8 steps to having a confident career conversation with your manager

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8 steps to having a confident career conversation with your manager

By Ellen Scott

Updated 2 years ago

4 min read

How do you have a genuinely helpful chat with your boss about your goals? Antoinette Oglethorpe explains. 


It’s easy to fall into the trap of only ever chatting with your manager when there’s a problem. You’ve got too many pointless meetings, your workload’s getting on top of you, someone’s being annoying – that sort of thing. We get why; we’re all busy, but keeping your conversations only about problems means you’re missing a trick. 

Instead, if you’ve got a good, supportive manager, it’s well worth booking some time to have a chat about the future: your progression, your development – all that fun stuff.

“Your career, much like your personal development, is ultimately your responsibility,” Antoinette Oglethorpe, a career coach and author, tells Stylist. “You’re the driver of your own career, and as such, it’s essential that you take the initiative to engage your manager in a career conversation. This critical discussion will help create a connection between your aspirations and your organisation’s needs, resulting in a win-win development plan.”

That sounds good to us, but how do we make sure that a chat with our manager is actually fruitful? Oglethorpe shares her eight top tips ahead. 

Prepare, prepare, prepare

Don’t just roll up to a meeting with your boss with absolutely zero plans for what you want to get out of it. “Preparation is key,” Oglethorpe says. “Approach your career conversation with the same rigour you would apply to a major presentation or project. 

“Reflect on your current career situation, pinpointing what you are happy with and what you would like to change. Identify the skills you enjoy using, the values that are important to you, the work environment you prefer and your idea of success. Understanding your strengths and weaknesses is critical to shaping a vision for your future.”

Establish a dedicated meeting

A talk about your future goals isn’t something to just tack on to your usual catch-up. Instead, mark out your progression discussion as its own dedicated meeting, giving yourself space to focus entirely on your career growth. Be clear with your manager that that’s what you’re keen to talk about, so they can come prepared, too. 

Start on a positive note

Oglethorpe recommends: “Start the conversation by expressing your gratitude for the opportunity to discuss your career progression. Clearly articulate what you enjoy and the areas you hope to develop. This proactive attitude showcases your ambition and commitment to the organisation.”

It’s a good idea to kick off with this message, making it clear you’re not talking about the future because you’re in any way miserable with the way things are now. 

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Discuss your journey so far

Once you’ve kicked off on a positive note, it’s time to reflect. 

“Your experience to date provides a foundation for self-awareness and insight,” Oglethorpe notes. “Discuss your learnings and experiences, reflecting on how they’ve influenced your career perspective and contributed to the organisation. This gives your manager a clear view of your capabilities and value.”

Ask for feedback

Next, make the most of the chance to get your boss’s thoughts. This isn’t a time for you to monologue about your greatness and your dreams, but to use your manager’s insight to your advantage. 

Oglethorpe tells us: “Embrace a growth mindset by seeking your manager’s input on your performance and areas for improvement. Accepting feedback is a sign of maturity and eagerness to progress, so approach it with an open mind and positivity.”

Outline your vision of future success

What does success look like to you? What do you really want

Oglethorpe recommends: “Describe your career aspirations without limiting them to specific job titles or positions. Instead, explain your ideal future work experience. Describe in as much detail as you can the responsibilities, achievements and capabilities you hope to develop. This gives your manager a clearer understanding of how to support you and align your career growth with organisational needs.”

Explore potential career routes

“There are many paths to a career destination,” Oglethorpe says. “Discuss potential opportunities within your current role or elsewhere in the organisation and explore how you can navigate the company’s structure and politics. Understanding the organisation’s processes will empower you to increase your visibility and leverage different options and opportunities.”

Create a development plan

Done all that? Now it’s time to create a solid plan. 

“End your conversation by creating a career development plan,” Oglethorpe suggests. “This should outline practical steps towards your career goals, such as skills to develop, experiences to seek and projects to undertake. A robust plan is ambitious yet achievable, pushing your boundaries while remaining realistic.”


Antoinette Oglethorpe is the author of Confident Career Conversations: Empower Your Employees For Career Growth and Retention published by Rethink Press and out now.


Images: Getty

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