Applied AI: The AI Hackathon Playbook

Okay, everyone, this is the last episode in our series on Applied AI, and today we’ve got something extra special for you.

So what do you do when you want to harness the collective energy and enthusiasm of your team?

If you said pizza party brainstorm, head to the back of the line.

What we’re talking about today is gathering your team for an AI Hackathon.

So step right up, this episode is for you.

Hi, I’m Courtney Baker, and this is AI Knowhow from Knownwell, helping you reimagine your business in the AI era.

As always, I’m joined by Knownwell CEO, David DeWolf, Chief Product and Technology Officer, Mohan Rao, and NordLite CEO, Pete Buer.

We also have a discussion with Jeff Gallimore, the Chief Technology and Innovation Officer at Excella, about what he’s seeing in the GIN AI space, Excella’s approach to hackathons, and how GIN AI is impacting modern software delivery.

Hey Jeff, welcome to the show.

Thanks for being here.

It is wonderful to be with you.

Our conversations are always so amazing.

So one more opportunity for that.

You know, we’ve known each other for a long time, and Courtney has already given a brief intro to you, but I’d love for you to share a bit of your work at Excella for our audience.

Yeah, well, so Excella, we’re a tech services company.

It’s headquartered in Arlington, Virginia.

Although like many, we have people all over the country these days.

We build, modernize, operate enterprise systems using modern practices.

We help organizations use data, AI, analytics to make better decisions and operate more efficiently and effectively.

And we help teams and organizations transform their ways of working, help them get better outcomes.

Much of our work is with the federal government, which is an interesting place to be these days.

And we also have a portion of our business is with the private sector, which is kind of interesting because it gives us the ability to bring some lessons and learnings from each sector to the other.

Yeah, you know, that combination is always so good, right?

So you can take lessons learned, like you said.

Jeff, this may sound like flattery, but it’s not.

You are one of the smartest people that I know.

As you’re working with your clients, what are some of the common themes that you’re seeing with the deployment of generative AI and the work you’re doing with your clients?

Well, flattery will get you everywhere, Mohan.

So just start with that.

But it happens to be true in this case.

But first, in terms of the common themes around deploying gen AI, first of all, everyone is talking about it.

Everyone is planning for it, and many are doing something with it.

I don’t think that comes as a shock to anybody.

But second, we’re also seeing real challenges to organizational adoption.

There’s certainly a lot of discussion and planning and activity, but there’s a lot of challenges that are real to adopting this kind of technology within the organization and the enterprise.

Probably the most obvious one is the availability of tools or the tech, especially within highly regulated environments.

Think about federal government as one of these highly regulated environments.

I think this is also true in the financial sector, insurance, things like that.

But these tools are, they’re new.

They come with a different set of risks associated with them.

There’s different controls and different, we’ll call them consequences, some of them unintended, that, you know, there’s stories out there and people are different, different companies and different organizations are taking a different stance at adopting those.

Another challenge that we’re seeing with organizational adoption is in the scaling approach.

So if you’re an organization has already started down this road of adopting and using generative AI, you’ve probably started with a proof of concept or prototype or pilot within your organization or enterprise.

We’re seeing sort of this chasm of that stage of experimentation to full on adoption and scaling within the enterprise.

Those concerns change when you move from the pilot stage into the production operation stage and a lot of organizations and I think, generally speaking, our industry is trying to wrap our brains around what it really takes to operate these kinds of solutions and tools at scale.

Yeah.

So would you say then the hype is real, but then it also meets reality and the reality is much more complex?

I think that’s a very accurate way of putting it.

It’s very easy to get started with this and very exciting when you do.

And you start thinking about all of these possibilities that this technology or these tools can help you with.

And then you start thinking about all of the scenarios and the edge cases and the what ifs and the, oh, I hadn’t really thought about that.

Or you experience these, what we call failure modes.

That just came out of nowhere.

It gives you a little bit of a pause.

So I can totally understand a lot of enterprises that are thinking very intentionally about how they want to, how to bring these technologies in and use them.

Yeah.

I really love how thoughtful Excella is when it comes to promoting, but also using Gen.AI.

Another area that I really admire about Excella are your Gen.AI hackathons and hackathons in general.

I’ve had a little bit of a peek into how you do it.

They’re among the best I’ve seen.

How do you run these hackathons?

Any recommendations or best practices?

What have you learned over the years running hackathons?

How can our listeners use it?

Last year, we ran two hackathons, both of which were focused on Gen.AI.

I participated in both, which was highlights of my year.

Both were very different from each other.

The first one, which we had in the spring, we had, just to give you a sense of order of magnitude here, we had 83 of our employees participating in this.

Again, I was one of them, on 18 different teams.

And the structure of this was, it was asynchronous.

So not everybody was working on the same stuff at the same time.

It was over the course of a month.

So we launched it, set an end date for it, for the submission and then the judging and then the final, you know, final announcements of who won the hackathon.

But it was basically up to the teams to figure out what they did, how they worked together, what they wanted to build, how they wanted to build it, all of that stuff.

And it was, again, it was it was async.

The second one that we had, which was in the fall, was more focused.

And in this case, it was focused on agentic AI.

So that concept had started to become more prevalent in the industry.

We started to see more opportunities for how to apply that in our work and with our clients.

And so we wanted to really focus on what agentic AI looked like and give people more familiarity with that.

And so that hackathon was one week from start to finish.

And the first day of the hackathon period was a day when most of our clients weren’t working.

But we were, so we had some more focused team time.

So the teams could form storm and norm a lot more effectively in that first day than maybe they had been able to in the previous hackathon in the spring.

So those were the two hackathons that we ran.

Some of the lessons that we picked up from that, I’ll give you three.

The first one is going to sound a little trite and obvious.

But it’s to be intentional about what you want to get out of the hackathon.

We did that with both of these.

Is it a delivery challenge that you want to tackle?

Is it a business opportunity you want to pursue?

Or really is it just learning and creating more familiarity with the technology?

That was really the first one and maybe even the second one too.

Getting more familiar to GENAI generally and then GENAI specifically in the second one.

The other lesson, which again is maybe pretty familiar for a lot of folks, is rewards and recognition are important for this.

It’s tapping into both internal, intrinsic and extrinsic motivations of the participants and our employees.

So we all love learning and so me especially, I’m like first and foremost for that, carrying the banner for that one.

So it’s like, show me an opportunity to learn and I’m in, doesn’t matter what, and I think a lot of our folks are like that too.

So just creating that opportunity is a great motivator.

But also we publicized it a lot within the company in advance and told people what this was all about and how it was going to be structured and, hey, this is really going to be a great opportunity to learn and connect and advance your career as a technologist.

We had prizes that people could get for the winners of these hackathons and also swag and gear for anybody who participated.

So there was a, you know, just for showing up kind of thing was great.

So you get, you know, you get your sticker, your shirt or whatever.

And then the exec team showed up to signal how important this was.

So the executive sponsorship, myself included, for just participating in this.

But we also had some other executives participating in the hackathons.

So that sent a signal about the value and the importance of this.

And then probably the last the last lesson that I’ll share is enabling constraints can be a good thing.

So can do whatever you want to do.

But enabling constraints could also be good.

So the first hackathon, we basically set it up is like, do whatever you want to do, build whatever you want.

Here are some suggestions on tools you can use and maybe some ideas.

But, you know, y’all do you.

In the second one, it was much more structured.

We had a couple of scenarios.

And then our hackathon organizing team, basically created a platform in the scaffolding for teams to start with.

So there was software, there was a deployment platform that we were, that each team was deploying to.

So there was a pre-built pipeline for everything.

There were API keys that everybody could plug into.

So these enabling constraints and a relatively clear extension point for where you would take that scaffolding and what you would do with.

And that helped the team really get in and learn.

There was a lot to learn in that one.

And it helped us learn the things that we needed to learn.

And also add a little bit of creativity under enabling constraints to be able to get the most out of the hackathon.

Amazing.

So it was really well planned then.

You know, the knock on hackathons is that everybody gets excited, you work collaboratively for a few days, and when it’s over, it’s back to business as usual, right?

I mean, we’ve experienced that too in the past.

What makes your hackathon different?

What can you do to have a lasting value, whether it’s in your client work or proposals or fostering innovation?

What are some of the tricks there?

Yeah.

Well, I’ll point out probably the biggest one that I think we have working in our favor that makes these differences is our people and the desire to learn and grow and develop.

I think when you start with that as a, we’ll call it a core value or inherent value part of the DNA, it’s like it’s much easier to get, to do these things and get value out of them.

So when it’s already wired into your culture, your organization, what we’re doing with a hackathon is really just tapping into that and channeling that and the magic will happen.

I’m probably overstating that a little bit because there was a lot of work from our hackathon team to make all that magic happen, for sure.

Some of the things that we did that might be interesting to hear about, one is we engaged some of our clients as judges for both of the hackathon.

So that did a couple of things.

One is it raised the stakes for our teams.

So it wasn’t just our employees involved in the hackathon.

It’s like we have a client who has got eyes on all the stuff that we’re doing and is going to be judging what the teams produce.

So that was fun and motivated.

Then it also created a connection with our clients in a different way.

So we’re showing off all of our innovation and creativity and getting them involved in that.

Hopefully, that rubbed off a little bit on them.

We also got our client teams working on hackathons together.

So, if we’ve got an engagement team or a project, in some cases, the people that were already working together in their daily work got together and said, hey, let’s be a team for the hackathon, too.

So that allowed them to bring shared context and existing connections and working relationships and norms from their daily work and the client into the hackathons and made them, created a different kind of experience that was fun and they were productive with that.

And then another thing that we did was following up with our engagement teams on how they can apply what they learned from the hackathon to their daily work in the client environment.

So bringing those ideas and those lessons from the hackathon.

And there were actually a couple of really great stories that came out of both of these as it relates to that.

Number one is, one of the teams from our spring hackathon was one of those client teams that had gotten together and say, hey, let’s be a hackathon team and do something.

And so they did something, and then they brought that learning back to the client environment and had the opportunity to share what they had done with some of the client staff.

And it turns out that in the course of sharing that, they all recognized this problem or this opportunity that was in the client environment, that what they had built was actually relevant to that.

And so then we had a demo, we had a conversation, and it turned actually turned into a project.

So we’re taking basically the solution that we built in the hackathon, and we’re implementing that, roughly speaking, in the client environment to solve the need that they have.

And then in another case, another client, they saw what we were doing with the hackathon internally to us, and they wanted to replicate that in their environment.

So they wanted to engage their staff in doing a hackathon as well.

So we helped them shape that and execute that in their environment.

So that was really fun too.

Yeah.

So it was a good combination of being innovative and aspirational, but also underpinned by being practical enough.

So there was a lasting impact.

That’s awesome.

That’s right.

Yeah.

It’s the app.

You know, innovation is great.

For us, we really get jazzed about the application of that in practical ways.

Hey, Jeff, this was so much fun.

Thank you for being on our show.

Really appreciate it.

My pleasure.

Thanks a lot, Mohan.

Hey, you’re a busy executive of a professional service firm, and it is tough out there.

It’s tough to scale a professional service firm.

And what we’ve built at Knownwell, we built it just for you.

We know it’s hard when you have to make decisions based off gut or the subjective information that you can gather.

Knownwell actually takes the guesswork out of that.

It takes all the data in your organization and tells you exactly what’s happening with your commercial relationships.

So if you’d be interested in stop having to rely on gut and start relying on data, we’d love to show you your data on the Knownwell platform.

David and Mohan begrudgingly told me that they’ve been a part of around 50 hackathons combined.

So what advice do they have for you if you’re ready to run an AI hackathon?

Let’s find out.

David, Mohan, you two were recently in a hackathon in Romania and that we were all together last April for a hackathon as well.

So here’s what I wanna do.

I want to get, I mean, one, some stories, but also general thought about how to approach these in-person sessions and why they can be so fruitful.

You know, one of the things that comes to my mind is a lot of folks may not be familiar with hackathons, depending on what type of business they’re in, right?

As technologists, Mohan and I have been in part of hackathons for a long time and in a lot of different ways.

AI is interesting because with the interface that we now have to these large language models, business users can interact with machines in ways they haven’t before.

And I do think one of the interesting things as I start to think about how is this applicable to everybody is we can have traditional hackathons with technologists.

And what I’ve found over my career is there’s a couple of secrets to the recipe there, right?

One of them is like clear business objectives.

Don’t just play to play, but try to really drive at, we’re trying to develop things that are useful to our users that are going to drive the business forward and really try to define that.

The other thing is cross-functional teams, right?

It’s so important that you have somebody from the business, somebody from the technology, somebody from the user experience.

In this world, data science and data skill sets are so important, right?

But with the AI world, I think there’s actually now an opportunity to have non-technology hackathons where you can actually get business users together and say, hey, let’s actually just experiment with how do we use these large language models in our everyday life.

And you can think about it a little bit differently and do some prompt engineering, right?

And experiment with that to have some breakthrough thinking around how we can approach our jobs on a day to day basis.

And I think that may be an entry level for a lot of firms if you’re not a deep technology firm, if you’re not building custom solutions or deep in technology with AI, you know, for your firm to really start to experiment with this technology and to figure out what it can do and how to perforate the organization.

Yeah, you know, it’s one way to catalyze change in an organization, right?

So you want to get on the AI journey.

You see pockets of energy in the organization, but you’re not able to bring it all together.

A hackathon could be a good way to get everybody going and give permission to saying that this is a top-tier thing in our company and we’re all going to figure this out together, right?

So I would put it in that perspective also.

But beyond all the logistics, which are super important, because if you don’t get in the logistics, hackathons are terrible, right?

They’re terrible failures.

We don’t care.

It’s very important.

But there are three important, I’ll call them, strategic alignment items that are very important to think of as you’re planning for a hackathon.

One is about relevance, right?

So it has to directly connect with your roadmap or customer pain points, something like that, that is completely relevant to what you’re doing.

The second is more of a balanced focus between innovation and practical implementation.

This is the one that most people don’t get this right.

They just go off on innovation just for the sake of innovation.

You get a buzz in the room, but nothing ever happens to it, right?

So this balanced focus is very important.

The third is what I think of as an integration path into your product, which is also hard to do, but thinking about taking the outcomes and incorporating them successfully into your product.

Otherwise, they just become nice decks, a nice piece of code that is not integrated into your production pipeline and just goes by the wayside.

Just thinking of all of these together sets the stage for a successful hackathon.

I love that.

I’m reminded of Mohan, your conversation with Logan Kilpatrick from the last episode from Google, and he suggested that a lot of people might go to AI in a moment of desperation and just hope that some magic is going to happen, and that exactly what they need is going to come out the other side.

Unfortunately, that’s just not how it works.

I love this idea of a hackathon because it gives you the time and space and that collaborative thinking to figure out, okay, how do we set these things up so that we’re getting magic all the time, not just in a moment of desperation that we think, maybe AI can solve this problem because we all agree that it’s just not how it works.

Yeah, that’s so important.

And with that, I want to double click on something that David said, getting cross-functional teams is really important.

This is not an engineering or design thing, but getting everybody in the company, you may be talking to the customers, you may be talking to the prospects, it may be customer success, engineering, of course, and product design, every function.

Let’s also include our finance friends.

Getting everybody involved in this discussion and making it a true cross-functional team with the customers in mind, potentially having them as advisors or judges could be a great idea.

Just getting them involved for input, the cross-functional teams are very important.

I love that.

I actually have a story from our hackathon where myself, our head of sales, our content manager, one of our senior-

Be careful, Mohan.

She’s about to claim she’s a data scientist again.

Yes.

Marketers were basically data scientists.

Exactly.

All marketers are data scientists, but not all data scientists are marketers.

And in the project that we were working on, it was actually the non-engineers that were, they needed some design things.

And because of Canva, which uses a lot of AI tools, it’s not an AI native platform by any means, but does a lot more than, we’re not really designers.

You’re like, I’m not a graphic designer, but it’s this new tool that I have at my disposal that we were able to be like, okay, y’all tell us what you need and contribute in a different way than we would have been able to in years previous.

And so I think it’s just to your point, the cross-functionality.

And we do laugh because we’re over here designing in a way.

We always joke that our senior engineer was getting some coffee.

We were like, come on, come on, we got to go, we got to go.

And when he sat down and did lightning speed crush, something that would have taken us so much longer.

But I love that idea, the cross-functional nature of that collaborative work.

It’s just, it’s really fun to do together.

I think the collaborative work is so important.

I think the other thing that we haven’t touched on that is important is, is setting a tone for truly breakthrough thinking and experimentation.

I really think that so often in our day-to-day work, we have the blinders on and we’re working within the boxes that we set for ourselves.

I think hackathons can be a great opportunity for both breakthrough innovation and incremental innovation.

But in both, you want to set a culture.

We’re thinking differently about things is actually what this is all about.

We want to challenge the status quo.

We want to break through.

And because of that, we’re going to encourage creativity.

We’re going to encourage thinking out of the side of the box.

We’re going to encourage you to do it differently than anybody would expect you to do.

Right, and I think that is part of the power of the hackathon, is setting time aside to do that and to get out of the route in the everyday.

You know, I really like the, what you said about setting aside time to do it.

In my view, there are two types of organization.

There are doing stuff organizations and there are planning stuff organizations.

Right, the planning stuff, they just plan and plan and plan and plan, right?

So they never get to it.

The doing stuff, hackathon is really kind of helps you become more of a doing stuff organization.

And there are always people who are quiet, you know, who generally don’t participate in conversations.

But they have an opportunity to shine because, you know, they can do stuff, right, in the hackathon and shine.

So it brings everybody together.

So it’s a really awesome cultural impact if done well.

Well, we also should acknowledge now that so many companies are virtual.

I do think it takes a moment when you’re doing these hackathons to kind of settle in to, okay, how do we work together in this different context than we’re used to?

Because it is different, you know, people in person, you don’t have to kind of wait your turn to talk.

You know, it’s more organic.

You get to see how people actually do their work.

You know, in the old days, you would just walk past their office and kind of get a sense of how they go about their work.

We don’t really get that today.

And so I think that you kind of have to warm up a little bit.

I feel like some of our first hackathons out of the gate, you know, those first sessions, actually, I remember, I actually have really terrible feelings about the first thing that we did because…

Really?

Yes, because you two, this is a hot take for this episode.

We presented our ideas and y’all voted My Teams Project last place.

I don’t know that that’s our call.

I think you should have slipped it up a little bit, Courtney.

Still to this day, one year later, I think you two were absolutely wrong.

So in that moment, y’all learned.

She says she doesn’t look grudges.

She’s so competitive.

That’s what y’all learned that first hackathon.

But I think it’s so interesting in this virtual environment, kind of how those work when you get everybody together in the same space.

No doubt.

No doubt.

It’s so powerful.

So have you two changed your mind about my team’s epic project for me?

We should have scored it even lower.

Don’t even answer.

Do y’all two even remember that?

Because I have a scar from that.

There is enough psychological safety that you brought it up again, but I think the answer is the same.

Hopefully, next hackathon, you can do a great job.

Listen, I’m going to keep bringing it up.

It is never going to die.

David, Mohan, hopefully, we’ve inspired everyone out there to go host their own hackathon.

Thank you for all of your wisdom of 50 plus hackathons between the two of you.

Thank you as always.

Mohan, how’d she do on this episode?

Should we vote on that too?

Don’t you, Avin?

Yeah, but we won’t disclose.

Pete Buer joins us, as always, to break down the business impact of some of the latest and greatest in AI news.

Hey, Pete, how are you?

I’m good, Courtney.

How are you?

I’m doing great.

This week, let’s unpack the story from Wired.

The Humane AI Pin has already been brought back to life.

Pete, I’m late to the game here.

What happened to Humane, and what’s the takeaway for business leaders?

So first, a trip back in time to secure a reminder of the Humane story.

A couple Apple employees raised a ton of money, launched a splashy product.

It was an AI Pin that allowed you to take pictures, display messages on your hand, and direct a chat bot to do your bidding.

All without, again, having to dig into your pocket and drag out your phone.

Unfortunately, kind of like our friend, the R1 Rabbit, which comes up more often than probably it should.

The device was a flop on delivery, didn’t live up to concept.

A lot of features didn’t work as build, and once you had it, and were pinned, and were walking around living your life, you realize it kind of didn’t make all that much of a difference to your day-to-day.

At least that was the experience played back by customers.

Long story short, Humane sold the assets of the business to HP, and very recently bricked the device forevermore.

Or so they thought.

The AI pin is back in the news now, short time later, because a group of committed hackers were able to jailbreak the device.

These are people who believed in the promise of the product.

They loved the notion of capturing video and voice without having to mess with their phones, and they see a future where hands-free, voice-driven control of the applications that serve you in life is kind of the way to live, and they want to make the thing work.

Which is cool, and a little bit sad after the fact.

What’s the takeaway for leaders?

It’s less an AI lesson and more a product lesson.

You got to meet your market where it is.

On the one hand, look how determined this set of gifted hacker slicks is as they get into the device and start to make it work the way they were hoping it would originally.

On the other hand, there’s the massive rest of the market that just kind of showed up with a meh on the thing.

Especially for a $700 price point device, he may miss the sweet spot in the market, and that’s sort of sad.

Good object lesson for the rest of us as we bring new innovations and products to market.

You know, in hindsight, I wish rather than them being sold to HP, maybe they should have combined forces with the Ray-Ban meta glasses, because I don’t know if you’ve seen those in operation, but it feels like that’s a useful way to have a wearable, and then you add the AI component, which meta may already be on that.

Maybe that’s why they didn’t buy this.

If I had my wish list, I would love to pair those two up and see what would happen.

I agree.

Well, Pete, thank you as always.

Thank you, Courtney.

Thanks as always for listening and watching.

Don’t forget to give us a review on your podcast player of choice.

And we’d really appreciate it if you would take the time to share this episode with someone you know would love it.

Maybe someone that you’re thinking about having a hackathon with.

At the end of every episode, we like to ask one of our AI friends to weigh in on the topic at hand.

So, hey Claude, this episode, we’re talking about tips for business leaders who want to run an AI hackathon.

Any advice?

For a killer AI hackathon, give teams clear challenges, top-notch AI resources, and expert mentors who can guide them from cool concept to working prototype.

Make sure your judging rewards both technical creativity and real-world problem solving.

And now, you’re in the know.

Thanks as always for listening.

We’ll see you next week with more AI applications, discussions and experts.