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Its going to be damn awkward managing someone significantly older than myself.

Only if you make it so. There is no reason why it has to be that way. I have often had this "problem" - unfortunately as I am getting older, less and less :-) It has never been an issue for me.

Bear in mind, managing is hard. Managing well is harder - many people never get it right. Good management is not based on exploiting the power imbalance between manager and employee. So an age differential (socially a power imbalance issue) should not matter.

As to your specific question: a software developer is generally an exempt employee. She or he are not paid by the hour, they are paid to do the job done. However, depending on how much you are paying them, you need to make sure that "getting the job done" can be done in 40-hour-type working week.

In terms of office hours, I believe that sheer contact hours are very important in the beginning between co-developers, so that they can have a chance to get in each other's head. After that, you should do whatever works well for you. If you work round the clock, identify a slice of the day where you want to interact with this person that fits with his or hers natural rhythms (ask them!), and call those "core hours" where you expect this person to be physically present. Trust them to develop their own schedule around that, and again, focus on monitoring outcomes, not hours.

The most important thing about team schedules is predictability. I would rather have someone who was in the office 6am-noon every day, rather than somebody who was at the office for longer but with an unpredictable schedule.

I really have to point you to this blog - askamanager.org - go read the backlog. It is full of some terribly sane advice about managing people. It's not about a technical setting, but people are people. Here's a good start:

http://www.askamanager.org/2010/06/deathbed-advice-for-manag...

You know what a difference there is between a good developer and a poor developer. The same difference is there between a good manager and a bad manager. If you work at being a good one, you will be.

In your questions, I see some conceptual confusion between managing individuals and supervising them.

Good management is about facilitation and planning -- proactively getting people what they need to complete tasks without sacrificing the long term. Managing individuals is not inherently hierarchal and occurs not only down, but Up the organizational chart as well. Importantly, management relationships can be reciprocal and cooperative. In my experience most people have an intuitive sense of good management because it can be practiced as a subordinate; of course study, training and experience are needed to build upon that intuition.

Supervising people is about enforcing requirements. Unlike management, supervision is solely based on a formal hierarchical relationship and a disparity of power. Supervision always requires expression of the formal difference in power and the supervisory relationship is non-reciprocal. Unlike management, I believe our natural instincts toward supervision are crap; because new supervisors by definition lack experience with the power, they tend to use a heavy hand, and this is the danger you face.

As a manager expectations regarding schedule should be discussed as part of the interview process. Particularly in your situation when the signals regarding corporate culture are so mixed. You're working 19 hours, the employee is expected 9-5 only, and yet there's pair programming. The age of the employee has nothing to do with it.

As a supervisor, the place to start is treating your subordinate as if they had just handed you their two week's notice and you need to maximize their productivity before they leave – because that situation is always only one day away.

The moment you think, "If the employee doesn't do 'X,' I will fire them," it is a warning sign and should first trigger a deep reevaluation of your conduct, expectations and requirements within the context of the reciprocal/managerial relationship with your employee and the long term goals of the organization. The age of the employee has nothing to do with it.

If after that reevaluation of yourself, you still think "If the employee doesn't do 'X,' I will fire them," then it's time to fire them regardless of their course of action because the management relationship has failed. The age of the employee has nothing to do with that either.

Good luck.

You should expect him to work 8 hours day and depending on the culture you wish for your company, I also suggest you be laid-back with office hours. The most important is that things get done regardless of when. Losing good employees is very costly, you want to maximize your chances they are happy. Having strict rules and implying that employees are more or less "required" to work more than 40 hours (because everybody else do) will eventually burn them out and they will leave. Great developers have a lot of opportunities!

I've been involved with a number of startups, and I can't think of a single occasion when early employees worked less than 10 hours a day. I think setting a lower expectation is wrong for at least three reasons:

1) It is entirely possible to work 50 hours a week and have a good work/life balance without burning yourself out (I say this as an actively involved father who works more than that).

2) The first few employees are absolutely critical to how the company and culture will evolve, and if you want to build a high-performance team, you really need employees who are driven to work harder than they would an established company. Setting clear expectations about work hours is a good way to screen out those who aren't ready for the challenge.

3) The very first employee is practically a founder and needs to think and act like one. Which isn't to say they need to work as much as you do, but certainly a good bit more than a 40 hour week.

Seconded!

If you're working 19 hours a day, there aren't many hours when you're not working.

As such, there's no reason to put too many limits on when your 1st employee can work (so long as those 40 hours/week are met and stuff is getting done).

You may wish to consider allowing telecommuting, as well as to allow employees to save every hour over 40 they work per week as vacation time ("comp-time"?).

Another alternative: as the employee what type of schedule s/he would like to set, and make it a cooperative process rather than an autocratic process. Autonomy is a huge component of job satisfaction (along with complexity and a clear payoff between effort and reward), so the more autonomy you can give, the more likely it is that you'll keep this person happy enough to stay.

The last full-time job I worked, I was the only full-time employee, and was not allowed to set my own schedule, nor to choose my own tasks, and I was frequently required to work 10-20 hours per week of unpaid overtime. Needless to say, my happiness levels jumped significantly when I quit that job, in spite of the tenuous nature of substitute teaching and non-profit work.

Hopefully your first employee will have a much better experience.

Speaking as a relatively early (#5 or so) employee in a startup, I second this. I work 40 hours a week remotely, but if I'm on a roll or I head to the office, it's not uncommon for me to put in overtime. I worry a bit that I'm underperforming because some of the other guys put in the kind of time the OP describes, but I don't think it's ever been expected of me, as long as we're getting stuff done and hitting our targets. The founders at my place may be unusually cool, however, so YMMV.

Make sure s/he's on-board with the objectives, make him/her part of the estimation process, agree targets (features, fixes, etc) with timescales, point him/her in the right direction and let go. Hand over the responsibility.

Occasionally when passing ask how it's going, whether it's ahead or behind. Check roughly every day or so, asking if there's anything needed to unblock progress, or if it's going well.

As you work on the agreed timescales/workload, hours will settle out naturally. Let them work whenever they like to achieve the goals, but make sure they're in fairly frequently so you have the communication.

All this can be mutated, but that's what works for me.

My advice is to just have reasonable deadlines and milestones, and let him work as often as it takes to hit those goals. If that means crunch-time occasionally, so be it.

I just started at a very young company. There was already a clear expectation that I work 40-50 hours per week (since it is written on the contract).

On the first day, one of the founders asked me: "what are your hours going to be? I come in at 10, Bob comes at 7, and Frank at 9:00.".

I liked this approach.

Even if he worked a ton of overtime, would you work less hours? Or would you still find stuff to do with the freed up time?

There is little point to worrying about hours in the age of commit logs.

How do you work 19 hours a day?

That's 19 hours 'today', not necessarily each day. I've had days where I've arrived at work at 6am and then not stopped (save for short breaks) for 40 hours. Or worked 15ish hours at the office, driven home in 15 minutes, and then worked another 5-6 hours.

19 hours/day on average over an extended period might be a different story!

I know what it's like bud, I spent most of last month averaging about 18 hours a day on my new startup. I started to burn out within 3.5 weeks as the initial adrenaline wore out. Doing more regular hours now. Take care of yourself, and keep in good health :) Best wishes.

Sleep at the office.

Still, that leaves 5 hours for sleep? What about meals, showers, exercise, etc.?

Its not like that every day, it was just a particularly bad stretch where a lot of problems cropped up in the last day and simply needed to be dealt with (we're a billing company - the deadline for submitting a batch is final).

Ask HN: First employee hours