Bob Dylan and Frank Sinatra on Conversational Communication


I was sitting in the doctor’s office the other day and read an article about Bob Dylan. In his recent album he sings songs from the 20’s through the 40’s and refers to Frank Sinatra. Dylan shared what made Sinatra so great is that “he sang to you, not at you. He was able to get inside the song in a conversational way.”  I read that a week ago and it’s still on my mind. Like you, I am always looking for ways to improve my communication with clients, especially if you have been in your field a long time like I have. Bob Dylan has been an icon for a generation and yet he is still trying to learn how to “get inside the song and sing it in a conversational way.”

When was the last time you tried to communicate differently to your staff? Talk with them in a “conversational way,” understand them and listen more intently, speak with and to them rather than at them? When you have “told them ten times and they still don’t get it” it’s your responsibility as the leader and manager to improve how you speak with them so they do understand and are able to appreciate the message and “music” you are presenting.

Dylan and Sinatra are singing the same lyrics, how is it that one can come across so much better than the other? It’s a prime example of “it’s not what you say, but how you say it.” My suggestion for you is: For the next 3 days try a different form of communication and measure how the conversation changes. Listen more and ask questions, if you tend to take charge and speak a lot.  Conversely, if you tend to be quiet then I encourage you to step out of your comfort zone and share your ideas. Experiment with this and see what changes in you and how others relate to you. The joy of life is that we don’t have to stop learning, Dylan hasn’t. Have some fun and step out from your comfort zone and try making a different kind of music. Who knows, you may enjoy the song a lot more as well as the people you lead and manage.

Practical suggestion: I am sharing a method I have used for over fifteen years with outstanding success. It’s similar to a recipe, follow it precisely at first and you will get better results. Once you have successfully completed it a few times then adjust slightly to fit your personal style. First, choose two people you want to have an honest conversation with but have failed to out of fear or failed past attempts. Next, choose the easier of the two.

Collaborative Development Improvement Suggestions

9 basic steps.

  1. Make a list of 2-3 points for each of these questions:
    1. What is going well between us?
    2. What isn’t? e.g. where do we drop the ball?
    3. What is each person’s suggestions for improving it? If we were to try one of these suggestions, how would this improve our working relationship and the customer experience, performance, production creativity etc?
    4. If we were to mutually work on just one of these how might our performance and working relationship improve our department or company in the next 30 days?
  2. Go to that person and say “I’ve been reading about leadership and management development and I would like to try something with you, is that OK? It may put both of us out of our comfort zone and may sound crazy so I suggest we approach it like an “experiment.” Are you game? Ask them to make the same list and provide answers prior to the meeting. Schedule a one hour meeting for 2-4 days out (no sooner or later).
  3. When the person arrives into your office its best if both of you sit at the chairs in front of your desk. Do not have a table between you. Yes, one of you will likely make a joke about this being a therapy session. Just laugh it off and say I’m following the author’s recipe. Reiterate, “it’s just an experiment so it doesn’t really matter; let’s give it a shot.
  4. The leader goes first and reads his first statement from what is going well. Then the employee reads his/hers statement which closely mirrors the one the leader gave. If neither re close, choose the easiest. Using examples, discuss and debrief how the tow of you are able to achieve success in this particular area.
  5. Next go through the list of what is not going well. Obviously this is tougher and so you will need to reassure this person that this is an “experiment” so we both need to try new things which may be a bit uncomfortable.
  6. You go first. Read it your answer. Have them read the closest answer they have to it or choose the easiest topic between the two. Discuss and debrief. Does it relate to what is being done (a task or goal), or how it’s being done (the method, steps or stages) break these down. And discuss them. Don’t make any decisions, just discuss for creating awareness.
  7. Continue the process for each section.
  8. Collaborative communication is the main point to this experiment. e.g. How can I help you be successful and how can you help me be successful. This will start to refine and improve your teamwork and working relationship.
  9. Sticking points. If the topic conversation doesn’t go well, you probably don’t have a communication issue, you probably have a trust issue. The leader must encourage the subordinate to speak honestly to uncover how the distrust started. The leader must listen without judgement

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