What 50 Coaching Sessions Taught Me

by | Aug 5, 2025 | Sales Coaching

Opening the Conversation

Over the past few months, I’ve led over 50 one-on-one coaching sessions. During the 30-minute sessions we cover some general information before we dive into the specifics.

Depending on their Personality Style, I may even start with some small talk to get the conversation going.

  • How long have you been in sales?
  • Tell me about your career.

Establishing the Foundation: Personality Style

Next, I confirm their Personality Style as it becomes the foundation for our discussions so that they understand the connection in how their style plays into their sales approach in all aspects of the selling cycle.

Diving In: Strengths, Challenges, and Support

Then we begin the deep dive, taking most of the rest of our time together.

I ask them:

  • “What do you consider to be your strengths and can you give me some examples of using them?”
  • “Where would you like to improve,” which is typically the most in-depth discussion.
  • Finally, I ask, “How I can best support you moving forward.”

Interesting Patterns

There is a consistent trend with each style – their biggest concerns reflect and even matches their Personality Style.

It’s quite interesting, though not that surprising, that they want to improve the strength that this particular Style is known for. For instance, people with a Gold personality—known for their time management—are most interested in improving that skill. After all, time management is what is most important to the Gold.

But the Orange personality isn’t interested in this skill. Their priority is to brainstorm on what they can do to close the business more quickly, then close it!

The Pushy Perception: A Style-Based Blind Spot

Another trend I’ve seen relates to the Green and Blue Personality Styles. They worry about being too pushy when they ask for the business. In reality, they’re probably not pushy, but in their mind, they are, since they are generally the more patient and passive personalities.

Since Oranges and Golds are more aggressive, they have no concerns here, even though the person they’re selling to might think they are a little pushy. The Orange and Golds just don’t recognize that trait in themselves.

Using Strengths to Balance Weaknesses

What’s most important for each style is to understand the strengths of that Style, then leverage them to minimize a weakness.

So, for example, Blues and Greens that are aware that the customer is feeling pushed, they can use their strength of asking questions to get the customer’s perspective and respond accordingly. For instance, in closing ask: What do you believe would be best for solving your problem?

Tailored Support by Style

When I ask how I can best support them, Blues and Greens will ask for my opinions on moving a sale forward, while Golds and Oranges want insight on how to close the business.

Here’s to great selling!

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