I was drawn to BetterWorks because it embodied a new framework for understanding how work gets done.

As a former consultant, I heard from executives, behind closed doors, at Global 1000 companies how their people were their most valuable asset, but they were having trouble with employee engagement. BetterWorks is a goal setting software platform built around how work is actually done in the workplace, and our team spends immense care and calories thinking about how to make work better.

As a company that drinks its own champagne, actually setting goals for ourselves is important to us; however, nobody tells you before you start that goal setting is a challenge. At BetterWorks everyone takes time to reflect on their goals at the end of the quarter. Reflection is important because: 1) helps us learn, 2) helps us write better goals, and 3) helps us communicate to the rest of the team how we did.

“We do not learn from experience … we learn from reflecting on experience.” – John Dewey

Here are a few lessons learned from setting four quarters worth of goals at BetterWorks.

My First Quarter: A Is Not OK

I first joined BetterWorks halfway through Q2 of 2014. I jumped straight in to working towards my goals. BetterWorks was a great way to show other people what I was working on. Showcasing my accomplishments felt so good that, frankly, I couldn’t help but crush it.

By our team quarterly review, I was “recognized” for my work. Blood drained from my face, the moment I heard my award. I received the award on the product team for 100% completion and for completing 10 of my 10 goals—a.k.a. The biggest sandbagger award. I had not stretched enough the first few months I was at BetterWorks.


Lesson Learned: You’re sandbagging your goals if it’s too easy for you to reach 100% by the end of the quarter.

My Second Quarter: Being Everything Is Being Nothing

Vowing not to repeat the bag of sand experience, I decided to stretch myself and rejiggered how I created goals. I crafted a series of objectives aimed at 4 pillars I thought needed work: improving efficiency and effectiveness of our product development, hitting product adoption targets, improving product quality, and instilling data driven decision. I had goals that touched project management, product management, quality, and data analytics. In trying to do a bit of everything, I wasn’t able to do anything well. John Doerr talks about one of the key benefits of the OKRs model: “focus on a set of priorities.” My answer to developing focus was to focus on everything. Wrong answer.

Lesson Learned: You should focus your goals. Goals should represent what you deem as most important, not everything you do. Goals are a way for you to say no.

My Third Quarter: Stretch the Goal Muscle

I was in the throes of the quarter and didn’t spend a lot of time thinking through my goals. Consequently, nearly all of the goals didn’t connect with any objective. My goals this quarter were a collection of things cascaded down from people in the organization. I had a cluster of goals around delivering predefined features, goals around partnerships and integrations, assisting customer success. In short, my goals were a series of deliverables. Because they were items that needed to be done, my goals quickly devolved into a list of tasks. It became a rote check-the-box exercise; get through as my items as fast as possible.

Lesson Learned: Goals need to be both top-down and bottom-up. Goal setting should be a conversation with multiple stakeholders within the org.

My Fourth Quarter: Communicating Progress

Before the new quarter rolled around, I sat down to define the goals I thought were important (Which I’ll cover in a future post). Over the holiday break, I took an hour out of my day to think about where our company needed to be by the end of 2015. After picking up some goals that aligned with our top company goals, we used both lists to form my goals. I ended up with some big, audacious goals. As we neared the end of the quarter, I started to review and reassess my goals and came to the realization that while my goals had a lot of protein and weight, they weren’t chunked out into smaller pieces. Chunking wasn’t about breaking things into small tasks—every Monday I set a weekly goal for myself based on my quarterly goals; it’s about communicating and updating my progress to the rest of the team. Often goals are owned by an individual, but work is done by teams. Successfully completing a goal isn’t only about completing the goal, but enabling those who need to be consulted and informed of your progress.

Lesson Learned: Break down your goals so you can be more agile. Frequently communicate any progress of your goals to your stakeholders


Goal setting isn’t intuitive. It’s easier for us to think about what to do today as opposed to what’s the most important thing that needs to be done. Just as important as setting good goals, is reflecting on how you can improve and make it 1% better next time.

Lessons learned:

  1. You’re sandbagging your goals if you can easily reach 100% by the end of the quarter.
  2. You should focus your goals. Your goals shouldn’t represent everything that you do; they should be what you deem as most important.
  3. Goals need to be both top-down and bottoms-up.
  4. Goal setting should be a conversation with multiple stakeholders within the org.
  5. Break down your goals so you can be more agile.
  6. Frequently communicate progress of your goals to your stakeholders.