A Developmental Lyft: Car-Ride Conversations Fueled by Questions of Meaning and Depth

For over 20 years, I have served in various leadership capacities on college campuses. This has included student affairs, academic, and administrative roles. I began my career as a Resident Director and Coordinator of Student Life. Most recently I have served as an Assistant Teaching Professor and Academic Program Director. Yet, some of my most meaningful and developmental conversations with students occurred when I was “off the clock” from my salaried roles.

Between the Fall of 2016 through February of 2022 (the start of the pandemic) I drove as an independent contractor for both Uber and Lyft—the ridesharing companies. During this time, I provided 4,590 rides (with a 4.97-star rating) in Boston, MA and the neighboring communities. With 52 institutions of higher learning in the surrounding area, there are no shortages of students needing rides to class, home, internships, meals, nightlife venues, train stations, airports, or other locations for their adventures.

When I decided to drive for these rideshare platforms, I did not intend on creating holding environments for developmental conversations. From my own schooling in a student affairs graduate program, I had internalized that to engage students in the developmental process, I would need a long-term, in-depth, extensive, and robust relationship to move students from their authority-dependent current locale to self-authorship. How else would we be able to challenge and support students in synchronizing their beliefs, values, and interpersonal loyalties while chal­lenging them to see reality as complex?

When I decided to drive for these rideshare platforms, I did not intend on creating holding environments for developmental conversations.

Over time, it became evident that serving as a developmental educator was possible even with limited and brief touchpoints with students. This idea solidified when driving students to and fro. When in the car, I would typically have between 8-min and 40-min to provoke students in thinking big, digging deep, and engaging in meaning-making processes—what Marcia Baxter Magolda suggests as creating a learning partnership and being good company for the journey. These experiences re-framed for me that developmental conversations need not be elaborate, long, or pre-scheduled. For campus educators, in as short of a time to ride in an elevator or walk across campus, we can pose questions and instigate opportunities for students to purposefully pause and think reflectively—spurring a developmental opportunity.

A Car Ride as A Developmental Opportunity

Ridesharing platforms (e.g, Lyft and Uber) operate to link those in need of safe in-the-moment transportation with individuals who utilize their own vehicle to provide those transit needs. Riders will sign into their apps and indicate exactly where they want to go based on their exact pick-up location. Within moments, drivers are notified about the ride opportunity. If the ride is accepted, the two are matched. When the driver arrives at the indicated pick-up location, the ride begins—if the passenger(s) are riding with me, that is when a developmental learning partnership commences.

The Use of Strategic Questions

In most rides, pleasantries and check-in questions—like, how is your day going?—is an opportunity to assess their general mood, vibe, and welcomeness for engagement. Once this connection is made, I begin by gently posing questions that are designed to support and challenge students in purposefully pausing and processing their lived experience through reflection and dialogue. Strategically asking questions is an important practice for developmental educators. We know that learning occurs when the opportunity to wrestle with meaning-making opportunities are presented. Questions powerfully provoke this kind of wrestling. When we pose questions of meaning and depth, we allow students to be seen and valued for their wisdom, knowledge, insight, and expertise.

We know that learning occurs when the opportunity to wrestle with meaning-making opportunities are presented. Questions powerfully provoke this kind of wrestling.

So often, in our classroom and co-curricular experiences, students serve as information-dump repositories. This is what Paulo Freire considered a banking approach to learning. When educators lean into this lecture-style approach to learning, we are the ones who are constructing the meaning and then attempting to impart it to the minds of our students. The subliminal expectation is for them to internalize our meaning and replicate it in their experiences.

Freire's explanation of the banking approach to learning details that students are treated as repositories of information to whom educators make deposits. Carol Mullen builds upon this to suggest that when engaging students in this way, we are not only severely limiting the mutual construction of meaning, we per­petuate oppressive, degrading, and dehumanizing actions. Campus educators need to be mindful of banking practices because of the struc­tural and mechanical aspects of traditional educational practices that naturally establish and provoke deposits. Namely, when we solely lecture at students—we are making limiting deposits.

Questions offer an alternative to passivity. When we strategically offer questions, we can invite a space for students to purposefully pause, process reflections, make meaning, and offer responses to spur dialogue. Students who wrestle with these questions are then provoked to make moves in their developmental journey towards self-authorship. With these types of questions, students are stretching their internal capacity to define their beliefs, identity, and experiences.

How, When, and Where to Utilize Strategic Questions

The how of asking strategic questions is about reframing our statements into questions. I can recall in both academic and co-curricular contexts, plenty of situations when student learning could have been better engaged if statements would have been reframed as questions. For example, during student leadership trainings (e.g., Resident Assistant, Orientation Leader, Club Officer, etc.), rather than detail the laundry list of policies, strategic questions can be infused into the trainings that enable students to explore the rationale for policies and potential responses to policy infractions. Sample questions might include, “why do you believe our institution includes this policy in the handbook?,” “If we didn’t enforce this policy, what might be the implications?,” or “what do you believe are the most promising ways to respond to this policy infraction?.”

Campus supervisors can implement strategic questions into their managerial practice by shifting away from solely dictating about poor performance to asking questions of student employees. Sample questions might include, “how you believe you are performing?,” “how might your performance improve in the coming weeks?,” “what are the implications for this poor performance,” or “if you were in my position, how would you respond to this poor performance?.”

Faculty can fill their classes with robust dialogue by asking strategic questions—rather than solely providing lecture-style information dumps. Sample questions might include, “what was an ah-ha moment or important reflection from the literature?,” “how do you see something from our reading apply to life beyond our classroom bubble?,” “how might you apply your learning from this class to your practice?.”

Of course, providing details on our institutional policies, work performance, and course material is critical. And, before getting to our detailing of it, we can strategically invite questions that enable students to internalize the message and make meaning. This will strengthen their opportunity for learning and enhance the potential for then to apply that learning to practice.

The when and where of strategic question asking has limited bounds. We can pose questions in formal settings—a training, supervisory conversation, or class—as well as informally. Informally, we can leverage our positional power and authority as campus administrators and faculty to engage students in healthy reflection and dialogue as we are walking through the quad from one engagement to another, in the cafeteria line, or in an elevator. These can be facilitated in one-to-one contexts as well as engaging a group of students with our strategic questions.

If we are dedicated to robust student learning and development, we need to cultivate a healthy habit of asking strategic questions when and where our paths cross with students. We need to nurture the courage to interrupt our information-sharing delivery of content and leverage the power of questions to be good company for students and live into a learning partnership with them.

If we are dedicated to robust student learning and development, we need to cultivate a healthy habit of asking strategic questions when and where our paths cross with students.

What Kinds of Questions to Use?

Ken Nelson and his colleagues in the book Designing and Leading Life-Changing Workshops: Creating the Conditions for Transformation in Your Groups, Trainings, and Retreats suggests we can pose these questions of meaning and depth in five directions: future, past, purpose, founda­tion, and present.

Future questions are employed to imagine possibili­ties, set trajectories, and inspire action.

Conclusion

Based on my experience as a rideshare driver, I firmly believe that even in time-and-touchpoint-limited interactions with students, we can create meaningful purposeful pauses that advance their developmental journey toward self-authorship. These kinds of powerful, developmental experiences can be initiated spur of the moment. They need not be elaborate, long, or pre-scheduled enterprises. Even as a stranger with limited time, the strategic use of questions can serve as an important tactic to engage students in meaningful reflective practice. This technique can encourage deep, critical thinking about important themes in their lives.

Based on my experience as a rideshare driver, I firmly believe that even in time-and-touchpoint limited interactions with students, we can create meaningful purposeful pauses that advance their developmental journey towards self-authorship.