This is one of the hardest things to do in sales. Let’s make sure you know how to do it right.

Things are lined up nicely. You have a good relationship with someone below the executive level who’s telling you what you want to hear, saying it’s “with their manager”, or being just nice enough that you stick around even though you know they can’t get the deal done. Here’s the kicker: They will never be able to say yes, but they can definitely say no and ruin the whole deal if you upset them by going over their head to the real decision maker. 

You have four options. Choose according to your circumstances:

Start high

Yes, it’s a bit late for this, but I’m adding it here to reinforce the importance of starting your prospecting at the highest level possible and getting referred down. If you prospect into the C-suite without trying to sell to them, and you ask for a referral down, you have an open door to go back to if the deal gets stuck. Also, after getting referred down, you can let the person at the lower level know that you’ll follow up with the executive who originally referred you, as a courtesy to them.

Leverage your manager or another executive

This isn’t my favorite approach, but I’ve seen it succeed from time to time. At a certain stage in the sales process, have your manager or VP reach out to their peer at your buyer’s company, while you stay with your main contact at the non-executive level. Explain to your contact that this is part of your process; once a deal reaches a certain stage or size, your VP gets involved. This explanation allows you to remain in good standing with your contact since you’re not the one who went over their head. It was your VP, and there was nothing you could do about it. The main issue with this approach is that it diminishes your value and takes you out of the driver’s seat for the deal. If the deal continues to move forward, your manager or VP will need to play a major part in it, which isn’t ideal.

Lead the process, don’t follow

This is my preferred approach. Instead of asking your lower-level contact for an introduction to an executive contact, you tell them you’re going to reach up and why. This takes a certain amount of confidence (which you have), and you need to present it the right way. It works well on employees who aren’t used to making decisions. Position yourself as the expert. Tell them straight up (or at least have the mentality that) “I’ve seen this process so often, and when the process goes well, this is what happens… nINSERT RELEVANT INFO HERE], which is why it’s so important to get your executives on board now.” Again, you need a good reason as to why you need to engage with the executives so that once you’re there you don’t waste their time. Deliver it properly and it will work wonders.

Create another reason to reach out to an executive

This requires additional research on the account even when you’re working through the sales process with your non-executive contact. You need another reason to reach out to an executive — one that is distinct from the conversation you’re having with your contact. For example, if you can find a quote from a CXO in which they talk about something from a strategic standpoint, you can reach out to them and say something like, “I’ve been working with aCONTACT’S NAME] to address some of your �NAME THEIR NEEDS] and iHE/SHE/THEY] has been a pleasure to deal with. I noticed that you recently said YINSERT QUOTE], which is why I’m reaching out to you directly. It sounds like a conversation would be very helpful at this point, so I’m wondering if we might aINSERT MEETING REQUEST].” This way, if the email gets back to your contact, they’ll see that you tried to make them look good and that you have an entirely reasonable reason for reaching out.

Again, there’s no one-size-fits-all way to go over someone’s head, but hopefully one of these suggestions will help you navigate this tricky situation.