Wanting to be liked is not a good trait for a CEO
Brian Halligan · How to be a CEO when AI breaks all the old playbooks | Sequoia CEO Coach Brian Halligan · Feb 15, 2026 · at 55:52
Brian Halligan (former HubSpot CEO and Sequoia coach) reflects on HubSpot's early over-emphasis on employee satisfaction over customer value.
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“Like wanting to be liked, I don't think is a good feature of a CEO and wanting to be the best place to work probably isn't the right way to go.”
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More from Brian Halligan
Halligan: Hiring McKinsey consultants into startups 'never works'
“The McKinsey one never works. It never works. It never works.”
HubSpot saw 100% attrition on hires from Google, Microsoft, and Salesforce
“Like we hired so many people from Salesforce and Google, Microsoft, like a hundred percent, you know, attrition rate on all those folks.”
Halligan: Starting a company has never been easier, scaling never harder
“It's never been easier to start. There's never been more competition. It's never been harder to scale.”
Halligan: Enterprise sales will be among the last white-collar jobs AI replaces
“But I think ye olde enterprise sales, where there's actual trust built up between two carbon based life forms, I think will be very, very, very late to go in the white collar world.”
Every knowledge worker and website will have an AI avatar by 2031
“I think every knowledge worker will have one of these in three, four or five years, but mine was more on the go to market side where I think every website will change and there'll be a, an all knowing avatar on that homepage.”
Halligan: Enterprise sales for AI startups hasn't changed despite the hype
“Honestly, the only thing that's different today, it's exactly the same as it's been for a hundred years, except they call their SCEs or their system consultants
For deployed engineers.
The rest of it is the same.
I thought it would be totally different in AI.
…”