The Questions I Didn't Know I Needed to Ask

The most important question in a technology decision may be the one you didn’t know you needed to ask.

The report wasn’t pulling the right information fast enough. It was budget season, and we needed analytics for projections.

Ten seconds. Thirty. Two minutes. Five.

“This isn’t working the way I thought it would,” I told the vendor.

“It’s not designed to work that way,” he replied.

“You didn’t tell me that,” I said.

“You didn’t ask,” he replied.

There are so many questions I wish I had asked when I started in this industry, especially about new technologies and how they would work in my environment.

Consider this a starting point for making smarter decisions in an era when technology evolves faster than your procurement cycle. For all the research you do, you still won’t know it all. And none of us wants to be held accountable for spending tens or hundreds of thousands of dollars on solutions that don’t do what we need them to do.

That is particularly true in the parking and mobility industry, which hosts professionals from a mishmash of backgrounds—public service, law enforcement, customer service, facilities, IT, or, in my case, the forest service.

No matter how we got here, we need the right insights to be effective: insight to ask the right questions, insight to recognize what we don’t know, and insight to know who to ask for help.

What problem does the technology solve?

I am captivated by technology.

Early in my career, I saw license plate recognition (LPR) as a way to modernize operations, reduce staff burdens, and improve the customer experience. I pursued LPR tenaciously before I got permission to implement it, and much of that enthusiasm came from tales of ever-improving accuracy, ease of installation, and all the other panaceas we’re promised when we’re on a trade show floor surrounded by demos and displays.

But the new hotness technology everyone talks about in the moment, whatever it may be, isn’t necessarily right for your needs—even if it seems like it will solve all your problems.

I've seen campuses adopt mobile payment platforms that confused their users and LPR systems installed without considering whether enforcement policies supported real-time compliance. A lack of preparation certainly contributed to those deployment problems, but so did a misunderstanding of the problem the technology was supposed to solve.

If you don’t define the Why?, then the So what? may lead to wasted time and money—or potentially even more time and money to correct an avoidable problem.

Ask:

• What’s our biggest bottleneck?
• Are we solving a staffing issue, a customer issue, or a policy issue?
• Will the technology fix the root cause, or just mask it?

People are often reluctant to ask that last question because technology is frequently seen and sold as the solution to a problem when it may only be part of the solution.

If you don’t understand the root cause of the problem, you can’t fix it. Enthusiasm for a particular solution can easily give you tunnel vision.

How will the "new hotness" work with everything else?

Parking is never one system. It’s a complex ecosystem of software, hardware, policies, processes, and people.

Permits, enforcement, gate systems, sensors, payments, customer service, payroll interfaces, and financial reconciliation may all need to work together.

Before implementation, ask:

• Who owns the integration process?
• Has this integration been implemented successfully elsewhere?
• Will we have a dedicated project manager?
• How will we test and verify that the systems communicate the way we expect?
• What is the process for agreeing that the technology is ready to go live?

Integration should never be a side note. It should be a primary planning conversation from day one.

What happens when the person who knows everything leaves?

Succession planning is one thing. Succession planning during the implementation of a new solution is another.

Parking directors don’t always consider this scenario because it seems unlikely—until it happens.

More than once, I’ve seen operations struggle when a key staff member—the person who “owned” permit sales, analytics, the appeals process, or maintenance of handheld devices—left unexpectedly. Documentation was sparse, training was minimal, and institutional knowledge walked out the door with them.

Ask:

• What training is available for new staff?
• Is there a knowledge base or written procedures?
• Do we have a plan to cross-train our team?
• How do we handle turnover or extended absences?

It’s easy to focus on launch and overlook longevity. Sustainable operations depend on shared knowledge, not just individual expertise.

Who else has done this, and what did they learn?

This is one of the most obvious and valuable questions you can ask, and one of the easiest to forget.

I still remember hearing someone ask what PARCS meant (Parking Access and Revenue Control System) during a presentation, followed by the grateful sighs of several other audience members.

No judgment. Just encouragement from others.

Be comfortable asking questions, even when you think you should already know the answer.

Talk to peers who have used the solution you’re considering, installed the same equipment, or tackled the same challenge. Ask vendors for references. Post questions to professional forums and listservs.

Ask:

• What worked well?
• What problems did you encounter that you hadn't planned for?
• What would you change if you could do it again?
• What hidden costs or delays surprised you?
• How did customers react?
• How was the change received?
• And sometimes: What does this acronym mean?

The parking industry is full of generous professionals. I’ve had open and candid conversations with peers who helped me avoid major missteps simply because I asked.

Your network can be one of your best insurance policies. And when greater independence is needed, there are professionals whose job is to research technologies and evaluate alternatives from a neutral perspective.

What does success look like?

A successful launch isn’t success.

It’s the beginning.

Success can mean happier customers, meaningful analytics, empowered front-office and enforcement staff, improved efficiencies, or any number of other outcomes.

Yet for every happy customer, you’ll still have an unhappy one. For every useful data point, you'll encounter anomalies. Sometimes the reasons will be obvious. Sometimes they won't.

Meaningful metrics matter. Subjective feedback adds color but doesn’t tell the entire story. A balance of qualitative and quantitative information is vital.

Ask:

• Does the solution make us more efficient?
• What key performance indicators should we track?
• How will we gather feedback from users?
• How will we know whether the problem we started with has actually improved?

Defining expectations before implementation makes it possible to evaluate outcomes more objectively and tell a much more compelling story about a program’s impact.

Who can challenge my thinking?

Having someone say, “Have you considered this?” or “That might work differently than you expect” matters.

Whether it’s a colleague, mentor, vendor who understands your environment, or outside consultant, you need someone who isn't afraid to tell you your idea is great.

Or that it sucks.

Ideally, that person doesn't have the same investment in your idea that you do, but understands the situation well enough to be candid. They should suggest more questions to ask and, potentially, snap you out of your tunnel vision, or at least get you more grounded.

Ask:

• Who can I trust to be candid with me?
• Who understands how I think?
• Who can offer an outside perspective without being invested in a particular answer?

Sometimes the person who challenges your idea is providing more value than the person who agrees with it.

What assumptions am I making?

Parking and mobility professionals are problem-solvers by nature.

We’re used to constraints—budget, space, staffing, politics—and we build workarounds.

But sometimes those workarounds become assumptions that limit our thinking.

Ask:

• What am I taking for granted?
• What hasn’t been tested?
• Is there another way to frame the problem?
• What would have to be true for my assumption to be wrong?

Challenging assumptions can reveal opportunities and help ensure a solution actually works.

For example, assuming people will resist the changes brought by a new technology doesn't mean they won't eventually accept them, particularly when given time and transparency about the benefits.

Cashless parking operations provide a useful example. There is certainly merit to the argument that multiple payment options serve the greatest number of users. But there are also plenty of organizations that successfully transitioned to cashless operations despite assumptions that customers would never accept the change.

The assumption deserved examination rather than acceptance as fact.

What story are we telling?

Every decision tells a story.

Is the organization viewed as punitive or protective? Flexible or rigid? Forward-thinking or out of touch?

Policies, tools, and new technologies all help shape an organization’s narrative to its customers.

Ask:

• How does this solution affect the visitor, employee, student, or permit holder?
• Are we transparent about why we're making the change?
• Are we providing more choices or more restrictions?
• When combined with our existing systems, does the new solution make it easier or harder to use our services?

The answer to that last question may seem obvious. Asking it anyway matters.

A new solution can improve employee efficiency while making life considerably more difficult for customers. If it does, the operational improvement may be more trouble than it is literally worth.

The questions change

Technology isn't slowing down.

From smart sensors and reservation platforms to artificial intelligence and increasingly automated enforcement tools, parking and transportation operates in a dynamic environment that requires constant learning.

Don't do it alone.

Stay curious. Build relationships. Lean on your network. Engage with people who challenge your thinking and make you better.

The questions I know to ask today aren't the same ones I knew to ask when I started my career.

I hope that remains true ten years from now.

Because perhaps the goal isn't to reach a point where we finally know all the answers. It's to remain curious enough to recognize that there will always be questions we haven't thought to ask.

Above all, ask questions so the answers don't surprise you.

The question I'm left with

What aren't we asking?

A version of this article appeared in the July 2025 issue of Parking and Mobility magazine.