The Day I Became a Dictator

"We have arguably the best proposal platform around, but no way of helping people follow up and actually get the sale. We need to build something." 

Adam - Feb 2021

What followed that sentence was the 4 year realisation that a working democracy in a startup is a stupid idea, Silicon Valley's latest obsession "Founder Mode" is absolute bullshit, and essentially, you need to be a Dictator.

What you're about to read is a very real and raw account of someone who knew better, tried to do the "right thing", only to discover they needed to stop listening to opinions and find executers.

Reviving an old idea

This wasn't the first follow up system we'd built. Back in the day I'd designed a little green and red checkbox system with names down the left, stages along the top and you had to click all the buttons until everything was green. 

Cool little system. I wanted it in Better Proposals. 

So I drew it out, wrote it up, explained it over the phone and fielded questions from our then, Product Designer. She then went away with all my suggestions and came up with her own version. It was close enough to what I'd suggested to not warrant starting again, but it wasn't right. 

This is where I fucked up for the first of many times. 

Instead of changing the parts that didn't fit my original vision, I started changing the bits of my original idea that she'd kept, to make the other parts of her idea work. Big mistake. 

We spent months mucking about in Figma, never being truly happy but instead of declaring feature bankrupcy and just starting again, or getting pen and paper out myself, we just kept adding options, settings and conditions to make this absolute mess make just a little bit more sense. 

And after what we thought was a breakthrough, and with all the dots connected, the flow charts joined up I gave the green light to develop it. 

Fuck knows why. I'm a certified twat.

The first working version is "done". 

9 months later.

It's absolutely fucking shit. It makes zero sense. One of my conclusions at this point was that it was Figma's fault because you can't spot issues in Figma that you can in a browser. Partly true but it was still shit in Figma too. 

Speaking of things that take 9 months to build, honestly, anyone who's had a kid knows how absolutely fucking useless that child is when it's born. Being built for 9 months and it can't do anything. Just lays there screaming and shitting itself and can't even get you a beer or play catch. I'm serious when I say, a brand new child would have done a better job at following up with a lead than this thing.

Two full years pass

And in that time we potter about, come back to it, muck about with it and give it a break again just hoping and praying that one day it's suddenly going to click and all make sense. 

It never did. 

In the mean time, we added the concept of Doc Types within Better Proposals. Now, if you want to follow up with a contract or a proposal, you'd probably want to do that differently so we needed to factor that in too. 

Then we launched Onboarding. Well, you probably want to follow up with someone after signing so you can get payment and the form information you requested right? 

Every single thing made this project more and more complicated. 

Multiple people worked on it, looked at it, tried to solve the mounting number of logic issues with it. 

Nothing worked.

The Turning Point

Our original designer wasn't losing money, sleep or having any worries over the decisions to ignore me when I first tasked her with the job. None. 

Everyone else was just turning up, doing what the boss said in order to get it working. The commitment to the cause was helpful but ultimately cost somewhere in the $250,000 range. 

Eventually, if this all goes to shit one day, I'm going to be the one with my dick in one hand and absolutely no money in the other. Everyone else will have moved on, found other jobs and will be achieving success elsewhere. 

So, in the most selfish way possible, if I know I'm right, why should I give a shit what someone else wanted to do? Why do we do the "right thing" when we let people put their stamp on projects and alter a vision? Why is it the wrong thing to do to put your foot down and tell people how it needs to be? 

I had a vision. It was crystal clear and one shit decision at the beginning meant we spent over 4 years going back and forth getting absolutely nowhere. 

There was a moment. I can't pinpoint when it was or what I was doing but I remember thinking about what worked in the company and what didn't. 

It was all stuff I'd pushed through, designed, wrote and come up with that was working. And a lot of the stuff I had nothing to do with had fallen flat, or not been quite right. Not everything on either side but it was pretty clear that if I'd done things my way it had a much greater chance of success.

A founder has a unique connection with the idea, the product, the customers and the direction of the company. You can not outsource that stuff. Not a company like this where it's not decided by data, investors, advisors or surveys. 

Founder decisions are made with a gut feel. You have to stick to it.

Nudging a shit idea back on track

Sabrina and I sat down, no computer, no phones. Just chatted absolute waffle for a few hours and drew what we felt like this thing should always have been. Giving no regard for the effort in the past, just doing what was actually right. 

We made a massive feature, a tiny one. It's literally 1 screen and a setup page.

We just cut 80% of the pages, screens and options out of it that was only there because I didn't tell someone I wanted to keep my original idea. 

Devs did their thing and a month later it was give or take ready to go. 

It only took 4 years.

Learning a valuable lesson

My communication is absolutely shocking at times. You'll be reading this thinking I could easily have communicated my vision better, started over, collaborated more - yeah probably but sometimes you need to suffer in order to learn. 

The overall lesson for me is this: I either have no idea what I'm doing anymore, or, I actually do. 

If I'm full of shit, past my prime and no idea what I'm doing anymore then our staff can just go get another job and I'll just sit here in a cardboard box on Brighton Seafront asking for spare change.

If I do, and my team execute my vision, the company will do better, our team will do better (career and financially) and we will all be in a better place. 

And it looks like, at least for us that this is a much better approach. It's faster, people learn more and it keeps me more engaged with the company I started.

Adam
Chief Dictator of Better Proposals