How To Turn ADHD Challenges Into Leadership Strengths with Claire Milligan

What if ADHD could be your secret weapon for business success? In this episode, I sit down with Claire Milligan, CEO of Aimably, to explore her incredible journey from Stanford’s psychology and communications programs to leading innovation in tech.

Claire reveals how understanding ADHD’s neurochemical aspects has transformed her problem-solving and leadership skills into true assets. She shares how her early experiences with educational software and cloud cost management shaped her dynamic leadership style and decision-making approach.

Discover how Claire views team members as unique individuals, balancing financial goals with employee well-being, and why creating a positive work environment is key to sustainable growth. Tune in to see how embracing your unique traits can drive your business forward.

Interested in learning more from Claire? Visit her at Aimably to explore innovative solutions for your business. You can also connect with Claire directly on LinkedIn or follow her creative journey on social media at Claire Designs.

Books Mentioned: The First 90 Days: Proven Strategies for Getting Up to Speed Faster and Smarter by Michael D. Watkins.

Ready to Finish 2024 Strong?
Don’t wait until December to address your challenges. There's a few months left in 2024, now is the time to plan for a strong finish! Book a free strategy call with Dr. William Attaway to create a plan for impactful results. 

Chapters

• 0:00 Introduction to Claire Milligan
• 3:02 Reframing ADHD as a Superpower
• 5:49 Treating People as 3D Human Beings
• 9:59 Aligning Incentives for Behavior Change
• 13:03 A Decision-Making Framework for Financial Goals
• 23:32 Continuous Learning and Growth as a Leader

Transcript

Dr. William Attaway: 0:00

It is great today to have Claire Milligan on the podcast. As the CEO of Aimably, laire helps business leaders capture opportunity from their relationships with AWS, azure and Google Cloud. With extensive experience scaling B2B technology companies, she built Aimably to help other scaling leaders leverage cloud cost insights to accelerate the growth of their businesses. Leaders leverage cloud cost insights to accelerate the growth of their businesses. Claire has a BA in psychology and an MA in communications from Stanford University, where she developed her interest in politics, organizational behavior and communication research. She is obsessed with taking on complex problems, distilling them into understanding and working with talented teams to generate innovative and streamlined solutions. Claire, I'm so glad you're here. Thanks for being on the show.

Clair Milligan: 0:53

Thanks so much for having me. It's really a pleasure.

Intro / Outro: 0:57

Welcome to Catalytic Leadership, the podcast designed to help leaders intentionally grow and thrive. Here is your host author and leadership and executive coach, Dr William Attaway.

Dr. William Attaway: 1:19

I would love for you to share a little bit of your story with our listeners. Claire, I had a few of the hot points, but I would love for you to share particularly around your journey and your development as a leader. How did you get started?

Clair Milligan: 1:27

I got started because everybody coming out of school around the same time that I was was getting into this new Internet thing and I wasn't really sure how I fit.

Dr. William Attaway: 1:37

You got out pretty well right, I guess.

Clair Milligan: 1:38

So, yeah, I wasn't really sure how I fit in.

Clair Milligan: 1:43

Uh, yeah, I wasn't really sure how I fit in, so I uh got into a tech company that did, uh, educational software, and quickly realized it wasn't a good fit for me and decided I was going to go to design school, and I've always thought that design is a fascinating thing and how we interact with our world is, uh can be, purposeful and thoughtful and streamlined, and so it was a really natural fit for me.

Clair Milligan: 2:10

Uh, except for the fact that it turns out I like designing businesses a whole lot more than I like designing logos and and and websites. So, uh, I I got that degree and got back into into the software world, uh, and got really excited about designing software solutions. And, in terms of leadership, I found that it's all about psychology I kept coming back to what I had originally learned and it's about activating teams and setting incentives and making sure that we're all understanding what we're doing, and luckily, I felt like it was a good fit for me. The other interesting thing and just as a side note is that my parents were introduced by their parents, who worked together in the California Bankers Association Super nerdy, but that meant that our dining room table, like growing up, was always a conversation about organizational leadership and behavior and how to manage teams and resolve issues and help the community, and so I think that I was kind of wired for thinking that way from the very beginning.

Dr. William Attaway: 3:21

You know I love that. I say often that there's no such thing as a wasted experience, and we are all a product of all of the experiences we've had in our life thus far, and we can either try to hold those in and keep those inside of a reservoir, or we can be a conduit and share those with other people. And it feels like that's part of your story too, that you have taken what you've learned and not just used it for your own benefit, but tried to empower other people through the insights that you've gleaned along the way so far. Would that be accurate?

Clair Milligan: 3:53

I think that's really accurate. I mean, even if it comes down to a podcast I've listened to or a book I've read, if it works for me, every single person who knows me will hear me crowing about this subject because I think it's so important to share. So, yes, person who knows me will hear me crowing about this subject because I think it's so important to share.

Dr. William Attaway: 4:09

So, yes, that resonates quite a bit. You know, when we talked previously, several things about you jumped out at me One you are very focused about reframing something that a lot of people see as a weakness or a struggle point, and you were all about reframing that as a strength, and what I'm talking about is ADHD. A lot of people look at that and they see that as a weak point, particularly if you're a leader or a business owner. That's something that you got to figure out how to overcome or work around or work through. You have a whole different perspective on this. Can you share that?

Clair Milligan: 4:45

Yeah Well, first of all, that can't possibly be true because so many leaders have ADHD. It's like there's this Venn diagram between CEOs and ADHD, and it's just overlapping more than any other role. So it's got to be a superpower that we have to learn how to harness and maybe we do by falling backwards into it or we proactively do it, like I'm trying to do but it's definitely something that can be a superpower. So anybody who tells you it's not you know there's. There's obvious evidence otherwise. But I think the point, the important point, is to actually learn more about it. As you described about me early on, I like to learn something in entirety so that I can then distill it and explain it back in a way that allows people to move forward and work with it.

Clair Milligan: 5:36

And the way I understand ADHD is that it's a neurochemical difference in that your brain consumes dopamine at a very high rate, and so dopamine is what can overwhelm you, and it's also what can inspire you and motivate you to do work, and so, by overconsuming it, you may end up with a vacuum of it, and that results in kind of unwillingness to get started, as it appears, even though it's not really willing, or it can appear as just needing something to drive you, like being hyperactive and needing to fidget and that kind of thing, because there's just a lack.

Clair Milligan: 6:14

But on the other side of it, when you think about dopamine clearing behaviors being very efficient, then what might overwhelm a conventional neurotypical brain is actually like food for the soul for an ADHD person. You bring in a really complicated situation with all these different inputs and it's like all the synapses are firing and we're ready to go, which actually can lead to a situation where somebody with ADHD might really judge themselves that they cannot get out of bed to make themselves breakfast but at the same time they can spend 48 hours nonstop on a very complicated project that's interesting to them. So you just kind of have to understand that you shouldn't be hating yourself for the easy things, because your brain's just super efficient.

Dr. William Attaway: 6:59

You know I love that framing. Too many of the conversations that I have with people who have this diagnosis are around apologies Like oh, I'm sorry, I'm just you know I'm ADHD, I just you know I can't focus. And I love your framing because what you're saying is hey, hold on, stop apologizing for who you are, for how you're wired. You can take this and you can leverage it. You're just looking at the shadow side of it. There's a whole different angle here. You talk about this in terms of hyper-focus. Yes, what is hyper-focus?

Clair Milligan: 7:39

Hyper-focus is something that it's hard to describe if you haven't been in it, because anybody with ADHD, even the moment you say hyper-focus, even if they haven't heard it before they go oh, I know exactly what you're talking about.

Clair Milligan: 7:57

And it becomes this fixation, uh on on doing something to its end. And it might be, uh, somebody goes and is like I'm going to clean out my entire kitchen and that might be a thing, and they just look like a whirling dervish and everything's out and everything's it, and then it's finally done and it took a while. Or it might be a person who stays up, puts off a project in university until the very last moment and then is just up for a period of time and just focused, focused, focused on it. The hardest thing, I think, to understand when you don't have that is that for a neurotypical person, having to put that much focus and that much energy in a condensed period of time is exhausting, and it's the exact opposite for an ADHD person. Doing things slowly, without a timeline, without just a regular pattern in a routine of behavior, that's exhausting to an ADHD person. Doing things slowly, without a timeline, without just a regular pattern and a routine of behavior, that's exhausting to an ADHD person. The overwhelming last minute pressure is exhilarating.

Dr. William Attaway: 8:55

So when you're talking to leaders and business owners who struggle with this and they've seen it as such a negative and you're framing it in a different way, how do you help them get started in reframing this?

Clair Milligan: 9:07

It's funny that you asked that question that way, because I don't even know if it's a reframing. I think that a lot of folks are talking about the workplace nowadays in the sense of making it an optimal place for all folks to work, and there are ways that ADHD people self-manage that are in alignment with just pure basic good organizational leadership. And so reframing for leaders to understand those who work for them, that's fine, but I think that there's a big difference between I want you to do this work and I want you to do it this way, and here's where we're headed. Here are our goals and this is what success looks like. Do it the way that works for you, and one is better leadership than the other, and one does not require the exact working patterns of the people below them, because ultimately, we're all professionals, right? I don't have to know that you work better with colored pencils and check marks and calendars to excite you about your day. It doesn't matter to me, right? Yeah?

Dr. William Attaway: 10:24

I 100% agree with you. What you're describing is what I call treating people like actual 3D human beings.

Clair Milligan: 10:30

Yeah.

Dr. William Attaway: 10:32

You know, treating them as though they are not just a function of what they do for the team, for the organization, but you're seeing them as a person and you're treating them that way, and I think that matters from a leadership perspective, because the best leaders I know are the ones who see people that way and the worst leaders I've seen are the ones who only see people as means to an end. They see their team members as simply what they do, and once they do that, they're done with them. Yep.

Clair Milligan: 11:03

And how people are changes over time too, Like if you say X person works for me, they work this way, they do this work well.

Dr. William Attaway: 11:12

Yeah.

Clair Milligan: 11:12

They might be learning more things. They might be adding to their skill sets. They might be learning more things. They might be adding to their skill sets. They might be interested in different areas. They may have more mature perspective. They may understand your business better. Now, if you see them transactionally in one way, you begin to create a worsening work experience as you hold that view of them consistent over time. That's good.

Dr. William Attaway: 11:35

One of the things that I struggle or I see clients struggle with so much and business owners, agency owners, leaders of all stripes is making decisions. That is a huge piece of leadership because, even if you're a fantastic delegator, there are certain decisions that are going to come to your desk. There are certain decisions that only you can make. You have a framework, and you describe your decision-making framework as one that empowers and one that excels. I would love for you to share that, particularly in the space that we're talking about.

Clair Milligan: 12:11

Yeah, I think that decision-making is really as effective as it is implemented. You can make a great decision and implement it poorly, and that makes it, in hindsight, not a great. Decision is a short piece. It's about learning everything that's around you and and um trying to get a new perspective or frame of the world and seeing how to implement it, how to see the change as a result of that. But there are multiple different ways you can solve that problem.

Clair Milligan: 12:47

The key is involving everybody else, and so that is their input before, their thoughts afterwards and aligning their incentives with that decision.

Clair Milligan: 12:58

So it's a very structured like think about, uh, change management like a chess board which piece needs to move forward that moves the other ones along with it, and how do we make sure that those pieces are the right pieces as well?

Clair Milligan: 13:15

On the other side of it, when you're talking about the exact change, as much as I was brought up in the world of psychology and design, I do think that most business decisions are financial. I think that the framework for making a decision is a financial framework, and so what are your financial goals and are these various initiatives you're trying to decide between going to move your financial statements in the direction to support your financial goals, of actually building in when you're thinking about those chess pieces and implementing it, actually making sure that their financial incentives are in line as well. There's no way that somebody is going to go out of their way to change what they're doing if they are not compensated maybe not financially, maybe in time, maybe in a better work experience. There's all kinds of ways, but there has to be an incentive aligned for behavior to change.

Dr. William Attaway: 14:15

For the business owner. It can't just be an incentive aligned for behavior to change.

Intro / Outro: 14:19

For the business owner?

Dr. William Attaway: 14:20

it can't just be about the bottom line, though right. I mean for a great leader. Aren't they focused also on caring for the people that they lead?

Clair Milligan: 14:33

caring for their team? Yeah, but that's also a financial decision. You know, if you have a incredibly great place to work where you see people as 3D people, they stay and they grow with you, and that is a financial decision, because hiring more people and onboarding more people is very expensive, right? Yes, churn.

Dr. William Attaway: 14:56

Oh my.

Clair Milligan: 14:58

I mean churning customers. That's brutal. You could treat your customers well or you could be very transactional with them and be super high volume. There are ways to be effective business leaders in that methodology where you've just got a staffing agency and people are pawns. That is true. I'm not saying that you have to treat in every business case people as 3D people, however. That is a financial decision. In most cases. That is very smart and saves you money.

Dr. William Attaway: 15:24

Because a bad hire I mean. I've seen studies that say a bad hire can cost you between two and four times their annual salary.

Clair Milligan: 15:32

Oh yeah, because they have a cascading effect on everybody around them. Yeah, yeah, the longer you hold onto them too.

Dr. William Attaway: 17:08

Yeah, so decision-making framework then needs to take that into account. It's, it's, it's a it is a financial decision, but that financial decision is also about what is best for the people around you what is best for the people around you.

Clair Milligan: 17:26

Yes, and I think that it's important to frame all of those values of your business in that way. I think that sometimes businesses get to the point where they communicate a mission and a vision that's so holistic and community oriented that they almost have to apologize that they're also in the business of making money. I mean, that's what a business is, and so the more we're upfront about how these things overlap, I think that that actually builds authenticity, like we are an excellent place to work because we want to be successful, we want to drive success for everyone here. We want you to partake in that success, right?

Dr. William Attaway: 18:10

Yeah, leading in a healthy, sustainable way means that you're not ignoring the bottom line. It means that you're not ignoring the fact that you've got to be able to sustain this organization, this company, this business. Over time. You can make the best place to work, but then in six months, have to shut your doors because you did such a bad job monitoring your numbers.

Clair Milligan: 18:28

Absolutely.

Dr. William Attaway: 18:30

You thought you were trying to focus on people, but really you were just being a bad leader. Oftentimes a business, or a business owner, a leader will bring in a consultant when they feel like things are stuck, when they feel like they don't know what to do next, and oftentimes consultants will start evaluating metrics, start evaluating KPIs and start evaluating decision-making. Like how do you make decisions here? What is the best way to do that? What is your advice to somebody who feels stuck, who feels like I'm not sure. Maybe we need to bring in somebody from the outside, maybe we need a different perspective to help us look at our decision-making systems. Do you have any advice for somebody who's feeling like that listening to this conversation?

Clair Milligan: 19:14

Yes, I think that a consultant is only as good as the problem that's presented to them to solve. The more specific you can be about where you have an issue or what you feel like you do not have the capability to solve, the more value they can add. In particular, we actually, as a business, started out thinking, hey, we're going to be totally a tech business, we know tech, we've got this solved, this is a tech problem. But, as it turns out, the majority of what we do is actually consulting, because there's a huge gap in knowledge between what the software might do and how it helps you. So we can show you the numbers, and the numbers are great, but they don't mean anything until we put that into practice. Right, um, and we could spend all our time focusing on how you could save money, but if that's not your goal, then we've been sitting on the wrong track and we're not using your time properly. So, uh, and and you might even be frustrated with us you might be upset about your engagement with us. So be very specific and take the time to consider what it is that's missing for you as the leader that you want the extra help with.

Clair Milligan: 20:34

As an opposite side of that a lot of times people bring in consultants to try to have the defense of themselves, like they think what's right and nobody will go along with them. So I'm going to bring in a consultant who's going to agree with me and then they're going to convince everybody else. I don't really think that's very successful, personally, because if you had a great argument and if you were a great leader, you would have convinced everybody. So maybe the question is what is the actual, the better decision to go along or the better?

Dr. William Attaway: 21:03

skills that you need to develop to bring people along with you. So when you come alongside of a company, an organization that brings you in, what is the very first thing that you are looking at as you're evaluating the landscape?

Clair Milligan: 21:14

Where does the company want to be in the next three to five years is our guiding star, which is funny because we're dealing with very technical things. We're talking about what servers are being used and how they're networked and all of this, and I know it sounds silly, but if you, in three to five years, want to be making so much more revenue and you really don't care if you're not profitable at all, then we're going to be orienting ourselves towards how do we help you grow quickly and add to your feature set quickly, because that will allow you to sell more, and we will not focus on how much it's going to cost you. However, the exact opposite can happen. So let's say so. That would be like a venture capital scenario, but a scenario where you're owned by private equity. You were already successful. The private equity firm is brought in to create more value in your business and to make a gain over five to 10 years.

Clair Milligan: 22:14

In that case, we have to question everything in terms of profitability, each line of business, each business that was acquired and brought in. Is the balance between revenue and cost appropriate? So it's not even just how much you're spending. But then how does that relate, and can we tag and associate all the costs with all the revenues so we know how they line up. That becomes like a financial organization process Farther along in the storyline, when we're talking about a company that's reached maturity and they just need to return more to their shareholders, that becomes just a cost conversation and we can't make the assumption just coming in based on where we think you are.

Clair Milligan: 22:55

That would be silly and in fact we get asked to do one thing, but what's actually needed is another and it's where is the direction at the C-suite for where we're going to be next? And then we can actually work with the tech teams that are direct clients and say here's what that means for you, because that's that educational gap, and here's how we can help you get there so that you are at direct alignment with the C-suite.

Dr. William Attaway: 23:19

I think the clarity that you bring is one of the kindest things you could do. I believe clarity at its root is kindness, and what you're doing is you're helping these business owners to gain clarity around where they are and where they want to go. I think that's one of the kindest things you can do coming into an organization.

Clair Milligan: 23:39

Yeah.

Dr. William Attaway: 23:40

That's so helpful. Claire, you are leading at a different level today than you did five years ago. Your team, your business, and five years from now, your team's going to need you to lead at a different level still. Team's going to need you to lead at a different level still. What are you doing to stay on top of your game these days? How are you leveling up with the new leadership skills that your business is going to need you to have in the days to come?

Clair Milligan: 24:09

I love that question because I think, I think about it, maybe even too much I think a lot about. So my co-founder and I meet literally every day and I know that that might be overkill, but we're always second guessing and questioning whether or not the decisions and the drive and the focus and the strategies are appropriate for where we are right now or where we envision ourselves to be. And five years ago I had developed a really great skill set toolkit for growing businesses, taking something that's doing well and really pushing its growth, and I thought, great, let's take that skill set and let's apply it to a startup. Turns out you can't. So we kind of stubbed our toes a little bit and questioned everything and got ourselves into the right position.

Clair Milligan: 24:57

It took a little bit longer and I think now we're focusing every day almost on making sure we're at the right stage. So it's hard to say like, oh well, you know, I'm participating in this kind of organization or oh well, this is my one tool. I think that the real clear help for me is to make the assumption that tomorrow's problems are not today's problems and so we need to solve today's problems and assume that they will change next week and next month. If we assume that we have all the skills that we need and we're in a good place and we know how to lead, then we cannot be appropriate as the scenarios change.

Dr. William Attaway: 25:42

That's good. What is the one thing that you want most in your business?

Clair Milligan: 25:50

Oh, that's so interesting. I hope that people learn. I hope that people feel excited to learn, because we straddle this very large divide between financial planning and technical implementation. That has been the source of frustration, lost jobs, interpersonal hatred and in technology companies and companies at large for a very, very long time, and it has driven turf wars. And it's been out of a pure misunderstanding, and so, while I have this focus on building a company and having it be very successful and returning value to our shareholders, the way we'll do that is through bridging that gap, and it's just. It shouldn't be as broad as it is, it shouldn't be as vast as it is, and I hope that we can continue to add to the conversation and help people understand where each other are coming from and start speaking the same language.

Dr. William Attaway: 26:53

That's great. You know, people may be listening to you, watching you from the outside, looking at the highlight reel that is your online presence, right and they may be thinking wow, you know, claire man, her journey has just been up and to the right Like she's never dealt with the challenges that I deal with every day. She's never had to struggle like I'm struggling. If they were to tell you that, what would your response be?

Clair Milligan: 27:17

I think the knee-jerk response is to say you're wrong. But now that I think a couple of seconds, the reason why they're right is because I chose early in my career to work with very small companies and to take advantage of opportunity as the companies grew, to grow myself. I didn't do well. In scenarios where I was a cog in the machine, I performed pretty poorly. It wasn't a good alignment actually with my ADHD, to be frank with you. And the more the problem sets grew, the more the challenges expanded, the better I did, and so I haven't been stuck for a while in a specific scenario because I didn't do well in those, and so I specifically chose other things.

Clair Milligan: 28:04

Some folks in my generation said I need Google on my resume, I need Facebook on my resume, and I always said I would be terrible at those companies, so I will avoid them. So I think that that's at the same time. Would I ever get hired as a leader at one of those companies? So I will avoid them. So I think that that's at the same time. Would I ever get hired as a leader at one of those companies? No, I don't have any experience for that, nor should I. So I think that there's ways where you fit in and the way you think and the way you work is a great fit For small and growing companies whose landscapes were continually shifting. That was a great fit for me.

Dr. William Attaway: 28:43

That's good. Is there a book that has made a big difference in your journey so far that you would recommend to every leader listening? If you haven't read this, this could be a game changer.

Clair Milligan: 28:56

Yeah, it's the First 90 Days. The First 90 days is one that I always come back to every time things meaningfully shift, and it's a reminder and it's actually a framework for going through and saying what is the actual problem ahead of me? Is this a turnaround, is this a growth story? And from that, what should I do next? How can I communicate and how can I set everybody on track for success through these 90 days as we're shifting? And it's a fantastic reference and I think that, while we all have a sense that when things shift, we need time and space to figure it out, sometimes we don't take enough, sometimes we take too much, and this book is really good at giving you a clear timeline, clear formula.

Dr. William Attaway: 29:44

Brilliant. Often, people are going to walk away from a conversation like this with one big idea. Claire, if you could define what you want that one takeaway to be, what would you want it to be?

Clair Milligan: 29:57

Question everything, nothing is assumed, but be confident in what you know and how, what the data in front of you tells you and mixes with what you know to create your strategy and future.

Dr. William Attaway: 30:12

Such a fascinating conversation. I'm so grateful to you for your time and for your generosity in sharing so much of what you've learned so far with us. I know people are going to want to stay connected to you and continue to learn from you, Claire. What is the best way for them to do that?

Clair Milligan: 30:29

You can find me on LinkedIn. I am Claire C-L-A-I-R-E Milligan, and our company is Aimably A-I-M-A-B-L-Y. I'm also on a few different social sites as Claire Designs. I like to write a lot on medium so you can follow me there.

Dr. William Attaway: 30:44

Excellent, We'll have those links in the show notes. Cool, Claire. Thank you again for being here and for sharing so generously.

Clair Milligan: 30:52

Thank you so much.

Dr. William Attaway: 30:55

And for you for sharing with me. Thanks for joining me for this episode today. As we wrap up, I'd love for you to do two things. First, subscribe to this podcast so you don't miss an episode, and if you find value here, I'd love it if you would rate it and review it. That really does make a difference in helping other people to discover this podcast. Second, if you don't have a copy of my newest book this podcast. Second, if you don't have a copy of my newest book, Catalytic Leadership, I'd love to put a copy in your hands. If you go to catalyticleadershipbookcom, you can get a copy for free. Just pay the shipping so I can get it to you and we'll get one right out.

Dr. William Attaway: 31:32

My goal is to put this into the hands of as many leaders as possible. This book captures principles that I've learned in 20 plus years of coaching leaders in the entrepreneurial space, in business, government, nonprofits, education and the local church. You can also connect with me on LinkedIn to keep up with what I'm currently learning and thinking about. And if you're ready to take a next step with a coach to help you intentionally grow and thrive as a leader, I'd be honored to help you. Just go to catalyticleadershipnet to book a call with me. Stay tuned for our next episode next week. Until then, as always, leaders choose to be catalytic.

Intro / Outro: 32:15

Thanks for listening to Catalytic Leadership with Dr William Attaway. Be sure to subscribe wherever you listen to podcasts so you don't miss the next episode. Want more? Go to catalyticleadershipnet.