Our Sales Journey: The 5 questions District Leaders Keep Asking Us

Shweta Gandhi
5 min readFeb 5, 2024
I generated this image through DALLE - Prompt “5 questions district leaders are asking us blog post image retro-style” :)!

In our discovery conversations with district leaders, we’ve discovered a common theme: they are dealing with overwhelming workloads, tight capacities, and the constant fear of budget cuts. At Strived, we’ve decided to take it upon ourselves to provide some relief to these hardworking individuals.

And here’s what we’ve learned: district leaders are incredibly resourceful. They’ve developed systems and invested in solutions (with minimal budgets!) that work for them. While we aim to make their lives easier, we’ve found that they don’t necessarily want us to solve problems they can handle themselves. It often takes a push from higher-ups to convince them to consider something new, because the age-old saying holds true: “Why fix what’s not broken?”

Yet, our journey began by addressing a crucial question around this exactly:

1. What can you do to make my life easier (i.e., give me back time and optimize, optimize, optimize)?
This question led us to develop Strived, and we set out thinking, “Wow, we’ve nailed it!” We created a versatile tool with an open framework, capable of effortlessly assimilating your data. Strived comprehends the intricacies of the education landscape and provides accurate, real-world answers (well, most of the time!). It’s our way of giving district leaders back some precious time to tackle their other daily challenges without the manual labor of data analysis.

But as our journey has continued, we encountered a shift in the questions being asked, especially from leaders who were notably sophisticated and, well, let’s say, so entrenched in their ways that it’s evident they’ve invested a significant amount of time and energy. They posed a query I couldn’t shake:

2. How do you tell me something I, as a human being, would have a hard time figuring out myself? It seems so obvious a question, and yet it got our gears turning because, as we all know, this is precisely what AI was designed for. We had spent so much of our time at that point chasing the problem of ‘let me make your life more efficient — so tell me what you already know so I can automate it’, that it didn’t really occur to us to really go deeper until that moment.

AI has the superpower to decipher complex data in ways that go beyond human capacity. It’s like having a data wizard (i.e.: Strived for educators ;)!) on your side. So, this question has become our new north star. We’ve set our sights on a future where Strived not only digests vast volumes of data but also proactively makes sense of it and alerts you when action is needed, all before it’s too late! We’re excited to see how our upcoming customers can help us bring this vision to life.

But here’s the twist: there are customers who have their data meticulously organized and feel like they’re sitting pretty. These customers aren’t likely our earliest adopters, but they are our cheerleaders. However, they’ve had an “aha” moment — they’ve realized that the folks who should be diving into this treasure trove of data (i.e., the teachers) aren’t really doing so. That’s when they drop this question:

3. What can you tell me that my teachers will actually use?
In response, we, the mighty Strived-ers, declare, “Give us the specifics, and we’ll conjure up answers in plain English text — it’s like magic, and people will flock to it!” But, alas, this is a puzzle we’ve yet to fully crack. The granular data needed for classroom-level insights often exists in a non-digital form, making it challenging to harness. However, we’re optimistic that brighter minds than mine are working on solutions, possibly using innovative techniques like images and more to bridge this gap.

In addition to these core questions, there’s another thread that often emerges — a concern related to enrollment and absenteeism:

4. What can you do to help me with my absentee and enrollment issues — Because that affects my budget and, of course, my job!
Recently, our CTO had an interesting idea — sending automated texts to parents when a child is absent for just one day, encouraging Independent Remote Study. This addresses two critical issues: preserving per-pupil funding and supporting consistent student attendance for better academic outcomes. While this concept isn’t currently in our development pipeline, we greatly value the questions that spark innovation within our team as that’s what continues to push us to do more, and do it better!

Addressing budget concerns naturally leads to a question that might seem obvious, yet it’s possibly the most crucial one:

5. How do we make our teachers’ lives easier by telling them we are introducing yet another platform?
To be completely candid, I don’t have a definitive answer to this question. However, what I do know is that simplicity is paramount. If you can showcase the direct value to a user of a new platform through a seamless and intuitive user interface (UI/UX), you’re on the right track. The key here is to convey that value within the first 30 seconds because, let’s face it, teachers have incredibly limited time to spare. While we haven’t initiated our testing in this area yet, it’s because we want to ensure it’s perfected before we do.

In our interactions with district leaders, we’ve also come across recurring themes that extend beyond our current domain of expertise, spanning topics from mental health to the broader issue of teacher attrition and staff replacement (see point 5!). However, we’re mindful not to overreach and attempt to be everything for everyone. Our focus remains on addressing the questions and challenges that fall within our scope. Ultimately, if we can provide a solution that tackles even one of these questions with unwavering accuracy every time, we consider it a significant win in our ongoing mission to transform education.

Are there any burning questions on your mind, especially this time of year, that we haven’t delved into? Feel free to drop your thoughts in the comments below — we’re all ears!

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