GrantsMagic U

The Five Whys: Digging Deep to Rediscover Your Passion


The poor fellow just wasn’t getting it.

A volunteer with a rural fire department, he’d come to my two-day class, “The Grantsmanship Game: Playing to Win,” with a clear purpose in mind: To get funding for  his fire department to complete a national accreditation process. Now, I was using him as an example in a class exercise we call “The Five Whys” – and he was getting very, very frustrated.

Why is this important or valuable to the community?” I had asked. “Why does accreditation matter? – In other words, why should a funder support your proposal?”

“Because it’s important that we operate in accordance with national standards,” he responded, sounding like a corporate memo.

“And why is that important?”

“So we can achieve accreditation,” he said, an edge creeping into his voice.

I pressed on: “And why is that important?”

He looked at me as if I’d lost my mind. The rest of the class held its collective breath. “Because,” he said slowly, so even the densest among us could not help but understand. “We want . . . to operate . . . in accordance . . . with national standards.”


He was stuck – going around in circles. I’d seen it happen hundreds of times before, in my workshops, in consulting assignments. Very clear about the “what” – what we want to do or achieve or produce with our grantseeking – he had lost his connection to the “why.”

More accurately, he lived and breathed the “why” so passionately and at so elemental a level that it was inconceivable to him that others would not immediately see the intrinsic value of the cause. And that made it difficult – not impossible, but difficult – for him to articulate that intrinsic value himself.

Someone once said: “Passion without planning is chaos. And planning without passion is dead.” Never is the relationship between passion and planning more evident than in our work as grant professionals. We are very good, I tell my classes, at “to-do” lists. We’re action-oriented people, used to getting things done, and putting plans together is second nature to us. What’s not so easy is articulating the passion behind the plan – the “why,” in other words, behind the “what.” We load our issue statements (or problem statements or community needs assessments or whatever we choose to call them) with all kinds of demographics and statistical data and literature reviews – yet neglect to connect with the real story behind it all.

The “Five Whys” exercise is designed to do exactly that: Help us go deeper into our understanding of the issue we’re dealing with, to find the motivating “why” – and bring it out into the light of day. Think of it as an archeological expedition: Each time we ask “And why is that important?” we’re challenged to uncover another layer of need, issue or opportunity. What we’re looking for are the real human issues involved.

What’s at stake here? What’s the universal good at the heart of the matter? What greater cause are we in service to? In other words, what do we know to be true that motivated or inspired us to pursue this course of action in the first place?

Here’s how a simple “Five Whys” process might work. (By the way, in our classes, we have folks do this exercise in pairs, taking turns role-playing Plucky Grantseeker [Plucky], who is trying to drill down through the stolid resistance of a very Grumpy Grantmaker [Grumpy] – about whom more in a later article. The process just seems to work better when you’re talking to a brick wall.)

Plucky begins with a brief description of the “what”: “Good morning, Mr./Ms. Grumpy Grantmaker. Literacy Volunteers wants a grant to train 50 new volunteers to provide reading services to functionally illiterate adults.”

Grumpy (arms crossed, scowling): So what? Why is that important? (Why #1)

Plucky: Well . . . we currently have a waiting list of over 200 adults who want to learn to read, and we need to be able to serve them.

Grumpy: So what? Why is that important? (Why #2)

Plucky: (thinking: Gosh, I thought everyone knew how important it is to be able to read!) Well . . . A large share of these adults are parents with children under 18. 

Grumpy: So what? Why is that important? (Why #3)

Plucky: Well . . . Studies show that parents who can’t read are unable to support their children’s own success in school, placing them at high risk for educational failure.

Grumpy: So what? Why is that important? (Why #4)

Plucky (really getting warmed up now): Kids who fail in school are at higher risk of [fill in the blanks:] dropping out, unemployment, underemployment, welfare, criminal activity, gang involvement, etc., etc., etc.

Grumpy (pressing on, very brick wall-like): So what? Why is that important? (Why #5)

Plucky (momentarily speechless): Because . . . if we allow this to happen, we’re talking about the total breakdown of the very fabric of society as we know it today!

End of role-play.

The exercise is called “The Five Whys” because, if you’re really digging and not just going around in circles, by the fifth “why” you’ll have run into one of two dead ends: Either the total breakdown of society (as in our example), or the financial burden to the taxpaying public.

That’s the signal that you’ve drilled as far as you can, and it’s time to turn around and see which of the layers you’ve uncovered offers the clearest, most compelling statement of the motivating “why.” Rarely do class participants hit the motivating “why” on the very first question. Yet virtually 100% of the time, they do so within two or three layers. And when they find it – with their help of their Grumpy Grantmaker partners – it’s truly an “ah-ha!” experience – less a discovery, really, than a remembering of something they’d known all along, but lost sight of under the weight of all the “whats.”

Here are a few examples of the kinds of motivating “whys” that have surfaced in our workshops:

  • A wildlife rescue shelter wants a posthole digger to expand their enclosure for rescued bobcats. The motivating “why”: To provide a safer, more natural and comfortable environment in which these beautiful creatures can recover their health before being returned to the wild.
  • A senior center wants cell phone service for all their staff members, who are often away from the center running errands or taking care of clients. The motivating “why”: To assure that elderly citizens in need are able to connect quickly and easily with the people who have the resources to help them.
  • A historical society seeks to purchase and rehabilitate a 100-year-old schoolhouse slated for demolition. The motivating “why”: To preserve for future generations the opportunity to experience and learn from the rich history of our community.
  • An arts organization seeks funding to mount an exhibition of student sculpture. The motivating “why”: To provide a community showcase for emerging young talent in the creative arts.

In the end, it’s always about the “why” – the larger end we’re seeking to achieve with our actions, and which we’re inviting our funding partners to support. The “what” is simply a means to that larger end.

Back now to our volunteer firefighter, who, when we left him, was caught up in a never-ending loop of circular reasoning. Finally, taking mercy on him, I stepped back from the “Five Whys” and asked him: “Tell me, exactly what kinds of things do these national accreditation standards you’re talking about cover?”

“You know, safety things. Fire things,” he said. “Emergency response time. Disaster preparedness. You know.”

I put on a thoughtful face. “Ah. I see. Emergencies. Disasters. Tell me . . . would these be the kinds of things that might put someone’s personal property at risk? Their homes, maybe? Their businesses?”

He shrugged, still not getting it, and said: “Sure.”

“And what about personal safety? Emergencies . . . disasters . . . would these possibly pose a risk to people themselves? Their families? Might children’s lives be in danger?”

The light was starting to dawn. He nodded.

“So this accreditation thing . . . it’s not really about a bureaucratic process, is it? Isn’t it really about being able to assure the people whose lives, loved ones and property you have sworn to protect that you are ready and able to do so?”

He nodded, again. I leaned in close. You could have heard a pin drop in the classroom. “Then why,” I asked in a whisper, “don’t you say so?”

For the first time, he broke into a smile. “Oh, I get it. I get it now.”

And he did. The class cheered. Lesson learned. Passion rediscovered.


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  1. Patricia Bryte on March 14, 2019 at 11:08 am

    So so true! I learned this idea tons of years ago in promoting a pers dev weekend seminar. I wanted to communicate the seminar so passionately (saying to self, “I can NOT NOT tell everyone.”) that I learned to ask myself WHY? I learned in some network marketing workshop to ask self for the WHY behind the initial WHY. Yet here, you “dive deeply (as you would say) to go even deeper into the WHYs. Very WISE practice.
    Now Why am I reading this blog? 🙂

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  3. Shelton Szeredy on March 17, 2019 at 6:25 pm

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