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Tough conversations tripping you up?

Have you ever had to face up to a tough and honest conversation with your boss? Going into it, your feet are tingling, hands shaking, it’s hard to breathe and you can’t think straight.  We get it, those nerve-wracking conversations are hard to face.  But done well with some pre-planning, they can become a most productive feat and are likely to alleviate some of the problems you needed to talk about in the first place!                                            

When something is really important to you or upsetting, nerves are a difficult thing to combat, and all that emotion can have a field day!  And while we can’t promise that things will always go the way you imagined or hoped, the best thing you can do is ready yourself for all possible outcomes.   

The only thing you can control are your own actions and words, so it’s best to be prepared and clear about what you want to get across in the conversation. It could be a number of things: maybe you feel your workload is too heavy for one person, maybe you want to ask for time off during a known busy period at work, or maybe it’s time for a pay rise. 

Respectfully sharing your perspective, listening to feedback, and having a desired outcome in mind from the beginning is going to be crucial in communicating effectively.

  1. Ready to get the ball rolling?

    The first thing to do is to think about how you’re going to approach addressing your superior. You're going to want to do at a time and location that is most convenient to them.  Probably not ideal timing to launch on them the second they walk into the office in the morning or catching them in the hallway when they are running late to a meeting.  Think about your work setting and their work style and figure out the best time and place to book in time to have a conversation, whether it’s casually in the staff kitchen, or via email or text.  And briefly let them know what it is that you want to discuss during the planned meet-up–but don’t be tempted to go into it there and then, wait for the right time!  
  2. Pin down what you want to discuss and how to go about it.

    The last thing you want is to be ruled by how you feel during the meeting, so it’s important to put some time and planning into what you actually want to convey and how you will communicate, especially if its to do with a grievance.

    Regardless of how you feel, it’s critical to conduct yourself with poise and respect in this type of meeting — sure, you can show where you feel wronged, but do it in a way that’s conversational rather than an attack.
    • Get it on paper: Write a list of things you want to discuss and prepare for every possible answer that your boss may have so you’re prepared mentally to respond to any curveball.
    • Prioritise! If there is more than one thing you want to cover, rank them in the order of their importance-meetings don’t always go as planned, phone calls or urgent interruptions can take precedence so plan to get the most important points out first.
    • Practice makes perfect. Use your phone to video yourself practicing the conversation (one-way of course): do you look poised calm and confident, or are you a stumbling nervous wreck? Keep at it until you feel ready to face the real thing.
  3. Getting right to it

    D-Day is here. If you’re feeling nervous, congratulations – you’re normal! Confrontational conversations are never comfortable, but the odds are that with all of your preparation you’re on the right track. Sometimes the only way through a difficult conversation is, through it. Stay humble, keep breathing, and stick to your plan.
    • Keep calm and carry on. You may not get the outcome you hope for, but you’ll grow through this process.
    • Be friendly, but direct. Don’t beat around the bush. You will appear more confident and professional if you clearly state why you’ve called the meeting and what you’d like to discuss.
    • Listen more than you talk! Try to keep emotions on the back seat during the conversation. Confrontational dialogue is often unhelpful, so go into the conversation open to learn. You may find that the whole disagreement is based on a miscommunication that you can easily clear up.
    • Work towards a compromise. If you go into a conversation hoping to win a fight, often everyone loses as emotions take over and cloud reason. A compromise requires giving up ground, but will usually lead to more positive future interactions. A compromise may even be better than the initial intended conversation so keep your options open.
  4. Where to from here?

    Well done! You faced your fear and had the awkward conversation you’d been putting off. Whether it went exactly to plan or not, you’ve taken a brave step forward and presented yourself as an active, engaged employee. Once you’ve had your initial conversation, if a conclusion hasn't been achieved, you may need to give your boss time to consider what you brought up. Rather than putting pressure to get your own agenda across, be patient. If a significant of time has passed, consider following up with a simple, professional email:

    Dear _______,

    Thank you for meeting with me last week, I appreciate you taking the time to speak with me about my concerns. What are the next steps regarding the items we discussed? I value your opinion and would like to know your thoughts about the best way to proceed.


    (Your name here)

    Keeping your email simple, but direct shows that you are connected and value forward momentum without seeming like you have a bone to pick. If the answer isn’t what you were hoping for, you’ll need to reevaluate, but you can cross that bridge when you come to it. If you conduct yourself professionally and clearly state your concerns, you can be certain that you’ve done your part.

Don’t get down!

Tough conversations are part of life, and done right, they’ll help you grow important muscle to help you progress and thrive in your personal and work life.  Sometimes, working through something with a manager can make space for positive conversations and a totally different trajectory.

Remember to plan ahead, keep your cool, and approach your manager from a posture of respect. No matter how things turn out, you can be proud of the way you handled the situation. Cheers to you!

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