Michelle Boockoff-Bajdek of Skillsoft: Why It Is So Essential To Lead With Passion

…when you do lead — lead with passion. I am particularly passionate about this topic and it’s become one of the most important aspects of my role: helping to teach people how to build, manage and lead effective teams. Engaged employees — who are well-managed, understand their role in the organization and the importance of their contributions, are clear about the path they are on, and ask for regular feedback — perform at a much higher level.

I had the pleasure of interviewing Michelle Boockoff-Bajdek.

As Chief Marketing Officer, Michelle Boockoff-Bajdek (BB) leads a global marketing organization focused on helping companies unlock the hidden value inside their greatest asset — their people.

In her role, Michelle is responsible for the company’s marketing strategy to drive growth, generate awareness, and drive demand for Skillsoft solutions among learners, customers, and partners. She oversees all key functions, including customer marketing, corporate communications, demand generation, marketing operations and business development. Most importantly, she serves as the company’s brand evangelist, helping to build a vibrant community of passionate learners.

Prior to Skillsoft, Michelle held several executive roles in the high tech sector, most notably as the CMO of IBM Watson, where she was responsible for marketing the company’s artificial intelligence (AI) products and solutions. Michelle also served as the global head of marketing for The Weather Company, an IBM Business, where she helped companies understand how to anticipate, plan for and ultimately make better decisions — with greater confidence — in the face of weather.

Michelle is a prolific speaker on the topics of emerging technology and marketing trends, and a passionate advocate of the advancement of women in business. Michelle holds a Master’s in Communications Management from Simmons College and sits on the pro-side of the Oxford comma debate.

Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

Of course. Most people call me Michelle BB and I am the Chief Marketing Officer of Skillsoft, a global digital learning organization that helps companies unlock the potential in their most valuable asset — their people — through engaging content and powerful technology. My career has taken me down so many exciting paths and I truly believe I’ve found my calling in marketing.

Before Skillsoft, I spent almost five years at IBM as the result of the acquisition of The Weather Company (The Weather Channel) and had the opportunity to serve most recently as the CMO of IBM Watson, responsible for a portfolio of products that leverage artificial intelligence to help businesses make better decisions. I was also responsible for the company’s overall positioning of AI and served as the steward and shepherd of the Watson brand.

I’ve always been fascinated by the impact technology has on our daily lives at work and at home. And, learning has been a common theme throughout my career. At Skillsoft I get to focus on the perfect combination of both: technology and learning. In all my roles, I’ve had opportunities to research and discuss topics I have a passion for, like the need to close the skills gaps, drive stronger adoption of learning initiatives, elevate female voices in leadership, and transform talent across a multi-generational workforce.

But, I am a marketer at heart; it’s always been in my blood. My mother, who started as a programmer for NASA, built a successful career as a product marketing and product management executive for several technology companies. My own love of marketing grew once I returned from a stint in sales and sales leadership. Working closely with clients was a wonderful experience and gave me tremendous perspective. I became a better marketer as a result — and far more passionate about the impact we, as marketers, can have on a business.

Can you share the most interesting story that happened to you since you began leading your company?

I’d been the CMO at Skillsoft and SumTotal for approximately six months. The most important initiative on my list (besides launching a new brand, staffing up a global department, running a dozen concurrent marketing programs, and scheduling foot surgery) was Perspectives, our annual user conference. Perspectives brings together customers, partners, and industry visionaries to showcase how organizations are building transformative learning and development programs. It was to be a thoughtful and high-end, but fairly conventional, event: with live programs in Florida, London, and India. And we had lofty goals to increase participation by 25% to more than 1,200 attendees, aggressive but achievable.

Then everything changed.

The first week of March, the Covid-19 pandemic became a reality for those of us in the United States. In short order, we were advised to stay at home and adjust to remote work. Suddenly, a live destination event was more than a challenge. It was an impossibility. I’m not sure that anything could have prepared us for the nature of this crisis and the immediacy with which we had to act. Our ability to adapt — and adapt swiftly — was paramount.

We took the opportunity to shift our thinking entirely and reimagine what a digital experience could be. Going digital had to be about more than just moving an in-person event onto an online platform. We had to create something completely new and irresistible that encourages people to participate live. So we spent 28 hours over two days in a design thinking workshop, including members of our customer communities to determine what they wanted from a modern digital experience. We also looked at examples of companies that have held successful live experiences across industries and sought inspiration in some unusual sources — from Peloton’s annual Homecoming, Apple and their infamous product unveilings, and even television’s The Bachelor, which uses social media to drive tune-in. It was an exercise in being agile and creating something entirely new out of a less-than-ideal situation. And we recognized that we had an opportunity to open our aperture and turn this limited, in-person regional event into a global day of learning for everyone.

Over the following two and a half months, my team worked — sometimes day and night — to reinvent Perspectives from top to bottom. It became a free, 24-hour, online experience, starting in Sydney, Australia and wrapping up in San Francisco, California. Perspectives 2020 featured more than a hundred speakers in keynotes, case studies, and head-to-head debates. There were product demos and regional business continuity panels. There were music and yoga breaks, and ample opportunities to ask questions, suggest solutions, and participate in what turned into a 24-hour conversation about everything from personal development to diversity and inclusion training; from leading in challenging times to lively discussions on who owns the skilling agenda.

By transforming Perspectives 2020 into a digital experience, we were able to live our mission by democratizing learning, making it available and accessible to all of our 40,000 registrants.

The single biggest takeaway for me was that this was not just about teaching people new skills; it was about improving our collective well-being — developing the whole person. If there’s anything the pandemic has shown us, it’s that the line between the personal and professional is — and should be — flexible. When we continue to learn and grow and achieve, it benefits our work life and our home life. This was a theme that surfaced over and over at Perspectives 2020: holistic learning. And this is precisely who we are and what we do.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I’m not sure I can recall my funniest mistake (I doubt any mistakes felt funny at the time), but I can tell you that I definitely learned the most from the really, really painful ones. And often, they occurred when I didn’t listen to my internal compass and let others lead when I knew we were headed in the wrong direction or at moments when I wasn’t fully present. The latter has been a hard one for me. We’re bombarded by constant meetings, emails, requests for time… I find that even today, if I am not disciplined about how I approach my time, or if I try to do too much and am distracted, I am far less effective. So, the moral learned? Be present.

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 about that?

One of the most important lessons I learned while at IBM came from Ginny Rometti, the Executive Chairman and former CEO. She often talked about the fact that our reality is rooted in change and disruption. Rapid change. As you likely know, IBM over the course of its 100-plus year history changed dramatically — from the tabulation era to personal computing; from e-business to now Cloud, AI and quantum — it’s a company that has always shifted to meet the needs of its customers. And while we’ve talked about these shifts in the past, they’re more relevant now than ever. Change is happening all at once — and the pace is unabated — as we face one of the biggest global crises of our lifetime. It’s forced everyone, at every company, at every level to rethink the way we work. But, Ginni advised us to recognize and differentiate between what must endure and what must change.

In my work, I often talk about how to release and relieve stress. As a busy leader, what do you do to prepare your mind and body before a stressful or high stakes meeting, talk, or decision? Can you share a story or some examples?

For me, it’s all about the morning. This is when you set the tone for the entire day, so you have to make it matter. I make it a point to do something for myself or my family that starts the day off on a positive note. In my case, that means firing up the Peloton, but there are so many ways to make the best of the morning. Take your java on a brisk walk, cook a fancy breakfast and enjoy it with your kids or partner, or do a quick straightening up. Even popping in a load of laundry can be an act of self-care if it takes one more thing off an already crowded plate.

As you know, the United States is currently facing a very important self-reckoning about race, diversity, equality and inclusion. This may be obvious to you, but it will be helpful to spell this out. Can you articulate to our readers a few reasons why it is so important for a business or organization to have a diverse executive team?

I think we all recognize that a more diverse team can offer more objective, versatile, and creative solutions, which result in better products and services. But just giving people a seat at the table isn’t enough. Diversity, equity, and inclusion — or DEI — should not be addressed as a special interest or a separate topic any longer. Genuine diversity, real equity, and meaningful inclusion is not a destination we can reach overnight. It takes deep conversation and even deeper listening, changes in hiring and development strategies, honesty and self-awareness, and a commitment — at both the individual and the organizational levels — to changing the status quo and building something that’s better for every person, at every level, every day.

As a business leader, can you please share a few steps we must take to truly create an inclusive, representative, and equitable society? Kindly share a story or example for each.

It can’t just be politically correct rhetoric. Diversity, equity, and inclusion go beyond building a culture where people “fit in” — it’s about building one where every individual can meaningfully contribute. Give them the tools to engage with their work, colleagues, and leadership. It needs to permeate every phase of the organization, and notably within the employee lifecycle — from recruitment to retirement, including training, rewards, and recognition.

At Skillsoft, we recognized that achieving a culture of true DEI was a journey; and we’re not there yet. But, we’ve recently launched four initiatives of which I’m very proud. First, we’ve created a Leadercamp series, partnering with renowned authors and diversity coaches. Next, we’ve started publishing reports, the Skillsoft 360 Series, designed to challenge assumptions, consider subjects from multiple angles, and provide a fresh, yet comprehensive, view of this timely topic. Third, we encouraged our entire global staff to use Juneteenth, Emancipation Day, as a day of self-reflection and learning; nearly 1,400 people participated in DEI discussion forums. And, finally, to promote enduring change, we launched a new Inclusion Council, made up of diverse members of our community whose mission will be to ensure Skillsoft is a workplace that’s inclusive and rewarding for all.

When a work culture is welcoming and demonstratively values diversity and inclusivity, it can make a world of difference in terms of allowing people at all levels to be heard. Communication here is key, because the organizational culture has to be equipped to address employee needs and provide people with the tools to enable and foster open dialogue. And now more than ever, we have to do that through virtual channels, which means that we have to be even more mindful and, in a lot of cases, over-communicate.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. Most of our readers — in fact, most people — think they have a pretty good idea of what a CMO does. But in just a few words can you explain what an executive does that is different from the responsibilities of the other leaders?

Basically, CMOs are responsible for overseeing all key functions of marketing: including customer marketing, corporate communications, demand generation, marketing operations, and business development.

But, the CMO role has evolved to be more about delivering an exceptional customer experience. Sometimes that means re-educating internal leaders so they embrace the idea that we’re not selling what we have; we’re providing what customers need. It’s understanding our customers like never before, being laser-focused on the customer experience, and re-imagining how we engage with the consumers who touch our brands every single day.

A CMO is also the company’s brand evangelist — in my case, helping to build a vibrant community of passionate learners, delivering real benefits to real people all the time.

What are the “myths” that you would like to dispel about being a CMO. Can you explain what you mean?

No one day is the same, I’ll tell you that. Some might assume that CMOs sit in a corner office at the corporate headquarters coming up with strategies. But, my best days are those spent with clients and partners. I also think the concept of brand is misunderstood — it’s often seen as a static entity, rather than a living, breathing mission that is shaped — positively or negatively — at every single touch point. For me, it’s a tremendous honor and privilege to build and protect the Skillsoft brand. And all of us in this organization carry that responsibility — to be good stewards of the brand.

In your opinion, what are the biggest challenges faced by women executives that aren’t typically faced by their male counterparts?

I’ll answer this question with a story: one of the biggest moments of my career thus far has to be working on the Women in AI program at IBM. AI is an actual reflection of who we are as people. These systems are trained by human beings, but the field is largely dominated by men. As the technology becomes more pervasive, there is greater opportunity for bias that could impact anything from HR and recruiting, to customer service. To me, it was very important to voice the value of making sure this technology is developed with a diversity of thoughts and perspectives. This is a challenge that I, because of my gender, was acutely aware of and, as a result, passionate about solving. More than anything, it highlights the need for diversity in leadership — we need equal representation.

Certainly, not everyone is cut out to be an executive. In your opinion, which specific traits increase the likelihood that a person will be a successful executive and what type of person should avoid aspiring to be an executive? Can you explain what you mean?

First, seek to understand the role. What does it mean to become a leader? I often have people ask me about career advancement and what they need to do to get a promotion, and the first thing I ask them is if they understand what that promotion or new position will mean for them, what responsibilities they’ll have. And then I ask them what they feel they need to do to get there.

Job descriptions are often woefully inadequate when it comes to outlining the reality of a day-to-day executive or leadership role. There are specific responsibilities, of course, but there are also softer skills that don’t come naturally to everyone, like mentoring, coaching, and problem solving. It’s unfortunate that we all assume that becoming a leader should be a goal for everyone. Some people are much more successful as subject matter experts or individual contributors. Some of the smartest people in technology and medicine, for example, might have genius IQs and be terrible at communicating.

What advice would you give to other women leaders to help their team to thrive?

In my experience, there are keystone skills that unlock access to myriad others. For example, there is tremendous value in adopting a growth mindset. Seek continuous development, look for new opportunities, and open up to new ways of thinking. From there, the possibilities are endless. For marketers specifically, I would say some of the best skills to foster are curiosity, listening, and awareness. Ask questions; don’t make assumptions. Really listen to customers; be aware of what they want and what they need. All of this is critical to ensure marketing is done side-by-side with them, not pushed towards them. Especially in times like these, where so much is uncertain and changing every day, it’s important not to create problems and present your brand as the solution — instead, take the time to uncover their true needs and understand how you can help.

How have you used your success to make the world a better place?

At Skillsoft, our mission is to democratize learning. As the adage says, knowledge is power. Skills development is quite possibly the most powerful tool each of us have in our roster. I mentioned our digital experience earlier, Perspectives 2020. It was by nature, originally designed around industry attendees: C-suite executives, HR professionals, and managers. Since reimagining it into a fully digital experience, we were able to expand the audience that we’re serving — and we designed the experience to reflect that. We’ve created a breadth of content with learners in mind, from employees to college students. This content was — and because it was virtual, still is — entirely free and accessible in real time. A digital experience means that world-class learning isn’t reserved for those who are sent off-site by their company: it’s for everyone.

What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

1. We’re human. Embrace it. This is especially top of mind right now. As we’re all working remotely, every video call provides a peek behind the curtain. Barking dogs, kids on the phone, you name it. The chaos isn’t going away anytime soon, so it’s more important than ever to welcome that chaos and let it remind us of our humanity.
2. Cross-skilling is key. As I mentioned earlier, I had the opportunity to take on a sales role and work more closely with clients; it was a wonderful experience and gave me tremendous perspective. I became a better marketer as a result and far more passionate about the impact we, as marketers, can have on a business.
3. Find a mentor. Find someone who is currently in a similar role, outside of your department, and ask them to serve as a mentor. It helps to have someone who can help you better understand the role and skills required.
4. When it comes to leadership, take your time. I wish I hadn’t taken on a management role as early in my career as I did. I believe we need to do a much better job preparing people to become first-line managers, investing in them. Talent is so critical to organizations and the experience people have with their managers shapes their career, bolsters their skills, and ultimately contributes to their satisfaction.
5. And when you do lead — lead with passion. I am particularly passionate about this topic and it’s become one of the most important aspects of my role: helping to teach people how to build, manage and lead effective teams. Engaged employees — who are well-managed, understand their role in the organization and the importance of their contributions, are clear about the path they are on, and ask for regular feedback — perform at a much higher level.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.

One thing I’ve always held consistently is a passion for learning and a desire to gather and hone new skills. When I came to Skillsoft, I saw an opportunity to serve and share the power of learning around the world — but, it was also an opportunity to join a company whose culture is centered on learning as a core value. I’ve spent many years working with some of the greatest minds in the world and one thing they all have in common is a passion to always ask “Why?” or “What’s next?” It’s made me see the value in never settling, never thinking you know enough. There are always opportunities to learn and grow. I do the work that I do at Skillsoft to inspire people to grow — to realize that it doesn’t matter what your position is, your possibilities are unlimited if you take the initiative to take on new challenges and better yourself through learning.

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

“Nothing grows under a Banyan tree.” It’s an Indian proverb and something that a former CEO and mentor told me. I tend to jump in feet first and get things done. But, managing a team, you have to sit back and let others work and learn and shine. By taking on too much myself and sheltering them from feedback (positive or negative), I was doing them a disservice. I was the Banyan tree, and I needed to know when to move aside and let them grow.

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

I would be honored and humbled by the opportunity to thank Mayor Keisha Lance Bottoms for her courage, her leadership, and her humanity in the face of a national crisis. She has demonstrated grace under fire, even as her own governor sued her for mandating masks. I am also impressed by, and would love to thank the Governor of Rhode Island, Gina Raimondo, for her tenacity, resilience, and fortitude in the face of a global pandemic. She researched countries that had successfully battled the virus and set out to bring some of their best practices to RI, and the United States. She convinced CVS to make COVID-19 testing more widely available and leveraged the National Guard to create drive-through testing sites. And perhaps most boldly, she reached out to Salesforce.com to design contact tracing software. It would be an honor to spend even five minutes with these women who are making a difference in our world today.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.