Optimal '22 - The Leadership Summit for Predictive Procurement

Bid Ops is now. Find out why learn more

5 Lessons I Learned About Procurement’s Digital Transformation From Competitive Debate

Digital transformation has become an important topic for most procurement teams today. As I advise procurement leaders on how to approach digital initiatives I find myself looking back on experiences from high school and college where I was lucky enough to participate in the digital transformation of an entire community of practice: competitive debate. While there are important differences between competitive debate and procurement, I believe that readers curious about digital transformation will find the lessons I learned during my time in debate both illuminating and extremely practical.

When I began debating as a high school freshman in 2002, the standard process for assembling a single debate case was a tedious, weeks-long process that was mostly paper-based. While competitive success in debate requires critical thinking and hours of intensive practice speaking, in high school I remember we spent most of our preparation time on exactly one task: organizing thousands of pages of printed paper. 

<strong>PAPER TRAIL</strong> Sam Crichton says he’s more comfortable with paper. He travels with his personal research library.

Our debate team would go to the library to get library books, photocopy all the relevant pages, hand-underline the photocopied sections that had the best arguments and the most oomph, cut out the relevant paragraphs with physical scissors, paste them onto other physical blank pieces of paper and then label the heading of the argument with a handwritten “tag”. (In the debate community this process is known as “cutting cards”, harkening back to a time before photocopiers when debaters would transcribe quotes onto index cards). The downside of relying on this manual process for cutting cards is obvious. If you can only spend four hours a week prepping for debates and three of those four hours are spent “cutting cards”, then there’s really not much time left for practicing things like speaking, answering arguments, storytelling or cost-benefit analysis. Since teams that are better at the latter activities end up winning more debates, all the time that we had to invest in the manual cutting-and-pasting workflow ended up being very expensive time from an opportunity-cost perspective. 

This problem got harder the fiercer the competition. Top debate teams would have literally tens of thousands of pages of paper in manila file folders packed into large Rubbermaid tubs. 

(Sam Crighton, a contemporary of mine who debated at Wake Forest, pushing his debate tubs at a tournament. Photo credit: New York Times “The Paper Debate,” 2010)

But in a span of just a few years, the entire debate community went fully digital. No more tubs, no more file folders, no more paper evidence. It was a massive transformation involving thousands of debate teams. By competing and coaching during debate’s digital transformation, I learned a few valuable lessons about how communities of practice can drive towards efficiency and positive change by leveraging digital technology. This post summarizes the lessons I learned that are the most relevant for procurement leaders:

Technology sparks change; economic necessity speeds up the process.

While the “paperless” debate technology has theoretically existed since the early 2000s, the tipping point for rapid adoption of digital technology in debate can be traced to the 2008 financial crisis. The airline industry was severely impacted by the 2008 crisis and had to make sweeping changes to avoid bankruptcy. One of these changes was that most of the major airlines added $25-$50 “bag fees” for every passenger with a second piece of luggage (other than a carry-on). For debate teams, these bag fees were a huge financial hit. Before bag fees, it was at least possible for every debate team to travel across the country with 2-10 Rubbermaid tubs of evidence at no added cost. The new airline bag fees forced each team to make a choice: either allocate a precious budget to pay the exorbitant costs of paper-based debating or bite the bullet and “go paperless”. In the end, going paperless won out and the Rubbermaid tubs of evidence disappeared. I do wonder — if the airline industry had never implemented bag fees, would debate teams still be using paper evidence today? Perhaps not, but without the bag fees, I imagine the digital transformation would have been much slower, less uniform, and subject to much greater resistance. Given the sudden appearance of the airline bag fees, the debate community as a whole consciously transitioned to digital technology quite rapidly. Today most debate teams prepare and read cases using laptops. 

Similarly, the drivers of digital transformation in procurement are economic rather than technological. Cloud-based software driven by AI has been popular in consumer apps for the past decade. Consider, for example, apps like Uber where AI helps estimate pickup time or Expedia where AI helps price airline tickets. Yet most procurement software on the market today does not even use basic practices in optimal user experience design, let alone AI to assist with communication, pricing or process automation. My experience is that much like debate, change in procurement will be driven by business partners who need to manage more suppliers, more projects and more processes without providing additional headcount. It is precisely when leaders feel the pressure that “something’s got to give” from an economic standpoint that the case for digital automation moves from “nice to have” to being viewed as necessary.

The technology is driven by evolving social norms around collaboration and massively improves as more collaborators join the party.

During the initial stages of debate’s digital transformation, early debate adopters used Microsoft Excel in only the most basic ways: note-taking (called “flowing” by debaters). Debate speeches in Excel were separated by different columns on a single worksheet while various sections of the debate were organized through the use of multiple tabs in a workbook.

However, for debaters to fully realize the benefits of digital automation required a massive change in debate culture which centered around the norm for pre-round argument disclosure. 

Up to this point, the pre-round disclosure norm had been mostly verbal: you were supposed to tell the other team what arguments you had previously made if you were negative or planned to make if you were affirmative. Big debate programs with nationally ranked teams quickly realized that this informal verbal disclosure wasn’t optimal for effective pre-round preparation. To ensure accurate reporting, these bigger debate programs would send a student to “scout” the debate rounds of key opponents. Scouts would then manually transcribe all of the opponent debater’s arguments (including citations), giving the debaters at these bigger programs a massive advantage. Debate tournament administrators soon realized that this manual scouting process created an unfair playing field for programs who could afford to scout more debates than their opponents. It was this fundamental fairness concern by tournament administrators that eventually drove the creation of a community wiki — along with a norm for all debaters to upload their pre-round disclosure forms, thereby reducing the advantage from a scouts’ manual transcription work. 

This shift in culture had the side-effect of making all debate arguments digitally accessible in more or less real time (for example, if you are curious you could easily see what college students are debating about in 2020-2021 by visiting the casebook wiki here). However, this change also provoked strong disagreements in the debate community about what constituted fair and equitable digital disclosure.  

Today, for example, many debate teams not only upload their citations but the full-text of their entire arguments. When I graduated high school in 2006 (a year before the iPhone was released), full-text pre-round disclosure would have been nearly unthinkable. Consider how much manual labor went into cutting the cards in the first place. Imagine for a minute that you had spent weeks pouring through library books, photocopying, cutting, pasting and labeling cards in order to discover a single crucial piece of evidence. Why would you then be willing to make it easy for an opposing team to directly benefit from your hard work? This sentiment framed early negative reactions to the wiki by the debate community, a reaction which rested on the manual, paper-based research process which was itself being disrupted by Google, Lexis Nexis and other web-based search engines. 

Like debate, in procurement I often find that technological capability is very rarely the limiting factor for digital transformation. Instead, the cultural preference for “face-to-face” supplier negotiations (often with no digital audit trail) and a “this is how we’ve always done it” mentality around email-and-spreadsheet administrative processes are the most common reasons why a procurement team stays manual. Until this complacent mentality is pushed out by procurement leadership, information will stay siloed and the business benefits of digital automation remain relatively limited. 

For digital transformation to be successful, there needs to be leadership that sets expectations that the inefficiency and lack of visibility into email-based processes will no longer be acceptable because decisions require data, not opinions. In the debate community this leadership came from tournament directors who were willing to draw a line in the sand: if your team does not use our community digital disclosure platform, then you cannot debate at our tournament. In procurement we are seeing the beginnings of this happening with supplier data, but there’s a lot more work to be done around automating data analysis tasks within the strategic sourcing process itself.

Switching to digital will be a struggle at first but it will all be worth it.

Making the switch to digital debate wasn’t easy. Some of the issues debate teams experienced may sound tame in hindsight, but I remember them being panic-inducing at the time. Preparing to give an important speech in a high-pressure competition is already stressful. Now imagine that your laptop dies and erases all your notes (and evidence) mid-speech. In 2006 this nightmare scenario was actually a pretty strong argument in favor of the paper-based debate. Then in 2014, I happened to be judging a debate in which a student’s laptop died mid-speech. Instead of panicking, her partner brought over a second laptop with the exact same copy of the speech document. She shrugged and continued giving her speech as if nothing had happened. What had changed since 2006? Dropbox (and real-time sync for cloud document storage) had become commonplace, thus removing the potential devastation of an unexpected laptop meltdown. This is the same anxiety I see from procurement teams who worry that digitizing a process will make suppliers view their business opportunities as transactional or lacking in human connection and personal context. Procurement teams often rely on relationships with key suppliers, and the idea that those relationships could be harmed by digitization can provoke anxiety. However, just like the move from paper to digital speech documents in debate, there are lots of new ways to bring a distinctive human element to digital communication. Humans are at the center of any act of communication, whether in procurement or debate competition, whether in-person or digital. And as digital systems become the norm, just like in debate, this anxiety will begin to disappear.

The sooner you embrace digital transformation, the greater your advantage.

Switching from paper-based arguments to laptop will, in fact, make you a worse debater at first. This is primarily because reading off a laptop screen to an in-person audience can prevent you from making eye contact, which is a critical element of persuasive speaking. The other reason is that laptops are distracting. There’s social media, Google News, and billions of other websites that can interfere with the deep focus needed to win debates. But if going digital is inevitable, then accepting the challenges of eye contact and distraction sooner gives will give your team the opportunity to maximize the potential benefits of the transformation. The most powerful lesson of digital transformation is this: the biggest benefits aren’t from digital technology itself. Rather, it’s from what you and your team do with the time you get back from automating manual busywork, the time that will be freed up from email and spreadsheets.

Digital champions are viewed as thought leaders because digital transformation is all about learning to change human behavior with technology.

One of the earliest practitioners of fully “paperless” debate was Whitman College. Their coach Aaron Hardy had introduced a number of the free macro-based Microsoft Excel and Word templates, and even created a software suite called Verbatim that automated many tasks required for prepping and disclosing debate cases.  When I was debating in college at the University of Michigan, Whitman’s top team was Nate Cohn and Daniel Strauss. Nate is now better known for his work as a data journalist and election forecaster at The New York Times where he orchestrates the models behind the famous Election Needle that many of us spent the latter half of 2020 eyeing with great curiosity. My college debate partner Maria and I debated Nate and Daniel twice (we lost): the first time we were on paper and Whitman was digital, the second time we were both using the same digital template-based Verbatim system that their coach Aaron had popularized. 

Reflecting on these debates, I see that the real value of these digital debating systems like Verbatim lay in forcing us as debaters to be more organized before and during our debates. Tubs full of paper files could easily get de-alphabetized, lose their table of contents or even whole pieces of paper which would then need to be re-printed and re-filed. Debate files required constant maintenance in order to be usable. Digital filing systems, once properly configured, required no such maintenance. The first time we debated Nate and Daniel, I noticed this difference – not of the digital technology itself, but of the organizational practices that it fostered. It took Nate and Daniel much less time to locate evidence, to organize their speech components, to cite specific arguments by name and to locate and describe the arguments they wanted to answer. In debate – where an unanswered argument is often treated as true – every second counts. By shaving seconds off every single repetitive task, Nate and Daniel freed up valuable time which they could then spend on persuasive speaking tasks like storytelling, re-framing and cost-benefit analysis. Because Whitman had digitized before us, they were already familiar with best practices for minimizing the challenges and maximizing the opportunities of digital card cutting and pre-round disclosure. Whitman was also able to help shape the cultural norms and process templates that other teams — including Michigan — would end up using. 

This dynamic is similar to the digital transformation of procurement. Teams that have experimented with e-auctions, supplier portals and procure-to-pay transformations are now in a better position to take advantage of modern web applications powered by AI, if for no other reason than those digital changes don’t seem quite as scary. Arkestro technology, as an example, simply would not exist without my own formative experiences with both e-auctions and total cost of ownership (TCO) benchmarking. But just like in debate, the best teams will always be the teams with the best people. Nate and Daniel didn’t win debates because they had digitized earlier than other teams — they won because they were smart, hard-working and well-prepared. Digital transformation isn’t going to solve every problem that procurement faces. But as a rule, the smarter teams will seek the benefits of digital transformation earlier, and will reap outsized benefits from its adoption.


Hopefully, the lessons that I learned from digital transformation in the world of competitive debate highlight compelling “win themes” for digital champions in procurement. I also want to avoid overselling the benefits of technology by itself. There are no silver bullets. The process of digitizing a process can be painful and can generate resistance from participants. Similar to cleaning a house, managing digital transformations often means that things will get a little messier before they get a lot cleaner. I learned this lesson the hard way: as a naysayer who was eventually proven wrong. During my time as a debate coach, I was frequently resistant to adopting digital technology due to what I perceived as short-term costs. 

The reason for my resistance was more aesthetic than practical: I simply like paper. I am an avid reader with a large collection of paper books. I enjoy and appreciate the tactile sensation of paper, the way it stacks and bends, the way it accumulates texture by being touched by many hands over time. It’s easy for me to feel nostalgic about paper debate, the tubs full of files, the battered accordion folders covered with symbols and shorthand as mysterious as any leather-bound folio of magic spells. It is this same nostalgia that I hear from procurement leaders, especially those in manufacturing, who want to share stories about epic supplier negotiations. These negotiation stories typically emphasize extreme travel to far-flung places where gut instinct and horse sense help their negotiation team turn a supplier’s devastating “no” into a mission-critical “yes”. These negotiation stories offer valuable clues for why proposals to automate any aspect of the supplier negotiation process is met with resistance by the old guard. But across the procurement profession, change is in the air. And if the digital transformation of debate offers any guidance, then those in procurement who champion the change that’s coming will help define what that change ends up looking like, not just for their own teams or business partners, but for the procurement community at large.

Related Articles

the Great Resignation

Sourcing Education

The Impact of The Great Resignation on Procurement

ESG Strategy

Sourcing Education

4 Steps to Start and Grow an ESG Strategy

supplier relationship management

Sourcing Education

Supplier Relationship Management – The Secret to Effective Supplier Relationships

ESG Program

Sourcing Education

How to Deliver a Data-Driven Procurement ESG Program Fast

supply chain resilience

Sourcing Education

Supply Chain Resilience and Sustainability – Partners or Adversaries?

Key Performance Indicators

Sourcing Education

Box and Arkestro—Procurement Key Performance Indicators and Actionable Insights For Enhanced Supplier Diversity

Rob DeSantis


As a former co-founder of Ariba running sales, Rob has deep expertise in the procurement space, having helped propel Ariba from zero to $250 million in revenue in four years and IPO of the year in 1999 before its acquisition by SAP a decade later. In addition to co-founding Ariba, Rob was also an early angel investor and board member of LinkedIn, the world’s largest professional online network.

More recently, Rob served as an investor and advisor to a small portfolio of companies including Bloom Energy, AEye, Inc., HiQ Labs, Agiloft, USEND and more. He is also a co-founder of Dibbs Technology and TrueParity. Rob holds a BSME from the University of Rhode Island.

Marty Meyer

Chief Financial Officer

A trusted partner and advisor on the executive team, Marty has a unique background having been the CFO of nine venture backed technology companies. Marty has raised over $300M in venture funding and has closed six strategic M&A transactions with a combined value of over $1B. Marty has deep domain expertise in ecommerce, consumer internet, networking, data security, data privacy, media technology and enterprise software industries. Marty is especially experienced in the finance and operations activities of SaaS companies and is driven by data and metrics to help create outstanding customer experiences and drive efficient growth.

Neil Lustig

President and Chief Operating Officer

Neil is a seasoned executive with over 30 years of experience leading and building teams in Tech. Neil brings insights from a variety of market spaces and company sizes. Most recently Neil was the CEO of GAN Integrity, an innovative SaaS Compliance technology company serving enterprise customers in North America and Europe. Before that Neil was the CEO of Sailthru, a leader in ML driven personalized multi-channel marketing communications for media and e-commerce markets. Prior to that Neil was the CEO of Vendavo, the leader in B2B price optimization and management for large enterprises. Before Vendavo, Neil led the commercial team at Ariba, the market pioneer that defined and created the eProcurement space. Neil served as the GM of Ariba Europe and subsequently the GM of Ariba North America. Neil started his career at IBM where he spent sixteen years, initially as a software developer, and then twelve years in a variety of Sales and Marketing roles


Neil has a BS in Computer Science and Applied Mathematics from SUNY Albany. He is a native New Yorker, Brooklyn born, and still resides with his wife and three children in New York City.

Bonnie Adams

Director of People Operations

Bonnie is a People Operations and HR veteran, with over a decade of experience establishing successful people and culture functions for early to mid-stage tech startups going through high growth phases. She has a passion for supporting and creating inclusive and collaborative work environments and is well-versed in driving positive changes in her organizations as a trusted leader. Prior to joining Arkestro Bonnie worked as the People & Culture Coordinator for Ionic Security, helping them scale from 5 to over 200 employees in addition to a $120M funding round. Most recently she was the Head of People & Culture for blockchain innovator Storj Labs and was the Director of Human Resources at PrizePicks, the largest independently owned Daily Fantasy Sports platform in North America.

Arym Diamond

Chief Revenue Officer

Arym Diamond joined Arkestro in January 2022 bringing over 20 years of experience in the enterprise software and consultancy industry.  He is responsible for the worldwide go-to-market revenue strategy. Prior to Arkestro, Arym was Chief Revenue Officer at CalAmp focused on Telematics and Logistics. He also served as the area vice president of North American Sales within the Salesforce.com Enterprise Business unit for Einstein Analytics & AI, where analytics and machine learning were re-imagined for the front office.  Prior to that, he spent over 10 years at Oracle in various sales positions. Arym holds an MBA from the University of Southern California Marshall School of Business, and an undergraduate degree from California State University.

2022 Gartner® Hype Cycle™
for Procurement and Sourcing
includes Arkestro.

2022 Gartner® Hype Cycle™ for Procurement and Sourcing includes Arkestro.

Gartner® Hype Cycle™ are registered trademarks of Gartner, Inc. and/or its affiliates in the U.S. and internationally and is used herein with permission. All rights reserved.


Thank you!

Thanks for all your details! We are working hard to prepare the perfect event. The final step for you is to book your hotel room and you can do that by clicking here.

Book a Demo

Find out how Sourcing Enablement with Arkestro means better quotes faster

Arkestro Whitepaper

How to Deliver the Competitive Advantage of a High-Performing Procurement Team