Leadership Retreats Resources

Why We Need Coaching Leaders

4 Questions For The Coaching Leader

April 3, 2019
Leader's Journey
Jesse Parrish

I love backpacking trips. As a kid in Western North Carolina, I went all the time growing up.

My dad taught me how to plan and prepare for a hike. Prior to each trip, we always sat down with the trail map to discuss what lay ahead. We identified the best places to find shelter and water; we marked difficult stretches of trail; and we planned for upcoming weather.

My dad’s guidance taught me how to prepare for the terrain ahead. (His investment equips me to now guide my son in the same way.) One thing I’ve learned on my own, through years of going on trips, is that not everyone has the luxury of a guide to prepare them for the trail.

On youth trips as a kid, without fail, there was always at least one person who, despite their eagerness, had no experience and no idea what they were doing. I’ll call this “person”, Bill.

Bill would come with a backpack stuffed with three pairs of JNCO jeans, Converse tennis shoes, twelve cans of soda, Little Debbie snacks, Slim Jims for dinner, and no sleeping bag. By the end of the trip, Bill would be miserable – cold, hurting, dehydrated, disappointed, and unlikely to return to the trail again.

We All Know A Bill

At some point, we all encounter a Bill. Eager, but inexperienced and unprepared for what’s ahead.

Hiking success often hinges on having a leader who (like my dad) is willing to coach, support, and guide the development of the would-be hikers.

Lacking experience isn’t a bad thing. However, if all the Bills of the world had a guide, or a coaching leader, would they have a different experience? Could a guide’s direction result in Bill uncovering a desire to continue and grow in a new endeavor?

As a leader, it’s important to realize your opportunity to coach, and recognize opportunities to guide and support those you lead. Identify people who need coaching and start a conversation. Asking these four simple questions could make the difference between struggle and success for someone you lead.

4 Questions For The Coaching Leader


01. What does the Organization (or group) need?

Start by identifying the needs or goals of your organization, department or team.

Hiking example: The group goal was to hike twenty miles through moderate terrain over the course of three days. The need was for the group to execute the plan while maintaining positive attitudes.


02. What does the supervisee want?   

Seek to understand the hopes, goals, passions, and interests of those you lead.

Hiking example: If someone had stepped in as Bill’s guide, it may have become known that he wanted to learn camping basics; he may have had the desire to lead a trip of his own.


03. What do I (the leader) want?

Coaching moments are a great time to clarify any expectations you have for someone you’re leading.

Hiking Example: In order for expectations to be understood, the trip leaders could have advised Bill some homework to seek mentoring from more experienced backpackers; possibly sharing his packing list before the trip would have helped him learn more about what to expect.


04. What do I (the leader) see?

Once you’ve answered the first three questions, identify areas of alignment and overlap between the interests of all three stakeholders: the organization, the supervisee, and the leader.

It’s at this three-way intersection that you’ll discover opportunities to guide and accelerate growth for those you lead.

Asking these questions can also bring areas of misalignment to light that will give you the opportunity adjust expectations.

Hiking example: Had the leader recognized beforehand that Bill was uninformed and ill-prepared, steps could have been taken that would have benefited Bill and the entire hiking expedition.


Always Start With A Conversation

When the leader and supervisee have a clear and honest conversation based on these four questions, a foundation is set for a leader to direct, coach, support and delegate as needed. No emailed packing list would have adequately prepared Bill for a hiking trip; he needed an intentional, honest conversation.

Personal interaction is required to smooth the journey for all involved. Are you willing to take the time with those you lead for these honest conversations? Begin today so you can coach them effectively tomorrow.

For more on advancing your coaching skills, check out HBR’s guide to Coaching as a Leader or download our Story-Goal ebook.


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