My Leadership Journey: When My Style Clashed with Expectations (And How “Selling With Dignity” Became My Compass) By Harry, Author of “Selling With Dignity”
As many of you who’ve read “Selling With Dignity”—or have gotten to know me—recognize, I believe deeply that selling is, at its heart, about serving others. It’s about solving problems and showing genuine care for people. The money, when we approach our work this way, naturally follows. But what happens when this service-first mindset, this commitment to dignity, clashes with the traditional expectations of sales leadership? I want to share a bit of my own story – a journey from sales performer to leader, filled with its share of stumbles, missteps, and ultimately, clarity.
From Star Performer to Questioning Leader: The Early Days
Like many, I was promoted into sales leadership after a period of doing quite well as a salesperson. I tried to model my early leadership style on one of my previous managers – someone fun, bright, helpful, and knowledgeable. His approach resonated with the principles I hold dear: humor, storytelling, and doing the right thing were all traits that fit me well.
However, like many endeavors in life, I didn’t fully grasp what I was getting into. To give you an idea, I’d always had a lot of fun dealing with clients and truly enjoyed my selling career. I even had a great client who affectionately called me “Happy Harry.” That fun-loving, “Happy Harry” was in for a shock and was about to gain a whole new understanding of stress.
The new team I was assigned to lead operated differently than I did. They were all very new to sales and needed constant direction. Where I was creative, a self-starter who learned through trial and error (and by devouring wisdom from greats like Brian Tracy and Og Mandino), my team seemed to depend on their manager for nearly everything. I saw folks who were “in sales” but, in my mind, had a way to go before becoming true sales professionals. The critical importance of hitting sales targets, the seriousness of quotas, forecasts, and the act of actually selling—not just holding a “sales job”—hadn’t fully registered with this young team yet.
My dream of actively coaching reps in the field quickly collided with the wall of sales forecasts and performance metrics. It was a stark contrast to instinctively knowing where my own business came from. Seeing the team struggle, often confusing quotas with realistic forecasts only to miss targets significantly, was a frequent “Yikes!” moment. Added to this were the pressures of headcount, managing underperformers, and building a “bench.” I quickly found myself wondering, “What did I get myself into?” The stress was mounting; this was a public company, and numbers mattered. I felt completely in over my head. (A little secret between us, perhaps, but a very real feeling at the time!)
The “Closer” Conundrum: A Clash with My Core Values
One of the biggest challenges was the expectation that I transform from a coach into “the closer.” This was way out of my comfort zone. My passion was to help my team develop, to empower them to ask for the order confidently, not to be the manager who swoops in when things get tough. Trying to close business for someone else felt awkward, especially when every deal seemed to carry an almost life-or-death weight. Attempting to close deals where the buyer clearly wasn’t ready was often futile. As I state in “Selling With Dignity,” it’s when salespeople (or their leaders) prioritize their own self-interests that a sale becomes less than dignified. This pressure felt like it was pushing me in that uncomfortable direction.
After a year filled with bumps, bruises, humiliations, and what felt like near-death experiences (a slight exaggeration, I suppose!), I was enrolled in management training. There, I learned that the best managers were actually great coaches, focusing on developing people over merely chasing deals. This aligned beautifully with my belief, echoed by ancient wisdom: “There is more happiness in giving than in receiving.”
Demotion, Detours, and the “Drill Sergeant” Mistake
Despite this insight, my track record for that first year wasn’t stellar, and a demotion followed. I went from managing eight people to four. It certainly stung, but change, I was rapidly learning, was a constant in the sales world. My new role had me reporting to a General Manager who sometimes adopted a “drill sergeant” persona—yelling at reps was a somewhat normal, if unsettling, occurrence, and surprisingly, it sometimes seemed to yield short-term results. In a moment of trying to find my footing, I thought, “Why not try it?” I can still vividly see the look on the face of one of our newer sales reps as I berated him in the sales bullpen. That was a profound mistake. Attempting that style sent chills down my spine; it was so contrary to my belief that dignity and respect are paramount—as Richard Branson advocates, to help people thrive. It was clear this wasn’t leading with dignity; it wasn’t me. Or was it a momentary, regrettable lapse?
Finding My Way Back to Service and Dignity in Leadership
Through all this upheaval – the missteps, the pressures, the moments of self-doubt – we still sold quite a bit. We are often our own harshest critics, and looking back, I suspect our performance wasn’t as terrible as it felt through the lens of my own self-criticism. Having a proper ramp-up period to hit targets would have been ideal, but the reality is, it was an intense learning experience—akin to being thrown in the water to learn how to swim.
I clearly realized that leading from a place of stress was unsustainable. True leadership, like true selling, had to come from a place of positivity and genuine care for others. As I learned in my earlier mission work and emphasize in “Selling With Dignity,” if you desire to truly serve, to put others first, success will come. My past as a missionary had taught me how to serve and take care of people, and that, I understood, had to be my differentiator in leadership too.
Have there been times I’ve fallen short, even years later? Absolutely. We are all human. Forgiving ourselves and recognizing that we aren’t always on our ‘A’ game is an essential part of the learning process.
Leading With Dignity: My Commitment Moving Forward
Selling With Dignity® is about putting service to others first; it’s about knowing that this approach will ultimately lead to sales and allow you to sleep soundly at night. This philosophy is just as critical in leadership. My desire today is to lead from that very place of service.
This journey, with all its twists and turns, solidified my conviction. I’ll be sharing more of these experiences and the lessons learned in future articles right here. My goal is to help you, too, find ways to navigate the pressures of sales and leadership while upholding your integrity and fostering an environment of dignity. I hope that by sharing these modern-day parables, we can all learn to lead better.
I’d be honored to hear your stories as well. After all, life is about improving and striving to be the best version of ourselves.
Next up, I’ll explore a massive shift in my thinking that truly transformed my leadership: harnessing the incredible power of positivity.
Harry Spaight is a sales leadership coach and author of Selling With Dignity. He equips organizations to develop sales leaders who inspire and empower high-performing teams.