The Problem with Shallow Conversations

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Have you ever dedicated time to thinking about what your family needs? Or your friends? Your employees, colleagues, or others who depend on you? You are probably thinking “of course I have.” For sure you have, but is your understanding accurate? Deep enough? Do you really know their true needs? Not what they want, but what they need to be their best selves? If you are a manager, do you really know what your employees need to give their best? Or how you can best set up your children, spouse, closest friends, neighbors, or parents for success?

Here is a test: list the top five people in your life and make note of what they need.

What did you come up with? Do most people whom you care about need to work harder? Or have more money? A better job? To lose weight? Maybe, but if you truly know a person, you probably came up with a different list. You probably came up with deeper and less tangible needs like motivation, meaning, accountability, or exhortation. Or they need courage, relationship, security, certainty, respect, independence, hope, or peace. Or non-financial resources like assistance, knowledge, experience, time, or better methods.

Here is another test. Think about yourself for a minute. What do you need? What do you really need to be your best self? Or the most joyful you can be? Take a few minutes and make note of what you really need. 

What did you come up with? Does your list of needs include intangible attributes? Are they non-monetary or non-physical? Are they mindsets rather than results? If so, your list is probably a lot like most others’.

We live and work with people. We spend a great deal of time with others, build relationships with them, and help them in many different ways. But do we know and help them where they have the most need, particularly those who depend on us? Do we know what they are thinking and feeling? For many people the answer is “no”. For example, we all have fears. Do you know the fears of those in your circle of influence? Do you know who desperately needs meaning in their life? Or who has an inner void in terms of feeling valued and respected?

Some people just need certainty or less chaos. They are tired of not knowing how circumstances are going to turn out. Some just need peace and rest. Some need independence from a controlling circumstance, addiction, or person. In the workplace, many need more feedback, mentoring, coaching, training, or new experiences. Or better tools, equipment, processes, or systems.

If we truly care about someone and want to help them, we should probably know what they really need to be their best self, right? Not just what they desire externally, like money, time off, or a promotion. Yes, they may need less stress, a better job, or a change in circumstances, but they also have less tangible needs that if fulfilled might give them more sustained and beneficial help. If so, we should get beyond knowing them at a superficial level. We should get beyond surface needs.

If you want to truly set up your family, employees, and others who depend on you for success, move beyond shallow conversations.

Here are seven practices to follow in uncovering deeper and more specific needs that if fulfilled might help those you influence in ways not experienced before:

  1. Assess your frame of mind and approach. Adopt a mindset that values knowing people at a deeper level. Make the decision to talk to people about topics that maybe you’ve been shying away from. See the value in moving beyond superficial conversations. Decide to move past talking about what people are “doing” and talk about what people are “thinking and feeling.” Embrace the mindset that moves from asking “what are you working on?” to “how do you feel about what you are working on?”
  2. Set aside quality one-on-one time with those you care about. Foster a climate of authenticity. Let them know that you genuinely value them and want to help them. Ask for permission to build deeper relationships with the intent to know them better and if appropriate, help them. Confirm they feel safe in being authentic and vulnerable. Admit that you might not be able to help them, but that you would like the opportunity to try.
  3. Ask meaningful questions that lead to deeper dialogs. Here are a list of questions you might try: “How are you doing?”, “Are you enjoying your work, school, or life?” “Are you happy?”, “What is preventing you from being happy and enjoying life to the fullest?”, “What is preventing you from reaching your goals?”, “If you had three wishes right now, what would they be?”, “What might help you be your best?”, “What are the biggest issues you face right now?”, “What are your biggest fears, concerns, and uncertainties?”
  4. Make note of what people need. Take a break from the conversation to give it thought. When ready to continue, discuss their needs further and confirm you have it right. Validate the need by talking about the impact of satisfying their need. If there is remaining doubt, ask more questions. Ask something like, “If you have this need satisfied, then you will be happy, right?” or “How confident are you that addressing that need will enable your success?” For many people, knowing their true need is half the battle. They receive immediate relief. They feel progress. They start pursuing solutions.
  5. Once you have agreement on what people need to be successful, be happy, or achieve whatever they aspire to achieve, agree to look for opportunities to help. Ask them to do something as well that helps them fulfill the need. If for example you have an employee who doesn’t feel valued and therefore is disengaged, ask something like, “While I strive to be more affirming of what you do well, will you strive to be more engaged and maintain a can-do attitude?” Or ask “While I try to secure more resources for you, will you research this topic and identify 2-3 alternative approaches you might take?” Agree to talk again as soon as reasonable.
  6. Between your discussions, look for opportunities to help them. Research their needs and identify any books, methods, or other resources that might be helpful. Consider your capabilities and provide whatever assistance, empathy, encouragement, affirmation, or whatever is reasonable. If applicable, consider your role in creating their need. Is there a change you need to make to reduce the severity of their need?
  7. Follow up. Stay connected. Review and discuss their progress. Help them stay accountable. Ask questions like “What have you done in the area we discussed and how is it going?” or “Have you experienced any successes or encountered any obstacles?” Help them assess what has worked and what hasn’t worked. Give reinforcing feedback for what is working. Help them think through whatever might not be working. Agree to keep talking as long as they make steps forward.

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Article by Mike Hawkins, award-winning author of Activating Your Ambition: A Guide to Coaching the Best Out of Yourself and Others (, author of the SCOPE of Leadership six-book series on coaching leaders to lead as coaches (, and president of Alpine Link Corp (, a boutique consulting firm specializing in leadership development and sales performance improvement. For other articles on reaching your peak potential, visit:

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