Water in a Deep Well

September 21st, 2020 | Latest News
Water in a Deep Well

Guest Post by Stan Oawster

A person's thoughts are like water in a deep well, but someone with insight can draw them out. Proverbs 20:5

I was recently working with a client who was really frustrated at their current situation.  Stress levels high and he felt that nothing was going right for him.  John (not his real name) is a senior leader in a manufacturing plant in the Midwest.  With an exhausted sigh he shares, “I have senior leadership that is changing directions every month, angry customers that are waiting on deliverables that are months late and a team of implementation consultants that are in survival mode and working in silos, independently toward what they believe is what’s best for themselves.”  He had that blank stare in his eyes, the one that just looks up and softly screams, “just tell me what to do, I have no idea and am feeling less confident by the minute.”

Be with me in that moment with John.  What’s coming up for you?  How do you respond?  Fifteen seconds of silence can feel like an eternity.  Maybe a leading question or suggestion that will steer him in the right direction and get him on a path forward.  “John, why don’t you just talk to your manager and team about the seriousness of the issue?  I’m sure they will all come together and work this out. Right?”  At least your intentions are good.  You want to help.

Question for us both, what’s the premise behind leading with questions? And how does it help John in a moment like he’s having?  What does John need most right now?

He needs to remember that he has what it takes and knows what to do.  It’s all in there and mine or your suggestion (at this point in the conversation) isn’t going to pull it out of him.  He needs a question that will stir him and wake him up to what is deep inside!  On an important side note, clients like John want to get value quickly and they want to go deep fast.  It’s important to get straight to the point fast.  I’m sure there are plenty of other questions you could ask but a sample of them could be…

  • What’s most important?  Pause and listen
  • What does your team need from you?   Pause and listen
  • What’s the perspective from the team?   Pause and listen
  • What does success look like?  Pause and listen
  • What are your greatest leverage points?  Pause and listen
  • What challenges are a high priority?  Pause and listen
  • How would you overcome that obstacle?  Pause and listen
  • What strengths can you and your team leverage?  Pause and listen

I emphasize pause and listen after each question only because human nature is to fill in the silence with words – our own words.  We need to be aware of what’s going on inside of us too at these moments.

When we lead with a question or two, we affirm John’s own insight and ability to think this one through.  We affirm that he’s the one in the situation and has perspective that we don’t have.  And that he does have what it takes to lead in moments like this.

Notice that leading with questions starts with the word leading, not only with questions.  There will come a time when the batting back and forth of ideas, suggestions, advice etc. will be appropriate. It always is at some point.  But those of us that have experienced the power of questions know that by leading with a question the conversation goes in the direction of the client and they come alive!  You are talking about what’s most important to them!  And slowly powerful insight come out from the bottom of their well and springs of refreshing waters sooth their worries and give them direction, strategy and new possibilities.  Hope springs eternal.

As the story ends, I did ask John a few of the questions from above and he did perk up and create a plan of action that was a satisfying start.  He eventually brought his team and manager…and a few other stakeholders such as his customers into the discussion.  And through his own experience of leading with questions with the group, they were able to define success and the strategy and commitments to get the work done, not just for the now but for the longer sustainable time.


  • What questions do you use to help the conversation go deep? 
  • How do you add value quickly?
  • What do others want from you?
  • What’s most important to you?  How do you want to add value?
  • Who would you invite into your well?
Stan Oawster


Stan Oawster is a Senior Organization Development Consultant for a Fortune 100 company. He is a certified ICF coach, Action Learning coach, StrengthsFinder facilitator and coach as well as a certified facilitator of the class Leading with Questions.  He’s an Elder at his home church Hope Community Church https://hopecc.com and enjoys mentoring married couples with his wife Carol of 31 years.  Stan lives in Minneapolis, MN and enjoys spending time with his family.


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