That conversation taught me something critical: the questions you ask before starting a project matter more than the answers you provide during it.

If we'd just taken that website project at face value, we would have delivered exactly what they asked for—a redesigned website that wouldn't have solved any of their actual problems. They would have been disappointed. We would have been frustrated. And six months later, they'd be looking for another agency because the new website didn't magically fix their underlying issues.

The questions we ask in discovery aren't about gathering specifications. They're about determining whether a project should happen at all, and if it should, what it actually needs to accomplish.

Let me walk you through the specific questions that have saved us from bad projects and helped us do exceptional work on good ones.

Question 1: "What problem are you actually trying to solve?"

This seems obvious, but you'd be surprised how often potential clients can't answer it clearly.

They come with solutions: "We need a new website." "We need better social media." "We need a rebrand."

But when I ask what problem they're trying to solve, the answers get fuzzy:

• "Our website is outdated"

• "We're not getting enough engagement"

• "Our brand doesn't reflect who we are anymore"

These aren't problems—they're symptoms. And treating symptoms without diagnosing the underlying problem is how you end up with expensive projects that don't actually improve anything.

So I push deeper:

"What's not working about your current website? What are people trying to do that they can't? What opportunities are you missing because of it?"

"What does 'engagement' mean to you? What specific actions do you want people to take that they're not taking now?"

"Who are you trying to reach that your current brand isn't connecting with? What's the disconnect?"

Sometimes this reveals that the website isn't the problem at all. Maybe their real issue is that they don't have a clear value proposition. Or their programs aren't well-defined. Or they're trying to serve too many different audiences with one message.

I worked with an organization that came to us wanting a complete website redesign. After this line of questioning, we discovered their real problem was that they'd added seven new programs in three years without any strategic messaging to explain how they all fit together. Their website was cluttered because their organizational strategy was cluttered.

We could have built them a beautiful new website that would have been just as confusing as the old one. Instead, we helped them clarify their program structure and messaging first. Then we built a website that actually made sense.

Question 2: "What happens if this works perfectly?"

This is the question that saved us from that website project I mentioned at the beginning.

When organizations can't articulate what success looks like beyond "having the deliverable," it's a red flag. It means they haven't thought through outcomes, only outputs.

Good answers to this question sound like:

"If this works perfectly, we'll see more families actually completing our intake process instead of dropping off halfway through the forms."

"If this works perfectly, donors will understand exactly what their contributions accomplish instead of just reading vague impact statements."

"If this works perfectly, our volunteers will be able to find the resources they need without calling the office constantly."

These are outcome-focused answers. They connect the deliverable to actual organizational improvement.

Bad answers sound like:

"We'll have a modern-looking brand." "Our materials will look more professional." "We'll have content for social media."

These are deliverable-focused answers. They're not wrong, but they don't connect to any meaningful change in how the organization functions or serves its mission.

If a client can't articulate what success looks like beyond receiving the files, we're probably not the right partner. They need execution, not strategy.

Question 3: "Who needs to be aligned on this for it to succeed?"

This question uncovers potential approval nightmares before they start.

I learned this the hard way on an early project where we were working with an executive director who loved our strategy. But she hadn't gotten buy-in from her board. When we presented our work, three board members had completely different visions for the organization's direction. The project stalled for months while they argued internally about strategy that should have been resolved before hiring us.

Now I ask directly:

"Who has final approval on this?" "Who else has strong opinions about this decision?" "Have you already aligned on strategic direction, or is that something you're still figuring out?"

If there's significant internal disagreement about direction, I'm honest: "We can help you figure that out, but it needs to happen before we start building anything. Otherwise, we'll end up redesigning multiple times as different stakeholders weigh in."

Sometimes organizations aren't ready to hear that. They want to jump to execution and hope the deliverable will somehow force alignment. It never does. It just creates expensive revisions and frustrated relationships.

Question 4: "What's your timeline based on?"

Deadlines aren't arbitrary. They're based on either real constraints or imagined urgency. Understanding which one you're dealing with matters.

Real constraints sound like:

• "We're launching a new program in September and need materials ready for it"

• "Our annual gala is in March and we need updated donor materials"

• "Our old website platform is being discontinued in June"

These are legitimate external pressures. We can work with them.

Imagined urgency sounds like:

• "We'd just like to get it done"

• "We've been talking about this for a while"

• "It feels like it's time for a refresh"

There's nothing wrong with wanting to move forward. But when timeline pressure is self-imposed rather than externally driven, it creates opportunity to discuss whether rushing makes sense.

I had a client who wanted a complete rebrand in six weeks because "we've just been putting it off too long." When I asked what happens if we take ten weeks instead, they admitted: nothing. There was no actual deadline.

We took the extra time to do the strategy work properly. The result was significantly better than what we would have rushed through. And they were happier because the work was grounded in real strategic thinking rather than just "let's get something new out there."

Question 5: "What have you already tried?"

This question reveals patterns and prevents me from recommending solutions they've already tested and found ineffective.

Sometimes organizations have tried multiple approaches that didn't work. Understanding why helps me avoid suggesting the same failed strategies with slightly different packaging.

When I worked with a foundation struggling with donor engagement, I asked what they'd tried. Turned out they'd sent four different email campaigns, hosted two virtual events, and redesigned their donation page—all in the past year.

Nothing had worked. But rather than concluding "our donors don't want to engage," we dug into why those specific approaches had failed. The emails were too long and jargon-heavy. The virtual events had no clear call to action. The donation page was buried three clicks deep on their website.

The problem wasn't that their strategy was wrong—it was that the execution wasn't addressing the actual barriers to engagement.

If I hadn't asked what they'd tried, I might have recommended another email campaign. Instead, we focused on the underlying communication clarity issues that had undermined all their previous efforts.

Question 6: "What's your honest budget?"

I know this is uncomfortable. Organizations often want to hear our proposal before committing to a budget range. They're worried that if they name a number, we'll just price to that number.

But here's why I ask anyway: scope and budget need to be in conversation from the beginning, not at the end.

If an organization has $5,000 and wants a complete rebrand with new website, video content, and marketing materials, we have a math problem. I can either:

• Propose work that fits their budget (but won't accomplish their goals)

• Propose work that accomplishes their goals (but exceeds their budget)

• Help them prioritize what to do first with available resources

All of these are honest conversations. But they can only happen if we're both being real about financial constraints from the start.

I've had organizations tell me their budget is flexible, then balk when they see actual costs. I've had organizations lowball initially, then admit they have more resources once they trust we're not just maximizing our fee.

The specific number matters less than the honest conversation. If we can't talk openly about budget, we probably can't work together effectively.

Question 7: "What would make you regret hiring us?"

This is my favorite question because it surfaces unexpressed expectations before they become disappointments.

Answers I've heard:

"If you disappeared and stopped communicating mid-project" "If the work looked like everyone else's" "If you didn't push back when we're making a mistake" "If the final product was beautiful but didn't actually help us reach our goals" "If it took twice as long as you estimated"

These answers tell me what this specific client values and fears. They reveal past bad experiences. They clarify what "good partnership" means to them.

And sometimes they reveal expectations I can't meet. When a potential client said "I'd regret it if you couldn't turn around revisions within 24 hours because we need to move very fast," I knew we weren't a fit. That's not how I work, and trying to force it would have made us both miserable.

Better to know that upfront than to discover it three weeks into a project.

The Meta-Question: "Should this project happen at all?"

All of these questions are really in service of one bigger question: should this project happen at all?

Not "can we execute what they're asking for" but "will doing what they're asking for actually serve their mission?"

Sometimes the answer is no.

Sometimes organizations need internal strategy work before external marketing work. Sometimes they need to hire staff before hiring contractors. Sometimes they need to pause and reassess rather than push forward with execution.

I've talked potential clients out of projects because I could see they weren't ready. Not because I didn't want the work, but because taking their money to build something that wouldn't serve them well felt wrong.

Most of these organizations appreciated the honesty. Some came back six months later when they were actually ready. Some referred other organizations to us because they trusted our judgment.

The ones who didn't appreciate it probably weren't the right fit anyway.

What Good Answers Look Like

When I ask these questions and get clear, thoughtful answers, I know we're talking to the right kind of client:

They can articulate the problem they're solving They've thought through what success looks like They know who needs to align internally They have real (not imagined) timeline constraints
They've learned from past attempts They're honest about budget They know what they value in a partnership

These clients tend to be collaborative, strategic, and ultimately much more satisfied with the work because they understood what they needed from the beginning.

What This Process Prevents

This discovery question process has saved us from:

Scope creep - When everyone's aligned on outcomes from the start, "just one more thing" requests are easier to evaluate against the original goals

Approval nightmares - When stakeholders are identified and aligned upfront, we don't get surprise objections from board members in round three

Timeline disasters - When we understand real vs. imagined urgency, we can set realistic expectations instead of overpromising

Budget surprises - When we talk money honestly from day one, there are no awkward conversations at proposal stage

Disappointment - When we've defined success clearly, clients know whether we delivered or not

Why Some Organizations Hate This Process

I'll be honest: not every potential client loves this level of questioning.

Some organizations just want a vendor who'll execute what they ask for without challenging their assumptions. They find this process frustrating because they came with a solution in mind and I'm making them back up and articulate the problem.

That's okay. Those organizations should hire a different agency. There are plenty of excellent agencies that specialize in execution without strategic questioning. They serve a real need.

But that's not what Kern & Turn does. We're partners, not vendors. And partnership requires this kind of mutual understanding from the beginning.

How This Connects to Teaching

Teaching computer fundamentals at CIAT has made me better at this discovery process.

When a student comes to me saying "I can't get Excel to work," I've learned not to just troubleshoot their immediate technical issue. I ask what they're trying to accomplish. Often, Excel isn't the problem—they're using the wrong tool for their actual goal, or they don't understand the underlying concept they're trying to apply.

The same questioning framework applies. What are you actually trying to do? What have you tried? What would success look like? Who else is involved in this?

Students sometimes just want me to fix their immediate problem. But the better teaching happens when I help them understand the underlying issue so they can solve similar problems independently later.

Same with clients. They might want me to just redesign their website. But the better service happens when I help them understand their underlying communication challenges so they can make better strategic decisions beyond this one project.

Moving Forward: What This Means for You

If you're a potential client reading this, these questions give you insight into what working with Kern & Turn actually looks like.

We're not going to just take your initial request at face value and execute it. We're going to ask why, dig into outcomes, challenge assumptions, and make sure we're solving the right problem.

For some organizations, this sounds exhausting. For others, it sounds exactly like the partnership they've been looking for.

If you want a vendor who'll build what you ask for without questions, we're not the right fit. If you want a strategic partner who'll push you to think clearly about what you're trying to accomplish and why, let's talk.

The organizations we do our best work with appreciate that these questions exist to serve them—to make sure we're investing their resources in work that actually moves their mission forward.

Because at the end of the day, our goal isn't to deliver websites or brands or campaigns. Our goal is to help mission-driven organizations communicate more effectively about the meaningful work they're doing.

And that starts with asking the right questions before we build anything at all.