Learning From Challenging Situations

Having coached many people over the past 15 years, I’ve witnessed my fair share of human struggle. I’ve had the honor of walking with many as they navigate their way through life’s challenges – the good, the bad and the ugly. As a result of these many experiences I’ve had with my clients, I have come to the conclusion that, while painful, confusing and downright frightening some of these challenges can be, they force us into consciousness of our strength and potential. They are the things that truly let us know who we are and what we are capable of. But how do we coach someone who is tormented by worry, heartbreak or total confusion into seeing it as a growth and learning opportunity? Here is a bit of a checklist to help coach someone from tormented to enlightened.


This means the coach has to be patient and have the ability to sit in the discomfort of it all with their coachee without pushing for solution and resolution. Just being with someone as a calm, still presence can be the most helpful thing you can do to help them move forward. Listening with just silence and nods can be a gift beyond measure when someone is in a state of confusion or fear. It’s important that the coach holds, within themselves, the belief that there is a way out, around, over or through all this and that the coachee will find their way to it when the time is right.

Acknowledge and Do Nothing

There is nothing worse than someone blowing sunshine in your face when you’re tormented with difficulty and in a state of fear or confusion. I’ve seen this mistake in coaching many times. Pushing for positive thinking without acknowledging the difficulty leaves the coachee feeling alienated and alone with their challenge. Saying things like, “This must be so difficult for you” or “I can’t imagine how scary this must be for you” let’s the coach know you SEE them in their challenge. In the same vein, pushing for the coachee to ‘do’ something by moving in to action planning too soon robs them of just sitting and ‘being’ with the struggle. It’s in that “being” state that the gifts of rich learning occur. Acknowledge the difficulty your coachee is having and encourage them to just ‘be’ in it and be present with them in that uncomfortable stillness.

Proceed Gently

When challenged, even the strongest personalities tend to be bruised and delicate. It may be masked behind anger or bravado, but delicate none-the-less. This is not the time to ask questions hoping for that big “aha” moment. Instead, ask them to guide you by asking questions like, “How can I best support you right now?” or, “What’s the best way I can coach you right now?” Let them know that you are completely there for them AND they are the ones in control of where the coaching will go. While proceeding gently, the coach needs to dial up their listening skills to hear if the coachee is ready for more. If you think you’re hearing them ready to move forward, ask them, “Are you ready to look at ways to move past this?” or “Are you saying you’re ready to make some decisions about this?”

Mining the Learning Nuggets

Often coaches will move on with their coaching once the crisis or challenge has passed. Solution found – coaching situation over. Without taking the time to help the coachee learn from their difficulty, the coach is merely coaching for solutions versus helping the coachee evolve. Most people are not able to learn from challenges until they are near or well into hindsight of a situation. Up until then, they are just trying to navigate their emotions and the situation and are dedicating a lot of energy towards resisting what is happening. When the coach begins to hear the coachee has moved past that resistance and into some sort of acceptance of the situation or the situation has resolved itself, that is the time to start asking questions like, “What has all this taught you?” or “What was the gift you’ll take away from all this?”. We partner with them until they find what they needed to know.

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