At the beginning of my current job (I joined as CTO) I had to inherit a lot of misunderstandings that the management team had.

They had hired people who knew nothing about building software (before me joining), most likely those people have never really built and shipped anything. Everyone on the management was under the impression that software is easy and everything needs to be delivered on time and if it's delayed we need to throw more money at the problem and that would solve the problem. They would continuously ask for "timelines" and never understood the word "estimate". They knew the definition of the word but could never accept the reality of the definition.

I was tasked with building a brand new core banking engine and a kyc engine. I talked to the existing tech team that was there and none had ever done anything complex. Mostly they just knew how to write some basic PHP pages to do some simple tasks like rendering a CSV table for a specific report etc... So they needed to first be trained.

To cut a long story short I was the only one on the team to be able to write productive code to build such a complex system. I hired someone who could write code to help train the existing team. However given the complexity of the problem and the tight timelines I had to solve. I basically did the design and implemented about 70% of the code myself while my other teammates were being trained. This also included building a KYC engine along the way. I remembered suffering immensely building the engine and hiring / building the team. I would focus on working with the team during the day and coded at night, since that was the only time I could get un-interrupted hours to code.

I worked til 2AM almost every night for 7 days a week for over a year (6 months to get it to launch and then refinements / continuous improvements after). To complete the engine and get it to serve hundreds of thousands of transactions every month. I was never paid for overtime. Today the company stands strong with handsome profits.

Trust me. I can tell you, the problem is not the developers / process / agile / kanban / etc..., the problem is management. It's always management. I was able to get management to understand the true scope of the task by stopping working overtime and standing my ground (when the company had recovered and was able to produce a stable income to support itself).

The overtime I did hid away all the 'complexities' and the 'debt', and prevented the company from learning. I basically ended up paying for the company's mismanagement / toxic culture with my time. Fortunately a lot of toxic people left the company, a growing company will generally push out the non-performers organically. It took a lot of effort on my part personally to resolve issues plaguing the company, establish an engineering culture, build a strong tech team that can withstand pressure and deliver continuously and can build on top of the framework I provided.

The lesson has always been. It's never the software team (at least never the team I manage) whom are not productive or doing their best. It has always been management / company culture / never truly understanding the scope / requirement enough to understand how huge of an undertaking a given project is. I can tell you without a doubt this article pretty much hit the nail on the head. I'm living proof and have the battle scars to prove it.

Now I tell management about time estimates as it is. "No fixed timeline, the team estimate, the team builds, it's done when it's done, live with it or fire me."

I've fortunately afford myself the position to be able to deliver the truth serum to management and they have no choice but to accept it. It didn't come cheap, I'm still scarred.