The Why Interview
Summary:
The "Why Interview" is your recipe for finding people who'll truly thrive at your organization. This focused early-stage conversation digs beyond skills and experience to uncover a candidate's true motivations and alignment with your mission. Instead of just checking boxes, this approach helps both you and the candidate determine if this is truly a YES before investing more time. Skills and experience matter - and the Why is non-negotiable.
What’s in it for you:
You want to build teams where people aren't just capable, but genuinely excited about the work
You want to reduce costly hiring mistakes and the painful exits that follow
You need a practical conversation-based approach that helps both you and candidates make better decisions
Helia’s Perspective
Every time I've hired for skills over the "why," it's been a mistake. I remember interviewing someone for a Chief of Staff role whose eyes lit up when talking about building systems. She wasn't right for the CoS position - but she became an incredible Operations leader who transformed our organization.
After hundreds of interviews, I'm convinced that understanding someone's "why" tells you almost everything about fit. The perfectly polished answer or incredible assignment matters - but ensuring underlying alignment from the beginning is crucial. When there's a mismatch, everyone spends too long trying to make it work, or it ends in a hasty, painful exit.
Before You Start
Make sure you are clear on the Right Role at the Right Level AND Identifying the Humans Who Will Thrive. You need to have a clear sense of who you're looking for to find the right Why!
Why Interview Guide
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Say: "I'd love for you to introduce yourself - you can either walk me through your resume OR tell me a few stories. What I really want to hear is what sparked you enough to say YES to this conversation about our organization and this role in particular."
Then shut up and listen. Seriously. Let them choose their path. It's fascinating!
Why this works: What folks choose to talk about - and how they do it - is wildly telling. I've had people talk about their dreams, complain about past roles, walk through their resume bullet by bullet, or introduce themselves like we're on a first date. Their approach reveals so much!
Notes on what to listen for:
What they lead with (tells you what they value)
Where their energy changes (that's the real stuff)
What they emphasize (what they're proud of)
What they skip over (sometimes even more telling)
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After they share (which I let go on as long as they'd like!), reflect back what you heard.
Say: "So it sounds like you really love building things from scratch, you get excited about mentoring others, and you're looking for a place where you can grow into leadership. Did I get that right?"
Why this works: This reflection moment does two crucial things: (1) Makes sure you didn't misread anything and (2) Gives them a chance to say "actually..." When candidates feel seen, it often opens up a whole other realm of honesty - "yes and here's why," "yes and also," "yes but what's really happening is…" This helps you get to the heart of their true motivation.
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Now describe the role - including some customization based on what you heard.
Why this works: This helps reveal their "why" beyond just matching skills to requirements. If someone mentions they love building things, share specific examples of what you have and what you need. If they talk about perfecting systems, describe your vision of a perfect system—and how close (or far!) you are from achieving it. This approach helps both you and the candidate see beyond checklists to transferable skills and authentic motivation.
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Invite their questions - and encourage FULL HONESTY.
Say: "For every hire I make, I want the candidate AND our organization to be screaming 'YES!' What do you need + want to know to help give you the clarity for that? I want any + every question you've got and will answer as honestly as possible so we're both making great choices here."
Why this works: The questions folks ask often reveal their priorities. Do they go deeper on examples you shared about the role? Do they focus on work-life balance? Do they care more about the work they're doing or the people they'll be working with? It's your responsibility to hear them and answer them so each candidate has what they need too!
Success Stories: It Really Works!
The Why Interview has told me everything I needed to know to make some unexpected but brilliant hires:
A Target store manager → Sales and Account Manager
Why? Her diligence, integrity, and understanding of how humans worked would translate into understanding customers, what they needed, and how to connect that with operational realities.
A national funder's External Affairs lead → National research and legislative work
Why? They loved fitting all the pieces together and understood the power dynamics.
A fashion industry project manager → Non-profit communications department
Why? They understood how to make diverse elements work together and brought a fresh visual perspective.
Red Flags to Watch For
Generic answers (dig deeper!)
Focusing only on what they're leaving (there needs to be a pull, not just a push)
When their story shows they want something different than what the role really offers
A lack of self-reflection and/or ownership
After the Interview: Self-Reflection
Ask yourself: Do I really understand their "why" - and is it aligned with our "why"?
Bonus: "Why" Questions to Weave Into Other Interview Rounds
While I recommend a dedicated Why Interview, these questions are beautiful to weave into any interview:
"Why our organization and why this role?"
Do you connect with our mission, growth stage, team, or working style? The "how" we do our work?
Is this role a stretch goal, a chance to build on past success, or something else entirely?
"What are you MOST excited about for your next role?"
This often reveals what people are really looking for. Once, a candidate gushed about mentoring others - something we hadn't discussed but that would be incredibly valuable.
"Thinking about every conversation you've had so far, why does this feel like the right role?"
This shows what they're picking up and what's exciting them - and has saved me when candidates are building a different vision than what we're hoping for.
Want to Try This?
Templates & Guides:
Be sure you're hiring for the right role! Right Role at the Right Level, Designing the Right Role Worksheet, and the Common Roles Reference Guide
Looking for sample questions that communicate your culture? Review THIS list of competencies alongside your organization's core values.
Recommended Reads:
To think through the type of people who will thrive in your culture: Identifying the Humans Who Will Thrive and the Finding Your People Worksheet
Have a person or org you recommend for interview help? Tell us about it!
Connections:
FitzRoy and Associates - if you want a recruiting partner that gives you incredible attention and helps you identify and find exactly who you’re looking for (versus a search firm who amplifies in their rolodex!), Caroline and her team are incredible partners. I’ve worked with them on and off for years and they build and adapt with you in ways that make all things better!.
Have a person or org you recommend for help with role scoping and organizational development? Tell us about them!
This is from Helia’s perspective! We've learned the most from doing and from talking with other doers willing to share their wisdom. We share these stories in the Helia Library because we don't need to start from blank pages or do it all alone.
As always, take what's helpful, leave what's not, and make it your own.
