We caught up with the brilliant and insightful Margaret Rothe a few weeks ago and have shared our conversation below.
Margaret, thanks for taking the time to share your stories with us today The first dollar your firm earns is always special. We’d love to hear about how you got your first client that wasn’t a friend or family.
Before becoming a managing partner at CounselMore Educational Services Management Software, I ran my own private educational consulting practice, Highergrounding.com. That’s where I learned how to truly connect with clients, understand their needs, and build trust. When I first transitioned from my 20-plus-year career in university student affairs to private consulting, finding my first client wasn’t easy—I had to put myself out there bravely and unapologetically.
You might call it Gorilla Marketing, but for me, it was about showing potential clients that I had a valuable service to offer. I took all the college memorabilia I had collected over the years, stapled my business cards to each piece, and went to local high school college nights. As the parents and students exited the events with their minds full of questions, I handed them my materials—I was available to answer the questions! I wasn’t just marketing—I was demonstrating that I was earnest, committed, and capable of getting the job done.
Any business transaction is ultimately a relationship. It starts with addressing basic needs—in this case, the parents’ need to trust someone who knows about college. You need to show that you understand your clients’ needs and are ready to meet them. That’s how I filled my client list, and that’s the approach we’ve embedded into CounselMore, a tool designed to meet the true needs of educational consultants.
As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?
I began my private college counseling practice after years in university student affairs, where I developed a passion for guiding students through key transitions. I then launched Highergrounding.com, where I directly supported families in navigating the complex college admissions process.
Awakening to the realization there were no streamlined tools to manage all aspects of educational services, I became a founding partner of CounselMore Educational Services Management Software in 2016. CounselMore is a tool that simplifies college counseling by automating administrative tasks, offering a full admissions database, and allowing counselors to focus on truly advocating for students and families.
What sets CounselMore apart is how it creates more time for meaningful interactions with students by eliminating repetitive tasks. I’m proud to watch the measurable difference it makes in counselors’ work-life.
Alright – let’s talk about marketing or sales – do you have any fun stories about a risk you’ve taken or something else exciting on the sales and marketing side?
There was a particularly large client we were pursuing, and we conducted a demonstration of CounselMore for their team. Unfortunately, the presentation fell flat. The feedback, or lack of it, suggested that the stakeholders weren’t interested, and soon after, we found out they had chosen our competitor.
We were disappointed because this client would have allowed us to invest more in the aesthetic aspects of our software—something we had prioritized less while focusing heavily on functionality and workflow efficiency. Our focus has always been on reducing clicks, optimizing the college counseling process, and making sure the software serves the end user, even if that means it’s not as visually polished.
Several months later, I received an email from someone who had been on that original call, asking if CounselMore had an implied workflow… That question showed me they hadn’t fully absorbed the importance of the methodology behind our system in the first demo. So, I sent a personalized video explaining the internal workflow. The result? They left our competitor, despite already being under contract, and came back to us.
Now, not only is this large client using CounselMore, but we’ve also begun doing private development for them. This experience reinforced that while flashy aesthetics can be appealing, what truly matters to our users is a system that flows, saves time, and solves real problems. And that’s what sets CounselMore apart—its embedded, thoughtful methodology. Our mission is always to empower college counselors to serve more students effectively.
Any advice for managing a team?
At CounselMore, we prioritize trust, flexibility, and open communication. Our approach to managing the team includes unlimited personal time off, without strict definitions of what “personal time” means. We measure performance by the work completed, not by hours clocked. This flexibility encourages mutual respect and a shared commitment to our goals.
When we hire, it’s less about a traditional interview and more of a working interview. New employees are brought in temporarily, paid for their training, and evaluated based on their fit within our team culture. We look for people who can handle ambiguity, communicate clearly, and understand the interdependence of the team.
To maintain high morale, we have a 20-minute meditation break at 2:00 p.m. each day. It’s a chance for everyone, who works remotely, to take a walk or decompress. This, along with an emphasis on honesty and enthusiasm about our mission, helps maintain a strong sense of community and support.
We work in 7-day sprints, which gives everyone the flexibility to manage their workload while still being accountable. Stand-up meetings ensure concise updates and clear communication. This structure allows us to stay connected and aligned while giving people the space they need to balance their lives.
We have a simple rule: be at stand-up meetings on time and respect each other’s workload. While there’s flexibility in when work gets done, there’s a clear expectation that everyone supports each other. This system has created a supportive and motivated team, and I’m really proud of the environment we’ve built.
Contact Info:
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