Next NY’s “Jumpstarting Sales in Your Startup” panel last night featured Mark LaRosa of QuotaCrush and Jeff Stewart of Urgent Career. Though the group was lively to begin with, the question that generated the most buzz - "What are the best ways to get past a gatekeeper?" - was such a classic that I had to post the best responses.
Here’s the best of the best that came out of the crowd last night:
Give the gatekeeper the benefit of the doubt. Most salespeople assume that an assistant doesn’t have the time, judgment, or influence to help them, and therefore ask immediately for the decision-maker. Huge mistake! Treat every assistant with the courtesy and respect of a CEO. Doors will magically open for you.
- Treat the assistant like a human being. This is obvious, but most assistants don’t aspire to be assistants forever. Google their name. See if they blog or tweet. What’s their web presence? Find something that they are genuinely interested in and run with it.
- Use your arsenal. Make a joke. Play good cop/bad cop. Talk about the weather. Mention a tidbit you saw in the news. Ask about their company’s latest release. Ask if they’re running the company yet. Whatever your style, get the assistant on your side. After all, they’re controlling your access to the company. There’s no need to make them enemy #1.
- Write down the assistant’s name. Refer to them by name, every time. Be friendly, polite, and direct. Remember that you are not yet their highest priority, and being impatient, self-righteous, and vague is never going to get you there.
- Be honest and forthright about your solution. Value the assistant’s time - it’s just as important as the decision maker’s. Explain to them up front what you are calling about and why you think it will add value. Don’t hang up and try again if your target is unavailable – it’s disruptive and dismissive. Worse, you’ve wasted an opportunity.
- Ask for help. The more you can engage the gatekeeper in the process, the better. Ask the assistant about the best time to call, the easiest way to get in touch, direct numbers, cell phone numbers, etc. Ask if it’s better to leave a voicemail, leave a message, or just to call back. But before you do that…
- Assume the assistant is a decision maker. Believe it or not, the assistant’s job isn’t to keep you at bay. Rather, their job is to discern potential value for their executive and/or their company. By that logic, you should involve the assistant’s judgment as much as possible. Gatekeepers have an ear to the ground about every aspect of the business. Ask them about their pain points. Where would they see the most value added? What’s most important this quarter? Next quarter? Next year? What’s their growth strategy and what are their bottlenecks? What’s their biggest frustration? Assistants offer unique insights that can help you refine your pitch.
- Ask who else is involved. Gatekeepers have the ear of everyone that will be involved in your sale. They know who you should be talking to. Ask if you are targeting the right person. Do they know anyone that might be of assistance? Who should you talk to first and why? Who is the ultimate decision maker? Let the assistant paint the relationship structure for you and guide you up the ladder.
- Alleviate their burden. Assistants are responsible for sourcing and evaluating vendors. If you’ve called them at the right time, you’ve eliminated their legwork. Let them be responsible for walking your sale through the company. Don’t blow it by presuming that they won’t be involved in the process.
- Let the gatekeeper advocate. If you’ve effectively engaged the gatekeeper, they will be your advocate throughout the entire sales cycle. Let them make introductions on your behalf. Ask about the best ways to engage various decision makers. Ask their opinion on what’s most important to each decision maker. Use them as a strategic sounding board as your deal goes through the pipe. The more they are engaged in the value, the more value they add to you.
Got any more of your own? We’d love to hear them in the comments.
About the Guest Blogger: Lauren Gilchrist is Urgent Career's "Jill of All Trades," managing operations ranging from finance to marketing to strategy and beyond. A young entrepreneur interested in the intersection of sales and technology, Lauren plans to contribute regularly to Urgent Career's growing web presence as an authority on all things sales. Look for more of Lauren in the coming weeks.


and its target-rich selling fields.