Did the team contemplate in making this offer that if something went sour in that relationship, you'd end up with a CEO who has both personal drama and potentially a very difficult situation in the office, given that she'd be reporting to him? How did your corporate counsel feel about this? Your board?

If she's not reporting to the CEO, how does her new manager feel about having a team member who's his bosses' fiancee? Would he be comfortable firing her if she fails to perform?

I know this seems hypothetical, but I think anyone who's been around startup has seen some variant of this play out multiple times. It's bad enough when it's friends; it's even more treacherous when it's a fiancee/wife.

I'm biased, as I work with my spouse, but this is I think an overblown concern. People leave companies for all sorts of reasons, many of them dumb. They do not need to have made a lifelong personal commitment to their manager to find those reasons. Also, people do not need to have made that commitment in order to access their unprofessional self; normal team members find ways to be deeply unprofessional without entangling their relationships into their companies.

Yes. Strictly speaking, if you get into business with your significant other, you are increasing the cardinality of the set of things that can go wrong with your team. For people that think like us, maybe that's where you stop thinking, and if so, fine. But the set we're talking about is very large, and I also know high school statistics, and so can observe that the relationship stuff is unlikely to be the event that blows up your team.

Believe in working with your spouse (or close friends, or whatever) or not. Either way: it has nothing to do with negotiating for a job, and it's a little creepy to bring it up here.

Well as long as the reporting structure at work is the same as the reporting structure at home I'm sure it can work. When they are reversed its a recipe for disaster.

I'm not sure what you mean here. The working relationship I have with Erin is nothing like my home relationship with Erin.

I worked at a company where the husband was the CEO and the wife reported to him. But at home it was pretty clear the wife made the decisions and the husband reported to her. As a result we got to experience the CEO making some decision which the wife disagreed with, only to have the decision changed the next day after they had spent some time out of the office. It was uncomfortable for everyone, and ultimately fatal to their marriage.

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.

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.

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.

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.

Yes. Maybe a whole separate blog post coming on that :)