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Overcoming Troubles of Implementing OKRs

Updated: Mar 17

My top reasons for why OKRs fail;



I make no bones about the fact that I love Objectives and Key Results (OKRs), and champion them as a tool for change. They are, in my opinion, awesome tools for projects and organisations that seek to implement change.


I’ve used them to great effect several times now.


But that is not how my first rollout of OKRs went.


Not at all.


My introduction to OKRs was through a recommendation from a senior manager (who then promptly exited the organisation, taking his support with him). A couple of us had warmed quickly to the concept and devoured videos, books and discussions, attempting to absorb the enthusiasm and learnings of others.


When it came to launch, we looked to the official ‘OKR’ way and tried to apply it like zealots from day one, seeking to convert the rest of the management team to our newly found secret to success.


Big mistake.


I'll dig into why in a moment, but I winged it as best I could and searched for answers to my questions about implementation, which seemed pretty fundamental, but I was disappointed not to be able to find the guidance I desperately needed.


So, here it is. How I suggest overcoming troubles of implementing OKRs.


What are OKRs?


Noob eh? Ok, no problem; here is a quick summary:


OKR stands for Objectives and Key Results.


It's a framework popularised by Google that thousands of organisations now use to define and track objectives alongside measurable ‘key results’ needed to achieve them.


The objective is the overall goal, while key results are specific, quantifiable metrics that gauge progress.


Here’s an example;


Objective: Increase customer retention in Q4.


Key Results:

  1. Reduce customer churn rate by 15%.

  2. Increase customer satisfaction scores to at least 90%.

  3. Implement a loyalty programme with a 25% adoption rate among existing customers.


The objective sets a clear goal, and the key results offer specific, measurable targets to gauge progress.


I’ve written more about what OKRs are here, and here.


Problems With OKR Implementation


Overcomplication of OKRs


OKRs are simplicity itself. They are designed to be easy to communicate, understand and implement.


Let’s take a look at the typical cycle, which comes from Whatmatters.com

A summary of the typical OKR cycle

Here, you’ll see the nested, quarterly approach to OKRs, with Annual OKRs setting activities kicking it all off.


Within each quarter, you have company-wide OKRs, Team OKRs, and Employee OKRs.


That is a LOT of objective setting and alignment in a short period. Most organisations are going to struggle with implementing that many objectives throughout an organisation annually, let alone quarterly.


If you’re not careful, all anyone feels they are doing is setting objectives, and you might not agree on them before you even exit the quarter. Certainly, that is what happened to us.


We (as a management team) got tied in knots trying to agree and align on OKRs. There were constant iterations and reviews of objectives at every level, and frankly, a lot of resistance to committing to stretch targets. And we had consciously chosen not to implement employee OKRs at that point.


Now, I’m not saying it can’t be done, and I’m not saying it shouldn’t be done. I recognise that OKRs are a top-down and bottom-up method so that you can simultaneously set key results at the company and the employee levels, adjusting as they meet in the middle.


What I am saying is that if I went back to square one to implement OKRs all over again, I’d keep it as simple as possible for the first quarter; just one set of objectives at the highest level, with ownership of the key results clearly defined.


To clarify; if I’m working with a department, I focus on the OKRs for the department, each with a team lead taking ownership of key results. If I’m working at a company level, I’d set them only at the company level at that point, and each key result would be assigned to a department. For the first few cycles, I would keep it simple and go no deeper than that.


People need to get used to the system. The leadership need to learn how to communicate. Everyone needs to learn how to write and measure OKRs robustly. Doing it at multiple levels in the organisation on day one is a recipe for failure.


That said, it’s never an entirely smooth process, nor should it be.


So, in order to maintain simplicity, we should look for the things we aren’t going to do, not to add things in, which leads us to two key questions.


Should We Set Annual OKRs?


Yes, but cadence (quarterly, yearly, etc) depends upon your circumstances.


In 2019, Google broke the conventional wisdom and started to focus on annual rather than quarterly OKR setting but looked for quarterly progress reports instead.


CEO Sundar Pichai saw the quarterly process as potentially too short and onerous. And that’s okay for an organisation like Google that is well embedded and thinks strategically many years ahead. Still, it might not be right for a smaller startup organisation or an organisation in a difficult situation where it needs to pivot and adapt a lot to changing circumstances. In these cases, I’d focus on the quarterly objectives.


But the truth is, as John Doerr says in his OKR bible Measure What Matters, the organisation should define the cadence.


Should We Abandon Quarterly OKRs?


No. And Yes. Use whatever works for your circumstances. If a lot of short-term action is needed, I would set them quarterly to build momentum.


In my most recent use of OKRs, I’ve set annual objectives but quarterly key results.


Here’s an example;

An example of an Annual OKR objective but quarterly key results

So, here's I've set an annual objective to target £3.5 NNARR, but backed it up with 4 key results just for Q1. As Q2 approaches, then I'd keep the objective, but update the key results.


Not having the right tools for visibility and tracking


The enduring saying, "the right tool for the right job," holds particular significance when managing OKRs.


While Jira is a stalwart in the software development and task management realms, its intricacies make it less than ideal for those unfamiliar with its specific features, particularly in the context of OKR management.


Spreadsheets are another commonly used tool for OKR tracking. While cost-effective and straightforward, they can quickly become unwieldy as you attempt to add layers of complexity—such as detailed notes, comments, or tags.


Although real-time


collaboration is possible in spreadsheets, it often feels tacked on rather than seamlessly integrated. However, for those on a limited budget, spreadsheets can be a practical, albeit not optimal, solution.


Many cloud-based tools can do the job well. And effectively, they only need to do a few things;


  • Allow for parent & child task management (or sub-tasks); The parent is the objective, and the children are the key results.

  • Assign ownership

  • Track progress

  • Give visibility to all


In my experience, Monday.com is a user-friendly platform designed explicitly for project and objective management (disclaimer: no affiliation). Its features range from status updates and document linking to the tagging of objectives and key results, making it a robust choice for OKR tracking. The low learning curve further increases its appeal, particularly for those less technically inclined.

Monday.com example of OKRs

An example screenshot from Monday.com - For more see this article.


Other worthy contenders in this space include Asana and Trello, which offer varying degrees of customization and integration capabilities.


Trello's card-based interface offers a more visual approach.


An example of Trello OKRs

Asana provides excellent project management features that can be adapted for OKR tracking.


An example of Asan OKRs

Then there's ClickUp, which provides a comprehensive suite of productivity tools that can be customised to suit your specific OKR needs.

An example of Clickup OKR

The crux of successful OKR implementation, regardless of your tool choice, lies in transparency.


Ensure that the platform you select fosters visibility among all team members.


OKRs should not be viewed as mere bureaucratic formalities; they should serve as the navigational compass for projects and strategic deliveries. As such, they should be front and centre in team meetings, updates, and strategic dialogues, effectively becoming ingrained in your operational DNA.


By judiciously selecting the right tool and committing to complete transparency, you lay the groundwork for a team that is not just engaged and informed but also considerably more productive.


Lack of Managerial Support and Buy-in


When I first dipped my toes into the OKR pond, a handful of us were brimming with enthusiasm but faced a void in terms of managerial endorsement.


This absence of top-down support relegated us to the role of OKR evangelists within the organisation. We were fervent in our advocacy, climbing proverbial soapboxes to proclaim the virtues of the "OKR methodology." We led educational sessions, distributed copies of the seminal book "Measure What Matters," and even went the extra mile to develop comprehensive training guides. However, ingraining OKRs into the organisational fabric proved elusive.


Now, allow me to transition into a closely related issue—what I term the "watering-down" of OKRs. The tepid commitment from our senior leaders was a significant roadblock. Their ambivalence, whether overt or subtle, set a tone that dampened wider organisational uptake. It was only when the CEO finally took the reins, visibly endorsing and participating in the OKR process, that the broader team began to take the initiative seriously.


Based on my experience, OKR success is closely tied to unequivocal, top-down support from senior management.


This isn't just about token nods of approval; it's about active engagement in every phase of the OKR cycle—from rigorous critique during the initial setting of objectives and key results to ongoing, diligent progress monitoring. When senior leaders provide that level of comprehensive involvement, it acts as a catalyst, setting the stage for an organisational culture that accepts and thrives on OKRs.


Therefore, if you find yourself mired in an OKR initiative that lacks managerial support, consider this a critical action item. Address it head-on with your leadership team. Advocate for their active participation, stressing that OKRs aren't just another fad but a strategic tool capable of driving measurable improvements across the board.


When you've secured unequivocal backing from the top echelons of your organisation, you've effectively cleared one of the most formidable hurdles in successful OKR implementation: resistance.


Mutation of the OKR Method


In our initial zeal to secure buy-in for the OKR approach, we—the self-appointed evangelists—began to make considerable concessions that led to a significant dilution of the methodology's core principles.


To appease key stakeholders, we allowed a level of mutation to the OKR framework that was not just suboptimal but counterproductive. The result was a version of OKRs that was anything but streamlined.


Issues included;


  • Too many objectives and key results. Always try to aim for 3 to 5 of each.

  • Poorly worded OKRs that deliberately allowed people to be noncommittal about deliveries.

  • OKRs that teams didn’t buy into, but had thrust upon them.


What we ended up with were OKRs that were bloated and cumbersome, burdened by an excessive number of objectives that rendered the entire system unwieldy.


This was contrary to the essence of OKRs, which are intended to be concise, focused, and actionable. The excess baggage we added to placate stakeholders made it increasingly difficult to track progress, much less achieve the objectives meaningfully.


This raises a crucial point: the temptation to alter the OKR method to fit pre-existing notions or appease various factions can be a slippery slope. Such dilutions, while perhaps well-intentioned, often result in a Frankenstein's monster of a system that serves neither the team nor the broader organisational goals effectively.


The compromises we made, thinking we were gaining ground, actually undermined the very objectives we aimed to achieve.


Therefore, it’s essential to be vigilant about maintaining the integrity of the OKR framework.


I should have pushed harder in the early days for an external OKR coach. They didn’t have to be great, nor time-consuming, but someone who had more experience and objectivity could have helped guide us much better than the blind leading the blind scenario that we ended in.


Education and advocacy play a vital role. One must not only introduce the methodology but also equip the team with the understanding and tools to implement it effectively. This includes pushing back against unwarranted modifications that compromise its efficacy.


Furthermore, it underscores the need for clear guidelines and ongoing training. As the methodology gains traction within your organisation, it’s imperative to continually reassess and recalibrate to ensure that the original tenets of OKRs are upheld.


In Summary: Overcoming Troubles of Implementing OKRS


  • Heed the advice of someone who's felt the heat yet remains an ardent advocate: OKRs are an invaluable tool. They've fundamentally changed the way I approach objectives, and though I wouldn’t say the road has been entirely smooth, there are certain lessons I wish I'd grasped sooner.

  • Firstly, simplicity is key. Tailor the OKR cadence to match your organisation's rhythm, but don't let them become a cumbersome chore. Choose an appropriate tool for tracking that aligns with your team's capabilities and workflow—this is more crucial than you might initially think.

  • Secondly, even the best-laid OKRs can flounder without robust support from senior leadership. Top-down enthusiasm and engagement are not just desirable; they're essential for the OKRs to make a meaningful impact.

  • Lastly, while customising the OKR framework to fit your needs can be beneficial, exercise caution. Make sure any modifications enhance, not undermine, the fundamental goals you're striving to achieve.

  • By approaching OKRs with these guidelines, you're setting yourself up for a more streamlined, focused, and, ultimately, more successful journey towards reaching your organisational objectives.


Good luck!


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About the author

Hi, I'm Alan, and have been working within the IT sector for over 30 years.

For the last 15 years, I've focused on IT Governance, Information Security, Projects and Service Management across various styles of organisations and markets.

I hold a degree in Information Systems, ITIL Expert certificate, PRINCE2 Practitioner and CISMP (Information Security Management).

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