We caught up with the brilliant and insightful Chris Rollins a few weeks ago and have shared our conversation below.

Chris, appreciate you joining us today. Alright, so we’d love to hear about how you got your first client or customer. What’s the story?

My very first client was referred to me by my former boss and mentor at the time. After I left my corporate job and told him about the coaching work I was focusing on, he connected me with someone he thought would be a good fit.

It was my first real lead, which turned into my first paid client.

“Well this is going to be easier than I thought!”

Boy, was I wrong.

The next dollar I made was about three months later from a workshop I hosted called “Your Path Built from Purpose: a framework, exercises, insights and action to help you forge a more meaningful path forward.”

It was a one-hour intensive workshop to help people get clear on their purpose, so they could be more intentional and aligned with their next career opportunity.

I priced it at $149. I thought if I could get 10 people to sign up, that would be ~$1,500, which sounded like a pretty good return on my time.

As the workshop neared, I wasn’t getting any signups. I offered a discount code to access it for $99, thinking people would be flooding in.

One person signed up.

She logged onto the Zoom at the top of the hour. It was clear by the look on her face that she wasn’t expecting to be the only one.

After explaining that she was the only participant and giving her permission to opt-out, she decided to stay. We got past the initial awkwardness and ended up having a productive session together.

At the time, it felt like a huge embarassment and failure.

But there was something validating about creating an exchange in value, even just with one person; a random stranger willing to pay $99 for my time and coaching to get clarity on a more purposeful career path.

I like to share this story because we all have to start somewhere. And little experiences like this teach you something and help shape what comes next.

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers.

After graduating college with a degree in Psychology, I was fascinated by the study and application of theories related to leadership, teams, company culture, etc. But I didn’t want to pigeon-hole my career in HR, and I wasn’t ready for grad school.

So with a fancy four year liberal arts education, I got a job in…sales.

I spent the next three roller coaster years in SaaS (Software as a Service) sales – prospecting, cold calling, sending cringeworthy emails, doing product demos and chasing monthly quotas that always seemed just out of reach.

The occasional quota-busting month distracted me long enough from my disdain for the job to keep going.

Three years later, I finally realized I needed to focus on work that honored my strengths: building relationships and trust with my clients.

I took a job as an Account Manager at a company I loved, which was more like 90% client service and 10% sales. This was my sweetspot.

My career took off.

After two years as an individual contributor, I had my first foray into management. I led the Onboarding and Customer Success function with 9 direct reports. It was a lot at once, and I did not feel prepared for the responsibility, but I was fortunate to have exceptional leaders supporting my growth along the way.

Two years later, I suddently had a seat at the exectuive table as SVP of Organizational Development.

It was the job I always wanted, but I had this sense that there was something more for me out there.

An acquisition/merger ushered in new leadership, and I saw first-hand how a single leader can have a ripple effect that quickly and drastically changes a company culture.

Some may say it was a positive change, others not so much. Either way, it wasn’t for me.

I now find myself almost 5 years into running my own business as a leadership speaker and coach, sharing my lessons learned in a passion- and purpose-aligned way.

In the current work environment, where trust is low, loneliness is high and our workforce is more distributed than ever, I help companies develop leadership that fosters connection, engagement and inclusion for their organizations.

My Ripple Effect Leadership™ framework takes a human-centered approach to building teams and cultures that move forward faster and bring everyone along.

I’m proud that as a certified LGBT Business Enterprise, my message has been able to connect with diverse audiences at companies like Raytheon, Walmart, Oracle, Clorox, ABB, Emerson, PNC, Raymond James, IKEA and so many more.

How’d you build such a strong reputation within your market?

Over the last four and a half years of running my own business, the focus of who I serve and what I offer has changed multiple times. Probably every 4-6 months.

First it was career coaching for unfulfilled job seekers. Then it was leadership coaching for mid-level managers navigating the uncertainty of their new responsibility. Then it was executive coaching specifically for HR leaders. Then I leaned into working with folks in the LGBTQ+ community, which led to the launch of the QueeHR community. Then I began leading virtual workshops and leadership trainings with companies. Now, I have a handful of select private coaching clients, but the majority of my business is speaking and workshops centered around The Ripple Effect – the brand and framework I’ve built to focus on leadership development with a heavy focus on inclusion. And most importantly, I meet people where they are so that the message is accessible, memorable and actionable for everyone.

So you might argue that this hindered my ability to build a solid brand or reputation. Despite all the shifts in focus and evolution of my business, through it all, I’ve done a good job of being genuine about who I am, what I’m up to, and how I can help others. In many ways, the development of my business and brand has been a direct reflection of the work I’ve done to get clearer and clearer about who I am, what I stand for, and what impact I want to have in the world.

I never really had a “brand strategy” or “marketing strategy”.

What I did know was that I wanted my business to be deeply aligned with who I am. Over time, I noticed people starting to comment on how much they loved the brand I was building.

Huh? What brand?

When I look back, it was just me sharing my story and journey in a genuine, consistent way.

I think the lesson here is to pivot your business all you want as long as you stay centered on your purpose and grounded in who you are.

We often hear about learning lessons – but just as important is unlearning lessons. Have you ever had to unlearn a lesson?

Early on in my business when I was focused on 1:1 coaching, I thought – let me build a group coaching program that focuses on developing new or first-time managers. I remembered the uncertainty and doubt I experienced taking on that responsibility for the first time, and figured other people had to be going through something similar.

So I spent weeks, maybe months, interviewing past colleagues and friends to see what their pain points were. Then I spent weeks designing an entire curriculum. Then I spent weeks figuring out what my “pillars” were to create a compelling framework for the program. Then I spent weeks building a landing page. Then I posted about it on LinkedIn expecting a bunch of people to sign up. Crickets.

There was a lot I learned from that colossal waste of time, but that main one was…

If you build it, they will not come.

Sell it, then build it, then you know they will come.

Contact Info:

• Website: https://www.chrisrollins.me/
• Instagram: https://www.instagram.com/thisischrisrollins/
• Linkedin: https://www.linkedin.com/in/christopherrollins/
• Youtube: https://www.youtube.com/watch?v=p0c-Rs0BNi8

Image Credits

MMG Studios
Wilson Media Co
Anna Avgoustis