When I am not a founder at a startup, the only times I am invited to talk to the Board is when something has gone wrong. Then the founders are trying to shift the blame on to me, rather than take the blame for their own decisions. And even though I want to talk to the Board, I avoid these meetings, because I don't want my first meeting with the Board to be dominated by the question "Why is your software behind schedule?"

This has been discussed on Hacker News before, but again, here are a few brief excerpts about how this relationship fell apart at a startup where I was at in 2015:

July of 2015

...All the same, a wave euphoria swept over John, which he communicated to the Board Of Directors. Much later, I learned that at this time they began to schedule their plans around the assumption that we'd be making significant money by September. Again, though I can admire a sales team that aims to hit aggressive targets, making such plans around a product that doesn’t yet exist, and which seems to be running behind schedule, is delusional.

August of 2015

...But Twilio would be a very dangerous step for us. If John and the Celolot Board of Directors really wanted us to ditch our iPhone app, this meant that we would be 100% committing ourselves to English as our only interface — and building a flawless NLP engine would be indispensable. There would be no buttons, no forms, nothing to click on. Just words and phrases written in English, submitted by innumerable users. And if we failed to build an NLP engine that could understand all of it, then we were doomed. I thought NLP was a fantastic supplement to traditional interfaces, but as a complete replacement, it was a huge gamble. It was like jumping out of an airplane without a spare parachute. Furthermore, if we had Hwan build us an app, then we could customize it in some really cool ways. Special messages, special ways of allowing data to be edited – things that are not possible with the standard iPhone Message app.

September of 2015

..."I am asking a hypothetical question." I thought this was obvious, but I was willing to emphasize the fictional nature of the scenario if it would calm him down.

"But why would you ask that?" The intensity of his reaction was as if I’d just asked him something obscene.

"Because I think hypothetical questions are important."

"I don't! I think working is important! Let's work hard and get this software running!"

"I’m sure we’ll get it working at some point, but we have already seen many unexpected delays." I pointed this out as calmly as I possibly could. "What if we encounter another?"

"If we miss this deadline, I'm going to ask you to talk to Milburn [of the Board]."

He threatened this as if it were the worst punishment he could imagine inflicting on me. Like, if the prisoner does not break during waterboarding, then we have them talk to Milburn.

"You don’t want to talk to him?" I treaded carefully. "You talk to him every day."

"No, you can talk to him about this."

I was wary. It sounded a lot like I was being set up to take the fall for John's bad decisions. A part of me very much wanted to talk to the board, just to be sure they understood the real situation. I wanted to warn them about Sital. I wanted to impress upon them the absolute urgency of the Conversation FSM. But I didn't want my first real conversation with Milburn to be dominated by the question, "Why are you running late?"

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excerpted from here:

https://www.amazon.com/Destroy-Tech-Startup-Easy-Steps/dp/09...