Speaking Directly When No One Else Will

Hi {{first_name|there}},

This week is about candor, and who in a company is actually free to practice it. On the Chief of Staff Podcast, Kartikeya Jaiswal of Bifrost AI makes the case that most roles hold the privilege of not speaking directly, and that a Chief of Staff gives it up.

Plus Connect New York in October, and the events filling out your fall.

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COS Fellow, Tristan Lim, recorded this one at the Bifrost AI office in Singapore. Kartikeya Jaiswal has spent six years in the CEO’s office across two startups, and he opens by demoting the two traits everyone in this role agrees on.

Ask a room of Chiefs of Staff what makes someone good at this job and you get a mix of responses about high agency and high compassion. KJ accepts both, then moves them down the list. Agency is essential, compassion is table stakes, and what actually separates people is the ability to speak respectfully, directly and bluntly at the same time. His reasoning is about information flow. Employees manage up. A prospect who passes gives a generic reason. An investor who declines gives a generic reason. By the time any of it reaches the founder, most of the signal has been sanded off.

What makes that survivable is a conversation he had before he needed it. Bifrost's founders ran him through eight interview rounds over eight weeks, and somewhere in round three the CEO asked him what kindness meant to him. That question was doing real work. They were hiring for a relationship where disagreement is the point, so they screened for how he would deliver it. The agreement that came out of those eight weeks is what lets him say the hard thing now without spending the relationship to do it. If you have never had that conversation, his advice is to ask your founder how they want to be disagreed with, before the first time you need to.

👉 Listen to the episode

Two days in New York on October 22 and 23, built around the shift this week’s episode keeps circling. Moving from amplifying a leader behind the scenes to owning the systems, programs, and operating models that produce the outcome. Sessions on architecting operating models that scale, and on the judgment that holds up when things get complicated.

October 22 and 23, 151 West 42nd Street.

That’s it for this week. If you have never had the disagreement conversation with your principal, KJ’s episode is a good excuse to put it on the calendar.

Scott