring the quality of the impact of the coachee’s behaviors on the approach of the virtual character.


As for the Awareness Joseph thought about integrating a certain number of questions to be asked to the coachee at the end of each role play, so to compare his self-assessment to the evaluation of the platform. The higher the matching, the higher the awareness.

After a few weeks of piloting, Joseph was able to pivot his traditional format, making room for a consistent ritual based on practice, measuring and adjustment of the exercise.


Basically the idea was, once the main goal was defined with the client, to link it to the two indicators of his program: confidence and awareness that would be then measured consistently across the sessions by asking the coachee to play specific role plays that were scheduled in between of each meeting.

During the coaching session, Joseph and the coachee would discuss the outcome of the simulation always referring to those two metrics and comparing them with two different benchmarks.

  • One was the result achieved by the same coachee during the previous session (the so called “self-benchmark”) where the scope was to measure a trend of improvement.
  • The other one was a comparison with the average result achieved by a cluster of comparable coachees, as registered anonymously by the platform across all users enrolled by several other coaches in the Country.


This second indicator had the scope of setting a baseline and indicate where “the rest of the world” was hanging around.

After each session Joseph and the coachee had enough data to help defining what had to be the next role play to be challenged, thus adjusting dynamically the schedule of practice.
After 6 months from the beginning of the new program, Joseph was ready to collect some comprehensive feedbacks from the field.


As expected, it was a mix of comments that could be roughly divided into two categories.
Signs of appreciation and alerts on possible issues (most of the signals of this kind where already collected and somehow managed by Joseph on the way. But the final brainstorming was useful to Joseph to draw some important conclusion on how to better define this new approach).


On the other side, one coachee became passionate by the amount of data that the platform was providing beyond the two key indicators chosen by Joseph and started to ask for Joseph help in order to learn how to influence such measures.

Joseph decided to take a stand towards the idea that his role was that of coaching, not training the coachee.


His reported expression was “I am here to raise questions helping you find your way, not to explain you my way”, wisely marking the fine line between training and coaching people.
Finally, of course, some leaders were complying about the extra effort of playing schedule role plays… here Joseph remarked that “moving the needle” requires two ingredients: metrics (of course) but most importantly effort to practice. “no pain, no gain”… and most of them found the time.


“I am here to raise questions helping you find your way, not to explain you my way”




Melanie is 42 and she is an Executive coach (professional certified coach) supporting emerging leaders and hi potential with career development advice.
Her coaching format includes 2 live coaching sessions of 90 minutes every month, over a cycle of 6 months period.


Each session with the coachee includes always one role play focusing on interpersonal skills and, of course, the relevant debrief time.

Since quite a few years, especially working with emerging young leaders, Melanie was registering many requests about evolving the traditional way of delivering her coaching advice.

Particularly, her clients were more and more asking about two, apparently diverging needs:

  • On one side they wanted more practical activity, including more role play time to try and discuss about situations. They felt that practicing was an efficient way to unleash new skills.
  • On the other side, however, they were suffering about being tight to a schedule of meeting that was more and more difficult to fit into an ever-busier agenda. They were asking for reducing the time spent together!


The “go digital” was a common request, they were used to accomplish a lot of activities with the help of digital technology that was helping them to shrink time and being ubiquitous. Which was still not happening in their coaching sessions.

Melanie decided to try a different way of packaging her service by moving part of her activity online.


The idea was to cut by half the physical one to one presence and, meanwhile, double or even triple the opportunity for letting her coaches practicing. Of course, she knew that she still had to stay in the picture, so she decided to deliver extra value by making herself available on-line as well for supporting the remote practice activity.

The idea of looking at SkillGym was quite natural: she had to remove herself from the practice delivery of role play, otherwise she could never add more role plays without doubling her personal effort and this could never be sustainable over time, so she decided to adopt SkillGym because of the three following features:

  • On one side she needed a flexible way to let her coachee book practice sessions on the way. She wanted something where her coachee could automatically receive invitations to schedule one role play and decide when to fit it in their agenda. At the same time, she wanted to make sure that, in case the coachee did not show up for the scheduled role play, the platform was smart enough to send reminders and in the end proposal for rescheduling
  • On the other side she wanted a solution robust enough to allow a comprehensive monitoring of the practice activity carried out by the coachee. Something where she could review the role play at any time and understand where any help was needed.
  • Finally, she thought that a good remote collaboration system within the platform could allow for an asynchronous way to deliver powerful questions. There was no need to discuss about a role play face to face.

It is quite interesting to look at how the coachee got engaged in the new remote and self-paced practice activity.


Basically, the idea was that:

  • The fictional character (let’s call him “Mark”) would interact with the coachee much before starting the role play
  • He would directly write an email like: “Hi, I am Mark, and I would like to ask you for a quick feedback session on XYZ. I know you are busy, so please click the link below to open a doodle with a few slots, let’s see if we can make it.”
  • If the coachee did not respond, Mark would send another try
  • Finally, on the scheduled day Mark would write a confirmation email like “Him It’s Mark… and it’s today at 5pm, just to let you know I’ll be there.”
  • Sometimes if the coachee did not show up Mark would write again to say, “hey don’t worry, I guess you got trapped… let’s reschedule, I was quite busy too.”


The result was stunning: 85% of the time the coachee was duly there on time. And for another 10% just a second try was enough to find the right fit in the “busy” agenda.

The majority of the coachee explained to Melanie that they felt obliged to respect an appointment. They were acting as if it was a real schedule with a real person! Very efficient.


Also, it is remarkable how certain smart features of SkillGym could solve the fact that Melanie was not there when the role play was played.

She had the possibility to access to a recorded version of the interview, move through it and, with the help of augmented reality, review any blindspots of the conversation. Such as the reaction to stressed body language, the way a certain behaviour was applied or even the recurrence of specific patterns and approaches.

It took on average 7 minutes to open a role play, review it, find a spot and post one or two questions on the chat board.


The coachee would be notified and when available would access, read the question and reflect on his own. Of course, with the possibility to reply when needed.

In this way Melanie could manage up to three times the number of role plays with the same quantity of effort without the need of locking each other’s agenda.


In the end her new format became very popular with her clients, especially the millennials.
She reduced her presence sessions down to 1 per month, same duration of 90 minutes. During that time, they both had more room for discussing about how to apply certain behaviors, as witnessed in the role play, beyond the boundaries of the specific context.


She increased the quantity of practical exercises without messing up the busy agenda of her leaders and she still was perceived as available and helpful when needed, with even more laser focused powerful questions working as eyeopeners on blindspots.

Needless to say, the comments coming from her clients were very enthusiastic: EFFICIENT was the most popular keyword. They felt like their time was more valuable.

And also, “GAME” was another popular keyword. The digital role play was perceived like a relaxing time where they could learn and get entertained at the same time.


There were, however 2 issues that Melanie, as she reported to us, found on the way. And apparently, they were two quite diverging issues.

  • On one side some of the coaches started to think that the role play was rich enough with information that “they could even go alone”, like if they were saying “I don’t need a coach anymore”. But in the end, it was not how they did: in the end, at the final review, she was rated very high as regards remote support and also the question “do you think remote support is a key element of your online experience” was highly scoring.
  • At the opposite, many other coachee were asking for more asynchronous help, sometimes forcing Melanie to turn her advice session into a longer remote discussion. But it was always focused on the subject and, in the end, Melanie says, the possibility to differ the answer made it easy to keep the pace.


To summarize, Melanie gave us the following very simple indeed claim to define this shift “Blended Coaching”, she did nothing more than moving online those activities that, once well supported by technology did not require her presence anymore.

By the way it is interesting to notice that coachees, on average, reported in the final survey that they felt much more comfortable with self-paced role play not only in terms of practical organization of their time but also from a point of view of lower pressure perception when making mistakes.


What is important, however, are the 3 key lesson learned by Melanie that helped her to keep the steer firm on the way:

  1. The coach can’t be cut away: coachees still have the need for discussion
  2. Remote practice can be fun
  3. There is no need for real time sometimes: waiting one day to get my review of the role play is ok



Tom is professional Leadership Coach, with 3 years of experience about Digital Role Play.
Tom was assigned to Kate, a middle manager of a middle size company, in charge of a team of 20 people.
He was called because the annual performance appraisal suggested that Kate was below average as regards her commitment and skills in giving feedback.

Her reports were much less happy than the other colleagues in the company as regards Kate’s commitment in providing on-time and straightforward feedback in their activity. Kate was aware of this situation and quite aware of the reasons behind this.


Some of the things she told Tom during their first session were: “Often… I know I should give feedback… but I always find other jobs to do” and “I Don’t feel Comfortable”.
She basically reported to Tom that Giving Feedback was somehow outside her comfort zone.

So, Tom and Kate decided one specific goal for their coaching sessions: helping Kate growing her confidence, expand her comfort zone and include the key activity and responsibility of regularly providing her reports with consistent feedback on their performance.

Tom decided to work on this subject introducing SkillGym to let Kate practice with typical performance feedback situations and to discuss upon those conversations during their coaching sessions.


”Often… I know I should give feedback… but I always find other jobs to do” and “I Don’t feel Comfortable”


The idea of Tom was simple: confidence comes through practice and role play represent a very good form of «safe» practice to warm up and prepare for real life.


Tom was expecting two key advantages from using digital role play: on one side Kate could play «alone» making the safe environment be perceived as even safer and they would have a lot of material upon, with powerful coaching questions.

Tom scheduled a consistent practice for Kate in between of coaching sessions, as a follow-up activity along the 6 months they met on their coaching program. The idea was that of a regular number of simulated feedback session, avoiding overwhelming her normal schedule with too much exercise.


Kate ended up by playing a total of 22 conversations over the 6 months, each one taking on average 17 minutes to complete. And Tom and Kate discussed 8 of those conversations, during their coaching sessions.

Before the coaching session, Tom spent around 10 minutes reviewing the metrics of the conversations played by Kate, in search of interesting triggers to discuss during the session. During each session, either Kate or Tom proposed to review some passages of a specific conversation.


The method of Tom included:

  • Listening to some passages
  • Reviewing the underlying behaviors
  • Asking Kate questions about why and how she applied those behaviors
  • Leting Kate focus the key points behind her decisions
  • Stimulating her with questions that helped Kate to find a better strategy for the next conversation


On average this role play debrief took around 20 minutes in each session where they decided to focus on a conversation.

The joint review showed a couple of recurrent elements that became powerful triggers in the debrief. On one side, the “Virtual reports” of Kate consistently appreciated her approach, especially when it was oriented to support them in doing better.

On the other side, Kate noticed that some of her specific behaviors, such as asking open questions, consistently triggered the same type of welcoming body language in the counterpart.


Of course, Tom leveraged those triggers with powerful questions such as: “how would you do, to get those same reactions in your next role play?”.

Or “why do you think your report appreciated that question?”.
Also, and this is very important, Tom started to ask if the same reaction was emerging also during Kate’s real-life feedback sessions which were becoming more and more frequent.

In fact, the stronger the growing confidence of Kate (look at the blue line along the months, crossing the evolving perceptions of Kate as noted by Tom, here above) was generating a growing number of occasions for Kate to schedule real life structured feedback sessions with her reports (the green bars).


In fact, the more Kate was involved in building her confidence through role playing, the more Tom noted two different kind of perceptions and comments coming from Kate. On one side she was more confident because she perceived that her activity was perceived as useful from her reports during the conversation.


On the other side she appeared to be more and more in control of the situation, just like if playing the role play on a consistent base was building in Kate’s mind a collection of Deja-vu situation, with which she was getting more and more familiar.

The more she played, the more she knew what to expect in the next conversation. According to Kate this exercise was for her “One accelerator of experience”.

Tom, still involved in providing services to the same company, met Kate again later on and he was happy to know that the following year, her performance appraisal highlighted a much more confident Kate as regards her skills and commitment in giving consistent feedback to her reports.


According to Kate this exercise was for her “One accelerator of experience”


Tom and Kate reported 3 main elements of Tom’s strategy to be relevant to the result.

  • The first was consistent practice. Kate noticed that, even though at the beginning she was somehow «forcing» herself to find the time to play, the more she played the easier it was for her to consider this task as something she could manage.
  • The second was the use of AI based role play, which gave to Kate the feeling that even playing the same role play more times, each time something different was going on. This, she said, helped Kate to keep striving for the result, instead of playing on a known plot.
  • And finally, the possibility to reflect on what happened looking at the situation from outside with the help of Tom helped Kate to visualize where she could improve and, most of all where she was providing value to her reports.


At the same time Tom reported one main issue that at the beginning risked impacting his strategy.
In fact, Kate often told Tom that she had no time to play in her busy agenda.

After the initial few weeks… where Kate actually didn’t play at all, Tom decided to ask Kate to consider each Role Play as a real feedback session and to schedule it on her weekly busy plan.

This approach changed the situation: from there on, Kate planned with 2 weeks advance each conversation, and in this way those conversations entered her routine.

Tom learned to underline since the beginning the idea of scheduling virtual conversation on his coachees agenda instead of promoting free practice.



Linda is a Leadership Coach working inside a large corporation.
She has over 1 year of experience about Digital Role Play and she reported a very interesting case study with Jeffrey, a first-time manager in the same corporation, in charge of a team of 12 people.

She was assigned to Jeffrey as part of his induction activities and already during the first coaching session, when Linda and Jeffrey played one face to face role play, Linda noticed that Jeffrey had little experience with Leadership Conversations.


In fact, in the debrief, Jeffrey had the tendency to overestimate his own performance, while Linda noted several weaknesses that were not noticed by Jeffrey. Some of the quotes of Jeffrey, noted by Linda sounded like: “I did well, she doesn’t want to understand”, justifying why he did not manage to reach the conversational objective; or “I have my way”, “I know what he needs”.

This is the kind of statements that Linda listened to.


All in all, it was clear to Linda that Jeffrey had a problem of self-awareness about the real outcome of his critical conversations. So, they decided to focus one of their objectives on this issue and to find a way to help Jeffrey to develop a more critical approach to his way of judging his own performance and behaviors.

Linda decided to work on this subject introducing SkillGym to let Jeffrey practice with critical conversations, with the specific goal to pay attention at the difference between Jeffrey’s perception and that of the virtual report.

In fact, SkillGym allowed the possibility to listen to the virtual report while debriefing with a colleague about the conversation he had with Jeffrey.


On top of that Linda would dig inside some parts of the conversation using the replay features, to check in details the awareness of Jeffrey on specific behaviors. Linda decided to use SkillGym mainly in face to face sessions.

She wanted to observe the behaviors of Jeffrey on her own during the simulation, to have more elements of discussion and make up her fresh mind upon his approach and have a clearer vision for asking interesting questions during the joint review.


The method was very simple:

  • Linda would present the situation
  • Jeffrey would take few minutes to prepare the meeting and then play the meeting on his computer
  • Linda would attend discretely aside
  • After the conversation and BEFORE getting a feedback from the simulation, Jeffrey would face a structured self-assessment time
  • The digital role play selected specific moments of the conversation, asking Jeffrey to reflect on his own approach and performance and rate them on a scale of 1 to 4
  • Immediately after, Jeffrey would listen to the opinion of the virtual report on the same topics


After this exercise, that lasted on average 15 minutes, Linda would take another 10 minutes discussing the outcome with Jeffrey.

She starts asking about Jeffrey’s perception on the virtual report’s feedback and why it was diverging from Jeffrey’s self-evaluation.
This part was very important, since it forced Jeffreys to compare his position with that of an objective tool.

Then Linda would expose Jeffrey to some metrics coming from the system.

Specifically, the Digital Role Play calculated the AWARENESS INDEX, measuring the distance between the two evaluations (the one of Jeffrey and the one of the simulation).
This index was taken by Linda and Jeffrey to measure their progress, with the goal in mind to move from an initial 52% to a more reasonable 80%.


Then Linda would focus on some specific passages of the role play and, with the help of the replay of the conversation, she asked to Jeffrey to explain the relation between some of his behaviors and the relevant impact in the virtual report.

This was mindblowing for Jeffrey. He could:

  • Frame the situation
  • Focus on what happened from a third perspective
  • And start seeing the point of view of the other person


Specifically, Linda found one interesting pattern to work on by asking a series of powerful questions she helped Jeffrey to understand that most of the time that Jeffrey was receiving from the virtual report one answer that was intended to be one example to explain the report’s opinion, Jeffrey tended to consider it as a mere justification.


At the same time, triggered by this perception, Jeffrey tended to answer harshly and, still, to consider his own answer as the right and balanced way to refocus his report’s priorities.

Then, when the counterpart manifested a frustrated reaction, Jeffrey interpretation was that of an attack.
Once Jeffrey understood this recurrent pattern, it became easier for him to focus on certain perceptions and work on them to rebalance his point of view.


Already after few sessions where Linda and Jeffrey applied this coaching strategy, Linda started to notice a shift in Jeffrey’s approach.

In fact, as a first step, he started to improve his skill of self-evaluating his overall performance,
And later on, this ability evolved, and Jeffrey developed a more critical approach on details of his own behaviors.


Jeffrey became more and more sensible to listening to the weak signals coming from his virtual report.
In five months, Linda was happy to notice this result.

Jeffrey’s appraisal on his own performance during critical conversation was much more mature and almost matching her evaluation.



Linda and Jeffrey reported that 3 main ingredients of SkillGym have impacted the result:

  • The first was Linda’s strategy of «reflect and listen». In fact, she asked Jeffrey to self-evaluate his own performance and, immediately after, to compare such evaluation to that of the simulation. It was the starting point for the change. Noticing a diverging score was the way to look for a solution.
  • The second was the use of video-based role play. Part of Jeffrey commitment was that of investigating the body language of his counterpart in search of weak signals showing a diverging perception of the quality of the ongoing conversation. Playing a digital role play where the counterpart was a professional filmed actor, was a great element in this exercise.
  • And finally, the possibility to reflect on what happened, looking together at the situation from outside, helped Jeffrey to visualize where he could improve and, most of all where he was misperceiving the reality


When asked about lesson learned, Linda reported that, at the beginning, she faced the following issue with Jeffrey: he was trying to justify the mismatch in evaluation score saying that “anyway this is not a situation I would normally experience”.
Something like if he would not accept the evaluation of the Digital Role Play.


Linda decided to ask Jeffrey to simply start from that situation and immediately after search comparison with real life similar situation.

Jeffrey started to notice that, no matter what, he could see a lot of similarities between that virtual situation and those of his daily experience in real life.
Linda learned that it was much better to declare this approach since the beginning, in order to leverage de-contextualized situation as a way to reconnect to real life just after.


What’s next

Wow, what a long series of case studies. Sorry if I went too long, and thank you for following me so far 🙂

If you are looking around to find the Digital Role Play solution that suits your need, please give a look around our website, there is plenty of inspiring contents including pre-recorded webinars and articles and of course we would be delighted to continue this conversation with you, all you need to do is book a 1-hour discovery call with us.

Enjoy the rest of your day.

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