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There is No Off-Season for Hard Conversations

Winter, spring, summer, or fall…hard conversations need to happen all year long. We understand that summertime has more of a casual, easy-breezy vibe and there is even a stronger tendency to avoid conflict and to sweep issues under the rug – but that doesn’t mean they don’t exist. Necessary hard conversations never take a vacation, and there is never an off-season.


Executive coaching is all about helping clients identify and prioritize specific development goals, and then creating strategic action plans to help achieve those goals. For almost every client, improving skills around having hard conversations, providing real time and critical feedback, and holding people accountable are at the top of the list. Whether it is snowing or swelteringly hot outside, developing and strengthening these skills is critical to being an effective leader all year round.


This is not the time to take a break and allow things to slide. Successfully navigating crucial conversations is a muscle that needs to be exercised and strengthened consistently throughout the year. Just like there is no off-season for elite athletes, there is no off-season for leaders when it comes to having the tough conversations, leveling up their teams, and driving performance.


Follow the ON Point Action Plan to make sure you are in shape to have hard conversations all year long.

7 Steps to Having Hard Conversations All Year Long

  1. Get a Goal – have the end in mind first, think about what a successful outcome & result looks like; know what you want to accomplish

  2. Know Your Audience – understand the other person’s style, approach & personality to customize your communication appropriately

  3. Plan Ahead – gather your thoughts, talking points, questions & anticipated responses & objections in advance to prepare

  4. Be Timely – have the conversation in real time while the events, circumstances & details are still fresh in everyone’s mind

  5. Give Notice – when possible, give advanced notice, a heads up, or an agenda to avoid a blindside & to allow the person to process & prepare

  6. Coach Them Up – leaders are coaches so treat these moments as coaching opportunities to help your people grow, learn & develop

  7. Follow Up – feedback is never a one-and-done; provide lots of praise if the behavior improves & continue to coach if more work is needed

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