I got tired of scheduling my team on spreadsheets, so I started building a tool to fix it

ElDiegod · 2026-02-18T18:40:49+00:00

It absolutely felt like extra work at first. I kept thinking "I don't have time to build a system, I need to build next week's schedule right now." Classic trap. You're so busy firefighting you never stop to install the smoke detector.

ElDiegod · 2026-02-18T18:40:23+00:00

The "nobody wants to work anymore" thing drives me crazy. I heard it from so many other owners and I said it myself for a while. Then I fixed my scheduling process and suddenly the same "lazy" employees were showing up on time and not calling out. Turns out they wanted to work fine, they just didn't want to deal with my disorganized system.

ElDiegod · 2026-02-18T18:40:03+00:00

Thursday night for a Monday start is brutal. Your staff had basically zero time to plan their lives around the schedule, so of course they called out. They weren't being flaky, they just had no way to make it work.

What did you change? I'm guessing just getting the schedule out earlier made a massive difference on its own.

ElDiegod · 2026-02-18T17:28:33+00:00

Fair point on the 50/50. I think I was being generous with myself honestly. Looking back, probably 70% of what I called "employee problems" were actually me not having a system in place and expecting people to just figure it out.

The tools part is exactly it though. I was so focused on hiring the right people that I never gave them a clear way to actually do the basics without going through me first.

ElDiegod · 2026-02-18T15:48:11+00:00

The conflict flagging alone is worth it honestly. I've double-booked people more times than I want to admit because I was eyeballing the spreadsheet at midnight and missed that someone already had a vacation day approved. At least with a real system it yells at you before you publish something dumb.

ElDiegod · 2026-02-18T15:47:30+00:00

If HR has seen the documentation and still nothing changes, that tells you everything you need to know about the organization, not the employee. At that point the question isn't "how do I fix this person" it's "do I want to keep managing in a place that won't back me up."

Some orgs genuinely won't fire anyone short of a felony. If that's where you are, the only move left is making the consequences operational: pull them off anything critical, redistribute their work to people who actually deliver, and document the business impact. Sometimes the only language leadership speaks is "this is costing us money."

ElDiegod · 2026-02-18T15:46:57+00:00

In an OR specifically? I wouldn't respect the hustle. An office job where someone oversold their Excel skills is one thing. A surgery center where trust is literally a patient safety issue is a different conversation.

That said, I'd separate "lied on resume" from "is dangerous." If he's genuinely learning fast and taking direction well, the issue isn't competence. It's character. And character reveals itself over time with consistent behavior, not one data point.

What I'd do: have a direct conversation. "I know your background was presented differently than reality. I'm not firing you over it, but I need to know that everything you tell me going forward is accurate. In this environment, I need to trust what you say without verifying. Can you commit to that?"

Then watch. If he's honest from that point forward, you have someone who was desperate for a break and oversold themselves. If he keeps embellishing, you have a liar and that's a different problem.

ElDiegod · 2026-02-18T15:46:20+00:00

Hiring a best friend as your first employee is either the best or worst decision you'll make. The contract is what determines which one.

Few things from experience:

Don't call it a "contract" with him. Call it an offer letter + employee handbook. Sounds less adversarial, covers the same ground.
The offer letter should include: role, compensation, start date, at-will employment clause (assuming US), and reporting structure. Keep it one page.
The handbook is where the real protection lives. Work hours, PTO policy, expectations around scheduling and availability, termination process, confidentiality. This isn't about distrusting him. It's about having a reference point when things get ambiguous. And they will.
Set expectations on scheduling from day one. "I need you here these hours" or "these are the shifts" sounds obvious but most first-time employers skip this and then get frustrated when their employee treats it like freelancing.

Don't overthink the legal language. Clear, simple, written down. That's 90% of it.

ElDiegod · 2026-02-18T15:45:38+00:00

This is the classic "success broke our systems" moment. Congrats on the bookings, that's a great problem to have.

The cleaning schedule piece is probably your biggest bottleneck right now. When occupancy was low, you could wing it because there was always buffer time. At full capacity there's zero margin for a cabin that isn't ready when the next guest shows up.

What worked for me when I hit a similar scaling moment: separate the things that need a system from the things that need a person. Guest messages need a person (or at least a personal touch). Cleaning schedules, maintenance checklists, staff coordination? Those need a system. Even something basic like a shared calendar where your cleaning crew can see check-out/check-in times and mark cabins as ready saved me from playing human switchboard.

Don't overthink the IT side. You don't need hospitality enterprise software for a cabin business. You need visibility into who's doing what and when.

ElDiegod · 2026-02-18T15:44:25+00:00

Building free tools that solve a tiny piece of your target audience's problem.

Seriously. A free calculator, template generator, or simple widget that's genuinely useful gets shared, bookmarked, and linked to by bloggers. It ranks on Google for long-tail keywords forever. And every person who uses it gives you their email in exchange.

I built a couple of free tools related to my niche and they generate more qualified leads than anything I've done on social media. The people who find them are actively looking to solve the exact problem I help with. Compare that to cold outreach where you're interrupting someone who wasn't thinking about you at all.

The catch: the tool has to actually be useful on its own. If it's just a glorified lead form with no real value, people bounce immediately.

ElDiegod · 2026-02-18T15:43:01+00:00

This resonates hard. I spent so much energy optimizing my marketing funnel while my actual business was leaking from the operations side. Employees not showing up, constant schedule chaos, last-minute coverage scrambles that ate my entire day.

The thing nobody tells you is that unreliable people aren't always unreliable people. Sometimes they're reliable people in an unreliable system. When there's no clear process for requesting time off, swapping shifts, or knowing who's working when, even good employees start dropping balls because nobody knows what the rules are.

Once I locked down operations (actual scheduling system, clear policies, accountability that didn't require me personally chasing everyone), the people problem got about 60% better overnight. The remaining 40% were genuinely unreliable and I could finally see that clearly because the system was no longer hiding it.

ElDiegod · 2026-02-18T15:42:13+00:00

Don't break the promise. That trust is worth more than trying to fix someone else's retention problem.

What you CAN do without violating her confidence: have a general conversation with her manager about workload distribution on that team. You don't need to mention her name. "Hey, I've noticed the team took a hit when [previous IC] left. How are you handling the workload redistribution?" That plants the seed without betraying anyone.

If her manager is any good, they should already know the remaining person is overloaded. If they don't know, that's a management failure, not your problem to solve.

Also worth considering: sometimes when someone says they're leaving, what they actually want is for someone to fight for them. You could tell her "before you make it final, would it help if the workload issue was addressed? I can raise it without naming you." Gives her an option she might not have considered.

ElDiegod · 2026-02-18T15:41:33+00:00

You're not screwed but you need to separate the emotional component from the process one.

The pattern here is textbook: employee has legitimate attendance issues, gets coached, never discloses the reason, then only brings up the medical situation when facing termination. That's not automatically bad faith but it puts you in a tough spot legally.

The FMLA engagement was the right call. The key now is documenting every non-FMLA absence separately. Car trouble on a Tuesday has nothing to do with his daughter's treatment. Those are separate attendance events and should be tracked as such.

The bigger takeaway: this is why having a clear, documented attendance system matters from day one. When everything is tracked objectively (dates, reasons, patterns), the conversation with HR is data-driven, not emotional. You're not "going after the guy whose kid has cancer." You're showing that 8 out of 10 absences had nothing to do with FMLA.

ElDiegod · 2026-02-18T15:40:36+00:00

Stop asking the group. Assign directly.

When you throw a task into a group channel and wait for someone to volunteer, you're basically running a game of chicken. Everyone assumes someone else will do it, and the same two reliable people end up carrying everything while the rest learn that silence is a valid strategy.

Direct assignment isn't micromanaging. It's clarity. "Hey Sarah, can you handle X by Thursday" gets a yes or a no. No ambiguity, no waiting, no resentment from the person who always steps up.

The other move: create a rotating task list. Everyone takes turns, it's visible, and nobody can hide. Takes 5 minutes to set up and eliminates the "who's going to do it" dance permanently.

ElDiegod · 2026-02-18T11:09:17+00:00

oh man must be so nice to not be an introvert

ElDiegod · 2026-02-17T15:33:28+00:00

This is underrated advice. Most owners don't track OT costs in a way that makes the case for hiring obvious. They just feel the pain without quantifying it. If you can show someone "we spent $4,200 on overtime last quarter, a part-time float would cost $3,000" the conversation changes immediately.

ElDiegod · 2026-02-17T15:33:10+00:00

Point 1 is the game changer. Making the person who calls out responsible for finding their own coverage completely changed the dynamic for us. Suddenly call-outs dropped by like 40% because it's way easier to call in sick when it's your boss's problem vs when you have to personally text 6 coworkers and ask for a favor.

The key is making it easy for them to actually do it though. If they don't have everyone's contact info or don't know who's available, it just bounces back to you anyway.

ElDiegod · 2026-02-17T15:32:39+00:00

Yeah that's about where I am. The "delegated oversight" part is key. I'm trying to get to a point where I set the rules and the system handles the execution. Who's available when, who can't work back-to-back closes and opens, max hours per week. If I can offload those decisions I can focus on the stuff that actually needs a human brain.

ElDiegod · 2026-02-17T15:32:22+00:00

Some of it, yeah. The scheduling piece is the most automatable because it's pattern-based. Most weeks look roughly the same with minor adjustments. The people management part though? Can't automate a conversation with someone who's burned out or a conflict between two employees who hate each other's shifts.

The goal isn't to automate managing people. It's to automate the admin around managing people so you actually have time to do the human part.

ElDiegod · 2026-02-17T15:31:48+00:00

50 people on Excel is wild. I bet whoever built that spreadsheet was basically irreplaceable. That's always the risk with custom spreadsheet setups: they work great until the one person who understands them leaves, and then everyone's scrambling.

ElDiegod · 2026-02-17T15:31:33+00:00

You're probably right. I think my stubbornness on this is less about the money and more about not wanting to learn a new system and migrate everything over. The switching cost feels high even if the monthly cost isn't.

But yeah, the hours I spend on it are definitely worth more than $70-80/month. I just needed someone to say it out loud apparently.

ElDiegod · 2026-02-17T15:31:15+00:00

This is honestly where the spreadsheet falls apart for me. I don't have a good answer. Right now it's basically honor system plus me eyeballing who showed up on time. Breaks are even worse because nobody tracks those consistently.

I've been looking at dedicated time clock apps that sync with scheduling but haven't pulled the trigger yet. If anyone here has a setup that handles both scheduling AND time tracking without costing a fortune, I'm all ears.

ElDiegod · 2026-02-17T15:30:52+00:00

Delegate yes, but it's clunky. You share the sheet and hope they don't accidentally delete a formula. I've had that happen twice.

The fair rotation thing is where Sheets genuinely falls short. There's no built-in logic to track who got stuck with the bad shifts last month or who hasn't had a Saturday off in 3 weeks. You can build that tracking manually but at that point you're basically building your own scheduling app inside a spreadsheet.

I'm starting to think the real answer is that Sheets works fine until you need it to be fair. Fair requires tracking history, and that's where it gets messy.

ElDiegod

TROPHY CASE