I've done some freelance stuff, and I'm currently doing a PhD where my time is very much my own to manage. Consequently, I've got some experience of being on the other end: being left free to my own devices, and occasionally having that backfire.

Things that I think are important:

* Give some small but significant (~week-level) milestones, ideally with tangible results. Then discuss these.

* Check up with the worker. Not by asking vague questions about how things are going, but specific questions about stuff that interests you in their work. I once worked on three projects at once for a place. Two of them were going very well, but one of them was going very slowly because I was kind of stuck. Getting input from the boss on that one really helped -- but I'd never have asked him about it, because I reasoned he'd hired me so he didn't have to worry about it.

* Help with any other stuff on their plate. Family issues, money issues, personal issues, etc. Obviously, you can't solve most stuff like this, but you can usually help. I once delivered a contract very late due to getting a wrist injury, and being unable to promptly see a doctor.

* Try to keep a dialogue going about work. Whether you're happy with their performance, whether they're happy with your pay/conditions, etc. Crucially, if any of the above ideas seem like overkill, you'll find out about this, and dial them down accordingly.

I have to deal with this too. Some people appreciate the freedom to come and go as they please and they will enjoy working. Others take advantage of the situation and don't accomplish their work. Dealing with the later can be frustrating if you are trying to create a comfortable, flexible workplace. If you warn somebody and they repeatedly can't get their work done, then you have to fire them, or risk losing your good employees. Good employees will justifiably grow resentful of always picking up the slack.

One idea that I use is - set your own hours. But then please adhere to your own schedule. If you want to start at noon, that's totally cool. But, actually start working reasonably close to noon. If your schedule changes, that's cool too. But let me know what that is and, again, adhere to your own schedule.

Getting uptight over being 5 minutes late is not really necessary in my opinion unless it's for an important client meeting or something.

What's backfiring?

There's two levels here: at the first level, you don't want to sweat anyone (capable or otherwise) about coming to work late because it indicates fundamentally messed up priorities: you aren't paying them to keep a seat warm. If you set them free to come in whenever they want, they will. If it gives you indigestion because you have no idea where your employees are, you need to figure out why that is and solve the real problem (and if the real problem is "my boss thinks I'm not doing my job if I'm not sweating my employees about seat-warming", my condolences, because you are totally fucked).

Don't confuse this with people who advocate self-management, where you just trust your people to do the right thing and set them loose without any structure at all. That's a much more subtle skill that requires the right relationships and the right situation and frankly is a gigantic hassle. If you've got a group of unmanageable geniuses who seem to be productive despite the chaos feel free to try but most teams who get things done do not operate this way and don't let the woo-woo peddlers tell you otherwise.

You're doing pretty well if the people who work for you feel like you have real, specific expectations of them but also have 'wiggle room' to do anything they want (just not everything they want).

Focus on results and not on some measure of what you think leads to results. If an employee is always 5 minutes late, but they always complete quality work on time, then why bother? Your time is better spent focusing on the employee that is always on time producing mediocre work.

When someone, especially a junior, is new to a project, make sure they get oriented to it. Don't just say "I'm always available if you have any questions." Because being able to take a codebase and a bunch of (even well-written, which it probably isn't) documentation and navigate it from the start without help is a skill that they don't really teach in school (at least not at MIT).

Without being oriented, they won't know what questions to ask and then after a week of slowly plodding through the code trying to piece things together, will be too embarrassed to ask.

You only need one metric: is the job getting done. Everything else is a distraction.

How do you measure that?

My team just took tons of heat because there was a complex performance issue that needed our full attention. We clearly communicated that we would need a large chunk of time to solve it, and while we tried to stay responsive, a lot of stuff had to just get ignored for a while to be able to make any progress on it.

We're finished now, and what we did will eventually save the client literally months of time over the long run, but because we weren't constantly placating the people who wanted to see the job "getting done," we put ourselves at risk of losing the contract.

All's well that ends well, I guess. We finished the task, and now we're back to churning through the high visibility low-effort issues and everyone's happy again, but all of those small issues combined don't have as much impact as the big task we just finished.

One strategy is to consider establishing a success metric as the first step to every project. If you can't design a measurement for success/failure, maybe you shouldn't be doing that project.

This is the one point that I keep re-iterating to the teams I work with. If you can't define what a success is move on and do something else where you can. It's very easy to get caught up in interesting stuff 'just because' but if it does not contribute in a measurable way then it's just another distraction that you should avoid.

Managing a client relationship is very different than managing employees. For managing clients I like over-communicating status while hiding my internal processes as much as possible to allow for a little bit of bullshiting when needed.

This is correct, from my understanding cultivated sternness happens not by being that way by default but by being so lenient at several different moments in your past that you were strictly taken advantage of until you could accept it no longer and you had to be strict or mean.

Then the first time you decide to do so all every one ever sees is "Oh this guy is really harsh, what a jerk".

Such is life. I'd LOVE for pointers on this.

I would imagine some flexible middle ground? Like a number of hours you strictly have to be in the office per week, but outside general availability time (10-14) they can choose when they come and leave as long as they fill their quota.

I meant the sterness vs niceness balance as a life thing.

Are you sure the working relationship with the people "this" has backfired with wouldn't be strained anyway, even without the loose rules?

I'm fully aware there are people who are "smart" but don't "get things done". However (though I am lacking any rigorous data to back this up) my suspicion is that people in this category who are prone towards taking advantage of employers are going to do so no matter what and being lax about strict attendance rules won't have a substantial impact on it.

IOW, just because they are (forced to be) present from 9am-5pm or whatever the defined working hours are doesn't mean they won't spend most of that time fucking off on reddit on their personal cellphone or whatever and they would have been problem employees whether or not the rules were loose -- if anything I suspect having loose rules makes it easier to identify when someone is not pulling their weight because there's a lot of ways to appear really busy to others while doing nothing when you're actually physically present.

And whats the end of the day metric to watch? Whether work is getting completed on time. If results are slipping or not up to the standards you are set, then there is a problem. If there is not, and communication is not suffering, then there is no problem, except the possibility that they may be bored or unmotivated and have the possibility of leaving.

There's a balance, and where that balance falls depends on how responsible and aware your team is. If you have a team that fully understands the business and product implications of what they're doing, then they can have a lot more free reign. If you have a team that just wants to write code and is allergic to thinking about anything that isn't code, you'll need to provide a lot more direction and guidance.

But there are very few scenarios where "you're five minutes late" is a sane thing for a manager to complain about. If you have someone with a consistent pattern of slacking off, that's one thing; if you have someone who is showing up five minutes late, but is otherwise a good employee, then just back off.

Or, at the very least approach them from a perspective of "is anything going on that I could help with?". As in, is there a way work could be more flexible to make things easier for them?

In what way does it backfire and can you specifically focus on that?