The Secret to Scalable OKRs: Stop Using Spreadsheets
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.

It's time to challenge the status quo and disrupt the way things have always been done—one OKR at a time.

Table of Contents

Most OKR implementations fail—not because the framework is flawed, but because organizations try to manage them manually. Spreadsheets, slide decks, and scattered documents lead to misalignment, wasted effort, and goals that quickly lose relevance. Without technology to automate tracking, visualize progress, and keep teams engaged, Objectives and Key Results become just another management fad.

As someone who’s been deep in the trenches with OKRs for over a decade, I can tell you that manual management will fail. In my experience at ClearPoint Strategy (and through my personal journey of trial and error) I’ve seen firsthand how leveraging technology isn’t just a convenience—it’s a necessity—if you want your OKR program to succeed.

Let’s ruffle a few feathers in traditional management circles.

A History Lesson on OKRs and the Tech Evolution

The Early Days: Manual Processes and Clunky Systems

I still remember the early days of OKRs—back when many organizations relied on paper-based systems, emails, and even those notoriously error-prone spreadsheets. OKRs were revolutionary, but the process of setting, tracking, and reviewing them was anything but streamlined. It wasn’t uncommon to see managers spending hours aligning objectives with key results, only to have miscommunications derail progress before the quarter was even halfway over.

At that time, technology was more of a hindrance than a help. The available tools were limited, and many of us had to develop our own workarounds to make sense of the data. I remember one project where we used a combination of shared drives and outdated project management software—an approach that, in hindsight, was as effective as using a flip phone in the 21st century.

The Digital Revolution

Fast forward to today, and the landscape has changed dramatically. We now have robust, purpose-built platforms that allow real-time tracking, seamless integration with other business systems, and an array of analytics that were once unimaginable. The digital transformation not only made it easier to manage OKRs, but also elevated the strategic conversation across organizations.

I’ve seen companies—large and small—embrace technology to drive accountability and agility. Platforms like ClearPoint’s own suite (and many others out there) enable teams to set clear objectives, track progress in real time, and make data-driven decisions without the friction of manual updates. Efficiency? Good. Empowering leaders to focus on what truly matters? Great.

Controversial Yet True: The Resistance to Change

I’m not going to sugarcoat it: there’s been significant resistance to adopting new technologies for OKR management. Traditionalists argue that the “human touch” is lost when you replace face-to-face meetings with dashboards and digital reports. To that, I say—if your “human touch” means endless status meetings and tedious data entry, then maybe it’s time to upgrade your toolkit. Technology isn’t here to replace leadership, it’s here to augment it. When used correctly, digital tools can free up valuable time for meaningful conversations and strategic decision-making.

Why You Need Technology to Make OKRs Scalable and Repeatable

Real-Time Information

One of the biggest challenges with OKRs is keeping everyone on the same page. When you’re juggling multiple teams, projects, and goals, it’s too easy for things to fall through the cracks. Technology provides real-time visibility into progress, allowing managers and team members to see where things stand at any given moment. This both increases accountability and enables quick pivots if something isn’t working as planned.

Imagine this: you’re in a meeting discussing a key objective, and instead of relying on outdated reports, you can instantly pull up a live dashboard that shows exactly where you are. That’s the power of technology. No more “I think we’re on track” or “I believe we’re lagging”—you have concrete data right at your fingertips.

Integration with Other Systems

Your OKR platform should not exist in isolation. Whether it’s your CRM, ERP, or project management tool, integration is key. Modern technology allows for data exchange between systems, meaning you can automatically update progress without having to double-enter data or manually reconcile numbers.

In the ClearPoint platform, we’ve built integrations that allow our OKR software to pull in data from various sources, ensuring that every piece of information is accurate and up-to-date. This 1. reduces administrative overhead and 2. eliminates the risk of errors that occur when data is manually transferred from one system to another.

Explore ClearPoint Strategy’s Integrations

Collaboration and Communication

Technology has fundamentally changed the way we collaborate. With cloud-based platforms, remote teams, and real-time communication tools, it’s easier than ever to bring everyone together, regardless of their location. For an OKR program to be successful, it’s crucial that all stakeholders are aligned and working toward the same goals. Digital tools make collaboration more fluid, allowing for instant feedback and adjustments.

I’ve witnessed teams that were once siloed across different geographies suddenly become high-performing units, all because they had the right technology to facilitate open communication and planning. It’s not just about tracking numbers—it’s about fostering a culture of continuous improvement.

Data-Driven Decision Making

Data is king. Technology enables you to collect and analyze vast amounts of data, transforming raw numbers into actionable insights. With advanced analytics, you can pinpoint areas of strength, identify bottlenecks, and even predict future trends. This level of insight is critical for making informed choices that drive business success.

Gone are the days when gut instinct was the primary driver of strategic decisions. Today, you can rely on real-time data to guide your OKR program, ensuring that every objective is backed by solid evidence. This shift from intuition to data-driven decision making is one of the most significant benefits of integrating technology into your OKR rollout.

Scalability and Flexibility

One of the biggest challenges with any strategic framework is scalability. As organizations grow, their processes need to evolve. Manual systems simply can’t keep up with the pace of change in a modern business environment. Technology, on the other hand, is designed to scale. Whether you’re managing a team of 10 or 10,000, a robust digital platform can adapt to your needs.

I’ve seen startups pivot and grow rapidly because they had digital tools in place that could scale with them. Conversely, organizations that clung to outdated systems often found themselves overwhelmed by the sheer volume of data and the complexity of their operations. In my view, if you’re not prepared to scale your OKR program with technology, you’re setting yourself up for stagnation.

Manual Processes Kill Innovation

Here’s the unfiltered truth: clinging to manual processes is a surefire way to stifle innovation. In an era where technology can automate tedious tasks and provide deep insights at the click of a button, relying on manual methods is not just inefficient—it’s downright stupid.

There are those who argue that manual processes offer a “personal touch” that technology can’t replicate. To them, I say: If you’re still spending hours manually updating OKRs, you’re missing out on opportunities to innovate and drive real change.

Technology isn’t the enemy of human interaction, it’s the catalyst that enables us to focus on the things that truly require our attention. If you’re not using technology to streamline your process, you’re sabotaging your own potential.

Challenging the Status Quo

I’d like to spark some debate among traditionalists and tech enthusiasts alike.

  1. Opinion #1: Your Current OKR Processes Are Actually Counterproductive: It’s time to face the facts—your process for OKRs is probably a waste of time. While some argue that these methods provide a personal touch, I contend that they are nothing more than a productivity sinkhole. If you’re still updating spreadsheets by hand, you’re wasting precious resources that could be spent driving real initiatives.
  2. Opinion #2: Data Over Intuition—Always: There’s a romantic notion that great leaders rely on intuition and gut feelings. While I don’t entirely disagree, I firmly believe that data should be the cornerstone of every decision. Technology enables us to capture and analyze data in ways that were previously unimaginable. When you have real-time insights at your disposal, there’s no excuse for making decisions based solely on a hunch. It’s time to put numbers over narratives.
  3. Opinion #3: Tech Vendors Aren’t the Enemy—Your In-House Resistance Is: I’ve encountered plenty of resistance from within organizations, where employees are quick to blame tech vendors for the challenges of digital transformation. In reality, the real obstacle is often internal resistance to change. It’s not the software that’s the problem, it’s the mindset. If your team is unwilling to embrace new tools and methodologies, no amount of technology will save you. Leadership must drive the change, and that starts with a willingness to innovate and challenge the status quo.

Let’s be clear: OKRs themselves are not a magic solution to every organizational challenge. They require discipline, commitment, and constant refinement. However, when combined with the right technology, OKRs can become a powerful catalyst for transformation. Recognize that technology isn’t a cure-all—it’s a tool that, when wielded correctly, can amplify the impact of your efforts.

How ClearPoint Strategy Makes OKRs Work

At ClearPoint Strategy, we built our software to simplify OKR management while keeping organizations focused on execution. Here’s how:

  1. Align OKRs to Strategy: Our platform helps organizations map OKRs to strategic goals, ensuring teams stay focused on what matters.
  1. Automate Data Collection: No more chasing updates—ClearPoint pulls in data automatically, keeping OKRs current.
  1. Engage Teams with Dynamic Dashboards: Interactive reports make it easy to track progress, identify challenges, and celebrate wins.
  1. Enable Leadership Oversight: With real-time insights, leaders can quickly assess progress, reallocate resources, and drive accountability.
  1. Close the Loop with Action Plans: When OKRs aren’t on track, ClearPoint makes it easy to assign corrective actions and follow through.

Even build your own OKRs with ClearPoint's A.I.

ClearPoint Strategy vs. The Status Quo

Technology is the backbone of a modern, agile, and effective strategy.

I’ve seen it time and time again: organizations that invest in technology and embrace a data-driven approach not only achieve their objectives, but also form a culture of innovation and continuous improvement. I can confidently say the integration of technology into your processes isn’t just an option—it’s a strategic imperative.

I challenge you to take a hard look at your current processes. Ask yourself if you’re truly leveraging tech to the fullest, or if you’re settling simply because change feels uncomfortable. My experience in strategy consulting has taught me that the right technology can transform your OKRs from a cumbersome administrative task into a dynamic engine of growth and success.

My call to action: Embrace technology, challenge the status quo, and don’t be afraid to disrupt the way things have always been done. It’s time to leave behind the old ways and step boldly into the future of strategy management—one OKR at a time.

Remember:

  • Innovation Requires Discomfort: The road to technological transformation is rarely smooth. There will be challenges, and not everyone will be on board from day one. But if you’re serious about driving change, you need to be willing to push through the discomfort.
  • Data Is Your Best Friend: Relying on intuition alone is a gamble in today’s environment. Let the data guide you, and use it as the foundation for every decision you make.
  • Leaders Must Lead by Example: If you want your team to embrace technology and innovation, you have to be the first to do so. Show them that you’re committed to change, and they’ll follow suit.

Learn how ClearPoint can help your OKRs stay relevant, actionable, and aligned with your long-term strategy.