The tools we’ve given instructional leaders were never built for instructional leadership.

A principal spends 4–6 hours writing a summative evaluation — not because the work is inherently complex, but because she’s synthesizing months of context into one narrative. She’s pulling from multiple observations, weaving in the teacher’s professional growth goals, aligning evidence to an instructional framework, and assessing performance against multiple dimensions of effective teaching.

All that, before she can give any thought to how to turn this evaluation into something useful for the teacher.

Now multiply that process by dozens of teachers in a building, and before you know it, the months of January and May have completely consumed the principal in documentation.

The documentation burden isn’t a side effect of this work. This is the system of instructional leadership we’ve designed.

This system crowds out the classroom time, coaching conversations, and strategic decisions that actually move teaching and learning outcomes. It keeps principals from collaborating more effectively with instructional coaches, department heads, and PD leaders who should all be working in concert to improve instruction.

Those other instructional leaders face their own documentation burden. Coaches need to log their activities with teachers. PD leaders need to capture attendance and feedback from professional learning sessions, ensuring teachers have the required training to meet school, district, and state requirements. The work becomes more about tracking than taking action to grow teachers.

Leaders are paying the full cost of this busywork without getting much of anything back in return.

Legacy software was built to lock in compliance

For the past two decades, most districts have adopted “all-in-one” HR platforms that give instructional leaders a place to, at least, house this information. But under the hood, these “platforms” are really four or five separate products, acquired over time and stitched together.

A principal’s observation notes live in one of those products. Coaching logs live in another. PD records sit somewhere else. There’s no shared picture of what’s happening because the architecture was never built to hold one.

KickUp was built as one platform from day one, with one data model, one permissions architecture, and one set of staff records. That underlying choice — to build instructional leadership tools from the ground up — makes it possible to turn the documentation burden into data that leaders can actually use.

Instructional Leader Intelligence removes the drudgery of instructional leadership

For the past year, we’ve worked with instructional leaders across dozens of districts on two related questions: where in their week do they lose the most time, and where do they walk into a moment without the context they need? We learned that those two questions converged on similar answers.

As former educators, we weren’t interested in bolting an AI chatbot onto a documentation tool and calling it a product. We wanted to know which specific moments in a leader’s day were broken, and then build for those moments.

Everything revolved around before, during, and after a visit into a teacher’s classroom.

Before.A principal walks into a classroom without the context she actually needs — what the teacher’s last three goals were, what pattern her assistant principal flagged two weeks ago, what the instructional coach worked with her on last Tuesday. She’s leading instruction with one hand tied behind her back, and so is everyone else who supports that teacher.

During.Unstructured notes get scratched into a notebook, Google Doc, or legacy software. She’s documenting the lesson while trying to make sense of it. For sports fans, it’s like trying to do the play-by-play and color commentary at the same time.

After.The form is a blank page at 9pm. Months of context — observations, coaching, PD — sits in separate places, none of it speaking to the others.

We set out to build a set of capabilities that dramatically change this experience for an instructional leader — whether you’re a principal conducting an observation, a coach working with a teacher, or a district leader trying to understand instructional practice across buildings.

Some of this is assisted by AI, and much of it with better, modern software that feels like it was built with instructional leaders in mind:

• Pre-meeting briefings that pull together past walks, coaching sessions, and goals before a leader walks in.
• Scripted notes that auto-tag to the district’s instructional framework as they’re typed, with timestamps.
• AI-drafted summaries that turn messy real-time notes into something a leader can review, edit, and use.
• Profile pages and dashboards that connect what the principal saw, what the coach worked on, and what the teacher attended in PD — into one picture instead of three disconnected ones.

In Lubbock ISD, principals across campuses who used these new tools cut their evaluation time by up to 80%. January and May stopped being lost months.

Assistant Principal Stacey Hensley described what a single formal observation used to take her: 45 minutes in the classroom, then six to eight more hours organizing evidence and writing feedback, often finishing late at night. After adopting AI scripting, the post-observation work that used to consume her evenings now takes a fraction of that time.

Other leaders described shifts in the quality of feedback they delivered.

One said she started seeing her observations through a wider lens than her own habits allowed. Another began questioning his own bias — the tool surfaced blind spots in his own observations. A third said the observations themselves got better, because she was capturing teacher and student moves in real time instead of trying to remember them later.

The feedback got sharper — not because AI wrote it for them, but because they weren’t exhausted by the time they got to the part that matters.

This is Instructional Leader Intelligence.

ILI is a commitment and a name for the direction KickUp has been headed. Some capabilities are AI-powered. Others are structural improvements to how information flows across the platform. What connects them is the question we keep asking: does this make an instructional leader more capable?

Instructional leaders are the engine of school improvement. They deserve software that understands their daily work, that doesn’t make them choose between compliance deadlines and being in classrooms, and that makes the time they invest in documentation actually worth something.

That’s what we’ve built. And this is just the beginning.