Before AGILE there was, well, agile

November 2019 marked the publication of a memoir by Ameritrade CEO and Founder, Joe Ricketts, The Harder You Work, The Luckier You Get. I led the internet initiative at Ameritrade to the internet and spent many hours being interviewed for this book. Chapter 10 (page 245) highlights some of that story. Following is some more detail.

Like many software development teams in the 90s, we were struggling to keep up, as the internet – rather than floppy disks – became the data delivery method of choice and previously successful development models began to break down. This new paradigm was powerful because we could just update all our clients’ software at the flip of a switch. But it was also fraught with danger as it became very inexpensive and easy to launch new code without appropriate quality control. 

The Egyptians were not Agile

 In the olden days, almost all projects were delivered following a waterfall project management process. Even the pyramids likely started with some sort of primitive blueprint which included every thought and idea that the hoping-to-be-immortalized king might have in his head. As challenges to designing crept-up during construction, they were dealt with via design compromises. As a result, end projects were almost always something less than they were initially intended – even if nonetheless cool.

As people got better at building skyscrapers, ships, and bridges, they got better at estimating the time a project would take. Estimates were created based on the average of past projects scaled up or down to match the one at hand. We can imagine the thinking of an engineer in 1890:

That last bridge took 2 years and was a mile long. This new one is 20% longer so it should take about 29 months.

As our society of builders approached the middle of the 20th century, waterfall project management was very nearly perfected for capital projects. Engineers were aware of the details, pitfalls, and requirements of their projects. They were good enough that we were able to put a man on the moon!

Old practices didn’t fit new products

But around the time of Apollo 11, a new generation was coming of age who would challenge the time-tested results of waterfall concerning software development. Capital projects had been physical-resource-based. Metal, factory space, rivets, steel, and labor had gone into building the monuments of the previous two millennia. The new monuments were to be made of information, communication protocol, mental horsepower, and electricity. They deserved a new method of project management that matched their intangible materials.

Taking cues from Japanese manufacturing, their own experiences, and the changing relationship between programmers and users, computer engineers began to advocate for smaller production cycles that were more flexible. They sought to replace the heavy process of waterfall with something lighter. They promised to increase their accountability and transparency in return for a seat at the planning table and the opportunity to honestly manage executive expectations. Enter Agile.

There is a romantic notion within the software development community that in 2001, a group of 17 computer scientists got together in Utah and invented Agile software development. But that is really not what happened. In truth, engineers all over the world had been wrestling with the problems of building software in executive-driven environments and by the 1990s were coming up with similar solutions. The birth of the internet, and the explosion of users demands, really kicked the discussion into high gear.

Ameritrade

I was in Omaha Nebraska in the 1990s. Omaha might not have much of a silicon reputation, but due to its central proximity and favorable demographics, it was an early hub for military, communications, and technology providers. My company was Ameritrade even though it was called TransTerra at the time. Our technology team was part of the greater Omaha tech community. We knew each other, met regularly to discuss issues and share a beer and traveled to the same conferences. You can always spot a traveler from Nebraska because invariably they will be wearing red or have the state name emblazoned across their chest. It helps when they get lost.

 As TransTerra changed its name to Ameritrade and its number of clients grew from thousands to millions, we were under unprecedented pressure to revamp the way we built software. At the time Amazon first bragged about $1 million days, we were already seeing $100 million days. Our development cycles were built around exploding demand, for which our capacity increasing releases were regularly inadequate. And every day we were learning how better to present our interfaces. Clearly, long, waterfall development cycles were not going to work anymore.

In the spring of 1998, following the crush of a few 80-hour/week development cycles, we put a stop to the treadmill and took a step backward. For nearly three weeks, the development team and I locked the doors, sat together, and wrote what was to be Ameritrade’s new software development process. We called it the Cooperative Software Design Process.

I wish I still had a copy of that original document, but it is long gone. What I do have is a PowerPoint simplification, dated a year later (1999), that was presented to executives and new management as part of an initiative I worked on with my buddy, Ronny Gal from Boston Consulting Group (BCG). It is interesting to review and note how many similarities there are to what we now all know as Agile.

I have attached one particularly interesting slide from that deck. Much of it will feel familiar.

  • Cooperative acknowledges that the stakeholders were part of the process.
  • Concurrent iterations allowed us to deliver features more quickly.
  • The overlapping snail-shell arrow that has come to define Agile diagrams
  • That spinning idea generator up front was our version of ongoing backlog tasks
  • The little note in the bottom of the call-out box “smaller is better”

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We missed a lot of important Agile components too. We didn’t think of time boxing, completed software instead of status reports, or daily stand-ups, but those things probably weren’t appropriate to Ameritrade at the time. We were creating a process that allowed our business units – and subsequently the end-users – to understand that they were in control of what we were doing. In retrospect, it was quite appropriate.

The emergence of the internet changed a lot of things in the mid-90s. Companies that didn’t embrace it went away and those that did were forced to re-evaluate the way they did business. Few companies were as shaken and shaped as much as Ameritrade. Every element of the company was put into flux – but nowhere greater than what became the internet development team. We were pioneers out of necessity and lucky that the pre-Agile discussion was one of which we could be a part. These concepts helped our team progress to maturity and paved the road for Ameritrade’s growth and eventual position as one of the largest brokerages in the country.

Additional posts in this series:

Yup, I’m entitled.

I am a white male who was raised in a middle-class subdivision and a nice house. We had a sledding hill in our front yard with a wide oak tree at the bottom that – as legend has it – was standing there when Ulysses S. Grant traveled the Stagecoach Trail on his way to Galena in the 1860s. The town was Rockford Illinois, a place where no one visits, and no one leaves. We had a train station there once, but it closed. Then we lost our bus station too. Rockford in the seventies was a town where residents grew up thinking that the big city – even one as close as Chicago – wasn’t for us. Where people thought airplanes were for fancier types, and international travel was, well, not even invited into our imagination.

I was entitled to be raised by a single mother. My father had never been one long for employment, and so when he left, my mother was left with no prospects, no alimony, and no child support. Still, she was entitled to the “American Dream” and she vowed to keep that house. It was the foundation of what was left of our small family. Towards that goal she worked multiple jobs while going to school in pursuit of a teaching certificate.

My mother and I. The early days.

I was entitled to have a mother who turned out to be a great public-school teacher. She was loved by her students and her parents. Yet, every fall she suffered through strikes or pink slips. Once at the end of a RPS strike, she inadvertently crossed a picket line to get her classroom ready for her returning students. That afternoon she found her tires slashed in the school parking-lot. The cruelties and challenges she suffered on my behalf are almost too much to consider.

In junior high school I was entitled to receive free lunches from taxpayers. Free-lunch kids had a special line that snaked through the lunchroom at the busiest time of the day. Those better off heckled from their seats and threw uneaten food at us – alms that not even the poor wanted. Cheers went up for face shots and extra points were given for making one of us cry. I stopped eating lunches and was entitled to have a school library where I could pass that 45 minutes for the next two years.

When I was in high school, I was entitled to become a hoodlum like my peers or get a job. My mother helped me with that decision. Now, this was Rockford Illinois, the most depressed city in the country. Minimum wage was $3.35 but with unemployment over 20%, minimum wage was a king’s salary. I took a job washing dishes for $2 an hour working weekend nights from 8:00pm until 4:00am. I was 14. I would go home at the end of the shift with $16-cash in my pocket. On school nights I could go home at midnight.

I am grateful to have been entitled to leave Rockford – alive. My first friend to die was my childhood best friend, Paul Ogilvy, who died of cancer at age 21. Jim Roberts who lived across the street from him followed soon after with a shotgun in his mouth.  My dear friend Debby Warden was a drunk driving casualty as was Renee Ring and Glen Nichols.  There were a couple others too. Oh, and we should not forget poor Tammy Tracy, sister to my first-grade bestie, Darren. Her teenage body was found in a cornfield. All this before I was 21.

I was accepted to the University of Chicago where I was entitled to get my ass kicked and make the best friends a fella can make. My mother couldn’t pay for it, so I got through by “beg, borrow, or steal” – which really means borrowing and working hard. School was difficult, and I joked, I was fired from more restaurants than my classmates had eaten in. It took me an extra year, but I made it through.

After college. I was entitled to find a job, quit, and find a better one. Then I was fired from that job and found a better one anyways. But then, I quit that one and finally found an opportunity in which I believed. I was offered the opportunity to invest, and I was entitled to risk everything I had (and everything I could borrow). I took a speculator leap knowing that if it failed, that burden was no one’s but mine.

But it didn’t fail. And with financial success came a generous life with my wife, my family, and my community. I was entitled to enter semi-retirement, get involved with charities, help in a meaningful way, and make gifts larger than I ever would have thought possible. I take great pride in knowing that I have made a positive difference in the people’s lives.

As my children aged and needed me less, I found myself desiring to return to the corporate world. I missed the camaraderie and shared goals of working as part of a team. But finding a job did not come easily, and I readily saw how dispassionate hiring managers can be. As a male in my late 40s who had not worked in more than a decade, I suffered intentional bias, unintentional bias, ageism, and sexism – all the while reminding myself that every obstacle was surmountable. After many years of learning how to get around those people, I finally landed a great job where I am using all my entitlement to make a positive impact on culture, efficiency, and revenue. It is from there that I write this post today.

Like many who succeed, I have been entitled my whole life. I have been entitled keep a positive attitude. I have been entitled to show compassion learned from hardship. And most importantly I have been entitled to believe we are entitled to something better than the lot we were given.

So yup, I’m entitled. And even if I’m not, that’s my story and I’m sticking to it.