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5 tips on having a career discussion with your boss

Do you have the world's best boss, like Michael Scott (Steve Carrell) in The Office? That makes having tough conversations easier. Image: NBCUniversal Television Distribution

Initiating a career discussion with your boss can be a daunting challenge.

This often arises from uncertainty of how to approach the topic and fear of a negative reaction.

It is worse if your boss has poor interpersonal skills and a lack of emotional intelligence (EQ), over controlling tendencies or is a down right bully.

Irrespective of the leadership style of your boss it’s your career and it’s up to you to manage and drive it, this requires initiative and energy on your part.

Opening up a dialogue about your career aspirations is the best place to start.

Formal opportunities might exist to do this such as performance and development reviews or when a job vacancy arises.

Quite often it may require a deliberate move on your part to schedule a career discussion or take advantage of chance opportunities as they arise.

In either case you need to be prepared and ready to seize the day by promoting your career development agenda.

Here are five key tips you’ll find helpful.   

1. Preparation is key - help your boss to help you  

Before opening up a career discussion know where you’re going and why as well as how you plan to get there by having a clear picture of your career goals and pathways. Communicating this succinctly is essential, so be clear about the priority of your preferences.

When asked what you want for your career or what your ideal job is be prepared to answer this with clarity including desired time frames.

Your boss will be better able to support you if you’re clear about where you want to be heading and if you have realistic and time-framed career goals along with a well thought out and concrete plan of how to reach them.   

2. Pick your timing and place

Always consider your timing and the situation when discussing your career. When it comes to your career development this is a crucial conversation and you want to make the most of every interaction with your boss on this topic. 

Career meetings may include sensitive topics that require careful and thoughtful discussion from both parties. Make sure the discussion is held in a suitably private environment away from conversation disruptors such as drop in visitors.

Offices that resemble a ‘fish bowl’ should be avoided. Also make sure phones are set to silent and email alerts are disabled.

Additionally, if your boss appears stressed or overwhelmed by other events when you’re due to meet then I suggest rescheduling to another time! These can all be unhelpful and frustrating distractions when you’re discussing your career. 

3. Be open and transparent 

Assume positive intent and approach any career discussion with an open and transparent approach while encouraging your boss to do the same. This will set a constructive foundation for the meeting to achieve a successful outcome.

That said, also have in your mind what a good outcome would look like, what would have happened? Be clear and upfront about your objectives for the discussion and importantly check for agreement with your boss. 

4. Build your case logically 

Make sure you can back your career aspirations with sound logic and evidence. This means being able to clearly articulate your values, career drivers, attributes, behavioural competencies, skills (transferrable and technical) and achievements that support your career goals and aspirations.

Avoid waffle.

Have a good grasp of those aspects of your profile that indicate your potential such as attribute based competencies. This is particularly important where you’ve not had the experience to demonstrate behavioural competencies such as leadership etc. This may help your boss to see opportunities not previously considered.

5. Consider development needs

Know your capability gaps and be prepared to discuss your development requirements. This includes additional training/professional development, qualifications, learning on the job and coaching/mentoring or some combination of all of these that would be valuable in helping you achieve your short and long term career goals.

Again remember to be realistic, practical and cognisant of your employer’s policies with regard to employee development. 

Bringing it all together

Make sure you document your career goals, strategies and development in a written career plan with clear actions and dates for achievement and share these with your boss. This will demonstrate your commitment to your career development and help your boss to understand your career aspirations and support you in realising them. Then start the conversation!

Greg Smith is an expert in career development, talent management and organisational leadership. The co-founder of HR consulting firm, deliberatepractice, he helps aspiring, emerging and experienced leaders to develop their everyday leadership skill set. He is the author of ‘Career Conversations: How to get the best from your talent pool’ (Wiley).  Find out more at