Career Development Planning Questions

Part of the role of an Engineering Manager is to help others to achieve their career aspirations. However, it’s not always easy for people to articulate the direction they hope their career will take them. For some, it can be difficult to describe their ideal future role, or to answer that “where will you be in 5 years time?” question.

I have struggled with this question too. I wanted to share a technique one of my previous managers used with me to uncover my aspirations. During the session, he asked a number of questions about my current role and then asked me to transport myself to a point in time in the future. Once there, we discussed what my day-to-day work looked like, and uncovered some of the aspects I considered important for any future role.

We then spoke about the distance between my current day-job and the role I described as part of my future self, and built a plan to address the differences.

The technique is very similar to the futurespective retrospective activity that many agile teams use to uncover problems with the way they work.

I’ve used this technique with others in my team to build their own career plans. In doing so, it’s helped me to understand some deep-seated desires within people I work with, and given me a better understanding of the things I need to do to help them reach their goals.

If you want to run a similar session, I’ve included the questions I ask below. I usually conduct these sessions in front of the whiteboard, asking the questions, and writing or drawing the answers on the board. This allows the person whom you’re conducting the session for to really concentrate on visualising the future, rather than having to take notes.

First, let’s talk about your current role

  • How do you describe you current role?
  • What does a typical day or week look like for you?
  • Who are your key stakeholders?
  • What makes you happy?
  • What was the best thing you worked on?
  • What irritates you?
  • What was the worst thing you worked on?
  • Thinking of a typical week, how would you plot your time on a pie-chart?
  • Are you more of a specialist or generalist?
  • Are you more strategic or operational?
  • Are you reactive or proactive?

Now let’s look forward. Imagine we meet in 5 years time…

  • Where are we meeting? What are we doing?
  • Where do you live? Have you moved?
  • What are you doing wth your free time?
  • Are you working? Is it full-time or part-time?
  • Which country are you working in? Which City?
  • Are you working from an office or somewhere else?
  • Do you travel with work? How many times a quarter?
  • What industry do you work in?
  • Tell me about your work. Do you work for a company? Or yourself?
  • Are you a developer? What are you building?
  • What is the culture of your workplace?
  • What projects are you working on? Tell me about them.
  • Tell me about the company you work for.
  • How big is the company? Where are they based?
  • What is your role? Who are your stakeholders?
  • Are you managing people? How about mentoring people?
  • What do others say about you?
  • How do you learn new things?
  • How do you stay current?
  • Thinking of a typical week, how would you plot your time on a pie-chart?
  • Are you more of specialist or generalist?
  • Are you more strategic or operational?
  • Are your reactive or proactive?

Looking at you future self…

  • Is there anything else that will help me understand your future role?
  • What aspects are non-negotiable?
  • What answers are you certain of? Which are more difficult to answer?

Comparing you and your future self…

  • What are the main differences?
  • How did you move between specialist and generalist?
  • And how did you move between strategic and operational?
  • And between reactive and proactive?
  • What skills are you missing?
  • What do you need to improve?
  • What new experiences do you need?
  • What’s going to stop you from achieving your aspirations?
  • Who’s going to stop you from achieving your aspirations?

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