I recently got the opportunity to ask Greggory Wright, Strategic Learning Partner at Southwest Airlines, for all the details on his team’s challenges, agentic AI, learning strategy, and his Learning Leadership Conference sessions:
Q: What’s been your Learning & Development career journey?
A: My learning and development career journey has definitely had its mountain peaks and valleys. It all started in middle school or junior high, when I was always leading groups through learning things, whether it was music, math concepts, or whatever it may be. But it never really dawned on me that it might be a long-term thing. Fast-forward to college, when I was a teaching assistant. I thought teaching students was a lot of fun, but it wasn’t my ultimate goal.
Then, fast-forward to Graduate School work, and I’m working at a hospital. I find myself constantly onboarding and upskilling people in different areas. One of the departments was doing a very large initiative for the enterprise, and they wanted me to lead the training team. I asked why, and they said they saw what I built and how I was able to get people from this point to that point, and that I had a great skill set for that. So, I said yes, and that was my first real job in the learning and development space.
Now I have cultivated process improvement and quality standards in seven different industries, and I think I’m on the trajectory towards a Chief Learning Officer type of role. That’s where my journey has taken me so far, and who knows what’s next.
Q: What is your favorite part of your current role at Southwest Airlines?
A: One of my favorite parts of my current role as a strategic learning partner over the corporate portfolio of learning programs is meeting with customers. At the very initial stage when they think they have something that needs a training touch, I go through and I do a lot of discovery, ask a lot of questions, and just have a conversation with them. I’m not dictating to them, they’re not dictating to me, and I’m taking notes in real time.
It’s really building that customer relationship and helping them see sometimes training or learning seems like a good path for what they’re wanting to do and sometimes it’s not but letting them get to that point of making that decision. Sometimes by the end of that initial intake journey, we know exactly what we want to do, or we’re not really sure, and we come back to it.
It’s really that customer relationship building that I love. I’ve made some great friendships through it. Even customers I don’t work with anymore, we still meet up for lunch and just chat.
Q: What are your team’s current challenges?
A: I think in the current economic environment, every organization is really struggling through how we deal with where we are right now and looking at what that also means for tomorrow or next year, whatever that is.
So, some current challenges we’re having are rethinking and realigning what we want our learning area to be. And figuring out how we take what are the best bits of it, and how do we make it into something different but not so radically different that we don’t recognize ourselves. And so, I’m very heavily involved in helping shape that transformation by writing the policies and procedures and working with the different areas within our teams.
I think that’s probably the environment every learning department is in right now. Asking, “What do we do? Where do we find our value? How do we utilize the tools that are out there, including AI? What are those use cases?” So, I’m researching all these new tools and how we use them to get our people skilled, cross-skilled, and up-skilled.
Q: Your Learning Leadership Conference session is going to focus on Agentic AI. For those who don’t know, what is Agentic AI?
A: Agentic AI is AI that has agency, meaning you can pre-program it to a point, but it can then learn and adapt and adjust by itself without you having to go in and keep tweaking it. You can tweak it, but it has the agency to make decisions or do things based on its base model.
For example, something you may have seen if you use Gmail is that Agentic AI is already built in; they have tabs for your primary, your social stuff, your promotions, and it’s automatically filtering things out. Agentic AI could go to that next level and look at your e-mails, then condense them at the top, which is something that’s been happening very recently, at least in my inbox. For example, if you have a trip coming up, it could create a summary of everything in the entire inbox about that trip. Then you’re not having to search for the information; it is taking that agency to do it itself to help us out.
Another thing with Agentic AI is predictive text on phones and emails. It offers what it thinks you might want to say. It may automatically draft an email for you depending on what you could say. That’s Agentic AI in a nutshell.
Q: Without giving too much of a spoiler, what can attendees expect from your Learning Leadership Conference session?
A: The main premise of this talk is to upskill and reskill our people. Utilizing Agentic AI as a tool to get us into tomorrow and forever, or maybe not forever, but for a while. We’ll even look at a few use cases where I’m going to use AI live to show you some possibilities that you can implement today.
Q: What perspective will you bring into your Leadership Insight Forum on building a data-driven learning strategy?
A: I’ve implemented learning strategies in four different industries. I’ve learned that we need to go back to basics as far as creating a learning strategy with data. So, for example, we can talk about training hours all day. That does not tell us anything really. It just tells us how long people have been doing things. But is that good? Is that bad? I don’t know. It’s a vague data point.
My perspective going into that is that we need to identify a singular goal or outcome. And that’s what we need to drive towards. It may not be for the entire department, which is fine, but that gives us something to get our first foothold into that data-driven strategy. And once we’re there, it’s a lot easier to snowball into expanding out that strategy to create concurrent goals across the organization. But first, we’ve got to identify that one thing that gets everybody on board, then we can start building from there.
