Why wait to learn from your mistakes when you can learn from others?
Analyzing someone’s failures means determining what went wrong, why it happened, and how they responded. Through another person's failure, you can learn what not to do and consider what you should do in a similar situation.
This approach to learning can be an effective way to gain insight and knowledge, saving you from those difficult experiences with OKRs. In this guide, we'll explore a few of the pitfalls in OKR programs, then suggest tips on how to avoid them to increase your chances of success.
Who is this guide for?
- An executive, OKR Champion, or someone interested in improving strategy execution with the OKR methodology
- Familiar with OKRs — you understand the basics, have explored OKR books and resources, and want to deepen your understanding
- Curious how things can go wrong in an OKR rollout and how you can avoid missteps
By the end of this guide, you will:
- Understand the causes of OKR program failure
- Be able to identify OKR misconceptions
- Know how to avoid and address common pitfalls
Let's get started.
Pitfall #1: Jumping immediately into "we're doing OKRs"
Sometimes organizations implement OKRs for the wrong reasons. They may not understand the method or the goal of OKRs or they confuse it as a replacement for other methods, like performance management.
“For the wrong reasons” OKR scenario
Jessica, a Chief of Staff, devours a copy of Measure What Matters over the weekend. When she returns to work, she gathers a few folks from her team and shares, "I read this great book. We should do this. We're doing OKRs."
Her team scrambles to figure out what this means and how to make OKRs happen, using their own copies of the book as reference. Eventually, executives ask all employees to craft OKRs without proper justification or training.
No one knows why they're supposed to do this, and everyone thinks it's another way for leadership to ask for more reporting.
"Too often, the why OKRs and why now communications are weak or even absent from the broader communications needed to position OKRs correctly beyond the senior leadership team and OKR sponsors."
– Peter Kerr
A better way
OKRs are about turning good ideas into great execution.
They provide a common language to articulate your goals, track and measure progress, and reassess priorities. They encourage autonomy, ambitious outcomes, and cross-functional collaboration.
Every organization might have a different reason for why they use OKRs — the key is to have a compelling one.
Create a strong why statement. Author Simon Sinek suggests this simple framework:
To [insert contribution], so that [insert impact].
Here are some good why statements:
- To strengthen communication, so we can break down silos
- To increase focus and alignment, so we can maintain market leadership
- To improve accountability and evaluation, so we can keep our customer promises
Pitfall #2: Not having a strategy
According to writer and strategic advisor Roger Martin, strategy is a set of five choices for winning. For OKRs to work best, you need a strategy.
“The empty strategy” OKR scenario
Linda, an executive coach and OKR expert, discusses an OKR implementation initiative with her new client Doug, the COO of a manufacturing company.
In the meeting, Linda says, "If I asked you to share, within 10 minutes, the most updated company strategy document you have, what would you send me?"
Doug pulls up a spreadsheet containing the budget and something resembling a Gantt chart, then walks Linda through the document. Linda now realizes this client engagement just grew beyond OKR implementation.
"Work on the foundations by making sure the mechanics of the business are understood by everyone. Only in this way will teams be able to understand their role within the strategy and contribute."
– Antonio Civita
A better way
Don't confuse strategy with planning.
Strategy is a set of integrated choices. OKRs then provide a plan of execution toward that strategy. Without a strategy, OKRs risk becoming unfocused statements such as "Increase sales" and "reduce costs." In such cases, they may not be worth the effort.
Have a strategy in place, and make sure your strategy provides clear direction as an OKR foundation. Reflect on the questions from Roger Martin's Strategy Choice Cascade:
- What is our winning aspiration?
- Where will we play?
- How will we win?
- What capabilities need to be in place?
- What management systems must be instituted?
Refer to his Strategy Choice Structuring process or your own method of strategy development. Keep any strategy documents under five pages, as anything more is morphing into strategic planning territory.
Pitfall #3: The Big Bang approach to OKR rollouts
OKRs involve change management — you're asking everyone to operate in a new way. But while managers may view change as an opportunity to strengthen the business, teams may view it as disruptive and intrusive.
“Everything, everywhere, all at once” OKR scenario
Marcus, a department head, learns about OKRs and thinks it'd be great for his teams to adopt them. He meets with the executive team, gets buy-in, and starts a company-wide OKR rollout, but doesn’t consider how this change will affect employees.
During this time, his company is working towards a big seasonal event — everyone is heads down and focused. While Marcus has a great rapport with his teams, they think the OKR initiative is a distraction and ignore it. It seems like a fine idea, but it’s not a priority because everyone’s focusing on a demanding project.
No one engages or connects with the purpose of OKRs, and Marcus’s implementation fizzles out.
"You really need to assess the environment before introducing some kind of massive change. If your organization is already going through something big, it may not be the best moment to introduce OKRs."
– Lucas Gauzzi
A better way
Keep context in mind and approach your OKR initiative incrementally.
You may get excited when you see positive results from a proof of concept. But concepts may fail to show you the planning, consideration, and timing it takes to see OKRs succeed.
Refrain from doing too much, too fast, especially without team buy-in. Forceful adoption will yield lackluster engagement — you need to connect people with the purpose behind OKRs.
Avoiding the Big Bang approach involves doing your due diligence, for the methodology and your teams.
- Why OKRs?
- Why roll out now?
- Why not later?
- How will we track our progress?
- How do we define success? Be specific.
Secure executive buy-in
Have senior leaders review your plan. Show them what change looks like. Explain the steps you'll take to ensure success. Get an executive sponsor to support the program actively.
Start with a proof of concept
Begin with senior leadership, a pilot department, or pilot team. Educate and train. Have the right advisors and coaches on board. Celebrate wins and develop internal case studies. Recruit knowledge replicas (i.e., OKR Champions and Ambassadors) to help drive change.
Simplify and scale up
Bake OKRs into existing meetings and rituals. Make sure to review, discuss, and track for impact. Expand to more teams and departments gradually. Each group will need about three cycles. Expect to tweak and learn as you go.
Pitfall #4: Assuming OKRs are easy
OKRs are deceptively simple in concept, but not easy to execute. When you first hear about them, you think, "This is so obvious. Of course." But when you implement OKRs with your teams, you realize they take committed effort, clear guidelines, and ongoing adjustment.
“Tunnel vision” OKR scenario
Dara, an engineering lead, completes her OKR training and is prepared to develop OKRs with her team. She sets up OKR creation sessions for team and individual OKRs.
Everyone feels good about their OKRs but didn't have anyone review or challenge them.
Once the OKR cycle starts, Dara and her team realize their mistake — they made OARs, objectives and all results. Many key results were tasks. Unexpected projects distract her team from making meaningful progress. They find it difficult to execute, deliver, and measure results.
"The biggest mistake is feeling a need to include everyone and everything and they lose the heart of the OKRs. They dilute their outcomes and create a cumbersome structure that does not lead to increased performance."
– Christine Stone
A better way
Invest in a review system or OKR advisory, whether internal or external — this ensures OKRs are not defined in isolation.
Remember, OKRs aren’t where you cram all your work. The idea is to identify areas for focused improvement in the near term. Coaches can help people get unstuck through education, organization, and communication.
There are no hard and fast rules to OKRs. It’s on your organization to create and adjust your own solutions. Here's how:
- Iterate: Hold special meetings for the first nine months to work on your OKR solution. Assess interactions, track OKR achievement, identify trends or abnormalities, and make changes until the system runs smoothly.
- Learn: Engage professional consultants or OKR coaches with experience in your culture, values, or metrics maturity, but don’t assume they have to be industry/function experts.
- Adapt: Get feedback from participants about OKRs and how they fit into your daily operations. Identify areas for improvement and refine your OKR program to align with your organization's goals and values.
Pitfall #5: Lack of investment in change management
Data-to-insights teams’ work must connect to what business teams need to know. That connection requires a focused investment of resources in data analytics. But the investment in culture change, which is just as (if not more) important, is not keeping up in organizations.
“What really matters” OKR scenario
Julie, a data and analytics leader, submits her budget request for the year — increase data investment. Her goal: less data in outdated and siloed legacy environments and more in cloud-based environments.
Her COO, Soo, asks how this increased investment translates into business value.
Julie's focus is operational — products, AI and ML, quality and security, and managing architectures. She thinks, “Am I responsible for data literacy and consumption too?”
Soo explains, "If we are not delivering business value in some measurable form, what have we accomplished?"
“Outside OKR expertise can help build an effective OKR program, changing ways of working that require true, two-way collaboration between business and data analytics team members.”
– Cinny Little
A better way
In a 2022 survey of data and analytics leaders, 88% of organizations reported increased data investment. But 80% viewed cultural factors as the key blockers to driving business value from data investments.
The culture, people, processes, and organizational systems — not technology — are the main challenge to being data-driven. The cost of measurement needs to be lowered to create accessible data.
Employees need skills like data literacy, while leaders are challenged with aligning teams. Between everyone, communication capabilities must evolve to drive lasting results.
Get started, then get bigger. Some teams need to see what a good OKR is before they can create that mental adaptation.
Here are two approaches for starting small:
The "what’s going on” approach
Work with a data analytics leader to determine which actions are being taken through daily dashboards or reports. If you have no idea, dig into that. A business decision-maker can help with what these dashboards or reports should include.
If data isn’t available, create an OKR on gathering the data needed for your objective (if it makes sense from a timing and budget standpoint).
The “key stressor” approach
Learn what business decision-makers are worried about and the metrics to show progress. Work collaboratively on one or two objectives, tying insights from current data.
If this isn’t possible, create an OKR describing the work needed to gather the data. Be sure to specify the timing and identify agreed-upon deliverables.
Pitfall #6: Doing too little or too much
Don't set and forget OKRs. Reviewing OKRs infrequently or irregularly can lead to this.
OKRs must be integrated into weekly work to be effective. In contrast, OKR programs can become over-engineered. There should be a balance between focusing on the process and reaping its benefits.
“Practice what we preach” OKR scenario
Rosa spends a week crafting OKRs with her department leaders and OKR champion. Her company’s OKR program executive sponsor, Naya, wants more department involvement in OKRs this quarter and for everyone to shift from an output to outcome mentality.
Naya: “You don’t seem convinced that OKRs are helpful.”
Rosa: "I'm concerned about why this matters if the teams were productive. We have a roadmap. Everyone on my team works in sprints. Why do we need OKRs?”
Naya: “I've noticed we're working in silos. Yes, your team ships, but sales has voiced that they’re struggling to sell what you're developing, and we likely won't hit our revenue targets. When was the last time your team talked to another department or spoke with a customer?"
Rosa: "I... don't remember."
Naya: “So here’s an opportunity. OKRs are supposed to help us with this. We need a common language to describe what success looks like.”
Rosa: “But, no one creates cross-functional OKRs here or reviews OKRs during the cycle, which I believe the executive team should do with company OKRs, for example. If we care so much about adopting them, shouldn't we all review them regularly?”
Naya: “You’re right, we should, Rosa. Let's discuss creating cross-functional OKRs and defining a regular cadence for OKR review. If I send over a doc, will you help me?”
Rosa: “No problem.”
“A successful OKR system follows a simple equation: maintaining the system costs less than the benefits the individual gains from using the system. If updating OKRs takes more time for less-than-expected benefits, the system is likely to fail. The inverse is also true.”
– Brett Knowles
The better way
OKRs won’t magically fix your management debt. You must hold regular 1:1s, coach, provide behavior-based feedback, and delegate to build your management capability. Remember, you're creating a culture of continuous learning.
With the right people in the right roles, maintaining an OKR cadence and OKR-based discussions is easier. By following a standard solution for tracking OKRs (like software), everyone easily accesses and refers to the same information.
Managing OKRs effectively requires ongoing meetings — in 15 minutes, you can do a single team check-in with 1-3 OKRs. Teams new to the process or having disagreements on how to operate might need more time.
With each key result, every 1-2 weeks, follow the acronym MRBIRDS:
- Measure current confidence
- Record everything and share it
- Brainstorm actions to improve confidence
- Include current key result values
- Review last week’s confidence, narrative, and actions
- Discuss what’s happened since the last check-in
- Share blockers and challenges
If you have multiple teams working with OKRs, facilitate a mid-cycle OKR review. This review doesn’t have to be a line-by-line of your OKRs, but encourage each team to share at least two OKRs with the group — one that’s on track and one that isn't. This enables pausing for celebration and reflecting on learnings.
Pitfall #7: Trying to force everything to fit
An organization measures its most important work with KPIs, where OKRs cause changes in KPIs. Unfortunately, sometimes existing KPI Scorecards are re-titled as OKRs, or OKRs are to-do lists packaged in a new form.
“OKRs may be seen as a writing exercise, but the framework is meant to change the way we think.”
– Vidhya Parvathy
“The tsunami” OKR scenario
Brenna, a CTO, is concerned about her team being flooded with an endless backlog. To ensure everyone focuses on delivering value, she introduces OKRs.
She then shares her seven engineering OKRs with leadership, who takes this new change as “everyone must have an OKR” — soon, their organization of 250 people has 1,000+ OKRs on the same spreadsheet.
Some objectives have nearly 20 key results, and most of them are just projects. Brenna can’t understand how a simple methodology got so bloated.
I would audit all OKRs "in flight" to evaluate how well the program is following the framework. Use it to tighten things up and see which teams need extra support. If 25 milestones are listed as a key result, this is a red flag — more rigor needs to be placed on defining outcome-based key results versus rebranding tasks/actions/milestones.
– Natalie Webb
The better way
Often, OKRs reveal organizational gaps. Rather than blaming the methodology, find the core issues and adjust accordingly. It can take a few cycles for OKRs to click, so it’s important to give your OKR implementation time to succeed.
Additionally, engage stakeholders and gather feedback. Empathy can help manage pain points and disbelief. With time, OKRs should become an unconscious habit — the key to success is not overselling the framework.
Do it right from the beginning. You don't start an OKR program by creating OKRs. So before you roll out any OKR programming, define your "rules of engagement" after defining your why.
Ben Lamorte calls these universal OKR parameters:
- At what level will we set OKRs? (e.g., company, team, individual)
- How many OKRs will we set? How will we balance internal and external objectives?
- How will we score OKRs and update our progress?
- How long is an OKRs cycle? (e.g., annually, quarterly, etc.)
- What are the three types of key results? Are milestones appropriate?
- Where are we going to draft, publish, and track OKRs?
- How will OKRs relate to performance reviews?
- How are OKRs different from KPIs?
- How will we ensure OKRs align?
- How will we ensure that most OKRs originate “bottoms-up?”
Be prepared to iterate, because finetuning an OKR program takes time.
Preventing OKR program failure
By learning from what works and what doesn’t, you’ll eventually develop a successful OKR solution. But you don’t need to go it alone or rely on trial and error alone!
Whether you’re new to OKRs or a seasoned pro, the Dreams with Deadlines community is where you’ll find the knowledge, connections, and resources you need to achieve your goals with greater confidence, efficiency and impact.
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Dreams with Deadlines is the one and only strategy meets execution community. We’re a global network of ambitious leaders who are passionate about using OKRs and agile practices to achieve audacious goals and build a better future.
Whether you’re new to OKRs or a seasoned pro, the Dreams with Deadlines community is where you’ll find the knowledge, connections, and resources you need to achieve your goals with greater confidence, efficiency, and impact.