How To Prepare Your Leadership For Implementing OKRs Successfully

What impact will Implementing OKRs have on leadership teams? This article details the challenges and practice advice for overcoming them.

25 August 2020

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OKR Implementation; issues

In part I of this series, we discussed some of the broad systemic challenges faced by implementing OKRs. Here we will go into more detail about the types of challenges you may meet at both senior and junior levels of leadership and some approaches to dealing with them.

Some of these will seem obvious, and indeed they are. Many are not specific to implementing OKRs and would apply to any large change or transformation, but that doesn’t make them any less relevant to preparing your organisation for OKRs and so we’ll cover them here.

All people preparation broadly falls into solving two types of issues:

a) mitigating negative attitudes and behaviours; and

b) ensuring the right support and expertise is available so that people can do what they need to do correctly and confidently.

Leadership are the individuals who will live and breathe OKRs as they are implemented and after when the system is up and running.

If you wish to see the benefits of improved agility within your organisation through OKRs, these leaders are the ones making it happen.

They will be making the brave decisions or empowering others to do so; they are also the ones that need to provide the clearest intent and strategic vision through OKRs.

To ensure your leaders take up OKRs well, you will need to think about the potential challenges we’ll discuss below and address them if necessary.

Whether you’re implementing OKRs yourself or you bring in experts (which can make things substantially easier), these issues can’t be ignored if they are present.

Senior Leadership 

When we talk about senior leadership, we are talking about leaders within your organisation that are responsible for large chunks of it and will be leading other leaders.

As an example, “Heads of” and above are the sort of people to whom we are referring. The following sections deal with issues you may meet in your senior leadership when implementing OKRs.

Not having buy-in

Your first problem may be that your fellow leaders just don’t see the need for a new way of managing business performance.

Prior investment in structure, communication systems, processes and policies can lead to resistance, both active and passive, as people are unwilling to invest in a new system.

This is obviously not unique to OKRs and is a standard buy-in issue you have probably faced many times. You want your fellow and subordinate leaders to drive this as much as you, so ideally you want them to really feel the need and see how OKRs solve that need.

Basically, they need to go on a rapid version of their own journey, see what you see and want OKRs.

The key here is to develop a shared understanding of why the current system is not fit for its purpose. Evidence the problems with supporting data (ideally with magnitudes to avoid arguments about “how big a problem is that really?”).

So, we’re talking clear and simple problem statements, linked to the organisational objectives if possible, and clear explanations of how OKRs solve those problems.

Don’t feel uncomfortable about trying to get buy-in from leaders below you in the hierarchy. It’s one thing to implement something by directive, but you’ll always get better results if those doing it have really bought into what they’re doing and why.

Another approach here is to challenge a potentially resistant leadership to provide you with the answers and alternatives to solving the problems you have highlighted.

It may be OKRs are not the answer for you and empowering your leadership to solve the problems their way would reduce the buy-in issues we are discussing. They may surprise you and come back with OKRs as the answer.


Sometimes it’s hard for people to see the value that a new idea will deliver, and despite what you think is clear evidence and persuasive argument, certain people just won’t get on board.

For these circumstances, the leapfrog approach can be useful, allowing you to demonstrate the value directly. It is common when implementing OKRs to do so incrementally, with some organisational level being the smallest implementation group (e.g. a particular department).

Choose one where the chance of success is high, but where there are problems to be solved and the value realised is demonstrable. This also gives time for people to adjust to the new reality, while you tout a success story as quickly as possible.

Nothing breeds success like success!

Bad Prior Experiences

Bad previous experiences can sour a person’s taste for a particular idea and set them against it in all cases. It’s a bit of a cliché that a bad implementation destroys the reputation of a technology or idea, but it’s very true.

Individuals who’ve had bad OKR implementations dumped on them in the past or have been party to implementing OKRs poorly may be reluctant to go there again.

This change is necessary, so the individual needs to understand it’s going to happen, and their best option is to help ensure it doesn’t fail like their previous experience.

The ideal solution for you is to bring their experience to bear to help ensure you don’t suffer the same issues in your implementation.

Actively involve them in the process and improve your probability of success at the same time.

Leadership Style Issues

Unfortunately, you can find yourself in a situation where you have leaders who have fallen into bad habits. These can include those who create power bases by tightly controlling communications and constraining autonomy in their areas.

The implementation of a system like OKRs with the inherent implication of high autonomy levels and open flows of information on performance can run against the perceived interests and style of such managers.

Intent-based leadership isn’t natural to everyone, and there is a significant tranche of managers who are very suspicious of it.

This is a huge topic, and the solutions for these behaviours are personal and usually require coaching to remedy.

Sometimes individuals exhibiting these behaviours are relatively easy to bring along, and sometimes it is a lot more challenging. Unfortunately, these types of solutions are beyond the scope of this article.

Our guidance in this situation is to be aware and, as far as possible, try to mitigate the behaviours you are expecting to see when implementing OKRs.

What should you expect to see?

Here are a few pointers around how the implementation itself should be done that might be helpful with this type of issue. They are also good practice in any case!

  • Ensure the system is implemented with a set of guiding principles on how to use the framework. These principles should guide everyone in the correct use of the system and so will help prevent corruption/undermining of it by deliberate misuse. With this in place, such misuse should be visible and obvious to everyone. Again, this is good practice and will help ensure that the system runs smoothly as it should also protect it from inadvertent misuse.
  • Ensure clear monitoring of time invested in the implementation process and degree of team involvement. Bake this into the feedback of the implementation metrics. This will help identify early on any leaders that will procrastinate and fail to provide the level of investment into the process or the level of collaboration needed for success.
  • Create a feedback loop with your teams to assess how well supported they felt by leadership whilst implementing OKRs.
  • Consider using OKRs as the mechanism for defining and measuring the success of your OKR implementation. It’s a little recursive, but we’ve seen this done very effectively.


Dysfunction exists to some degree in all areas of all organisations. The scale of the dysfunction and the degree to which the business has tolerated it will have a direct bearing on any resistance to the implementation by leaders of dysfunctional areas.

When it becomes clear that OKRs will surface and draw attention to the dysfunction in an area, it can feel like a direct threat to the responsible leader.

It also means that facing into the problem will require the leader to expose a level of vulnerability that is likely missing (or the dysfunction would probably have been highlighted and tackled before).

As OKRs kick in, it will create a degree of discomfort across all levels of the dysfunctional area. If this is the case, you may want to change the perception here from one of threat to one of opportunity.

Ensure it is well known that OKRs make performance inherently transparent and that it will show up poorly performing areas, processes and functions.

Make it clear that there is an expectation of this and that there will be no retrospective penalties (excepting formal policy and legal implications), but that there will be a mechanism to address and support these situations where they arise.

You want your leaders in areas that are struggling to see this as an opportunity to highlight how they are struggling and get the support and make the changes they need to become successful again.

Critically, you will want to use this as an opportunity to bring struggling leaders up to scratch with additional support and coaching.

Senior Leadership Summary

To summarise the approach to preparing senior leadership for implementing OKRs:

  1. Get buy-in as widely as possible: evidence the problems and show how OKRs solve them. 
  2. Persuade sceptics as early as possible: demonstrate the value in the initial implementation phase. 
  3. Turn bad previous experiences into value mines by involving those individuals in the implementation if possible. 
  4. Be aware of leadership styles that are incompatible with intent-based leadership and have a plan to mitigate. 
  5. Set the tone right for dysfunction: you expect to uncover it and OKRs are an opportunity for areas of the organisation that have been struggling to get extra support and make changes. 

We also advise your team to read the following three articles:

  1. Your Mission Is To Produce Outcomes, Not Outputs
  2. Cascading OKRs at scale: How do you avoid the slow waterfall of goals?
  3. 8 Ways To Lead Employees With Intent-Based Leadership

 All Leadership 

If you’ve analysed your senior leadership carefully and got the potential leadership obstacles all flagged and mitigations in place for them, then you need to consider what all leaders in your organisation are going to need as a matter of course to get the implementation done successfully.

Fortunately, this is quite simple to articulate. Every leader in your organisation needs to:

Understand what OKRs are and how they work

Meaning that they genuinely understand OKRs, such that they can explain them to others with confidence.

Commanding a good understanding of OKRs will mean that nobody in the organisation with questions needs to go far for an answer, and everyone will be able to focus, with a common understanding and language.

This is best ensured through basic but consistent training, given to all leaders.

Access to expert support

For when people are unsure about the practicalities of what they are doing, especially as it's likely to be the first time most of your leaders are using OKRs.

This is particularly important while they are crafting their first set of OKRs. The distinction between creating good and bad OKRs is critical. OKRs are there to drive the right behaviours and work, but they must be of good quality to do that.

Setting the tone early on will lead the way for the future and can make or break the usefulness of OKRs to the organisation.

Top-level leadership to have its ducks in a line

If senior leadership are not ready with a good quality starting point for the organisation to derive from, then the whole enterprise is pretty much doomed from the start.

So, in practice, we’re talking here about good quality organisational OKRs, documented and ready to communicate before the rest of the organisation is asked to do theirs.

Again, senior leadership set the tone here. If you want this to work, you need to make sure that they are ready and doing the right thing!

If you deal with these considerations it will mean that an implementation will likely go smoothly and will continue to live on in a form that is sustainable and adaptable for the foreseeable future.

It’s important that knowledge is not lost over time, so a plan should be in place to ensure that new leaders coming into the organisation are given the right training and practice to perpetuate what those who went through implementation have put in place.

This should be planned for and be in place from the start!


This covers some basic considerations that are needed for leadership in implementing OKRs successfully.

OKRs are not just for leadership though, and in the next article in this series we’ll take a look at what’s needed for all your people to prepare themselves for OKRs and ensure they are engaged with the process and benefiting from it.

In part III of this series we look at how to prepare your people for OKRs, the types of challenges you face as you do this and some suggestions for how to mitigate these.

If you would like to discuss planning and executing an OKR implementation please read about our OKR Adoption & Implementation service or why not book a 25-minute consultation with one of our OKR Practitioners.

Mike Horwath

About the author

Mike Horwath

Mike is the Co-Founder and Co-CEO of 1ovmany. He is also the Co-Author of The OKR Method a Strategy & OKR Expert and at times an Executive Business Transformation Coach.

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