The art of navigating a difficult conversation with your boss

By Amy Burton|07 June 2017

If there was an award for ‘cramming-the-most-difficult-conversations-with-a-boss-into-the-early-stages-of-a-career’, I think I’d be in the running for the winning prize, writes Amy Burton.

In my first few years as a young lawyer at a big corporate law firm, I had to tell my boss that I’d misplaced an original signed agreement, that I wasn’t coping with the gruelling work hours, that I needed to take a chunk of time off to recover from a mental health issue and that I was having issues with a senior colleague.

The worst thing about each of these conversations was the lead up. I would allow whatever issue was affecting me to completely consume me. I’d have sleepless nights imagining how awful it was going to be when I finally fessed up to my boss; I’d isolate myself from my work buddies, avoiding our morning coffee runs and Friday night events; and I’d stop exercising and stay really late at work in the hope that the extra ‘face time’ would offset any negative repercussions that my pending disastrous conversation was going to have on my future career as a lawyer.

Over time, I’ve learnt a thing or two about reducing the negative impact that these conversations have on my wellbeing. Given that most young lawyers are going to face an awkward conversation with their boss at some stage, I thought I’d share some of my tips.

1. Don’t put the conversation off and don’t label it as ‘difficult’

Ever tried pulling a band aid off your leg really slowly? Or putting off seeing the dentist when you’ve got a throbbing toothache because you’re scared they’re going to tell you that you need a root canal? It really hurts, doesn’t it? So does putting off a difficult conversation with your boss.

Sure, there’s no chance that it’s going to be a walk in the park to tell your boss that you’ve stuffed up an important task, especially when there’s financial pressures at stake. However, it’s not going to make it any easier if you keep telling yourself that it’s going to be ‘horrible’ or ‘the worst thing in the world’. Plus, the longer you draw it out, the more stress and anxiety you’re putting on your body. Just remember, the sooner you get the conversation off your chest, the sooner you can fix any issues and move on.


2. Speak to a trusted senior colleague

There have been a few occasions where I’ve thought that I’ve completely stuffed something up and have had a massive freak out about telling my boss. Then I’ve mentioned it to a slightly-more-senior colleague, only to have them laugh and say, “Oh, I did the exact same thing when I was a graduate.”

It’s no big deal! Just do X, Y and Z, and it’ll be fine. It’s also likely that they’ve worked with your boss for quite a while, so they’ll be able to give you some suggestions about the best way to bring the issue up.

3. Have a chat with your Human Resources team

It took me far too long to realise that the Human Resources (a.k.a People and Development) team are experts at managing difficult conversations in the workplace. Before you speak to your boss, ask your HR representative whether they have time for a quick chat. You’ll probably be surprised by how non-judgmental and willing they are to help you navigate the difficult conversation.

If you’ve got a particularly big issue, your HR representative may even offer to attend the meeting with you and your boss. That way, you’ve got someone there to support you and to step in if you start getting a little bit emotional. It happens and it’s a sign of your professionalism and maturity that you’ve had enough foresight to ask an impartial third party to get involved.

4. Plan what you want to say

It sounds really simple, but it makes a huge difference if you take the time to jot down some key points before your conversation. You may want to put the list together with a trusted senior colleague or HR representative so that you cover everything off. Take the list into the meeting with your boss; it’s amazing how easy it is to forget really important issues when you’re feeling stressed and pressured.

5. Flag to your boss that you’d like to arrange a time to discuss an issue with them

Ever had someone interrupt you while you’re deep in thought, to ask you a question that seemed to come out of nowhere? You probably didn’t respond well. The same thing is going to happen if you spring a difficult conversation on your boss while they are in the middle of reviewing a contract worth $10 million for an ASX listed company. There’s no way that they are going to see it coming and probably won’t respond appropriately.

Rather than make the already difficult situation worse, send your boss a short email asking them whether they have some time for a catch up later. Be aware that your boss may see your email and freak out that you’re about to resign, so if they call you into their office immediately after you send the email, don’t be afraid to say that you’d prefer to talk a little later. You don’t want to be put on the spot.

6. Go for a walk beforehand

It’s amazing the difference a 15 minute walk can make before a difficult conversation. It’ll give you time to gather your thoughts and calm yourself down. If you’re taking your HR representative into the meeting with you, this could also be a good opportunity to meet with them to go through your list one last time.

7. Be honest

A little bit of small talk about the weekend footy results is fine, but don’t beat around the bush. Your boss is probably an incredibly busy person and will likely sense that a difficult conversation is on the radar. Tell them why you’re there, clearly and efficiently explain the issue (don’t forget your notes!) and allow them to respond without jumping in to try to defend yourself.

8. Don’t take any negative feedback personally

Let’s face it, if you’ve stuffed something up then your boss isn’t going to give you a big hug and tell you that everything is going to be okay. Similarly, if you’re resigning your boss is unlikely to give you a high-five and congratulate you. That’s what parents and friends are for. For the duration of the meeting, you may need to grit your teeth and accept that your boss is going to say a few negative things. If possible, ask them for some constructive feedback and take some notes. This could be a perfect opportunity for you to learn something really important.

At the end of it all, remember that your performance at work – and the occasional mistake – does NOT define who you are as a person and does NOT detract from all the brilliant things you’ve achieved so far in your career. It may help to have a work buddy or friend on call afterwards to remind you of this.

9. Your boss is probably going to respond better than you expected

On the other hand, if you’re battling with a personal issue your boss is probably going to respond better than you expected. In fact, they’ve probably already sensed that something is up and will be relieved that you’ve trusted them enough to speak up. When I finally plucked up the courage to have a particularly difficult conversation with my boss, I was taken aback by how understanding and supportive he was about the situation. We started meeting for coffee once a week to touch base and consequently formed a really great working relationship that may not have developed without that initial conversation.

10. Do something that makes you happy

Sure, we spend a lot of our lives at work but that doesn’t mean that we should turn our backs on our hobbies, passions, families and friends. Schedule in some ‘you time’ after a difficult conversation, to remind you of the brilliant things in your life. If you can’t think of anything that makes you happy, then I really encourage you to consider speaking to a counsellor or psychologist.* They’ll get you back on track, I promise.

*Most firms have an Employee Assistance Program (‘EAP’) program that your HR representative can tell you all about. Otherwise, please don’t be afraid to visit your GP or give Beyond Blue or Lifeline a call.

Amy Burton is a senior associate of Salvos Legal Humanitarian, a law firm dedicated to providing life-changing free legal services to people in need. A finalist in the Lawyers Weekly 30 Under 30 Awards, Amy is also a Member of the Law Society of NSW's Human Rights Committee and a number of NSW Young Lawyers’ committees including the Wellbeing Working Group, which organises regular events and programs to promote wellbeing among young lawyers in NSW.

The art of navigating a difficult conversation with your boss
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