Today we’d like to introduce you to Jenn Masse.
Hi Jenn, can you start by introducing yourself? We’d love to learn more about how you got to where you are today?
I am a Certified Leadership Coach, Leadership Development & Organizational Mindfulness Facilitator, and Certified Forest & Nature Therapy Guide. I work with leaders and organizations to help them lead more effectively without burning themselves or their teams out.
Like many ICF-certified leadership coaches, I got my start in the corporate world. I spent over a decade working across accounting, project management, sales, marketing, and business development, always chasing the next role, the next promotion, and what I thought success was supposed to look like.
On paper, I was doing really well. But underneath that, I felt underutilized, undervalued, and honestly, pretty empty. I kept thinking the next role or opportunity would fix that feeling, and it never did.
The turning point came when I found myself sitting in my boss’s office, crying in a way that made it impossible to keep ignoring what was going on. It was one of those moments where you realize something has to change, and more importantly, that you’re the one who has to change it.
The next day, I enrolled in an ICF-accredited coaching program. That was in 2018, and over the following eight months, I experienced firsthand how powerful coaching can be. It changed how I think, how I show up, and how I lead. By July 2019, I had earned my first of what is now eight coaching certifications, left my corporate role, and launched my coaching practice, Conshy Coaching.
I haven’t looked back since.
Would you say it’s been a smooth road, and if not what are some of the biggest challenges you’ve faced along the way?
Absolutely not. We tend to skip over the messy middle of building something, and I’d be lying if I said this has been a smooth journey.
The first real challenge was one I didn’t expect. It wasn’t until I left corporate that I fully recognized how toxic that environment had been for me. I needed space to focus on my own mental health and well-being before I could fully show up for my clients. That process took a few months, and while it was necessary, it wasn’t easy.
Then, the pandemic hit. Most of the groundwork I had been laying through in-person networking events, speaking engagements, and corporate trainings disappeared almost overnight. Organizations paused or canceled contracts, budgets tightened, and there was a lot of uncertainty around what leadership development even looked like at that moment.
On the private coaching side, I had to pivot quickly to a fully virtual model. At the time, it felt like a major disruption. In hindsight, it ended up being one of the best shifts I could have made. My clients embraced it, and it’s still how I work with most of them today.
Beyond those early challenges, one of the most important shifts in my work has been recognizing that the problems leaders bring to me are rarely technical. They’re adaptive. They involve letting go of control, having difficult conversations, shifting long-standing patterns, and moving from being the person who solves everything to the leader who builds teams that can think and act independently.
As the pace of change has accelerated, so have the needs of my clients. When I started in 2019, conversations around AI, constant digital input, and attention fragmentation weren’t front and center. Now, they’re impossible to ignore. At the same time, I’ve seen more leaders feeling disconnected from themselves, from their teams, and from anything that helps them reset outside of work. That directly impacts how they think, make decisions, and lead.
Because of that, my work has continued to evolve. I’ve spent a significant amount of time studying the science behind attention, emotional regulation, and energy management, so I can meet my clients where they are. It’s pushed me to go deeper, not just helping leaders solve problems, but helping them fundamentally change how they think, operate, and lead.
As you know, we’re big fans of Conshy Coaching. For our readers who might not be as familiar what can you tell them about the brand?
Through my practice, Conshy Coaching, I partner with leaders and organizations who are ready to move away from outdated, rigid ways of leading and toward something more human and sustainable. At the core of my work is a simple idea: mindset shapes energy, and energy drives impact. When leaders understand and manage both, everything from decision-making to communication to team performance starts to shift. In practice, that means helping leaders reduce decision fatigue and emotional overload so they can think clearly, communicate with intention, and lead more effectively.
I do this through a combination of one-on-one coaching and customized workshops, where we focus on real, day-to-day leadership challenges like navigating change, improving communication, increasing ownership and authority, and making confident decisions in complex environments.
A big part of my work is with women leaders, especially those who have spent years over-delivering and over-functioning. They’re successful, but they’re exhausted. Helping them redefine success, trust themselves again, and lead at a high level without burning out is some of the most meaningful work I get to do.
What really sets my work apart is how I approach coaching. While I’m ICF-certified and grounded in those professional standards, I don’t take a passive or purely question-based approach. Most of the challenges my clients bring are not technical; they’re adaptive. They involve shifting long-standing patterns, having difficult conversations, letting go of control, and stepping into a more strategic leadership role.
Because of that, I bring both structure and perspective into the work. I integrate science-backed mindfulness and neural training strategies, along with assessments like the Energy Leadership Index, CliftonStrengths, and Positive Intelligence, to give clients a clear understanding of how they’re currently operating. From there, we don’t just talk about insights, we apply them directly to the real situations they’re navigating.
I also believe leadership should feel sustainable. Many of my clients come to me already stretched thin, and initially worry that coaching will be one more thing added to their plate. However, our sessions quickly become a non-negotiable space in their week where they can step back and think strategically.
One client described it as feeling like they were stranded in the middle of the ocean, only to realize they were actually standing in the shallow end of a pool. That shift in perspective is often what allows everything else to change.
What I’m most proud of is the impact and consistency of the work. The majority of my business comes from repeat clients and referrals, which tells me that what we’re doing is not only effective but sustainable.
In terms of offerings, I provide:
• One-on-one coaching engagements that include assessments, a strategic roadmap, and ongoing support
• A core insights package for leaders who want clarity and direction without a full coaching engagement
• Custom leadership trainings and workshops for organizations across corporate, nonprofit, and public sectors
• Partnerships with colleges and universities
• Nature-based leadership experiences and retreats that support reflection, recovery, and clearer thinking
Is there a quality that you most attribute to your success?
Three qualities have had the biggest impact on my success: authenticity, curiosity, and perceptiveness.
Authenticity is foundational to how I show up in my work. I don’t believe there’s one “right” way to lead. There are plenty of systems and frameworks out there, but ultimately, each leader has to find what works for them, their team, and their environment. My role is not to fit someone into a model, but to help them develop their own.
I also don’t pretend to be anything other than who I am. Whether I’m in a hoodie or a blazer, I show up the same way: direct, grounded, and human. That authenticity creates trust, and it allows my clients to be honest about what’s actually going on so we can do meaningful work.
Curiosity has been equally important, and it is something I had to learn the hard way. Earlier in my career, I was focused on being right, having the answer, and moving quickly. That mindset limited my growth, created unnecessary pressure, and ultimately contributed to burnout.
Letting go of the need to be right and shifting toward curiosity changed everything. It allows me to stay open, to continuously learn, and to meet my clients where they are instead of where I think they should be. It also makes me a better coach, because I’m not trying to solve their problems for them, I’m helping them think more clearly so they can find their own solutions.
Perceptiveness is the third piece, and one that I’ve come to appreciate more over time. As someone with ADHD, my brain doesn’t always move in a straight line. What used to feel like a challenge has become a strength in my work.
I’m able to follow nonlinear conversations, pick up on patterns, and connect dots that aren’t always obvious. Clients often come in talking about one issue and end up uncovering something deeper that’s actually driving it. One of the things they consistently tell me they value most is when I pause and say, “Here’s what I’m hearing,” because it helps them make sense of what felt scattered and see their situation from a new perspective.
Those qualities also shape how I work with my clients. I’m not interested in surface-level conversations or quick insight without action. The leaders who get the most out of this work are willing to be honest about what’s actually going on, take ownership of their role in it, and apply what we discuss between sessions.
Most of my clients are already highly capable and experienced, but being qualified isn’t always enough to lead effectively. What creates real change is the willingness to challenge long-standing patterns, have the conversations they’ve been avoiding, and lead differently when it matters most. Clients don’t come to me for motivation. They come for traction, clearer thinking, better decisions, and a way of leading that actually feels sustainable.
For those who are curious about what this could look like in practice, I offer complimentary exploration calls. It’s a space to step back, talk through what’s currently feeling challenging, and determine whether partnering together would be the right fit.
Pricing:
- Pricing varies depending on the level of support and scope of engagement. 1:1 coaching engagements are customized based on the client’s goals and typically include assessments, a strategic roadmap, and ongoing coaching support Organizational trainings and workshops are scoped based on size, format, and objectives I also offer a core insights package for leaders who want clarity and direction without a full coaching engagement For more information, I encourage people to reach out directly so we can determine the right fit.
Contact Info:
- Website: https://www.conshycoaching.com
- Instagram: https://www.instagram.com/conshycoaching/
- Facebook: https://www.facebook.com/conshycoaching
- LinkedIn: https://www.linkedin.com/in/jmasse/
- Youtube: https://www.youtube.com/@conshycoaching/videos
- Other: https://forestbathingcentraloregon.com/
Image Credits
Amanda Iris Photography, Nichole MCH Photography, Jenni Fritz Photography
