Why Being Fearless Will Get You Everywhere

Updated: November 16, 2010

Let's break down the different modes and circumstances of communication and look at how we can display fearless salesmanship in each:


If you're afraid to sound silly and face rejection, just find another line of work. You can be anyone you want over the phone, and the art of conversation has been all but lost, so get used to shocking people out of their malaise en route to productive dialogue.

  • Gatekeepers: These people control the most direct route to your target decision maker's ear, yet they are constantly dismissed by average sales reps attempting to deceive their way to the promised land. Trust me, you're not the first person who thought asking for the CEO by first name was a clever way to sound like you're old chums, and nobody believes they're "expecting your call" for a made up appointment. Slow down, and get ready to embrace some very productive awkwardness.
    1. Engage: This may not sound fearless at first, but simply saying hello and waiting for an answer to "How are you today?" can be gut-wrenchingly awkward in a culture where these pleasantries are regularly bypassed. The ensuing startled pause will compel you to abandon niceties. Fight it.
    2. Win them over: Listen closely for tidbits you can reference next time you call (frustrations, recent milestones, etc), and wait for the opportunity to inject some positivity into their day. "I'm always doing great! I get to talk to new people and hopefully make some sales every day. Life is good." Now they're starting to like you and you've done something essential that average sales reps are scared to do - admit it's a sales call.
    3. Ask for help: They'll ask "What is it that you sell?" Average sales reps insult the intelligence of the gatekeeper by deflecting this question and asking to discuss it with the decision maker. Not you, you're fearless enough to face rejection early and admit you don't know everything, so you come with "Maybe you can help me out. We help companies like yours (save money, increase revenues…whatever your value proposition). Who is the right person to speak with, and what's the best way to reach them?"
    4. Gain an ally: Forget leaving a message that won't get returned. Muster the gall to request they do the dirty work for you and actually schedule the appointment. Try something like "I don't want to waste his time playing phone tag. Do you think you could get me on his schedule and let me know when to call?" Again, wait out the uncomfortable silence and wait for the agreement.
  • Decision Makers: If you have it in your head that purchasing power deems somebody in any way superior to you, then you'd better have a product that sells itself, because people don't just buy from people they like. They buy from people like themselves. Counter intuitively, daring to be different with decision makers means approaching them equals
    • Rapport: Sharing is caring, and research is key to determining if it makes more sense to either find common ground quickly or assert your own quirky individuality. Any cues you can pick up online or in person about mutual non-professional interests or associations are natural conversation starters. If there's nothing to work with here - and don't force it - then take the opportunity to make yourself more interesting. If you don't share passions, introduce your own eccentricity and open their eyes to a new hobby or sub-culture. "I just got back from our yearly polka lovers Belgian beer retreat" makes for a much more memorable introduction than talking about the weather.
    • Following up with flair: Keep the dialogue interesting by referencing personal items first and mixing in a somewhat goofy but inoffensive picture, video or article with a "This made me think of you" pretext. Get a smirk first, and then get to the next step. Uber-professionalism is boring for even the most severe curmudgeons.
    • Closing: I can't emphasize enough the importance of embracing uncomfortable moments, such as the awkward silence that follows a closing question. No bail outs either. Ask for the business as if you assume the yes and hearing it is just a formality. A casual "You ready to get started?" will elicit a casual yes or an honest objection. If it's an objection and you've adequately built the relationship, then you can get away with a bit of callousness in your challenge, like "What are you afraid of?" It's not insulting if it's from an old friend. It's enticing.


  • Not having the decision maker's direct email address is OK. Most people assume the unglamorous info@ inbox and ‘Contact Us' form inquiries are only semi-monitored by a lowly admin, but the truth is you'd be shocked how many high-level managers get these messages directly because they don't trust anyone else's filter.
    • Subject line: Think like a spam filter. In five words or less, you've got to capture interest in a way that says "this is an important message intended for you specifically that should not be ignored". I suggest this format: "Does (Target company name) want to (benefit statement)?" Track different subjects you've used for a particular prospect in your CRM and gradually progress from the somewhat mundane to the absurd.
    • Body: State your purpose with flair, but without dancing around the issue. If your goal is to speak with the right person or get more information, just say so. Attention spans are too short for pleasantries at this point. Try "You guys at (company name) sure do make it hard to track down (person or info)….Can you please pass this along and get back to me so I can stop banging my head against a wall? I promise not to waste anyone's time." None of this "I hope this email finds you well" crap is going to get you lifted out of the pile.
  • Having their email is better. Sadly, many managers in a position to make purchases have stopped taking unscheduled calls altogether and often actually request an intro email on their voicemail message.
    • Subject line: I've actually found that the simple one-word ‘Introduction' subject line is remarkably effective, but assuming you tried this already, more gutsy plays acknowledging your intrusion with something like "(First name), a sales email actually worth opening" or mentioning a competitor "(Coke…if I was emailing Pepsi), doesn't want you to read." Make it look irresponsible for them to ignore.
    • Body: Again, focus on grabbing attention in the intro or the rest of your email won't matter. One strategy I love is the threat of persistence. Something like "If you give me a good reason why you're not interested then I will go away." You may get a "OK, we're not interested", but at least that's the start of a dialogue.
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