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0 Navigating Challenging Conversations

Some conversations are downright terrifying. Even if you are a confident person with competent communication skills, trying to fulfill a need without being able to predict the outcome (“Will she say yes?” “Is he going to be upset?”) can be overwhelming. When returning from maternity leave after the birth of my first child, I was fraught with worry over letting my boss know that I’d need to take the 4:50pm train out of the city every day to relieve the babysitter on time. When I tried to find the words, all I could see is how this new schedule made me less. It was a busy Manhattan office where few had children and many routinely worked well past traditional business hours. I agonized over the timing, the verbiage, the perfect rationale. The more I tried to get the request just right, the more I spun circles, moving from anxiousness to avoidance.

Eventually, I couldn’t spend another second trying to perfect this question that I had convinced myself would mark the end of my career. There was a job, a newborn, a train, and a babysitter. No amount of handwringing was going to change those variables. And, as it turns out, my supervisor was great. She just wanted to know if it was okay for her to get in touch with me after 5:00 pm if something came up.

Capitalize on the moment


A lot of us are currently on the edge of transition. Many have summer vacations in the pipeline and we’re beginning our re-entry after many months of working and schooling from home. There might be something you are looking to ask your supervisor but don’t know how to get started. Perhaps you want to work remotely more often, take time off for a trip, or ask to be considered for a new position with more responsibility.

We’ve spent over a year accomplishing our work completely differently than ever before which leaves us with a strong position for any changes we want to make. If you are seeking more authority or responsibility, articulate the way you’ve navigated the recent obstacles. If you are hoping to expand your remote working routine, quantify the output you managed this year from your home office. Be respectful and persuasive.

Take the conversation into your hands


In the TED Talk series “How to Be a Better Human” series, Daryl Chen says that sometimes we avoid difficult conversations because, even if something hasn’t been going our way for a while, we’re worried we might make things worse. He urges us to “move toward- not away” from the conflict. Be informed but stay humble. When asking for something, ask the other person about their experiences. Keep quiet, especially in the beginning. Once you address the question (for example, transitioning to a new project?) be quiet for a few minutes. Give the other person a chance to talk. Try to see things from their perspective. Why might there be hesitation on their part? What other issues could they have going on in that moment?

If you sense things aren’t going your way, try to slow the dialogue by paraphrasing the other person’s points. Taking time to show that you are listening and thinking critically demonstrates your genuineness. A recent Harvard Business Review article described how asking questions can also be a persuasive tool. It requires humility to give the other speaker space to elaborate on a position that contradicts your own. They said, “When you listen deeply and sincerely, others feel less of a need to resist you in order to be heard.”

Prepare and research

No matter what the nature of your conversation, take the time to prepare and practice:
Understand your organizational landscape as it relates to your request. What are the trends? Do you know anyone in your situation? Can you ask them about their experience?

  1. Explain how this change could help you do your job better. What are the benefits to the organization?
  2. How would it make you more productive? Is it a good business decision? If so, what is the return on investment?
  3. Write a workplan. How might you adjust your day to absorb this change? What would each day look like in the coming weeks? How will you take charge of this?
  4. Explain how you will prove your success. How will you demonstrate a positive outcome? How will you stand out?

Articulate- for yourself- why this matters

If you’re still having a hard time getting started, jot down three reasons why this is important to you. Project how your situation might be different in a few months- or even after a year- if things work out the way you want. Why is this worth the conversation?