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Outside the Box: 13 Unconventional, Bold Sales Maneuvers
Blog / For Sales Pros / Jan 3, 2018 / Posted by Tony Hughes / 6388

Outside the Box: 13 Unconventional, Bold Sales Maneuvers


1) Deal Interception

You could call this set of circumstances a perfect storm of multiple trigger events meets compelling event. Seconds before a competitive deal closes, you counter with the value of your solution, stealing the ball (the deal) right out of the competitor’s hands. It’s a risky move, but if you’re able to establish FUD (fear, uncertainty and doubt) or spot a flaw, you can leverage it to your advantage.

Sharp executives are often the most ambivalent in the 11th hour, taking another hard kick at the tires. Often software vendors combat this with dropping the price – but positioning your solution on value is a more sophisticated play.

The deal interception, when correctly executed, can shorten an 18-month sales cycle down to mere weeks – especially if it is for an existing account, and the need is NOW.

2) Hail Mary Pass (or Kick)

Lob a call into the CEO’s office. Turn their EA into your best friend through the respect of an honest pitch. Take advantage of the demand created by scheduling an on-site meeting between their CEO and your own. The hail mary pass requires courage, boldness and internal selling to obtain buy-in. The authentic wingsuit base jump happens when you land that 1-on-1 meeting yourself (combination of #3 and #4).

3) The VITO Envelope

Place a signed one-pager inside a manila envelope. Hand address it to the key executive and send it by courier. Another method is by FedEx delivery to the Very Important Top Officer (VITO). These are so rare that the executive will typically always read them.

The purpose of the letter is to set up a follow-up call. You can gain more tips on the letter structure from this classic book by Anthony Parinello. In paragraph one go directly to the WIIFM – what’s in it for them – and move directly from value proposition to value creation. Lead with provocative insight, demonstrating without a doubt that you have done a thorough due diligence of their business issues.

4) The “I’m in the Neighborhood” Technique

Obtain a ticket to a key city within your territory. Email prospects saying that you’ll be in the area. Schedule a number of these per city. You can also leverage this technique to book meetings around a conference. This technique is most effective when scheduled one week out.

5) Conference Within The Conference

Reserve a meeting room in a classy hotel across the street from a major conference. Schedule a dozen appointments over a couple of days with key executives. You can leverage this to replace an entire quarter of on-sites. The executives are already there!

The other ingenious method is to get a free floor pass, diagram the entire multi-level conference floor blueprint out and then strategically approach every single relevant booth, moving past the greeters in front to the executives in the back. Goal yourself to collect 300 business cards, shake every hand and add them all on LinkedIn with a personalized invitation; keep a running log in Evernote. (Ideal strategy for Dreamforce and OpenWorld).

6) Head To Head Pilot

If you truly have the better solution, challenge the incumbent to a fulfillment duel. Commence bake-off: may the optimal solution that drives the greatest efficiency win! Make sure you agree upon fair success criteria and eliminate any inequities or handicaps. It must be an apples to apples comparison in your apple pie contest.

7) The Full Blown Referral

Bold move, but put their key decision makers directly in touch with your biggest client. YouTube video testimonials can be a fall-back. Believing is seeing!

8) The Reverse RFP

Build an RFP criteria document that realigns your strengths based on the selection criteria and question-set. Offer to provide prospects free consulting on the RFP process to ensure they are asking the right questions. Tip the scales in your favor.

9) “Your Baby Is Ugly”

Candidly level with them on what is broken by diagnosing their problems beforehand. Be honest about how dire the situation is. Nobody likes to admit their “baby is ugly” but in business, it’s refreshing and highly ‘Challenger Sale’ to respectfully call out the elephant in the room of a missed quarterly target, flawed network architecture, broken website or fatally flawed SFA.CRM implementation. Hint: read between the lines of the annual report.

10) Walk The Halls

With an existing account, literally take a desk in their office, post-up for a day and get to know everyone in the building. Walk the halls and hang out at the water cooler. Without exaggeration, I’ve seen this technique work selling into finance where relationship building is still crucial, especially in key account management.

11) Be Over-The-Top Remarkable

I saw a top sales executive out-dress everyone in flawless suits, ties, pocket squares and shoes you could see your reflection in. Peacock much? Well, that was his thing and he authentically owned it.

I saw another salesperson who was an expert at swing dancing who would clear the middle of the dance floor at company hosted client events. Another way to be remarkable is to recommend an idea that is fundamentally transformational to their business model. Push the envelope.

Be willing to leave bright shiny collateral behind, like a massive poster board with a Vizio diagram of your latest collaborative brainstorming session.

A colleague once sent a cake to a CEO to land a meeting with ‘we can help you eat more cake’ on it, had engaged the EA beforehand, it worked.

12) The Ensemble Close

Be the conductor of the symphony. Despite the size and stratification of this global firm, a top performer at a software automation company won huge deals by looping in almost every conceivable party in the selling organization, even the CEO and CTO. Much to the chagrin of lower performers, so many stakeholders on both sides were invested in the deal, it became a self-fulfilling prophecy it would close and the deal even grew mid-closing!

That guy always got the top performer award at every kickoff. (Not so coincidentally, he was also the aforementioned King of Swing!!)

13) Ghost Protocol

One of the people I am mentoring is achieving amazing sales results and in my view it’s because he has gained the trust of his own CEO to the point where he is leveraging the CEO’s LinkedIn account. This takes significant trust from the CEO but is a great example of achieving maximum support internally, as you then go into the marketplace at the highest possible level with an ‘insight’ and VITO-style of approach.

Another mentee unleashed a ghost army via a stealthy B2B lead gen startup that leverages an AI engine to effectively generate a dozen warm C-Level intros per week, skyrocketing fresh pipeline so sustainably, it’s temporarily supplanted the need for hiring an analog inside sales team to augment it!

Strategic selling is about engaging early at the most senior levels and some of these tips can help in that regard. But if you’re late to the dance, many of these ideas may spark ideas to execute before choosing to simply qualify-out.

Pipeliner CRM empowers any bold move for sales. Get your free trial of Pipeliner CRM now.

About Author

A bestselling author, award-winning blogger and the most read LinkedIn Author globally on the topic of B2B sales leadership. Tony’s first book is a business bestseller with his second book, COMBO Prospecting, available on Amazon here. He can be found at and

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