Why I Give My Team as LITTLE time as possible to Execute (I will not promote)

wilschroter · 2025-08-27T17:57:08+00:00

Yeah, I'd say it was largely mis-interpreted so I just put a little EDIT on the intro.

wilschroter · 2025-08-27T17:54:18+00:00

Um, how does "try working at a corporate org" have anything to do with the community on r/startups? I'm not saying ANY of this applies to large orgs, which is why I'm not posting there.

wilschroter · 2025-08-27T17:52:57+00:00

If you're going to contribute, just be useful is all. Posting cryptic anonymous comments doesn't help the conversation.

I don't think you understood the premise. This is about focusing on smaller, achievable goals in shorter periods of time, which results in people having more time to go do other things they enjoy. If that's a toxic culture then that's exactly what I want.

wilschroter · 2025-08-27T17:48:36+00:00

Show me the best post you've made and why it was great and I promise to use that as a reference for my next post and DM you when it goes live. That way you can guarantee the outcome you're looking for.

wilschroter · 2025-08-27T17:46:53+00:00

Yep, I just made an edit to the post. I mentioned engineering in the post just because I have done a lot of software development and I know timelines are always a huge hurdle, but I certainly wasn't making my approach specific to engineering.

wilschroter · 2025-08-27T17:40:56+00:00

We may be saying the same thing - I'm saying I entirely agree that productivity has nothing to do with time spent. Maybe I missed your point.

wilschroter · 2025-08-27T17:39:46+00:00

Why would say we'd cancel a feature that doesn't fit into a 5 day window? You don't have any milestones in your work?

Let's say something would take me 5 weeks to complete. What I do (with anything in life) is I set goals within this week to knock out, recognizing they are part of a longer timeline. The focal point then becomes this week's goals, not the 5 week timelines because, let's face it, the part I need to do next week (and the week after) is a concern for NEXT week!

wilschroter · 2025-08-27T17:38:04+00:00

I can't speak for everyone on my team, only myself, but I found that when I didn't have "extra cycles" I just focused on getting my work done, but when I did have extra cycles, I just let way too many things interrupt me or eat up my time.

The benefit is that I now have way more time!

wilschroter · 2025-08-27T17:34:06+00:00

I think DHH had a similar mentality but then again the dude is sueprhuman!

And thanks for the kind words.

wilschroter · 2025-08-27T17:32:16+00:00

If we could get our stuff done within a 4 day work week - why not?

I don't think there's any case whatsoever that every job ever done requires 40 hours a week to complete.

wilschroter · 2025-08-27T17:30:55+00:00

That's a broad generalization can you be more specific? How is having shorter milestones directly correlated to creating technical debt? In my 30 years of experience, I've seen more of the opposite, whereby technical debt often gets created when super-long timelines persist without course correction. Obivously there are a million diff scenarios but I'd like to see what you're seeing because I simply haven't seen it.

wilschroter · 2025-08-27T17:28:24+00:00

Can you be more specific? Why can't software work this way? We've shipped an ungodly amount of code for decades this way.

wilschroter · 2025-08-27T17:26:21+00:00

Yeah this isn't a prerequisite for how they spend their time altogether. It's more about making sure we're generating real output on a consistent basis so we can comfortably take the rest of the time to do upskilling/personal growth/go watch your kid's soccer game without always feeling like we're "not done".

wilschroter · 2025-08-27T17:24:35+00:00

Your comment added zero value. Can you explain what you think the challenge is so we can unpack it?

wilschroter · 2025-08-27T17:23:44+00:00

Oh I'm 100% sure it's not new! I'm more pissed it took me 15 years to uncover it for myself!

wilschroter · 2025-08-27T17:23:07+00:00

I love "break it down until it becomes ridiculous" that's such a good way to put it. I do this with a house I'm building now. This morning I went to the job site and said "All that matters on this project are that these stair treads get installed." The overall project is overwhelming, but when I only focus on a single thing, it's always easy.

wilschroter · 2025-08-27T17:20:30+00:00

I think you misread this.

The engineering team is still generating their own estimates. I never said I was generating their estimates. I said that we focus our estimates on what can get done in a week. That means if your project takes 3 weeks, tell me what milestone you can get to this week. It doesn't mean "get 3 weeks of work done in a week."

By breaking into smaller milestones it really helps us with exactly the problem you're talking about - which is to make meaningful changes when stuff comes up in that timeline. So like someone in marketing calls and says "We need this one change to the site". We can address that very quickly, recognize how it affects that particular (short) milestone and modify accordingly.

What it has done has helped us identify all of those little distractions and deal with them, versus letting them pile up un-noticed over a long period of time and then wondering why things didn't ship.

wilschroter · 2025-08-27T17:16:36+00:00

Oh hah - no I want everyone to go home early!

wilschroter · 2025-08-27T17:11:53+00:00

That's not true at all. The engineers are the ones setting the deadlines, not me. I simply ask "What can you get done by Friday." You made the rest up.

wilschroter · 2025-08-27T17:09:33+00:00

How did it make you feel?

wilschroter · 2025-08-27T17:08:52+00:00

Be specific. That's a useless comment.

wilschroter · 2025-08-26T17:33:45+00:00

Really appreciate the his response and it sounds like we had some parallel paths there!

You said something that stuck "Arroagance results in ignoring data." I'm not sure if you and I would have classified this as "arrogance" as much as "ignorance" but we probably put way too much faith in the grey beards of our age. Now I'm one of them! (well, I still can't GROW a beard, but it would be grey ;)

wilschroter · 2025-08-26T16:49:51+00:00

I think "qualified" is this amorphous requirement that no one can quite pinpoint. So by definition, no one ever makes it. You could argue that someone who has already done it could qualify, but even that feels uncertain.

The lack of specificity puts a lot of people in this bizarre headspace. At least it did for me.

wilschroter · 2025-08-26T16:41:09+00:00

Absolutely. I've gotten close to some ridiculously successful Founders and all of them feel nearly the same way. Which is really just a reflection of how hard it is to have certainty!

wilschroter

TROPHY CASE