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March 04, 2022 by Molly Weybright

OKR Planning: 12 Tips for Small Businesses

As a growing small business here at Service Direct, we spent many years trying to figure out what goal planning strategy worked best for us. At times it felt like we were trying to force a square peg into ab round hole; other times it felt like we were almost there but something was just slightly off. That trial and error is something most small businesses are familiar with, and something that we have had plenty of experience with ourselves.

We are here to talk about the goal-setting methodology of Objectives and Key Results (OKRs) and how it has helped us continue to grow as a company. We began using OKRs for goal planning in 2017 and haven’t looked back since. But it hasn’t been all smooth sailing from the outset of our OKR journey—initially, we made more mistakes than not. Now, however, we use this methodology daily to boost individual productivity, team collaboration, and company growth.

THE OKR methodology

The OKR methodology was originally developed by Andy Grove at Intel, who then taught the concept to John Doerr, an early Google investor. The rest, as they say, is history. The general idea of OKRs is to create a flexible template for goal setting that could be molded to fit any company’s needs while still providing an effective framework to get those goals completed. 

OKR Framework Diagram (1)

The OKR goal-setting framework pairs the objectives you want to achieve with the key results you’ll use to measure progress. This ensures your goals are tied to your team’s day-to-day work. OKRs focus on results rather than processes, which allows creative thinking and flexibility on the best ways to achieve objectives. With an understanding of company-wide objectives, and with specific results in mind, teams are able to collectively shape their day-to-day work for the upcoming quarter. Because of that, OKRs should be set while thinking of the overall quarterly and yearly goals for your company while also connecting them to day-to-day work. 

In order to best connect your big-picture OKRs with the day-to-day work, you will want to conceptualize your OKRs as cascading. That means working down from the company goal to build out smaller OKRs for teams in order to ensure every employee has work to do that contributes and directly relates to the company-wide goal. When employees are able to connect their daily work to the big picture goals of the company, their motivation doubles, which leads to an increase in productivity. 

The Difference Between OKRs and KPIs

People often get Objective-Setting confused with Key Performance Indicators (KPIs). Initially, we set our OKRs with a KPI-based mentality, meaning we would set an objective like "we want to see X results in a given quarter." Then, despite doing a solid job executing on a project throughout the quarter, if we didn’t reach that specific number we weren’t sure whether to mark the project complete. This is not an effective way to think about  OKRs.

What We Learned. OKRs should focus on the projects and initiatives that the team has agreed are most important rather than focusing on a single specific number or result. By taking the pass or fail aspect out of the goal-setting process with regard to hitting a specific result, the team is able to focus on the bigger picture. We aren’t saying don’t think about KPIs, but we recommend tracking them separately from OKRs.

OKRs vs KPIs Comparison Graphic

OKR PLanning: Secrets To Success

We wanted to write down the lessons we’ve learned from years of quarterly OKR planning so that other small businesses can avoid making the mistakes we’ve made. From leadership buy-in to goal visibility and project breakdown, these are the top things we think you should know about OKR management. 

#1 - Make it Visual

Originally, we tracked OKRs in documents or established them verbally. This made it very difficult to visualize what exactly we as a company are working toward, especially for the team members that may not have been a part of the planning process from beginning to end. 

What We Learned.  It’s important for individuals to understand how their work is feeding directly into our collective, shared company Objectives. To do that, we have an OKR bubble chart that very clearly helps teams see the big-picture view of how each KR feeds into an O. 

Example OKR Bubble Chart Diagram#2 - Get Buy-In From All Teams

When we first began using OKRs our company was still very small and very busy. This meant that some people were updating OKRs regularly while others were only updating them at the end of each quarter. This meant that it was very difficult for leadership to see the overall picture of how things were progressing, which prevented people from stepping in to help and made it difficult to plan. 

What We Learned. Over the years we have found that all of the teams need to commit to the OKR process, and the best way to ensure this is to have full leadership buy-in. That means everyone is held accountable for updating the OKRs regularly. This is also important because we have many teams with overlapping quarterly goals that need to be able to monitor progress as the quarter unfolds. 

#3 - Give Yourself Enough Time

As a small business, you’re busy, there’s no getting around that. It can be tempting to brainstorm, write up, and solidify OKRs as quickly as possible. When we first started we would try to do all of that in 1 meeting at the start of the quarter. We quickly realized that hastily creating OKRs often results in changing the strategy mid-quarter or missing the mark entirely, which can lead to teams resenting the goal tracking process as a whole.

What We Learned. We have found the sweet spot for OKR planning to be about 4 weeks. Over those 4 weeks, we hold managers’ meetings, cross-team meetings, individual team meetings, and an all-hands quarterly meeting. Although this process may seem highly time-consuming, it ensures that OKRs are ultimately not a waste of time, that OKRs are actually finalized before the start of the quarter, and that they produce the results that keep the company growing and moving forward.

OKR Planning Timeline Graphic

#4 - Keep OKRs Specific and Time-Bounded

There is a natural inclination to lean toward more open-ended OKRs because it seems less daunting and afford a level of flexibility that many people prefer. In the past, we would make OKRs that were broad, such as “complete Project X,” which is both fairly general and not time-specific. With goals like that, we found that there wasn't enough direction and thus less guidance to complete them.

What We Learned. Establishing both specific timelines and clear wording for what each OKR is set to accomplish helps the team complete them on time and well. We have found that setting goals like “launch bite-sized piece Y by March 1” was able to provide the direction to keep the team motivated. Plus, we all benefit from seeing progress little by little and this version of crossing items off a to-do list accomplishes that by representing clear, forward progress. 

#5 - OKRs Are For Everyone

With traditional goal-setting techniques, team leaders and managers tend to take most of the control of the goals and progress. When we first started using OKRs we naturally tended toward that traditional approach, but quickly found it did not work. That was because in order for OKRs to be effective, every person—not just the company executives—needs to be invested in the achievement of KRs. 

What We Learned. Not only did we learn that every individual is necessary for successful OKR planning and completion, but we also learned that some people might be more hesitant to voice concerns or thoughts in group settings. Leadership should get regular OKR progress updates from the individuals they supervise and managers should continually discuss OKR progress with individual contributors. It’s crucial to keep the conversation going. 

#6 - Plan Across Teams

In the past, when it came to OKR planning and development, each team would create their quarterly goals in a vacuum. They would plan their quarter based on what they felt was most important. While there isn’t inherently anything wrong with that thought process, it ended up hindering the company as a whole as teams tackled different issues rather than focusing on overlapping goals for the company. 

What We Learned. Collaboration is extremely important when it comes to creating quarterly goals that connect with one another and ultimately work toward solving a company-wide issue or the improvement of the company as a whole. It’s important to have cross-team involvement so that the key results are working toward common objectives. Additionally, Objectives are often dependent on multiple teams, so in order to ensure OKRs are effectively planned and achieved, cross-team planning is essential.


#7 - Make Sure Everyone Is Using The Same OKR Tracker 

Company-Wide OKR Master Tracker

Initially, we had teams working across many different platforms—some in Asana, some in a spreadsheet, some in a document, etc. This resulted in teams focusing solely on their OKRs rather than the company-wide goals. Additionally, this also required teams to set up extra meetings and communication channels if they needed updates from one another.

What We Learned. The benefits of a single source of truth and information when it comes to company OKRs are seemingly endless. Not only can anyone check out the progress of any team’s goals, but people can also figure out who to contact with questions regarding objectives or key results. Whether you are using an OKR tracking platform or decide to build your own tracker, it's important that you maintain one 'source of truth' for OKRs that anyone can reference at any point to see how well their team and others are working towards shared objectives.

#8 - Meet Regularly and Often (We Suggest Weekly)

We have previously tried biweekly or monthly meetings and found that they were not enough to keep up with our objectives. Those meetings often ran long and we found that some tasks had been blocked by a lack of frequent meetings. Plus, it can be hard to break out of the day-to-day work and look at the bigger picture. 

OKR Reflection Zoom

What We Learned. With some trial and error, we have found that weekly 30 to 45-minute meetings help the team look up from the daily grind and see the progress or holdups on our high-level objectives. These meetings also serve to connect across teams and reinforce the collaboration element of OKR planning. Additionally, with OKR goal-planning it is important to both celebrate wins and see where we are falling short. This allows us to understand what we are doing right and what we need to do in the future to work toward achieving those Objectives. 

#9 - Singular Ownership of KRs is Key

As previously mentioned, OKRs are the most successful when they are team-oriented. However, when we initially started with team-centric KRs, we found that having a project with multiple owners is just as unproductive as having no owners.

What We Learned. While the entire team and company will need to be involved and invested in the OKRs as a whole, it’s important to have one single person with stated ownership over each KR. Having a singular owner responsible for reporting on the KR empowers that person to do what it takes to achieve the goal and encourages others to do the same.

#10 - Break Down Large Projects

In the past, we have mistakenly tried to tackle large projects in a single quarter, which in theory is great, but in practice can’t be done. When we get excited and don’t think critically about how much time a large project will take, the team can start to feel frustrated or overwhelmed if that project is still on our OKRs multiple quarters down the road.

What We Learned. It’s important to walk the line between realistically pushing the team toward a goal and unrealistically trying to achieve results that need multiple quarters. By breaking up large projects into smaller, more achievable OKRs, we can keep the momentum going on those large, important goals while ensuring that our team doesn’t feel discouraged. 

#11 - Less is More

It can be tempting to throw as many KRs as possible at the board and see what sticks when it comes to building out quarterly OKRs. This quickly leads to overwhelmed teams and a large number of partially completed projects rather than a smaller number of KRs that have been reached. 

What We Learned. We have slowly become better at narrowing down our ideas to 2-3 of the most impactful things a team can work on over the course of the quarter. This way, the whole team can be pushing for the same major goal and there is a much larger likelihood that the goal will be achieved. It’s still difficult for us at times to pinpoint which KRs belong in that upper echelon of goals but with time they have become easier for us to identify.

#12 - Add A Curveballs Section

It is inevitable that unplanned things will come up through the quarter, or maybe priorities will shift based on other things. This will always happen. This also quickly leads to adjusting your OKRs to match your current priorities, or by just adding another line item to the list.

What We Learned. Plan for unplanned work. We do this by adding a curveballs section at the bottom of our OKR Tracking Sheet to make any added or unplanned work more visible and to better understand why we didn't plan for it. Anything in curveballs should be critically assessed for level of importance and effort relative to existing OKRs.

After over 5 years of goal planning with OKRs, we can comfortably say that the OKR method is one of the most effective ways to keep moving forward as a company. It has been a learning process that has been extremely rewarding in both the short and long term. Every quarter we move closer to our company-wide goals thanks to the OKRs we have set and will continue to establish. If you want to use OKRs to keep your company-wide progress strong and steady, the tips we have listed will help propel you toward the completion of your goals and a higher level of productivity. 

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