Category Archives: Coaching

Pipeline Deep Dives

I wasn’t that slow. (Photo by Luca Ambrosi on Unsplash)

When I was about 8 years old, we used to play “Blind Man’s Bluff” in my house. This is “It” tag, with the person who is “It” wearing a blindfold.

This was an extremely fun game to play indoors. Especially for me, who was nicknamed Steven “Turtle” Ainslie by my older sister because I ran too slow to catch her in regular Chase Tag. Continue reading


What Are They Gonna Do – Fire Me?

What my high school gym class was like.

Back in high school, my gym teacher would have us run outside every Wednesday – no matter what the weather was like. 

One morning in late December, we were out running and it was snowing like crazy. We must have had 4 inches fall in less than an hour.

For some reason,  my gym teacher decided it would be fun to finish our run by jogging into the inner courtyard of our high school singing Christmas Carols for all the students still sitting in classrooms.

We belted out Jingle Bells & We Wish you a Merry Christmas – off tune no doubt, but with great enthusiasm and volume. By the time we finished, every classroom had been disrupted. The students inside were all standing at the windows, laughing with (or at) us and cheering us on.

It was silly. But fun. It was hands-down the most memorable gym classes I’ve ever had.

As we jogged back to the locker room, I asked my teacher, “Aren’t you worried you’re going to get in trouble for doing this and interrupting all those classes?”? 

He laughed and with a big smile replied, “What are they gonna do – fire me?”

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Teach Your Reps to Not Undersell

As someone who grew up relatively poor, I don’t enjoy spending money and tend to be quite frugal. (Or, as my wife Ellen sometimes says, usually when I am wearing my favorite T-shirt, “Sometimes you are cheap to the point of being an embarrassment. You’re not going out with me looking like that. Go put on a nicer shirt.”)

Many times, when learning the price of something, I’d think to myself – I cannot believe anyone would spend so much money for that!

So you can probably understand that when I moved into the world of consultative technical sales, where deals ranged from thousands to millions of dollars, I had a lot to learn about money, perceived value, and business.

Fortunately for me, my customers and managers were more than willing to teach me.

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Dealing with Irrational Behavior

Sunbathing on the back deck

Every morning as the sun comes up, my dog Snickers likes to sunbathe on the back deck. Since I am an early riser, I let Snickers outside and start exercising, while my wife still sleeps.

In addition to sunbathing, Snickers is our self appointed Guardian of the Back Yard. She fiercely defends it from squirrels and other small intruders. Continue reading


Weekly 1-on-1s for Sales Reps – Set Goals, Make Things Happen and Cement Relationships

1 on 1 with Ziggy, my first dog.

I learned how important weekly 1-on-1s could be early in my career from one of my first mentors. He dedicated 1 hour every Friday afternoon to meet with me. During these meetings we discussed sales opportunities, challenges and areas where I needed his help.

I learned so much from him in these 1-on-1s that I still recall them fondly today, almost 20 years later.

It was in these 1-on-1s that I was also taught how to be a problem solver instead of a whiner.

I was complaining about how our Telecom Manager was delaying my installs because of his laissez faire attitude, which he expressed eloquently to me as, “Just relax Steve, the Telco will get installed eventually and the customer just has to wait until we get around to it.” 

After allowing me to whine about this for 5 minutes, my manager put his hand up and said

“Stop. From this point forward you can NEVER come discuss a problem with me again unless you bring ideas for how to solve it. We are in Sales, our job is to make things happen.

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