How To Run An OKR Workshop: A Practical Guide

OKRs (Objectives And Key Results) can be a powerful tool and goal system, but only if it’s introduced and used in the right way. Otherwise we end up with yet another process slapped on top of an already full calendar and roadmap. On of the most important artefacts in the OKR process and also on of the effective ways to get a team, business unit or leadership group aligned around outcomes and priorities is to run a dedicated OKR workshop.

The challenge? Most workshops fail, not because people don’t care or come with good intentions, but because preparation, facilitation or follow-up isn’t done well. In this guide, I’ll walk you through how to run an OKR workshop step by step – before, during and after – plus the skills and things you need to consider and watch out for as a facilitator, the common pitfalls to avoid and of course I will provide real examples for each.

1. Before The Workshop: Setting the Stage

A successful OKR workshpo doesn’t start when people walk into the room. It starts days and sometimes weeks before, with clear communication, context and preparation.

a) Strategic Context And Pre-Work

OKR workshop participants need to understand where the company is heading, what the current priorities are and ideally how their team fits into the bigger picture. Without this foundation, you can end up with objectives that sound nice in isolation but don’t move the needle strategically. A strong pre-workshop “package” usually includes the company vision, mission, strategy and/or top level OKRs. Bonus points if there is a short briefing on current challenges and opportunities relevant to the group participating.

Beyond context, you should prime participants with reflective questions. Ask them to consider: “Where do we want to be by the end of the quarter?” or “If we could achieve just one big thing, what would that be?”. This not only prepares the participants to be in the right mindset, but it ensures that everyone arrives ready to contribute in a meaningful way.

As an alternative, you can also have the group and their stakeholders already fill out a survey with what they think should be the focus and how they relate to the higher level priorities.

Note: maybe talk about deciding about top-down with bottom up feedback or bottom-up with top-down feedback. 

Good: Sharing the above mentioned materials with participants ideally 1 week before the workshop and/or start collecting input 1-2 weeks before the workshop.

Bad: Sending everyone a full day blocker that just says “OKR workshop, 9am – 5pm” with no other context. People will likely show up cold and unsure of what their contribution should be (if they show up and not challenge the invite).

b) Materials and Logistics

Logistics are often underestimated, but they play an important role in the effectiveness of the OKR workshop. The environment you create either encourages collaboration and focus or risks to derail it from the get go.

For in-person okr workshops, choosing a different or new meeting room can help with focus. In some cases (e.g. company okr workshop with leads or company execs) it might make sense to consider an offsite location can make a big difference by removing daily distractions and helping participants to focus.

For virtual sessions, preparing the “work area” in tools like Miro or Mural is essential for a successful and productive collaboration.

Equally important is the preparation of materials. Sharing an agenda at least a week before the session and providing OKR cheat sheets so everyone has a common understanding of what makes a good objective or key results are “table stakes” steps. Whether in-person or virtual, have the context, the team’s input and templates ready. Use sticky notes or digital equivalents for brainstorming and make sure the workshop follows the agreed upon agenda and a clear visual structure.

All of these small details add up to create the conditions for group focus and flow, rather than confusion and sometimes even frustration.

c) Participants

Who you invite and who you leave out can also influence the outcome of the workshop.

For company or leadership OKR workshops, ideally you would involve the leaders responsible with driving the OKRs that will be defined. However, the number of participants might get too high. In this case, it might make sense to be selective and try to keep the group under 10 participants so that deciding during the okr workshop doesn’t get bogged down.

For team-level workshops, it goes without saying that you should invite the people that are directly responsible for defining, driving and also working on achieving the OKRs + the team manager. If the team has a high dependency on another team or a particular stakeholder, it makes sense to invite a representative as well to avoid blind spots or defining goals that later need to be adjusted.

In general however, inviting too many people (e.g. an entire department for department level OKRs) ends up diluting focus and ownership and might lead to long discussions. Quality of participation matters more than quantity.
And remember that not participating does not mean input should not be collected or provided.

One detail that is often overlooked: if your team is new to OKRs, having an experienced facilitator or an OKR coach in the room can dramatically improve the outcome of the session. Their role is not to decide on the OKRs but to guide the process, provide feedback on weak OKRs and help the group stay on track.

 Good: For a leadership group, keep it to 8-10 people max but collect all relevant input to enable real discussion. For a team workshop, involve everyone plus manager and any relevant stakeholders the team has a dependency with.

Bad: A room of 25 people trying to wordsmith one objective. Over 90% chance of no decisions or quality OKRs defined.

d) Setting The Right Mindset

Even with the best preparation, materials and the right people in the room, an OKR workshop can still go astray if participants show up with the wrong mindset. OKRs are all about focusing on what truly matters and defining measureable outcomes that efortlessly show progress made. To get into the right mindset for defining such goals, sometimes a simple reminder of why they are all there, asking to disconnect from comms for the duration of the workshop or a short “what OKRs are/what OKRs are not” exercise are good steps to take. 

2. During The OKR Workshop: Facilitating The Process

Alright. We’ve prepped all needed materials. Context and pre-read was sent out. Input was collected. Everyone was invited. Room or virtual board is ready. Now for the main event.

The OKR workshop itself should have a predefined and somewhat clear flow. Think of it in stages: warm up, alignment and/or brainstorming, creating objectives, defining key results, and closing with next steps.

a) Warm-up, Agenda, Review

1. Set the space and try to build psychological safety. You can try and do this with a refresher on why they are all here or maybe a relevant icebreaker. Keyword here is relevant.
2. Share the agenda and expected outcomes
3. Review last quarter’s OKRs and lessons learned. It’s not always the case that the OKR review is in the same session as the one where you define the next OKRs. Also write down any action points or decisions that you take into the definition of the new OKRs.

Bad: Jumping straight into “let’s write some OKRs” without reviewing strategy, priorities or setting the scene.

b) Strategic Alignment

1. For leadership and exec groups: review the company strategy and resolve any questions or details that need to be clarified.
2. For teams: connect to department or company yearly strategy or company level OKRs, recheck priorities and ensure everyone is made aware of the bigger picture. Of course, answer any clarification questions.

Good: “Here’s our company strategy and yearly priorities. Which of these can our teams directly influence or help make progress on? Which of them are not relevant or not worth spending energy on during the next cycle?”

Bad: “Ok, so what should our objectives be for the next 3 months? Anyone have any ideas or shower thoughts?”

There is this joke I took with me from Romania, my home country:
A man is walking aimlessly through the desert.  After a while, there’s another person that comes up to the wandering man and asks “Where are you going?” to which the wanderer says “Not sure, really; mostly wandering…” to which the person who asked then says: “Ok, then let’s go this way because it will be faster”
The moral I take from this joke is relevant for the imporance of context when asking a team or group to define goals: If you are not sure where you are going, it really doesn’t matter what goal you will define. It will be just as good or bad.

So make sure that the group is aware of the strategic context, direction and priorities against which they need to define their goals.

c) Objective Definition

1. When I moderate, I usually ask the group to do some silent idea generation on their own before discussing them all in the group. This avoids loud voices dominating the conversation. It also avoids group think or everyone being biased to what was said first.
2. Group or cluster objective ideas into themes. Answer any clarifying questions if any objective statements are not clear.
3. Challenge objective clusters / themes to try and keep only the critical ones that the team has a realistic chance to achieve in the next cycle. Same principle goes for exec workshops, but the focus is on what the company can achieve. You can have the group vote, but I found it more useful to use radical elimination or “sudden death” tactics: “If you can only achieve one objective from here, which one would it be?” or “Will this really help us move the needle on the company priorities that we can influence?” or “If only this gets done this quarter, would it still matter and should we still keep it?” and other useful trigger questions that can help a team focus on what is important.
4. Work with the group to refine the clusters or themes that remain into the final objective statement. Make sure that you keep the team on track to define a good outcome statement objective without losing time on “wordsmithing”.

Good: the team ends up with a small number of high value and impact objectives that describe user or business outcomes.

Bad: the team doesn’t end up with final objective statements or they are all vague and not outcome based.

d) Key Result Definition

Defining strong Key Results is often the hardest part for a team or group. There are so many ways that key result definition can go wrong: listing tasks instead of measureable results and outcomes, cheat metrics or irrelevant key results, etc.

As a moderator and facilitator, this is where you’ll spend a good amount of time coaching, guiding and supporting the group to converge. Your aim is to support the team to find the right progress based measures for the objective that they are trying to achieve, guard rail and/or health metrics if they are needed, and of course these all have to be mostly or completely influenceable by the group or teams that will be working on them. And yes, 15 key results are way too many for an objective. Most times even 4-5 are too many.

Good: Ensure that the group defines the right progress based meaningful key results that also help them achieve the set objective. Stick with the team and don’t give way if the quality and relevance of the key results is not high enough.

Bad: Alright, we have KR sentences for each objective. Everyone good with what we have? Shall we call it a day?.

e) Commitment, Ownership, Drivers & Closing

Alright! you now have your OKRs for your group. But without clear ownership and commitment even the best OKRs risk falling into the “set and forget” box. Dedicate the final part of the session to assigning owners, drivers or both for the set OKRs.  What do I mean by these titles? Let me explain:
1. OKR Owner: since most OKRs should be a group effort and we are not talking about individual goals, ownership is generally assigned to the target team or unit that will mainly drive progress towards achieving it. So in this case, ownership is granted to a team or business unit. The chosen team is then accountable for achieving that OKR by end of the given cycle. 

2. OKR Driver: this is an individual role. The driver is tasked with ensuring transparency and clarity on OKR progress. The driver is the person that generally challenges the team when a key result is at risk or when there is not enough focus on achieving the OKR the team is accountable for. 

At this stage, it’s also useful to surface rissk and dependencies. If one objective or one key result relies heavilty on another team’s input or work, call it out explicitly and where needed, plan a follow-up alignment session. 

Finally, agree on how OKR related discussion will be integrated with normal way of working and how progress will be discussed and tracked – usually an OKR check-in every week or every two weeks works best. 

In some cases, OKRs are defined but without the actual values for KRs just yet (X or X% instead of actual values). This sometimes happens when teams need to go back to align on the values they can commit to. If this is the case, get a commitment from everyone by when should the final values be submitted – a few days up to a week is usually a good interval. 

Ending with clarity on ownership, rhythm and next steps ensures that OKRs “leave” the workshop as relevant, valuable artefacts for the team or group, rather than fading post-its on a wall or Miro board.  

Do you need help with your team’s or company’s onboarding to OKRs or Thinking In Outcomes?

Do you need an experienced OKR Coach and Facilitator that can help you get it right the first time around?

Just reach out and let’t have a call to discuss how I can help. You can also use the contact form at the bottom of this article

3. After The OKR Workshop: Embedding The Work

A good way to keep OKRs top of mind after the workshop and also ensure that we don’t fall into “set and forget” is to follow-up with workshop attendees afterwards.

a) Within 48 hours

The first 48 hours after an OKR workshop are key to keeping momentum. This is when energy is still fresh and participants are mentally connected to the discussions and what everone agreed to achieve. If too much time passes you risk losing all that momentum to other topics. As a facilitator or OKR coach, you should consolidate all outputs as soon as possible. Clean up the draft OKRs, resolve any inconsistencies or missing details and check one more time that the final set is concise, measureable and in alignment with the higher level strategy and priorities.

Key actions:

• Share the draft OKRs with participants
• Incorporate any new feedback and try to finalize the OKRs
• Document it all in an accessible space (Confluence, Notion, Dedicated OKR software)

b) In The Following Weeks

Follow-through and making OKRs a mental habit whenever people think about what to work on next is key to helping teams achieve the commited goals. The simple check-in every 1 or 2 weeks is an effective way to set the rhythm and keep objectives alive and top of mind and only need 15 minutes of everyone’s time. Feel free to also share with everyone check-in templates and align with them on the check-in flow and what everyone should share about their OKRs.

Teams also rarely operate in 100% isolation and OKRs sometimes do have dependencies: shared resources, cross-functional initiatives or sequencing of deliverables. Where needed, schedule short alignment sessions with the affected parties in order to reach a good resolution.

Key Actions:

• Run alignment sessions with other teams where needed
• Set up the regular OKR check-in meetings (every one or two weeks)
• Track OKRs visibly so they don’t get out of sight, out of mind.

Good: Following up immediately with workshop conclusions, next steps and remaining action points. Setting up all the ceremonies and ensuring drivers are on top of the commited OKRs.

Bad: OKRs are done. See you in 3 months…

4. Common Pitfalls In OKR Workshops

a) Poor Planning And Preparation

A poorly prepared workshop risks becoming a wasted one. You are responsible for ensuring an effective workshop to create important artefacts that not only will affect the participants but also the teams they work with and the company in general. So make sure that you have everything covered planing wise: what does the group need before the workshop, what should happen during, what I do after, how much time is really needed, are there any other risks and blockers for a successful session. Check everything and don’t leave anything to chance. 

b) Overloading With Too Many OKRs

If everything is important, then nothing is. Teams and even execs often try to cover everything, producing six, seven or even more objectives, each with five or more key results. The only result out of this? Diluted focus and inevitable disappointment and demotivation. Don’t shy away from ruthless prioritization and challenging the group. 1 key core objective with 2 key results might be exactly what the team needs to focus and storm through the most important outcome for the company. 

c) Forgetting Engagement & Follow-Through

One of the top pitfalls in terms of damage is treating or letting others treat the workshop as the end of the journey. Without check-ins, communication and ownership, OKRs are forgotten. A workshop without follow-through is like planting seeds but never watering them. 

5. Skills And Approach For The Facilitator

The person leading the workshop can make or break it. It’s important who gets chosen to moderate and facilitate and critical that the person selected is capable to dettach from the actual discussions and observe the group as a whole as they progress through the session. Here are some things to keep in mind skill-wise:

a) Facilitation Skills

A strong facilitator isn’t just keeping the time and taking notes. You’re guiding the flow, managing energy, parking topics that are not relevant and making sure that discussions don’t spiral out of control. Good facilitation means discussions stay on track, decisions are made and everyone can and does contribute. 

Good: “I hear two perspectives here. Let’s capture both and decide which aligns better with our strategy”

Bad: Dominating the discussion with their own OKR ideas. Taking sides or not challenging everyone equally due to their roles in the company. 

b) Coaching Mindset

The best facilitators are able to ask the right questions, at the right time, for the right purpose. These questions help the group look at things from a different perspective when needed. These questions help create breakthroughs and aha moments. And these questions always come from a place of genuine curiosity and not judgement.

c) OKR Knowledge And Previous Practice

You can’t facilitate the OKR workshop well without a solid grasp of what makes strong OKRs. Good facilitation not only corrects misconceptions but also educates to ensure that teams will define better OKRs on their own in future sessions. Experience and knowledge on using and working with OKRs also means the facilitator can help a team avoid OKR pitfalls. 

d) Able To Adapt To The Group

These workshops can sometimes get quite intense – clashing priorities, disagreements, scarce resources, conflicting personalities. A good facilitator is able to sense when the tension is rising, reframe conflicts constructively and create psychological safety so participants feel safe to speak up. Good facilitation actively builds a trusting atmosphere, encourages respectful debate and keeps the group focused ont he session agenda and goal. 

Final Thoughts On How To Run An OKR Workshop

Learning how to run an OKR workshop well is a skill worth developing, especially when your teams or company use OKRs as a goal system. These workshops usually end up impacting many more people and teams beyond the ones attending. So getting it right can create or preserve a lot of value.

Prepare thoroughly, facilitate with structure and empathy and then follow through so that OKRs go top of mind instead of set and forget.

And remember that if you need someone to help you onboard your teams and company in the right way to OKRs or train your internal OKR champions or coaches, you can always reach out to me or take on my OKR related training.

May you run a great OKR Workshop and remember to have a crazy day!