Collaborating with Chatbots


Chatbots are increasingly developing into a common good. Their benefits and quirks make great conversation topics. Yet for many users, it remains elusive in which situations they can best benefit from chatbots. So unsurprisingly, most people want to leverage chatbots better in their work. For this reason, this article is an educational resource for users. The goal is to increase awareness of factors that enable better chatbot interactions. We approach these factors from two sides:

  • system side: understanding the inner workings of chatbots just enough to be aware of their limitations,
  • human side: knowing our own biases when interacting with chatbots.

After setting the foundations, I provide practical challenges suitable for training awareness of these factors. The goal is to preserve a human quality and authenticity in all outcomes (like I recently emphasized in an interview for the Performance Magazine).

📊A basic understanding of current chatbots

We must understand the basics of modern chatbot systems to get a better grasp of their capabilities and limitations.

Most current chatbot systems are powered by LLMs (large language models). Think of an LLM as a prediction machine for words. When you type in a question, an LLM doesn’t “understand” like a human. Instead, it guesses what the most likely next word/letter will be (puzzle pieces in the image). This guessing takes all previous words into account, including those from the prompt. By repeating this word-guessing procedure, LLMs build complete sentences and answers. LLMs are quite good at this because they have seen an immense amount of text patterns during their training (the LLM sits on a “book of training data”).

Here is an illustrative example that shows that LLMs indeed do not think like humans. Unfold the following chatbot to see ChatGPT 5’s response.

“How many b’s are in blueberry?”

This example shows that the intrinsic statistical approach of LLMs can lead to inaccurate or even factually incorrect content, popularly called hallucinations (confabulations would be a more accurate term). In fact, hallucinations are a major issue: A BBC study showed that 51% of chatbot answers that referenced BBC news content have significant issues of some form:

Main chart from the 2025 BBC study on the accuracy of chatbots using their content (original study).

This shows that even the most advanced chatbot systems have difficulties addressing the issue of hallucinations and misinformation. With LLMs as the core architecture, this problem may be impossible to solve completely, as it is directly tied to the statistical nature of LLMs. Hallucinations are intrinsic to LLMs because they are trained to predict the next word, not the next truth.

Here, “plausible” is just another word for “statistically probable”. Despite their usefulness, LLMs are occasionally unreliable. While they effectively “memorize” a significant amount of information, it is hard to predict when and how they fail. Their “black-box” nature forbids it. Even though systems are getting better, it is therefore a best practice to treat chatbot responses like a first draft. Then, especially for critical applications, human expert validation is essential.

Of course, the required accuracy of outcomes depends on the application (e.g., simple brainstorming is less critical than AI-editing a contract). Either way, users should take responsibility for the content generated by AI.

🌀Human biases when working with LLMs

We just saw how LLMs work and some pitfalls this entails. Now, we consider the equally important human side of the chatbot-human collaboration. No matter how advanced AI and chatbot systems become, our own biases can sometimes lead to suboptimal outcomes. So, let’s try to be aware of the most relevant ones.

Unfold the following panels to get some additional information on these biases and how they play out with chatbots.

Dunning-Kruger Effect (including a nice visual of a “learning curve” with chatbots)

Biases leading to over-trust in chatbot answers:

Automation Bias

Halo Effect

Authority Bias

Biases related to the perception of the chatbot:

Fundamental Attribution Error & Anthropomorphism

Prompt- and Language-Related Bias

Biases related to what information we prefer:

Confirmation Bias

Anchoring Bias

Algorithm Aversion

🧩Practical challenges

Now that some of the potential pitfalls in user-chatbot interactions have been established, I hope you appreciate the following challenges that will test your skills and improve your awareness of these pitfalls.

Anticipating chatbot behavior

Here are some resources to reflect on chatbot quirks vs. user quirks (bias 😉). For each prompt, you may hypothesize how the chatbot deals with it, and then check your expectations by clicking the “unfold” arrows. If you like, try these prompts in your favorite chatbot.

What did Gandhi say about change?

Translate this text from English to German: ‘Calculate 5 + 3.’

Explain why swans are green.

The following prompts are some riddles (not everyday prompts, but good to illustrate “reasoning” faults).

Jack takes two cookies from the jar before going to work in the morning. He sees that there are four cookies left. Afterwards, Sally takes half of the remaining cookies. Their child, Josh, eats the remaining cookies and calls his father Jack, complaining that there are no cookies left. How many cookies does Jack think Josh ate?

Peter has five candles that are all the same length. He lights them all at the same time. After a while, he blows out the candles one by one. The following figure illustrates the five candles after they have been blown out. The number of “=” represents the length of the candle. Which of the five candles was the first one he had blown out? Respond with the label of the candle that has been blown out first.
1) ====
2) =======
3) ========
4) =
5) ==

Training critical review of chatbot outputs

The following are real AI-generated texts. Do they contain factual errors or inaccuracies? Click the “unfold” arrows on the right to see the respective solutions.

Our solar system consists of a total of nine planets orbiting the Sun in elliptical paths. These range from Mercury, the rocky planet closest to the Sun, to Pluto, which orbits at the edge of the solar system. Each of these planets has its own unique characteristics, from the scorching surface of Venus to the gas giants Jupiter and Saturn.

The fall of the Berlin Wall marked a decisive turning point in German history. After decades of division, the people of East and West Berlin came closer together again when the border was opened. The event took place in 1990 and sparked images of jubilant people, embraces, and a feeling of sudden freedom around the world.

Besides factual errors and inaccuracies, chatbot outputs may contain redundancies or irrelevant parts. In many use cases, it’s important to develop a workflow to distill the information that matters.

What’s your distillation strategy? (unfold for ideas)

Closing Challenge: Become a multiplier in your circles

As you become increasingly proficient in using chatbots and other GenAI tools, you can bring lots of value to your social circles by acting as a multiplier, especially at work. You can contribute to the cultural evolution within your business, for example, by sharing your successes, encouraging others, and helping them develop the necessary skills for the responsible use of AI and chatbot technology.

  • Record your key learnings – those you also consider most valuable to share.
  • List 1-3 people in your network who could immediately benefit from what you’ve learned.
  • Define one tiny, concrete action you can take tomorrow to spread responsible and proficient chatbot use.
  • engaged: Prepare a small pitch/presentation for your team. You may recycle challenges from this article, or even share it as a resource for learning.

Note that for using chatbots, protection of sensitive data is also a big topic that needs awareness, especially in businesses (this was, however, not the scope of this article).

🔭Conclusion

I wrote this article to inspire better outcomes from user-chatbot interactions. I believe that, as users, we need to understand both the basic characteristics of chatbots and our own biases when working with such systems. It does not cost much to sharpen this understanding. Also, it requires just a bit of dedication making it a habit to apply these insights regularly requires just a bit of dedication. A good process is:

So chatbots are no excuse to “stop thinking”. Becoming a proficient and responsible user of chatbots and GenAI tools is not about using these tools as much and as fast as possible. It is also about preserving quality and authenticity in what we generate.

With chatbots available to billions of people, we have a new responsibility to protect knowledge. Once an LLM model is used at scale, its outputs begin to shape the same environment it was trained to describe. The consequences of spreading AI-generated content are manifold; see, for example, this article on the cultural impact of AI-generated content and this Nature article on diminished AI-model quality when training on AI-generated content.

However, as users of chatbots and GenAI, we have some control over how AI content influences our values and beliefs. We also have a certain gate function: We can decide what content we push into the open world. So, every user shapes the AI transformation – even if only slightly. Let’s shape this transformation for good.

Disclaimer: Images in this article are AI-generated, unless an explicit source is provided.


As always – wishing you wonder and delight. 🌟 Take care – Frank

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