Ask HN: 19-Years-Old & Managing A Team of 10 - 20 People, Need Advice
Earlier this year, I was hired by a start-up Internet marketing company to be their copywriter. However, my responsibilities have always been much more diverse than simply writing copy. I've essentially been the company's jack-of-all-trades, and it is something I greatly enjoy, as each day is truly a new day and nothing gets repetitive.

About a month ago, I was given the responsibility of heading a massive project that will essentially serve as the foundation upon which the company will rely on to grow larger and more profitable. Due to how large the project is, it requires quite a few employees if I am to meet the goal set by my boss, the CEO. As of today, I've hired 3 people, and am managing an additional 7 of our in-house employees. Lately, everything has been fine and well, but it is very apparent that for me to meet our goal, I will need to ramp up the number of employees working on the project.

And, with that... I run into a problem. My boss and his partner have personalities that are as polar opposite as can be. My boss is very hands off, but takes no bullshit, despises laziness, and when he wants something done, he demands you do it by any means necessary. However, his partner is a micro-manager, even in things he has no experience in, i.e this current project. He fastidiously manages a profits and loss sheet for every project we're running -- which I realize makes business sense -- but, it lends itself to him demanding maximum output from minimal resources, no questions asked.

With this particular project, profits will not start rolling in en masse for a couple of months after the infrastructure is in place. My boss knows this, as he understands what goes into it and has experience in launching similar projects of his own in the past. If I am to pander to only him, I would simply go out and get the employees I need to reach our goal. But, I can't pander only to him, especially since his partner sat me down and asked me to try to play the middle ground between him and my boss. However, the partner doesn't realize how long it will take for money to start rolling in, so if I continue to hire employees and he doesn't see money rolling in, he will automatically assume we are getting minimal output with maximum resources and want to either scale back the number of employees or can the project completely.

In my honest opinion, I need more employees. If we are to ultimately meet our goal, it is necessary. The current number of employees simply can't meet up with the work load, even if they were machines and pulled 80-hour weeks. But, again, if I go out and hire 7 more people (how many I intend on hiring), the partner will be very wary and most likely take it as me rejecting his input in everything, which I'm not doing.

Would you guys suggest I sit down with the partner to explain how I see things inside and out with regards to this project and it's needs? He listens, and is open to most things, so I think that if I came up with a report for him to read that justified the hiring needs, he'd be okay and at ease, and I could present the report to him the day before we met to discuss everything so I could simply address his concerns rather than explain everything to him AND THEN address his concerns in one swoop.

My main concern is not crossing either my boss or his partner. I don't want to step on feet, or indirectly infringe on their positions of authority, which I could easily do if I didn't hire the necessary employees because the boss believes I should do what I need to meet our goal or if I went out and hired the employees I need because the partner is wary. Any advice would be appreciated.

Also, I did think of a way to get more out of our current employees. Or, at least, one position within the many positions. Vaguely, the goal is to put up 1,000 websites by the end of summer (or the start of August) that are "profitable." To do this, we need designers, coders, me for content and then people to rank these websites.

Right now, the designers is where we're hitting a rut. To create 1,000 websites by the beginning of August (minus the ~50 or so we've created already), our designers as a collective need to design ~27/day, or ~135/5-day work week. Between 3 people, that's just not possible judging by their current performance. Each designer, on average, generates 15 designs/week. So, to generate ~135 designs/week, we need ~9 employees generating ~15 designs/week. Due to the nature of the websites, the designers can essentially design 1 template and replicate it 5x over by making minor alterations to their designs (mainly in the name of the sites and the phone numbers included on the sites). But, no one is really doing this because all of them have told me that they'd rather switch up their designs for this reason or that. I am an understanding person, and coming from a background informed by creativity (being a writer, and all), I get that they don't want to make the same design over and over and over because they're not able to be the artists that they are, which strips the fun out of what they do entirely. I don't like this, because I my personal philosophy is that you should enjoy your job, not wake up and despise it, which I'm afraid would happen if I demanded each designer make 1-template and do the replications, and then rinse and repeat for each new set of sites, but it would increase their productivity by a lot.

Should I stop being their "friend," and be their boss, and just tell them that they must do the replications? Mind you, this would mean I'm ignoring my personal philosophies. But, does that even matter in situations such as this? In a business context, whose success and failure depends on profitability more so than remaining 100% philosophically pure personally?

As you can tell, I've been thinking about this stuff a lot. I'm looking for people who have been in similar situations or have a lot of experience in managing bodies of people, so if possible, just throw a line or two about how your experience will give your advice credence.

Thanks, HN! You guys have been great so far for this type of stuff.