- November 4, 2025
- Posted by: Dave Kurlan
- Category: Understanding the Sales Force

I didn’t take up golf until I was 50. As someone who played baseball (won a batting title) and tennis (ranked as a junior), I thought it wouldn’t be much of a challenge to hit a ball that was just sitting on a tee. What I didn’t know at the time was that hitting a golf ball flush would be the only sport that could provide me with the same rush I had when squaring up a baseball. I didn’t know what I didn’t know.
At the time, my golf friends probably couldn’t stand it when I bragged I was overshooting the greens. While I thought that was the equivalent of hitting a home run, they knew I had no idea where or how far the ball was going or which club to use. I didn’t know what I didn’t know.
I was so bad those first two years that I counted lost balls instead of strokes. I spent more time in the woods and the water looking for my stray balls than I did on the course. A four-putt was a win. While I could sometimes hit a ball straight and other times hit a ball in the air, the rare occasions I could do both were causes for celebration. I didn’t know what I didn’t know.
Speaking of not knowing a swing from putt, let’s talk sales.
Last week I role-played a discovery call with a new (to me) rep to demonstrate how to uncover compelling reasons to buy. I played the sales part and my first question was why he (playing the prospect) wanted to meet with me. He said he was interested in the software and I asked why. The rep stopped me and asked what I was doing. I said let’s keep going and then we’ll talk about it.
When we finished the role-play I asked the rep why he stopped at the second question. He said that he wouldn’t have asked another question so I asked what he would have done instead and he said that as soon as he heard his prospect was interested he would have sent a proposal. After the role play he realized what he has been missing in his sales calls. He had been in sales for six years and he didn’t know what he didn’t know.
This happens with salespeople who think they’re great, successful, impressive, capable, or a winner, if they simply:
- Book enough demos; Demos are fine if they are later in the sales process to show how you can solve the problem that you actually learned about.
- Send enough proposals; See demos! Fine if they are late in the sales process to formalize your recommendations.
- Get the company on bid lists; I can’t believe I still hear this. Getting on a bid list or an approved vendor list may be a required step but it never was, is not now, and will never be a win.
- Close a big deal; That’s great, but it can’t be a one-off, it must be a consistent, repeatable outcome.
- Hit quota; This should be a minimally acceptable outcome. It’s their job!
They don’t know what they don’t know.
Pivot to sales management.
Last week I coached a new (to me) sales manager and helped him understand how to coach one of his underperforming salespeople. I asked whether the problem was lack of accountability or lack of ability and he wasn’t sure. I asked if the salesperson was making the effort, making the calls, and meeting the requirements for daily activity. He wasn’t sure. I asked what the required activity was. He said there wasn’t any, that the only requirement was quota, and it didn’t matter how salespeople reached quota. I asked how many salespeople were hitting quota and he said none of them. As nicely as I could, I said, “You don’t have any activity or pipeline requirements, you don’t know if your salespeople have the skills, and none of them are hitting quota.” I gently asked, “What are you doing all day?” He said, “Selling.” He didn’t know what he didn’t know.
The enemy of being great in sales or sales management is when we don’t know what we don’t know.
The sales rep in the first example reports to the sales manager in the second example. Let’s move up one more level in the sales organization to the VP Sales.
Until last month, he was a sales manager for this company and in that role, he didn’t know what he didn’t know. But he did have a couple of capable salespeople who made him look good by consistently exceeding quota each quarter, so he was promoted. While he was fortunate to have those two strong salespeople, the company thought he was a rock-star and credited him for their achievements. In a senior sales leadership role, not only does he not know what he needs to know as a Sales VP, he doesn’t know what his sales managers need to know to perform in their roles and you guessed it – he doesn’t know what his salespeople need to know to become sales performers.
Fortunately, the new CEO suspected there was an issue and asked us to uncover the problem, fix it, create a proper sales culture, provide the required sales tools and train up the entire sales organization. Little did he know, the issues actually stemmed from flawed hiring practices, as they had historically emphasized engineers over salespeople. That led to an entire sales organization that were lacking in skills, understanding, sales process, strategy, methodology, tools, expectations, accountability, coaching, pipeline management and more.
Fortunately, the new CEO knew what he didn’t know. Feel free to reach out if you’re a CEO who knows what you don’t know.
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