14 Toughest Questions on OKRs answers by Ben Lamorte -Series 2

Welcome back to Series 2 of “14 Toughest Questions on OKRs” with Ben Lamorte, where we address the most pressing OKR challenges that organizations encounter. In this series, we explore common roadblocks, from building accountability to aligning cross-functional teams, all while ensuring effective implementation. Whether you’re facing issues with executive commitment, trying to establish OKRs as a cultural norm, or seeking better methods to evaluate OKR success Ben’s insights will offer you actionable solutions to drive real results.

1. How do you determine whether your 2024 OKRs were ambitious enough without being unrealistic?

When starting with OKRs, there’s often a tendency to either set goals that are too easy, achieving all of them, or too ambitious, achieving none. This is a common challenge. If you hit all your key results, it might signal that your goals are too easy, and it’s time to push for more challenging targets. On the flip side, you need to make your goals more realistic if you’re not hitting any of your key results.

Here’s a framework that works well: Commit, Target, and Stretch Goals. For each key result, you should define three levels of ambition:

• Stretch Target: This is the most ambitious goal, one that feels almost impossible but would be incredible if achieved. Don’t expect to hit this regularly, but it sets the bar high.
• Commit Target: This goal is more realistic to hit with about 90% confidence. This should be the goal you’re most likely to achieve.
• Target: This is the baseline the minimum you expect to achieve

Using this model, you should hit your commit target about 80% of the time, your stretch target around 10%, and your target about 50% of the time. This approach helps you
tune your OKRs. So, when writing OKRs, clearly label each level commit, stretch, and target so that everyone knows the context and can strive for meaningful outcomes rather than just ticking boxes.

2. If you are hired to facilitate a reflection and reset for a company that has just completed a pilot cycle, and you discover that there are too many OKRs and tasks masquerading as key results, how should you approach this situation?

When stepping into a new OKR cycle, especially after a pilot, it’s common to find an overload of OKRs and tasks that don’t truly reflect high-quality key results.

Here’s the approach I recommend:

1. If you’re facilitating a reflect and reset session at the end of the cycle, and there are too many OKRs to evaluate in one go, don’t panic. The first thing to do is narrow it down.
2. Ask each team to pick one or two key results for deep reflection preferably one that was achieved and one that wasn’t.
3. Since many organizations tend to overload their OKRs, focusing on quality over quantity is crucial. I’ve found that limiting the number of key results per session to around 5-10 per team is ideal. For each key result, dedicate around 10 minutes for discussion, and if it takes longer, consider scheduling follow-up meetings to dive deeper.
4. The focus should be on learning and applying insights for the next cycle, not perfection.

Reflect and reset sessions are about continuous improvement, so use the time to identify what worked, what didn’t, and how to tweak your approach moving forward.

3. If you’re facilitating a reflection and reset session for a team, should the key result champions attend the session, and how can you make the session more effective?

Absolutely! The key result champions must attend the reflect and reset session. These individuals are the spokespersons for their key results they have a deep understanding of the key result, its progress, and what needs to be adjusted. Without their presence, it would be difficult to make informed decisions or effectively discuss how to improve the key results for the next cycle.

As for making the session more effective, I highly recommend a peer review approach. One technique that has worked wonders is bringing two teams together for the session. Here’s how it works: One team presents their reflection and reset while the other observes. Afterward, the teams switch roles. This dynamic brings several benefits:

• Fresh perspectives: The observing team can offer insights or ask questions that the presenting team might not have considered.
• Increased professionalism: Presenting in front of another team adds a layer of accountability and encourages teams to be more structured and thoughtful in their presentations.
• Learning from others: Watching another team go through the reflect and reset process provides a learning opportunity, helping teams see how others are tackling challenges.

However, keep it small. Ideally, work with two teams at a time if you bring in more teams, the session can lose its focus and become unmanageable. By keeping it intimate and structured, you foster a more productive environment for learning and continuous improvement.

4. How do you ensure cross-functional alignment when implementing OKRs, especially when there are dependencies across departments?

Ensuring cross-functional alignment is one of the most common challenges when working with OKRs, and it’s crucial for driving impactful results.

So, how do we create this alignment? Let me share a simple yet powerful approach.

Start by involving everyone from the get-go. When drafting OKRs, make sure to identify dependencies between teams early. For example, if sales depend on marketing for lead generation or engineering relies on product resources, this should be clear. Don’t let these dependencies be an afterthought. I recommend co-champions for each key result one champion from the owning team and one from the dependent team. This ensures that both teams are on the same page and have shared ownership over the outcome.

Here’s a real-world example: I once worked with a client where the business and tech teams were on different floors of the building literally. This physical divide often led to misalignment in terms of priorities and deliverables. We changed that by making sure that every key result had a business champion and a tech champion, even if the result seemed primarily tech-related or business-related. These two champions had to sync up regularly to ensure they were aligned on their OKRs and dependencies. They had to update each other on progress and discuss what was working and what wasn’t. This process created honest cross-functional conversations, which helped maintain alignment and move the needle forward.

Over time, these two champion teams became a powerful method for ensuring cross-functional collaboration. It allowed for transparent communication and eliminated the silos between departments.

I also created a maturity model for cross-functional alignment, which has four levels:

• Level 0 (No Alignment): Teams work in silos with no visibility into dependencies until the end of the cycle. This often leads to unaddressed issues and missed targets.
• Level 1 (Identifying Dependencies): Teams identify their dependencies but fail to collaborate actively. This is a step in the right direction but doesn’t fully optimize alignment.
• Level 2 (Informal Collaboration): Teams begin drafting OKRs together, sharing their goals and aligning on actions. Still, it’s more of a collaborative effort rather than a structured partnership.
• Level 3 (Formal Co-Champions): Teams fully align by appointing co-champions from each department, regularly meeting to track progress and resolve conflicts. This is where real, high-level cross-functional alignment takes place.

So, how do you measure your alignment level? Start by asking:

• Are we working with our dependencies from the start?
• Are we treating these relationships as integral to success, rather than an afterthought?

If you’re not yet at Level 3, that’s okay use this as a benchmark to strive for. It’s all about fostering that collaboration from the beginning and ensuring the flow of communication between teams is constant and purposeful.

I challenge you to think about your current process and where you are on this alignment scale. The higher you go, the better your chances of achieving meaningful, aligned OKRs that drive business

5. What is a champion of accountability? Why is this now trending, and what was done before that neglected this practice?

In recent years, the idea of “champions” and “accountability” has gained momentum, especially in the context of OKRs. Previously, the responsibility for driving success was often limited to senior management, but now, organizations recognize the need for champions at all levels. OKR champions help develop a culture of accountability by ensuring all employees understand their role in achieving organizational goals. Without champions, teams may struggle with alignment and ownership. The trend toward champions reflects a shift toward empowerment and decentralized responsibility, creating a sense of shared ownership across the organization.

6. When setting commit, target, and stretch goals, how should you report your confidence during mid-cycle check-ins?

It’s important to report confidence at all levels of the goals commit, target, and stretch because each level provides valuable insights. Reporting confidence at all levels helps to identify potential gaps and enables teams to take proactive action. The target level gives a clear baseline, but understanding confidence across all levels commit, target, and stretch offers deeper visibility into the potential for success or necessary adjustments.

7. Who should run the check-ins? Who should hold teams accountable for executing tasks to move the needle on KRs?

Check-ins should ideally be run by the OKR champions or team leads. These individuals are responsible for tracking progress and ensuring that key results (KRs) are being achieved. Leaders are there to provide guidance and ensure that there’s no slippage. However, the accountability for executing tasks and moving the needle on KRs should be shared across the team. Everyone should understand their role in driving forward key results. Champions can help facilitate accountability by promoting regular updates and encouraging team ownership.

8. How do you “train” teams to write effective KRs? Outcome, not output?

The key to training teams to write effective Key Results (KRs) lies in focusing on outcomes rather than outputs. Teach teams to think about what impact they want to achieve rather than simply listing tasks. For example, instead of a KR like “Complete 100 customer calls,” a better KR would be “Increase customer satisfaction by 70% to 85% through customer engagement.” The idea is to measure the action’s effect, not just the action itself. Regular training sessions and feedback loops can help teams refine their KRs to ensure they’re impactful and outcome-oriented.

9. Do you advise linking committed OKRs to the performance of individuals?

Yes, linking committed OKRs to individual performance can help create a direct connection between personal contributions and organizational goals. It ensures that individuals understand how their work impacts broader company objectives and holds them accountable. However, it’s important that these links are clear and measurable, and that the focus remains on growth rather than simply hitting numbers. By doing so, teams stay aligned with business priorities, and individual performance is continuously evaluated in the context of the larger picture.

10. I understand OKRs are primarily Management Objectives and Key Results, which must be aligned with individual KRs and KPIs. That’s why it’s challenging to align with every department. Is this the correct interpretation?

Yes, that’s the correct interpretation. OKRs are often top-down at the management level and cascade down to individuals. Aligning them with KPIs at the department level can be challenging, as different departments may have different focus areas. However, aligning OKRs at the organizational level and ensuring vertical and horizontal alignment with individual and team KRs is critical. One way to achieve this is by mapping dependencies across departments and ensuring that each team understands how their OKRs contribute to the overall strategy. Collaboration and regular alignment sessions can ensure that all departments are on the same page.

11. What criteria should you use to evaluate whether an OKR was successful, even if the target wasn’t fully met?

When evaluating the success of an OKR, look beyond just whether the target was fully met.

Ask yourself:

• What progress was made?
• What was learned?
• How did the key results contribute to broader organizational goals?

Success should be measured by the impact made, not just the numerical target. Even if you didn’t hit the exact target, evaluate growth, insights, and how it advanced your strategic objectives. Continuous learning from partially met OKRs can provide critical insights that will drive future success.

12. How do you balance learning from past failures while fostering a culture of ambition for future OKRs?

Balancing failure and ambition requires fostering a culture where failure is seen as a learning opportunity, not a setback. Encourage teams to reflect on what went wrong, understand the root causes, and apply those lessons to future OKRs. At the same time, continue to set ambitious goals for the future. The idea is to build a growth mindset, where each failure becomes a stepping stone for future success. Celebrating progress, even if a target isn’t fully met, helps maintain motivation and ambition for the next cycle.

13. Can you align your OKR cycle to a planning cycle or keep them separate?

It’s often beneficial to align your OKR cycle with other planning cycles, like PI (Program Increment) planning. Aligning these cycles ensures that everyone is working toward the same objectives, streamlining the planning process. However, be mindful of the cadence. If your performance review cycle is quarterly, aligning OKRs with that cadence might make sense. In contrast, if your reviews are annual, you might consider a shorter OKR cycle to maintain agility and ensure regular course corrections. Ultimately, align your OKR cycle with your existing business rhythms to create consistency.

14. The problem occurs when management doesn’t support the results that don’t match the desired target. How do you communicate the value of such an approach?

Communicating the value of reflection and reset requires framing it as part of the learning journey, not a failure. Reflection provides valuable insights into what worked and what didn’t, and resetting is an opportunity to refine strategies for better results in the future. When communicating to management, focus on how the learning from missed targets contributes to the overall success and aligns with the company’s long-term vision. Share key wins, even if not all targets were met, and highlight the actionable insights from the process to show how continuous improvement is built into the OKR framework.

That’s a wrap on Series 2 of 1,4 Toughest Questions on OKRs Answered by Ben Lamorte! We’ve covered a lot resistance to OKRs, alignment challenges, check-in frequencies, leadership buy-in, and even how to apply OKRs across industries.