I then made the mistake of thinking that I would also have the same kind of fun as an employee. I became the tech lead at a startup, thinking I would have the kind of freedom that I previously had. This was a mistake. I was very excited about the technology that this startup was working on, but in the end I found, these jobs are much less fun, if you are not the founder, because there is a lot of pressure that comes from up above you, and when you come up with what you think is a great idea, you don't get to implement it. And there are additional frustrations: for instance, on this project I came to believe that it was crucial that we fire our initial data scientist, but the top leadership refused to fire him. This was a major roadblock that I would not have faced if I was the founder, as I would have had the authority to fire someone if I was the founder.
For anyone interested, I wrote in great detail about the experience here:
"I mean, essentially it's a command line interface with a wonky input method, no?"
This is precisely the feedback we got from salespeople, when we were working on a Natural Language Programming interface for Salesforce. Initially, I got angry and denied the comparison. But after several people made the same comparison, I came to appreciate how true it was. Unless NLP is perfect, it is really just a Command Line Interface with an awkward input device. I talk about this a little towards the end of this story:
When you have a bad project manager, good software will not save you. This is my personal story of how things can go wrong:
At 2 PM we had a meeting scheduled to go over all of the tasks in PivotalTracker. John had promised Milburn that we would execute our work according to a project-management philosophy that the tech industry called agile. Agile software development, among many other aspects, focuses on the delivery of small, incremental improvements to software. It encourages self-organizing teams, evolving and continuous progress, and rapid response to challenges faced. The Celolot team would work two-week sprints, checking in at the end of each period to see where everyone was at.
Unfortunately, vague definitions of “done” haunted our progress. John read through a long list of tasks that had been assigned to Sital.
“Find all possible variations of ‘Close Date,’” John read from the screen. “Is this done?”
“Yeah,” muttered Sital. “Sure.”
His assurance meant nothing to me. Sital would never lie, indeed I was often surprised by his childlike honesty, but he lacked an appreciation for the many ways that software could break.
“How many variations have been tested?” I asked.
“Two,” replied Sital.
“That’s not enough,” I said.
“That’s enough,” countered John. “‘Close Date’ and ‘Contract.’ That’s all we need.”
“What about ‘Close’?” I asked.
“Oh, yeah,” John thought aloud. “What about ‘Close’?”
“I’ll see,” Sital responded somewhat robotically.
John marked it as done.
“Wait,” I objected. “That is not done.”
John turned back to Sital. “Do you think you can finish today?”
“Absolutely,” Sital assured us.
“Then I’ll mark it as done,” said John, returning to his screen.
“But it’s not done till it’s done,” I argued.
John pondered this for a brief moment. “It’ll be done today,” he shrugged. He marked it as done.
In my view, John’s casual use of the word “done” to refer to items that were nowhere near done meant that this whole effort to track tasks was a useless ceremony. But John felt good about it. He could tell Milburn that we were following a two-week sprint, just like an authentic agile team.
It was true we had the accoutrements of an agile team. We used PivotalTracker. We broke down goals into fine-grained tasks. We reviewed the task list once a week, and we added more tasks every two weeks. But the whole thing was mockery of what the Agile Process was supposed to accomplish. If you have programmers who cannot finish assignments, then there is no point in pretending to be making progress.
related to here:
Every industry has certain euphemisms for the least savory aspects of its business. In sales, there is the secretly ugly phrase, “goal-oriented.” That sounds pleasant, doesn’t it? If I point at a woman and I say, “That entrepreneur is goal-oriented,” then you probably think I am complimenting her. But if I point at her and say, “That entrepreneur is a lying, manipulative, soulless psychopath who brutally exploits labor from the eleven-year-olds she employs in her sweatshops in Indonesia,” then you probably think I am insulting her, unless you are a libertarian. And yet both statements mean about the same thing: that she is someone who is willing to do whatever is necessary to ensure the success of her business.
When I read about Milburn online, I’d seen testimonials from his colleagues in which he was often described as a goal-oriented salesperson. That probably meant that he was a master of manipulating other people’s emotions. He knew all the tricks: praise, shame, laughter, anger, promises, guilt, threats.
Whether his use of these tools was conscious or unconscious is, of course, unknowable. But it doesn’t matter much. A lifetime as a sales professional left him with an arsenal of psychological ploys that had become second nature to him.
...Milburn truly had a genius for the strategic use of anger. If he sensed the risk of losing control of the conversation, he would indulge in another outburst. If I were to ever switch over to the Dark Side, I would want to study with him. His techniques were fundamentally dishonest and manipulative, but that is probably what made him so good at sales. And his tactics were probably an effective way to drive a sales team, but I sincerely believed that such tactics were the wrong way to run a software development team. Especially when doing something cutting-edge original, like we were doing, I think open and honest communications were extremely important. (I have worked with many companies where the sales team was both friendly and successful. One does not need to use abusive tactics to have success in sales. Indeed, the sales manager who relies on abuse is typically more interested in aggrandizing their own success, rather than the success of the company they work for.)