From time to time, we tap into the expertise of our InsideTrack team and ask them to share insights on a student support topic they’re passionate about. This week, we turn our blog over to Student Success Specialist and Coach Jenise Jester to share her insights into the student enrollment process, drawing on her experience coaching thousands of learners over the past eight years.

What are students really thinking about in the enrollment process?

Behind every headline about FAFSA delays, shifting admissions policies, or the looming “enrollment cliff,” there’s a real student wondering how, or if, college will fit into their life. Many are worried about being able to pay an application fee or whether financial aid will come through in time. Others wonder if they’ll fit in once they get to campus, or if their chosen program will truly lead to a better job. 

What I’ve learned through coaching is that these are often the questions that matter most to students — not just the big-picture policy issues, but the everyday barriers that shape each student’s decision. Enrollment Coaching helps translate those concerns into action, giving students the support they need to move forward with clarity and helping institutions see, in real time, what it takes to help every learner start strong.

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Five purposeful and practical coaching tips to support student enrollment

1. Build trust

We talk about “trust” a lot in higher education, and for good reason: it’s the door that must first be opened before a student decides to commit to an institution. Listening with intent, asking informed questions, validating challenges and following up are all integral parts of showing understanding, respect and conscientiousness towards learners — all of which ultimately earns trust.

There are many ways to approach this, but my favorite question to ask is, “What would make you feel the most supported during the first few weeks of your new program?” Based on the answer they provide, support them the best that you can. I also like to set the stage for them and say, “Imagine it’s week one. Things are not going as you planned. What do you need to hear in that moment to remind yourself to remain calm and stay engaged?” 

Then, if you check in on them in week one and things are not going well, you can remind them that, together, you’ve prepared for this — and as their coach, you’re with them and ready to help figure out the next steps. Predictable, personalized communication reinforces that your care as their coach doesn’t end once they apply.

Coaches who approach each interaction with consistency and curiosity can model the safety and stability their students hope to find in their academic journey. Think of all the ways a student is hoping to find trust in the university — from academic advisors suggesting classes, financial aid counselors creating a payment plan, and an enrollment coach saying they’ll be a support person. I try to remind myself daily that trust is the framework that holds a vast portion of the student experience together. 

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2. Ask the hard questions — with care

Building the foundation for a trusting relationship allows coaches to use transparency and earn the right to ask some tough questions of their learners. It’s important to normalize the fact that there will be challenges in their education, just as there are in all aspects of life. I do this in a few ways, but chief among them is the straightforward “ask permission” method. This sounds like, “I hear what you’re saying, and I also want to ask a question that could feel a bit direct…would it be okay if I push on this a little?” 

With this language, you not only get permission to push them out of their comfort zone in a safe environment, but you also give them a heads-up that this could feel a little uncomfortable. Once they respond to your question, thank them for being open and honest with you — even if their response is direct or challenging. 

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Tough questions during the enrollment process might look like:

 • “I know you mentioned concern around your finances. Do you want to share more about your financial situation? The reason I’m asking is to see if I can help you connect to financial aid resources that could help you as you apply to this program.” 
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• “You’ve mentioned before that you’ve wanted to finish your degree for a while – what’s different about now that makes you feel ready to move forward?” 
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• “When things get hard — and at some point, they usually do — what tends to make you consider walking away? I’m not asking because I think you will, but because if we can name those moments ahead of time, we can plan for them together.”

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These questions move both coach and learner beyond the basic logistics of transcripts, line items and transactions into the real factors that will influence a student’s ability to start a program and persist through to the end. Utilizing deeper questions, paired with empathy and transparency, helps students see possible future barriers and create a plan to avoid them. “It’s not about prying — it’s about preparing” is a phrase I use to align with a learner beyond the administrative and push into the individual aspects that will matter to their success. 

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3. Make your conversations personal

In coaching conversations, information-heavy, formulaic details are the quickest way to encourage someone to check out — especially if this is the first interaction they have with your institution. That's why it's critical to tailor your guidance, showing the learner you've really listened to their unique challenges during the enrollment process, which can often feel daunting or unfamiliar. 

A tool that can help you stay personal in your conversations, while keeping an eye on the big topics that influence enrollment and retention, is the Focus Wheel — a coaching tool with eight assessment areas for coaches to explore with students. 

Many of these categories become natural topics that weave in and out of your daily check-ins. Still, some topics, like a student’s personal health and wellness, may not be at the forefront of your typical to-do list, but might greatly impact their decision to enroll. 

Introducing a conversation can sound like, “The past couple of times we’ve checked in together, we’ve talked a lot about academics and your time management, but I wanted to swing into another area today and just ask about how you take care of yourself. School is a commitment! What are the things you do that help you stay mentally, physically and emotionally healthy so you can continue pursuing a successful experience with this program?” 

Taking the time to get to know a student’s habits can help give you reference points to guide later conversations. If you notice they’re not working out, or they’re feeling low, you have earned the trust to respectfully ask about these areas because you’ve made the effort to get to know that part of their life. That relational foundation with your students is what transforms an enrollment conversation that leans more toward a “to-do” list into a coaching partnership focused on their well-being. 

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4. Sustain motivation

Finding a learner’s “why” for enrolling in a program is a critical piece of long-term success. The “Five Whys” is a simple framework that asks people “Why?” five times to help uncover their deeper level of commitment. Remember that transparency is key to making this exercise feel authentic. You might introduce it like this: 

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‍“I’d like to do a quick exercise called the Five Whys. It starts with a simple “why” question, and then we ask four more times, each time going a little deeper. It’s not about me pushing or prying; it’s about helping you clarify the deeper motivations and values behind your decision to enroll. It might start as a surface-level conversation, but it can evolve into a poignant moment that captures what’s truly important to you. Do you mind if we try this?”

Coach: “Tell me why you chose this program.”
Learner: “I want a better job.” 
Coach: “Why is a better job important to you?”
Learner: “I want to do something I enjoy.” 
Coach: “Why is doing something you enjoy so important?” 
Learner: “Because I’m tired of feeling drained every day. I want to look forward to going to work.”
‍Coach: “I hear that! Why do you think it matters so much that you look forward to work?”
‍Learner: “Because it affects everything else in my life — how I show up for my family, my mood, my energy.” 
Coach: “That’s such an important insight. It sounds like this isn’t just about a better job, it’s about creating a life that gives you energy and allows you to show up for your loved ones the way you want, in a way that demonstrates your care for them. Why is that something worth pursuing?”
Learner: “Because I don’t want to just ‘get by’ anymore. I want to be proud of how I spend my days and to have enough energy left to enjoy the people I’m doing it all for. That’s how I measure success — by whether I can look at my life and feel proud of how I’m showing up.”

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You can see that, by the third or fourth “why?”, you start uncovering the layers that lead to core values and deeper motivations. 

As a coach, you also get a powerful moment to connect their actions to their goals. In this example scenario, a coach can end by asking, “It sounds like your motivation goes beyond just getting a better job — it’s about living in a way that reflects your values and makes you proud of who you’re becoming. How does that motivation connect to your decision to enroll in this program and the kind of future you’re working toward?” 

It’s no longer about a program or a job at that point; it’s about aligning actions with values. 

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5. Escalate pain points and cultivate institutional change

One of my favorite parts of coaching is the ability to influence change in an institution on behalf of students. Coaches don’t just solve individual problems; they identify and escalate systemic barriers that impact the quality of a student’s experience. 

As frontline supporters working with students every day, coaches are able to identify common themes and areas of inconvenience for students, then report those learners back to the institution. 

Through those experiences and efforts, things like simplified application fee waivers, enhanced support for international students, better registration communication, alternate hours for academic advising access, and other operational improvements have been made. This feedback loop with institutions creates important change and helps institutions see their own blind spots with messaging, processes, support services and more.

When you bring these elements together to support a student, you can help make barriers less overwhelming and help the learner gain trust in the organization’s support. The following is a story about a real learner’s experience and what our work together accomplished.

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Empowering students to enroll — and thrive 

Each coaching conversation has the potential to go beyond application fees, moments of doubt, and foggy vision — it can offer insight into the student experience and the institutional systems that shape all of those moments. When student supporters listen deeply and act on what they learn, we don’t just support the learner — we strengthen a school’s capacity to foster belonging, persistence, and success from day one. 

Dig deeper into the power of Enrollment Coaching by watching our webinar — Enrollment With Impact: Building Belonging and Lasting Student Success — featuring Wake Technical Community College, Penn State World Campus, and Jobs for the Future. 

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About Jenise Jester

Jenise Jester has worked in higher education since 2004, combining two decades of experience with a deep passion for helping learners navigate complex systems with confidence. She holds an MBA, an MA in Higher Education, and a College Counseling Certificate from UCLA. Jenise’s work centers on demystifying the education process — making the pathways to access, completion and success more transparent for students and the institutions that serve them.

Having lived in six states and three countries, Jenise brings a global perspective (and excellent packing skills) to everything she does. She now calls Utah home, where she lives with her husband, Chris — a retired Army veteran — and their two dogs, Tunder (Doorbell Monitor and Head of Security) and Millie (Snack Acquisitions Team). A voracious reader and lifelong learner, she’s currently channeling her curiosity toward learning ASL and planning her next big adventure abroad in 2026 — because exploring new places, ideas and stories is simply a must in life.