3 Ultra Creative Strategies to Get Face Time with Your Toughest Prospects

Like everyone I know, I have a few things I do especially well. I can expertly negotiate out of at least 50% of my speeding tickets, can type consistently at about 90 wpm (riveting, I know), and a few other things, including how to think of creative strategies and grand gestures. It’s always been something that has come easily to me and is also one of the most fun things to pull off, when executed flawlessly. This specific talent has been particularly beneficial to me, especially when it comes to setting sales appointments. My creativity has gotten me some of the most impossible meetings. Here are a few to try and the stories behind them.

Technique #1 – No time to meet? Offer to meet your prospect during a mundane errand.

When I first started out in my sales career, I had an opportunity to win a deal that could make my entire year’s quota in a single transaction.

I had all the buy-in I needed from the key influencers, but the missing link was getting to my decision maker, which proved to be impossible.

The head of this agency was someone who was always on the road, never available, and felt that they solution they had worked. Despite the urging of her team and all of my champions, I couldn’t get her to return a call or email, or reach out with the encouragement of her team.

I finally got the nerve to show up at event at which she was speaking, and when she met me kindly with the words of, “I know you’ve been trying to get on my calendar, but forgive me, I’m just so overbooked…”, I got creative.

Not only was she always impeccably dressed, but she had impeccable hair. So, I took a leap.  “Can I say that your hair color is incredible? I’ve had highlights for years, so can appreciate how hard it is to find the right colorist.”

Now, you may be rolling your eyes at me and my superficial comment, but it connected us immediately at a different level.

We started to trade some stories on the topic and I ultimately suggested that I join her for her next appointment to have mine done as well, and we could discuss what I thought would be so beneficial to her. She agreed. We met. We got a hefty portion of the deal.

Technique #2 –When they’re traveling, say you’re traveling too (even if you’re not).

I was recently introduced to a Chief Information Officer that was a key player in deciding the fate of a deal on which one of my reps was working.

After a few back and forth emails, we decided it would be beneficial to meet. I suggested a time for the following week to meet in Washington D.C., where we both reside, and was met with the reply that he was on the road the next few weeks, but that we should meet in a month.

My rep, who was cc’d on that email, was disappointed that he would have to wait another month for progress on this deal. He, like most reps, would have agreed, and quickly sent a calendar invite a month out without thinking thoughtfully.

As I sat in our San Francisco headquarters, I instead wrote that back that I, too, was on the road most of these next few weeks and wondered if we would cross paths sooner. I said that I was currently in San Francisco and I asked where he was headed next. What came to light is that he also was currently in San Francisco, and we ended up meeting the next night to discuss our opportunity.

That detail alone was able to speed up our deal by a full month, if not more. Time kills deals, as they say, so who knows what could have happened had we waited an additional few weeks.

Technique #3 –Need to get the attention of a new executive? Time to get really creative (and personal).

When any company hires a new executive, that individual is faced with two certain things: a sea of vendors that want to be the first to land a meeting and a deadline for making an impact with their own ideas and strategies.

My rep had recently been working on a deal that was at the finish line. Contract printed, pen in hand, ready to go. Until, our signer was also ready to go. He packed up his bags, moved to the next job and we were (tearfully) left waiting for his replacement.

Three months later, two replacements arrived – a new head of NA marketing and a new CMO.

We gave it a few months to see if the meeting would organically occur (that happens all the time, right?), and then we got serious.

If you follow my posts, you know that I’m a big believer in Show Me You Know Me (SMYKM), so we scoured her social profiles for any commonalities we could find or any shred we could use to open conversations.

We came up empty handed, but what we did uncover was that she attended a relatively unknown university abroad.

So, we called the school and had them ship us a sweatshirt. We then grabbed a $25 gift card to one of the most popular restaurants near the head of marketing’s office.

We then hand-wrote two notes – one to the CMO saying we thought she could use something from her alma mater, and one to the head welcoming her to her new professional neighborhood – and said that we had worked with their teams for nearly a year and were looking forward to getting to know them.

What ensued was magic – responses, inquiries on how we could help them, and meetings that wouldn’t have occurred (their words, not ours!) without our thoughtful gestures. Not only did this net us the meetings, but it demonstrated the level on which we think about our clients.

Sam rose from being an individual contributor in sales to running an enterprise sales team. She also created ON24’s mentorship program, and has seen these tactics successfully used over the course of many years and across all industry types and company sizes.

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