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At Keyot, we’re passionate about imparting our time and wisdom to young professionals, teaching them valuable skills to develop their careers. A topic we often coach is the art of having difficult conversations with coworkers and managers.

Over my career, I have been lucky to work with some exceptional leaders who jump into hard conversations head-on with tact and poise, resulting in conflict resolution, better communication patterns, and stronger relationships. I have seen others who avoid a difficult conversation at all costs, choosing to vent to other coworkers or couch their feedback in such vague terms that the point is never landed.

Here are some tried and true tips for having a hard conversation that leads to a positive outcome for everyone involved:

  1. Define Your Why: Take some time to clearly articulate your frustration or concern and have an outcome goal for the conversation in mind. Come prepared with a specific example or two. (Don’t overwhelm the other person with a long, detailed laundry list of offenses.)
  2. Schedule 1:1 Time: Make time to meet face-to-face or via video within a few days of the frustrating event. Avoiding a conversation can cause frustrations to build and the situation to get worse. (Don’t try to have hard conversations over email/text/instant message. It’s too easy to confuse tone and intent when you aren’t meeting face-to-face.)
  3. Put Yourself in Their Shoes: Consider what you already know about the other person, their communication preferences, and their hot buttons. Assuming positive intent helps put you in the right frame of mind to approach the conversation with generosity and grace. (Don’t use a one-size-fits all approach; tailor to the person you’re talking to.)
  4. Watch Your Language and Your Emotions: If your coworker has done something to upset you, give your self some time to cool off before having the conversation. Make sure you’re coming into the conversation with a calm and clear head. Use “I” words instead of “you” words. Take responsibility for any part you played in the frustration. (Don’t use put-downs or belittling language or let your emotions get the better of you.)
  5. Be Direct and Focus on Facts: Get to the point quickly but allow the other person to brace for feedback. It can help to call out the “elephant in the room” and acknowledge that this may be an awkward conversation. Be specific about your frustrations or concerns without being accusatory.  (Don’t beat around the bush or use vague language that gives too much room for misinterpretation.)
  6. LISTEN! More times than not, coworker frustrations are the result of a miscommunication or misunderstanding of intent. Give the person ample opportunity to give their side of the story and be genuinely open to hearing their perspective. (Don’t get so wrapped up in your planned talking points that you forget to hear the other person out.)
  7. Propose a Solution: Give your ideas for a better way of working together and invite the other person to share their ideas. Wrap up the conversation with a mutual agreement on a way forward. Emphasis your shared goals, make a commitment to each other to have another conversation if the need arises, and to keep an open communication channel between you.(Don’t end on a sour note if you can avoid it.)

Having crucial conversations and giving transparent feedback to a coworker can be scary for many of us, but with these tips, we CAN have hard conversations and come out the other side with stronger working relationships and a better understanding of each other.

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