Developer CEO vs Sales Guy CEO

I am a sales guy CEO. One quick look at my LinkedIn profile shows direct sales and partner sales and business development and marketing and sales management. The developers I work with tell me I am about as well versed in things technology as a sales guy CEO can hope to be - but I’m still a sales guy CEO.

This week I had the pleasure of meeting a developer CEO. He’s overseeing a rapidly growing startup that’s already raised multiple rounds of financing to go along with 1000’s of paying customers. We spent an hour talking opposite each other in a booth. 

After I left I thought “Hmm. He asked 80% of the questions and I asked 20%. What’s the significance of that?” So I thought about the conversation further. 

He had an appetite for data. He was curious to learn my thoughts around competition, markets, geographies, team structure around go to market etc. Generalized answers were great but specific answers were much better. Every time I thought he’d exhausted a line of questioning he had one more follow up. In short, he was (unsurprisingly) bright and relentless. I suspect in his mind the benefit of meeting was directly related to his perception of the quality of data in my answers. 

I, on the other hand, find myself answering questions and wondering “That’s a great question. I wonder why he asked that question? It’s interesting how that’s his follow up question. I wonder why he didn’t ask about x instead” I would observe his body language to mentally note when an area seemed to excite, agitate or bore him. I would wonder about the questions he didn’t ask. Most of my questions were “leader” questions. Generalized questions. My questions weren’t so important.  Where he took my generalized questions and drove them to specific topics - that was the interesting part. That let me know what’s on his mind.

Whereas he based the value of the meeting on the quality of the data I focus on how much I think I got an accurate snapshot of how the person thinks and operates. That will give me the context for assessing future activities by his company. Naturally I was also assessing the quality of his answers and he was probably making some observations about me separate to the content of my answers. Still, I was struck by the unique styles we had.

There’s no doubt his style and approach is working really well. It did make me wonder if the best leaders are capable of doing both. I started wondering about the leaders I admired most (at the macro and micro level) and backing into how they approach a new encounter. 

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