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Stopping the Should’ve, Could’ve, Would’ve

by Thuy Sindell, PhD. and Milo Sindell, MS.

Do you get annoyed like I do when someone responds to a question or observation about his or her behavior with, “Yah, yah, yah, I know I should do a better job at ___.”? Initially, you have a feeling of guilt for making the person feel self-conscious for his or her poor work. Then, without meaning to, you let your cynicism set in. You don’t want to believe that the other person has no intention of doing what they say they will do and then you feel like a bad person to think that. But it’s true, right? More than likely, they aren’t going to do it!

So how do you stop the “should” conversation and move it to one of commitment and change? That means you are going to have to be a little uncomfortable and start asking follow-up questions. Specifically, I called these “coaching- integration questions.”

So let’s first define the difference between coaching and mentoring because these terms are often used synonymously. Mentoring is when you come from your own experience and perspective and share your knowledge with others. You can do this with statements: “When I was trying to bolster my career, I did this.” You can also do this through feedback: “I noticed that when you gave your presentation you did this, and it could have been better if you did that.” This is all giving someone your opinion based on your personal experience. This person you are mentoring will typically respond with “You’re right. I should do that more next time,” which leads us back to the lack of commitment that drives us all crazy. What is the point of wasting our breath and time when the other person doesn’t do it? That’s when coaching becomes important.

Coaching is when we come from the other person’s experience. We get at that by asking questions about what their thoughts are. So in this example, you want to ask questions about what opportunities exist for them to try it differently. Then ask questions about what specifically they will do and how will they remember to do it. The answers to all of these follow-up questions must come from the other person. You are helping them chart a path for what, when, where, why and how they will do it next time. It may feel like you are micromanaging the person, but really all you are doing is asking follow up questions to help them move past “should.” So you might say, “You agree you should do this, so let’s make it more concrete for next time. When is your next opportunity to give a presentation?” Use their acknowledgment of “should” to your advantage.

So now that specific opportunities and actions have been identified, it is up to you to play the coach role and ask the “coaching-integration questions” that helps the other person internalize the feedback and create action. When people tell you step-by-step what they will do, they are making a public declaration, which increases the likelihood that they will follow through and take accountability for their own actions. So get uncomfortable and ask those follow-up questions instead of allowing yourself to feel cynical and frustrated. Regardless of who the person is in your life (your employees, manager, or even spouse), do them a favor and ask the hard questions.

Conclusion: Practicing these two simple steps of not accepting “should” as good enough and asking the person follow-up questions will help them take action and move from should to will. In your next conversation with a colleague, look for opportunities to coach and help reduce the “should” conversations.

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