Career Conversations

In a previous article, I wrote about the importance of managers needing to have frequent meetings with their direct reports aka one-on-ones. An equally important meeting managers need to have with their direct reports are career conversations. These meetings are an opportunity for a manager to help their direct reports reflect on their career and its trajectory; helping them define their career goals and identifying opportunities for them to achieve those goals.

“Each of us is responsible for our own career.”

It is not the responsibility of the manager to define their direct report’s career goals. Each of us is responsible for our own career. Rather it is the responsibility of the manager to be a coach and provide the necessary support.

I first started having career conversations with my direct reports when I was the Head of Research at Instagram. Rodrigo Schmidt and Peter Deng developed a framework for career conversations that was adopted by many managers at Instagram. I have since adapted the framework based on my experiences and feedback from my past direct reports. By outlining how we have approached career conversations, I hope you will learn some best practices that you can apply to your own career whether you are an individual contributor or manager.

Talking points for a career conversation

The career conversation is structured around 8 questions designed to help the recipient reflect on their career and its trajectory:

  1. What activities in your job have you enjoyed the most or found most interesting in the last 6 months?
  2. What activities in your job have you enjoyed the least or found least interesting in the last 6 months?
  3. Which projects are you most proud of in the last 6 months?
  4. Which projects are you least proud of in the last 6 months?
  5. What would you like to be doing in 1 year? (short-term career goals)
  6. What would you like to be doing in 5 years? (long-term career goals)
  7. What are you currently doing to achieve these career goals?
  8. How can I help?

These questions merely provide a framework for starting a career conversation. The career conversation should be tailored to the communication style that works best between a manager and their direct report.


Questions 1–4 allow the recipient to reflect on their day-to-day work. They are time bound to the last 6-months of work, so the answers to these questions are based on the direct report’s most recent experiences. I encouraged my direct reports to also list multiple projects thereby allowing us to identify themes.

An exercise an executive coach has given me to answer these questions is the love-it-loathe-it exercise. Take a piece of paper and fold it in half. At the top of one column write the header, ‘Love It’, and ‘Loathe It’ as the header of the other column. Throughout the day when you engage in an activity, reflect on whether you loved or loathed it, adding it to the appropriate column. When I have found this exercise difficult to do in real-time, I have used my calendar to do the exercise retrospectively.

Armed with this information, a manager can help identify opportunities that allow a direct report to do the work they find most rewarding. There will be times when they have to do work they loathe, but a manager can at least try to minimize this type of work.


Questions 5 and 6 are designed for a recipient to articulate where they would like to be in 1 or 5 years with regards to their career. A lot of people find it difficult to answer these questions — especially when envisioning their career further out. An exercise I have found useful is to first ask yourself if you would be happy doing exactly what you are doing in 1 or 5 years. If not, why? This will help identify areas you would like to be different and will be the basis for shaping your career goals.

A manager can use this information to understand a direct report’s desired career goals and motivations; and, identify opportunities to help them achieve those career goals.

It may be the case that some people have overreaching career goals. In this case, it is the job of the manager to understand the motivations for these career goals and help their direct report set more realistic targets that can be achieved. That said, there is nothing wrong with having stretch goals.


Questions 7 and 8 allow a manager and their direct report to formulate a plan to achieve their career goals. This plan should be scoped to action items that can be achieved in 6 months — it is unlikely they will fulfill all their career goals in this time, but they will move one step closer towards achieving them.

I have found there are three ways a manager can help their direct reports achieve their career goals:

  1. Shadowing
  2. Training
  3. Experience

Shadowing is an opportunity where someone can be a fly-on-the-wall observing situations they may not have got exposure to otherwise. Training can be a caught class where someone gains textbook knowledge. And experience can be gained by doing the job.

For example, I have had a number of direct reports who have moved from the individual contributor to management track. To help them achieve this career goal I have told them more about the day-to-day details of my role and identified opportunities for them to sit in on lead/manager meetings (i.e. shadowing); suggested classes that would equipment them with the appropriate knowledge (i.e. training); and, enabled them to mentor new-hires, manage interns and contractors (i.e. experience).

Scheduling your career conversation

I would schedule a 1-hour career conversation with each of my direct reports every 6 months after completing the self-assessment portion of the bi-annual performance review cycle. Performance reviews are a time to reflect on impact and areas of improvement. While not a performance review, a career conversation can build upon the thinking that goes into a performance review.

“It takes time to really articulate the answers to these questions.”

I shared the career conversation questions with my direct reports a week or two before we were scheduled to meet. It takes time to really articulate the answers to these questions. The day before the career conversation I asked them if they had the time to think through the questions. If not, we would reschedule the career conversation to make the most of our time together.

While having a career conversation is a good start it is only the beginning.

Unless we need to schedule more time, after the career conversation I ask my direct reports to reflect on the conversation and refine their 6-month goals and plan. Once these goals are finalized they are added to the top of our one-on-one document or group, so they are always top-of-mind. Once a month during a one-on-one we would review these 6-month goals and any associated action items to make sure we are making progress.

During the next career conversation, we evaluate the 6-month goals we previously set — were they achieved, do they need to be carried over or even redefined. This allows us to determine if they are making progress towards their career goals and pivot as necessary.

Career progression != management

Many people believe that in order for their career to progress they need to become a manager. This is not true.

Many companies have parallel career tracks for both individual contributors and managers. Look at the career expectations for each of these tracks to determine which of these paths is right for you. You can also read my Medium article, Should I become a manager?

Seek out a career mentor

While a manager can play an active role in helping achieve a direct report’s career goals, they are not the only person who can help. I have found it invaluable to seek out a career mentor. A career mentor is someone who you look up to, a leader in your discipline or the discipline you would like to transition to, and is perhaps in a position you would like to see yourself in 5 or 10 years. There is a huge opportunity to learn from their successes and failures, possibly accelerating your own career.

Start your career conversation today

A career is hard. It requires careful thought and time. Having a career conversation will make it a little easier.

If you have already had a career conversation in the last 6 months, take a moment to reflect if you are on track to achieving your goals. If you have not had a career conversation in the last 6 month, schedule your conversation today.

What has been your experience with career conversations? Please comment.

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Thanks to Rodrigo Schmidt and Peter Deng for helping me get started with career conversations; and Tomer Sharon for his feedback on this article.