Part 2: Learning Shouldn’t Feel Like a Liability

MLS executives are in a unique position because they are accountable to boards that may scrutinize their decisions quarterly, monthly, or even more frequently. They are expected to understand the technology, anticipate what is coming, manage risk, control costs, and have answers when their board asks questions. That is a lot of pressure to always appear certain when the reality is that no one can possibly keep up with every change happening in technology right now.

Move too quickly and you may scare your board. Move too slowly and you are accused of falling behind. Invest in something new and you have to defend the expense. Wait until it is proven and someone asks why you were not ahead of it. You are damned if you do and damned if you don’t.

Meanwhile, members still need support. Rules change. Regulations change. Lawsuits happen. Vendors change. Technology breaks. Boards turn over. Real estate agents are asking for help surviving a difficult market.

Then you attend a conference and hear that AI has already arrived, your governance model needs to change, your data strategy needs to change, and your technology infrastructure needs to change. All of those things may be true. Then you go home on Monday and someone cannot log in.

That is reality.

Now imagine sitting in a room full of your peers while everyone is talking about MCP servers, AI agents, or a new data architecture as though everyone already understands it. How comfortable are you raising your hand and saying, “Can we go back? I don’t actually understand what that means.”

Some people will. Others are going to write it down, Google it later, and do their best to figure it out on their own. Some may never get back to it because they have an organization to run.

That is where learning starts to feel like a liability.

For an experienced executive, admitting that you do not understand something can feel risky. You may worry that someone will interpret a foundational question as a lack of sophistication, a lack of preparation, or even a lack of leadership. When that happens, people do not stop needing to learn. They simply become less comfortable learning out loud.

We cannot simultaneously tell people they need to learn faster while creating environments where admitting they have something to learn feels risky.

Foundational Doesn’t Mean Unsophisticated

I do not think the answer is simply creating a “beginner” track either. There can be an implied judgment in asking someone to identify themselves as a beginner, particularly when that person is an experienced executive who is expected to lead an organization.

Someone can be an incredibly sophisticated MLS executive and still have a foundational understanding of AI architecture. Those things are not contradictory.

Maybe this education should be categorized as Foundational, Applied, and Technical. Foundational education helps me understand what something is and why it matters. Applied education helps me understand what it means for my organization and what decisions I should be making. Technical education is where we get into how it actually works.

That distinction does not rank the person. It describes the conversation.

An AE might attend a technical session on data licensing in the morning and a foundational workshop on MCP that afternoon. That is what learning actually looks like.

The people pushing the technological boundaries of this industry should not have to slow down. We need advanced conversations. We also need a way for everyone else to understand why those conversations matter and how they apply to their organizations.

The goal should be to make learning easier to enter at any level without attaching judgment to where someone starts.

We Have to Make It Safe to Say “I Don’t Know”

There should be absolutely no shame in an AE saying, “I understand what AI is at a high level, but I don’t understand MCP yet. Teach me why it matters to my MLS.”

That is exactly the question we should want them asking.

The ability to say “I don’t know” is not a weakness in leadership. In many cases, it is what allows better questions to follow. It creates room to understand the issue before making a decision, instead of pretending certainty because the environment makes uncertainty feel unsafe.

If we want executives to make thoughtful decisions about unfamiliar technology, they need places where curiosity is rewarded rather than interpreted as a deficiency.

Are We Applying the Same Standard to Ourselves?

This is where I think the conversation gets a little uncomfortable.

We spend a lot of time telling MLSs to challenge legacy thinking, question their processes, listen to their customers, and stop doing things a certain way simply because that is how they have always been done. Are we applying the same standard to ourselves?

I have not been in the industry workgroups, so I will not pretend to have firsthand experience with how effective they are. I do consistently hear from people who participate that some conversations feel repetitive and progress can feel slow. Maybe that is another place worth asking the same question we ask MLSs: Is the way we have always done this still producing what we need?

More broadly, we tell MLSs to listen to their customers. We should be asking them what they need from us too.

What do you not understand? What are you hearing repeatedly but still do not know how to apply? What decisions are you being asked to make that you do not feel equipped to make? What would help you have these conversations with your board? Most importantly, what do you actually need from us?

Those answers should influence our education, workshops, workgroups, and industry resources. Otherwise, we are getting dangerously close to doing what we criticize: deciding we know what people need without asking them.

Give People Somewhere Safe to Learn

I am actually hopeful about where we go from here. With Jessie Edgerton coming on board at CMLS, I believe there is an opportunity to build even more education around these conversations, including workshops where MLS leaders can go deeper at the level that is useful to them.

I would love to see environments where asking the foundational question is encouraged rather than embarrassing, and where someone can leave understanding not only what is changing, but what it means for their organization.

The goal is not to make every MLS executive an AI expert or software architect. It is to give them enough understanding to make good decisions for their organizations and enough confidence to ask better questions when they do not know.

Learning should not require someone to quietly protect their reputation while trying to fill in the gaps on their own. It should be part of the job, especially when the technology is changing this quickly.

Telling People to Catch Up Doesn’t Help Them Catch Up

It was not that long ago that MLSs were distributing listing information through printed books. Now we are asking those same organizations to understand APIs, cloud infrastructure, data licensing, interoperability, AI, large language models, governance, and emerging protocols that did not exist when many of today’s systems were designed.

Then we criticize the industry for being slow.

Some of that criticism is deserved. Legacy technology has stuck around too long. Vendors have not always moved fast enough either. There are organizations that need to change and decisions that probably should have been made years ago.

Still, telling people to catch up is not a strategy for helping them catch up.

Fear is not education. A great presentation can create awareness, but awareness without understanding does not necessarily create action.

If someone leaves a conference thinking, “We’re behind, everyone else understands this, and I don’t even know where to start,” urgency has not created action. It has created paralysis.

If learning feels like admitting a weakness, people are more likely to stay quiet than ask the question that might actually move them forward.

If we want MLSs to move, we have to help build the path.

Change Goes Both Ways

Of course MLSs need to evolve. Technology is moving incredibly fast, and pretending otherwise is not going to protect anyone from what comes next.

Vendors, workgroups, conference organizers, and the rest of us participating in this industry need to evolve too.

If we want hundreds of MLS organizations with dramatically different sizes, budgets, resources, and technical capabilities to evolve with technology, the way we educate them has to evolve too. The most technologically advanced organizations should not have to slow down, and everyone else should not be expected to magically catch up.

We need to build the bridge between the two.

That means teaching the why before jumping into the how. It means creating different levels of education without making anyone feel less sophisticated for choosing foundational learning. It means creating environments where an experienced executive can say, “I don’t know,” without worrying that someone will interpret that as an inability to lead. It also means asking MLSs what they need instead of continually deciding for them.

Most importantly, learning cannot feel like something that puts a leader’s credibility at risk.

If we want this industry to change, our job is not just to point toward the future. It is to make sure more people know how to get there.