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Catharine Montgomery Of Better Together On 5 Things They Forgot To Mention In College

An Interview With Chad Silverstein

Active Listening Skills: Success in business is as much about listening as it is about speaking. Active listening helps you understand clients’ real needs, leading to better solutions and stronger relationships. It’s a skill that requires practice and patience, but pays off immensely in understanding market needs and building trust.

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 Catharine Montgomery.

Catharine Montgomery, a seasoned communications expert and Founder and CEO of Better Together, has dedicated her career to fostering social change through innovative communication strategies in education, environment, and social justice. With a rich background in public relations, including experience in various agencies and in-house roles, she excels in creating impactful campaigns that drive behavioral change and engage diverse stakeholders. Catharine holds a Bachelor of Science in Public Relations and Marketing from Auburn University and an MBA from the University of Maryland’s Smith School of Business. She also successfully completed the Vital Voices Visionaries Program in Partnership with the Estée Lauder Emerging Leaders Fund.

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?

For me, my father was undoubtedly my biggest influence when I was young. His persistence and dedication not only to our family but to our community shaped the person I am today.

My father was and still is successful, not just in his professional life but in the way he balanced his responsibilities. He had an incredible work ethic, always striving to provide for our family. This taught me the value of hard work and perseverance. No matter the challenges he faced, he never wavered in his commitment, a trait that has deeply influenced my approach to entrepreneurship.

He was deeply involved in our local community and church, consistently uplifting young Black people. This taught me the importance of community engagement and the power of positive influence. He showed me that success isn’t just about personal achievements, but how you uplift and support those around you.

His actions instilled in me a sense of responsibility to strive for personal success while contributing positively to the world. This focus on personal and community growth is something I carry into my life and work every day through our mission and values at Better Together of using communications to achieve equity. It’s about striking that balance between achieving your goals and helping others to reach theirs, a lesson I owe to my father’s example.

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 can’t pinpoint a single individual but rather a community of people who have collectively been my biggest catalysts. This includes a mentor who encouraged me to leave my last job, investors who believed in my vision, and chief women who have both inspired and held me accountable.

One of my mentors played a crucial role in my professional and personal lives. In 2022, she urged me to think about my worth and what I deserve and have earned for my career. Instead of staying in a toxic environment, I deserved to be properly compensated. This was a pivotal moment, teaching me the value of taking calculated risks and trusting my instincts. It’s a lesson that has been fundamental in my journey as a new entrepreneur, where risk-taking is often necessary for impact, growth and innovation.

The investors who believed in my vision taught me the importance of clear and compelling communication. Their faith in my ideas provided the financial support needed as well as reinforced their belief in my vision. This has been instrumental in how I approach business decisions and stakeholder engagements.

Lastly, Chief women are my backbone providing me with a daily source of inspiration and accountability. They’ve shown me the power of resilience and the importance of holding oneself accountable for their actions and decisions. Their influence has been critical in shaping my approach to both personal and professional challenges, ensuring that I stay true to my values and goals. They also force me to acknowledge my accomplishments and take the praise that I rightly deserve.

These experiences have collectively taught me the importance of community, risk-taking, clear communication, resilience, and accountability. They have been instrumental in shaping my current path and will continue to influence my decisions and actions in the future.

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?

One mistake I made early in my career was having a defensive mindset, where I often assumed that others were trying to take advantage of me. This approach hindered my ability to build trustful relationships and limited my opportunities for collaboration and growth. I was so focused on protecting my interests that I failed to see the potential for positive, mutually beneficial partnerships.

Over time, I learned the importance of giving people the benefit of the doubt and assuming the best in them first. This shift in perspective allowed me to build stronger, more authentic connections. It opened doors to collaborations I would have otherwise missed and helped me develop a more supportive and expansive professional network. Trust and openness while not being naive, I realized, are not just foundational for personal relationships but are equally crucial in the business world.

Is there a leadership myth you believed early on that you’ve since debunked through your real-world experience?

One leadership myth I believed early in my career was that experience automatically translates to understanding. I thought that accumulating years of experience would inherently give me a comprehensive understanding of all audiences and their perspectives. However, my real-world experiences, especially as a successful Black woman entrepreneur with an MBA, have taught me that this is not necessarily true.

I’ve learned that true understanding comes from actively listening and engaging with diverse groups, not just from the number of years spent in a job. Experience is valuable, but it doesn’t automatically grant insight into how different people think or what they need. This realization has been pivotal in my approach to leadership. It has taught me the importance of remaining open curious, and committed to continuous learning, regardless of how long I’ve been in my field.

This approach has allowed me to better connect with varied audiences and understand their perspectives, leading to more inclusive and effective decision-making. It’s a lesson that is crucial in my development as a leader, emphasizing the need to listen actively and empathize, rather than relying solely on what I know.

What’s the key operational insight you’ve gained since running your business that was never mentioned in any classroom?

A key operational insight I’ve gained since launching my social-impact-focused communications agency Better Together, which was never emphasized in any classroom setting, is the principle of ‘hiring slow and firing fast.’ This concept, while seemingly straightforward, has profound implications for maintaining a healthy and productive business environment.

In the classroom, we often learn about the technicalities of recruitment and the legalities of employment termination, but the practical wisdom of taking time to hire the right people and acting decisively when it’s clear someone is not a good fit is rarely discussed. Hiring slow allows for a thorough evaluation of a candidate’s fit not just in terms of skills, but also in alignment with the agency’s culture and values. This careful selection process is crucial in building a strong, cohesive team.

The idea of firing fast is not about being ruthless, but recognizing quickly when a team member is not working out and taking prompt action. Prolonging a poor fit can harm team morale, reduce productivity, and even affect the overall business health. It’s a tough part of leadership, but necessary for the well-being of the team and the success of the business.

I’ve had to learn the hard way the importance of hiring slow and firing fast, but now that I do, it has been instrumental in shaping a productive, positive work environment and ensuring that our team remains aligned with our business goals and values.

Did college prepare you for scaling a business? What specifically was missing?

College provided a solid foundation in business principles and theories, which was invaluable, but not so much when it comes to scaling a business.

The practical aspects of scaling a business — such as managing cash flow, navigating the complexities of company culture and understanding how the real world impacts growth — were not covered in practical, useful terms. In college, case studies and theoretical models often oversimplify these challenges, while in reality, they are multifaceted and can vary depending on the industry and market conditions.

The emotional and leadership challenges of scaling a business were not adequately addressed. As a business grows, the role of the leader evolves significantly. The skills required to lead a small team are vastly different from those needed to manage an agency. Topics like maintaining company culture during rapid growth, managing increased stakeholder expectations and leading through periods of significant change are crucial topics that should be thoroughly discussed and implemented while in college.

The importance of networking and building relationships for business growth was mentioned but not emphasized enough. In the real world, connections and relationships are important to scale successfully. Learning to navigate and leverage these relationships is a skill that is often developed through experience rather than in a classroom.

While college provided a strong foundation, the practical, emotional, and relational aspects of scaling a business are areas I am learning through real-world experience.

Any unexpected challenges in team dynamics that your academic experience didn’t prepare you for? How did you handle it?

One unexpected challenge in team dynamics that my academic experience didn’t fully prepare me for was the importance of establishing and maintaining clear boundaries between myself and my employees, especially as the agency grows. In the early stages of my business, there were two of us on the team, and the atmosphere was very informal, which was beneficial for team morale and efficiency. However, as Better Together expanded, I realized that this lack of boundaries could lead to challenges in authority, respect, and ultimately, decision-making.

The transition from being a peer or a ‘friend’ to a leader requires a deliberate shift in how I interact with my team. It is crucial to establish that, while I value each team member’s input and well-being, there needs to be a clear line that differentiates professional relationships from personal friendships within the workplace. This was not about creating a sense of distance for the sake of authority, but about fostering a professional environment where roles and responsibilities are clear, and where decisions are respected and understood to be for the benefit of the company.

To handle this, I focus on clear and transparent communication. I have open discussions with my team about the evolving nature of our business. This approach helps in maintaining a healthy, respectful and productive work environment, where team members feel valued and clearly understood.

Have you had to unlearn any widely-accepted business ‘wisdom’ in your journey? What was it and how did it affect your strategy?

One piece of widely-accepted business ‘wisdom’ I’ve had to unlearn is the notion that ‘bigger means better,’ especially in the context of choosing agencies or partners for business collaborations. After working at some of the largest PR agencies in the world, I was under the impression that larger agencies, with their extensive histories and seemingly vast resources, were the default best choice for any campaign. However, experience has taught me that this isn’t always the case.

The realization came when I understood that the goals and purpose of a campaign are paramount, and the agency’s size is secondary. What truly matters is whether the agency has the specific skillset and experience that aligns with the strategic insights needed for the campaign’s success. I learned that smaller or newer agencies often bring innovative, tailored approaches that larger, more established firms may overlook or be too rigid to implement.

This shift in perspective significantly affected my strategy in how I market Better Together. For organizations and companies seeking a PR agency partner, I know they should evaluate agencies based on how well their expertise and approach align with the specific objectives of the project. I focus on this as I grow Better Together. We have led successful campaigns, as we are more agile, more in tune with current trends and more committed to delivering personalized solutions that resonate with our client’s target audiences.

Unlearning this ‘bigger is better’ mindset allowed for more flexibility, creativity, and effectiveness in who we work with and our campaigns, ultimately contributing to more impactful and successful outcomes.

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. The Art of Networking: While college may teach you the basics of networking, the real art lies in building genuine, mutually beneficial relationships. It’s not just about exchanging business cards; it’s about connecting on a personal level, understanding others’ needs, and figuring out how you can help them. This approach not only broadens your professional network but also establishes long-lasting partnerships.
  2. Embracing Risk-Taking: Business often requires stepping out of your comfort zone. While college provides a safety net, the real world demands a certain boldness to take calculated risks. It’s about making informed decisions, even when the outcome is uncertain. This risk-taking ability can lead to significant breakthroughs and innovations that you didn’t know were possible.
  3. Active Listening Skills: Success in business is as much about listening as it is about speaking. Active listening helps you understand clients’ real needs, leading to better solutions and stronger relationships. It’s a skill that requires practice and patience, but pays off immensely in understanding market needs and building trust.
  4. Having Fun: It’s crucial to find joy in what you do. College often focuses on hard work and achievement, but in the real world, taking time to enjoy your successes and recharge is vital for long-term sustainability.
  5. Celebrating Your Achievements: Learning to acknowledge and be proud of your accomplishments is essential. In the fast-paced world of business, taking the time to celebrate your successes, no matter how small, can provide motivation and a sense of fulfillment. It’s not just about reaching goals, but also about appreciating the journey and the growth that comes with it. Acknowledge all wins — large or small — and remember those when you have those good and bad days.

How do you ensure your team not just understands but embodies your business principles? Any techniques you wish you’d known earlier?

To build a solid and productive work culture at a public relations agency like Better Together, it’s essential to prioritize leadership development and purpose planning. This means fostering a culture where employees are motivated to work with a sense of urgency, not out of fear or external pressures, but of a shared desire to create something great. I’ve learned that leaders should focus on cultivating intrinsic motivation in their team members rather than relying on external motivators, such as deadlines and threats of dismissal. Intrinsic motivation is self-driven and self-perpetuating. Employees committed to their work because it aligns with their values are more engaged and produce higher-quality work. Building strong relationships is also crucial to creating a positive work environment. For our teams at Better Together, this means building relationships with potential partners and investing in relationships with team members. Managers should encourage their team members to build relationships with each other and foster a sense of camaraderie and collaboration within the team. By building a culture of trust and support, team members are more likely to be engaged, productive, and committed to the agency’s success.

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?

We must have made tangible strides in using communications to achieve equity, evidenced by concrete changes in the communities or sectors we work with. Culturally, I envision ensuring Better Together is an agency that embodies openness, inclusivity and creativity, distinctly different from my past experiences at other agencies. This should be reflected in our team’s morale and retention rates. Professionally, sustainable growth is essential, not just financially, but in our capabilities, reach and influence in equity-focused communications. On a personal level, continuous learning and staying true to my values are paramount. I also want to be known as a change-maker in the industry who is striving to make the world a better place in everything she does. Achieving these goals would mean we’ve not only stayed true to our mission but have also fostered a positive agency culture, making a real difference in the world.

Looking back over the last two years, what key accomplishments make you satisfied with your progress?

Reflecting on the first year of Better Together, the journey from a challenging situation at a previous agency to launching this new venture with the support of a VC firm has been both exhilarating and fulfilling. Despite the short time frame, the progress we’ve made is significant. The launch itself, a direct response to past adversities, stands as a testament to resilience and the power of positive transformation. Our focus on using communications to drive societal change has already begun to show promise. We’ve initiated impactful campaigns around biases in technology, breast health equity, the need for reparations for Black Americans, rebuilding Black Portland and so much more. We are laying the groundwork for what will be a lasting influence in the industry. Partnering with a VC firm not only provided the necessary resources but also affirmed the potential of our mission-driven approach. This first year has been about setting a strong foundation, one that is built on the lessons from the past and the aspirations for a better future. The sense of accomplishment in turning a challenging situation into an opportunity for growth and impact is immense.

As someone with significant influence, what’s the one change you’d like to inspire that would benefit the most people?

The one change I am deeply committed to inspiring is increasing diversity in senior roles within public relations agencies. In the U.S., a study by the Diversity Action Alliance found that among PR organizations polled, only 21 percent of employees are ethnically diverse, and among CEOs and top directors, that percentage drops to 7 percent. Achieving greater diversity at the leadership level can have a profound impact on the industry, as a whole, leading to more inclusive and effective communication strategies that better reflect the diverse society we serve.

There’s a noticeable gap in representation at the senior level in many PR agencies. By advocating for and actively working toward diversifying leadership, we can bring a variety of perspectives and experiences to the decision-making table. This change is not just about fairness or representation; it’s about enhancing the quality and relevance of our work. Diverse leadership leads to more creative solutions, broader understanding of different markets and more effective communication strategies.

This shift toward greater diversity in senior roles can also serve as an inspiration and a pathway for aspiring professionals from underrepresented backgrounds, showing them that there are opportunities for growth and leadership in the PR industry and at agencies.

How can our readers keep up with your work?

Readers can stay in touch by visiting my website at as well as connecting via LinkedIn at or

Thank you so much for joining us! We wish you only success.

About the Interviewer: Chad Silverstein is an accomplished entrepreneur and visionary leader. He started his first company, Choice Recovery, Inc., while attending Ohio State University and grew it to become an industry outlier before selling the business after 25 successful years. With the launch of his second venture, [re]start, a career development platform, Chad aimed to help people find meaningful career opportunities. Under his leadership, his team was recognized as a “Top Workplace” award winner for over a decade, twice being ranked the #1 small and medium-sized business to work for in Central Ohio. Chad sold [re]start in 2023, enabling him to focus on building an online community of high-performing leaders and continuing to make a positive impact in people’s lives.

Catharine Montgomery Of Better Together 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.