How to Run an

OKR Pilot

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Contents Introduction 3
What is an OKR pilot? 5
Why OKRs over other methodologies 10
Change management crash course 16
Planning your OKR pilot 19
Deciding the pilot test group 25
Defining planning periods and the OKR cadence 30
Avoiding common OKR pilot mistakes 33
Start your OKR pilot 38

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Introduction

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Introduction 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. Doing anything at scale is complex, especially OKRs

— this is where pilot projects come in. If you have a medium-to-large
organization, 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.

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What is an OKR pilot?

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What is an OKR pilot?
As a mini version of an OKR project, the OKR pilot tests the viability
of the framework before launching it across your entire organization.
An OKR pilot generally begins with several people or a small team
managing the whole project.

Since pilot projects can be expensive, they make the most sense for
medium-to-large enterprises because they’re a relatively cheap alternative
to full-scale deployment.

On pilot projects for SMBs and startups

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.

A full-scale rollout of OKRs is more manageable for a sub-300-person

organization — preparing a traditional OKR cycle is our recommended
course of action for startups and SMBs.

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What is an OKR pilot?
What does an OKR pilot test?
Seeing if OKRs work for your organization takes more than a simple
plug-and-playing of the methodology. Your organization is unique in its
challenges, so your pilot must be tailored to this. In our experience, it’s best
to organize pilots in stages to test one of the following aspects:

๫ Conceptual fit: Do OKRs fit in the culture and way of

work in 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 systems, logistics, and technology able to support
OKRs at scale?

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What is an OKR pilot?
How timelines differ between an OKR pilot vs.
full 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 (from the previous section).

A meaningful pilot project has

a test group of between 50
and 500 people.
With this 50-500 range in mind, you should strive 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.

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What is an OKR pilot? 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 OKRs.

For a smaller organization (up to 500 people), as a rule of thumb,

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 ideal
pilot project length is 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.

Now that you have the concept of a pilot’s scale and scope, why should you
choose to pilot OKRs instead of another goal framework?

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Why OKRs over other methodologies

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

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

The simplicity of OKRs has made them so popular and widespread, but
they are not without their complexities. OKRs holistically replace strategy
planning for your entire organization, presenting unique roadblocks and
creating friction from mental, strategic, and operational standpoints.

Pilots reduce strategic risk, helping

teams warm up to a new methodology.

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Why OKRs over other methodologies
The advantage of OKRs
If you're considering 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 Focus Alignment

Кnow what is happening Work on what is Work with others toward
most important what is important

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Why OKRs over other methodologies These benefits may be what you’re looking for from OKRs. But what
do transparency, focus, and alignment all have in common? They
lead to the ultimate promise of OKRs through one simple 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.

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Why OKRs over other methodologies
The challenge of OKRs
Regardless of your company’s size or goals, OKRs present a standard
set of challenges.

Challenge 1: Outcome mentality

First, OKRs are about changing the mindset of your organization from output
to outcomes — shifting the focus from completing tasks to achieving results.

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

load. Traditionally, task completion is the indicator of success, so asking
your team to think in terms of results is neither easy nor immediate.

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.

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Why OKRs over other methodologies Without the right preparation of processes, tools, and training, your
employees may react (rather than respond) to the introduction of OKRs with
emotions ranging from mild annoyance to open 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
they become harder and more complex. The solution to these challenges
begins with a comprehensive approach to change management.

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Change management crash course

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Change management crash course
Change management, especially in enterprises, is nothing new. While many
approaches can apply to OKRs, the Model for Managing Complex Change
(full illustration on the next page) is particularly useful.

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

Vision Incentives Action plan

Why are you doing What is in it Do you have the
this? (In this case, for people you program to execute?
implementing OKRs) expect to participate?

Skills Resources
Do you have the Do you have the
necessary skills to necessary tools, budget,
implement the change? time, etc.?

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Change management crash course It’s imperative to answer these questions any time you’re looking to
implement complex changes within your organization. However, if one
component is missing, different types of failures can occur.

An OKR pilot will bring each component of change management to the

forefront — it’s natural for some components to be more challenging
than others.

Based on this change management model, if you can accurately identify

your ongoing challenges, you can shift focus to which component of change
is missing in your OKR pilot.

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Planning your OKR pilot

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Planning 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 two foundational
questions you need to ask and answer if you expect to be successful:

Why are you running the pilot project?

What is your pilot objective?

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Planning your OKR pilot
Why are you running the pilot project?
While there are many reasons why your 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:

๫ Prove OKRs can deliver one of the core promises

๫ Prove OKRs can work in your organization
๫ Prove OKRs can work at scale
๫ Prove an OKR platform/software can work

Prove OKRs can deliver one of the core promises

Perhaps you’re a skeptical of the OKR methodology. You want to see

better alignment, increase transparency, or enhance focus in execution
for yourself. Wasting time on a methodology that may not work is a
significant risk.

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Planning your OKR pilot
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, it’s an intolerable risk if your teams can’t understand the OKR
methodology at its core.

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, you must be calculated when taking a risk on
your approach to strategy execution.

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.

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Planning your OKR pilot
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 the unique challenges that come with it) can help you outline your
desired outcomes. Through our experience, we have identified six distinct
categories as fundamental to the OKR pilot success:

Onboarding Activity Alignment

Can we get people How active and Are our organizational
started with OKRs? engaged are people goals more
with the process? aligned with OKRs?

Transparency Focus Attainment

Have OKRs reduced Do we understand what Are we achieving
silos and improved is important with OKRs? our objectives with
collaboration? our shift to OKRs?

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Planning your OKR pilot
With these categories in mind, your objective is inspired by:

๫ Defining what success looks like

๫ Defining what needs to happen for the pilot to succeed

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

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Deciding the pilot test group

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Deciding the pilot test group
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.

Our best practice is to add top

management horizontally, then choose
one or two functions vertically — IT,
marketing, etc.

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Deciding the pilot test group
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, you can’t truly stress test the
transparency, focus, or alignment of OKRs. You need some level of scale to
understand the benefits — usually between 50 and 500 people.

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Deciding the pilot test group
Designating an OKR sponsor and an OKR
champion
For OKRs to succeed, there are two key roles in the process: OKR sponsor
and OKR 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 champion OKR sponsor

The expert on all things Works to establish OKR credibility
OKR, responsible for the and manage the OKR pilot strategy
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

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Deciding the pilot test group
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 their importance to the point we refuse to

engage with prospects if there’s not an OKR sponsor.

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 OKR 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

๫ Guiding the OKR process
๫ Ensuring 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?

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Defining planning periods and the
OKR cadence

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

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Defining planning periods and the
OKR cadence 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 lose their
rhythm with the process.

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.

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Avoiding common OKR pilot mistakes

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Avoiding common OKR pilot mistakes
While making mistakes is to be expected in 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

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Avoiding common OKR pilot mistakes
Too many OKRs
One of the key promises of OKRs is focus.

When organizations first implement OKRs, they may be overly

ambitious by 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.

OKRs work best when you choose the most critical objectives to focus on.
With your focused objectives created, setting only three to five key results
ensures you’re measuring only what truly matters. Avoid stagnation and
divided focus by keeping your OKRs dialed in.

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Avoiding common OKR pilot mistakes
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.

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Avoiding common OKR pilot mistakes
Outcome vs output resistance
A common mistake is framing OKRs in terms of results. A rigid focus on
sheer output stifles the potential of OKRs, turning 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.”

Culture will make or break OKRs. They require engagement and personal
growth to work, not just task accomplishment. Building a culture on
the values of transparency, clarity, creativity, autonomy, and a focus on
outcomes over outputs is essential.

OKRs are about achieving results — keep asking “why?” until the
right outcome is revealed.

When employees understand their individual impact through “why?”

questioning, they’re better engaged with the methodology. The true magic
of OKRs kicks in once we start thinking in terms of outcomes.

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Start your OKR pilot

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Start your OKR 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 can help you
further streamline your pilot by organizing your objectives, formalizing your
process, and helping you track your progress.

OKR software helps you focus

on what really matters to achieve
the best results.

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Quantive is your bridge between strategy and execution. Founded on the
objectives and key results (OKR) methodology, our Strategy Execution
Platform is where businesses plan successful strategy, focus and align
teams to it, and stay on the leading edge of progress.

As your company looks to achieve the best possible results, you need
a modern approach to run your business and change your business.
The Modern Operating Model brings strategy, teams, and data together
to help make decisions faster, optimize operations, and drive better
business outcomes.

Whether you’re a large enterprise facing competitive disruption or a small

business leading the innovative charge, Quantive helps gets you where you
want to go.

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