Jenn Masse Of Conshy Coaching: 5 Ways Empathy Will Affect Your Leadership

An Interview With Cynthia Corsetti

Empathy can also help you manage conflicts more effectively. Heightened levels of emotional intelligence and active listening will help you gain a better understanding of the conflict at hand, the various perspectives at play, and the emotions that are being triggered as a result. Leveraging empathy and a coaching leadership style will help you acknowledge and validate the situation and other parties, align everyone to an agreeable goal, and navigate the conversation towards a resolution with ease.

Empathy, the ability to understand and share the feelings of another, is increasingly recognized as a pivotal leadership trait. In an ever-evolving business landscape, leaders who exhibit genuine empathy are better equipped to connect, inspire, and drive their teams towards success. But how exactly does empathy shape leadership dynamics? How can it be harnessed to foster stronger relationships, improved decision-making, and a more inclusive work environment? As part of this series, we had the pleasure of interviewing Jenn Masse.

Jenn Masse is an ICF Certified Mindful Leadership Coach and Organizational Mindfulness Trainer and Facilitator who empowers her clients to make the mindset and behavioral shifts necessary to break free from limitations holding them back from unlocking their full potential. Said simply, Jenn helps busy executives and leaders develop the tools necessary to manage their time, stress, and energy so things just feel easier!

Jenn has been a full-time professional coach and owner of her coaching practice, Conshy Coaching, since 2018. She specializes in helping leaders challenge the “old” way of doing things, embrace the human side of leadership, and empower their teams to deliver high-end results on a more consistent basis.

Jenn currently lives in Central Oregon with her husband and pup, and spends her free time playing in nature, volunteering with local organizations, and reading.

Thank you so much for joining us in this interview series. Before we dive into our discussion about empathy, our readers would love to “get to know you” a bit better. Can you share with us the backstory about what brought you to your specific career path?

Sure! Prior becoming a Certified Coach, I worked in a corporate environment for over a decade. From accounting to project management, to sales, to marketing and business development — I was constantly chasing careers, promotions, and this ‘preconceived notion of success’ that was promised to bring me happiness. I was incredibly good at what I did and excelled in all these positions, but constantly felt under-utilized, under-valued, and “empty.”

It wasn’t until I found myself crying ugly, snotty tears in my boss’s office did I realize that something needed to change. It was in that moment that I realized I would never truly be appreciated for the value I could bring, or in the position to truly empower and inspire other people, until I took control of my story, my future, and my career.

I enrolled in an ICF credentialed coaching program the next day. That was in 2018. Over the next eight months, I experienced firsthand the power of coaching. It truly transformed who I was as a person, employee, and leader, and when I received my first coaching certification in July of 2019, I quit my corporate gig to start Conshy Coaching.

I’ve never looked back. Today, I’m fortunate enough to be in a position where I can empower and inspire leaders to challenge the “old” way of doing things, embrace the human side of leadership, and empower their teams to deliver high-end results on a more consistent basis.

Can you share the most interesting story that happened to you since you started your career?

I always knew that my role as a coach would directly and positively impact my clients, which would inherently impact their teams, however — hearing stories about the ripple effect of coaching never ceases to amaze me.

In Glennon Doyle’s book ‘Untamed’, she writes “Playing dumb, weak, and silly is a disservice to yourself and to me and to the world. Every time you pretend to be less than you are, you steal permission from other women to exist fully.”

As a coach, I see the flip side of this argument as well. When you make the choice to invest in yourself, develop tools to better manage your time, stress, and energy, and show up as the fully authentic version of yourself, you give permission to other people to do the same.

When my clients start to implement the tools and strategies necessary to lead their teams effectively, their team members take notice. When my clients start to embrace the human side of leadership, practice mindfulness, increase their emotional intelligence and listening skills, their team members feel the impact, and start to adapt and lead themselves and interact with their peers or teams the same way.

And, while it seems small — it truly moves me every time a client shares a story about how coaching has had a broader influence on their team, peers, or family. And how their decision to invest in themselves positively impacted the lives and careers of so many other individuals. It’s truly magical.

What do you think makes your company stand out? Can you share a story?

Candidly speaking, it’s my approach to coaching. As an ICF certified coach, I obviously adhere to the ethics and competencies laid out for professional coaches, but beyond that, I think my no-nonsense, direct, but compassionate and fun approach resonates deeply with people.

Additionally, I use a unique mix of science-backed mindfulness and neural-training strategies and assessments including iPEC’s Energy Leadership Index, Gallup’s Clifton Strengths, and Positive Intelligence’s Saboteurs assessments to create a baseline of education, and data points that will drive and shape our conversations moving forward.

This approach is far more impactful because it allows my clients to evaluate their position and situation from a new perspective, and discuss the pros, and cons of various approaches.

Lastly, the International Coaching Federations (ICF) defines coaching as “partnering with clients in a thought-provoking and creative process that inspires them to maximize their personal and professional potential.” What makes me stand out from other certified coaches is that I don’t rely solely on asking questions to get my clients from point A to point Z, or tell them what they need to do. Why? Because you don’t know what you don’t know, and I firmly believe it’s not fair to make you struggle to come up with a new approach to an old problem on your own, and you’re far more successful when you use new perspectives and information to create your own strategies and solutions.

One of my favorite clients once said, “I felt like I was out on a raft with a volleyball named Wilson going nuts with stress and dehydration in the middle of the ocean, and Jenn just walked up and said, ‘Hey, reality check, you’re in the shallow end of a public pool, you can definitely touch the bottom and you can get out whenever you want.’”

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

Authenticity — I am a firm believer that there is no “right” way to do anything, only your way. There are so many people out there trying to sell you these signature systems, programs and solutions that will help you become a more effective leader, but the truth is that you are the only one that knows what is best for you, your team, and your organization. I don’t pretend to be anything other than who I am. I show up fully, and authentically, in a hoodie and baseball cap, and help my clients make sense of the ideas swirling through their heads. My authentic approach allows me to confidently recognize that I’m an expert in my role as a coach, and that my clients are experts in their roles. I’m direct, I’m compassionate, and I’m able to create a safe space for my clients to develop their own unique formula for success.

Curiosity — I used to think I knew all the answers, the right way to do things. I was incredibly judgmental of those who did things differently or couldn’t get to the answer as quickly as I did. These behaviors stifled my professional growth, led to deeply rooted resentment, and extreme levels of burnout. It wasn’t until I let go of my need to be in control, my need to be right, and my obsession with being “the best” that I was able to tap into my full potential. I now approach every aspect of my life with curiosity. Curiosity has helped me be open to learning new information, bend and pivot my business model as new information arises, and — most importantly — it helps me be an amazing coach for my clients. Curiosity allows me to be fully present in the moment, and rather than trying to solve their problems, I can listen to what they are saying, or not saying, to help them connect the dots and find their own answers and solutions.

Highly Perceptive — As someone with ADHD, I’m great at getting off topic and eventually finding my way back to the starting point. This is both a blessing and a curse, but lately, as more and more clients are soliciting help with deep focus and attention, I’m realizing it’s a huge benefit. My clients often start talking about one topic, and before they know it, they’re out in left field talking about something else without knowing how they got there. I’ve realized that my ADHD in these situations is a super-power because I am deeply perceptive and have a strong intuition. These traits allow me to follow my clients’ train of thought, connect dots they may have missed, and ultimately bring them back to the initial conversation with a deeper level of self-awareness and perspective. My always clients always tell me that their favorite thing I say is, “So what I’m hearing you say is…”

Leadership often entails making difficult decisions or hard choices between two apparently good paths. Can you share a story with us about a hard decision or choice you had to make as a leader? I’m curious to understand how these challenges have shaped your leadership.

I’d have to say the hardest decision I ever had to make was leaving the stability of my corporate job to start my coaching practice back in 2019. Fear-based drivers such as financial security, reputation, and a deep-rooted belief that I made bad decisions made it very difficult to make that leap.

However — I knew, deep down in my core, that I wanted to be able to empower and inspire people, and that my current career trajectory wasn’t going to provide those opportunities for me and was taking me further and further away from my core values of freedom and connection. These factors, and the sheer potential that I’d be able to help others navigate toxic work environments and create supportive human-centered organizations, spurred me into action.

Today, I use the same benchmarks when facing tough decisions in my business, and generally opt for the choice that will align with my core values and empower me to, directly or indirectly, empower as many people as possible.

I’ve seen this values-centered approach work time after time with my clients, and it’s one of the main reasons that I encourage my clients to take the values assessment that’s available for free on my website. Once they know their core values, those tough decisions feel easier and more aligned. It becomes a lot easier to remove the fear-based blocks, and confidently stand in their decisions and truth, even when those decisions might challenge the old-guard way of doing things at their organizations.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. Let’s begin with a basic definition so that all of us are on the same page. How do you define empathy in a leadership context, and why do you believe it’s a vital trait for leaders to possess in today’s work environment?

Anyone that has worked with me knows that I’m a Brene Brown junkie. For those who aren’t familiar with Brene Brown, she’s a PhD and Social Worker who has dedicated her life to studying topics such as courage, shame, vulnerability, and empathy.

Brown defines empathy as “connecting to the emotions that underpin an experience.” It means connecting, at a deeper, more human level, to the emotions and feelings that result from an experience. I love this definition because, as a leader you might not understand what your team member is going through, but you very likely have experienced similar emotions at a different point in your life.

Empathy is crucial for leaders, because it allows you to build a deeper relationship with your teams, understand their needs and motivations, and create a positive work environment. Studies have also shown that empathetic leadership leads to improved communication, innovation, engagement, retention, inclusivity, and work-life balance.

Can you share a personal experience where showing empathy as a leader significantly impacted a situation or relationship in your organization?

I’m going to use a client example here because I can’t think of a better way to show how active listening and empathy can radically shift your impact and how you’re viewed as a leader.

This client, an EVP at a major advertising agency, hired me to help her become a more impactful and influential leader. This client was wildly successful in her career, with several awards under her belt; however, her passion often led to conflict with other teams and got in the way of forward progress. When she started coaching, she solicited feedback from her boss on areas to improve, and he said:

“Learn to tame the bazooka. You’re incredibly passionate, about the work we do and putting out the best product in the most efficient manner, but it would be great for you to consider HOW things get done, and what steps and process are best for all parties, even if they are not the most efficient. Additionally, you usually know what needs to be said, but sharing the microphone with, and creating opportunities for your partner, and your account and strategy partners, would go a long way!”

For the next six months, I helped this client embrace a new way of doing things. From forcing her agenda, bulldozing conversations, belittling her partner, and giving the account team hell when they challenged her on budget, to becoming an active listener and observer, a true partner who solicited other ideas, and an empathic leader and partner who listened to the concerns of the account team with the goal of finding a win/win solution, the transformation was nothing short of radical — — and inspiring.

I remember one time she came to a session bouncing with energy. She said “Jenn — you wouldn’t believe this!! I just got out of a meeting with the account and strategy teams, and other than opening remarks to align on our understanding of the client’s request and meeting objectives, I didn’t say anything. And WHO KNEW! The rest of the team had some amazing ideas on how to approach this pitch, and the account team was on board the entire time. And I’m just blown away. Who knew so much could be accomplished without saying anything!”

Six months later, here were her boss’s comments during her year-end performance management review:

“It is with pleasure and a big smile that I get to write this review. Reading her self-assessment, I am struck by how much she has been able to glean from her coaching experience. And from my perspective, I’ve seen a big difference too. Not like night and day and not like anything in particular was “wrong” but I just see more prudence, thoughtfulness, maturity, collaboration and wisdom coming through in her leadership style. I no longer see her as a ‘bazooka’ but rather as one of the most influential leaders I have on my executive team, and frankly, in the entire organization.”

I love this example, because it shows that when you invest in yourself, are willing to challenge your old-ways of doing things, and embrace a new way of doing things, other people notice. In addition to this amazing review from her boss, this client also received over 5 pages of comments from 20 other individuals at the organization gushing about how much she’s changed and how she has become one of their most trusted advocates and partners within the organization.

This client example is just one of many, and it all started with this individual having the courage to schedule a complimentary exploration call on to learn more about how coaching could help her become a more impactful and influential leader.

How do empathetic leaders strike a balance between understanding their team’s feelings and making tough decisions that might not be universally popular?

This is a great question, because often my clients know the best decision for the organization is going to negatively impact their team. This awareness lays the groundwork for empathy.

Empathy allows you to recognize and speak to tough emotions, while also standing firm in a decision that might not be universally popular or well received. Said simply, having empathy doesn’t mean avoiding sucky things because you know your team won’t like it. It means empathizing with your team that the situation or decision, does, in fact, suck and you’re there to hold space and support them as they navigate the situation.

I also find that Holographic Thinking empowers leaders to make grounded and confident decisions that equally balance logic, emotions, and intuition. When this approach to decision making is used, it makes communicating the decision and fall-out to your team so much easier because you’ve already taking the human-side of the equation into the picture. For anyone that wants to learn more about holographic thinking, I’d encourage them to check out this recent article I wrote on the topic.

How would you differentiate between empathy and sympathy in leadership? Why is it important for leaders to distinguish between the two?

Again, I’m going to leverage Brene Brown’s definitions and perspective here. She states, “Empathy fuels connection. Sympathy drives disconnection.” From a leadership perspective, empathy is understanding. It’s the ability to understand what the other person might be experiencing, and extending compassion, where possible to help them navigate the situation that they are in. Sympathy is more of an arms-length transaction, where you might feel sorry for the person, but you don’t do anything to help them feel seen or heard. Empathy is recognizing that an employee is struggling with their workload or mental health, and sitting down with them to understand what support can be provided to help them succeed. Sympathy is saying “I’m sorry you’re feeling overwhelmed,” and leaving it at that.

What are some practical strategies or exercises that leaders can employ to cultivate and enhance their empathetic skills?

The number one strategy I recommend for anyone who wants to become a more empathetic leader is to increase their emotional intelligence. Empathy is defined as “the ability to understand and share the feelings of another,” so if our emotional intelligence is low, we will inherently struggle with being an empathetic leader. I discussed this concept in more detail on my blog in my book review of “Permission to Feel” by Marc Brackett.

Here are three tips that I typically share with clients who are looking to increase their emotional intelligence, and train themselves to become more empathetic.

First, increase your emotional vocabulary! Brene Brown’s team did a study a few years ago and found that of the thousands of people they surveyed, most people could only name three emotions. Three! Can you believe it? High levels of emotional intelligence are required to truly embody empathy, because if you can’t distinguish between stressed, overwhelmed, worried, or anxious, then you can’t truly understand what your employees, peers, or other humans are feeling or experiencing in the moment.

Second, track your emotions and emotional reactions. While we all process emotions differently, this is a great way to improve your emotional intelligence. By understanding your emotions more deeply, you’ll be able to be more empathetic to your team members when they have similar emotions. Emotional intelligence also enables emotional boundaries, allowing you to set your emotions aside and be more present with your team members.

Lastly, the “Just Like Me” mindfulness practice is specifically designed to help people cultivate empathy on a regular basis. And before you roll your eyes, science has confirmed that visualization practices like this one fire mirror-neurons in our brain, creating new pathways, and allowing temporary emotional states, like empathy, to become permanent traits.

How can empathy help leaders navigate the complexities of leading diverse teams and ensure inclusivity?

It starts with active listening and taking a coaching leadership approach. Don’t assume you have the answers or know how to resolve the various challenges your team is facing. Actively listen to what your team is saying, ask clarifying questions, and empower them to propose various solutions and approaches to the challenges at hand. This approach will create a psychologically safe environment, cultivate trust, stem innovation, and welcome diverse perspectives from everyone on your team. Empathy and understanding can also help you lead with the assumption that everyone “is at least 10% right.” This concept in it-self will help you lead diverse teams and ensure inclusivity because you’re not immediately writing off ideas or perspectives, it opens you up to listening and understanding which 10% of an idea you can grab hold of to carry forward.

Based on your experience and research, can you please share “5 Ways Empathy Will Affect Your Leadership”?

  1. Cultivating emotional intelligence and empathy will have a massive impact on your ability to lead. Just scratching the surface, it will help you build a culture based on trust and openness, which will lead to more collaboration, innovation, increased engagement, improved communication, and so much more. Look at the client example I shared above. This client had always been a superstar in her career, having achieved all of the major marketing awards except the elusive Grand Prix. Within a year of embodying a more empathetic approach to leadership and her approach to other teams, her team won the Grand Prix on a new project. That was a few years ago, and candidly, I’ve lost count of the number of awards she’s received since then!
  2. In a recent study conducted by the American Institute of Stress (AIS), 83% of US workers suffer from work-related stress, with 25% saying that their job is the number one stressor in their lives. They go on to say that the main causes of workplace stress are workload (39% of workers), interpersonal issues (31%), juggling work and personal life (19%), and job security (6%). As a coach who regularly works with stressed-out executives, leaders, and high-impact individuals, I’d also chime in that stress is a result of constantly changing priorities, the push to do more with less, and the general sense of not feeling seen, or heard, or feeling as if they have the autonomy to make decisions about their workload or their team’s direction. Increased empathy as a leader will help you combat this stress, because it will empower you to become a more active listener, recognize signs of stress and burnout before it becomes chronic, streamline communications and work with your employees to create a supportive solution that helps them meet their deadlines without the excess stress and worry that would result from working with a less empathetic leader.
  3. Empathy can also help you manage conflicts more effectively. Heightened levels of emotional intelligence and active listening will help you gain a better understanding of the conflict at hand, the various perspectives at play, and the emotions that are being triggered as a result. Leveraging empathy and a coaching leadership style will help you acknowledge and validate the situation and other parties, align everyone to an agreeable goal, and navigate the conversation towards a resolution with ease.
  4. Citing another recent survey by Dayforce of over 8,700 employees worldwide, less than half surveyed felt their organization empathized with employees. If you’re an empathetic leader, you’re already in the majority, and will positively impact your team members. This same study by Dayforce shows that employees feel that empathetic leaders would lead to improved job satisfaction (52%), improved job performance (39%), increased productivity (37%), improved mental health and decreased burnout (48%), and making them more loyal employees (41%.)
  5. Lastly, we’ve reached a tipping point. The constant drive across all industries to do more with less combined with the bombardment of information, distractions, fire drills, change, and uncertainty is the main driver of chronic stress, burnout, lack of engagement, fatigue, loss of productivity, and a loss of focus. Organizations and individuals need to look towards new, innovative solutions and strategies to address these systemic challenges. It will require a multi-faceted approach that addresses the broken systems and empowers individual employees with the tools and resources necessary to navigate our new reality. Empathetic leaders who embrace the human side of leadership are best positioned to identify these new solutions as they are the ones who are truly and deeply listening to their teams and understanding the challenges that today’s workforce are facing.

Are there potential pitfalls or challenges associated with being an empathetic leader? How can these be addressed?

Left unchecked, or without a deep understanding of how and when to utilize empathy and compassion, there can be some challenges with being an empathetic leader. I see this most in people who label themselves as “empaths.” And while being an empath means that you can more deeply attune to other people’s emotions, it’s important to recognize that empathy is a skill, not a personality trait.

Empathy often comes at the expense of accountability.

There is a balance between having empathy and holding your team members accountable to meeting department goals and objectives. Empathy can help you understand what your team member is struggling with, so that you can effectively provide the tools and resources necessary to meet the department goals.

Empathy, without boundaries, can often lead to emotional exhaustion.

Being empathetic and attuned to the emotions of others doesn’t mean absorbing the emotions of others. As a professional coach, I have multiple conversations a day, many of which involve some heavy emotions. It’s a true skill to sit with my clients and provide them with the support they need in the moment, without absorbing their emotions. Heightened levels of emotional intelligence and strong emotional boundaries allows me to tap into the emotions they are feeling, help them feel seen and heard, and effectively partner with them to navigate the situation at hand, all while allowing me to shake off any icky energy at the end of the call, and be present with my next client.

Off-topic, but I’m curious. As someone steering the ship, what thoughts or concerns often keep you awake at night? How do those thoughts influence your daily decision-making process?

I can honestly say that I’m an excellent sleeper — so not much keeps me awake at night. However, the general thoughts and concerns that weigh on me surround the general state of how our society views productivity, busyness, and work. The constant push to do more with less, grow at unsustainable paces, and “keep up with the Joneses” is unsustainable.

I recently became a Certified Organizational Mindfulness Trainer and Facilitator because I firmly believe that bringing mindfulness into the workplace, and empowering leaders and individuals to develop and strengthen their mental and emotional toolbox will improve the quality of their health, happiness, relationships, and drastically improve the contributions they make to the organization.

As John Taylor, President and CEO of SHRM (Society for Human Resource Management), stated, “We’ve reached a tipping point in the workplace, driven by public attitude shifts on employment policiies, blurred lines between work and home life, and generational differences in the expectations of work itself. As working Americans challenge organizations to manage and lead differently, those that don’t will find themselves left behind.”

What keeps me up at night is that organizations are constantly looking for that next quick fix, and it’s right in front of them. It feels aloof and uncomfortable, but there are specific mindfulness applications and practices that have been scientifically proven to reduce stress, increase memory, improve focus, increase engagement, decrease distractions, improve self-awareness and emotional intelligence, drive productivity and more.

I use this knowledge every day to drive decisions about who I work with, what concepts I introduce to clients, and propose to organizations looking for leadership training and development opportunities.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

A movement to slow down and opt outside. The pace our society is moving at is unsustainable, and frankly, half the stuff we’re racing to complete are silly, stressful, non-fulfilling activities, so why is there so much urgency to complete them?

My movement would encourage people to slow down, smell the flowers, opt outside. It would encourage daily reflection, creating space for thoughtful and grounded responses, have an emphasis on “de-urgentizing” everything, digital detoxing, spending time in nature and hugging some trees.

How can our readers further follow you online?

The best way to connect with me is on LinkedIn, Instagram, and by subscribing to my monthly newsletter! I also post two to three blog articles per month on, which is a great place to go to learn more about many of the topics I discussed today and am passionate about! For anyone that is interested in partnering with me for leadership coaching, or group training and facilitation, they can contact me through my website, or book a complimentary exploration call at

Thank you for the time you spent sharing these fantastic insights. We wish you only continued success in your great work!

About the Interviewer: Cynthia Corsetti is an esteemed executive coach with over two decades in corporate leadership and 11 years in executive coaching. Author of the upcoming book, “Dark Drivers,” she guides high-performing professionals and Fortune 500 firms to recognize and manage underlying influences affecting their leadership. Beyond individual coaching, Cynthia offers a 6-month executive transition program and partners with organizations to nurture the next wave of leadership excellence.