How to Sell Me (Not), I Dare You to Try

“Thanks for the meeting, no I don’t want to hire you to consult for my company.”

Having to sit through an increasing number of sales pitches from startup consultants these days, I thought I’d summarize the points that worked in selling me and what just turned me off. At the very least, next time someone tries to pitch me, maybe I’ll just send them a link to this blog before the meeting.

At best, I’ll formalize some points to improve on my own sales pitch.

Tip #1: Don’t assume.

I understand that I’m a bit of an idiot.

I’m new to this. I didn’t go to Harvard. I don’t have a million dollars. Your fine Italian shoes clearly indicate your business superiority. I am destined to fail without your advice.

Still… please ask me what my situation is before telling me how to correct it. If you’re telling me that my pitch needs improvement, I’d appreciate if you’d listen to my pitch first. If you’re telling me I don’t have the right target market, please make sure you know what my target is first. If you’re telling me I need my teeth whitened, please ask me if I live in LA first.

What I’ve learned: Ask more questions, keep your mouth shut, verify pain points before selling.

Tip #2: Don’t tell me to conserve costs.

Ok… that’s actually really good advice for startups. It’s great advice.

But seriously… if you tell me I shouldn’t waste money hiring an attorney to go over tax issues and then tell me I should hire you for $250 an hour to work on my corporate culture, I’m probably not going to hire you.

I have hard problems. Don’t sell me on soft, fuzzy solutions I’m not convinced I have.

Perhaps I’m radically mistaken, but unless my corporate culture can fix my tax issues, I’m probably going to hire an attorney before I hire you. Instead, demonstrate some value by telling me how to hire a $100 CPA instead of a $1000 attorney to fix my tax issues and then we’ll talk about your services.

What I’ve learned: Umm… don’t undermine yourself? At least not in the same sentence.

Tip #3: If you can’t shut up, ask questions.

I’ve just said/done something stupid.

You’ve caught me in the act.

You know how to fix it.

Congrats, don’t tell me. Show me.

Ask me questions to guide me to the realization that I need help in this area.

  • “Have you tried ______?”
  • “How many customers have you validated that hypothesis with?”
  • “What could you do to get customer feedback earlier in your development?”

You’ll avoid me getting defensive and you’ll impress me with your keen interpersonal skills.

What I’ve learned: Socrates was a bad ass.

Tip #4: I might not be an idiot.

As I mentioned before, I’m a bit of an idiot. But I also might not be

I might be asking you what participating preferred stock is because I don’t know. I also might want to see if you can explain it without being patronizing.

I might be changing the topic to see if you bring me back on point. I might be asking you to setup a meeting with an outrageously well placed VC contact to see if you’ll be honest and suggest an alternative within my reach.

I might even be picking up the tab to see if you'll even offer. Click To Tweet

As I said twice now, I still might be a bit of an idiot. But if you don’t treat me like one, I’m less likely to assume you suffer from the same defect.

What I’ve learned: I’m a bit manipulative. And again, don’t make assumptions. They’re usually wrong.

Tip #5: Read a book.

Lastly, go read some Dale Carnegie. He’s the king of the soft sell.

If you’ve read it and you think it’s all about smiling, remembering names, and learning to lie well enough to stroke some ego then you probably didn’t read it carefully enough. If you can name the ancient Chinese philosopher that Carnegie references (and I think most of the book draws from) then you’re hired.

(btw: the answer is here.)

What I’ve learned: I’m a philosophy geek.


There you have it. Now you know how to sell me. I dare you to try.

Discussion (3 comments)

  1. Sue Lampard says:

    As usual, your blog is not only an enlightening read Tristan but also consistently dry and entertaining. The information you give applies to more than ‘startups’, it could improve almost every aspect of one’s life.
    Getting your updates is something I always look forward to. Thanks!

  2. Pingback: YWord Blog: Sage Advice For Selling Your Own Success | Yworld

  3. Matthew Borghese says:

    Great advice, and like Sue says, it applies to more than just “startups.” Learning to educate people without patronizing them is a key life skill that will get you far in business (and in your social life as well).

    I’ve posted a link to this on our blog as well, so we can share it with our community.

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