Speaker Spotlight: Soft Skills Training CEO Diane Wilbur

I had the honor of getting to see Diane Wilbur facilitate a leadership development corporate training last October 2018. I could not wait to experience Diane “live,” as our dozens of coffee dates the months prior left me with a strong feeling that what I would experience would be truly incredible.

I was right.

Within minutes of Diane beginning her presentation on communications skills enhancement, she brought the group to life. Diane was the last presenter in a three day-corporate workshop—only her presentation standing in the way of the group’s trip back home—but the energy in the room felt like Day 1. Diane had the group up and about, trying out non-verbal and verbal strategies and techniques live. She had created a safe space in the room for attendees to dive deep into somewhat vulnerable facets of their leadership presence (eye contact, body language, speech patterns, etc.). I remember sitting there making a mental note: I need to bring Diane in front of the Women in Leadership Nexus.

Fortunately for me, Diane said “yes” and will be one of our featured speakers for our next event, taking place Sept. 27, “Intentional Leadership: Own Your Potential.” Diane, CEO of Soft Skills Training Group, has spent more than 20 years focusing on Talent Development and helping hundreds of professionals unlock their maximum leadership potential.

I had the pleasure of sitting down with Diane in advance of her speaking to our group, picking her brain on everything from her driver to start Soft Skills Training Group to some of the biggest leadership blind spots that face women, in particular. Check it out!

To begin, can you tell our readers about your background and how that ultimately led you to starting your own business?


I guess you could call me one of those “accidental entrepreneurs” because it wasn’t a long-term vision that took me on this journey. I’m someone who has always enjoyed work and really what you call a “lifetime learner.” I know it sounds crazy, but I don’t think I will ever retire! I was one of the first “paper girls” landing my first job in sixth grade and plan to work until the end.

I spent most of my early career in highly technical fields that were dominated by men. First as a CPA working in the “Big 8” at KPMG and Ernst & Young and later as a financial advisor and sales manager with Fidelity. I was always drawn to the people side of the business as opposed to the technical aspect of my previous roles. I was promoted to a senior leadership position and quickly recognized that my heart was in developing people—not the numbers—so I found the perfect role in HR and just went for it.  I didn’t think I was qualified to get the HR role because I didn’t have 100 percent of the qualifications they were looking for and, like most women, almost didn’t even apply. After dedicating so much time and effort to regulatory exams and licenses it was a big decision to walk away and focus on something totally different.

I was shocked when I landed the Director of HR role and it made me realize how much we hold ourselves back from opportunities as women. We quit before we even apply. I loved this role, but a few years later it was time for me to take a break and focus on my kids when my daughter entered high school because I didn’t want to miss these last years at home with her. Soon after, I was approached by several colleagues to do consulting work and have always had a side project going. These opportunities continued to grow over the last several years to the point where I’ve established a network of other speakers who I collaborate with to provide them meaningful work in their areas of expertise. Being able to open doors for other female entrepreneurs has become the most rewarding part of my business.

Such a wonderful story about self-belief and embracing the journey along the way! Today, you are the CEO and Founder of Soft Skills Training. Tell us about Soft Skills Training—the services you offer, the reasons for starting your company, the challenges you are solving for, etc.

When I left my corporate career, my focus was on my family and I didn’t have a business plan but I was approached immediately with consulting opportunities from the network and brand that I built in the community. Early projects ranged from personal branding and sales training to management and leadership development. I found it so powerful to be in a position of accepting or declining work if it aligned with my schedule, family needs and passion around the topic. Over the years, I’ve developed custom solutions for all types of organizations ranging from small businesses to global Fortune 500 companies.  We focus on issues that solve people problems and I can tell you that most of the big issues are indeed “people” problems!  Our requests range from onboarding new associates to working with senior executives to enhance their executive presence.


Your work gives you the chance to really develop leaders into their potential. Through your work, what have you found to be the top challenges with leaders in the workplace and how do you try to address these challenges head on?

Companies are looking for ways to retain their best people and reduce turnover costs and we create programs that develop their soft skills but also enhance their culture and employee engagement. Technology has changed the workplace in so many ways over the last decade. It has made us incredibly efficient but has negatively impacted our relationship building skills. We predict that the art of communicating in the future will require a concerted effort on maintaining human interaction skills. Just think of the last time you went to Stop & Shop; they now have robots roaming the aisles! This generation spends more time on social devices and less time face to face than any other time in our history. The long-term impact will result in the loss of basic interpersonal skills that we need to be successful.

A lot of your work involves working with women. What specific challenges do they face in their business world that perhaps are different than men?

We’ve made so much progress in the workplace, but we still have a way to go to reach an even playing field with men. I’m excited with the changes I’ve witnessed over the last few years, but women continue to struggle with confidence, visibility and senior-level sponsorship. Women tend to have a lot of mentors but need to broaden their network to gain visibility and leverage sponsors that can advocate for them at the decision table. Organizations have recognized the importance of developing women leaders and have shifted resources to support these efforts. As a result of requests from several clients, I developed the SHE Factor Program to provide women with the tools and skills they need to advance in their organizations.

Along the same vein, what is one piece of advice you would give to women who are looking to be more intentional with their leadership?


Let’s face it, we want our intentions to line up with reality, but we all have blind spots that hold us back. One of the biggest challenges I address with my clients is the ability to give thoughtful, honest and candid feedback to others. As we move up in organizations, we don’t receive the critical feedback we need to grow and develop as leaders. And entrepreneurs don’t get any formal feedback!  

In order to be intentional, you need a high level of self-awareness and that can only be achieved with reflection and honest feedback from people you trust. You don’t need an extensive survey tool to get candid feedback. An easy way to enhance self-awareness and become more intentional is to ask people you trust “What are three words that come to mind when you hear my name? What is the one area you would recommend I focus on to have more impact in my role?” This is a great starting point to identify where to focus your energy to be more intentional and to have a greater impact.

I love that advice! OK, shifting gears for a bit, how do you define leadership?

This is a really exciting time because the way we define leadership is beginning to align with traits that are typically seen as “female centric”; empathy, humility, collaboration, teamwork, relationship building skills, and the ability to inspire others. Finally, the tide is turning in our favor!

I’ve worked with so many talented leaders over the years and my view has changed on leadership. The most successful leaders I’ve coached have a strong character but also possess the passion to serve others and make a seamless transition from high potential individual contributor to someone who can lead and influence others. We are witnessing the acceptance of more innovative thinking and challenging status quo. It’s just the beginning of a turning point that will reflect how we have evolved into more diverse leadership

OK final question… what are some areas of focus for you in the coming months? What can we expect from you and Soft Skills Training?

Our focus continues to be on interpersonal effectiveness and building emotional intelligence in the workplace. Each new client brings a unique challenge for my team to solve and we look for ways to develop people to have stronger connections with exceptional communication skills. I became certified as a Body Language trainer in 2019 and have incorporated these critical elements into all of our programs. We have a big focus on ROI (with my CPA background) so our clients typically engage us for long term projects that include reinforcement so that the learning “sticks.” We are hoping to add online training modules to our library of resources for the upcoming year that clients can have 24/7 access to.


To learn more about Diane’s leadership development programing, click here.

To register for the upcoming Nexus event, taking place Sept. 27 from 8:30-11:30 am, featuring Diane, click here.

Carrie Majewski is committed to affecting change. As Founder of the Women in Leadership Nexus, Carrie is fueled by a desire to create safe space for female luminaries to convene to redefine the notion of leadership. She has forged a career around strategic writing and storytelling, having led a digital marketing agency for almost three years and today working as VP of Marketing for Trilix. Carrie is a 2017 Rhode Island “40 Under 40” honoree and a 2016 Rhode Island Tech10 Winner. In her spare time you'll find her trying out a local hip-hop class, exploring parks with her rescue dog Tori, and sipping coffee with other powerhouse women.