Authentic learning has always required a connection to a real context. However, in a generative age, where AI cannot “read the room,” contextual thinking has become more important than ever. In this article and podcast episode, I explore the implications of this and share six practical ways we can integrate contextual thinking into our daily practice as educators.

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A Snapshot of Contextual Thinking

My friend Ana is a middle school science teacher who had her students do a mini-project where they researched eco-friendly solutions to reduce human environmental impact. Then they created short PSA videos. 

Last year, she noticed a disturbing trend. All of their initial solutions and big ideas seemed generic and vague. Many of their scripts were verbose and used the familiar “it’s not this, it’s that” structure indicative of AI. It was chock full of advanced vocabulary words. The end result was something impressive but artificial. It lacked the casual phrasing of her seventh grade students. 

“It felt kind of depressing. Like I know that my seventh graders aren’t going to create PSAs that will end up in a national media campaign. But I always loved hearing their voices. But this felt dull.”

She nagging feeling that they had outsourced most of their thinking (and their creative process) to generative AI. So, she made some big changes. She connected the project to local ecological challenges and brought in a guest speaker that they could interview. She had them story-board their PSAs by hand and type out the scripts in Google Docs with time stamps. 

It took a little more prep work but it ultimately paid off. The students created work that was more thoughtful and creative. They seemed more engaged. In other words, it was more authentic. 

The difference here was context. And it turns out contextual thinking is one of the critical skills students will need to develop in an age of generative AI. 

 

The Need for Contextual Thinking in a Generative Age

At its core, AI struggles with contextual understanding. Every chatbot is a prediction machine using algorithms trained on massive amounts of data. But AI doesn’t know what’s going on. It’s not self-aware. Which is a good thing. Otherwise we’d have Skynet and Blade Runner and every other dark dystopian nightmare from science fiction. 

AI can’t “read the room.” It’s really good at generating solid general response. It can explain solutions to common problems. But it tends to be vanilla in its approach:

I recently wrote about how we can create AI-resistant writing. Context is a huge part of what will make student writing stand out in creative work. Similarly, in problem-solving, contextual thinking helps students learn how to solve the types of problems they’ll actually solve in life. These are often called “wicked problems,” where the solution leads to new challenges and trade-offs.

Contextual thinking requires noticing the particular details of a specific situation. It pulls students into a space where they wrestle with the nuances and tradeoffs of a solution. Context pushes students to understand constraints that are distinctly local. This leads to divergent thinking. At times, they engage in systems thinking and empathy with an authentic audience. 

But how do we actually make this a reality? I want to share a few ideas. 

 

Six Ways to Incorporate Contextual Thinking in Our Classrooms

The following are six key areas where we can integrate contextual thinking into our daily practice as educators. This isn’t a comprehensive list. You’ll likely have some of your own ideas that have worked for you. 

 

1. Focus on Authentic Context in Problem-Solving

When I taught middle school math, my students struggled with a specific word problem on a district benchmark standardized test. Students underperformed despite the fact that they had aced more challenging problems. I was baffled because this should have been super easy.

The problem essentially said, “You are a catcher throwing a runner out at second base. Using the Pythagorean Theorem determine the distance between home plate and second base by looking at the dimensions of the diagram below.” 

This was a simple problem and at first I assumed that students didn’t know what home, first, second, and third base were because they weren’t labeled. But as we reviewed the problem afterward, that wasn’t the issue at all. 

Instead, it was a problem of what Dan Meyer refers to as pseudo-context. This what happens when we ask students to apply certain math skills and concepts in a way that doesn’t reflect how we use math in life. No catcher would use the Pythagorean Theorem in this situation. I can’t imagine Cal Raleigh seeing a runner take off toward second and asking, “What would Pythagorus do?” 

At this point, I decided to rewrite the problem and integrate it into our new unit on statistical analysis. This time, I changed the context. I can’t remember it entirely but here is a basic idea:

Maryvale High School just one our first baseball state championship in decades. You are the custodian who also manages the field. You’re so excited because your son was on that championship team your senior year. But this morning, you received an email informing you that members of the other team are claiming that the bases were moved to make it easier for your team to steal and harder for their catcher to throw the runners out. You can’t measure the distance from home plate to second base because of the mound but it might be possible to prove it mathematically given the dimensions of the field that we just measured.

I also included statistics from the game, the players, the average stolen bases for the team, etc. So they had the bonus option of using statistics to make their point. 

It’s the same essential problem but the context is different. My students actually enjoyed this second problem. Part of it was the fact that I actually didn’t tell them to use the Pythagorean Theorem. They had to remember something they’d learned and apply it. But another part of it was the context. This problem felt like the way that people actually use math in real life. It was connected to something suspenseful and high stakes. 

Honestly, there are so many better contexts for the Pythagorean Theorem. Most of them would connect to design and construction; which would be awesome!

So as we think about how students solve problems in both math and science, we can intentional about tying the problem to an authentic context. This often increases engagement but also makes it more memorable. The context becomes the hook for students to access when they engage in retrieval practice. 

 

2. Add Contextual Elements to Research 

As students engage in research, they will need to pay attention to the context of the information. Where is it coming from? Who is the intended audience? What emotions does the information try to illicit. This is part of why I love using the forensic approach developed by Jennifer LaGarde and Darren Hudgins. They use the metaphor of a digital detective to describe this mindset.

The Triggers Lens: Digital Detectives use this lens to make sense out of the ways information elicit an emotional response.

The Access Lens: Digital Detectives use this lens to see how platforms and devices determine what is a credible source. For example, a news story looks different on a mobile device than on a browser. It’s also a chance to think about how the community impacts interpretations of information. So, the way people on Twitter and Facebook interact with a news story will vary.

The Forensics Lens: This is the lens that we tend to think of as information literacy. Here is where students investigate the information from a place of curiosity.

The Motives Lens: This is where students think about the motives of those who are creating the information. Like any great detective, they consider why people might manipulate information. Notice how this approach goes beyond simply analyzing information accuracy and takes into consideration the context of the information as well. 

But we can also incorporate contextual thinking into the types of research students engage in. At a younger age, students might do observational research in short field trips where they find aspects of learning in their surroundings. For example, in learning about 3D shapes, they can find specific examples in a scavenger hunt. In a design challenge where they have to design an inclusive playground, they might do observational research of how people use the playground. 

At all ages, students can interview guest speakers who have firsthand knowledge about their content. This is especially true of something like an oral history project. They can do surveys. It can be as simple as tally marks in early elementary and all the way up to a larger needs assessment survey in middle school and high school. 

As students move into high school, contextual research might involve analyzing distinct local data and engaging in problem-solving based on their insights. It might include connecting with a local archivist who can provide primary and secondary source documents in history or geography. 

 

3. Require Deeper Context in Writing  

In a recent blog post, I described how we can design our writing prompts to be AI-resistant. One of the core ideas is to incorporate contextual thinking into the prompts themselves. So, instead of saying, “How does a bill become a law?” with middle school students, you might take it to a deeper level and focus on local context.  

It might be something like, “Describe a law that would impact your community in a positive way. Include specific examples of how the issue plays out in your neighborhood and how it impacts your community. Then describe what would need to be done to pass a local, statewide, and federal law. How do these processes vary and what are the pros and cons of each approach?” 

However, this is just the starting place. We can integrate contextual thinking into the research phase of writing (my previous point) as well. You can also encourage them to pay close attention to a particular authentic audience when writing a draft and ultimately sharing their work. In the following video I share what happens when students share their work with an authentic audience:

When I taught middle school, I had three years where we also had community editors. These were local volunteers (many of them worked in writing-specific careers or they were retired teachers) and they each gave feedback on one piece of writing per week via Google Docs. 

 

4. Include Contextual Elements in Case Studies

I often default to theoretical case studies when I have students engage in problem-solving or discussions. However, this is a great opportunity to tie in contextual thinking. This might mean we find specific cases with a local context or we provide a case with a different context but ask students to examine contextual elements. We can also include reflection questions about why a strategy or idea fits a specific situation. Here are some guiding contextual questions they might answer:

• What is unique about this situation or place?
• Who are the stakeholders and what do they value?
• What constraints exist (time, resources, geography, culture)?
• What background information do we need to understand this situation?
• How might this situation look different in another location?
• What assumptions might people be making?
• What factors are influencing the decisions people make?
• What tradeoffs are involved in possible solutions?
• What information is missing that would help us understand the situation better?
• How might different groups view this situation differently?
• What local factors might affect whether a solution works?
• How might history influence what is happening now?
• What unintended consequences could occur in this specific context?
• How might this solution need to change for this setting?
• What details matter most in understanding this situation?

As they grow stronger in contextual understanding, we can have students generate examples instead of only analyzing provided ones. This helps them develop the habit of asking, “In what contexts do we see this play out?” In other words, “where would I use these skills?” Or “Where does this particular concept occur in life?” 

At a more advanced level, you can run simulations that require contextual thinking. So, instead of just doing a budgeting project in a high school economics class, students could do a budgeting simulation where they have a specific character and they make financial decisions given the real-world constraints and challenges that people face as they work engage in the budgeting process.

 

5. Integrate Design Challenges, Mini-Projects, and PBL

I recently had dinner with a group of former middle students. When I asked what it was like to have me as a student, they talked about the classroom community, the humor, the fact that I would apologize for mistakes. One of them described what it was like to come out to me as a middle schooler in a community that could be really judgmental. 

On a side note, I felt affirmed. I sometimes get really self-critical. I think about strategies I should have used, research I wish I had known, and modifications that would have made my lessons better. I also think about the moments when I yelled at a class or when I made a snap judgment that turned out to be incorrect. 

But then it shifted to projects they did as students. They talked about blogging and podcasts. They shared what it was like to do the service learning projects with the food bank and paint a mural after school. They mentioned the documentary we filmed where they told the story of globalization through the history of their neighborhood over the last forty years. 

I was struck by the fact that they had developed deeper contextual thinking through PBL. With PBL, students learn the content through the project rather than doing a culminating project to prove what they learned. And a key element is to apply the learning to a real-world context. 

One of the reasons I love design thinking is that it centers this PBL process on the authentic context. Students develop empathy as they learn how to “design with” rather than simply “design for.” 

Note that the community context can be present in every part of PBL (though it’s not a requirement for every phase). You might do an entry event during Look, Listen, and Learn, where you bring in a guest speaker or go on a field trip. During the research phase, you might tie in the previously mentioned needs assessments or interviews. 

As students brainstorm and design solutions (Navigate Ideas), they might do a check-in with their audience or even engage in the ideation process together with their intended audience. You might have a connection to local materials or local experts in specific prototyping as students work through the Create a Prototype phase. In Highlight and Fix, students can ask for feedback from community partners as well. 

 

6. Teach Students to Provide Context for Chatbots

Most of the previous examples have focused on AI-resistant approaches to contextual thinking. However, in life, students will often be integrating AI into their work. This is why they need to learn how to provide AI with necessary context ahead of time. 

This starts with prompt engineering. If we consider the FACTS Prompt Engineering process, you’ll notice that students have to slow down and think intentionally about how they are using generative AI:

But the core piece is actually the RAFT (Role, Audience, Format, Tone). Again, this is simply a modified version of a process designed by Project CRISS. The key difference is tone. We are asking the AI to understand the context of who you are, who it should be (in terms of its assigned role) and the intended audience of what you are answering, creating, etc. 

But we can also provide additional contextual information. Students might submit documents, samples, and other types of data to help the chatbot make sense out of the context. Again, AI will never be able to “read the room” but the algorithms can improve in their predictions when we share contextual information as a sort of narrowing force. 

In the end, when students learn how to think contextually, they master the content at a deeper level. However, they also develop both the skill and the habit of contextual thinking that they’ll need as they navigate a world dominated by generative AI.