Jason (00:39)
Hi Daina how are you today?

Daina Middleton (00:40)
I'm great, Jason. Thanks for having me here with you today.

Jason (00:44)
Oh, it's my pleasure. Thanks for making the time. I can't wait to dive into our Wise in Five questions with you. But before I do that, I'd love for you to share some of your amazing background. I mean, you've had just this incredible journey as a marketing advertising leader, board member. So, please, share this journey with us.

Daina Middleton (01:05)
Sure,

happy to. Yeah, it's kind of crazy to look back. I was fortunate enough early in my career to spend 16 years at Hewlett Packard during kind of its heyday where it was very well known as a good to great company. So that's my client side experience from an advertising standpoint from there.

I leaped and went to the agency side and worked at Moxie, which was part of Publicis and then as CEO of Performics which is also part of the Publicis network. From there, I leaped to the publisher side and went to run B2B marketing for Twitter. And during again, crazy time at Twitter, when has Twitter not been in crazy dumb, but great experience from a global standpoint on the publisher side of the business.

Then I went back into the agency side, but this time with a private equity backer. So got some interesting experience, both working directly for a private equity firm as a leadership coach for a while, and then as the CEO of a company in a private equity portfolio. And then finally, to kind of round up my operational career, during the middle of COVID, I actually led two companies coming together and sold to our largest customer.

in the experiential marketing space. So since then, I've been mainly doing some leadership, leadership development work in the allyship space, which I'm sure we'll talk a little bit about today. So

How can we create environments where workers feel like they can bring their whole selves to work so that we can all perform at our best? And then board work. So yes, I have sat on two publicly traded companies, a couple of private equity backed companies and one venture backed firm. And so that's

I do mostly full time these days.

Jason (02:50)
really amazing. And we're going to dive into each of those. But before we do, I wanted to ask, it's a question I ask all my guests, but where do you find inspiration just in daily life?

Daina Middleton (03:00)
my biggest inspiration driver is an insatiable curiosity. And that knows no limits, whether it be, you know, I probably have some hot spot areas, obviously nature and Mother Earth and animals and people. But it could be leadership styles, which we'll talk about today. I'm on the public company of an insurance company. I didn't know anything about insurance, but one of the key drivers

of why I was so excited to join an insurance company board was to learn about insurance. But it's that insatiable curiosity that really drives me of trying to figure something out or learn something new. That really is the core of honestly everything that I do.

Jason (03:41)
So

let's dive As we talked about, you've led advertising and marketing at some of these huge global corporations, HP, Twitter, Performics recently, and Ansira And you were there in the early days of digital transformation, right? I think we both were. And my question is, how do you feel about this current shift, What we're going through with AI,

Daina Middleton (03:57)
Yeah. Yeah.

Yeah.

Jason (04:03)
Do you feel like this is similar or different to what we experienced, what 20 plus years ago now as the internet started to become more and more part of ⁓ everyday life?

Daina Middleton (04:14)
it's interesting. think it was great for you to send the questions this morning because it gave me a minute to reflect. I think we've all of our generation had the transformation of a lifetime if we think about how even work has transformed. gave me a moment to reflect and I thought about the big eight transformations that I've experienced. the first one was desktop operating systems. I remember booting up in DOS when there were no

apps or operating system, And then there were networks. We were all connected on a network. that was not a thing ⁓ originally, but going kind of riding that wave, I helped HP introduce its first server that had a gig of hard space, a gig. And it was like, ⁓ my gosh, we have a gig, which is kind of crazy if you think about now. And then web browsing. back to your internet, ⁓ what

Jason (04:54)
I'll see you in game.

Daina Middleton (05:05)
that web browsing really enabled our ability to consume the internet. Before that, it was not possible. And then mobile. So mobile phones and mobile apps. I didn't start working with a mobile phone. That was something I got later in my career. And then social networking, the rise of social networking, cloud computing, IoT, and now here we are at the footsteps of AI.

What I think is similar is we still have somewhat of a hope about what AI might bring to us. But what I think is radically different is there's a huge amount of fear and skepticism and lack of trust. That's very different from the nineties. Perhaps we were naive, probably in retrospect we were back then of what the good and the bad that

the internet and IOT and the rise of a select handful of companies. think those two things are rooted similarly that we have a concentration of companies that are primarily driving the surge of AI that came from that first wave, They were funded by that first wave.

And if we look at who they've become as humans and how they're contributing or not to humanity, I think that's the biggest difference is the skepticism. Interestingly, when I got done with my reflections and wrote down the notes, I actually posed this question to AI to see kind of what the response to be. And that I'll read you the paragraph. The response was, today's sentiment toward tech and AI is marked by a

a mix of profound excitement, deep-seated skepticism, and increasing fear, reflecting broader societal maturity and concerns about powerful centralized technology. In contrast, the 1990s internet boom was characterized by a more naive, egalitarian optimism rooted in the novelty of global connectivity." And I actually thought that was pretty insightful for AI. There you go, And in that, you see the good and the bad.

Jason (07:00)
Wow.

Daina Middleton (07:08)
⁓ I don't think for me, AI wasn't new because in many of the technologies we were using, we've been using AI for a long time. We didn't call it AI. And if we had, it wouldn't have marketed it very well. Right. I think we all struggled to market the AI components that we were using for a long time, obviously, computing power and other.

centralization and access, all those things are benefiting AI today that didn't necessarily early on. But, my hope is this degree of skepticism and awareness that we all have enables us to make better decisions related to AI. The final thought that I thought was interesting is as I reflected in thinking about what's different versus then

Largely, if I look back into those early days where we were, riding high on tech and the internet and being in tech, you know, I was at Hewlett-Backard. The large part of our day from a work standpoint was still rooted in the physical world. We went to physical meetings. We used physical objects. We went outside at lunch, even with our most senior executives and played sand volleyball.

it was very rooted in the real world. That today, I think is very different. If you think of a workforce today is rooted very much in technology and not that it's good or bad, it's just different. And my hope is as we roll forward that we'll find a balance of the physical and the digital worlds. And I look at this next generation, I think they're thinking about some of these things, but

Jason (08:45)
Yeah, I

agree. I totally agree. and, when you do that look back and it's so great that you had asked AI how it felt about this. But if I think about the early 2000's when, the recession that was happening as well as the rise of the internet. And there were always these questions of the internet was going to be this big thing. And especially in the advertising marketing world, it was going to be this is where TV.

eyeballs are going to start to go, which eventually it did. But when the recession happened, then people went, see, it's not that big of a deal. They're not going to put these retailers out of business. And it took 10, 15 years, For that to happen. And I think to the point that you're making, it could actually move much faster right now. And I think part of it is because we all have more devices. We're more connected in that way where we weren't connected as, as tightly before.

Daina Middleton (09:19)
Yeah. Took a while. Yeah. Yeah.

much, much faster.

Jason (09:36)
And I also feel like what happened during the pandemic actually accelerated things. So I think part of what you were sharing is people are not going into the office as much, People are not socializing as much. They're kind of retreating a little bit. And now tools like this make it even easier to do that.

Daina Middleton (09:53)
And what's crazy, if you look back to HP early in, this would have been the early, late 90s, early 2000s, I managed a global team. HP eliminated the desks on site. We weren't working on site. And we didn't have Zoom. We didn't have tools like this where we could see one another. We did have phones and we did get together physically a couple times a year.

But we still very effectively managed a global team and had global relationships. those tenets of successfully working in those environments became kind of my core foundation of how I worked with global teams long before COVID, long before we had Zoom, using some of those primary things. But again, it was balancing.

the physical and the digital and balancing how we worked with one another. So ⁓

So yeah, I agree. It's like we're on this and it feels like since COVID time is in a warp and things are like in this digital warped place and we still have it 100 % I think recovered from that.

Jason (10:58)
I think that's very true. And we'll see where this goes because I think also similar to the early days of the internet, governance started to come in, There was federal regulations and different ways that companies were operating. We haven't seen that yet really in AI. think we're just starting to see.

Daina Middleton (11:08)
Yeah.

No, and I don't think

we will for a while. I think the wheels are going to come off and we may pay for that a bit and then, you know, it'll snap back. mean, we've seen this many times, This pendulum that swings.

Jason (11:25)
That's right. I think what I agree there may not be as much regulation, but I think companies, especially legal departments are going to start to regulate exactly what AI can be used for and try and centralize that, try and control it a little bit more. So we'll see. I mean, it's anyone at this point.

Daina Middleton (11:38)
Yeah.

And customers

Hopefully customers also will make a statement about what you want and what they want and what they can tolerate and what they won't. We'll see.

Jason (11:48)
That's right.

Excellent point. So I'm going to keep on this AI focus, but I'm going to take it more toward how businesses are operating and where opportunities may be. And a lot of the folks that listen to these podcasts and engage with The Wisory are mid-sized businesses. And I believe AI has the ability to give these mid-sized businesses an outsized advantage against larger competitors.

Daina Middleton (11:52)
you

Jason (12:15)
If you believe that, what do you think mid-sized businesses can do, especially on the growth side? A lot of what's about is how you take cost out of the equation with AI, but I'm curious, on the growth side, what do you think mid-sized businesses can do to take advantage of this opportunity?

Daina Middleton (12:31)
I think the most interesting thing, whether you're a big company or a small company, thinking about strategically how AI can help you is a great place to start. One of the things I think we've lost broader than AI over the last few years is just strategy. What are we trying to achieve and why are we trying to achieve it? And whether it be competitive differentiation over to back that,

Jason (12:47)
Mm-hmm.

Daina Middleton (12:55)
more than just a cost efficiency side of AI implementation. Thinking about how I can add AI into the mix to make me look different, to make me feel different, to make me achieve something faster or more competitively than I have in the past. How I can process data, whatever it is that actually gives you that edge.

That's where I think ⁓ medium-sized businesses can think about it. And not that you wouldn't do both a cost efficiency standpoint and have it to be a competitive differentiator because that's the beautiful part about AI is you could actually implement both as a young business. The nice thing about AI is that the barrier to entry is low. It's relatively easy to implement. It's accessible for all.

And that's where I think back to your point, there's a huge opportunity to really access these tools and leverage them in ways that are unique and different.

very simply, very easy, very cost effectively. And that I think is the great opportunity. And it may give you I think that group of businesses in particular have abilities to really rethink and reframe traditional models in ways that nobody has thought about. Because it's really

hard when you're, been in business for a long time, you're entrenched in the way you work, to think about something differently, because you can't get away from those old models. AI gives you an opportunity to completely recraft those models and rethink and reframe an industry. And that I think we will see a lot of.

Jason (14:32)
I totally agree. think very well said the these big businesses are going to be challenged because they have all this investment, Not in people and structure and process and physical issues that they need to deal with that. It's going to take them some time to figure out

I think it'll be a very interesting time to see how things evolve with these mid-sized businesses. So I want to go to the author side of Daina Middleton, which you wrote a book, a great book, How to Bring Out the Remarkable Courageous Leader Within.

Daina Middleton (15:02)
Grace meets grit. Yeah, that's the, yep.

Jason (15:03)
Race meets grit, exactly.

I mean, it's really a call for women leaders, right? In terms of what you need to do now to take control of your career and your journey. And so I'd love for you to share a little bit more about your journey that you've experienced as you rose through your career as a female leader. And then kind of a part B to it is,

Who did you go to for mentorship when you were dealing with certain things as you continue to rise within these organizations?

Daina Middleton (15:32)
Sure. So, Grace Meats Grit really did come out of my personal experience. I would tell you that I felt like I was somewhat on a rocket ship as an individual contributor, really jumped from role to role, accelerated in those roles. And then the very first leadership role that I took where I was managing people and I was, I think all of my peers were male and I was reporting into a man, again, not necessarily

different than in the past, I was recognized as a leader, I suddenly felt as if I wasn't excelling anymore. And it wasn't that I had changed the way I did things. It was as if there was a unwritten set of rules that I didn't really understand and signals that I was missing. And I had a really exceptional boss at the time who wanted me to be successful.

And he was trying to help me navigate these issues. And there was a recognition that he could see these things and I couldn't, and we couldn't really figure out why I was missing the signals. It was like there was a code or something that was happening and it wasn't, it wasn't subversive. It wasn't intentional. It was just different. And so that was the impetus for writing the book was that I had experienced this.

And I wanted people to go into the conversation intentionally thinking about leadership behaviors related to gender, ⁓ largely because we mostly have male leaders. We still do today. Statistically, men are still in charge. We've men and women, all people have become accustomed to this largely male type of leadership behaviors.

Jason (16:59)
Mm-hmm.

Daina Middleton (17:16)
And then women are expected to snap to those behaviors and behave in the same way. And yet if we do behave in the same way, we're penalized for it as well. So it's a really difficult path to walk. So I intentionally oversimplified to a certain extent, grace is the more female approach, grit is the more male approach, in order to give us an intentional framework to talk about it.

because of course we're not that simple, I'm not just a female leader or a male leader. It's not that at all. It's just that we all have very specific leadership styles and approaches and assumptions are made about those behaviors that may or may not be real. And so I was trying to give everyone a framework, men and women, in order to discuss this in a more conscious fashion so that we could drive success. So I'll give you an example.

So by far the most biased leadership behavior is decision making. And the appropriate way to make decisions is autonomously and quickly. So, and men largely do this, and that, all of the research shows that especially under stress, men tend to make quick, autonomous decisions. They don't like to involve others in the decision making process. And it is assumed that the right way to make a decision is fast.

Jason (18:15)
Mm-hmm.

Daina Middleton (18:36)
Well, that may or may not be true if you think about the broader context of business and situations where decisions need to be made and good decisions. So of course, if the building is on fire by all means, make an autonomous decision and get everyone out, That is a good example of where autonomous decision making is very important. But if it's a very important decision that involves a lot of different leaders from different parts of the organization,

you may need to get consensus. Consensus isn't necessarily an agreement, but it's an alignment within the organization that takes you there. And it burns a lot of calories and takes a lot of time. It's not going to get people out of the building quickly, but in certain situations might be best for the leader to actually drive a decision. so, Meets Grit was built on that.

Jason (19:27)
the second part of my question was, as you've gone through your journey, are there people that you've gone to, you know, for guidance, for mentorship, when you've been challenged in different situations?

Daina Middleton (19:32)
yes, mentors.

Sure. So I would say obviously my first mentor was my mom who was a school teacher and then she went on to be an administrator. Unusual to go from being a teacher to a principal, but she was she kind of broke the mold and became that and she always told me, know, don't let anything stop you. You can be whatever you want. You know, there are no limits. And she also I think gave me that insatiable curiosity.

So for sure, early in my career, even before I had a career, early in life, she was my inspiration.

And I think the best advice that I can provide people is find that board of directors for you can be very informal or formal and formalize it to be available, to have a sounding board. Because as I rose through leader, through my leadership and actually became a CEO, it's a very lonely place to be. It's hard to, you can't really tell other people who

you're working for you, how you're feeling or share your emotions or share your frustrations. Not really, you know, that's not appropriate, but you can create a sounding board of individuals who can be that for you. And honestly, that is part of the role that I play in many cases today with the companies where I advise or leaders that I'm working with. You know, I am that sounding board, that person to ask questions.

to share my own experiences, what I did well and what I didn't do well and give them things to think about. That is still a large part of the work that I do today.

Jason (21:14)
Yeah, well, that's why I'm so thrilled to have you as an advisor on The Wisory. That's why The Wisory exists really to help people where they don't have a person they can go to. And we have people like you who have had this amazing career and are very open to sharing, right? And providing guidance. So thank you.

Daina Middleton (21:20)
Yeah, it's great.

Totally. And facilitating

even alignment. I think that's, ⁓ you know, the other thing I spend a lot of time on that I don't think leaders think about, and I certainly look back on my career and back to it, like the intentionality. I could have been a much more intentional leader, being very clear about, you know, this is the decision we're going to make. Here's who's going to make it. Here's the timeframe that it's going to be made in.

Jason (21:36)
Thanks.

Daina Middleton (21:57)
or going through an alignment exercise. How do we get a team aligned around an idea, a vision, a mission, so that everyone understands where we're going and how the interdependencies within that team work. And I would say that's still a challenge today that's really difficult.

Jason (22:17)
Absolutely.

So we're on our last question. I'm actually going to take a couple wisdom just ⁓

Daina Middleton (22:24)
I'll do the same, I have water.

Jason (22:25)
There we go. I have to get you one of our, our Wisory mugs.

Daina Middleton (22:29)
Yes, I love your little owl.

Jason (22:30)
Well, thank you.

So the wisdom. last question, and you've been in a situation where you've had boards, right? At companies that you've led. And also now, as you mentioned, you sit on boards, right? And so you've been on both sides of the table. And I guess my question is, what have you learned, right? From going from

Daina Middleton (22:33)
That's great.

Jason (22:51)
you know, being someone who was, I guess, reporting to boards versus someone who's on the other side where you're seeing these executives as they come to the board. What have you learned? What could you share with people who are going through that situation?

Daina Middleton (23:02)
Yeah, it's really interesting having been on both sides. And then the third angle that kind of gave me a glimpse was when I was coaching full leadership teams as well. So all of those angles, I think, bring value and complexity, obviously. The standard truths are, I think, that executives

are constantly trying to figure out how they can translate their business in a way that the board can understand and at the same time try to figure out how to get the most out of those boards, you know, the contribution of those individuals and collectively they can contribute

And it's continually evolving because the business situation continually evolves. The executive continually evolves. The membership and composition of the board evolves. And so the best situation that I've seen are that those places where board and executives have a very direct and authentic relationship where, you know, the pretext and

you know, the executive isn't thinking about all of this, how could, do I translate this in a way that the board can understand? And how can I say it in a way that, you know, that gets translated because all of that wasted energy is instead channeled back into what, what are we trying to achieve and how can we best go and make this happen collectively? And having experienced that, I can remember

spending hours trying to think about how do I say this in a way that my board members can truly understand it? And what if I didn't have to do that? Instead, I was just bringing the core tenets of the business and being able to have an authentic conversation and not having to worry about the translation. I think that's the best of all circumstances.

And so the best boards are the ones that I think are very diverse in every way possible, meaning they're bringing different perspectives to the table in a variety of different ways. There's a mutual amount of respect amongst board members and actually with the executive.

And there's an aligned goal of wanting to have the best outcome to achieve and how do we collectively get there? And so, you know, I think one of the things that I bring to all boards

Jason (25:13)
interesting.

Daina Middleton (25:18)
is probably the strategic alignment perspective, because my brain just works that way. So trying to ask the right questions or introduce a process or volunteer to jump up to the whiteboard to try to get us there often. yeah, I think in my ideal world, in my ideal space, we would just have boards.

magically collectively get together, they would all have this unified vision and you would, merrily go down a path to achieve that.

Jason (25:53)
absolutely. think there was so much that you shared that is just such great wisdom.

We have done our five questions and you've done an amazing job. No surprise, you've passed. But I do have one bonus question. So, and I think we've covered it, but just to put a finer point on it. So as business leaders, you know, want to reach out to you, Daina, what questions or advice do you feel like your best position to help them with?

Daina Middleton (26:00)
We have.

Yeah, there's probably two, well, maybe three vectors, I would say that where I think are my secret sauce. The first one we, just talked a little bit about that and that's strategy frameworks and strategy alignment. So I think business strategy, business framework and alignment or new market strategy, somewhat interrelated, you know, getting that down in a simple framework that can be cascaded to the organization.

You know, I have a lot of simple frameworks for that and can help guide a process and help someone figure out how to accomplish that. The second one is marketing strategy. Obviously, that's also a key part that I bring to the table. How do you simply clarify your reason why? And, you know, oftentimes companies focus on their differentiation. You know, how are we different or

what we do, this is what we are. But neither of those things actually solve the true problem that, what problem are you solving for your customer or your client, whether it's B2B or B2C is often missed. And so again, I have frameworks that can help align that and drive simplicity and alignment around. And then lastly, it is leadership. So oftentimes helping leaders

figure out how to solve a problem or navigate through a process. And I often like regular check-ins if possible for that because things evolve. And I can give you an example where I've coached a woman technology leader, actually an AI now, over the past year of really driving synergy and alignment within the organization and not only what she was doing, but how she was doing it. And so,

being that sounding board for someone is in a safe place that where honesty can be spoken and I can talk about what I've done well and what I haven't done well.

Jason (28:08)
Well, those three areas that you called out are of such importance to so many leaders. So thank you for sharing that. Thank you for making time today. ⁓ And thank you for being an amazing advisor. I'm really thrilled to have you on board. Well, it's my pleasure. And hopefully more and more people can get a chance to talk with you directly, Yep. Thank you. Bye.

Daina Middleton (28:19)
Thank you for having me.

Thank you for doing this platform.

I'd love that. Thanks so much, Jason.

Bye.