50: This Question Got Me 3 Demos in 1 Day
A month ago, I left PandaDoc and joined Mailshake to build their outbound team.
I’ve been heads down trying to figure out what messaging will resonate with our ideal prospects. It’s especially important since we’re in a crowded space.
Here’s a simple strategy I used (and am still using) for this.
Read on to see how this strategy *accidentally* resulted in my highest converting day.
The magic question
The (accidental) results
The Magic Question
The idea behind it is simple: instead of trying to change someone’s mind when they aren’t doing what you want, ask “what would it take?”. Oftentimes the answer is much simpler than we think.
Check out the article linked above - her examples explain the power behind it far better than I can.
So I figured I’d put it to use on my prospects.
I created a list of 50 and asked “what would it take?” for them to switch off their current provider (aka my competitor).
Here’s the exact template I sent via LinkedIn DMs:
Let me preface this by saying I’m not trying to sell you anything or book a meeting haha.
I was hoping to get some feedback from you as a persona I would normally sell to…
I’ve started to build the outbound motion at Mailshake. We’re a competitor of tools like X, Y, and Z - I’m sure your team uses one of those.
I’m genuinely curious what - if anything - would it take to for you to consider an alternative?
Any feedback would be massively appreciated.
Out of 50 people, 12 responded. 3 even offered a Zoom call for in-depth feedback.
They told me everything from how & why they bought my competitor, what they do & don’t like, and what it would take for them to switch.
I even got their feedback on value props, emails, and call pitches.
This helped me paint an incredibly clear picture of my ICP.
The (accidental) Results
The crazy part is… 3 of them opened up about genuine pains they had and actually wanted to book demos.
Here’s an example:
Taking the approach of “I just want to learn, not sell” in the first line of my message caused them to bring their guard down, read my entire note, and feel comfortable giving honest feedback.
It also helped that these were sales leaders further along in their careers than I. They tend to like paying it forward if you're respectful and genuine.
This exercise is worth doing whether you’re building messaging from scratch or have a successful outbound team already.
I’ve been in both shoes and honestly, should have done this far more when I was with PandaDoc.
Even though I thought our messaging was pretty nailed down, it never hurts to get more info from your ICP on how they want to be sold to.
And hey, you might book a few meetings while doing it.
Thanks for reading,
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