Here’s everything you need to know to launch a startup doing corporate education using management training software, from usable MVP to pilots at small-midsize businesses.

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Table of contents

1. ELI5: what’s newmanager.app
2. Pivoting: journey from company-operating-system to manager-training.
3. Product design: constraining decisions, inspirations, and demo usability session.
4. Process maps: formulas for product and sales development.
5. Architecture: technology stack and costs.
6. Future product considerations: beyond MVP with education and generative AI.
7. Avoidable mistakes: in teamwork, product, sales, and burnout.

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1. ELI5

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If you’re in charge of a department at a small-midsize business and get interrupted by low priority decisions, this software teaches junior managers to handle those low priorities.

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Newmanager.app is management training software. During a 1-on-1 meeting, a manager goes to a URL, picks a template relevant to their agenda, and follows instructions to ask questions out loud. The questions help them collect information and agree on a decision.

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After discussion they get notes and actions in a shareable format, and hands-on experience with decision-making for situations in the training catalog.

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2. Pivoting

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This product went through four pivots in the search to build something people want.

Company operating system

This project began as an intrapreneurial effort within an executive coaching firm; the first product design focused on coaches.

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Coaches used GoogleDocs for their meetings, and yearned for (a) modern interface, (b) action tracking, (c) templates for recurring agendas, (d) asynchronous pre-meeting preparation, (e) executive dashboards, and (f) workspace admin management.

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We built a prototype inspired by apps Hypercontext and Notion to get (a) and (b), onto which we started adding (c) - (f). Usability testing with coaches never demonstrated a superior meeting experience to GoogleDocs — in fact, the administrative functionality and design got in their way, disrupting the most important moments of client sessions (the build-up to reach an ‘aha moment’ of clarity / catharsis).

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After a few iterations, I felt uncertain about both the target user (executive coach) and product (Notion alternative).

Pre-meeting check-In

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So we pivoted from coaches to focus on managers.

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An unexpected use case resonated from asynchronous pre-meeting preparation (we had an intake form for updating outstanding priorities / actions from the previous 1-on-1 meeting).

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The form proved enjoyable to fill out live during a 1-on-1 meeting. However, I struggled to design an experience which proved useful for our usability tester.

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This functionality overall felt nice-to-have; a convenience during the manager’s 1-on-1 to get an update on outstanding actions. There was confidence in our target user (managers) and product design (forms), but the job-to-be-done (meeting preparation) still felt incorrect.

1-on-1 manager conversations

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Attention was shifted from senior-managers to first-time managers. The new product design hoped to get younger managers to mimic a senior manager in facilitating 1-on-1 conversations to completion with decisions. This project also exited the coaching firm to become a (solo founder) software startup.

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Features were removed which distracted from decision-making (eg. actions, goals, meeting agenda, admin management, etc). It was particularly important to remove actions; action tracking inherited massive scope which detracted from understanding the core 1-on-1 conversation experience.

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Form and rich-text-editor remained. A workflow was designed which updated the rich-text-editor document with simply-formatted-text after each step in the form. Gradually with every usability test, the form was tuned with simpler language (and additional steps) to make the template easier to implement correctly by anyone.

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The eye-opening moment happened when an undergraduate student — lacking any prior management experience — successfully guided their project partner to voice the root cause of anger, propose a solution, consider their comments, decide on the go-fwd, and agree to actions.

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The prototype finally felt correct. Additional form-templates were added to the catalog (off-track goal, and experiencing low motivation).

Manager training for decision-making

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While usability testing across the organization stack, directors were the only cohort showing enthusiasm for this product going live. Directors had a persistent frustration this tool (unintentionally) solved; they’re inundated with questions / requests / issues every week and wished their junior managers were confident enough to go handle, so they could focus on their department’s top priority.

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So I offered to use this tool in training their managers to handle those low priority escalations. Suddenly sales proceeded without objections nor resistance; two training-engagement pilots kicked off that week, and thus this software was positioned as management training.

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It was formally concluded that directors of small-midsize companies — who didn’t yet have a management training program, and promoted an individual-contributor into management within the last 90 days — were the target audience for this software. The value proposition became ‘minimum viable manager training’. [A]

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3. Product design

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The MVP for management training software had fewer features than initially scoped and a simpler layout - the majority of product redesign went towards consistency of the manager conversation experience (ie. ensuring anyone is able to do each step of the template correctly without deviation).

Decisions

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In retrospect, a few functionality decisions proved critical to iterating onto this MVP.

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(Mochary Method decision-making frameworks) Certain Mochary Method techniques were cherry-picked to seed the management-scenario template catalog. [B]

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(Omitting logins) Bypassing account creation removed all friction for test-driving the prototype; the parent URL simply triggered workflows to create a unique instance.

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(Auto-filling the notes doc) The form was designed to prompt one-at-a-time and gradually populate the companion document in a format friendly for sharing.

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(Deprioritizing action tracking) Actions were the bane of earlier iterations; eliminating them gave way for clarity into the core user experience around conversations and training.

UI / UX

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Existing apps / designs were leveraged for frontend inspiration.

The homepage provides a simple view for users to read previous discussions and start new ones. The design was inspired by Significa’s Hireproof project on Dribbble.

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When starting a new discussion, a modal presents the various templates available in the management scenario catalog. The design was inspired by Coda’s template picker.

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The discussion occurs in a new page; a form presents prompts one-at-a-time as instructions for the user to read aloud and capture answers, and the note gets transferred to the rich-text-editor document in a specific format. The design was also inspired by Significa’s Hireproof project on Dribbble.

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I eventually wanted to move the design into a modern collaborative document editing experience. Although this effort didn’t happen, Dropbox Paper was noted for future design refactoring, and used for minor layout aesthetics.

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Demo

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Cee Ng was kind enough to share her 1-on-1 session using this app, as a demonstration of the manager and direct-report experience (for a conversation around low motivation). This demo showcases every feature available in the MVP.

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4. Process maps

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These process maps outline the most productive usability testing and sales sessions used to iterate into the MVP and unpaid pilot.

Usability session

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Knowledge workers were the target for usability testing.

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Specifically, a usability session was deemed successful if a) the tester learned something new about a real issue they were experiencing in personal / work life and agreed to a decision which made them feel energized, and b) the template guided a facilitator fully through the conversation without them needing to deviate nor verbally fill in missing content.

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For the majority of usability testing, I took on the role of facilitator. Eventually, I transitioned to shadowing as others facilitated.

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Sales session

An SMB director was the target for sales. Specifically, a successful sales session concluded with an agreement for an unpaid management training engagement.

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It was interesting to learn that selling an unpaid pilot was not guaranteed. In sessions where the demo was unsuccessful — despite directors giving positive product feedback likely to avoid rudeness — there were sales objections to nominating a manager on their team for training (eg. “my team is too busy this quarter for training”, “you can send us the app link and we’ll take a look when we can”, etc).

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Sessions that didn’t convert into an unpaid pilot became another valuable resource for product development recalibration sessions. Conversely, sessions with a successful demo resulted in the director having a bias to kicking off this training (ie. responsive to emails, making warm introductions to their manager-nominee within a few days).

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5. Architecture

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Thanks to no-code tooling, engineering proved to be the easier work in this project.

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The web application consisted of a relatively simple CRUD app, and ancillary services were used to support the development / sales processes.

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The technology costs of running this business are ~$65 per month, and the breakdown:

• Bubble: $34.56
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• Carrd: $4.09
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• Calendly: $8.64
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• Zoom: $17.63
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The web app accumulated much tech debt over the product pivots, so it could be worthwhile to rebuild the app for the finalized use case of management training. The MVP can be outlined as follows.
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6. Future product considerations

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The current state of the app proved to be an appropriate MVP for real-world training of managers in small and midsize businesses. But the MVP is insufficient as an enterprise platform. Beyond shoring up standard functionality such as logins, future product direction is needed for a comprehensive product experience.

Learning Management System

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LMS market-leaders focus on the HR admin managing compliance for company handbook / policy / standard-operating-procedures. This feels like an opportunity; rethinking an LMS to focus on learning could involve…

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(Manager learning path) Today’s MVP has three decision-making templates in the catalog. A more robust learning path for first-time managers would need additional templates ie. feedback, conflict, firing, etc.

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(Peer-to-peer practice) I found first-time managers hesitant to implement these decision-making templates immediately into their 1-on-1s with direct reports. A solution could be to setup a peer-to-peer practice infrastructure, where trainees get coordinated into 1:1 video meetings and practice templates on each other until comfortable having those conversations with their team.

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(Additional learning paths) The training experience for a first-time manager can likely be repurposed for a first-time technology project team lead. Not only would this be a boon to SMBs who lack inhouse technical PMs, but for others it would alleviate senior leads from low-priority projects. If successful, there’s opportunity to identify more roles with training deficiencies.

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(Employee engagement) Successfully training managers and individual contributors creates a distribution channel for additional products. The peer-to-peer practice infrastructure could be repurposed to connect individual contributors feeling disconnected by remote / hybrid work. Using a similar coordination experience as popular Slack bots — with a template catalog curated for building trust / connection — it would connect teammates who don’t normally interact with each other.

Data infrastructure

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There’s rapid escalation in machine learning and Large Language Model technology. However, it’s not yet obvious to cram LLM functionality into this tool.

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The emergent generative AI use cases — chatbots (eg. Inflection) for question-and-answer, autocomplete (eg. GitHub Copilot) for productivity augmentation, and autonomous agents (eg. Adept) for repetitive actions — seem to fill a different niche than training a corporate skill.

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Until a clear LLM product design emerges for corporate education — and is validated on a junior employee in your team — it might make sense to focus on data engineering. A unique output of this management training platform is the corpus of quality corporate-middle-management conversational data.

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This data might prove interesting to companies like Atlassian / Accenture likely in the early stages of training their own LLMs. If true, then it could be worthwhile to build a top-shelf data repository as an attractive acquisition target for training-data advantage.

Moonshot

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What exactly happened in the early days within companies like Figma, responsible for superior communication, collaboration, and output?

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It could be interesting to design a teamwork accelerator. Its goal would be to rapidly move a group of first-time teammates through the Tuckman stages of group development (forming, storming, norming, performing) in parallel with their project’s kickoff.

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Imagine being able to improve the survival rate of 0→1 startup and intrapreneurship teams. With the exception of cofounders having shared work / friendship history, most new teams are formed of strangers. That’s a big addressable market.

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7. Avoidable mistakes

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Finally, what better way to cap off our time together than with the greatest hits of (avoidable) mistakes made during this particular 0→1 startup adventure? Despite past experience, wise peer council, and libraries of startup advice, there’s nothing like experiencing setbacks first-hand.

Being ignorant of Tuckman’s stages of group development

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This product kicked off as an internal company project by a new engineering team, so we predictably transitioned from forming to storming as opinions differed on how to accomplish the goal of building products for executive coaches and clients.

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I misunderstood the role of conflict / disagreement. Instead of seeing conflict as an opportunity to improve communication, I treated it as a bug; I used meetings to hotfix disagreements, and became puzzled as conflict intensified.

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Confusion turned to frustration, and eventually I opted out of teamwork hoping to avoid conflict altogether; I took on multiple areas of responsibility, neglecting teammates who had superior skills.

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My decisions contributed to blocking our transition beyond storming; we never got to experience this team perform as a cohesive unit delivering a common (clear and accepted) goal.

Quality assurance disguised as usability testing

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Early iterations of product development were frustratingly slow in their improvements. Many things were flawed in my process, but most notable were the usability testing sessions.

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Specifically, there wasn’t any usability testing. I was focused on catching bugs and confusion within UI / UX. Between sessions I would fix bugs — my priority became decreasing the number of defects. I was doing quality assurance; the product design never became less-wrong.

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The solution required a refactor of my product development cycle — using external user testers for unbiased feedback, designing the usability session to evaluate the product’s job-to-be-done, and recalibrating assumptions between sessions. [C]

Wrong wrapping paper for sales

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I vowed to quit on this project many times, especially during the sales development process.

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Despite starting to have consistently successful usability sessions, none of the users showed enthusiasm for the app. It was a classic Mom Test situation of a user persona who agrees with the value proposition in theory, yet their real behavior proves it’s not a hair-on-fire priority.

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Managers weren’t the right target for sales; neither were Individual Contributors, Cofounders, MBA students, nor HR executives. Managers and Individual Contributors theoretically wanted better 1-on-1s beyond project updates, but felt content with 1-on-1s being a bi-weekly checkbox. Cofounders theoretically wanted better communication, but top priority was revenue. MBA students theoretically wanted to become future managers, but were stressed finding warm introductions for job interviews. HR executives theoretically wanted an effective middle-management layer, but primarily wanted to solve their HRIS frustrations related to administrator functionality and integrations.

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The sales fit came with directors who lamented interruptions throughout their week by low priority decisions, and by positioning the app through the lens of a consulting engagement. [D]

Burnout as full-time solo founder

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Turns out one person can learn (and execute) the various areas of responsibility for building a 0→1 startup. But I failed to solve for the stamina required as a full-time solo founder.

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I resonate with Brené Brown discussing marriage — the work isn’t 50/50; the goal is to maintain 100% at any given time so when someone feels 20%, their partner steps up to contribute the 80% delta.

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My 0→1 journey proved to have relentless 20% days, even after things started working. These days had common traits of being in the wrong headspace so customer sessions were duds, pessimism seeded self doubt / futility, creativity was insufficient for product / sales recalibration iterations, and productivity was wasted enhancing inconsequential features.

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I thought I could make up the delta by moving to cities with a vibrant startup community, participating in online / IRL founder support groups, establishing an internship program, and onboarding pilot customers. These activities helped immensely, but we weren’t breathing the same air.

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“I learned then one of my first lessons of management – the best outcomes come from inspiring people to action, not telling them what to do.” - Julie Zhuo, The Making of a Manager

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Appendix

[A] Landing page for this startup: https://newmanager.app

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[B] Mochary method curriculum used for seeding the catalog: https://mocharymethod.com/learn  

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[C] 0→1 product development thoughts about how no one starts with the MVP, but instead iterates into it

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[D] 0→1 sales development thoughts about how the easiest way to do initial SaaS sales is by positioning yourself as a consultant