When You Earn The Right To Ask

My friend “Kate” asked me to a business lunch to meet her friend “Molly”, who had just started a venture capital fund and was looking to grow.

Kate is one of the savviest people I know and has a great track record for making connections—and Molly sounded like a powerhouse—so of course I agreed.

Molly regaled us with engaging stories about her portfolio companies and bemoaned how hard it was to raise capital.  At the same time, she also quickly dismissed our ideas for building the reputation of her fledgling company.

She seemed singularly uninterested in spade work—the long-term bit-by-bit building of relationships and pipeline that enduring businesses invest in.

Instead, she went for the quick win: she blithely asked us for $250,000 each to buy into her new fund.

Seriously?

My ego was flattered that she thought I had a spare quarter million sitting around waiting for high-risk ventures with people I don’t know.

But the rest of me was aghast.

You get to know your client and their needs before a big ask—you wait until you’re clear that your interests align.

And it doesn’t matter whether we’re talking investments, charitable contributions or consulting: very few clients award a $250,000 contract on the basis of a single meet-and-greet they didn’t request.

No, Molly walked away without a sale and, more importantly, without seeding a mutually beneficial relationship.

Because I was pretty darned impressed with her drive, her success stories and the big idea behind her fund—I could have easily introduced her to others who might be thrilled to pony up the price of admission.

But once she clearly demonstrated her preferences and character, it was over. (Her follow-up: “So, are you in?”)

Had she just asked herself one small question, she might have changed the outcome: have I earned the right to ask?

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