[dkador]

Of course we've thought of this (and a number of other hypotheticals). And of course we've discussed it, openly amongst the entire team as well as behind closed doors with our board and counsel. It does complicate things. In the end we felt like the positives (having Michelle on the team so we can take advantage of her strengths) outweigh the potential negatives. It could absolutely turn out badly. As with almost everything else in startups, we're making a hedged bet. And you're free to think we've made a mistake, of course, as long as you don't leave believing we haven't thought a ton about this. :)

It would be different if we were inserting Michelle into some rigid organization structure, especially if she was reporting to somebody other than our CEO. We don't have that kind of structure, though, and even if we did, we would never tell a frontline manager to hire somebody based on nepotism. That's a sure-fire way to kill a company in my book.

[tomkarlo]

Fair enough, as long as you're going into this with open eyes. It's not like most risks that startups take; inherently, most people wildly underestimate the risk that a personal relationship will go sour down the road. (If we didn't, a lot fewer people would get married.) I'm pretty sure if you ask most folks getting married what they estimate their chance of staying together is, they'll pick a number higher than ~50%.

Even if she's reporting directly to the CEO now, that raises its own questions, in particular for other employees. If I'm at her same level, do I feel like I'm going to get a fair shake if she and I are gunning for the same promotion? Down the road, as the organization grows, is she forever tied to reporting to the CEO? How do you ensure there's never a quid pro quo exchange that opens you to a lawsuit?

It's those kinds of questions that scare most organizations away from having direct reports romantically involved. It's especially fraught in a relatively unstructured organization like a startup where things like promotions and org changes can be fairly sudden and subjective.

[tptacek]

It's true that being romantically involved with a direct report is fraught, because the whole team will assume favoritism. But it's also obvious, and it does not take a management genius to come up with mechanisms both to avoid the problem and soothe the concerns of the team.

[tomkarlo]

If that was easy, it wouldn't be standard practice at corporations to disallow it. In most large companies, if you are in a relationship with someone in your reporting line, one of you has to transfer or leave.

Even if the reality is that there's no favoritism, it opens you up to lawsuits both from the people who are involved, and from their coworkers. If they break up, and then he demotes her or lets her go, lawsuit city.

I've seen this firsthand at a major venture startup (but wasn't involved in it myself) - a fiancee/employee decides to leave an officer for one of the other officers of the company. Disastrous for the company.

Anyway, it's their company, and I respect that they can do whatever they want - I only raised this issue because it happens fairly often in the startup world that a very tiny company wants to hire someone in a relationship with an existing employee, and there's a lot of issues you bring on board when you do that.