Strategic planning is easy to talk about but much harder to manage.
Most organizations have no shortage of priorities, initiatives, transformation programs, and leadership goals. The real challenge is making sure those priorities connect to actual work, and that teams can clearly see whether their efforts are moving the business forward.
Enter Objectives and Key Results, or OKRs!
OKRs give organizations a practical way to define what they want to achieve, measure progress, and connect day-to-day execution back to strategic value. When implemented well, OKRs help leaders answer a few important questions:
Many organizations already have objectives in place. The hard part is creating measurable Key Results and tracking them consistently across the enterprise. As organizations grow, this becomes even more difficult. Goals spread across departments, data lives in different systems, and leadership often lacks a clear view of how work is contributing to strategy.
provides a valuable solution by giving organizations a structured way to define, organize, measure, and report on OKRs.
What Are OKRs?
OKRs are a goal-setting and measurement framework made up of two parts: Objectives and Key Results.
An Objective describes what the organization wants to achieve.
It should be clear, meaningful, and tied to a strategic priority.
A Key Result defines how progress toward that Objective will be measured.
It should be specific, measurable, and outcome-focused.
A simple way to think about it:
Objective: Where do we want to go?
Key Result: How will we know we are getting there?
For example, an organization may define an Objective such as:
Improve enterprise portfolio visibility for strategic decision-making.
That Objective is important, but by itself, it is difficult to measure. To make it actionable, the organization needs a Key Result, such as:
Increase the percentage of monthly status updates in Clarity for priority initiatives.
Now the Objective is paired with a measurable target. Leaders can track progress, review status updates, and determine whether the initiative is on track, at risk, or off track. This is the real value of OKRs. They move strategy out of slide decks and into measurable execution.
Why OKRs Matter for Portfolio Management
OKRs are especially useful in strategic portfolio management (because they help connect investments to value.
Without a clear OKR structure, organizations may approve projects because they sound important, support a stakeholder request, or align loosely with a broad business goal. But over time, it becomes difficult to understand whether those projects are delivering the expected value. The risk is delivering a project successfully but still failing to create meaningful strategic value.
OKRs help organizations look beyond activity and focus on impact by creating visibility between strategy and execution. They allow organizations to define strategic priorities, link work to those priorities, and measure progress using agreed-upon indicators.
The Difference Between Objectives, Key Results, and Metrics
One common challenge with OKRs is understanding the difference between Objectives, Key Results, and the metrics used to track them.
- An Objective is the desired outcome. It should be clear and strategic.
- A Key Result is the measurable result that shows whether the Objective is being achieved.
- A Metric is the data point or measure used to track progress against the Key Result over time
For example:
- Objective: Improve enterprise portfolio visibility for strategic decision-making.
- Key Result: Standardize reporting for priority initiatives across major business areas.
- Metric: Percentage of priority initiatives with status updates in Clarity.
In the first month, only a small percentage of initiatives may have status updates. The metric may be marked At Risk. Over time, as more teams adopt the process and begin reporting consistently, that percentage should increase.
This type of structure gives leaders more than a static goal. It gives them a way to monitor movement, identify risk early, and understand whether progress is improving over time.
Real-World Example: Creating Portfolio Visibility with Measurable OKRs
A strong OKR should connect a strategic priority to measurable progress.
Rego’s work with UCSF Health is a good example of an enterprise challenge where OKRs helped create structure and visibility.
UCSF Health needed a better way to manage complex work across clinical, campus, and research domains. Like many large organizations, teams were working across disconnected systems, with manual reporting processes and siloed data. Leaders needed a clear way to understand project status, portfolio health, priorities, and resource needs.
With Rego and Clarity, UCSF Health created a stronger foundation for enterprise portfolio visibility, executive reporting, resource planning, and strategic alignment.
Objective: Improve enterprise portfolio visibility for strategic decision-making.
Key Results:
Common Challenges When Tracking OKRs
Although OKRs are simple in concept, they can be difficult to manage in practice. Many organizations run into similar issues:
These challenges can be overcome by creating a consistent structure for defining OKRs, linking them to investments, and tracking progress over time.
Best Practices for Defining OKRs
Rego recommends the following best practices:
✅ Make Objectives Clear and Outcome-Focused
A good Objective should describe a meaningful business outcome. It should be easy to understand and important enough to guide decisions.
Instead of: Improve systems
Use: Improve portfolio visibility for executive decision-making
The second version is clearer and more tied to value.
✅ Make Key Results Measurable
A Key Result should include a measurable target whenever possible.
Instead of: Support adoption of the new platform
Use: Achieve 80% active usage among target users within six months
This gives teams a clear way to evaluate progress.
✅ Avoid Confusing Activities with Results
This is one of the most common OKR mistakes. Activities describe work being done. Results describe the outcome of that work. Both are important, but OKRs focus on the result.
| Activity | Result |
|---|---|
| Launch a training program. | Increase trained user adoption to 90%. |
✅ Use a Consistent Reporting Cadence
OKRs should be reviewed regularly. Monthly updates are often a good starting point, though some organizations may choose weekly or quarterly reporting, depending on the pace of work.
The key is consistency. If updates are sporadic, leaders cannot rely on the data.
✅ Capture Context, Not Just Status
A red, yellow, or green status can be helpful, but it’s often not enough. Comments provide the context leaders need to understand what is happening and what action may be required.
An At Risk status without explanation creates more questions than answers.
✅ Keep the Structure Simple Enough to Use
OKR tracking should not become so complex that teams avoid using it.
Start with a structure that supports the decisions your organization actually needs to make. You can always mature the framework over time.
How Clarity Supports OKR Tracking
Clarity gives organizations several ways to configure and manage OKRs. Because the platform is flexible, there is no single required approach. Clarity’s configuration can match how your organization defines strategy, organizes portfolio data, and reports progress.
Custom Investment Types (CITs) in Clarity
One effective approach to holding the strategic structure for OKRs is to use a Custom Investment Type, or CIT. This can include value streams, Objectives, Key Results, and related metrics.
A custom object can then be used to capture recurring measure of updates, such as status, date, and comments.
This configuration allows teams to:
| Value Stream | The highest-level strategic grouping. |
|---|---|
| Objective | The strategic outcome the organization wants to achieve. |
| Key Result or Strategy | The measurable result indicates progress toward the Objective. |
| Metric | The measure used to track progress against the Key Result. |
| Measure Updates | Recurring status updates that show how the metric is performing over time. |
These levels create a logical flow from strategy to measurement.
What Leaders Gain from OKR Tracking in Clarity
When OKRs are defined clearly and tracked consistently in Clarity, organizations gain a stronger foundation for strategic portfolio management.
- Leaders can better understand which initiatives support strategic goals, where progress is being made, and where intervention may be needed.
- Teams gain a clear view of how their work contributes to business outcomes.
- Portfolio managers get better data for reporting, prioritization, and planning.
The result is a more connected approach to execution.
Instead of managing projects in isolation, organizations can manage work in the context of strategy, value, and measurable progress.
Rego Can Help
Defining OKRs is a great start. Building a practical, scalable way to track them is the next step.
Rego can help organizations design an OKR framework that fits their business, configure Clarity to support that framework, and create reporting structures that make progress easier to understand.
Our experienced practitioners work with organizations to define measurable Objectives and Key Results, connect OKRs to portfolio and project data, and build the right Clarity configuration for long-term visibility and adoption.
Whether your organization is just starting with OKRs, improving an existing framework, or moving into the Modern User Experience, Rego can help create a path that is practical, scalable, and aligned to the way your teams work.
To learn more, reach out to Rego to discuss how Clarity can support OKR tracking across your organization.
About the Author: Liz Palisin
