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Mofoluwaso Ilevbare: 3 Tips To Help You Get Through Difficult Conversations



Conversations are an integral part of our daily lives. It’s how we express how we feel, convey what’s going on inside, communicate with the world.

There’s something on your mind you’ve been meaning to ask your boss, but every time the opportunity presents itself, you feel a big lump in your throat. You hear your 8-year-old daughter mention the word ‘sex’ and your heart skips a beat. You submitted a business proposal and haven’t heard anything back, but you really want this deal and although someone has suggested you book a face to face appointment with the investor, you’re too scared. One of your customers never pays you on time for services rendered, and now she has requested for a bigger supply that could cause you losing money if she doesn’t pay on time. You’re ready to take your friendship to the next level but every time you anticipate he’s going to pop the question you always end up talking about something less important. Your son has met a new girl you don’t quite like and their friendship is becoming serious, as a parent you know you should say something about it, but you don’t want to hurt your child’s feelings.

How can you handle these difficult conversations? On one hand, not talking about it is eating you up. On the other hand, the thought of bringing it up makes you develop cold feet. The only way out of your misery is to have the conversation. Here are 3 things I believe will help you:

Convince Yourself of the Purpose and the Benefits
When you find yourself hesitating from having the conversation, ask yourself: “What is the purpose of having the conversation? What benefits will I derive from it? Will it put an end to doubts, strengthen a relationship, or correct a misconception? How can I make this conversation perceived as a win-win? Who else will benefit from the outcome of this conversation? What’s the worst that could happen?”

Asking yourself these questions and finding answers to them may give you the courage you need to initiate.

Prepare and Create the Environment
Before you begin the conversation, consider the factors that can enable a good discussion. Look for the right moment when you feel the other person will not be distracted. However, if finding the right moment is making you procrastinate, you have to do it anyway.

Get on a personal level without pointing accusing fingers. Don’t judge. Your goal should be to have a productive conversation where the communication channel is open and the discussion is less painful (for both parties) than you anticipate. Don’t go into a difficult conversation with a my-way-or-the-highway attitude. Be open to other ideas. Ensure you also have time and are committed to the outcome.

Express How You Feel Clearly and Listen for a Reaction
Using the word “I” can make you vulnerable, but it is the best way to truly express how you feel when XYZ happens or doesn’t happen. It makes the conversation seem personal and not distant.

Speak calmly. Anticipate the possible emotions that could show up and what your reaction should be. Be clear and simple. Manage to let go of any judgements and be open to absorbing the other person’s point of view. Be ready to admit you may be wrong too. Listen with respect and project a win-win option as much as is possible. Inject some praise/positive words into the conversation but focus on the issue at hand.

Bear in mind that not every conversation can be rehearsed perfectly so your emotional intelligence skills will be tested. As the conversation ends, summarise the outcome. If it was with your partner or loved ones, let them know you still love them. If it’s your boss or colleague, approach it from a place of empathy and end it on a professional mode.

Difficult conversations in itself are difficult but if you shift your mindset from the word ‘difficult’ to ‘important,’ from ‘fearful’ to ‘necessary,’ you are in a better shape to handle them. So, don’t shy away. The outcome may not always be a win-win but having had the conversation makes you more authentic. And it can be liberating, too.

Question: What do you struggle with the most when it comes to having day-to-day conversations? I’d love to be able to help in anyway that I can.

Laugh-out-loud Riddle of the Week: Who falls asleep at a bullfight? Post your answers below.

Mofoluwaso Ilevbare, a.k.a. the Unstoppable Life Strategist, is a Best-selling Author, Speaker, Leadership & Lifestyle Coach who works with ambitious women, entrepreneurs and business leaders who want to be unstoppable at work and life without sabotaging faith, family, or self-care.A soulful thought leader, wife, and mother of two, Mofoluwaso loves God, family, coaching, and also has a healthy appetite for chocolate cake. She is a member of the John Maxwell Team, a Cherie Blair Women Mentor and has been featured in the Huffington Post, Executive Women, and Channels TV Nigeria. Visit to learn more about Mofoluwaso and also connect with her on Facebook , Twitter, and Instagram and LinkedIn

1 Comment

  1. Nkem

    July 11, 2018 at 12:04 am

    Thanks for these useful tips. Well appreciated. My biggest hurdle is asking my boss a request especially when it concerns my personal development. I’ll try these tips.

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