What are some examples of things sales reps can do to be 'pushy' without irritating a customer or prospect?

Prospects stop responding or "go dark" for a number of reasons. But that doesn’t mean you have no control over getting them back above water to give an update and keep the deal moving. Here are six specific next steps you can take for that prospects who’s gone dark (without coming across too pushy).

Try a different channel
If you’ve been pounding them with voicemails and email, try Twitter. Or LinkedIn. Or even a letter or overnight package. If you mix up the channels you’re using, you not only increase the chance that your message will get noticed, but also have a higher likelihood of tapping into a channel that your prospect is more comfortable with. For example, I get a lot of voicemails but they take longer to return. Send me an email and you’re likely to get a faster response.

Try a different contact
If the primary contact you’ve been working with has gone dark, it may be for a reason other than declining interest in the deal. Who else in the organization could you contact to find out? Someone else on their team? An administrative assistant? Be careful not to go over their head and contact their boss, as that could make things more complicated. But based on your knowledge of the organization and how it works, there are typically several others you can contact to at least get an update and help move the deal forward.

Share something unrelated
Your communication with prospects doesn’t have to be all business. One of the best ways to get a quick response from a prospect that’s gone dark is to share something completely unrelated to the deal, but highly relevant to the prospect. It gets their guard down, and makes it easier & faster to respond. And most likely, they’ll respond quickly with a comment on what you shared with a quick sentence or two on the actual deal.

Try a different angle
Are you sure about the reason your prospect wants to buy? Have you focused on a particular benefit or outcome that they’re less excited about? It’s possible the deal has stalled because they don’t prioritize the benefit you’ve used primarily in the process so far. But if you offer multiple benefits, perhaps a different angle can get the prospect back on track. This means understanding their needs well enough to enumerate and rank the various outcomes your prospect needs, and which you’re best able to address and provide.

Engage their influencers
This doesn’t mean their boss. It does mean others in the buyer’s ecosystem who can influence them. Analysts, peers at another organization (especially if you already have a good relationship with them), someone else in their network you know via LinkedIn. These influencer connections don’t have to be business related. Figure out who you know, who they know, who influences them, and pull the right levers to get progress.

Move on
Sometimes, a prospect that’s gone dark is an implied “no” to the deal. If that’s the case, move on. Work on the next deal. Stop beating the dead horse, which at this point is only keeping you from working real business. Knowing when a prospect can be resurrected and when it’s time to move on involves plenty of gray area, but this might be the most important tip of all to keep you productive