When the Answer Finds You: Scaling Support with Karen Holliday
When the Answer Finds You: Scaling Support with Karen Holliday
Imagine a support agent lost in a maze—too many tools, not enough answers, and frustration simmering on both ends of the line. What if the right answer could appear before the question is even finished, using tech designed for knowledge to flow effortlessly? Join Karen Holliday, VP of Services and Support, as she dives into where support systems break down, and how integrating Knowledge-Centered Service can truly change a company’s culture.
Transcript
Pete Wright:
A customer calls support, they’re frustrated, they’ve been transferred twice, three times, and the person on the line, they’re trying their best. But behind them, the system is straining. There are too many tools, too little clarity, no single source of truth. The agent spends minutes searching, guessing, apologizing. Now imagine the same moment, but this time the answer appears before the question is even finished. It’s not magic. It’s design, it’s culture, it’s knowledge in motion. Scaling support isn’t about adding more people. It’s about removing friction for the people you already have. It’s about building a system where knowledge flows effortlessly between people, across teams, and into every interaction. Karen Holliday knows this better than most. As VP of Solutions consulting at Upland Software, she helps organizations do just that: connect their tools, activate their knowledge, and scale support the right way. I’m Pete Wright. This is Connected Knowledge. Karen, welcome to Connected Knowledge. I’m so glad you’re here.
Karen Holliday:
Thank you. Happy to be here.
Pete Wright:
Let’s start exploring sort of the foundational idea of our conversation. When a support team grows, there are many areas that need to scale along with just the people. Of course, there’s the people, there’s the plant, there’s also the systems, the knowledge that comes with it. And I’d like to know from your perspective, what breaks first?
Karen Holliday:
That’s a really interesting question. I find that most people want to come in, come on to an organization and be contributing as quickly as they can. They want to make sure that they have everything they need to be able to do their job. And so really what breaks down is information. They can’t find the information they want to do their job, they can’t find where to find it, they don’t know who to ask, and they end up getting frustrated really quickly. And I think that that’s the biggest part of trying to onboard and scale up a support team and any kind of team is really just trying to access the knowledge they need to do their job. And they want to feel contributions and feel satisfaction in what they’re doing, and they really don’t feel like that when they can’t find what they need to do.
Pete Wright:
Sure. It seems like that was probably a leading question given who you are and what you do, but I do think it’s important to look at how our institutional knowledge actually applies to each of these elements, to our human capacity, to our ability to create consistency across teams, to be able to fight burnout for agents who are constantly stressed in a high burnout field. And I would love to hear from your position when you’ve seen knowledge management done right, what sort of operational changes or efficiencies stand out to you the most?
Karen Holliday:
Well, I’d say the biggest thing that I see standing out is that the people who work with me are happy. They feel that their contributions are taken seriously and their happiness and their joy in being able to do their job flows into the customers and the customers are happy. So for the most part, bringing knowledge forward and knowing what you are doing at work makes you feel happy and feel productive and feel valued. And I think it’s really down to hiring really dynamic and interesting people who want to do good work. And the best way I can support them is to make sure that they have everything they need to do their job. And that’s everything from the right computer to the right tooling and the right systems and the right information that they have.
Pete Wright:
We’ve talked on the show a number of times about AI and the way AI is changing how we think about knowledge. And for us, it’s clearly more than a buzzword at this point. It’s not so quietly transforming the way support teams access and use knowledge in real time. So let’s talk about some of the ways that you are seeing AI reshaping knowledge management. Where do you see the most impact in the technology and how it impacts our knowledge workers, our support teams?
Karen Holliday:
So it’s interesting. I was thinking about this the other day that I find that the AI machine for support is similar to when we were going from a handcart to getting to use a forklift at a plant. So it makes us go faster, we can do a lot more at the same time, we can get much more efficiency. So I was thinking about that, that it’s kind of in conjunction, when the industrial revolution came around, we kind of thought, hey, the machines are going to replace the humans. But then we realized, oh, the humans are available to do much more valuable work. And I think AI is very similar where it helps us with the content creation, it helps us with the content retrieval, it helps us looking for duplicates, it helps us with everything to do with solving a customer’s issue. And so if we use it like a forklift and it allows us to do more quicker, more efficiently in a better way, that’s what I think AI is doing for support teams. I think it’s allowing us to be supercharged versus having to do things in a bespoke manner.
Pete Wright:
Do you see a time where the forklift doesn’t need a person?
Karen Holliday:
No, I think we always believe that you need a human in the loop. There’s certain ethical things that only humans can do. There’s certain contextual areas that only humans know, and to take the knowledge that AI serves up and then take it to the next level and create something new, which is what support agents need to do in a highly complex SaaS support environment, you do need that human in the loop but we can use all the tooling we can get. So that’s where I think AI comes in. It may support us so that we as humans are able to act at a higher level and we don’t have to spend our time doing the menial tasks that aren’t that interesting and can be done by the AI machine.
Pete Wright:
I love the forklift metaphor, and I’m going to use that because I think it makes a lot of sense. And I also think there’s something about the way the forklift begins to understand my behavior, my needs maybe before I even get there. I notice this a lot. I mean, as we’re recording this, many of the public-facing tools are now introducing memory. So they remember who I am and my behavior and what my needs are. And it’s a little bit alarming the first time it says, “I know you did this last time, you asked a question similar. Do you want me to do the same thing again?” And the answer is yes. Yes, I do. Of course you’ve gotten ahead of me. And so I am consistently blown away by how effectively I can use this forklift.
So let’s talk about how well the forklift works in a few more concrete examples from the knowledge space. We’ve got chatbots pulling instant answers, we’ve got AI assistants surfacing just the right article at the right time. I know we’ve got to talk about some of the tools from Panviva and RightAnswers in how AI is helping agents do their jobs more effectively. What are you excited about in these tools?
Karen Holliday:
Yeah, so I think the first place to start with what I’m excited about is knowledge creation. I think using AI assistant in our tool, so Panviva and RightAnswers, it allows us to create contextual, very quick articles that allow us to be able to foster more information into the knowledge base quicker, and we make sure that there aren’t duplicates. We used to have to use keyword searches to see if there were duplicates. If you didn’t hit the right keyword, you would never find it. Now we have this AI tool that allows us to vet new creation to start so we’re not filling up our knowledge base because every knowledge manager knows that you can have 10,000 articles, but maybe only 1,000 of them are useful and you don’t know which 1,000 that is. And AI can help you streamline that and have what’s there is actually relevant, accurate, and searchable and findable.
I think the second part that excites me a lot with AI is obviously the retrieval aspect. So when I use generative answers, when I use a neural search, I get a better hit ratio, I can use a hybrid search, so I can use my old school keywords, but I can also use some questions and it gives me the best of both worlds. I just love that we can still use what we had previously and bring it forward and use it today in just the same way, but in an improved way. And we’ll get better answers and answers that combine multiple knowledge articles because you might have a question that has a little bit from multiple sources and you need to combine that and GenMasters does that for you.
Pete Wright:
So I think you’re describing the kind of time-saving efficiency that we get when seeing these tools and seeing how they’re properly integrated. When you look at that integration perspective, what do you see as what is lost when they’re not integrated? Because I think right now we have so many AI tools that people are using, their stack might include multiple AI conversation partners. And I’m trying to make sense of where that’s going to settle out. Are you still seeing people who are searching their knowledge management corpus with one tool and still having to come up and open ChatGPT to actually do some resource work on a specific bespoke situation?
Karen Holliday:
Yeah, that’s a great point. We do see folks that need to do that, that have to use multiple tools, but we don’t need to do that. And in our tool sets, RightAnswers, Panviva, it’s all in one pane of glass. So you don’t have that time spent for the agent to context switch to try to determine what they need to bring forward and what they don’t. It’s all in one place. We can use these tools to go out and look on all of our different knowledge platforms, not even just our own. We can have them search and retrieve information and bring it all back into our single platform so that we don’t need to go back to Confluence or back to Jira or back to Zendesk or back to something else to find that answer. It will bring it all together for us. And I think that that makes such an impact to the agent who doesn’t need to know what system a particular piece of information is stored in. They just need to know where they have to go to get it.
Pete Wright:
Right. Again, this goes back to the idea of removing friction. As soon as you’re switching tools, as soon as you’re context-shifting, you’ve introduced friction, which slows down the response time, slows down the call time. Last week, this makes a perfect transition. Lana Kosnik was here and introduced us to Knowledge-Centered Service, KCS. She gave us a great lens into the philosophy of KCS, but given your position, I’d love to hear your language around KCS so we can dive into some of Upland’s tools. So in your own words, what is KCS and how is it different from traditional documentation models we might’ve grown up with?
Karen Holliday:
Yeah, so for me, knowledge-centered support or knowledge-centered service is really a methodology that integrates the creation and maintenance of knowledge into just your daily workflow. And the key is the daily workflow is that it is not something that you have to do on top of your daily tasks. It’s part of your day, and that reduces the friction. And it’s really capturing, structuring, and reusing that knowledge that is the key to knowledge-centered support. In terms of how it used to be, it was an overlay. It was something that you did as an afterthought to whatever task you were working on, but now it is part of our daily task and our daily workflow, which makes it much easier for people to get behind and much easier for them to do that work.
Pete Wright:
Sure. You said something really important, which is we’re making it part of their day. With KCS embedding knowledge creation into the act of solving problems, that seems to require, or it at least generously hints at a need to change the way people think about their day, change the way they think about solving particular customer problems. And that implies a culture shift that is sometimes not easy to crack. How do you see organizations adapt when they are now tasked with thinking about knowledge as a part of their overall job, not just being a resource that they view into?
Karen Holliday:
Well, it’s interesting. We went through this transition just over five years ago here at Upland, and we had to do all of the same things that every company needs to do. And the most interesting part I found about the transition is that it took an introduction and a champion within the organizations, but people came along because they saw the value. It wasn’t a tough sell, when people started to see, “Oh, the knowledge is there and I can use it and I can contribute to it.” And you know what? It’s also a really great way to see how you progress through your career. So KCS also has a framework that allows our team members to progress through the stages of their competency with KCS.
So they get to go from candidate to contributor to coach. And so it allows you, even if you don’t want to be a manager, you don’t want to progress that way, but it allows you to progress through your career in different competency levels and you can help others around you. And I think that adding that really adds some career satisfaction to people and people who are really great coaches, and it’s a real self-driven journey that people are on. And with Lana’s support as well at our company, she’s a wonderful KCS practitioner. She helps us learn how to make that progression. And we have many success stories that make this really a great story for Upland. We’ve improved our resolution times, we’ve improved our response times through using this methodology. So I think those are the biggest things.
Pete Wright:
Take me back. What were you doing at the time? Were you the champion that was leading the charge or were you a recipient of all this great wisdom?
Karen Holliday:
So I was not the champion, but I championed within my organization. So we’re very lucky at Upland, we have a shared services organization that our KCS team is part of. And so as a leader in one of the lines of business, I championed it for my line of business and we made sure that we adhered to what’s going on there.
Pete Wright:
Well, this is my, I think, fundamental question is, from your experience, you talk about all the successes that Upland experienced, what was it that turned you into a champion? Do you remember the aha moment that said, “Oh my goodness, this is going to impact us in an incredible way and I’m on board?”
Karen Holliday:
Yeah, definitely. So when we kicked off KCS, we were struggling with the same issues that many companies have. I could see that the team was struggling with answering questions. We had long-running tickets, we had disparate systems. I didn’t know where to look for the information. So I don’t know how anybody on my team was going to know where to look for the information. I didn’t know how to solve an issue or who to ask. And as we started to build those out and realized that they were in different systems, as we looked at it and we said we could bring this all together and have one source of truth, that for me, it was the aha moment, that I know where to go, where to get the information and how to act on it simply from going to one place. And it made everything for me very crystal clear.
Pete Wright:
It’s beautiful. It’s a beautiful story and a transition. And from my understanding in talking to Lana, it’s not that long of a transition. Once you adapt and adopt, it doesn’t take that long to get people on board. Is that your experience?
Karen Holliday:
Yeah, I think people see the innate value of it, and it’s not really outside of what we have to do anyway. You always document, people used to have yellow stickies all over their screen. You had, “Oh, don’t forget the password for this. Don’t forget the login for that.” And you had it everywhere, and now you don’t need all those yellow stickies around your screens anymore. They’re all in one place. And I think folks started to take that tribal knowledge we used to call it or team knowledge, and they started to translate it and write it down so everybody could see it. We’re not all in the same office anymore. You can’t walk over to your neighbor’s cubicle and ask them a quick question and go back. So we took all of that information and we put it online, and now you can be at the same level as someone else, even if you’re not sitting next to them.
Pete Wright:
This conversation, I mean, we’ve talked about the components, AI, we’ve talked about the flexibility that comes from being able to use hybrid search. We’re talking about knowledge-centered support or knowledge-centered service. All of these are the components of a scaling, a support scaling operation. And I’d love it if we could bring it all together. What are the core capabilities that Upland is bringing to a support team that’s ready to scale smartly? How do you pitch that?
Karen Holliday:
Well, I think that the key tools are our software platforms. So we have two very key knowledge platforms, Panviva and RightAnswers. Those platforms, depending on the business need, are the right starting point for any knowledge journey. I think the really interesting part is that we have integrations with the pre-existing tools that are there. So you don’t need to get rid of what you have already. You’re going to use it in a different way or in a more full way. And I think with also augmenting the integrations, the software platforms with the AI capabilities like creation, like search, retrieval, that brings it all together into one place so you can find it.
I think the other thing that’s interesting as well, if companies want to start on a journey is that no one is using the big thick binders anymore on their desk. Everyone’s got some kind of knowledge somewhere in their system. Everybody does. But it’s how do I leverage it? How do I bring it together and how do I make it so that all of these tools work symbiotically together, whether I need to use backend processes to bring it together or anything else, AI, API searches, any kind of integrations. I think the right way to move forward is to think about knowledge as a holistic platform. And it doesn’t have to be one thing or another, but you need to bring it together so that all of your folks have one place and one source of truth.
Pete Wright:
I recognize sometimes the sensitivity around naming names, but I would love it if you want to anonymize a story. I’d like to hear about a favorite client, a client that captures how these ideas show up in the real world. Can you tell us about someone for whom it’s clicked?
Karen Holliday:
Yeah. So recently we have done a new AI proof of concept with one of our leading financial institutions. So a very large financial institution has lots of knowledge at play, but hadn’t gone down any of the AI path. So as we were able to work with them and look at how Upland support solutions could really improve it, we saw a 40% reduction in average handling time for their support tickets, which was phenomenal. They leveraged the AI-driven insights and KCS methodologies, and they achieved this operational efficiency that far exceeded actually even what I was expecting them to achieve. So it was just a really fun time too. Their teams really got on board with using these new AI functionality and really demystified it because the financial institutions are usually the later ones to change, usually slower in adoption. And the fact that this company went for it and is now adopting it company-wide is really a testament to the way this all works together.
Pete Wright:
Such an interesting observation that in this case, using AI as the example, this adoption moves so quickly because of the pace, AI can respond and adapt to your sort of knowledge corpus. And that I imagine accelerates change in ways we’ve never experienced. Links in the show notes for Panviva and for RightAnswers. Anything else you would like to make sure that we share with the good listener today?
Karen Holliday:
I think it’s just that don’t be scared of the new changes in our world. Folks who were worried about the Industrial Revolution, we were worried about moving to the cloud, we were worried about all of these things, and AI is just another tool in your tool set so that you can focus on things with your knowledge methodologies, and you get to focus on what’s really more important and more interesting. So I think that that’s the biggest thing for me.
Pete Wright:
Great. Karen Holliday, thank you so much for your time today. Appreciate your participation and your wisdom. And thank you everybody for downloading this show. We appreciate your time and your attention. Don’t forget, link in the show notes. To ask us questions, if you want to submit a question to the show, we’ll answer it on an upcoming episode. We’d love to hear your feedback. On behalf of Karen Holliday, I’m Pete Wright, and we’ll see you right back here next time on Connected Knowledge.

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