The importance of networking. I think I learned the art of networking a little bit too late. Learning how to connect well with others, especially strangers, is a skill and art. It’s important early on in a career to master this because it can truly help in career development. However, it isn’t a skill that comes naturally for me, and it involves having confidence. I wish I would have learned sooner how to use LinkedIn, how to connect with people, how to attend networking events and how to really help build new professional relationships. I wish I would have pushed myself out of my comfort zone a little earlier on in my career.
As part of our series called “5 Things I Wish Someone Told Me Before I Began Leading My Company”, I had the pleasure of interviewing Amy Westby, Executive Director of Strategic Initiatives, Education, and Philanthropy, The NSLS & The NSLS Foundation.
As the Executive Director of Strategic Initiatives, Education and Philanthropy at the National Society of Leadership and Success and its Foundation, Amy oversees the programming and advancement of education for thousands of students each year, who are committed to leadership development and community commitment.
Prior to the NSLS, Amy taught and served in educational leadership roles on several continents in addition to American public, private and charter schools. In her role at the Character Education Partnership, Amy addressed conference topics on social and emotional development, facilitated discussion panels on ethical leadership and character development, and traveled the country seeking out top-notch schools that demonstrate quality leadership programs.
Amy spent 15 years working as the director of education and the director of international sales for a large, educational travel company. In addition to developing the education product and managing a team of 50 sales employees, she oversaw programming for all divisions across the company from elementary to executive education programs. Recently, Amy spent the last five years of her career working as an executive director at several non-profit organizations focused on equity in experiential education and serving people of all economic backgrounds and disabilities.
As an advocate for higher learning, Amy has also taught several college-level courses as an adjunct professor at The University of Virginia, in Charlottesville, Virginia. She holds numerous certifications from professional organizations including the International Baccalaureate Organization and the Colorado Center for Non-Profit Management and Leadership. She currently leads a personal consulting agency and serves as a Board of Trustee member for various organizations and associations of accredited schools, overseeing more than 1,200 international, distance education, travel study and other unique schools worldwide.
Amy holds a B.A. degree in secondary education English and history from Bethel University in St. Paul, Minnesota, and M.Ed. and M.A. degrees from the University of Minnesota in comparative international education and development and education administration and leadership. She has taught English, humanities and history and has served in numerous development and school administration roles in Minnesota, Texas, Kuwait and Malaysia.
In her spare time, Amy loves to travel and spend time outdoors. Her love and joy rest at home with her daughter, Liliana.
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 always knew I was going to be an educator, so it was no surprise that I pursued an education degree in college. Even when I was little, I would line up my stuffed animals into “classroom rows” and teach them about all things life related.
Following graduation, I had a wonderful hiring experience, as at the time, school districts were clamoring for educators, and I could pick every course I wanted to teach. I chose to teach History and English for 11th and 12th grade, and I even asked for an extra open period so I could lead the extracurricular activities at the school such as National Honor Society, Model United Nations, Service Learning, Student Government, and the prom committee. I wanted to learn everything and spend all my waking time being with the students. I also volunteered to join the Blue Ribbon Committee, which provided me with a wonderful entry into school accountability and cross-department collaboration in order to achieve success on a national stage.
Those early teaching experiences also gave me a glimpse into leadership. My first teaching principal had a profound impact on me. She arrived at school every day at 4 a.m., as her philosophy was to focus on her project time early in the morning and her relationship time with teachers and students during the day. She would then spend time at home with her family in the late afternoon and evenings. I saw her ability to balance her life and work duties in a way that resonated with me, and I quickly became an early riser, often arriving to school at 4 a.m. as well. Her philosophy has helped guide me on how to successfully balance my family and professional career.
My first experience teaching high school also prompted me to always strive for more. After several years of teaching, I expanded my educational experience and pursued a number of different roles in California, Colorado, Minnesota, New York, Texas, Virginia, Washington, D.C., Kuwait, and Malaysia. In addition to professional development, I have always been in pursuit of personal growth and learning. I’m grateful that my career has always allowed me to take on more, focused both on education and my true passions.
What was the “Aha Moment” that led to the idea for your current company? Can you share that story with us?
When I joined the National Society of Leadership and Success in 2017, I quickly realized this was a special leadership and teaching community. The “aha moment” came upon my discussions with the team about adding more enhancements to the organization’s learning journey. This discovery also included the pursuit of an educational accreditation for the NSLS, which I willingly and excitedly took on. I had asked the open-ended question: “If we could reinvent leadership development for the 21st century, what does that look like?” With that, we began to rethink the system and the foundation of our work and of our organization. As a team, we learned what a quality curriculum looked like and how it could be implemented using new resources and technology. We additionally realized taking assessments of our curriculum and programming — and its impact — could help us pursue more educational and instructional opportunities.
Since 2018, we have become the first accredited honor society, offering new programs to thousands of students daily. Our assessments have shown the impact our programming has had on our students, who continue to transform their leadership abilities into new career opportunities. Through this process, we have most importantly learned a great deal about ways to reshape all facets of our work, and we continue to demonstrate our ability to pivot as needed and take critical and significant steps forward.
Can you tell us a story about the hard times that you faced when you first started your journey? Did you ever consider giving up? Where did you get the drive to continue even though things were so hard?
The most challenging times in my professional journey has been centered on balancing work and home life. As a single mother raising my daughter, there has always been a pull of focus between work and home. Trying to give time to both is near impossible — and certainly an emotional and physical challenge — but both are important. I remember when my daughter was a toddler. I would drop her off at daycare, drive an hour commute, work hard all day and then travel another hour to make it back to daycare before the pick-up deadline. I would then spend the next few hours with her, and as soon as she went to bed, I would work late into the next morning, just to have to do it all over again the next day. It was exhausting, but I was able to get through it because I was able to understand and realize that time was passing and that this circumstance wouldn’t last forever. I forecasted out the year ahead and used that time to plan my next move where I knew it would be easier. I also used my two-hour commute to think and remind myself how grateful I was to have a job, a healthy daughter and a future. I am a planner, and a big takeaway for me during this period of my life was the importance of organization and coordination in both my personal and professional life.
So, how are things going today? How did your grit and resilience lead to your eventual success?
Things are much better, and the hard work paid off. Eventually, I was able to earn the trust of the company I worked for at the time through my dedication, which afforded me the opportunity to work remotely and have more time with my daughter. As I transition my professional career alongside my daughter’s own development and age, I have had to adjust my working style and find new ways to “weave in” my motherhood into video calls and weekend work. Flexibility has been the key. There is always a tradeoff, and the best learning lessons come from being able to pivot and grow as a leader. Throughout my career, by being able to balance motherhood and my profession, I was able to take control of my destiny through hard work, always proving my value and strong organizational skills.
What do you think makes your company stand out? Can you share a story?
The NSLS has a long-standing history of stability and deep programming that is transformative and life changing. Our company stands out because of the relationships we build and establish with our participants. We offer a component of professional development that is truly valuable to so many people — leadership. We have grown in our ability to provide our members with many skills and values that propel them into new opportunities, and it’s their success stories that remind us at the NSLS what we are doing is truly important. The NSLS is creating a new kind of leadership development mindset for all. Our curriculum is unique in what we teach and how it is structured for delivery. As our participants move through our programs, they have increasingly more choice in what they learn and how they engage with us.
Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lessons or ‘takeaways’ you learned from that?
I remember numerous times when I overpromised a deliverable and found myself scrambling to complete it. This has ended up with some funny snafus. I have learned through all of them the importance of planning ahead and keeping it simple! I once decided to make special fortune cookies for our team (of 400) with motivational sayings in each one. After the first batch went very awry, I scrambled to find a bakery to make them for me at the last minute. It was a bit foolish and reminded me that the best leadership comes from listening, empathy and compassion — not from a fortune cookie. I spent a lot of time wasted on that endeavor versus having coffee with a team member or spending an extra 10 minutes in a one-on-one conversation. Over the years, I have learned how to be an authentic leader by being myself and realizing the bells and whistles, quotes and jargon are not always needed.
Often leaders are asked to share the best advice they received. But let’s reverse the question. Can you share a story about advice you’ve received that you now wish you never followed?
You’re right. Sometimes not following the advice given is the best advice. In my case, “block time on your calendar to find work-life balance” is the piece of advice I thought sounded good, but in reality wasn’t for me. I spent a lot of time over planning, blocking out my calendar and trying to communicate my schedule with my teams, only to end up changing, adjusting and spending double the time to re-doing everything! Instead, I have learned how to get the job done. Period. Full stop. Sometimes, it means working until 3 a.m., and other times, it means starting the project earlier than expected. In the end, I make sure I have time for all my priorities in a day, and not spending time over planning has been the best plan for me.
You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?
Hard work, optimism and organization.
My father taught me to work hard. He was loyal and diligent about being on time, working hard and developing relationships with those around him. I started working when I was 15, and I found joy in the success of doing a good job.
Optimism. I always see things with a positive attitude. I like to have a good plan and often have a back-up to the back-up, but I also know that things will always work out. This has allowed me to gain the confidence and faith that I will be okay no matter what happens. I have been laid off before; while that was a scary and emotional time for me, through my optimism and hard work, I leaned into new learnings, took classes online and was able to network and grow during that period. Without optimism that I would find a new experience, I would not have found my current role with NSLS.
Organization. I have referenced this above, but organization has been a guiding skill in my life. A motto that I follow is “Made bed, made mind,” and it is a little reminder that if I am organized in my physical space, I am usually organized in my mind and in my work, too. I like to be organized in my calendar, my files and my emails because it allows me to then focus on deeper things like relationships, projects or development.
Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?
There is so much joy in a career when one sets goals. I try to inspire everyone around me to keep reading about trends and to look ahead to the future. I thrive in becoming knowledgeable about what is around the corner and staying positive and optimistic about new experiences.
What are the most common mistakes you have seen CEOs & founders make when they start a business? What can be done to avoid those errors?
Too often, I see money spent foolishly. I am one to believe in the basics of financial growth: find ways to make money creatively, spend judiciously and save with vigor. I come with an educator’s mindset of frugality toward the mission.
In your experience, which aspect of running a company tends to be most underestimated? Can you explain or give an example?
Project management. There are numerous tools out there and available, but if a company doesn’t have protocols or processes of how to use those tools, it can be like the Wild West of efficiency. I love working with startups because they don’t necessarily have those tools in place yet, but as I’ve mentioned before, my organization skills are top-notch and always top of mind. So I love to support startups in building those protocols from the bottom up. I love to use all kinds of systems and implement efficient ways to increase productivity. There are so many tools out there now that can help, and knowing which one and how to use is a passion of mine.
Ok super. Here is the main question of our interview. What are your “5 Things I Wish Someone Told Me Before I Began Leading My Company”? Please share a story or an example for each.
Number one, I wish someone would have told me having confidence is key. I have let numerous opportunities pass me by because I wasn’t confident enough in my abilities. Or, I have not spoken up in a meeting for example, which then has led to getting passed over for a promotion. And so, it all kind of routes itself in the confidence realm. I wish that I would have had more confidence early on.
Second, I wish someone would have told me that it’s easy to go down a rabbit hole — the shiny light syndrome. I have found myself becoming mesmerized by the next cool tool or fun program, which has led me to too often wasting time. I am often reminded that it’s good to go back to the basics and get to the heart of a quality business without all the fancy gadgets.
Next, I wish that I had learned early on to take the time to get to know people. Some of my most memorable business experiences have centered around the human component — the relationships — and I wish I would have taken the time to go even deeper with people. I like to think that I have good relationships with my colleagues, creating trustworthy and caring connections.
Fourth is the importance of networking. I think I learned the art of networking a little bit too late. Learning how to connect well with others, especially strangers, is a skill and art. It’s important early on in a career to master this because it can truly help in career development. However, it isn’t a skill that comes naturally for me, and it involves having confidence. I wish I would have learned sooner how to use LinkedIn, how to connect with people, how to attend networking events and how to really help build new professional relationships. I wish I would have pushed myself out of my comfort zone a little earlier on in my career.
Finally, the last piece of advice I wish I received is learning how to ask for help. I came out of school so eager to show what I was capable of and how great of an employee I was going to be that I forgot to learn how to ask for help. This lasted for many years. I remember sitting in a meeting with a mother who was explaining something to me, and it dawned on me that I didn’t have any concept of that experience — that humbled me. I wasn’t able to walk in her shoes because it wasn’t my experience. So, I made a choice to immerse myself and try. I became a mother, and I started to learn how to empathize, to learn from others and ask for help when needed. It’s made a huge difference in my life and is one of those things that is a really great skill that doesn’t always come naturally for many but is a real blessing when it does.
You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂
I know this is going to sound like a cheesy answer, but leadership. The work I am currently doing now IS the movement. Everyone, and I mean everyone, needs to know the direction of their own lives and how to achieve success. Leadership, unfortunately, doesn’t always come naturally, and the skills and values need to be taught. I am excited to share in that journey to help each person learn how to transform their lives and communities for the better.
How can our readers further follow you online?
This was very inspiring. Thank you so much for the time you spent with this!