The best way to get your name back into someone's head is by taking an interest in their work. Endorsing their skills/liking their new job/commenting on their new article are all great ways to do this. A few of these actions tells the person that you're interested in them and appreciate their thoughts.
If you haven't talked to this person for a while, it's useful to find out what they've been up to and let them know how you've grown. In a biz dev context, this sets the stage for discussing potential work together. However, it's best to take greater interest in your old contact's activities than to bombard them with every update in your life. Twitter can be a great medium for these conversations, allowing you to expand on an existing "conversation" your contact is already in. Alternatively, sending a (very!) brief email or LinkedIn message can kickstart things.
Once both of you have established context for your new relationship and rebuilt some rapport, it's time for one of you to make an ask.
Often your old contact might make the first move! If you've struck up a decent convo, they may need someone exactly like you and ask if you could give them advice.
However, most of the time you'll need to nudge the conversation forward. The key of a good ask is to make it small and actionable: you can't ask someone to track down a new client for you and deliver you a contract, even if you are offering a fat referral. Instead, this is a good chance to cement your new relationship. Typically, I let them know that I'm trying to find new business in their space and am wondering if they have any advice on positioning. An ideal ask might look like this:
Hi Kym, Really enjoyed that [article/earlier Twitter post/etc.] you posted the other day. After our brief [earlier LinkedIn message/email] the other day, I started thinking more about [your company's] efforts to reach out to [industry-specific vertical] clients and realized we could really improve quite a bit. Specifically, I think we are [something you think could improve or are interested in. This shows you have genuine interest and, for most people who care about their space, it'll be a sure-fire hook for a convo.]. I was wondering if you might have 15 minutes to do a quick Hangout or Skype to give me your feedback? Would really appreciate your help! Best, Alec
Once you get talking with your old contact, if biz dev doesn't explicitly come up, make sure to close out your conversation with a more explicit ask.
- Can you think of anyone in your network who needs our services? (If the answer is NO here, it's interesting to find out why. Can be a great way to hone your marketing.)
- Is there someone else you'd recommend I talk to?
Don't be disheartened if your old contact doesn't have any immediate work for you: that's normal. But make sure you start getting connected to more people in their network. Ideally, your old contact becomes a new node in your expanding networks!