How to Deal With Difficult Coworker/Sales Rep

I was in the process of making the company I worked for a lot of money. Like tens of millions in a short amount of time. I had made contact with a company in my territory and immediately established a good relationship with the decision maker, who just happened to live a mile away from where I grew up. I was also making a lot of contact with other companies we could potentially work and establishing relationships with them.

In comes my boss….here’s the new sales rep! He’s going to split the business with you!


I immediately viewed him as a threat and started searching for other jobs.

Then they made me train him. Not only were they giving him half of my territory, they were going to make me train the SOB?!?!

That’s when my attitude changed. It turns out he was out of a job due to the economy and wasn’t looking to step on my toes. He was also very good at selling and building relationships and I realized I could learn a lot from him.

It took a couple years before we became the friends we are today, but he and I still stay in touch even though we’re both at different companies and live hours away.

If you are having to deal with a difficult coworker or sales rep, first try to spend more time with them to see things from their point of view. Not just a 10 minute meeting a day….you need to go on a business trip with them or a long drive to visit a client.

Try this and give me feedback on what you found!


My First Flight in a Tiny Airplane

Before I became a pilot, I didn’t have a strong opinion on airplanes either way. They were interesting, but, like most people nowadays, I simply viewed them as a necessary evil/vehicle to get from A to B. I do, however, have the pleasure of remembering what it was like to fly before 9/11, but that’s another blog.

I became friends with a couple of customers and they were both pilots. And both of them talked about flying. A lot. I had never known a real pilot before in my life and was intrigued at how someone could have the balls to fly one of those tiny things around. Then he offered to take me for a flight.

It was an Aeronca Champ, similar to a Piper Cub, where you had to fold yourself to get in and the pilot sat behind you in a tandem seating arrangement. We bumped along in the grass and pulled onto the grass next to the runway. “Aren’t you supposed to be on the pavement?” I asked through the headphone mic….”Nah…the grass is softer.”

Taking off and flying in that Aeronca was a feeling that was tough to describe. If you’ve ever ridden a motorcycle a bicycle, picture yourself riding on the road and then suddenly leaving the earth. Even that doesn’t accurately describe how amazing it is to have a view of the treetops as if you were a Great Blue Heron lumbering along to search for some frogs.

We flew over some of the sites we mutually worked on, we flew over the golf course I played a bunch of times and flew up and down the road I commuted on nearly every day. Seeing all those things from the air made me appreciate the wonderful, rural, land I worked in and instantly gave me a new appreciation for my friend Larry. That flight also gave me a curiosity and passion for something I had never experienced before. That’s what flying will do…almost every flight in a small airplane enriches your life and is an amazing vehicle for making friends.

Larry and I continued to do business together and I would later keep him updated on my progress as I started my flight training. I moved away, but still run into Larry occasionally and I always make it a point to thank him for that first flight. That was a tremendous gift, and I’m not even sure he realized he gave me anything.


How to get more face to face meetings

I saw a contest on LinkedIn where two people working at the same company had a contest on who could set more face to face meetings….and the winner was the one who set 5 meetings for the next two weeks.

5 meetings in 2 weeks? Really? Is that a lot? As recently as last Wednesday I had meetings with three different companies on the same day and met with multiple decision makers from each company that day. My goal is at least two face to face meetings per day, every day.

Here’s what I tell my reps to do to get more meetings. And if they’re stuck, I’ll follow the steps below with them to show them it can be done.

The simple answer is, set a specific time every day to make calls to set meetings. I used to tell my reps to try setting appointments from 1:30pm-2:30pm every day. The decision maker is usually back from lunch and most people set meetings for the morning.

When you get the decision maker on the phone, introduce yourself then ask them for five minutes of their time to discuss doing business together and then LET THEM TALK! 95% of sales reps talk too much. At this point, when you let them talk they’ll usually find a time for you.

IF you don’t get the decision maker on the phone, my experience is leaving a voicemail is a complete waste of time. Occasionally setting appointments via email works, but it’s easier to set appointments when you’re talking to a live person.

What are your experiences with setting meetings?