Everyone wants to look like they've got it all together in the workplace. That's why, for years, Ashley Holmes has been taking her team off-site for an annual retreat. "This is when we get to talk about the hard stuff."

Ashley's approach to leading and nurturing her team might be a bit unconventional at times. Still, she's proven to even her most reluctant team members that personal development has a profound professional impact. 

This year, she stumbled into a connection with Dave Inglis at a conference she was attending. "We struck up a conversation, and I felt an instant values alignment. When I asked what insurance brokerage he was from, he said he was actually one of the speakers for the event." 

During Dave's talk about being the CEO of your own life, a lightbulb went off for Ashley. 

"I knew from my own journey that no matter how hard you focus on your career, if you don't do the work on yourself outside of the office you won't get where you want to go. I hadn't heard someone talk about it the way Dave did." 

The ethos he shared was exactly what she aimed to impart to her team. It wasn't long after the event that she reached out to invite him to be a part of her team's next retreat. What followed was an in-depth process of customizing Dave's work to suit Ashley's dynamic team perfectly. 

Initially, Ashley expected Dave to show up and deliver a talk that was more or less the same as what she'd witnessed at the conference, and she was thrilled about that. However, over the course of a few exploratory calls, Dave dug into the workplace culture, team motivators, and personalities on Ashley's team. He suggested pivoting their focus in a new direction. Her excitement grew. This would resonate even more fully with the needs and goals of her team. 

"I spend time deliberately creating opportunities for conversation where transparency, humility, and vulnerability are welcome. These are the times we get to feel and be all the things we may not want to show up as in the workplace."

The day Dave arrived to meet her team, Ashley sensed a little apprehension in the room. "If we're going to a work event that is focused on work, my team knows how to prepare for that. When I tell them I'm bringing in a speaker to dive into the personal development side of things…they know they might get uncomfortable and be asked to participate in unfamiliar exercises. In the end, though, they know that the awkward things I ask them to do end with big rewards."

Delivering on her promises is one of the ways that Ashley builds trust and emotional rapport with her managers. So, when Dave asked to join the team for dinner before his talk, she was all-in on the opportunity for connection. While there might have been some hesitation at first from team members wondering who Dave was and what was going on—tensions quickly melted as he asked thoughtful questions and shared some vulnerable things about himself. Ashley was impressed, "Even through these natural conversations everyone was enjoying, I saw how Dave was getting to know the team and looking for ways to make his talk even more impactful and personal."

"Dave approaches leadership coaching holistically. Leadership is a state of mind, not just a role we have in the workplace."

Sherry Zimmer, CAIB CPIB

Commercial Lines Manager

The engagement during Dave's session was unrivaled. The activities he brought to foster self-awareness were easy for even the most logical team members to participate in. Each assessment and process evoked reflection without going directly into everyone's emotions. The results were tangible takeaways that left more room for individual discovery. 

"Goal setting can sometimes feel very abstract and overwhelming, but Dave's session made it much easier to really zero in on what I am personally trying to achieve. 

It definitely made me reframe the way I think about what is and should be important to me and how to actually reach goals that I set."  

Alana Teteris, CAIB

Underwriting & Compliance Manager

Inside the safe space Dave created, everyone had a chance to notice areas of their life that needed improvement, recognize their responsibility in making change, and start building a doable plan to get where they want to go personally and professionally. One of Dave's biggest gifts was making everyone feel open and encouraged to share. Even in this corporate setting, no one felt intimidated or uncomfortable. 

"By the end of the session, everyone had something to share that they were surprised about. Some people didn't realize they weren't paying attention to their partner, communicating clearly, or prioritizing their health." 

"Not balancing 'Health, Wealth, and Relationships' in my life has greatly impacted my ability to find success and calmness until I started addressing them head-on. 

Dave's advice put me on the right path and I can pass this on to my team when they feel overwhelmed and are unable to see a way out."

Bryan Crouch

Sales Manager

Ashley believes that the key to being a great leader isn't so much being one thing as it is being the one thing the person in front of you really needs. And somehow, Dave managed to be just what each person needed on their team retreat. 

Not only did the PetleyHare team leave with a deeper understanding of how to grow their bandwidth to be the people they want to be in the workplace, they learned that within themselves, are all of the resources they need to be powerful CEOs of their own careers, families, and lives. 

Article Written By:

Steena Maria