Conversations at Obvious – Part 1: Career Conversations

  • Monica Pillai
5 minute read
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Achieving professional dreams, large and small, through clarity and mindful planning.

Career conversations help individuals gain clarity about their professional lives as well as how that plays into their personal goals. At Obvious, these conversations occur every 6 months, starting 6 months after employment. Each conversation takes about 2 hours and focuses on the person’s growth trajectory by developing a custom-tailored growth plan based on their medium and long-term aspirations.

The Why

People choose different career paths and have varying professional goals. While some people seek constant growth and more responsibility, others want stability and time to master some skills. An overarching career framework helps, but we believe it isn't enough to ensure everyone’s success. While it's definitely a good first step for getting the lay of the land, it works even better when it's supplemented — by helping each individual with clarity on how to achieve their specific goals by developing a personalised growth plan.

Career conversations help managers understand the values, dreams and professional aspirations of their direct reports. Naturally, this turns into a great chance to create the right opportunities for the right people!

Here's how we conduct career conversations at Obvious:

Step 1: Value System

Recommended time: 30 – 45 minutes

To offer an individual enjoyment and satisfaction at work, we think it's imperative that the organisation supports the person’s value system. Values are different than goals. In fact, values are what remain intact when goals change. They are what we practice daily without expecting short-term results. For instance, honesty, safety, and teamwork are examples of personal values.

To understand a person’s value system, we think it's a must to first understand the individual. One-on-one conversations offer a solid opportunity to know our direct report’s personal life story, slowly building a rapport over time. Depending on how well we know the direct report, we may only spend a few minutes recapping our understanding and offering them a chance to tell us more. Or, we might concentrate on learning more about them, especially if they are new.

Once we break ground in knowing our direct report better, we use that information to build their value system into their personalised growth plan. For example, a person who enjoys playing team sports might have effective teamwork as a core value. So, part of their growth plan should ideally ensure that they work on projects with collaborative teamwork instead of projects that rely heavily on deep individual contribution.

Step 2: Aspirations

Recommended time: 30 – 45 minutes

The only way to ensure that everyone bring 100% of themselves to work is by making sure that they find their work interesting. A conversation about aspirations can help make this happen. This conversation can be broken down into 3 steps:

Dreams: A good way to start the conversation on aspirations is to ask people to imagine what the pinnacle of their career looks like. We like to ask them to articulate the most important things they want to achieve when they're at the top of their game. This question can elicit interesting responses, such as “I want to deliver a TED talk”, “I want to be a community leader for women in tech” or “I want to create a series of typefaces that will last for decades”. Together, consider creating a list of 3 to 5 such dreams with the individual.

Skills: Achieving dreams often requires us to gain new skills or improve existing ones. To see what those are, this excerside will help: for each dream, write down a few necessary skills. For example, to become a community leader for women in tech, one might need deep technical skills, public speaking skills and people management skills. These are the competencies that will help the individual make their dreams a reality.

Values Check: Sometimes, people’s dreams do not align with their skills and values. For example, a person might want to be an entrepreneur (dream) managing a large team working on complex problems (value), but at the same time she might want to contribute really high-quality code (skill) herself. It can be quite difficult to contribute deep technical work while fulfilling the entrepreneurial responsibilities of running a company with a large team. A manager's job here is to work with the direct report to help them find their area of focus and be successful by aligning their values, dreams and skills.

Step 3: Growth Plan

Recommended time: 45 – 60 minutes

Now that there is a ready list of skills that the individual might need to achieve their dreams, it's time to hone them through a personalised growth plan that creates the right opportunities. For instance, if the direct report needs to enhance leadership and product direction skills, we create a growth plan that allows that individual to work on a project where little or no product direction has been set. We consider providing an opportunity to lead a small team. If the direct report needs to develop a deep technical skill, we could offer an opportunity to work on a project filled with challenging technical problems.

A personalised growth plan helps everyone choose their own career trajectory at a pace they are comfortable with. Alongside helping everyone at the workplace feel like they are moving towards achieving their dreams every single day, we believe this exercise helps the organisation align business priorities and expectations across the board.

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At the next meeting in 6 months, we go through each step again but with a mindset to adjust and course-correct. Shifts in values and aspirations occur constantly, so we'd recommend checking in to see what changes have occurred. Then, update the growth plan to account for these new expectations.

Healthy businesses are a function of happy individuals who bring 100% of themselves to work every single day. That only happens when individuals see a path to their ultimate success at their organisation!

If you’re looking to work in a company that invests in you, here's our hiring page — come see if you find something interesting!