3194: Smartsheet: The Future of AI in Project Management

[00:00:03] What happens when AI meets Project Management? Can AI truly boost productivity, live up to the hype, without replacing the essential human skills that drive successful projects? And how do leading companies ensure responsible AI adoption without compromising their data security?

[00:00:26] Well, my guest today, Maya McLean, Vice President of Product Management at Smartsheet, is going to help me in answering some of these questions. And if you've not heard of them, Smartsheet is a platform that has revolutionized how organizations manage projects, programs and processes. But what put them on my radar is AI has become a key player in streamlining operations.

[00:00:50] And it was Smartsheet's approach to embedding AI tools directly inside the workflows. And achieving great results and enhancing efficiency, but also unlocking richer data insights. They're just a few of the many reasons why I was excited to invite Maya onto the podcast today. Here's another quick stat. 63% of eligible Smartsheet plans are already leveraging these AI features.

[00:01:19] And this is one of the things that always interests me because we can create all the tools in the world. But the organization's culture and ensuring that they can adopt these tools and that they're intuitive, easy to use. They're often the hurdles that businesses fall over first. So today, Maya's going to be sharing how Smartsheet's AI solutions are designed to complement human expertise

[00:01:42] and enable human project managers to shift focus from those manual tasks to the more strategic decision-making tasks. I will also explore how AI can combat burnout by providing project visibility, identifying issues early and ultimately reducing frustration. All while supporting scalable operations from that frontline worker all the way up to the CEO.

[00:02:10] But hey, I am the overcautious ex-IT guy and with technological advancements come great responsibilities. So Maya will also explain Smartsheet's commitment to data security, ensuring that there isn't any co-mingling of customer data for AI training purposes.

[00:02:28] And hopefully we'll also have a chance to dive into the future of AI and project management from agentic AI enabling context-aware strategic planning to more personalized onboarding tailored to specific user needs. So all in all, can AI-powered project management tools reshape how businesses achieve those outcomes and ensure that projects get delivered successfully and on time and under budget?

[00:02:57] And how do we balance AI automation with the human creativity and problem-solving and vision that projects rely on? Well, enough from me. I don't have all the answers. Time to get my guest on, Maya, who hopefully has. So a massive warm welcome to the show. Can you tell everyone listening a little about who you are and what you do?

[00:03:20] Thanks, Neil. It's really exciting to be here. So my name is Maya McLean and I am a VP of product management at Smartsheet. I've spent most of my career in productivity software, either in SaaS-based businesses or e-commerce. And I've done it at places like Microsoft, Cisco WebEx, and even a retailer in the United States called Nordstrom. So a lot of my career has been going between different segments, both consumer and enterprise.

[00:03:48] And at Smartsheet, I lead a team called the core work management team. And we focus on our core work manager persona, really looking at how do we get people to come into Smartsheet, understand the value of Smartsheet very quickly, start using that value, and then be able to showcase that value out to their stakeholders. And it's a fundamental part of our business. So it's a lot of fun. I love what I do.

[00:04:12] And at the core of what I do is I listen to our customers and really try and understand what they need and translate that into product experiences that they can use and that make their lives better. So outside of work, my husband and I have four kids, and so they keep us pretty busy as well. I bet. Incredibly busy, I suspect. And of course, we've entered the third year since the world went all in on AI or generative AI.

[00:04:39] But I think as we enter this third year, there's now much more of a focus on things like ROI of the technology. What kind of value? What improvements is it bringing? Measurable improvements at that. One of the things that put Smartsheet on my radar is you've got this integrated suite of AI tools that are playing a key role in project management. So again, if we drill down on this value add, how does embedded AI differ from maybe standalone solutions?

[00:05:07] And why do you think it's so essential for successful project delivery now? Yeah, I think for a tool like Smartsheet, embedded AI is just fundamentally better than a standalone solution. When you think about the problems our customers are facing within project management, customers are looking for a way to add value, like you said, to their organization. And so we fundamentally just listen to our customers. Smartsheet has always been an enterprise-grade platform.

[00:05:37] And so when AI came on the scene, we said, well, how do we make it an AI-powered enterprise-grade software? And realistically, that's about meeting our customers where they are with the workflows that they're already doing within Smartsheet and making those easier. So for example, if you take formulas, they are one of the most powerful things you can do in Smartsheet. They enable you to move data around. They enable you to do calculations. They also have a pretty large learning curve. They're hard to do. They're hard to learn.

[00:06:06] But if you can't learn them, then you don't get to unlock all of that power. And so we created a contextual embedded AI generate formula that allows you to learn, to just natural language ask what you're trying to do, say what formula you're trying to build or what you're trying to calculate, and we'll calculate it for you.

[00:06:26] So this automatically takes out the friction of learning formulas, and you can automatically harness all of that power that Smartsheet has very quickly, making it way easier to get your project done. And it's not just for new customers. Like I use Generate Formula all the time, mostly because it enables me to do more faster without having to do the tedious work of building out the formula and making sure I have all this syntax right.

[00:06:51] And it gets the outcome that I need, which is I get the data where I need or I get the calculation where I need a lot faster. And you mentioned data and formulas there. And I think many businesses struggle with what I think you refer to as data mess. So how does Smartsheet's AI tools, how does it help organizations better streamline data management and turn information or that data mess into more actionable insights?

[00:07:18] Well, if you think about why the data mess exists, you know, the pace of work is going faster than most organizations can adapt. And there are reasons for that. You know, there's multiple tools for collaboration, whether it's a tool like email or text messaging or messaging platform. And yet silos still exist between departments and teams within organizations. There's also, you know, all types of tools within tech stacks to do the same thing.

[00:07:46] And yet inconsistencies exist or inefficiencies exist that drain customers. And all of this leads to so much data across so many different systems without a clear understanding of the source of truth. And when you don't know where your work flows, it becomes really hard to manage all of this and actually to get outcomes that you need. So Smartsheet is really the place where your work flows. And it's the place where all of that comes together.

[00:08:12] It becomes the epicenter for your digital workplace to understand how work is flowing and where is it going. And once you centralize it, you have an extreme ability to get the insights you need from all of that data. And it's insights not just about how is my project going, but it could also be insights about what should I do next and how is this work flowing within my organization.

[00:08:36] And then you can present that to your stakeholders so they understand the data-driven decisions that you're making and where they're coming from. So it really goes back to why the data mess exists to begin with. How Smartsheet really helps that by becoming the epicenter of your digital workplace. And then AI on top of that just makes it even better by allowing you to pull the insights you need from that data quickly. And yeah, quickly. Love that.

[00:09:05] Of course, elsewhere, burnout and team challenges are growing concerns in the world of project management. I've got a few friends working in the industry and they're telling me about this stuff all the time. So how can AI-powered tools identify some of those issues early before they become a problem, be more proactive than reactive? And indeed, what role do you see Smartsheet playing in minimizing burnout while also maintaining productivity? Again, big balance. Yeah, I think it is a balancing act.

[00:09:34] And I think burnout exists because there's a lot of factors that are playing within organizations that are not allowing them to achieve the outcomes that they want. There's a spread of the workforce. There's multiple generations within the workforce. And all of this leads to actual real problems within an organization. Problems of missed deadlines. Problems of missed opportunities. And I think that plays into the burnout of project managers as they're looking to get their projects done on time.

[00:10:04] And it's just too hard. And that burnout is what fuels a lot of people to say, like, this isn't working. Our tools are not equipped to handle the pace of work and handle how fast work is moving. So Smartsheet allows teams to scale work across their organization. It doesn't matter who you are within the organization, from frontline workers all the way to the CEOs.

[00:10:28] We give the visibility to those who need it to make sure everyone is marching in the right direction and marching towards the same goal. And I think when people achieve their outcomes, the burnout doesn't feel – you don't feel the burnout because you're actually achieving what you're trying to achieve. And so, again, we really understand our customer problems and we understand how to apply AI to those problems and not the other way around. So that's why our AI tools have just been practical in nature. They're about how do you pull insights out.

[00:10:57] They're about how do you get started quickly. Or how do you even get the help you need within Smartsheet to move faster. And I think all of those things contribute to you getting to your outcomes a lot faster, which reduces the burnout you see in teams. 100% with you there.

[00:11:12] And if we dig a little bit deeper into this fine balancing act that every organization is grappling with at the moment, delivering a successful project ultimately requires balancing speed, accuracy, and, of course, collaboration amongst those many different project resources. So how does your AI suite at Smartsheet, how does that support teams in achieving that balance, especially in fast-paced business environments that are demanding more with less in many cases?

[00:11:42] Yeah, and it's only getting faster. I think there will be an increasing pressure on teams to move quickly. And that pressure is only going to get more and more as people understand what they can do in this work environment with AI and with their workforce stronger by spreading it across geolocations. And as business gets smarter, the amount of data that organizations need to parse just gets bigger and bigger, and it can become increasingly overwhelming. And that, again, leads to missed projects.

[00:12:11] It leads to working on the wrong things. It leads to delays because communication can't happen across. So when you think about Smartsheet and think about it being the place where your work flows, the place where everyone comes together to collaborate on how a project is doing, you really need to be able to visualize what's going on. And so we have an AI tool called AI Insights. And what this does is allow you to pull the data out that you need to really understand how a project is doing.

[00:12:40] You can ask it things like, how many of my items are off track? You can ask it, how many items does Neil have? And is he on track? And that automatically allows you to understand what's going on, showcase it in a chart or a graph, and put it on a dashboard for your stakeholders to really understand what's going on as well and understand why and how you're making data-driven decisions. Our customers are telling us this works.

[00:13:04] I think across our suite of tools, we see about 63% of our eligible plans actually using our AI tools to derive value from Smartsheet. And apologies for being the overcautious ex-IT guy, but with AI adoption on the rise, responsible and strategic use is more important than ever too. So what advice would you give businesses looking to integrate AI in a way that adds value without introducing unnecessary risks?

[00:13:34] I mean, that's a great question. I think for an organization, their most important assets are their people and their data. And we understand that customers are entrusting those assets to us, and they need to keep their people and their data safe. And as an AI-powered enterprise-grade platform, we need to make sure we give you that trust back.

[00:13:56] So our approach to responsible AI has really been anchored on the principle that customer data will not be commingled with each other, and no customer data will be used for training data. And I think this gives our customers the trust they need to understand that Smartsheet is valuing their most trusted assets at just as much as they are. And we're partnering with them to keep it safe.

[00:14:18] The other thing I'd say is, as businesses integrate AI into our platform, we do, as a business who integrates AI into our platform, we really look at our third-party providers that we're using and really understand that they meet the same standards that we apply to our business to make sure that we extend that trust to the third-party AI providers that we're using.

[00:14:42] And one of the things I always try and do on this podcast is give my guests a way of busting a few myths, laying to rest some of those frustrations that they may read on their news feed. So in your experience, what are some of the most common misconceptions that businesses might have about AI and project management? And how do you address these misunderstandings at Smartsheet? Yeah, I mean, AI is so powerful, and so there's bound to be misconceptions about it.

[00:15:09] I think one of the biggest ones we hear is that AI will replace project managers. We'll be able to do what project managers can do from start to finish. And the reality is that's not true. I think humans, we play a critical role in project management and understanding what's working, what's not, and bringing the creativity to project management. And so I think AI is a powerful tool. It enables you to do things that you couldn't do.

[00:15:34] But what it does allow project managers to do is spend less time on kind of task-based management so they can spend more time on strategic management of their projects. So as opposed to looking at what's on track, what's not on track, they can start to shift their focus to what should we do and why should we do that? And how do I showcase those decisions to my stakeholders so that we actually are moving the business a lot faster to bigger and better outcomes? Yeah, I completely agree.

[00:16:02] I think project managers, the human project managers, they've got so much to offer in delivering that strategy and focusing on that grand vision as well. That's something that AI cannot do. And AI's role in project management will continue to evolve. So I'm curious, what are you seeing here? What innovations or trends in AI do you think will have the biggest impact on how teams manage projects in the years ahead? Anything that you're seeing taking shape here?

[00:16:28] Well, I think one of the things I'm most excited about is the emergence of an agentic AI. Today, when you think about what AI can do and what people are using AI for, it is very much based on logical-based decisions that it's trying to make for you. But when AI can start working on your behalf, that gives you the ability to spend even more time on those strategic decisions and less time on those kind of logic-based decisions.

[00:16:55] So if you think about as a project manager, you're looking to say, well, is my project on track? And you can ask AI this today within Smartsheet. But that's a very logical thing. You are looking at how many tasks you have, how many of them are overdue, and based on that, what's the risk? And that's kind of a calculation. But think about if you could say, well, what projects should we work on?

[00:17:20] And AI can, on your behalf, give you a plan for what is the right strategic projects to work on and who are the right people to work on it. This requires some context, though. You need to know what projects are strategic and why. You need to know who's good at doing what type of projects and why they're good at it. When's the last time they did that type of project? Were they successful? Things about, you know, who's going on vacation and who's not and who's about to get a promotion.

[00:17:50] All of that context plays into how do you map out your organization against your strategic projects and the people who should go work on them. And that becomes a very powerful tool. You still need humans because humans need to be able to go in and say, yeah, yep, that makes sense or tweak it. But AI has taken out all of the guesswork and on your behalf, giving you a plan that you didn't have to spend hours doing.

[00:18:14] And that's super powerful and one that I'm really excited about when we think about AI and where it's going. I'd also say today AI is really good at helping you take some friction out of creation and getting things started within Smirchy. But imagine if you had an agent that could come alongside you and help you onboard in a very personalized and very customized way within Smirchy.

[00:18:39] And those are the type of things I think we'll see in the future that are even more exciting about where AI is going. Exciting times ahead. And on a personal level, with your engineering background and product expertise, how are you personally approaching the challenge of designing AI tools that are both powerful and accessible for a wide range of users? Because we've made it sound very simple today, but your challenge is equally quite high too, right? Yeah.

[00:19:06] I mean, I got into engineering because I actually saw a lot of creativity in it. Building tools for people to make their lives better is my personal mission in life. And I think you make people's lives better by, you know, making them smile, making them more efficient, or making them better connected to the people around them. And so I think with anything that I do, it's about listening to the customers, understanding their needs, understanding what's working for them and what's not,

[00:19:35] and marrying that with the best possible experience within the product that's simple to use and simple to get started with and simple to extract value from. And so I think we've approached AI in exactly the same way. They're powerful, but they need to be integrated in a way that's seamless and not something that feels cumbersome to learn or cumbersome to understand.

[00:19:57] So this is definitely the purpose and appeal of no-code, low-code technology that's powered by AI, and that's fundamentally what Smartsheet brings to our customers. Well, thank you so much for taking the time to sit down with me today, share your insights on the role of AI in project management. But before I let you go, I'm going to ask you to leave one final gift with everyone listening and have a little bit of fun with you here.

[00:20:21] I always ask my guests to leave either a book to our Amazon wishlist that means something to them, or a song to our Spotify playlist. I don't mind which, but what would you like to leave everyone listening and why? Well, I'm a big reader with all my extra time between my four kids. But I think one of the biggest books that has transformed me or has been really important to me is The Dip by Seth Godin.

[00:20:46] I think I love Seth Godin, but also The Dip fundamentally talks about anything worth doing is hard, and there will always be this moment where you have to decide, is this worth doing? And do I go through The Dip, or is it worth giving up, which is also kind of a strategic thing that you have to decide as well. And so fundamentally, I think it has changed the way I think about hard things and has been really important to me in my career. Fantastic. I will get that added straight to our Amazon wishlist.

[00:21:15] I'll be checking that one out myself. And for yourself and Smartsheet, anyone wanting to find out more information, having listened to our conversation today, where would you like to point everyone? So Smartsheet.com is a great place to kind of check out what we're doing and what's latest. We also have Smartsheet social media channels that are really great at kind of showcasing where we're going and what we're doing. And then for me personally, you can check me out on LinkedIn. That's the best place to kind of get in touch with me. Awesome.

[00:21:44] I'll make sure there's links to everything so people can find you nice and easy. We did cover a lot today from the importance of embedded AI in project management, how it can help customers solve that data mess, identify team challenges, minimize burnout and deliver successful projects. There's your ROI. There's your measurable impact right there. And also for sharing your perspective on how businesses should be using AI both responsibly and strategically and even leaving us with a great book.

[00:22:14] Thank you so much. Thank you. So from AI powered project insights to responsible data practices, Maya McLean today, I think, has offered a deep dive into how Smartsheet is redefining the future of project management. I think their focus on embedding AI seamlessly into workflows rather than forcing new processes.

[00:22:37] I think this demonstrates why AI works best when it enhances rather than replaces human expertise. And it's also clear AI is not here to take over the project manager's role, but it's here to amplify human decision making, helping teams achieve faster outcomes while reducing the risk of burnout.

[00:23:00] We also have agentic AI on the horizon, capable of offering context-aware recommendations, personalized onboarding. I think over the next few years, we will see some exciting developments in how businesses both plan and execute their projects. But what do you think? How do you see AI powered project management becoming the new standard? Can AI take strategic planning to new heights?

[00:23:27] Or will human intuition always be that key ingredient? I suspect it's a combination of the two, but I'd love to hear your thoughts on this. Share your insights. Join the conversation today by emailing me, techblogwriteroutlook.com, x Instagram, LinkedIn, just at Neil C. Hughes. And my website, if you'd like to work with me, is just techblogwriter.co.uk. But that is it for today. Huge thank you to today's guest. But absolute breath of fresh air.

[00:23:57] Love the work that she's doing. And hopefully you'll join me again tomorrow. I've got another guest doing something very similar, but in a different industry. How does that sound? Good. I will speak with you all then. Bye for now. Bye for now. Bye for now.