How do I (the CTO) Find Alignment with the CEO?

Not sure how to phrase things (or maybe I’m asking the wrong questions), but I’ll ask it anyway to at least get the conversation started.

On Feb 2, I joined as the CTO of a 2yr old startup that had very limited tech capabilities. On April 2, the CEO called me into his office and said to expedite an issue that we’ve been tackling for about 2 months now. I thought we were moving at a good pace but I guess I was wrong. That’s on me.

Then we came up with a plan to find an outside team and to outsource it. We executed the plan with constant communication and updates, we stayed nimble to the plan, picked two teams from our selection of 4 and started working on the project.

On April 16th, the CEO changed his mind, overrode my recommendations and said to go with 1 of the 4 outsourcing vendors (that did not make the cut).

How do I address this misalignment? How do I get the CEO’s “trust” so that I can start managing the technical risks instead of him managing it himself (he’s not techy btw)?


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