Difficult conversations you’re likely to have in your first year at work

Difficult conversations are inevitable over the course of your career. Although they may always feel intimidating, you can pick up techniques and approaches to improve the outcomes.

At the very beginning of your career, these conversations are generally tipped in favour of the other person; as a junior member of the team, you have to work harder to ensure that these difficult conversations go the way that you want. No matter the conversation, you must determine its purpose and the outcome you’re hoping to achieve to ensure the conversation goes your way. More information on handling difficult conversations can be found on CMI’s Knowledge Bank.

Here are some typical conversations you might have very early in your career, and how you might handle them.

"I’d like to talk about my development"

Ambition is a fantastic attribute, and it’s great to have career aspirations to show that you’re committed to your development – but how do you talk about this at work without making your manager feel like you’re looking for a new role?

Before you start looking much further into the future, there’s work to be done in your first job. You need to have some understanding of your current strengths and weaknesses (ask colleagues for feedback if you’re not sure), and use that as a foundation for a conversation about your development. Talk about your current role and work with your line manager to set some goals to help you grow within it, such as higher targets, personal achievements, or more responsibility. This shows a willingness to do well without sounding like you’re already eyeing your next opportunity.

"I’d like a payrise"

Asking for a payrise involves outlining your value with confidence – something that a lot of people struggle with. An estimated 70% of people will experience imposter syndrome in their life – and it’s hard to sell yourself when you feel like a fraud.

Jot down evidence of the good work you’ve done, note successes as they happen and how they’ve benefited the team and company, so you have a body of evidence that demonstrates why you deserve an increase in pay. You may want to approach your manager ad-hoc to discuss this, or you may want to wait until a performance review to give your manager some time to prepare their own notes on your achievements thus far.

"I’ve made a mistake"

These things happen to everyone – mistakes and failures are a part of working life. The important thing is how you respond to them. As hard as it might feel, you should own your mistakes – deflecting blame will not go down well with your line manager. 60% of employers that were surveyed for CMI’s 21st Century Leaders report identified taking responsibility as the most sought-after behaviour, with being honest and ethical coming second with 55%.

Once you’ve outlined what went wrong, you should follow it up with some possible solutions. It doesn’t matter if your boss solves the problem in a different way – it’s about your attitude. You should also demonstrate that you’ve learned from the experience, and that you’ve taken those learnings on board. All of this will demonstrate a positive, solutions-focused, growth mindset.

"I don’t like your management style"

Offering direct feedback to your superior is never easy, but sometimes it’s necessary to help create a mutually respectful relationship.

This is not something to blurt out at any time – you must choose your moment carefully. A discussion with your line manager about your performance is a perfect opportunity to bring up any misgivings or feedback you may have. Your line manager may even ask you directly for feedback.

Even in this case, it’s important you frame that feedback in the right way. It has to be positive and focused on improving the relationship, not merely criticising your boss. Suggest ways in which your working relationship could be better, and think about how you can both work to achieve that. Frame this with care, concern, and empathy, and it should build respect between you.

"I’ve got another job"

This is a conversation that often feels like it’ll be more difficult than it actually is. As disappointed as they might be, your boss will most likely be happy that you have found an exciting new opportunity. You want to make sure you leave on good terms – you never know when you might cross paths somewhere down the line. Tell them that you appreciate how much your manager and the company have helped you grow, emphasise that you are grateful to have worked there, and give it your all until the end.

Where it can get trickier is when you actually want to stay, but want your company to offer you more money. This is always a bit of a gamble – you don’t want to try this too often, or you’ll start to seem a little too money-driven. Treat it as a problem for you and your manager to solve together – explain that you’d like to stay but the offer is too good to ignore, and see if it would be possible to match the offer so that you can stay.

Each of these difficult conversations should pave the way to a resolution. Have a possible suggestion for action plans before you go into each one, and as the conversation progresses work your way towards that resolution. Not every situation will go your way, though, and it’s important to understand that not all problems can be solved immediately.

To prepare for your difficult conversation, see how you can boost your communication skills.