Episode 02Curiosity before certainty with Jessica Savage
The first answer may sound right. So why stop there?
In Episode 2 of But First, Clarity, host Malorie Benjamin talks with DS+CO CEO Jessica Savage about curiosity as a practical marketing skill. When AI, dashboards and expert advice can offer a quick answer, leaders still need to spot the assumptions behind it, seek missing perspectives and decide when the answer has earned their confidence.
The conversation explores the difference between productive questions and indecision. Ultimately, clarity comes from understanding what we don’t know, not from having every answer. Curiosity can sharpen a decision without turning every choice into endless exploration.
This Episode’s Clarity Check:
- What assumption is this answer making?
- What might we be missing because of the data, perspective or question we started with?
- What would make us change our mind?
| Speaker | Dialogue & Audio Description |
|---|---|
Malorie | Welcome to But First, Clarity. I’m your host, Malorie Benjamin, and today we’ll be joined by our CEO, Jess Savage. We’ll be talking about a skill that matters even more in an age when answers are everywhere. Curiosity. |
Jess | Thank you for having me on the podcast. This is exciting. |
Malorie | It is exciting. Thanks for being here. |
Jess | I’m slightly nervous, so I need to share. |
Malorie | Yeah, don’t be nervous. It’s gonna be great. We’re just having a conversation, so don’t stress. |
Jess | All right. |
Malorie | Curiosity is one of DS+CO’s core values. As you know, it’s one of my favorite core values. But we’re gonna go down a path today of talking about how strong marketers really resist the urge to buy into the first answer and understand when is the right time to ask more questions, get more information and how curiosity shows up in our day to day. So to set it up a little bit before we jump into the questions, AI and dashboards and experts are all around. So every time we’re seeking an answer to a question, it seems like they’re instantly available to us. So how do we understand when we should stop accepting the first answer and really dig in to understand a little more deeply on the topics at hand? So Jess, when the answer arrives almost instantly, what should make us pause and ask another question? |
Jess | I think this goes back to the fundamental roots of childhood, right? My daughter just shared this story over the weekend, that the 2-year-old son of her lacrosse coach is in that stage where he asks the question, “But why? But why, Mom? But why, Dad?” And I think if we are going to serve our clients and one another as colleagues, in our absolute best capacity, we need to, at a minimum, ask why and pause and take the time and potentially ask why again, ask why a third time so that we can get down to the real kind of root opportunities that are present in what might have started with the seed of the first answer, but built when we’ve taken a little bit of time to explore deeper. |
Malorie | Yeah, I love that. I wonder, too, what is the connection to speed and the desire to have speed, especially in a world where instant answers are available to us. How do you see that playing into someone’s desire to accept that first answer? |
Jess | I would frame it as saying like, that’s the trap. And I also think about it this way: With the tools and technologies we have available to us, if I’m asking a generally obvious question, maybe using the tools, I’m going to get a generally obvious answer back that feels like a commodity answer, then anybody could deliver that answer. But the value as an agency and organization that we’re going to provide to our clients is the layer deeper and deeper still that would allow us to share an answer that really gets to a point of differentiation, really gets to the unique value. It requires more. And I think certainly in the transformation of marketing and advertising, amidst the change with technology, that is going to be either the trap that will bring a business down or that leveling kind of reality check to say OK, got it. The first obvious answer, I understand. Now let me take this further. And that’s the human kind of intellect that curiosity drives. |
Malorie | Yeah, I think that’s so important. So beyond asking a lot of questions, right? Like, at the core of it, when someone hears someone talking about curiosity, they’re like, oh, gosh, they’re gonna ask me a million questions. |
Jess | They’re gonna pepper me. |
Malorie | Yes. Right. Or I’m on the hot seat, whatever that looks like. But beyond that, asking a lot of questions. What does it look like in a strong leader or a strong team that’s operating really well? |
Jess | That’s such a great question. I think framing it around curiosity, framed as leadership skills, is really important to understand. So I can’t remember where I learned this. I write a lot of things in my journal when they first feel that they’re profound or resonate. But as leaders, we should think about kind of a framework of what assumptions am I bringing into this situation or this matter that I need to make a decision on? And how prevalent are my presumptions? I am a singular person with kind of a level of experience, but there’s so much more that could be considered. So I think about assumptions. I think we also have to think about fear. Like, what am I avoiding if I take this fast path with the answer? What am I avoiding? What am I scared of? And is it so safe that actually it’s a detriment to deliver the safe decision? And then I think about the biases that I might be bringing. I think it’s really hard to identify our biases. So we have to find questions around it, like, what is it about my identity that I’m trying to protect in this decision? Where’s my ego showing up here? That is limiting and could be limiting in the decision. And then a fourth thing is being able to think about what could happen if something goes wrong with this decision. How prepared am I for that? And if all things go right, what’s the benefit and the space in between? And just being able to navigate that a little bit is important. So I think about that as a leader because our influence on the people around us or the influence on, like, bringing people aligned to what we’re trying to potentially move forward can be negatively impacted if you’re not kind of tearing apart and reflecting what you’re bringing into it. |
Malorie | Well, how do you kind of—I guess let’s go to the challenging question for people: Is curiosity innate or can you teach it? |
Jess | Oh, I love the question. I think going back to what I said at the beginning, from that natural childhood behavior, to ask why, when your new little self is forming and learning and absorbing, it’s innate. It’s innate to be curious. And I think as we evolve in our lives and get older, that different environmental and experiential things can kind of quash that curiosity. So I think it is in us all, but it also is a skill to be trained. I think some people may be more curious than others, but I also think that it is. It’s not a personality trait. It’s a skill and a characteristic that can be trained and fostered. And I think it’s up to managers and supervisors to help develop that and also organizations to practice it. And it’s our responsibility to know and use our judgment on when we need to bring more of it into the framework. I think it leads me to talking about the Basseterre Model that we learned about and knowing that we each may operate in different aspects of an innovation model. I think you’re going to have to correct me if I can’t remember them. But the Generator, that’s like, big idea. And then the Conceptualizer, that’s saying, oh, that’s a good idea. Now let me connect some dots to make this a little clearer. And then the Optimizer, that’s like, yep, I understand what you’re trying to do and I’m going to fill in the gaps so that it can move to implementation. These are all trained areas that we can train ourselves around and we can ask for more from one another when we’re in a particular stage. So yes, I think that’s a long answer to “it is in us all, and we can train to enhance it.” |
Malorie | It makes me just think, like, how do you know in a conversation when to keep digging for the answer and when you’ve gotten to a place that you’re ready to decide? |
Jess | That’s a really important question. And I think it comes down to understanding constraints that you’re working within. I think the timeframes that a decision needs to be reached has to be understood. You can navigate those phases of innovation that I mentioned: Ambassador, when you’re understanding time, like these are great, let’s generate some ideas as we brainstorm, but we’ve actually got a deadline we have to meet. And so your willingness to work within the time constraints is important. You can only go so far. You can over-perfect over-noodle. And certainly, in a creative industry, we know this, right? We’re working with so many sensitive and creative beings, where the work can continue to be shaped, molded, improved, you know, nuanced. And so we have to time-box it, right? So now also we have to trust our gut and our intuition. And some people are more in tune with that than others. And I use mine pretty regularly. So if I am feeling an ounce of uncertainty and I’ve reflected to say, am I prepared for whatever possible outcome could come for this? And if I can’t connect those two with a level of confidence, then I need more. And so I’m going to use intuition. So call it … the answer lies within the beautiful constraints of the decision and when it needs to be made and what your intuition and gut’s telling you based on your experience, knowledge and evaluation of that. |
Malorie | So on that note, how do you know when the confidence is earned versus premature certainty? Right? So we talked a little bit about this concept of, we saw the first answer, or maybe you’ve done a little bit of digging and you have a bit of background and you sort of think, OK, I’ve got a good handle on what this looks like. A good enough handle. How do you know when you are in that place of we’re good to go, we’ve got what we need, we have enough? We’ve used our curiosity to fulfill all these questions that are still outstanding, and now we need to move forward. |
Jess | Yeah, to rock and roll. Yeah. Have you ever read the book “Decisive” by Chip and Dan Heath? They talk about the notion of ooching. And I’m like, ooching? What is ooching? And ooching is the notion of being able to take small steps to test a hypothesis to get to ultimately enough learning to move to that full place of confidence so that you don’t get so slowed down because it’s not perfect and you’re not fully, you know, you don’t have the full confidence, but you have a willingness to take a small step or two. Ooch¬—a decision forward by testing, learning, iterating and move forward. And in this environment where we are forced to manage the pressure of haste and rapid decision making and rapid implementation, that ooching notion is a brilliant way to say, hey, we’re going to test and learn and move and pivot and keep going. So I’m going to land there. Everybody needs to learn how to ooch, take one small step, move. Just keep moving forward. |
Malorie | OK, I’m going to bring up the dirty word, AI, in this conversation within curiosity as a topic. But how can marketers use AI as a partner in these spaces to continue to expand their curiosity versus just seek that easy answer to a question they’re looking for? |
Jess | That’s great. I think AI is not a dirty word. AI is the, you know, it’s the nature with which we are operating in as individuals and in the business community, right? And it’s infiltrating every part of our lives, and making sense of it in our lives is so important. And it comes back to the question you asked earlier about how do you prevent people, colleagues, teams from taking the first answer that they may have gotten from whatever their inquiry was using the tools. Yeah. And so what I’ve found, and I actually credit you to this because you had introduced the book. Everything for me as like a DIY business person comes back to what I’m reading and what I’m making sense of it. So you shared the book “The AI-Driven Leader,” and that created in me a wonderful framework to understand how to use AI as a thought partner and to develop prompts. So it interviews me and challenges me and asks me questions. And because of the nature with which I’m using the tool, I’m not getting a first-answer pass. It’s asking me more questions that I have to stop and think about. And as a result, that’s building that curiosity muscle in me further, because I’m thinking through the policy I may be developing, the architecture around an idea for the organization. So I’m using it in that regard. It’s using the tool to question my own assumptions and framing my inquiries with, you know, ask me about the biases, ask me what I’m not thinking of when I’m putting this forward. Ask me who I have left out of the equation or who I haven’t thought of and how this might affect that audience or something. So using it to prompt the questions, generate the thinking. |
Malorie | Yeah. Right. It’s even the things you haven’t thought about. I love that. Well, I’m glad you read it and you liked it. |
Jess | And I’m also asking the AI, do not agree with me. |
Malorie | Yeah. Yes. |
Jess | And do not tell me I’m smart. I actually don’t want to hear that. I just want to get to the meat of the issue that I am leaning into it for. |
Malorie | Give us a real-life scenario where you started off in a situation, you needed to ask some follow-up questions, you got curious, and then you found a different direction as a result of not just accepting that first answer that you’re given and you really dug in. What maybe question in that changed the conversation for you, and maybe give us some outcomes so we can understand that scenario. |
Jess | OK, so I think I may take it away from AI. |
Malorie | Please do. Go for it. |
Jess | One of the things that we practice within this organization is like testing our assumptions and testing our bias. Because the work that we’re creating across our wide array of clients is meant for different audiences. And if we are not testing our own biases, then it’s going to show up in the work, right? And so we created the IDEA panel and we run the work through the panel, which is a diverse representation of individuals across this region and beyond. It’s national. And by putting our work through this panel, we are giving ourselves the space and opportunity for the biases that we didn’t see or cannot see to potentially be identified. And I can remember in particular, this was a couple years back, where we had, this was a fun project. We were working on the theme for the ADDYs. It’s the most fun. And we put through three different ideas and one of them revolved around like an outdoor park-like camping theme. And by putting it through this, I mean, if you looked at the work, you’d be oh my gosh, so fun. I could see how we could pull this off from an event standpoint. It’d be so great. And we put it through the IDEA panel and we were illuminated—what was illuminated. What I’m trying to say is that, hey, that fun camp experience that you’ve built this idea around is not really an accessible opportunity for many populations, particularly in urban centers where outdoor camp is just not available in your backyards and also access is limited and cost structures, etc. And so here we are trying to create a fun theme for a unifying experience and we are using one that people can’t relate to. |
Malorie | Right. |
Jess | And so then that evolved into, well, what is a more universal shared experience of gathering that brings people together? And we moved to an outdoor barbecue and how that can take shape in many different facets of life and cultures, right? So we worked on this thing with this fun idea and realized, well, by doing that, you’re leaving a lot of people out and people don’t get it. That connection is not there. So that’s a place where we use the IDEA panel to help us identify biases in our work to improve the work. |
Malorie | I love that. So just to kind of recap here, it sounds like we’ve got a good curiosity check. So when we’re looking for this in real life, we should be, before we accept a first answer, thinking about what assumption is the answer making, what data might be missing, what perspectives might we be missing from the conversation? What question did we start with and maybe even is it the right one? And then what would make us change our mind? Do those sound like the right questions to be asking for somebody that’s just looking to get started? |
Jess | Absolutely. The two things I would add to it are the fear and identity component. What am I scared of? Or what am I avoiding by making this decision? And where’s my ego kind of showing up in this if it’s resting in my lap alone? And then I think another thing to consider, because there is the habit in that notion of urgency to pull from past experiences where a decision was made and it worked out. |
Malorie | So what can a leader do to make thoughtful pushback feel safe? Obviously, not every culture has this ingrained in how they’re operating. For us, it’s a core value, and so we’re comfortable showing up in this space a little differently. But how do you help someone who maybe hasn’t done this before, isn’t used to extending their curiosity muscles in a business environment? |
Jess | I think that leaders need to be willing and prepared to be wrong a lot. And I think, as leaders, we need to create some pathways for people to learn that it is safe to push back. So for an organization like ours, we’re going to use pulse surveys to get feedback. So it’s just part of the norm. It’s going to happen two times a year. We’re going to get feedback and then our responsibility as leaders is to identify themes and say, hey, we’re going to work on these things. If people see cause and effect of I’ve given you feedback and something happens that creates confidence, that that’s allowed, right? I think also leaders need to show up with a level of vulnerability and say, I’m not quite convinced that this is the right path, but this is my idea. Challenge me, challenge my thinking. So invite it in. Get feedback on what people across an organization might think about it. And are we willing to evolve our thinking based on input and not get caught in a time trap of like, oh, but it’s got to be done—we said it would be issued October 1, right? So sometimes you gotta pause. I think you and our colleague Rosi say this a lot. Sometimes you gotta slow down to go fast. |
Malorie | Right. |
Jess | And so it’s up to us to, as leaders, learn over time and judgment when to pull that, turn that dial, I guess, up and down. |
Malorie | 100%. So we’re getting closer at the end of our time here. That went fast. But tell me, from a client perspective, how does curiosity benefit our clients, and not just ours? Say you’re working in any organization. How’s it good for the business? |
Jess | The first thing that comes to mind is that by demonstrating curiosity, you’re gonna build the idea in our client’s mind that you care about their business. We are an ad agency. We are not subject-matter experts in any particular industry. Some are that specialize, right? But for us as a full-service independent, we have a lot of different industries we serve. Marketing is marketing, right? Right. So our superpower is the way that we engage and probe and provoke to learn about a client’s business. And if you’re doing that and also learning and provoking and trying to understand the motivators of your client partners, then you can better understand how to serve, how to create ideas and plans and solutions to the problems they’re facing. If you are not curious and invested in their business and wanting to learn more about the dynamics—like we had a team that just attended a tradeshow. Are you kidding? You’re sending an entire team to serve as observers of an industry culture. Brilliant. Imagine what comes out of that. |
Malorie | Right? Definitely. So thank you, Jess, for being here today. Appreciate your participation. Yeah, this was great. It was an amazing conversation on curiosity, and clarity doesn’t come from having every single answer, as we know. It’s about being curious, getting into the conversation, and looking to understand what we don’t know when we start to dive into a project. Right? |
Jess | That’s right. |
Malorie | Awesome. |
Jess | Thank you for having me. |
Malorie | Thanks for being here. To get new episodes straight to your inbox, subscribe at dixonschwabl.com/email. |