A Guide to Optimize Your OKR Planning

If your company or team works with OKRs you may have noticed that people start to act a little bit differently towards the end of a quarter. 🤔 I picked up on this and it made me incredibly stressed each time I saw the end of a quarter approaching. I used to not be that experienced when it came to OKRs. Planning seems to be the most stressful time for companies and Product Managers, next to the day-to-day business.

Over time, I’ve learned that a bit of farsightedness and recognizing the patterns of the OKR planning process can help to solve some issues. That’s why I’d like to share a detailed step-by-step process around OKRs with you. 

By the way: I already gave an introduction to OKRs in my previous article. In case you want to catch up, you can read more here: 5 best practices to make your OKRs awesome

Before I dive into things, let me share some background with you about the whole process. In some organizations, not every team plans OKRs in the same way. The following case is (intentionally) a complicated one, that requires a lot of alignment between teams and departments. If your company structure or team is less complicated: Great! You can just cherry-pick the parts you like the most. 😉

Simplified Example/Case:

Company Information: 

• Name: Unicorn Inc.

• Multi-Product company

• Core Markets: USA, China, India

• Number of employees: 1000 (worldwide)

Hierarchy & Team Structure: 

• Core Leadership Team: 5 people

• Extended Leadership Team: 30 (10 people per core market)

• Departments + Teams: 90 Teams with ø10 people

  • 20% of the teams are Product & Engineering

The Core Leadership team plans the (high-level) company OKRs. Each core market sets individual goals as well (these are related to the company OKRs as well as being market-relevant OKRs). On top of that, all teams define their OKRs which support the company OKRs. Undoubtedly, every team and product has an individual roadmap which will be reflected in the team OKRs.

Note: The upcoming planning timeframes I’ll define are based on my own experiences. Feel free to use it as a template and adjust it to your own needs.

The OKR Planning Process Overview (5 Steps)

Note: This whole process is focused on team OKRs. Personal OKR planning is excluded.

There have been many occasions where I’ve seen OKR planning finished at the end of the first month. That’s obviously way too late. A good process can help you ensure you finish planning “on time” so you can kick things off with well-aligned and designed OKRs in the next quarter.

In three to four iterations, teams should be able to fully define their OKRs. Next, I’ll do a deep dive into each of these iterations and share some best practices and agendas you can reuse.

#1 Creating Your First OKR Draft as an Engineering Team

Firstly: Teams create a draft without exactly knowing whether the previous OKRs will be all achieved or not. If you foresee some objectives not being achieved, you can already prioritize them in the draft.

The goal of this session is to look into the next quarter with your team. What will be a high priority? What needs to be fixed? What do our customers want, what is the market demanding? Every team on every level needs to create their first proposal, taking into consideration that things from the previous quarter may slip into the next one as well. Consider renting a conference room in a nice place outside the office and doing a 2-3 day workshop to review previous OKRs and define new ones. And, of course, combine the whole thing with fun outdoor activities. 😉 This will all depend on your company size as well as budgeting plans, but for the most part, Engineering teams can either plan for the next quarter offsite or onsite.

Here’s an overview of how to get started:

Meeting Owner/Facilitator: Product Manager or Team Lead

Attendees: Team + eventually 1-2 key stakeholders

Meeting duration: 1.5 hours (can be more or less depending on the team)

To-Dos:

1. Create a new OKR slide or confluence page + share it with the team (invite people to add suggestions)

2. Send the invite to the team one week in advance

3. Ask attendees to prepare and come up with suggestions for the next quarter

Agenda & Outcomes:

1. Review the document & ideas (Team discussion)

2. Decide on priorities (Team decision)

3. Write them down 

Note: The Product Manager or Team Lead is just a suggestion for facilitating the meeting. Any selected team member can schedule and drive the OKR planning.

#2 Creating Your First OKR Draft as a Leadership Team

The goal of this meeting or offsite is to sit together as a Leadership team and discuss the priorities for the next quarter, taking previous OKRs into consideration. In my previous job, Leadership teams always had offsites for quarterly planning. I’ve learned that too many people at an offsite makes teams unproductive. Choose who should and shouldn’t be a part of it wisely. Make sure every team has at least one representative.

Meeting Owner/Driver: Team/Tribe/Chapter Lead

Attendees: Team Leads & Product Managers

Meeting duration: 2 hours (can be more or less depending on the team and scope) 

To-Dos:

Create a new OKR slide or confluence page + share it with the team (invite people to add suggestions)

1. Invite the team two weeks in advance

2. Preparing a status update for the current OKRs

3. Ask attendees to prepare and come up with suggestions for the next quarter

Agenda/Process proposal:

1. Each member writes down priorities/ideas on sticky notes (Objectives + some Key Results) 

2. Present/pitch ideas in front of the group (no discussions, pitch only)

3. Review and discuss priorities (Team/Tribe/Chapter Lead + Leadership team)

4. Team voting on priorities (everyone has 3 votes) 

5. Final review of high-level priorities 

Note: Depending on how your company is organized, you can either do the Leadership OKR planning as the very first team (to lead the way), or you can do it in parallel with other teams. You can go even crazier and let the teams start and let them set the direction.

#3 Sharing and Adjusting OKR With Stakeholders

Before the OKRs are shared with the whole company, you need to start with your key stakeholders. Some teams have more and some have fewer dependencies on others. If your company is, for example, structured based on value streams (like Spotify), squads will very likely present their OKRs to the whole tribe to make sure all teams in that value stream are aligned.

It’s very important as the “driver” of the OKR definition to follow up with key stakeholders, share the feedback back to your team, and adjust if needed. How you do that is entirely up to you. I was always a fan of scheduling a feedback session with one or two representatives of my team.

It might sound obvious but I love mentioning it regardless:

This session is to get feedback from your key stakeholders. It’s not about making decisions and changing everything. As a Product Manager or a Leader, it’s especially important to listen to the feedback and bring it back to the team so that everyone gets the bigger picture.

#4 Review and Retrospect on the Current Quarter

After aligning and adjusting the OKR draft, you’re very well prepared for the final phase. As you come to the end of the month and quarter, it’s time to review the outcomes and to retrospect.

The Methodology to Review Your OKRs 

Ideally, the OKR review meeting should be scheduled by the OKR driver, whoever this may be. I recommend blocking an hour with your team to review each objective and the key results. The best time, in my opinion, was always the last week of the quarter. Alternatively, you can do it in the first week of the next quarter.

There are many ways you can measure the OKR achievements. If you’ve done a great job defining OKRs you know that the objective has been achieved if all the key results have been achieved as well.

What if they haven’t been? 🤔

In that case, my teams and I always kept it simple. We rated the key results and objectives on a percentage level from 0-100% with a color code:

• Green = 100% (not less!) 

• Yellow = 99-60%

• Orange = 59-20%

• Red = 19-0%

I’ve also seen teams that are even more pragmatic about it and work with a thumbs-up and thumbs-down system. Personally, I think you miss out on the measuring factor that way but you can try it out if you like.

With the discussion of what has been achieved and what hasn’t been, it’s important to look further. Start asking yourself (as a team) what you want to move towards in the next quarter and what you want to pause/stop.

Doing The OKR Retrospective

Retrospectives help to better understand why, for example, a key result has or hasn’t been finished. It’s important to discuss what went well and what went wrong to ensure you don’t make the same mistakes again. Unfortunately, in my work as a Coach and consultant, I rarely see Leadership or Development teams retrospecting particularly on OKRs/the whole quarter. Spending two hours reviewing the previous three months and improving your process is always worth the investment.

When my teams and I retrospect we usually use one of the following three retrospective games:

• Start, stop, continue 

• Sad, mad, glad

• Went well, to improve, action items

As well as an external facilitator (someone who isn’t part of the team).

The internet is full of introductions and guides on how to do a retrospective. The reason why I’m a fan of these is that they’re easy to facilitate and produce good insights, outcomes, and action items/follow-ups.

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Quick OKR health check:

By now you should have an OKR draft which is already aligned with your key-stakeholders, for example, the Department/Leadership team. You should also know which OKRs you have and haven’t achieved. That means you’re ready to make a fresh start in the next quarter.

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#5 Reviewing & Presenting Your OKRs Globally

At the beginning of the new quarter’s first week, every team in the company should know what their priorities and next OKRs are. With that in mind, it’s important for the OKRs to be shared across the company. That means sharing the results of the previous quarter as well as the plan for the new quarter.

It’s important for the “OKR drivers” and teams to check to assess what’s changed around them one last time. Sometimes “last-minute changes” can occur on either a team or company level, which may impact your priorities.

There are different ways to collect and share OKRs for all company sizes. you can even find multiple tools and ways to share them and make them accessible. I was and am always a big fan of Google Slides and a “Master Sheet” that contains one or two slides from each team with the OKRs for the new quarter.

I’ve seen many companies do regular “All-Hands” meetings to share the company and Leadership OKRs. I like this a lot because it provides great transparency as well as a focus for the whole organization.

If you’d like to learn more on how other companies plan their OKRs this podcast episode might be a match! 🎙️

Some Final Notes and a Disclaimer

Not every company works in this setup. Some companies don’t define company OKRs and allow the teams to be fully autonomous when defining their direction based on the company vision. In others, it can be more complicated.

The order of events that I’ve proposed isn’t set in stone. You can change steps, remove them, or add additional ones.

The alignment part of the Market Leadership team, as explained above, only works for companies of a certain size. If the organization becomes too big, with too many Leadership roles, you should instead focus on high-level company OKRs as a Leadership team.

Last but not least: Don’t lose focus! 

If for example, an objective slips into the next quarter with the highest priority, it’s important to keep focusing on that. If it’s low priority, it’s important to stop working on it and move on to the most important objective. Sometimes, people can be tempted to start with the easiest OKR from the outset. I’ve learned the hard way that you always pay the price later. And it’ll be very expensive and stressful. 🙈

How do you plan your OKRs and what do you like most about the process? Let’s chat on Linkedin.