From outputs to outcomes — changing the approach to OKR

About OS33

Few industries are like financial services when it comes to strict regulatory oversight and security needs. OS33 created Workplace, a SaaS platform for compliance and productivity enablement for the wealth management industry. The company focuses on servicing enterprise-scale Broker-Dealers, insurance companies and other financial institutions who leverage independent reps/ advisors, as well as RIAs affiliated with the nation’s top custodians.

Jason Arrigo is the Director of Education at OS33 and is responsible for training customers on their platform. Jason also leads OS33’s OKR program.

Challenge

Take the OKR program to the next level

Upon joining OS33, Jason bought with him considerable experience working with OKR from a previous position. OS33 already had an OKR program but didn’t have anyone dedicated to managing it internally. Drawing on his experience designing and implementing OKR in a previous role, Jason began working with the team at OS33 to take their OKR program to the next level. “I’d used Perdoo in a previous role so it made it much easier to choose OKR software to help OS33 when I joined”, said Jason. “One of the big challenges I had, when I started, was making changes to the approach the team had to OKR”, he added.

With OS33’s existing setup OKRs stored in Microsoft Excel and Confluence the focus was mainly on Group OKRs, with less clarity on Company OKRs. The setup was also based on the theory of cascading, where a Company Key Result becomes an Objective at the Group level, an approach that Perdoo doesn’t recommend. “We used to have these big executive meetings”, explained Jason. “The first time we worked on OKR I was asked to prep everyone and get new OKRs created in one day. The goal was to work out Company level, Department level and Team level OKRs all in one go.”

Although Jason knew from previous experience that creating OKRs often takes longer than at first thought, he decided the best way for the team to learn this was through experience. Following the 3-hour management session, it took another 3 weeks to get all their OKRs finalized before they started their first quarter using Perdoo.

With their second quarter fast approaching, the executive team approached Jason and suggested they meet a few weeks earlier, starting with the executive level OKRs first before rolling it down to teams.

“After the first quarter, the team realized that we needed to simplify”. Explained Jason. “I saw our Engineering team had 8 Objectives. I told them they should keep it between 3 to 5 because any more and they wouldn’t be able to focus.” he added. “Guess how many of the 8 Objectives they were able to achieve at the end of the quarter? 3 to 5.”

The goal of restructuring OKR became clear to Jason; to help OS33 achieve better prioritization and focus using OKR as the tool to achieve that.

We really worked on understanding and clarifying what was important. It helped us re-examine priorities and our abilities to achieve them.

Jason Arrigo, Director of Education at OS33

Solution

Software & Coaching

Working with Perdoo, Jason helped OS33 gradually change their approach focusing on measuring outputs as indicators of success, to using OKR to achieve measurable outcomes.

We worked with Jason to unpack the existing structure of Company OKRs and noticed an area where they could improve. While company OKRs represented outcomes, sub-Objectives aligned to them represented projects, Initiatives, and jobs to-be-done.

Focus on outcomes

“A major part of how Perdoo helped shift thinking is, depending on the type of leaders you’re working with, they have these strategic goals in mind, like “successfully acquire this new company” and then they make sub-objectives which represent the things they want their teams to do”, Jason explained. “So one of the things we worked on was shifting Company Objectives to the strategic level and thinking: ‘How do I grow my company to be able to serve larger customers, and how will I know if I’ve achieved that?’ ” he added.

Rather than creating cascading sub Objectives to show what teams needed to do, OS33 gave their teams greater freedom to decide their own approach to moving Company Objectives forwards. With clear, measurable Company OKRs that reflected strategic priorities, team’s created their own OKRs and focus increased.

Clear priorities

“When we laid out our annual Objectives in Perdoo, we really saw the outcomes the company wanted to achieve line up with our team’s priorities. We could also say that it’s ok if our teams are not focusing on a particular Company Objective this quarter, we can focus on it next quarter instead”.

By working quarter to quarter and getting a feel for OKR, OS33 started to see their teams drive progress towards company Objectives.

Result

Focus on the work that has the biggest impact

Since re-organizing their OKR program, Jason reported that the teams take OKR much more seriously. This is thanks to the way the closing process forces the organization to look objectively at the outcomes they’ve achieved.

“The outcome of OKRs, whether it’s win, lose or draw, is something you can really learn from,” said Jason. “In the past, it was “how would you rate this Objective”? And the answer would be, like a subjective, “oh a 2”. Now the conversation has shifted to “we accomplished 75% of this Key Result, 25% on this one, and 50% on the other one” and we can see exactly what was done toward that Objective”. He added. “Now it makes it much easier to see, oh that Key Result really moved and this one didn’t, and we can ask the question “why”?”

Before enlisting Perdoo’s support at training OS33 in the OKR methodology, Jason felt that many important decisions were subjective.

“Now that we’re following the Perdoo methodology, we can successfully look back on a Key Result and say, ‘if that was a measure of success and we didn’t achieve it, what did we learn? This leads us to uncover things like ‘well, we tried this and it didn’t work’ or ‘there was a problem that impacted our delivery to customers’, to which you can now say, ‘well now we know that Objective was roadblocked because of these problems, how do we create a new OKR to fix them?’ ”

Learnings are just as important to OS33 as working towards their OKRs because they help the team make better decisions in the future. The outcome of their improved OKR program is that OS33 can shorten the timescale for making better strategic decisions by learning from the outcomes of their OKRs each quarter. This is a big change from how they were previously using OKR.

“My advice to someone who’s bringing OKR to a new company is to really focus on training the executive team by explaining the benefits and value of OKR to them”, said Jason. “I really tried to distill it to bullet points and focus on definitions like ‘what is an Objective’, ‘what is a Key Result’. That really helped people understand it. When executives buy in and really understand the benefits, it makes the whole roll-out process much smoother,” he added.

The future is bright for OS33 and their OKR program. “When I’m putting my OKRs in Perdoo, I can really see how they’re contributing to this explosive growth we’re experiencing, and when I look back I can see exactly how what I’ve done has contributed,” said Jason. “That, to me, is really satisfying”.

The outcome of OKRs, whether it’s win, lose or draw, is something you can really learn from.

Jason Arrigo, Director of Education at OS33