A Celebrity Deathmatch Debate: To Automate OR Not To Automate?

I am Jared Weiner, partner manager on the airSlate team. But I’ve been in tech now for almost nine years, which is crazy to say, I’m hitting a decade. I’ve spent my entire career in the world of documents and data. So I’ve been automating stupid stuff for a long time.

So really, really excited to work with Jordan and Annalisa today for the debate.

Just setting the scene quick. These are wonderful speakers. We have Annalisa from Signant Health and Jordan from IQVIA. They have a past. And I think they’ve disagreed about some of these things in the past, but they’ve both gone on to different companies and gotten much more experience to bring back into this conversation.

To walk through sort of the format of this debate. We’re going to discuss where do you draw the line with automating different elements of your processes? How much is too much? How much is really necessary, especially as we’re looking at regulated industries? We’ll also talk about the effect that automation can have on innovation.

Is there one? Should we be concerned about that, especially in companies that are aggressive and want to grow? And then finally we’ll talk about actually measuring the value. If you spend 40 hours automating something that’s going to take 20 hours over the year, how much does that matter? Does it matter depending on your company size or the role that it’s affecting?

So these are the questions we will talk through and the format will be a very traditional debate. So you’ll have One person goes first, then the other person responds, and then you get rebuttals for each. We will have a timer just to keep things really fun and spicy, so the lovely Shannon Gregg will be handling that.

And then at the end all of the stuff that you threw into the chat all of the debate fire that you add, we’re going to come back to and discuss, and we’ll also pick a winner. Who swayed you more, Jordan or Annalisa? And so, do stick around to the very last slide because we have some swag to give away as well, so you can sign up for that.

So, without further ado, I say we kick it up. I will start with the first question. Where do we draw the line between stupid stuff and necessary stuff to automate? And we’re going to kick it off with Annalisa and then Jordan, your reply.

Right, so I’m taking the automation cautious approach here in the debate and my husband has taught me a nice phrase that I like to use with my team a lot, which is, is the juice worth the squeeze?

So when you’re talking about automation, when is the juice not worth the squeeze? We might not want to automate when the volume of activity that the automation supports is small or very infrequent. That might be something that is better for human process or in the prioritization that you’re doing within your companies within your life doesn’t make the most sense if the benefit isn’t there, which brings us to the second point of is it a small user base if you’re automating for.

10 percent of the individuals, but that automation is going to make life harder for the other 90%. Then you probably need to rethink the, the labor around it and the change management that will occur and how painful it might be. If there’s a cost that’s associated with this and the process is unproven.

This is one of, one of my big pain points, right? If you can’t write it down on paper. before you start automating, you’re not ready for automation. If there are a laundry list of exceptions that you have to account for in the automation, it is unlikely that you’re going to get every one of them right. So then you risk having low adoption with your automation, having your automation produce incorrect results and risk the entire process.

So I turn it over. That’s fast. Okay. You caught me off guard. I was writing down your great points. So with that, Jordan, we’ll switch over to you. Where do we draw the line between stupid stuff and necessary stuff to automate? Yeah, it’s tricky. I’ll take the other side of it. I think it’s important to push the envelope in terms of automation to find out what’s going to work and what doesn’t.

With some of the innovation that’s been out there and that continues to advance rapidly today, you don’t necessarily know, you know, sometimes the first thing that you roll out isn’t necessarily the greatest, but you learn some lessons from it and then you improve it. And that could be the vendor creating something and providing that service and their services get better over time.

Or maybe there’s a competing vendor who sees what they did and then they improve upon that and actually can create a whole brand new industry. Around those things, certainly repetitive, mundane tasks. Things like self checkout, right? I mean, I personally, I hate waiting in line when I go to the convenience store.

I’m in Philadelphia. So I’ll say wow. Wow. But I know some people are in Pittsburgh. So I’ll say sheets. But when you go there, I don’t like waiting in line, right? I remember back in the day, you know, it used to be really annoying when someone would take out their checkbook and they would write down the whole license thing.

And you were like, Oh, my God, I can’t believe this person’s writing a check. Yeah. Now I get frustrated. Somebody’s paying cash. I’m like, Come on, let’s just go, you know, give the card, tap it and get out of line. And when you have the self checkout, you can kind of do that all on your own. Things requiring high accuracy in terms of just data reporting, and, you know, now with agentic AI coming into play really at its infancy, what a great thing to be able to mine all of that data sort through that data and then you’re Hopefully help start making some decisions and taking some actions based off that data without the person ever needing to be involved.

This happens to I think us all recently, you’re taking an airplane flight and all of a sudden used to be like, Oh, my God, my flight got canceled or it’s delayed. What do I do? I have to be there on time. There’s certain airline systems now where they’ll actually call you and say your flight is delayed, but I’ve already prebooked you on this other flight, and here’s where your next connect is.

And, press one to accept these new this new agenda. What an amazing thing, right? That saved me time. It saved me a lot of energy, and now I can focus on other things. And from a customer convenience perspective, it’s a no brainer to automate.

Is that the God show? All right, well let’s get back to Annalisa and give you the one minute rebuttal. So I’m going to say for Jordan’s example, I actually do appreciate at the grocery store that I don’t have to be asked by a person to donate some of the money when I’m paying, every time that I stop there.

So, That is a benefit. I think, you know, I’m a fan of stage based automation, right? It’s really hard when you’re not the user to predict all the pitfalls that the user will experience and exactly how they’re going to move through the process. Some people say 80, 20, I wait for about 65%. If we’ve got it 65 percent there, get it in the user’s hands, right?

This is probably the best information that you’re going to get. You’re not going to get this feedback from writing UATs. Scripts that are based on how you build it and the requirements as you understood it. But, in fact, for the users going in and actually messing it up, making mistakes so I think if you’re going to do it, I think you should build your proof of concept, get it out there to the users, get your feedback early to get it right.

Timing. All right. Jordan 1 1 minute to wrap this for your rebuttal. Yeah, the fact that Annalisa started off her response by agreeing with me, I think basically proves it out right there. So I should probably just rest my case. But automation has so many good purposes in our lives. I think we’re all taking advantage of it in our consumer lives.

And then we can see how those things parlay over into our business environments as well. All right. I love it. So in the end, I guess they agree with each other. I’m just kidding. Let’s not agree. Let’s switch. I think I’ve said to Jordan often. This is very true. So this next one, we’re going to switch it up.

We’ll have Jordan go first and then Annalisa will get the last word. Let’s talk a little bit about how automation can affect innovation. And I’ll also kind of expound that into areas of critical thinking as well. So, Jordan, we’ll start with you. Does comprehensive automation, in your view, hinder or foster innovation?

It absolutely fosters innovation. The example I think of when this question was posed was, the IVR systems that we all interact with on a daily basis. Right? So if you think about it, I don’t know, 20 years ago, you’d call up the 800 number for whatever thing you were trying to solve for.

And you’d have to wait for a person to get on the phone. And then, they advanced IVR advanced in quotes to a place where, you know, all of a sudden there was this never ending menu of, . You know, prompts and push this and push that. And eventually you got so frustrated, you probably hung up with it, but that was an attempt at innovation, right?

And so now that led to then the next phase of it, we’re now certain systems, which I greatly appreciate is like press one to speak with a representative. And then it’s like, okay, the wait to speak with a representative is seven hours and 35 minutes, but press two, if you want to get a call back at that point in time, and that’s a brilliant suggestion, right?

I don’t mind that I don’t get nearly as frustrated as if I’m just waiting online for someone to speak with. And now it’s actually taken to the point where some of the IVR systems are now smart enough. to actually engage in some dialogue and solve some problems with you. Now, would you have gotten there if you didn’t take that first step where you were replacing the human being the first time around with that never ending stream of menu items, which still exist in some systems today, but they’re rapidly starting to get replaced and you have a higher expectation now as a consumer when you call into one of those systems.

And we’ve seen that expand to the business world with help desk support and things along those lines. And it absolutely fosters innovation. I think that’s a great example of it.

And with time to spare. So shifting over to you, Annalisa, does comprehensive automation foster or hinder or does comprehensive automation foster or hinder innovation? So I think that human observation steps are important. And Overautomation can complicate these things, and I’m going to give you an example.

There are plenty of case studies, even in just life sciences that show this, but I’m going to give you an example of an issue that happened in 2016 with Genentech, where they were manufacturing a biopharmaceutical drug. So working with live cells needing a perfect environment. To be able to meet the requirements of this drug, they created an automated system that was meant to control the different environmental levels in the chambers.

To adjust for the balances that the drug needs now the automated system worked well But the data factors and indicators that were driving that automation was feeding it false data So the result was they ended up inappropriately Automatically adjusting the pH balances for this drug now based on the case study results human observation visuals Someone just looking at the drug would have been able to tell right away that there was something wrong with the environmental factors.

But in this case, there was an automation bias. People just trusted it. So they continued to let it run in batches. They produced all of these drugs that they. Eventually had to discard of and the impacts of that was it cost the company millions of dollars. They impacted they impacted the drug supply, but more importantly, they introduced regulatory rigor in this kind of automated system for all the drug companies.

So that’s just one example where that human element. Intervention that may not occur when somebody experiences automation bias could have saved, a lot of time, money, frustration and would have been an easy and simple factor. So I think change control processes are critical with the timing.

Great work. Jordan will kick it to you for the rebuttal. Yeah, just, Annalise’s example, she points it out. It’s from 2016, right? So I guess my retort would be after they, again, the question being, does this spur innovation as automation spur innovation? And I would argue that Genentech certainly having now had that experience the next time around.

And as we fast forward now to 2025, them and others have learned from those experience to innovate and better use that automation to take more advantage of. The knowledge gained previously to create better tools such that they’re not making the same mistakes that were made, 10 years ago. Now I think there’s a lot of examples of that in our real world.

Again, the layman example that I gave just around help desk systems, does carry over. These things get better over time and you have to try to have some trial and error and skin your knee a couple of times in order to prove on the end result. All right. And Annalisa, give me the last word for your rebuttal.

Okay. So I’ll just come back to Jordan’s example of automation and customer service, and this is actually one that I feel a little passionate about, because I do believe that there has a little been a little bit of over automation and customer service. I think that 90 percent of the time. I’m very good at Googling.

I’m very good at finding out my own answers, right? So 90 percent of the time, if I need to connect with a customer service agent, it is because the information is not available for me to process on my own. I’ve already tried nine different steps. And so, you know, I get a little frustrated screaming representative into a phone or putting in numbers that they’re not accepting and they’re reading wrong or I can just, Text them or I can speak them and it’s talking over me.

So I think that there is a frustration element there. Although I do think he makes some good points, there needs to be a better way for people that are good at finding their own information to get past those blockers. All right. All right. We got a lot of action in the chat during that. That was a fun one.

And something that Jordan talked about is a perfect segue into our final question. You talked a little bit about, you made those mistakes. And so it was, it’s the thing that allowed you to innovate, having those scrapes on your knees, if you will. So let’s talk a little bit about it. Risk and true ROI in that case, a lot of money was lost.

And so how do we compare our efforts and understand, are we actually getting something back from this truly from a financial perspective? In this case, we’re going to start with Annalisa. How do we measure the true ROI of automation? So in my personal experience, I didn’t look this up. I didn’t look at what the masses think, but in my personal experience, the primary measurements of ROI with automation is time savings and compliance.

Both of those things are drivers that increase. Monetary and non monetary needs in automation requests that I get all the time working in the technology space is to require data entry from certain individuals at certain process steps within a process. And my first question back to them is what happens if that data isn’t available?

And I think two things happen. One is they stop moving forward. They don’t have the information, so they stop in the middle and they don’t move forward. Finish the process. They don’t meet the intended outcome, and then you lose your time savings benefit. And then the second one is that they’ll put anything in to get past the blocker.

So it doesn’t matter if the data that you’ve requested is correct. It just will meet the requirements to get them to their next step to be able to accomplish their tasks. So in that case, you’re losing the compliance. And I think The two outcomes that come of the second example would be that either you are then making decisions.

Off of bad information doing trend analysis where this information is thrown off. And then probably even the worst is the entire data set comes under question. So even the good data has to be thrown out because of the bad data that you’ve required. All right, finishing ahead of schedule. So. We’re looking at time savings and compliance is the real driver of ROI for Annalisa Jordan, kicking this to you.

How do we measure the true ROI of innovation? In terms of measuring it, like, by the book, you want to establish some clear metrics. You want to compare your pre automation processes and time savings versus your post automation time savings, and then factoring in the long term benefits in terms of resource savings and just the.

Opportunity cost of individuals to spend their time on more important tasks and more medial tasks, you know, because of what happens with automation. But in terms of just real world when I think about it in my own day to day, right? We all use Salesforce. I know Shannon loves Salesforce. The Yeah, there you go.

There’s different ways to use Salesforce. And I think any one of us who have been at multiple organizations, you’ve seen it. Better implementations and you’ve seen worse implementations and as a sales lead myself for many years over right? If Salesforce is being used properly, just from a pure time savings perspective, it enables me to avoid all of the questions that I would get from management and chief executive officers and this person and that person about individual opportunities or close dates or these things because Did you look right?

Rather than bothering me and bothering my team with emails and other things, there’s a self service way for you to go out there and see these things. And then taking that a step further. Did you look at the report that might be automatically generated that shows you perhaps some hygiene issues with your salesforce reports that helps gear your day in terms of how you’re going to spend your time and when used properly?

You see a significant time savings because of that automation of the routine that is generated off of the best practices that are put into place if they’re taken advantage of. And when they’re not, then you see, again, fall back to this whole let me ping people. Let me send a team’s message to people around what’s going on with this thing.

Is it still going to close by March 31st as I’m dealing with right now, as I’m on the phone with everybody here in terms of end of Q1, and you can. You know, this enables us to actually get ahead of that. I think some of it down. I know i’m out of time I’ll squeeze it into my rebuttal All right, we’ll get to your rebuttal soon first.

Annalisa is he’s saying essentially time is money for sales So I hope I got that right jordan, but yeah, it works getting to your rebuttal. How would you respond? I think time is also money for the people that are automating to support sales. And I’m currently working through this example because in my current, in my Salesforce instance, we need the ability to be able to understand when bids come in through different channels that are related, that are attached to the same protocol.

And we have different sales reps assigned to those different accounts and to the Sierra. So there’s. Often not a connection. There isn’t one funnel that will allow us to know this. So, we tried to create a flow that compares protocol numbers eliminates things like TBD when they don’t have it in.

And what we found was we were going in daily to adjust the anomalies that people would put in those fields to the point where the burden Keeping the automation going was not worth the cost. And maybe, it’s just resolutioning. But when you think something is as simple as that, right? And then you build around it.

There is also that cost of not getting to other needs. All right. And final word on this one, Jordan. How will you respond? Yeah, we all see something that works well, and we all see something that doesn’t work so well. And, adaptability and the ability to throw something out, fail faster is important for all of us.

I think the build versus buy equation comes into play when you’re thinking about innovation and automation. I’ll go back again. I’ll use the go back to the Salesforce example. The early first CRM system I ever used was Goldmine, and it was horrendous. No one used it properly. It was awful. And it was just a giant waste of time and had all of those flaws that Annalisa was just mentioning right now.

You have to identify those things and then be able to move forward. And certainly if you’re buying or trying out these things from a best in practice provider, you can then make your own determination around what’s working for you and then. Audible as needed to adapt, to make sure that you’re getting the value out of this innovation.

All right. I feel like some of that is coming down to whose time is worth more, which is a hard question to ask. The salespeople. They’ll make sure you know that. Yeah, that’s a real question we have to consider is whose time is worth more. And then if automation does exist, is it actually worth salespeople’s time to do all that data input anyway?

Cause a lot of times I think that’s the number one problem we have is they will, you can create the automations. They’re not going to take the time to do it. If there’s a value add for them, they will. That’s what I’ve seen. So if there’s if they get value out of inputting that data and it saves them aggravation or time or cost or process that they would have otherwise had to spend time on an aggravation on and they will absolutely do that.

And I’m shining proof of that example when I’ve used a good system versus when I’ve used a not so good system. Yeah. All right. Well, let’s shift this to a Q& A for two or three minutes. Lou here has, you don’t even have to ask a question. If you have an opinion on this you want to share out raise your hand or type it in the chat, whatever you want, but we can allow you to speak if you raise your hand.

I’m gonna start. What I thought about throughout the debate and Jordan and Annalisa, I really appreciate all your thoughts and input and perspectives, but it’s like the build versus buy approach. Is it worth taking a really great or really great pieces of technology that are microservices and piecing them together, but it’s going to have a lot of tech debt.

It’s going to take a lot of time. It’s heavily coded versus potentially making a bet with a newer SaaS product that might actually do everything you need out of the box. Could end up being really expensive in the end, but what’s worth it in the end from, time investment potential revenue growth.

And reducing headaches from the team, which is salespeople complaining. So that’s what I think about. It’s not really a question, but it’s more or less. What’s the approach that you would take either Jordan and Annalisa. Annalisa, if you want to start, anecdotal comment about this tying it back to Salesforce.

I, in the current role that I’m at my former manager, my former boss at one point when we were doing something in Salesforce, and I’m actually going to take the automation side for this because the debates. Parts over, right? My former sales manager said, but is Salesforce meant to do that? Is that what it was built for?

And I said, you know what, probably not, but my, when I bought my phone, I didn’t buy it to take pictures. I had a 600 camera that was meant just to take pictures after I got my. First, second smartphone and the camera capacity was so good, I stopped getting that 600 camera out of its case. So sometimes it’s not just about is it meant to do that when you’re consolidating different processes.

It’s about where you live and where you do your work, where you do your personal things. It’s about the ease of use to the individual. So I think that’s the kind of question that you need to ask yourself in the build versus buy. I love that. And Andrew, I saw you had a question. Yeah, yeah, I do. So outside of the the world of like, you know, pro or against automation, I’m just really curious, Jordan and Alisa, how you feel about the timeframe in which things are happening these days.

Innovation is moving so quickly. So it’s a constant thing internally where You know, live and Shannon are also very involved in this. It’s okay, how often are we evaluating what we are planning to automate? How often are we evaluating our tools? For both of you, people who are, obviously very forward thinking and always paying attention to trends and the way the technology is moving.

What is your advice for someone who wants to keep up with the pace of innovation, but without overcomplicating it so that they’re, there’s a new tool every day. So I, you obviously can’t look every day, but you know, what is your advice to an organization like that? My advice, I’ll take this one.

And at least if you don’t mind the way I would approach it is to, we all have our core competencies and we all have our day jobs that we need to get things done in. So we don’t have all of the time in the world to continuously evaluate these solutions and then try to implement them and then try to monitor those and try to spend all of our opportunity costs in that arena.

So it’s important to, I think one, you know what has worked before. What do people have experience with previously and recently and to take some of those lessons and bring them in so that you know you have at least an edge to have an advantage to be able to implementing that and having similar successes if implemented properly to what people have experienced previously.

So I think experience really weighs in heavily here. Things are moving so rapidly. I mean, we are just, as we all know, we’re just scratching the surface of AI and what that is going to do over the longer period of time. And none of us, I don’t think, really know. And the world five years ago and the tools that we use could look totally different.

Maybe it’s not even five years, it might be two years. Might be less than that. Might look totally different than it is today. And to try to keep up with that pace is insane. So if you’re going to try to have progress today, I think you have to fall back into something that is tried and true and that has worked for people previously, ideally people that you know and trust that are already within your organization or trusted partners outside of your organization to come in there and implement things that have been, that would be my advice.

I I love that, especially the idea of like trusting the people. Software is pretty commoditized now. Anybody with a I and some brains can build a product out. So you have to trust the people you’re working with. So last question here, and then we’re going to have a swag giveaway vote for the winner as well.

So the last question here is around. How do you actually calculate the ROI of, you know, whose time is more valuable? And so Obviously you could get into nitty gritty of, do you go to HR and actually literally calculate that way? There’s different ways to approach it. So I’d love to hear from one of you how would you calculate ROI?

I’ll start. I’ll go quick. I think it’s a really problematic even outside of the automation and technology space. Calculation of our ally. A lot of times it’s extremely false, but I think that my biggest issue with it is typically when I’m working on something and that’s a metric of success component, right?

It takes a long time to get there and people don’t want to wait. So they will. Dismiss. They’ll basically say these were bad results because ROI, when it comes to measuring efficiency cannot happen overnight when you’re changing processes when you’re asking somebody to do something differently. So I think when you’re thinking about that, there has to be a decent measurement of time to allow for that adjustment period and then set a time point to come back and revisit and say, you know, with any kind of like purple’s automation.

That’s an easy measurement. How many were you able to do in whatever time period, but for most things, it’s not as simple as that. I love what you said about time and the investment costs that you need to be, open and honest with yourselves up front as to like, what are our expectations in terms of when we should start to see some results?

And what did those results look like? What are the key success factors? And, how should we start measuring them? Because, like you said, you don’t get those benefits overnight. Again, I’ll go back to my sales mentality. I think you can measure ROI a little bit more specifically without looking at individual roles and which person is it benefiting?

I won’t even go to the salesperson. I’ll look at the customer, right? To me, I measure ROI in terms of repeat business is at least with a complex sale with a strategic sale. A good salesperson sometimes can win a first deal. But the R. O. I. In terms of the automation can really help you then get that customer to a place where they feel that your services are providing them with enhanced value and are differentiated from the others and that they enjoy working with you and your company and your product more so than the others.

And so when they’re then validating your investment in automation by willingly giving you a significant or an uptick and repeat business is compared to the free automation days. That, to me, would be a prime factor to look into. All right. We’re back to this concept of customer service. It has been a theme.

So while you take a photo of this QR code to get some swag, we’re going to do a quick vote. And so I want everybody to give a reaction. So if you look at the bar, there’s going to be reactions as one of your options. And so Well, hold on. I can’t even see it myself, so I’m going to stop sharing for a second.

So there’s a react button. I want you to use a heart for Jordan if your vote goes with Jordan and clap for Annalisa if your vote goes with Annalisa for the winner of this debate. Who swayed you?

Okay, so far the heart. Oh, now we’re even. Oh, Annalisa. Annalisa is coming in for the win. Oh, another for Jordan. I think at least it has still edged out here. Oh, wow. Well, congratulations. Please use this QR code if you want some great swag Jared, what will they be getting from this swag? We’re trying to figure it out.

It could be, it could be t shirts. It could be but we’ll send you something great tea. Yeah. If you like tea, it’s all stuff that I think everyone on this call will like in the morning. Hey, thank you all for coming and doing this. We wanted to try something different. I thought it was fun. I’d love to know what you as the audience thought of it.

So please feel free to send me a message on LinkedIn. If you want, we can Figure out ways to do more of these and make them a better experience for you all. Thank you, Jordan, Annalisa. And thank you to Airslate who helped put all of this together. I really appreciate all the help you all gave also shout out to Airslate for.

Helping me get a customer up and running on your workflow product in like eight hours. So thanks for that this week. We’re just here to alleviate headaches! We really appreciate Shannon and Liv, it’s our pleasure to work with you.

Thank you everyone for coming!

 

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