How to Run an OKR Pilot

It’s official — OKRs have hit the mainstream. No longer confined to tech giants like Twitter and Adobe, OKRs are being adopted en masse by large organizations across all industries like John Deere, The Washington Post, and Dish.

If you’re reading this, you already know how OKRs can create transparency, improve focus, and drive alignment for your organization. And you probably hope implementing OKRs will help you better define your goals, understand the process of achieving them, and track your progress along the way.

The question is no longer “What are OKRs?” 

Today the question is, “How do we adopt OKRs?” 

But let’s be honest, to do anything at scale is complex — especially OKRs. That’s where pilot projects come in. For medium-to-large organizations, starting with an OKR pilot is a great first step.  

This article will help you design and run a successful OKR pilot within your organization.

Don't have time to read the full article now? Download the pdf and save for later

An OKR pilot is a mini version of an OKRs project that tests the viability before launching the program across an entire organization. An OKR pilot generally begins with several people or a small team managing the whole project.  

And since pilot projects can be expensive, they generally make more sense for medium to large enterprises because they’re a relatively cheap alternative to full-scale deployment.  

In the case of smaller organizations (up to 300 employees), pilots tend to be expensive, have artificial boundaries, and may create more problems than they solve. 

What does an OKR pilot test?

Seeing if OKRs work for your organization takes more than simply plug-and-playing the methodology. Your organization is unique in its challenges, so your pilot be tailored to this. In our experience, it’s best to organize pilots in stages to test one aspect:

• Conceptual fit: Do OKRs fit in the culture and way of work of your organization?
• Leadership engagement: Is there leadership buy-in with OKRs?
• Broad engagement: Are non-leadership employees and individual contributors involved with the methodology?
• Technology fit: Does your technology enable people to focus on their objectives? Does it work for distributed teams and hybrid work?
• Scale: Are the process, logistics, and technology able to support OKRs at scale? 

How your OKR pilot duration differs from an implementation

While the scale of an OKR pilot is smaller than an organization-wide implementation, that’s not the only important difference. The length of your OKR pilot is neither endless nor one-size-fits-all — the duration of the pilot is highly dependent on your chosen objective.

A meaningful pilot project has a test group of between 50 and 500 people.  

With this 50-500 range in mind, you should also try to include people from various levels and departments in the organization. We’ll discuss the rationale for this in our Deciding the Pilot Test Group section.

For example, if you only want to test if people can create sensible OKRs, a two-week period may be more than enough. However, a real-world pilot project usually aspires beyond the simple comprehension of OKR methodology.

For a smaller organization (up to 500 people), the rule of thumb is pilots should last between three and six months, with real results visible after the sixth month.

For larger organizations, because of the scale and complexity, the pilot project should last one year. The caveat with an enterprise pilot project is that it should be progressive — with every quarter, the scale of the project should be increased to the point of organization-wide OKR implementation. 

Objectives and key results (OKRs) are one of the most straightforward management methodologies.

• You set qualitative objectives, which describe your intent and aspiration
• You define three to five quantitative key results per objective, which you use to define and measure success

In a way, it is this simplicity that made them so popular and widespread. But OKRs are not without their own complexities. OKRs holistically replace the strategy planning for your entire organization, presenting unique roadblocks and friction points from mental, strategic, and operational standpoints.

Learn more about the OKR fundamentals

The advantage of OKRs

If you're at this stage of consideration for an OKR pilot, you probably already know why you want to implement OKRs. However, we can’t stress enough the importance of revisiting the true purpose of your OKR pilot program. This reflection enhances the clarity of your objectives in the long term.

While the reasoning will change from company to company, there are three essential benefits OKRs bring to all organizations:

• Transparency: know what is happening
• Focus: work on what is most important
• Alignment: work with others toward what is important 

These benefits may be what you’re looking for from OKRs. However, the ultimate promise of OKRs can be simplified into one outcome — achieving better results.

OKRs aren’t a plug-in, they’re a transformation.

Building on the broad promises of OKRs and contextualizing them to your organization will make it easier to shape your process, measure the outcomes, and create the change you wish to see. 

The challenge of OKRs

OKRs present a standard set of challenges regardless of your company’s size.

Challenge 1: outcome mentality

The first challenge of OKRs is about changing the mindset of your organization from output to outcomes — shifting the focus from completing tasks to achieving results. 

Professionally, most people define success as completing tasks, and asking your team to think in terms of results is not easy. 

While this is a key benefit of OKRs, changing habits is an immense mental load. 

Challenge 2: process  

Second, OKRs are a process change. They initially represent the idea of just another new thing to do. 

So, not only are you asking your organization to change the way it thinks, but you are also asking people to understand something fundamentally new.

Without the right preparation of processes, tools, and training, your employees may react to the introduction of OKRs with emotions ranging from mild annoyance to openly displayed contempt.

Challenge 3: change management  

Finally, the relative simplicity of OKRs intentionally leaves much to interpretation. 

Best case, you have the freedom to shape the process to your unique needs. Worst case, you complicate your strategy with dozens of subjective, ad hoc, hard-to-manage OKR interpretations.

Every organization that adopts OKRs faces these challenges, and at scale (thousands of people) they become harder and more complex. The solution to these challenges begins with a comprehensive approach to change management. 

Change management, especially in enterprises, is nothing new. While many approaches can apply to OKRs, the Model for Managing Complex Change is particularly useful.

The model represents any change as a matrix of five components:

• Vision: why are you doing this? (In this case, implementing OKRs)  
• Skills: do you have the necessary skills to implement the change?
• Incentives: what is in it for people you expect to participate?
• Resources: do you have the necessary tools, budget, time, etc.?
• Action plan: do you have the program to execute? 

It’s imperative to answer these questions any time you’re looking to implement complex changes within your organization. To successfully introduce change, all five components must be present. However, if one component is missing, different types of failures can occur.

An OKR pilot is designed to bring each component of change management to the forefront. Being experimental by nature, it’s natural to have more challenging components of the OKR pilot depending on your organization.  

Based on this change management model, if you can accurately identify your ongoing challenges (purple boxes), you can shift focus to which component of change is missing in your OKR pilot.  

The primary reason OKR pilots fail is because companies fail to define the pilot itself. Before you start your pilot program, there are three foundational questions you need to ask and answer to help you be successful:

1. Why are you running the pilot project?
2. Which risk are you trying to minimize?
3. What is your pilot objective? 

Why are you running the pilot project?

While there are many reasons why an organization may run a pilot project, they all boil down to minimizing risk. Within an OKR pilot program, the type of risk you’re trying to minimize relates to one of four circumstances:

1. Prove OKRs can deliver one of the core promises
2. Prove OKRs can work in your organization
3. Prove OKRs can work at scale
4. Prove an OKR platform/software can work 

Prove OKRs can deliver one of the core promises  

Perhaps you’re a skeptic of the OKR methodology. You want to see either better alignment, increased transparency, or enhanced focus in execution for yourself. Wasting time on a methodology that may not work is a significant risk.

Prove OKRs can work in your organization  

Perhaps you’re an OKR believer already, but you’re unsure if they are the right fit for your organization’s culture or workflow. Regardless of the outcomes, if your teams can’t understand OKRs at their core, this is an intolerable risk.

Prove OKRs can work at scale  

Perhaps you’ve seen OKRs work for smaller teams, but you’re worried about the complexities and challenges of large-scale implementation. If OKRs only work in certain circumstances, risking your approach to strategy execution must be calculated.

Prove an OKR platform/software can work  

Perhaps you’re already convinced OKRs are right for your organization and they will work, but you want to test OKR solutions before beginning the process. Vetting, purchasing, and integrating software is a resource risk.

Learn more about succeeding at large-scale OKR implementation

Establish your pilot objective

The core purpose of running a pilot is to prove or disprove something on a smaller scale, in a controlled environment, and with minimal risk.

You may define your OKR pilot in any way, but the size of your organization and your unique challenges are great outlines for your desired outcomes. Through our experience, we have identified six distinct categories as fundamental to the OKR pilot success:

• Onboarding: can we get people started with OKRs?
• Activity: how active and engaged are people with the process?
• Alignment: are our organizational goals more aligned with OKRs?
• Transparency: have OKRs reduced silos and improved collaboration?
• Focus: are we more focused on what is important with OKRs?
• Attainment: are we achieving our objectives with our shift to OKRs?

With these categories in mind, defining what success looks like and what needs to happen for the pilot to be declared a success inspires the objective. At the end of the pilot, success or failure should be clear.

You can try the OKR methodology to define your pilot project:

Pilot project OKR example  

• Objective: Improve organizational focus
• Key result 1: Reduce the number of in-progress projects to 12
• Key result 2: Complete 60% of projects on time
• Key result 3: Complete 75% of projects on or below budget
• Timeline: 12 months
• Owner: Helen Smith, VP Operations

See how an OKR platform can help you plan your pilot

With the objectives decided, you’re ready to choose the participants. The very definition of a “pilot” is a subset of the entire organization, but deciding which subset isn’t always easy.

Most companies start with the idea of piloting OKRs exclusively with executives or top management. Executives should participate, but the pilot should be as immersive and inclusive as possible.  

In our experience implementing OKR pilots, the best practice is to add top management horizontally, then choose one or two functions vertically — IT, marketing, etc. 

Piloting OKRs with a group that will clearly demonstrate positive or negative results is key. Is there a group in your organization working on a big project who could use some guidance from OKRs? Or a group less sensitive or reactive to changes OKRs will bring?  

You want your pilot to be useful and its demographic to be practical.

The next question concerns how many people will participate in the pilot. With too many people, your pilot will be difficult to manage and inhibited from the beginning. But with too few people, testing alignment or transparency through OKRs is tough. You need some level of scale to understand the benefits — usually between 50 and 500 people. 

Designating an OKR sponsor and an OKR champion  

For OKRs to succeed, there are two key roles in the process: OKR sponsor and OKR program champion. Depending on the size of your organization, multiple people can fulfill these roles, but it’s critical to have at least one designated person per role before starting with OKRs.

• OKR sponsor: works to establish OKR credibility and manage the OKR pilot strategy
• OKR champion: the expert on all things OKR, responsible for the execution of the pilot 

OKR sponsor  

Typically an executive, often a CEO or COO, this person lends authority and credibility to OKRs. Your OKR sponsor sets the success criteria and should be involved throughout the pilot’s development, affirming that OKRs are not a “set it and forget it” initiative.  

At Quantive, we believe in the importance of sponsors to the point we refuse to engage with prospects if there’s not one.

OKR champion  

Your OKR champion is a highly operational role — the ultimate decision maker, POC, and leader of any other OKR decision makers. In larger organizations, all the OKR champions collaborate to ensure the OKRs process is established, OKRs are present, and progress is being tracked.  

The typical responsibilities of an OKR champion include:

• Being the internal expert on everything OKRs
• Ensuring the process is being followed, OKRs are defined, and progress is tracked
• Removing bottlenecks, choosing software to track and manage OKRs, etc. 
• Facilitating decision making around the pilot process:
  • How many OKRs?
  • Who owns the OKRs?
  • How often are OKRs planned?

As you move into the final details of your OKR pilot, a decision must be made around the planning period and cadence.  

Structuring the OKR planning period  

The planning period, or planning session as it is defined in Quantive, is nothing more than a timeframe in which objectives are to be achieved.

The most common timeframe is a calendar quarter — most organizations will have OKRs for Q1, Q2, Q3, and Q4. We have seen organizations experiment with shorter periods, like a month, or more extended periods like six months.  

We strongly encourage starting with quarters and only changing the planning period if there’s an urgent reason to do so.

The exception to this rule of thumb is top-level organizational OKRs. These tend to be more strategic and usually set within a year timeframe. In that case, the organization will set its OKRs for the year, while departments, teams, and individuals will support those strategic objectives through more tactical quarterly OKRs.

Setting your OKR cadence and check-ins  

The OKRs planning period isn’t the only time-relevant question for the OKR pilot — the next step is deciding how often you and your team will discuss OKRs. For example, if you’re planning your OKRs in quarters, it’s a common practice to go over the progress weekly or bi-weekly.  

Omitting regular check-ins is a sure way to fail with OKRs, as your teams will disconnect from their objectives and forget the process.

Even though you will find your personal rhythm, we suggest starting with bi-weekly meetings. To help soften the transition to OKR check-ins, aim to make meetings short, but effective. During this meeting, we recommend focusing on problematic OKRs and prospering OKRs, with everything in the middle being second priority.  

The logic? Seeing what can be done about failing objectives, doubling down on the ones going well, and extracting insights from both.  

Finally, make sure to update all OKRs before the meeting — we often see the first 10-15 minutes of the check-ins being wasted with people updating their progress.

Learn more about all the OKR cycle best practices

While making mistakes is to be expected in progressing along the OKR learning curve, some mistakes are more detrimental than others. Here are the three most common mistakes that can derail your OKR pilot project:

1. Too many OKRs
2. Confusing objectives and key results
3. Outcome vs output resistance

Too many OKRs  

One of the key promises of OKRs is focus. 

When organizations first implement OKRs, a typical mistake is defining too many of them.

OKRs don’t have some magical power to focus people. The way one achieves focus is simply by limiting the number of OKRs a person or team can own, up to three per quarter. 

Confusing objectives and key results  

Objectives are qualitative, while key results are quantitative. Integrating numbers in your objective complicates key result creation — while this is a technicality, it deflates the purpose of key results.  

Let’s look at an objective and key result:

• Objective: Hit Q2 growth targets
• Key result 1: Increase revenue to $35m  

What if your first key result — Increase revenue to $35m — was an objective? While it is aspirational in the “Increase revenue” portion, it is almost impossible to come up with a key result were this the objective.  

Outcome vs output resistance  

A common challenge is framing OKRs in terms of results. A rigid focus on sheer output stifles the potential of OKRs and turns them into nothing more than a glorified task list. Most people still think of “what I need to do” as opposed to “what I need to achieve.”

OKRs are not about doing tasks but achieving results. The way to fix this mistake is to keep asking “why?” until the desired outcome reveals itself.

The true magic of OKRs kicks in once we start thinking in terms of outcomes.

See all of the most common OKR mistakes you should avoid in your pilot 

We’ve built this guide to make your OKR pilot as seamless as possible. 

You’ve learned what an OKR pilot is, how the OKR methodology can benefit your organization, and gained tactical advice on running your OKR pilot. From teaching OKRs and change management, to deciding your pilot objective and choosing your test group, you’re ready to start your OKR pilot.

But as you have learned, there are many moving pieces in the planning, implementation, and retrospective of your pilot. OKR software and OKR consulting can help you further streamline your pilot by organizing your objectives, formalizing your process, and helping you track your progress.

Learn how Quantive's OKR software helps you achieve the best possible results.

Quantive empowers modern organizations to turn their ambitions into reality through strategic agility. It's where strategy, teams, and data come together to drive effective decision-making, streamline execution, and maximize performance.    

As your company navigates today’s competitive landscape, you need an Always-On Strategy to continuously bridge the gap between current and desired business outcomes. Quantive brings together the technology, expertise, and passion to transform your strategy and playbooks from a static formulation to a feedback-driven engine for growth.    

Whether you’re a fast-growing scale-up, a mid-market business looking to conquer, or a large enterprise looking for innovation, Quantive keeps you ahead – every step of the way. For more information, visit www.quantive.com.