An Interview With Chad Silverstein
…Keep learning and growing. Read as much as you can by others who have succeeded in your field or in adjacent fields. You may be inspired to try different paths or learn how to adjust what you are doing to great benefit…
We are starting a new interview series about the world of entrepreneurship beyond the classroom — a realm where theory meets grit, and education meets real-world challenges. We want to hear about critical business wisdom that often goes unspoken in academic settings. I had the honor of interviewing Maria Leonard Olsen.
Maria Leonard Olsen practices law as a commercial litigator in Washington, DC. She is an author (50 After 50: Reframing the Next Chapter of Your Life), podcaster (“Becoming Your Best Version”), journalist, TEDx speaker (“Turning Life’s Challenges into a Force for Good”), book marketing coach for female authors and mentor to women in recovery. Learn more at MariaLeonardOlsen.com and follow her on social media @FiftyAfter50.
Thanks for being part of this series. Let’s jump in and focus on your early years. Can you share who was your biggest influence when you were young and provide specific examples of what you learned from them that helped shape who you’ve become and how you live your life today?
My grandmother was an immigrant from the Philippines. She was the strongest woman I have ever known. She was resourceful and solution-minded, and taught me so much about self-reliance and striving for what I want. Although she was considered wealthy and highly educated in the Philippines, those perceptions did not hold true when she came to the U.S. She did not let that stop her. She was unable to use her foreign university degree to secure a job here, so she took other jobs to survive. She taught me that no one can make you feel inferior without your consent. She encouraged me to go to law school and to write, and she was thrilled with my successes.
Staying on the topic of influence, who has been your biggest catalyst more recently and what can you share that you’ve learned from them that led you to making changes in your life?
I was a political appointee in the Clinton Justice Department. A partner in my law firm took me with her as her Special Counsel to the Assistant Attorney General. I had doubts that my experience thus far would prepare me for the position. She assured me that I was a quick study and would be an excellent asset to her. I rose to the occasion because of her faith in me.
In this interview series, we aim to reveal what seasoned entrepreneurs wish they had known when they were starting out and capture what the textbooks and college professors left out. Mistakes are invaluable. Can you name one specific mistake that you made early on, and learned the most from, but wish you’d been forewarned about?
I did not negotiate well early in my career. For example, salaries and employment contracts are negotiable. You can strike contractual provisions; you can ask for more. Know your worth. Do your homework and find out what comparable salaries are in your field and at your position. Otherwise, you may be settling for much less than you deserve.
Is there a leadership myth you believed early on that you’ve since debunked through your real-world experience?
Some people believe that being aggressive is a positive attribute, but it is more about being assertive. Don’t step on others. Collaborate. Try to find common ground. It is okay to erect appropriate boundaries, even in the workplace. For example, it is ok to determine when you have too much on your plate. If you are stretched too thinly, you may not do anything well. Delegate when you can. Trust, but verify the work of others if you are the team leader.
What’s the key operational insight you’ve gained since running your business that was never mentioned in any classroom?
No one makes it alone. Keep your eyes open to beneficial collaborations. Remember to keep in contact with people. You never know who might be in a position to help you one day. Networking is important.
Did college prepare you for scaling a business? What specifically was missing?
How to find a good mentor is something that was missing. One has to be assertive, creative and persistent to find the right mentors. Asking for informational interviews is a good idea. Ask someone out to coffee or for a Zoom meeting. People like to talk about themselves, which can yield important and helpful tips for one’s own work.
Any unexpected challenges in team dynamics that your academic experience didn’t prepare you for? How did you handle it?
I knew about sexism in the workplace, but there were no classes on how to handle it adeptly. Universities should consider adding strategies for coping with and overcoming sexism and other hurdles in the workplace.
Have you had to unlearn any widely-accepted business ‘wisdom’ in your journey? What was it and how did it affect your strategy?
Hard work alone does not always guarantee success. Luck is sometimes involved, and you can often make your own fortune. Often it is difficult to discern trends correctly, but not impossible. It’s also a good idea to know when to pivot. So I read as much as I can about what is happening in my field, look for areas of unmet need that I can capitalize on, and plan or re-plan accordingly.
What’s your advice for new entrepreneurs? What are your “5 Things You Won’t Learn in College But Must Know to Succeed in Business”?
1. Find a good mentor. Most people are pleased to help others. Mentors can help you navigate more adeptly, given their experience. They can be good sounding boards for ideas. Find a mentor through your alma mater, business organizations, or through networking. You can have more than one mentor.
2. Be a good mentor. Cultivate skills and talent in your company and help those who are earlier on their career paths. They may be in a position to assist you one day in ways you cannot now anticipate. Moreover, paying it forward creates good karma.
3. Network. Networking can help you stay abreast of emerging trends and opportunities. If I had not asked one mentor for a specific job, I would not have had the opportunity. She was unaware of my aspirations at the time and I got the best job of my life.
4. Keep learning and growing. Read as much as you can by others who have succeeded in your field or in adjacent fields. You may be inspired to try different paths or learn how to adjust what you are doing to great benefit. I listen to TED Talks as I get ready for the day, which are motivational and eye-opening. Sign up for continuing education opportunities. No industry is static and you will be better at what you do by keeping current.
5. Don’t let mistakes hinder your goals. We can learn from any mistake. Every situation has the capacity to teach you something if you are open to the lesson.
How do you ensure your team not just understands but embodies your business principles? Any techniques you wish you’d known earlier?
Having regular opportunities to check in with people on your team is important. Make yourself accessible. Know your team and demonstrate that you care about them, to increase loyalty and team cohesiveness.
If we were sitting together two years from now, looking back at the past 24 months, what specifically has to happen for you personally and professionally, for you to be happy with your results?
That I did work that made a difference in the world, that I stayed true to my values, and that my next book was a bestseller!
Looking back over the last two years, what key accomplishments make you satisfied with your progress?
My book 50 After 50: Reframing the Next Chapter of Your Life helped so many people get unstuck and elevate their lives, I finished my next book manuscript, and I gave a series of well-received public speaking events. Being published can increase your visibility and give you additional credibility. In my legal work, I achieved great results for my clients. I also was able to mentor some young women in their careers.
As someone with significant influence, what’s the one change you’d like to inspire that would benefit the most people?
Treat others with kindness, no matter what. There is enough hate in the world.
How can our readers keep up with your work?
My website is www.MariaLeonardOlsen.com for writing and www.PelsLaw.com for legal work. My social media is @FiftyAfter50. My Becoming Your Best Version Podcast can be found on Spotify or Apple Podcasts.
Thank you so much for joining us! We wish you only success.
About the Interviewer: Chad Silverstein is a seasoned entrepreneur and Thought Leader with over 25 years of business experience. He has founded, operated, and exited multiple companies and now builds into a handful of high impact CEOs. Chad has launched multiple online communities, including a recent leadership development platform, and also serves as a strategic advisor for Authority Magazine’s thought-leader incubator program.
To learn more and connect with Chad visit: chadsilverstein.io
Maria Leonard Olsen On 5 Things They Forgot To Mention In College was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.