Having a difficult conversation with a superior is not something you get taught how to do at school or university. But like so many professional skills, the long-term ramifications of your performance can have a significant impact on the trajectory of your career.

Some people are born fast, some handsome, some funny, some intelligent. And some people are naturally gifted at speaking to their superiors in difficult conversations – whether that be an appraisal, a grievance, or something else – they just seem to know what to do.

But what if you don’t? What if you find yourself grasping hopelessly for words, flushing red, intimidated by the thought that you are inferior, you’re about to say something stupid, you’re wasting their time?

Well, there are some practical ‘anchors’ you can embrace which should give you more confidence in those conversations, and at least level the playing field – if not give you an advantage and allow you to keep your cool.

Since the best way to learn nothing is to try to learn too much, let’s just pick three of the most useful points.

Eye contact

Sight is such a prominent part of our psychology that developing children will often believe that if they cover their eyes, they become invisible. As adults, maintaining eye contact will reduce our cognitive processing power, making it harder to simultaneously think and speak, and maintaining eye contact with another person will also make us feel more self-conscious.

So why is it worth maintaining eye contact during a difficult conversation? Mostly, because in the context where you are speaking with a superior, about any subject, it would be strange not to. And when someone speaks to us and maintains eye contact (as opposed to averting their gaze), we instinctively assume that person is more sophisticated and has a greater ability to maintain self-control and act morally.

We are also more likely to believe what they are saying is true. Taken together, these factors give your words an amplified power to persuade – simply, a steady gaze gives you authority.

Yes, it is also true that staring at someone intensely can come across as aggressive, or even like you are trying to appear honest (and so, ironically, seem deceitful) – so don’t do that. Studies suggest that the optimal length of time to maintain eye contact is just over three seconds (which is longer than you might think).

As a rule of thumb, then, try maintaining eye contact mainly when you or your superior is making a point in the dialogue, and then look somewhere else in between these moments.


Many of you will have already learned that decisions rarely happen in meetings; usually the decision has already been made and the meeting is just a venue at which it is being recorded. The reason for this is because everyone is busy – it is rare that the contents of a discussion in a meeting will derail the preconceptions the attendees have brought in with them – and they probably have another meeting to rush off to.

So what to do? You should arrange the meeting well in advance, making sure your supervisor has time to listen to what you have to say, and isn’t going to be focused on something else. Check their diary (if you can) to ensure you are picking a suitable moment, or even ask them when would be a good time. Sometimes, combining a meeting with a meal like lunch will help to ensure you have their full attention.

Oh, and never pick a Monday. And don’t pick first thing in the morning, because then that means the attendees have to get in early. In fact, studies have suggested the best time for a meeting is 3pm, and preferably on a Tuesday.


It is important to ensure that you are offering solutions – don’t just bring problems to the discussion. The meeting might be about a problem, and your superior might not even want to hear your solution(s); but make sure you have some, just in case.

Superiors are busy, and like people who come to them with a problem solved. Not only does that show initiative to them, but you will feel more confident in the meeting knowing you have something productive to add if necessary (particularly if you are worried you might be put on the spot).

Ultimately, your proposed outcomes for the meeting should make your superior look good. It sounds obvious, but they will be much more inclined to agree if what you are proposing benefits them – don’t forget they have to answer to someone too.

Jonathan Hodge is a commercial disputes solicitor at Aquabridge Law in Chelmsford and an executive committee member of the Junior Lawyers Division.