How to Grow a Planning Mindset

Chitrak Ojha

Director of Engineering at Twilio



Planning is often only discussed towards the end of a planning cycle -- usually a quarter -- when most of the people responsible for the execution will be excluded from the planning. Even when there is an effort to make the process more participatory, people are brought in when key decisions are already made and when they can’t significantly influence the process.

Instead of including some people at some time, the planning should become a centerpiece activity that would require people to make an intentional effort to plan throughout a planning cycle.

Actions taken

As a manager, my first goal was to get teams into a habit of planning consistently. To do so, I had to create an environment where rather than intensifying the planning towards the end of a quarterly cycle I could encourage them to develop and nurture the habit of consistently looking ahead and not only being focused on what is going on at the moment.

That required a significant mindset change since teams would typically spend more time planning toward the end of a quarter, squeezing in all the planning activities in the last two weeks of the quarter.

The most important thing I had to do was to include the whole team and promote the planning mindset among all team members. People on the business or product size of things are more inclined to look ahead, but I wanted to include people on the team who would execute on things. Moreover, involving them earlier in the process could result in feedback beneficial to the planning itself.

I introduced weekly planning sessions lasting from 30 minutes to an hour and the focus of these sessions was on the next cycle. As soon as a quarter would begin, we would start having discussions about the next quarter. We would start discussing a set of items and their validity and as time would pass, the discussions between Engineering and Product would become more concrete and centered around prioritizing the next forward-looking items. After the first half of a quarter, we would be able to prioritize much better and remove the overwhelm that would happen when planning is all stuck in the last two weeks of the quarter.

Also, spreading the planning throughout a quarter helped us better prepare. For example, during the first month of a quarter, we would be discussing a project that would require a lot of discovery and we had to re-align ourselves to include the discovery in our regular activities. In addition, consistent planning could empower the team to create its own team processes that would improve their overall performance.

Lessons learned

  • The consistent planning allowed the team to step back and look at the broader picture that spread beyond the most immediate focus on the current items they are working on. It also allowed them to alleviate the overwhelm of the hectic planning happening at the end of a quarter.
  • Planning improves the alignment between long-term business objectives and priorities that are communicated to Product and Engineering and that are translated into concrete engineering projects.
  • Consistent prioritization also helps with focus. We are constantly prioritizing and are able to differentiate things that should be top priorities and deserve our undivided focus. Therefore, planning is also a path to continual improvement.

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Chitrak Ojha

Director of Engineering at Twilio


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