July 9, 2024

Hi Tina,

“What is your biggest pet peeve?” That was a question I asked a CEO during an interview I had a while back. He was stunned by the question and replied, “That’s a great question, I’ve never been asked that before,” then he proceeded with his answer.

My point in asking the question was to find out what bugs him. If I do something irritating to someone, and they don’t address it, how will I know to stop doing it? It’s hard to say things that aren’t easy for others to hear.

Read on to discover ways to make the most out of difficult conversations.

To your success,

Tina Asher
Business/Career Coach • Trainer • Author
Build U Up Consulting

Say the Hard Thing: How to Have that Difficult Conversation

Saying the hard thing can be one of the most difficult things we ever do. For many of us, just thinking about doing it can cause worry, fear, and stress. The good news is that getting these conversations right has more to do with planning and practice than saying “just the right thing.” And when we dare to broach these hard topics with other people, there are often hidden rewards.

The Benefits of Speaking Up

Difficult conversations have the power to get you what you really want from life. They can clear the air between you and someone else. And they can give your self-esteem a real boost.

Revealing how you feel and what you want is a life-long practice that sets you up for more good things to come. Regardless of what happens or how the other person responds, making your true self visible will only make you stronger, healthier, and more at peace with yourself.

Setting the Stage for a Productive Conversation

Bring it up. It’s wishful thinking to hope that the other person will broach a hard topic. In some cases, he or she may not even be aware of the need. That means, like it or not, it’s up to you.
Be clear on your intention. Are you discussing a sensitive topic to make a decision, reveal what you’ve already decided, make a request, or something else? Being clear about why you are having the conversation—and what you hope to get out of it—will help you frame what you’re about to say.
Be mindful of your mindset. Sidestep the tendency to blame and assume you know exactly what is happening. Leave room in your frame of mind for discovery and revelation. Stay curious. Remember how much you care for the person and envision how you’d like your relationship to be after the conversation.
Rehearse. It can be helpful to practice your conversation by writing in a journal or talking it through with a trusted friend or therapist. This will help you become more familiar with your feelings and point of view, and help you relax before you say the hard thing.
Set the tone: Use “I” messages. “You” statements tend to assign blame. For example, rather than saying, “You hurt my feelings,” it is better to use an “I” message and say, “I feel hurt.” If you’re afraid, say what you’re afraid of at the beginning of the conversation. For instance, “I’m scared that you won’t like me anymore or that you’ll go away, or that we won’t be friends anymore after this conversation.” Then take a deep breath and begin.

Saying the hard thing is like any other exercise: every time you do it, you’re building muscle…and your hard work will unquestionably pay off in more meaningful relationships.

In case you wondered, the pet peeve for that CEO was that he hated receiving emails addressed to him and were also copied to a string of additional employees, and yes I did get the job!

Helpful Resources

Managers & Leaders: Download this free guide to discover where you might have opportunities to become a better boss.

Career Help: Unsure about your job? Download this free tool to assess your current career and see where you might be out of balance.

Connect with Me: Ready to transform your career and life? Take the first step toward a brighter future today. Click here to schedule a complimentary Strategy Session, and together, we'll uncover the key steps that will lead you to a more fulfilling and rewarding journey ahead.

Tina Asher
Career Coach • Speaker • Author

With 20+ years in leading, training, sales management, and coaching, Tina Asher brings a broad skillset to helping busy professionals elevate their success. She holds certifications with one of the world's leading sources for science-based, validated assessment and coaching tools. She is a member of the St. Louis National Speakers Association and a graduate of the National Speaker’s Academy. Tina is passionate about serving others to reach their full potential while balancing a full and productive life.

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Say the Hard Thing: How to Have that Difficult Conversation

The Benefits of Speaking Up

Setting the Stage for a Productive Conversation

Recommended Reading

Helpful Resources