What Running My Own Business Taught Me About Sales — And About People

Before I was coaching sales leaders, I was one.

And before that, I was out in the field every day — selling, installing, and servicing equipment for business owners across Ontario. No big corporate safety net. No marketing team generating leads. Just me, my truck, my tools, and a belief that if I did right by people, the business would follow.

That chapter of my career taught me more about sales — and about people — than anything I’ve read in a book or learned in a training room.

Here’s what I took away.

Honesty Isn’t a Value. It’s a Strategy.

When you run your own business, you can’t hide behind a brand. You are the brand. Every promise you make, you have to keep. Every mistake you make, you own personally.

Early on I learned that the fastest way to lose a customer forever was to tell them what they wanted to hear instead of what they needed to know. And the fastest way to keep a customer for life was to tell the truth — even when it was uncomfortable.

If a piece of equipment wasn’t right for their application, I said so. If a repair was going to take longer than expected, I called before they had to ask. If something went wrong during an installation, I owned it immediately and fixed it at my expense.

That level of honesty felt risky at the time. In practice, it was the best business development tool I had. Because customers who trust you don’t shop around. They call you first, refer you freely, and stay with you for years.

Honesty isn’t just the right thing to do. It’s the smartest long-term sales strategy there is.

The Standard That Built My Reputation

I had one rule when it came to equipment installation and service:

Never leave a piece of equipment in a state I wouldn’t leave it in my own living room.

That meant every job was finished properly — not just functionally, but presentably. Every machine was clean. Every connection was secure. Every setting was calibrated. I didn’t leave until the customer was satisfied and everything was running the way it should.

That standard cost me extra time on some jobs. It never cost me a customer.

Word travels fast in tight-knit dealer networks and trade communities. When people knew that I wouldn’t leave a job site until it was right, they stopped worrying about the outcome and started trusting the process. That trust turned into referrals. Those referrals turned into territory. That territory turned into a business.

Standards aren’t overhead. They’re marketing.

The Principle That Changed Everything

Somewhere along the way I came across an idea that reframed everything I thought I knew about sales:

Help enough people get what they want, and eventually you will receive what you want.

I’ve seen this principle dismissed as soft or idealistic by people who haven’t tested it. I’ve also seen it work, consistently, over 15+ years in some of Canada’s most competitive sales environments.

When I stopped thinking about what I needed to close and started thinking about what the customer needed to solve — everything changed. My conversations got better. My close rates went up. My referrals multiplied. And the work became more meaningful, because I wasn’t just moving product — I was actually helping people.

The shift sounds simple. In practice it requires real discipline, especially under quota pressure. Every instinct in a tough month is to push harder, pitch louder, and close faster. The top performers I’ve worked with do the opposite — they slow down, ask better questions, and focus more intently on the customer’s problem.

That’s not weakness. That’s the highest form of sales intelligence.

What This Taught Me About Coaching

When I transitioned into sales leadership and eventually into coaching, I brought these principles with me.

The best coaching I can offer anyone isn’t a framework or a script. It’s a mindset shift — from selling to serving, from managing to developing, from hitting this quarter’s number to building something that lasts.

The leaders I work with who make the biggest leaps aren’t the ones who needed the most technique. They’re the ones who committed most fully to these fundamentals:

• Tell the truth, especially when it’s hard

• Deliver more value than anyone expects

• Put the customer’s outcome ahead of your own agenda

• Play the long game, even under short-term pressure

These aren’t coaching concepts I invented. They’re lessons I learned the hard way, in the field, running my own business, earning trust one customer at a time.

Why I Coach

I coach because I’ve lived both sides of this.

I’ve been the rep who was so focused on the sale that I missed what the customer actually needed. I’ve also been the leader who figured out that service, honesty, and genuine care for people isn’t just good ethics — it’s good business.

That gap — between knowing what works and actually doing it consistently — is exactly where coaching lives. And closing that gap, for sales leaders and business owners across Ontario and Canada, is the work I’m most proud of.

If any of this resonates with where you are right now, I’d love to have a conversation.

Chad Richardson is a sales leadership coach and consultant based in Ontario, Canada. With 20+ years of experience leading sales teams across automotive tools, equipment distribution, and dealer channel networks, he helps business owners and sales executives build teams that perform — not just occasionally, but consistently.

Book a free discovery call and let’s talk about what’s possible for you or your team.