“Never give up!” they say… but we know that’s not true.

So when should you give up?

In this post I’ll tell you the story of how 4 years of trial and error resulted in the discovery of our current product architecture and why we start every engagement with a focus on email productivity habits.

But this story is also about a deeper business question: when should you give up on something that isn’t working? I’d like to hear your thoughts on when you think you would have thrown in the towel if you were having the same experiences over a 4 year period.

Also by the end of this post you might find you’re as obsessed with email productivity as we are 🙂

Round 1: The “Do It Yourself” Info Product

In May 2014 I was primarily running Working Software and building custom web-based and mobile applications. I was also doing a bit of AdWords and online marketing stuff.

I went to a business information session one evening held by a couple of fantastic coaches by the name of Sean Collins and Jo-Anne Bowyer.

The next day I was inspired to do a brainstorming session based on some of their advice and I realised my best software clients were already-profitable small businesses seeking to streamline and automate business processes, even though most of the enquiries I got were from startup founders looking to build the Next Big Thing™ (most of whom wouldn’t exist in 18 months).

So I started The Procedure People.

Based on my experience of systemising and automating my own software company I created an information product called The Stressed Out Business Owner’s Policies & Procedures toolkit: a wiki template and a handbook with videos on how to document their business.

Of course it didn’t work.

The main problem was that no stressed-out business owners had the time to learn how to document their business and although there was some interest from the market the idea basically went nowhere.

Round 2: The “Done With You” Consulting Product

In 2015 I started working with another great coach named Dan Liszka and he helped me turn this into a consulting product.

I went out to market with a product called the Three Month Capacity Kickstart. The content was basically the same. It was all based on the toolkit, but it was a “done with you” model rather than a “do it yourself” model.

The idea was that I get the first couple of procedures done and then the client will be able to outsource those processes to remote workers either in Australia or overseas.

This would achieve an incremental capacity increase without the need to hire additional full time staff. With the increase in capacity they would then be able to go back and continue the work by themselves and they would be off to the races!

Of course it didn’t work.

Even though it sold well and there was definitely demand for the product, we never quite achieved the capacity increases we set out to achieve.

One of the biggest challenges was getting the information we needed to create procedures in a timely manner, but over and above that my impression at the time was that the root cause was a psychological barrier around hiring remote workers. Even in cases where we had a solid coverage of a range of different procedures, the roadblock always seemed to come at the point of hiring people to work remotely.

Back to the drawing board!

Round 3: The “Done for You” Full Service Product

In 2016 I came up with what I thought was the solution to 2015’s problem: it was called Part Time on Demand.

Because I had assumed that the problem was a mental roadblock around hiring and collaborating with remote workers, I set about hiring a team of four people (two onshore, and two offshore) who would then execute the procedures that we created for that company.

Again this sold pretty well but once again the delivery fell short.

After a couple of months people would taper off either declaring that it didn’t work at all or that it just didn’t work for them.

A couple of companies managed to get some success with it but it was a really tough ride.

I was pretty perplexed, not least because I was using the same systems, procedures AND staff as my clients and getting really good results. I just couldn’t seem to generate the same results for my clients.

When I was talking to one of my clients in November 2016 he sounded so stressed I asked him to jump on a video call and take me through what was going on for him.

Within about 3 seconds of looking at his screen I could see the problem.

We had put in place a helpdesk system to simplify the process of collaborating on emails with workers remotely and this changed the way his inbox looked as well as changing the types of emails he received.

I had never experienced the same problem, but the way I managed my email was completely different.

The Epiphany

When I read the book Getting Things Done by David Allen in 2007 it clicked immediately.

I have been at inbox zero ever since.

I internalised it so strongly that I forgot that I had even learned it. I just assumed everyone else had a system for managing their email that was similar.

The way this client (and, as I would soon discover, many others like him) managed email was to scan through the inbox and build up a quick mental model of what his priorities were.

This required that he have an intimate knowledge of what his inbox typically looked look like and that the patterns of what he saw were relatively constant from day-to-day. It also meant he held lots of stuff in his head because of the inflexibility of the email interface.

I realised immediately that if I could help my clients and their teams develop the same habits I had learned from reading David Allen, all systemisation and change management would come much more easily.

Building the Product

The only problem was that my system for doing so was so technical and complicated that no one else could ever be expected to learn how to do it.

I quickly built an integration between Gmail and Trello using Zapier for that client and trained him on how to keep his inbox empty.

To my delight he loved it so much he stayed committed to being at Inbox Zero every day and we started achieving some really great results for his business.

Initially I didn’t even really think about this as a product, but as more clients began using the system we had to replace Zapier with a Google Apps Script due to limitations in Zapier. As it grew more sophisticated it started to feel like a Real Software Product™ which I named BenkoBoard.

Epilogue: The Changing Face of Software

Not only did I discover during this time that people had challenges with productivity and communication that prevented them from implementing effective systems, but also that the landscape of possibilities for creating automated systems had changed.

Google Apps Script matured immensely from 2014 – 2017 and, coupled with my experiences in building BenkoBoard, allowed me to create Trellinator, which obviates the need for writing 90% of the custom web based applications that would have been required to systemise and streamline businesses previously.

Even if you have tried Trello in the past and found that you didn’t like it, I urge you to try BenkoBoard because it fixes a couple of Trello features that are inadequate out of the box.