Mastering the Art of Professional Dating

My Little Black Book

My Little Black Book

In case you missed my Lunch and Learn at JVS in which I opined about the art of professional dating, I wanted to share a few of the FAQs.  You may be wondering what my credentials are here – after all, I haven’t been on a date with anyone but my husband in almost ten years.  However, I am happily employed after a quick job search after other happy employment.  My networking pursuits have made me a “regular” at three coffee shops.  I got skills.

Conventional wisdom tells us that the best opportunities will come from the outer realm of your network.  It makes sense if you think about it.  You know most of the same people as your co-workers and close friends, and you will find out about the same opportunities.  The good leads come from someone who moves in different circles.  So, when you lock eyes with someone across the room at a workshop, or a LinkedIn profile catches your eye, here are some tips on how to get the coffee on the calendar.

1.  Will it be awkward?

Not unless you, personally, are awkward.  It is actually super flattering.  People love to talk about themselves and spout off on their expertise.  That is why we blog.  However…under no circumstances should you say, “Hi Nikki, can we have an informational interview?”  THAT would be awkward.  It’s best to make a very straightforward request: “I’m really interested in transitioning from programs to the development side of things.  If you are available for coffee in the next few weeks, I’d love to pick your brain about how I can present transferable skills.”  That is a very easy request to say yes to.  People also like to be helpful.

2.  What will we talk about?

That is entirely up to you, but remember that you are driving the bus.  Make sure you have some questions prepared to get the conversation flowing.  There is no need to give yourself a migraine coming up with a list – use this one.

3.  Who will buy the coffee?!?!?!

You will show up 20 minutes early.  20.  You need time to grab a table, get yourself set up, and keep an eye out for your date so that they don’t have to worry about finding you.  Before you do all this, get your own.  When they arrive, they will get theirs.  Thus, you avoid awkwardly shuffling around the cash register.

4.  Can I ask someone for a conversation if I have applied for or am going to apply for a job at their organization?

My experience is in small nonprofits, so I can only speak to that sector – in which we do not have HR staff and are generally hiring the positions we will supervise while also doing our full-time job.  Tread very carefully here.  If it looks like you are trying to skip the line in the interview process, you’re screwed.  It is not ok for you to reach out for “a quick conversation to help me decide if I would like to apply for the job.”  If you are looking for a broader conversation from someone in another department, then totally go for it.  If you are reaching out specifically because of the job, I do not approve.  Note – this is different than applying for a job and asking a mutual contact to put in a good word for you.  I totally approve of that, and it can be very helpful to both you and the person doing the hiring if they are having a hard time sorting through the stacks.

5.  How do I stay on their radar?

At some point someone will share a job opportunity with your new friend and ask for referrals.  Wouldn’t it be great if they thought of you?  The first step is to immediately thank them for their time.  In that email, it would be totally appropriate to reiterate what it is that you are looking for and to ask them to keep you in mind if anything floats through their inbox.  At this point, you can be assets for each other.   You can pass on articles that they may find useful.  You can share their volunteer opportunities.

If you really get the hang of this informational interviewing business, staying in touch can be a lot of work.  It can be pretty easy to forget about someone over time.  that is why I recommend this Networking Follow Up Chart, originally developed by Liz Leberman for an earlier JVS Lunch and Learn, which is summed up on this Career Moves blog post.