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How many times should I have a conversation before I give up?

Barbara HauserBarbara Hauser is a Master Trainer.

Q I’ve had successful crucial conversations with someone several times now and nothing much has changed. How many more times should I have this conversation before I give up?

A I’m sure all of us have had this question come up in training in one form or another. There are many ways to approach a situation like this. A trainer colleague of mine suggests that you get specific (or real) by asking the questioner, “What specifically do you want to change?” Depending on where you are in the training, you may either refer to the question of “intent” or to the result you want to achieve.

Most of us want some behavior change to occur after having a crucial conversation—better punctuality, more participation in meetings, etc. We typically forget to clarify the expectations. Instead we ask, “How will we hold each other accountable for the change we’re committing to?” The failure to nail down who will do what by when and how we’ll follow up is often the culprit.

Another way to pursue this question is to do a “left-hand column check.” Was there residue that wasn’t dealt with in the moment that’s keeping you or the other person from feeling satisfied with the result? When the situation is persistent and has become a pattern, you might find that you’ve only peeled away one layer of the onion. So, long-standing problems might require more than one crucial conversation. The important thing is to stay focused on what we really want!

The ideas expressed in this article are based on the skills and principles taught in Crucial Conversations. Learn more about Crucial Conversations

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4 thoughts on “How many times should I have a conversation before I give up?

  1. Good suggestions about breaking down the eventual desired outcome into successive approximations, and about accountability. Also, I’d offer:

    1) Never give up.
    2) Adjust what it is that ‘you’ are expecting as change – it may not be the same as the person you are engaging, even if the conversation has been conducted in the “crucial” format.

  2. I’ve had this happen many times when I give a seminar. I turn the question into another question aimed at the questioner. For example; I said Why are we here? the answer comes back. I don’t know, I was told to be here. “Who told you, and what did they expect?”

    We keep going in this exchange until we get to the truth and understanding.

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