Maura Charles of Keep it Human: “Invest Wisely”

Invest Wisely — Put your money where your mouth is: if you decide to invest in digital transformation (which you absolutely should), make sure you are setting your people and teams up for success. As I said earlier, the companies preparing to disrupt your business and your industry are not holding back. As part of our series about […]

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Invest Wisely — Put your money where your mouth is: if you decide to invest in digital transformation (which you absolutely should), make sure you are setting your people and teams up for success. As I said earlier, the companies preparing to disrupt your business and your industry are not holding back.


As part of our series about “How To Use Digital Transformation To Take Your Company To The Next Level”, I had the pleasure of interviewing Maura Charles.

Maura Charles is the founder of Keep it Human, a digital innovation and product consultancy. She has 25 years of experience working in digital transformation and digital product roles for beloved consumer brands that inform & entertain. At Keep it Human, Maura uses advises a range of companies from early stage startups to global corporations on their digital business and operations in three key areas: cross-functional team facilitation for innovation, establishing a new full-stack digital product function, and supporting teams through growth and change.


Thank you so much for joining us in this interview series. Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

I graduated from college right when the commercial Internet was becoming a “thing.” My first tech job was as an undergraduate student at Johns Hopkins University in the 1990s, working on a CD-ROM project designed to teach drama. Before graduating, I interned at the Discovery Channel, where I helped build their very first consumer Website, and I was hooked! I started out focused on content and editorial, but I educated myself about coding, digital design, UX, and other aspects of building great digital consumer experiences.

I have always followed interesting work and over the years I found myself re-inventing amazing brands across a range of industries. Some of the most fun for me were Encyclopaedia Britannica, the New York Philharmonic, Bloomingdale’s, and Real Simple. I have spent most of my career helping what I would call “legacy” non-tech companies become the best digital versions of themselves.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lessons or ‘take aways’ you learned from that?

At the launch party for Discovery Channel Online in 1995, the head of the division gave me a cheeky award for “Just not knowing when to say no.” Saying no was something that took me a long time to learn, but I now understand that boundaries make you a better performer and are critical for mental health.

I still don’t say no every time I should, but at least now I know it’s a bad idea!

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

Other women have been my biggest supporters. I’ve had a few particularly wonderful female managers who supported my growth and advocated for my advancement. And two years ago, I joined Chief, a private network for executive women, and that experience has been career changing. My peers at Chief have helped me step into this new phase of my professional life as an entrepreneur. And I rely on a strong network of friends and family that are always cheering me on. I am grateful for all of them.

Is there a particular book, podcast, or film that made a significant impact on you? Can you share a story or explain why it resonated with you so much?

I love movies and I’m always finding life and business lessons in them. And I read a lot, both fiction and nonfiction, so there are many books that have had an impact on me at various stages of my life. Books help me see other perspectives and shift my mindset.

Early in my career, Emotional Intelligence by Daniel Goleman made a huge impression and helped me see that hard skills and knowledge were only part of what made people successful. I use my emotional intelligence and EQ in my professional work and encourage my mentees and clients to put an emphasis on those skills. In technology work, I often see teams that hire for technical skills and experience at the expense of human skills, and it can really show in the toxic workplace cultures that result.

Extensive research suggests that “purpose driven businesses” are more successful in many areas. When your company started, what was its vision, what was its purpose?

My consulting practice is called Keep it Human. Its vision is simple: when companies focus on the humans who are building and interacting with your digital products, everyone wins. At the core, its purpose is helping digital teams with continuous improvement. Digital transformation and innovation can be tough work to get humming, and particularly for companies with a legacy of operating in an “old-school” way. I help companies with strategies and tactics to deliver better products and outcomes. All with well-adjusted, happier teams.

Are you working on any new, exciting projects now? How do you think that might help people?

I am helping a few early-stage startups with their digital strategy and advising on how they should prioritize their limited budgets. Prioritization is an important skill, but if you do not have experience in doing it for digital, it’s not always intuitive. Do I spend money on creating great content that will drive organic traffic or paid ads on social? Who should I hire first, a product manager or a growth marketer? A lot of startups invest in digital platforms and software but not the experienced talent to guide their use — a platform is not a strategy.

The key is to find advisors who have accomplished what you’re trying to do and take their advice. Assembling a savvy team of formal and informal advisors is probably the most important thing you can do as a business starting out.

Thank you for all that. Let’s now turn to the main focus of our discussion about Digital Transformation. For the benefit of our readers, can you help explain what exactly Digital Transformation means? On a practical level what does it look like to engage in a Digital Transformation?

Digital transformation is about change and flexibility. Companies need to evolve the way they think about their business, and they need to help their employees and partners change how they think and operate. To do this successfully, a company must view its entire business through new lenses — some of which are also in flux.

The foundation of a good transformation is understanding innovative ways of working. Then a company must make sure teams have access to and use appropriate technologies, tools, and best practices to drive results.

From a practical level, this means:

  1. organizing your people around digital transformation goals
  2. bringing in talent who can help the business change, and
  3. setting goals (OKRS, for example) that will set the company up for success.

Which companies can most benefit from a Digital Transformation?

Almost any company can benefit from a digital transformation. There are even tech companies that have been around long enough to need to transform several times over. It makes sense, right? The dot com boom started in the mid-1990s, so companies that started and survived have been around more than 20 years.

Think about Salesforce, as an example. Salesforce was an innovative platform in 1999, but now its products are staunchly in the legacy space. After years of features layered upon features, technical debt, and mergers & acquisitions, the products are cumbersome and a bit of a joke among people who must use them. Companies like that need to rethink whether they’re still solving customers’ problems in an innovative way.

Continuous innovation is also part of digital transformation. I often hear people say something like, “Well my company’s products are high tech, so we don’t need to think about digital transformation.” But there is always some part of your business that can keep innovating for digital. The Coronavirus pandemic exposed massive gaps in the digital divide. Whole industries realized they were not actually digital in the way they needed to be to survive.

Industries that had to completely rethink their businesses through a digital lens during the pandemic? Healthcare, education, supply chain, workplaces, food, and live entertainment were far behind and the road has been very challenging for organizations and government agencies in those spaces.

We’d love to hear about your experiences helping others with Digital Transformation. In your experience, how has Digital Transformation helped improve operations, processes and customer experiences? We’d love to hear some stories if possible.

I love talking about the two professional orchestras I worked for. Both were in the early stages of digital transformation when I arrived. In an organization that is 100 or even 150 years old, you can imagine there are some archaic ways of operating, some steeped deeply in traditions that made sense and others not as much. And as with many not-for-profit organizations, there were significant resource constraints. So rather than hire internal teams, we worked with a lot of freelancers, small agencies, and specialty software companies.

I led a variety of projects to help transform marketing operations and customer experience for these institutions. We focused on the usability of the Website and ticketing systems, for example, with the goal of increasing ticket sales. When I started in that industry, a concertgoer could not choose the seat they wanted to sit in. Imagine paying upwards of $100 for a ticket but not knowing what the experience would be. So we customized software so a customer could pick exact seats and see a photo of the view they’d have. There was a time when you had to call customer service and an agent would describe the view to a customer. Remember those days? That wasn’t all that long ago!

We did a lot to improve the customer experience related to concert-going, which is the core business of performing arts institutions. We manually created pre-concert emails that had all kinds of helpful info in it, even telling them when the subway was bypassing the concert hall station that weekend so the customers could allow for extra travel time. This may not seem critical to digital transformation, but it goes to delighting customers: since we had to email them anyway, why not give them a heads up that there was an inconvenience to expect? And if we had not told them, the ushers would have many concertgoers showing up late which could delay the concert or annoy the customers who wouldn’t be seated until a break in the performance. Customers who have a bad concert experience may not return for another concert (or may not donate as much next year), and that impacts long-term business goals.

I also worked on the evolution of digital marketing strategies and audio and video distribution. There was so much variety in the work to be done: live webcasts of concerts (including the New York Philharmonic’s historic 2008 live broadcast from North Korea), SMS campaigns, app development, podcasts, and social media strategies for PR and marketing teams. These were broad-ranging transformations and have continued for many years by talented, strategic staff and partners who were passionate about the transformation of these institutions.

Has integrating Digital Transformation been a challenging process for some companies? What are the challenges? How do you help resolve them?

It is almost always challenging, because companies are powered by human beings and humans fear change. If you have ever heard someone say, “Well, we’ve always done it that way,” then you know what I’m talking about.

  • The most common challenge is mindset. One of the reasons we see a lot of innovation groups and incubators within large corporations is because changing the mindset of tens or hundreds of thousands of employees takes time. If you start with a smaller group and show some wins, you can then take those ways of working and new products to other divisions and try to cross-pollinate the transformative approach. Let me be clear that this does not always work, but it is a less expensive way to transform an entire business. I have seen success by using small, embedded groups within a company. Start with a small team, say 12–15 people, and train them to adjust the way they think and change the way they approach their work. When that teams starts to deliver results, leaders can use the successes to evangelize change in another group, and then another, until you have all the biggest revenue driving divisions working in these new ways. I recommend starting with a low-risk group that does not have the highest revenue impact but can show growth potential. When I was at Time Inc., we did this with the Lifestyle group first as opposed to News, Sports, or Entertainment, for example. The results changed the way the company did business.
  • The next biggest challenge is usually budget. Companies underestimate what it will cost to innovate and transform, or they simply refuse to commit more, and then they are disappointed when they don’t get results that keep them competitive. The VCs and startups that are about to disrupt your business are not holding back when it comes to budget. If a VC firm gives a startup $250 Million to try to solve a customer problem, can you really afford not to spend the same? You must spend money to make money. And that is especially true in our current environment, where massive, established industries are being disrupted all the time.

Ok. Thank you. Here is the primary question of our discussion. Based on your experience and success, what are “Five Ways a Company Can Use Digital Transformation To Take It To The Next Level”? Please share a story or an example for each.

  1. People First — Hire team members and leaders with exceptional human skills, not just technology skills. Digital transformation requires a lot of collaborative work, and if you have a whole bunch of experts who cannot or will not work well together, the results will reflect that. Depending on the size of your organization, try to hire a range of experience levels. I have worked at companies where they only had executive directors and early-career individual contributors and nobody in between. You need experienced talent to mentor and advise the junior employees on best practices and establish proven ways of working. 
    -Hire teams with cognitive diversity in mind. Diversity of thought is critical to successful innovation and transformation. Just like you cannot solve old problems by doing the same things you’ve always done, you cannot innovate with a homogenous team. Teams need multiple perspectives from people who have a variety of life and professional experiences. That might mean hiring people from a variety of industries to bring knowledge from those industries to yours. And it could mean being gender balanced, racially and ethnically diverse, and hiring employees from different generations.
  2. Culture of Experimentation & Data Obsession — Leaders need to create a culture of experimentation and data obsession and build failure into the process and budgets. Once the process is well established and working as designed, leaders must get out of the team’s way. The best leaders understand this philosophy and are clear about what kind of reporting they need and how often so they are informed and can adjust where necessary. When executives try to get in the mix, it is usually counterproductive. If you do the other 4 steps I’ve outlined here well, you will not need to micromanage.
  3. Mindset — Mindset is important to all work, and digital transformation is no exception. Make sure the team who is responsible for transformation efforts understands what is expected of them and has the mental and physical tools to do the work well. Also, the mindset needed to start an initiative is often different than the mindset required to scale one. Leaders need to prepare to be wrong and know when to walk away from an idea or a product that’s served its purpose. There is a reason why the Silicon Valley ethos is to fail early and often. Failure must be part of the process so that people do not mentally shut down when some of their ideas don’t work. Disengaged innovation teams are not productive. A growth mindset supports the culture of experimentation being created.
  4. Invest Wisely — Put your money where your mouth is: if you decide to invest in digital transformation (which you absolutely should), make sure you are setting your people and teams up for success. As I said earlier, the companies preparing to disrupt your business and your industry are not holding back. Could the taxi and limousine commissions of various cities in the U.S. have created Uber? Maybe not, but they certainly did not invest any money trying to meet customers’ changing needs. Which brings me to my final recommendation.
  5. Customer Focus — Establish and maintain a business focus on solving your customers’ problems. Remember why you are in business in the first place. Your business provides services and products that your customer wants or needs. If another company does it better, you will lose the. I have seen this firsthand at numerous companies who were unsuccessful in making the economics of meeting customer needs work out for the company and the customer. Digital publishing is a great example. When media companies started to struggle with debt and falling revenue, they added layers upon layers of paid ad products on their Websites and apps, to the point where consumers literally could not see the content. I remember sitting in focus groups and user research sessions where customers would try to explore a website only to have the recipe they were reading get covered up by ads and auto-playing commercials. How is a customer supposed to react to that? Many companies put short-term revenue goals above long-term customer needs and guess what happens? The customers find another place to get what they were getting from your company. The publishing example goes another level deeper, because eventually Google started penalizing websites that had too many ads and bad user experiences, pushing those sites “down” in search results, leading to increased competition from — you guessed it — emerging competitors who didn’t have 13 ads on every page. So eventually those competitors started getting the organic traffic these legacy media companies had counted on, lowering their revenue still further.
    Don’t ignore your customers. They are too smart to stick around when others will meet their needs. No brand is immune to this.

In your opinion, how can companies best create a “culture of innovation” in order to create new competitive advantages?

Hire the right people and make sure that your leadership team is truly fostering a culture of experimentation, not just paying lip service to it. Those are both critical to creating a culture of innovation. And as I said earlier, get out of the team’s way. It is vitally important that executives are invested in the work their innovation teams are doing, but that they empower them to do the work.

Innovation teams need to experiment. They need to try things that fail, so they can find the winners. As Einstein said about his so-called lack of results, “Results! Why, man, I have gotten a lot of results! I know several thousand things that won’t work.” Allow your innovation teams to identify tactics that won’t work so they can create solutions that will.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

Here are two related quotes.

“Our life is what our thoughts make it.”

— Roman Emperor Marcus Aurelius

“Your beliefs become your thoughts, your thoughts become your words, your words become your actions, your actions become your habits, your habits become your values, your values become your destiny.” — Gandhi

I am a recent convert to the values of Stoicism and a longtime yoga devotee, so I find a lot of valuable lessons in the words of ancient philosophers. How you talk to yourself and what you spend your days and nights thinking about becomes your reality. There is a lot of research that confirms this in modern cognitive psychology as well. My husband always says, if people want to be miserable, they can be miserable. But I choose otherwise. And I hope others do the same.

How can our readers further follow your work?

I am active on LinkedIn and write articles on Medium. And my business Website links to everything I do.

Thank you so much for sharing these important insights. We wish you continued success and good health!

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