My One-on-Ones With Myself

Swapna Savant

Senior Director of Engineering at Headspace



When I was younger, my favorite inspirational quote was, “Aim for the Moon. Even if you miss, you will land among the stars”. Yet success is not about dreams but about plans, progression, and realization of worldly goals.

I started to take my career goals more seriously. I would align my goals with the organizational goals and make sure I stay on the right track. To do so, I came up with the concept I named a one-on-one with myself, a self-reflective activity accompanied by a detailed document that categorizes my goals and weights all my tasks against those goals. As a result, whatever I do is well-planned, ruthlessly prioritized, and aligned with my personal goals.

Actions taken

Planning my week

Everything begins with a solid plan. I start my week on Sunday by planning a week ahead. It happened almost accidentally the first time, but I realized that my week was more streamlined and efficient when scheduled on Sundays. On Sunday, I am more detached from the hectic pace of the working week and can more clearly reflect on my goals and priorities. Once my week is planned, I waste no time on things that are not slated for that week. Because my week is planned in advance, I know exactly what I should be doing on any given day.

I begin my day by staying offline. Earlier I was rushing to check my Slack and chat messages, but now I would merely glance over non-work-related emails on my phone and head for my running session. I am aware that I can get easily carried away, so I like to nip it in the bud. During my morning run, I have time to collect my thoughts and role play my whole day.

Whenever I plan my week, I set reasonable expectations -- things I have to do and things that I would be a rock star if I do. In the past, I was shooting for the Moon and would be easily disappointed after not attaining those goals. Therefore I prefer to set realistic expectations that I can attain; otherwise, I would get disappointed, which would reflect on my motivation and self-esteem. Realistic expectations, once accomplished, always inspire me to do something more. Also, I try to end my working week as early as possible and am lucky to have managers who were supportive of me being offline earlier on Friday for the sake of my well-being.

One-on-one meeting with myself

Once a month, I run a one-on-one meeting with myself. I am my own manager then and someone who decides on my career and reviews my career plans. To make the process easier, I created a document of the same title: “One-on-one with myself document.” The document consists of three main parts: personal goals, business goals, and where I see myself in five years.

Personal goals would be my top development goals, things I want to work on to be able to drive personal growth and development. For example, I want to work on my diminishing tendency. I am a natural protector who always tries to protect the team. However, I need to learn to lean back and have them grab their opportunities and find their way around. Also, one of my personal goals is to stay up to date with the latest technologies. Whatever comes up next, I want to know enough -- without getting into the weeds -- what it is about so that I can understand what my engineers are talking about. The same goes for learning how to communicate more effectively and package information for various audiences. For example, I am now communicating with execs about what my team is doing, and I need to articulate my message concisely. Furthermore, I have personal goals outside my job -- I write blog posts, I am part of Women Who Code and Plato, etc.


Business goals would be team- or organization-wide goals that I would like to align myself with. For example, I want to make sure that one of my teams delivers faster. My goal is to enable that by splitting a project and delivering it incrementally to customers. I also want to be more involved with data as data is becoming increasingly important for our organization. I was managing a data team, and now I work on the organizational data strategy. Another thing that I am tremendously interested in working on is product development and operational efficiency, particularly developing metrics that would track and showcase our growth. Though defining metrics is not within my team’s scope, I am enormously motivated to do things outside of that scope if I can make a significant impact.

The last section of the document is titled “How will my retirement look like?” This is my dedicated space for self-reflection and thoughts on my career progression.

I also write down all the tasks and place them in one of the columns. I have created three columns to help me determine who would benefit from completing this task -- my organization, team, or me personally. If it’s no on all accounts, I would either decline or delegate it. Every single thing that I do, I would put against my goals and see if and to what extent they contribute to those goals. If there is a task that I wouldn’t benefit from by completing it, but the organization would, I would delegate it to a person I think would grow the most by doing it.

Lessons learned

  • My self-reflection always starts with Why -- why my company vision is important to me and how what I do day-to-day is important to my personal growth. I need to know that I am growing in my current role to be able to stay motivated.
  • When I started to do my monthly checkups with myself, I was not thinking about the bigger picture and holistic approach to my career. I was focused on my team and what I could do for them. My monthly checkups helped me expand my horizon and look beyond my current role. When I realized that I wanted to transition to the next level, I started to eagerly learn about the role and responsibilities of a director. I would look at directors’ job descriptions and profiles, which helped me grasp things beyond my current perspective. For example, I was always taking for granted a slide on the development metrics shared in All-hands. I never questioned who and how they came up with those numbers. But now, when I want to become a director, I have to trickle that down and understand how directors are contributing to that slide.
  • As a woman, I was socialized that I shouldn’t openly say what I want. Moreover, I come from a culture that puts a lot of emphasis on modesty and sanctions ambition and an open talk about a career. I was taught to doubt myself, and it took me long to overcome that default behavior. I am proud of myself for being able to make that cultural leap and congratulate other people who did the same.
  • Someone is already living your future. I want to become a Director of Engineering; someone is already a Director of Engineering. To learn about my future, I would cold email other directors, initiate a conversation, wanting to learn how they got there. Then I would set my goals and priorities, researching various job profiles of directors from different companies and identifying specific things I should do to earn that promotion. Once I have listed those things in a spreadsheet, I should execute on them, proving my competencies. For example, directors manage managers. I currently manage two teams, but I am also mentoring one individual to become a manager. Of course, by helping them through mentoring, I am also helping myself ramp up my career.

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Swapna Savant

Senior Director of Engineering at Headspace

Leadership DevelopmentCommunicationOrganizational StrategyPerformance MetricsTechnical ExpertiseTechnical SkillsProgrammingSoftware DevelopmentCareer GrowthCareer Progression

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