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3 steps to a breakthrough conversation

Simply investing 15 minutes of planning and a little bit of practice is all it takes.

Photo by Luca Laurence on Unsplash

Most managers and entrepreneurs alike dread having difficult conversations with their employees. 

I’m here to tell you that If planned properly, not only will you save time and have a productive conversation but also inspire your employees to take positive action. Don’t believe me? Read on.

Think of following 3 steps (P.D.F) as the recipe for a successful feedback conversation

  1. Plan your conversation
  2. Deliver your conversation
  3. Follow up on for commitment


1) Plan your conversation

I see most managers making this critical mistake of skipping the planning phase and jumping right in. Big mistake.

Planning your feedback goes a very long way when it comes to having a constructive dialog with your direct reports.

 Start with the following 4-point checklist to plan your conversation.

Writing down your answers to the following questions will further clarify your thought- process. (Time required: ~10 minutes.) 

  1. Identify one specific behavior that needs to be corrected or reinforced.
  2. What is the impact of this behavior and who is it impacting?
  3. What specific outcome do you want your employee to produce as a result?
  4. When will you deliver this feedback? (Date and Time?) 

2) Deliver your conversation

Now, lets dive into the tricky part of delivering constructive feedback to the person in question.

Managers tend to struggle when it comes to providing constructive feedback. It’s always challenging to have these types of conversations. Following are some proven ways of tackling this.

  1. Describe the behavior (Answer to question #1 above)
    • When you are consistently late…..
    • When you respond on time
    • When you check that document twice….
    • When you don’t respond to my emails…
    1. Describe the impact of the behavior (Answer to question #2 above)
      • Here’s what happens, we all miss our deadlines and the customer loses faith in us
      • Here’s what happens, you elevate us in the process and demonstrate that patience in a heated exchange goes a long way
      • The customer appreciates your due diligence and truly appreciates our relationship as an elite enterprise partner
      • You miss important updates from my side, these updates are designed to help you and our customers.


    All great leaders and entrepreneurs understand and leverage the power of questions. Great questions have the potential of cutting through the clutter and getting to the heart of the matter. Peppering the following questions in the middle of your conversation will reveal helpful information about your employee and make your conversation richer in substance.

    • How do you see this situation?
    • What do you think is the reason behind it?
    • How might you have contributed to this situation?
    • What impact is this having on you?
    • If you could identify 1 issue contributing to your performance. What would it be?

    Once you’ve asked your question, let it land and provide your employee the space to answer. Watch your tone and don’t let your emotions get the best of you. Try to stay calm if/when the employee pushes back. Lastly, remind yourself that you’re here to help the employee succeed.


    3) Follow up for commitment

    In the world of feedback, it doesn’t matter what you say – what really matters is what your employees hear. Make sure to close out the conversation with these 2 questions

    • What specific actions will help you achieve the outcome we’ve discussed?”

    The answer to this question will influence your employee’s understanding of the conversation you just had. It eliminates confusion or misunderstanding of what you’ve discussed.

    • “How can I support you?”

    The answer to this question will give you concrete steps to support your employee’s growth while gauging their motivation level for taking action. It ensures alignment and that you are a trusted guide in their journey.

    After a couple of days have passed, make sure to remind your employee of your observations. If the employee has improved, call it out by reinforcing it with positive feedback, if the behavior still persists, my advice is to remind the employee of the commitment both of you agreed upon and help them understand how their behavior hasn’t changed. Offer to help them in their journey.

    The onus of delivering feedback rests on a leader’s shoulders. The worst kind of feedback is no feedback at all

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