Little Shift #3: Keep Asking… No, Really… Keep Asking
Asking “why” helps you Understand What Your Clients Really Need
Clients rarely reach out with the real problem.
They reach out with the thing that feels most obvious or easiest to name:
“My boss says I need a coach.”
“We need a team building.”
“Our managers need communication skills.”
These aren’t bad starting points—they’re simply the first answer.
And as coaches, consultants, and people-development professionals, our job isn’t to react to the initial ask.
Our job is to understand what’s underneath it.
This Little Shift is about slowing down, asking better questions, and using the 5 Whys to uncover the root cause behind the request in front of you.
The Power of the 5 Whys
The 5 Whys is one of the simplest (yet most underutilized) diagnostic tools in our field.
The premise is simple: each time a client shares a reason, you get curious and ask “Why?” again.
Not in a robotic, checklist way.
But with genuine partnership:
Why this?
Why now?
Why does that matter?
Why is this getting in the way?
Why is it important to solve this?
Each layer brings you closer to the real issue—the one that, if addressed, creates meaningful movement.
What This Looks Like in Real Conversations
A client says:
“We need coaching for one of our leaders.”
You ask:
Why do you feel coaching is needed right now?
“Well, their team is struggling to meet goals.”
Why do you think that’s happening?
“The team seems disengaged.”
Why are they disengaged?
“They’re not connecting with their new leader.”
Why is the connection missing?
“The leader jumped straight into tasks and skipped building trust.”
Why is trust-building so important right now?
“Because without it, the team won’t feel supported enough to hit their goals.”
You started with:
“We need a coach.”
You ended with:
“Our new leader needs support building trust so their team can perform.”
That’s a very different story.
And it leads to a very different solution.
Why “Why” Matters
When you respond to the surface-level need, you deliver a service.
When you uncover the root problem, you become a strategic partner.
This shift transforms your work in three big ways:
You create solutions that actually work.
You’re not just coaching. You’re solving a problem.
You differentiate yourself Before the “pitch.”
Curiosity becomes your value. Asking “why” helps you to gain insight and deliver a better solution for your client from the jump. In the end, your “pitch” should always matter less than the problem you are solving.
You help clients feel understood on a deeper level.
People buy when they feel seen. They stay when they feel supported. Building value beyond the initial ask helps you drive longevity in your client engagements and help until the problem is solved, not just until the training is over.
3 Ways to Start Using “Why”
Putting this into practice doesn’t require a new client, a new intake form, or a new product. Just a small shift in how you show up and stay curious. Here are three simple ways to start:
1. Add a “Why Now?” Question to Every Discovery Conversation
When a client shares what they think they need, follow it with:
“Why is this important right now?”
This single question opens the door to urgency, context, and deeper motivations that often go unspoken.
2. Use the 5 Whys to Redesign an Existing Engagement
Pick one current project—coaching, training, team development—and revisit the original request.
Start with asking yourself why:
Why did they come to me?
Why does this matter to their leader, team, or organization?
Why is this repeating or persisting?
Within minutes, you’ll uncover insights that can strengthen your approach, refine objectives, or elevate your next check-in conversation. Bring your insights to your clients and see how they resonate, or how you can refine your approach.
3. Make “Why” A Habit in Your Weekly Client Touchpoints
During a status call, debrief, or coaching session, listen for an assumption or challenge the client mentions in passing.
Then gently ask:
“Tell me more. Why do you think that is?”
This often reveals new dynamics, hidden barriers, or unspoken goals—and it positions you as a partner who sees beyond the obvious.
