How AI Has Changed Everything: ClearPoint Strategy Founders Series
Co-Founder & Code Geek

Dylan is a Co-Founder and Managing Partner of ClearPoint Strategy and spends his time either in the clouds or in the weeds.

Dylan Miyake is the co-founder of ClearPoint Strategy, a B2B SaaS platform that empowers organizations to execute strategic plans with precision. A Bowdoin College and MIT Sloan alumnus, he spent 15 years with Kaplan and Norton—the pioneers behind the Balanced Scorecard—turning strategy into actionable outcomes. A self-described "tech geek," Dylan bridges technology and management, embedding his passion into ClearPoint’s code to ensure the software delivers flexible, approachable solutions for complex enterprise challenges.

To quote the movie Mean Girls: "The limit does not exist."

Table of Contents

Artificial Intelligence is transforming the way we work, decide, and live. It is especially apparent in the realm of management reporting, where AI recommendations are reshaping the landscape and allowing leaders to make smarter, faster, and more informed decisions.  

Let's explore the technology behind these transformative tools. We’ll start by exploring the inner workings of large language models (LLMs), the engines behind AI recommendations, and then navigate through the concept of context windows, a critical component that makes these models so effective.

Throughout, we’ll draw parallels with our philosophy at ClearPoint Strategy of putting information into context, and we’ll highlight why—despite their impressive capabilities—AI tools serve to augment human expertise rather than replace it.

Demystifying LLMs

How LLMs Work

At their core, large language models (LLMs) are incredibly sophisticated text prediction engines. Think about the simplest form of text generation: when you start a sentence, your brain automatically predicts the next word based on context, experience, and learned patterns.  

LLMs operate on a similar principle, but at a scale and complexity that surpass human capability. They have been trained on vast swaths of data, ranging from books and articles to websites and social media, enabling them to capture patterns, nuances, and even cultural idioms.

The training process involves exposing the model to an enormous corpus of text, where it learns to predict the next word in a sequence. This might sound simple, but the process requires immense computational power and advanced algorithms that allow the model to capture not just the literal words, but also the underlying structure, tone, and context of the text. When you ask an LLM a question or give it a prompt, it leverages these patterns to generate text that is coherent, contextually appropriate, and often surprisingly insightful.

The Power of Text Prediction

While it’s easy to reduce LLMs to the concept of “predicting text,” this process is far more powerful than it appears on the surface. When an LLM generates text, it’s not simply stringing words together randomly—it’s synthesizing information, drawing on a vast background of knowledge, and tailoring its response based on the context you provide. This ability makes LLMs valuable in many applications, like drafting emails, writing code—even providing insights in management reporting.

Consider the analogy of a seasoned advisor who has read thousands of reports and can quickly identify patterns and trends. An LLM works in much the same way. It sifts through its extensive training data and presents you with text that aligns with the context of your request. It is this depth of understanding, combined with the simplicity of text prediction, that makes AI recommendations so compelling.

The Magic of Context Windows

What Are Context Windows?

One of the most revolutionary concepts in the realm of LLMs is the idea of a “context window.” A context window refers to the amount of text (or data) that an AI model can consider at one time when generating a response. Imagine trying to solve a puzzle: the more pieces you have in front of you, the better you can see the overall picture. Similarly, an LLM with a large context window can analyze more information simultaneously, leading to more coherent and insightful outputs.

In technical terms, the context window determines how much previous text the model "remembers" while generating new text. Earlier models were limited to short spans of text, which sometimes resulted in outputs that were disjointed or lacked depth. Today’s LLMs, however, boast context windows that can span hundreds of thousands of words, allowing them to maintain a high level of consistency and detail throughout a conversation or document.

How Context Windows Enhance Analysis

When an LLM can take into account more information at once, it can make connections between disparate ideas, draw more nuanced conclusions, and provide recommendations that are well-informed by the entirety of the available data. Like having a detailed map when planning a journey, rather than just a rough sketch of the road ahead.

larger context window = richer analysis

In management reporting, this context is king. A well-crafted report doesn’t just list numbers and trends, it tells a story by weaving together insights, historical performance, and future projections. An LLM equipped with a substantial context window can replicate this process by analyzing extensive datasets and reports to generate summaries and recommendations that capture the full narrative. In essence, context windows enable AI to “see” the whole picture, thereby improving the quality and relevance of its output.

The ClearPoint Philosophy

The Need for Context in Management Reporting

At ClearPoint Strategy, we’ve always believed that context isn’t just a nice-to-have—it’s essential. In the world of management reporting, numbers without context are just figures; they’re only meaningful when tied to the story behind them. This is why so much of our work revolves around ensuring that data is presented in a way that’s actionable and relevant. Whether it’s through dashboards, scorecards, or detailed reports, our goal is to help organizations see the full picture so they can make decisions that drive success.

Much like LLMs, ClearPoint’s approach is rooted in understanding context. We strive to present information that not only shows what happened, but also why it matters and what it means for the future. In both cases, whether you’re using an AI tool or a traditional reporting system, the challenge is the same:

Making sense of vast amounts of data and turning it into insights that are both actionable and comprehensible.

Parallels Between AI and Human Thinking

Human cognition thrives on context. Every decision we make is influenced by a mix of historical data, personal experiences, and situational awareness. When we read a report, we’re not just absorbing numbers—we’re interpreting them through the lens of our own experiences and the broader context in which they occur.

LLMs mimic this process by using context windows to “remember” relevant information while generating text. This allows them to provide more nuanced responses that take into account the subtleties of language and meaning. The more context an AI model can process, the more it can mirror the way humans naturally think and communicate. And this is precisely why AI recommendations, when used correctly, can elevate the quality of management reporting. They bring a level of analytical depth and coherence that complements human expertise.

Balancing Data and Context

Context Window vs. Knowledge Base

One of the most fascinating aspects of LLMs is the interplay between the context window and the vast amount of data on which the model has been trained. The knowledge base of an LLM represents all the information it has ever absorbed during training—an almost encyclopedic repository of facts, figures, and narratives. The context window is like the AI’s short-term memory, enabling it to focus on the task at hand by keeping relevant pieces of information “in mind” as it generates a response.

This balance is crucial. No matter how extensive the training data is, if the context window is too small, the model might fail to draw meaningful connections or maintain coherence over longer documents. Conversely, a large context window can allow the model to tap into that vast knowledge base more effectively, synthesizing information in a way that feels both insightful and relevant.

For instance, imagine you’re preparing a report that details last quarter’s performance and also integrates market trends, competitor analysis, and future forecasts. A robust AI tool with an expansive context window can simultaneously consider all these elements, resulting in a report that doesn’t only state facts, but rather tells a compelling story. This synthesis of broad knowledge and focused context is where the real magic happens—and it’s the secret sauce behind AI recommendations that are both deep and actionable.

Explore ClearPoint’s robust AI tools for performance management

The Role of Data in AI Recommendations

It’s important to recognize that while context windows play a pivotal role in generating coherent and insightful analysis, the underlying data is equally critical. The model’s training data represents almost the sum total of human knowledge up to a point in time. This data forms the backbone of its ability to understand language, identify patterns, and make predictions.

In management reporting, the quality of the data you feed into your analytical tools can dramatically affect the insights you gain. Similarly, the “knowledge” of an AI is only as good as the information it has been trained on. This is why maintaining data quality, relevance, and timeliness is paramount. AI recommendations are transformative only when they are built upon a foundation of accurate and context-rich data.

Related: “Spring Cleaning” Your Reporting

Moreover, the interplay between data and context is an ongoing conversation. As AI tools evolve, so too does our understanding of how best to harness them. At ClearPoint, we emphasize continuous improvement, ensuring that our systems are not only processing data accurately, but are also interpreting it in a way that aligns with the broader strategic context of our clients’ businesses.

The Human Element: Augmenting, Not Replacing, Expertise

One of the most common misconceptions about AI and LLMs is that they are poised to replace human workers. In truth, these tools are designed to complement human expertise, not supplant it. Just as a calculator doesn’t replace a mathematician, but rather helps them work more efficiently, AI tools serve as a powerful extension of our own cognitive abilities.

AI recommendations in management reporting can help uncover insights that might otherwise go unnoticed, highlight trends in massive datasets, and even suggest actionable strategies. However, these insights are most valuable when they are evaluated and contextualized by human experts. The art of decision-making involves judgment, ethics, and an understanding of the unique nuances of each business scenario—areas where human intuition and experience remain irreplaceable.

In practice, this means that the role of AI is to empower managers and decision-makers with richer, more nuanced information. When used effectively, AI can free up valuable time by automating routine tasks and presenting data in a more accessible format. This, in turn, allows human professionals to focus on the strategic and creative aspects of their work, making the final decisions both data-driven and human-centered.

Best Practices for Integrating AI Recommendations

To truly harness the power of AI in management reporting, it’s essential to integrate these tools thoughtfully. A few best practices to consider:

  • Validate and Cross-Check: Always validate AI-generated insights against your own data and expertise. This helps ensure that recommendations are accurate and relevant.
  • Maintain Data Quality: Just as with any tool, the output is only as good as the input. Invest in robust data management practices to ensure that your AI tools have access to the most accurate and timely information.
  • Foster a Collaborative Environment: Encourage a culture where AI is seen as a partner rather than a replacement. Facilitate ongoing training and collaboration between technical teams and business experts.
  • Stay Updated: The field of AI is evolving rapidly. Regularly update your tools and processes to incorporate the latest advancements, ensuring that your management reporting remains cutting-edge.

By following these, organizations can create a synergistic relationship between AI tools and human expertise, leveraging the strengths of both to achieve truly transformative results.

The Future of AI in Business and Beyond

Revolutionizing Decision Making

The integration of AI into management reporting isn’t just a theoretical exercise—it’s already making a tangible difference in the business world. With the ability to process large volumes of data quickly and generate insights that might otherwise take hours—days, even—to uncover, AI is revolutionizing the way organizations approach decision-making.

Take the process of monthly financial reporting. Traditionally, compiling and analyzing financial data can be a labor-intensive process, prone to human error and oversight. With AI-powered tools, data can be aggregated and analyzed in real time, flagging anomalies, identifying trends, and even predicting future performance. This both speeds up the reporting process and provides management with a more accurate and actionable view of the business.

Another area of significant impact is in predictive analytics. By analyzing historical data in the context of current market trends, AI can forecast future outcomes with a level of precision that was previously unattainable. This allows companies to proactively address potential challenges and seize opportunities before they become apparent through traditional analysis.

Evolving Context Windows and Analytical Depth

Imagine a future where AI systems can seamlessly integrate information from global data streams, historical archives, and real-time analytics—all while maintaining an incredibly large context window. The depth of analysis such systems could achieve would be unparalleled. Reports could detail past performance while also simulating multiple future scenarios, taking into account an almost infinite array of variables. This level of analytical depth would empower businesses to plan with unprecedented accuracy and agility.

And, as context windows grow, the gap between machine-generated insights and human strategic thinking will continue to narrow. The AI of tomorrow will be able to offer nuanced perspectives that rival, and in some cases complement, the expertise of seasoned professionals. However, the essential role of human judgment will remain critical. No matter how advanced AI becomes, the interpretation, ethical consideration, and creative application of insights will always be tasks best suited to people.

AI as a Collaborative Partner

In this brave new world, AI will evolve into a true collaborative partner. Rather than functioning as a black box, AI systems will be designed with transparency and interpretability in mind, enabling users to understand how conclusions were reached. This transparency will build trust and empower organizations to fine-tune their decision-making processes as they grow.

At ClearPoint, and in broader management reporting circles, the conversation is already shifting from “Will AI replace us?” to “How can AI help us be better?” This shift is indicative of a more mature understanding of technology’s role in business—a recognition that tools like AI, when used responsibly and intelligently, can unlock new levels of productivity and insight.

As we look forward, the potential of AI in transforming business processes is virtually limitless. Iteration after iteration enabling AI to “think” with ever-greater depth and breadth will only improve the quality of insights that these models can provide. This evolution will bring about a world where decision-making is, yes, faster, but also more holistic, incorporating a wider array of variables and perspectives than ever before.

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