How To Win Huge Deals When The Stakes Are Dangerously High [Checklist]

Tony Hughes


What exactly do you do?

Bond: 'Oh, I travel... a sort of licensed troubleshooter.'

We've all been there before. The Battle Royale or maybe we've bet it all on red 16 at the roulette table. We're under deep cover in Monte Carlo and it's time to jettison the casino before the scorpions find us in our beds. We may just feel like 007 - pick your favorite scene...It's life or death in strategic selling! The competition has its hooks in the deal. The prize looks too sexy to be true. Procurement is shaving us down like a Bond villain calmly stroking a Persian pussy cat whilst openly revealing a sinister plot to choose a commodity supplier for total margin domination.

The quarter is about to close and we're banking on this one key moment to make or break our chances of the commission check. It's New Year's... somewhere. The RFP response has gone out. The SOW is sent. It ain't cheap to put gas in this vintage Aston Martin or keep a tuxedo pressed under scuba gear 365. The shot clock is ticking. The client will invariably demand a 'friends and family' discount. Haven't we trained them to wait until the last minute? Truly...what do you do? How do you navigate the island of Dr. 'No' to still engineer winning the deal, saving the world and booking the revenue. What is the role of social when the stakes are extremely high?

Sales is simple, right? Well yes, you may not need the mathematician's mind of Ian Fleming but you will need to know how to take calculated risks. Bonus points for getting away with quippy one-liners! If you prepare incredibly well, anticipate competitive threats and risks and leave no stone unturned in your close planning process you just may have a shot at diamonds forever. You must maintain a rigorous focus and discipline as the best military strategist would. When I'm working a six, seven, eight and even nine figure deal, I remain constantly vigilant and many questions race through my mind, many of which I outline below for your Youtility belt. Confidence is the feeling you have just before you understand the situation. Don't let your ego blind you. Cockiness can get you iced by Odd Job. For many of us, earning a living in complex B2B sales is a roller coaster ride and 60's spy novel with a cliffhanger ending. I've been there... Use this checklist to live to die another day, keep your golden eye on the ball and emerge victoriously to make a lucrative sequel with Cubby Broccoli:

  • Are you proactive or reactive in this deal? Are you levering it forward with leading vs. lagging measures? Have you evaluated the execution aspect of your sales process? Are their leading indicators and pattern recognition from past Win and Loss Reviews that would indicate impending victory?
  • Did you anchor the deal? Budget, Timeline, Compelling Event, Success Criteria - Are you pre-radioactive in your decay rate?
  • Did you RSVP? Relationships, Strategy, Value Creation, Process
  • Did you thoroughly perform discovery before you presented? Was your presentation Jobsian under 10 slides? How many Ahas and Wows did you garner? Better yet, did you simply Venn diagram it out on a white board with a dry erase marker keeping eye contact and addressing all concerns?
  • Do you understand the political power base and situational power base Mr. Fox? Do you know who your frenemies are in the account before you dodge friendly fire? Who ultimately holds the P & L and is authorized to sign a Production Order?
  • Did you 'beestorm', meeting with various stakeholder groups to build consensus? Who is mobilizing the deal? Talkers, blockers vs. advocates?
  • Who is the incumbent supplier and which exact sales people are you up against? Are there rogue consultants circling who can tip you off as to your status as a third stringer to simply check the box on three required vendors in a bureaucratic government tender process?
  • Are you missing requirements? Is there FUD - fear, uncertainty and doubt - that you can utilize to your advantage? Did you highlight their weakness, set traps and lockouts and differentiate by demonstrating unexpected value?
  • What's the outcome VITO is looking for? What are the risks if they don't change from the status quo?
  • Did you ask Situation Problem but especially Need-Payoff questions to dive deep enough to the root cause of the problem(s)? [SPIN] Did you peel the onion? Honestly, are you addressing a symptom or the true problem?
  • Did you win the business sale as well as the technical sale? Did you produce a tailored insight-driven presentation and proposal to each group? Did it highlight the competitors' weakness and position you as the leader? Oh no... have you said to much. Oversharing requirements can inversely increase perceived risk!
  • Have you personally met with the signer off-site? Have you leveraged risk as a weapon?
  • Have you leveraged LinkedIn Sales Navigator to gain intel and TAS Dealmaker to politically map the account? Have you honestly qualified hard enough?
  • Based on RAIN Group research did you Connect, Convince and Collaborate effectively? [The 3Cs are why Winners win, 'based on 700 B2B purchases with buyers responsible for over $3.1B in annual purchasing and interviews with 150 corporate buyers about their recent purchasing experiences.']
  • What is your military strategy or battle plan? Did you plan and execute it? Land and expand, Direct, Flanking, Attrition, Containment, Guerrilla etc.
  • Did you deftly leverage social media at every phase of the funnel? #strategicsocialselling
  • Did you speak CXO? Did you respectfully challenge but make sure to build rapport and trust advisor status prior? Did you build a provocative business case? Did you ideate enough with first principles thinking? Did you deliver a commercial teaching pitch? Teach, Tailor & Take Control [CEB]
  • Do you understand the trigger event(s) in play? Is the trigger strong enough? Better yet, were you first in, pre-trigger? Was that trigger a change or transition opposed to awareness or bad supplier? Did you analyze previous wins to influence this one?
  • Does the most senior executive truly understand why you're different? Did you present a convincing value hypothesis? Did you build a conservative, believable ROI or lift calculator?
  • Have they called a raving reference client? Have you presented hyper-relevant case studies?
  • Have you ghostjacked your own CEO's profile to directly connect to their CEO or Board via social profiles? Have you flown out on-site with your own internal executive sponsor?
  • Have they talked 75% of the time? Have you shared a powerful sales story? Have you brainstormed and white boarded with them? Did you perform gap, white space or SWOT analysis?
  • Have you connected emotionally and cerebrally? Have you had coffee independently with each to understand the politics?
  • Have you embedded yourself into a burning business case? Will she get promoted by choosing your solution? Will you transform her business? Will you make the customer look like a hero?
  • Have you communicated why and how you will save or make the company millions? Do you understand the health of the company? Are they in growth, stasis or crisis mode? What does the annual report tell you? What are the clues from the balance sheet?
  • Have you built a Gantt chart for execution and delivery stages ratified by the client? Are you holding each other accountable?
  • Have you established a cogent close plan?
  • Have you bubbled this up to your internal executive team to make this deal a priority and leverage their networks to triangulate into the power base?
  • Are you leveraging all your resources including pre-sales engineers, solutions consultants and client services? Are you the conductor of the symphony?
  • Did you put your CTO, CIO, CFO in touch with theirs?
  • Do you have empirical evidence and proof the deal will actually close? Hope is not a strategy. Has legal cleared for the MSA or PSC? Have you moved the deal into the end zone 15 days before the quarter closed?
  • Have you been tenacious in your follow up always adding value but never violating the principle of non-hunger?
  • Is the customer buying IBM? No one ever got fired for choosing them thus they were always happy to pay more for job security. Did you build a strong enough business case that the risk not to change is far greater than the risk of maintaining the status quo? Did you reduce friction early in the sales process? Did you make it easy to buy from you?

Ask yourself these questions when considering your 007 strategy:

  • What is our relationship strategy and are we aligned with the power-base?
  • Do we truly understand the decision driv­ers and business case?
  • Do we understand their corporate mode and personal agendas?
  • Who and what is our competition and how will we position against them?
  • Does the customer have other projects competing for funding?
  • Which of our competitors is engaged with the customer?
  • How will our competitors seek to position against us?
  • What are our compara­tive strengths and weaknesses?
  • How will we engineer the customer's focus on our unique value?
  • How will we prove or validate our capabil­ity and lowest risk?
  • Where will we position price to leave room to negotiate?
  • Do we have all necessary information and what don't we know?

Here's a sensational true story and case study where I went up against an incumbent supplier and won against all odds. Read how we did it as you think about how all the above check points factored in...

Now it's your turn: What did I miss on the checklist? What do you ensure you've covered in order to increase propensity of winning major enterprise deals in the 11th hour? Managers... Are you out there? Care to open-source your clandestine thoughts on the comment thread faster than you can say 'espionage?'



Tony Hughes is ranked as the #1 influencer on professional selling in Asia-Pacific and is a keynote speaker and best selling author. This article was originally published in LinkedIn where you can also follow Tony's award winning blog. Also visit Tony's keynote speaker website at or his sales methodology website at

Main image photos by Flickr: Johan Oomen


Please Share: If you valued this article, please  share via your Twitter, LinkedIn, Google+ and Facebook social media platforms. We encourage you to join the conversation or ask questions. So feel free to add a comment on this post below.

Your Invitation: We invite you to subscribe to this blog. Subscription is free and it allows you to get access to all our subscriber only content and our periodic newsletter.



Are you searching for advice that will help you grow and manage sales - or lead your sales team? You are likely to find it here. This site brings you some of the latest expert thought leadership content on business to business (B2B) sales from the SMA Sales Masterminds.








SMA Masterminds
© 2018 All Rights Reserved.