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MassChallenge / Skolkovo Super League 
Connection-based selling 
Sep 9, 2014 
Rishi Dean | @rishidean
2 
Sales is the life of your company 
§ Raising outside investment only gives you the ability 
to play the game 
§ Selling is how you earn your living, and determines 
whether your company succeeds or fails 
§ Selling is different from sales management
3 
People buy from people
4 
We buy from people we trust 
§ We trust people with a common world view 
§ We trust people who listen and understand 
§ We trust people who want the best for us
5 
We decide emotionally, and then 
rationalize logically
6 
It’s biological, not cultural
7 
Must appeal to both the “elephant” & 
“rider” to make change
8 
Rational 
§ Price 
§ Quality 
§ Speed 
§ Features 
§ Reliability 
Emotional 
§ Aspiration 
§ Beauty 
§ Safety / Security 
§ Nostalgia 
§ Fairness 
§ Control 
§ Fame 
§ Fear of loss
9 
Make the buyer feel like a hero
10 
Connection-based selling 
1. You need give people a reason to care (cut through the noise) 
2. People need a reason to change (pleasure seeking / pain avoidance) 
3. Product is in the customer's mind (vision match) 
4. Emotional decisions with logical justifications (what's in it for me?) 
5. Can't sell to someone who can't buy
11 
Connection-based selling framework 
Personal 
§ Learn about the buyer as a person 
§ Figure out their underlying business issue 
§ Uncover the buyer’s pains & aspirations 
Valuable 
§ Connecting solution to business issue 
§ Quantifying the value proposition (rational) 
§ Making it meaningful for them personally (emotional) 
Credible 
§ Supporting your claims (e.g. references, benchmarks) 
§ Handling objections 
§ Make your buyer a champion to their stakeholders 
Clear 
§ Determine the decision-making landscape 
§ Develop a shared plan and definitive next steps 
Hook 
§ Start with the “WHY” to spark interest and gain the 
opportunity to sell
12 
hook 
Watch video 
1
13 
The Golden Circle 
Watch video
14 
personal 
2
15 
Understanding your buyer 
1. What is their role / responsibility in the organization? 
2. Who do they report to? 
3. What trying to achieve? How are they compensated?
Uncover the business issue (don’t assume) 
16 
1) Time to market 
§ Funding or resources too low 
§ Lack of expertise 
2) Cost management 
§ Redundant or manual processes 
§ Not understanding variable cost contributors 
3) Reliability & Quality 
§ Excessive complexity 
§ Lack of testing
Ask questions to uncover the business issue 
17 
Open 
§ Shows the client you're 
interested 
§ Helps you understand 
their perspective 
§ "Can you tell me 
about...", "Why is...", 
"Tell me more...” 
Probe 
§ Shows you have a 
good understanding of 
the problem 
§ Uncover more specific 
needs 
Confirm 
§ Shows you understand 
their paradigm 
§ Playback / confirm
18 
valuable 
3
Connecting your solution to buyers’ issues 
19 
1. Ask "WHY" to elevate the discussion of business issues and any 
unrecognized problems 
2. Probe to steer toward problems you can uniquely solve and 
3. Frame the solution around their point of view 
4. Quantify the value proposition / outcome 
5. Make it personally rewarding for the buyer to solve this problem
20 
Ask questions to determine value 
Open 
§ What is it worth to 
you? 
§ How would you 
measure the payoff? 
§ What will having this 
do for you? 
§ How does this impact 
you personally? 
Probe 
§ Have you considered 
how this relates to cost 
management or 
revenue? 
§ Can you give me an 
idea of how big this 
issue is? 
Confirm 
§ Is this enough for you 
to buy?
21 
credible 
4
22 
Remove uncertainties with external support 
1) How will you support your claims? 
§ Case studies & customer references 
§ Benchmarks 
§ Awards, media, PR 
§ Relationships, “halo effect”, (investors, advisors, academics) 
2) Overcome key risks and objections 
3) Make your buyer a champion to their stakeholders
23 
clear 
5
24 
Assess both sides of the power balance 
§ Power in the buyer to make a decision 
§ Power in the sales person to allocate resources and 
time to an opportunity
25 
Mapping the decision making landscape 
§ Who else is involved in this decision? 
§ Who else is impacted by this decision? 
§ Once this decision is made, who signs the 
paperwork? 
§ Who can veto this decision? 
§ If you had to get more funding, who would 
you go to? 
user 
influencer 
buyer
26 
Develop a mutual plan for next steps 
§ Ask for access to decision makers 
§ Develop a “reverse timeline” working backward from 
success 
§ Work together to fill in missing steps 
§ Avoid scope creep by asking for something in return
27 
Other factors for successful outcomes 
§ Respect time and deadlines 
§ Show empathy 
§ Know their business 
§ Shared understanding 
§ Deliver on what you promise
28 
Hook 
§ What is your “WHY” | “HOW” | “WHAT” 
2 
3 
Personal 
§ List 3 things you know about the prospect 
§ What are their roles / responsibilities 
§ What are they struggling with 
§ What do they personally want to achieve 
Valuable 
§ How does your solution connect to their 
business issue 
§ What is it worth to them / How does this 
impact their business 
§ How would you measure the payoff 
§ What does it mean for them personally 
45 
Credible 
§ What support (e.g. customer references, 
benchmarks) can you use to support your 
claims 
§ How may the prospect use this to be a 
champion for you 
Clear 
§ Who are the other decision makers 
§ Who are the other stakeholders in this 
decision, who are the users, who can veto 
§ What is your mutual plan and next steps 
1 
Connection-based selling cheat sheet

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Connection-based Selling (MassChallenge / Skolkovo)

  • 1. 1 MassChallenge / Skolkovo Super League Connection-based selling Sep 9, 2014 Rishi Dean | @rishidean
  • 2. 2 Sales is the life of your company § Raising outside investment only gives you the ability to play the game § Selling is how you earn your living, and determines whether your company succeeds or fails § Selling is different from sales management
  • 3. 3 People buy from people
  • 4. 4 We buy from people we trust § We trust people with a common world view § We trust people who listen and understand § We trust people who want the best for us
  • 5. 5 We decide emotionally, and then rationalize logically
  • 6. 6 It’s biological, not cultural
  • 7. 7 Must appeal to both the “elephant” & “rider” to make change
  • 8. 8 Rational § Price § Quality § Speed § Features § Reliability Emotional § Aspiration § Beauty § Safety / Security § Nostalgia § Fairness § Control § Fame § Fear of loss
  • 9. 9 Make the buyer feel like a hero
  • 10. 10 Connection-based selling 1. You need give people a reason to care (cut through the noise) 2. People need a reason to change (pleasure seeking / pain avoidance) 3. Product is in the customer's mind (vision match) 4. Emotional decisions with logical justifications (what's in it for me?) 5. Can't sell to someone who can't buy
  • 11. 11 Connection-based selling framework Personal § Learn about the buyer as a person § Figure out their underlying business issue § Uncover the buyer’s pains & aspirations Valuable § Connecting solution to business issue § Quantifying the value proposition (rational) § Making it meaningful for them personally (emotional) Credible § Supporting your claims (e.g. references, benchmarks) § Handling objections § Make your buyer a champion to their stakeholders Clear § Determine the decision-making landscape § Develop a shared plan and definitive next steps Hook § Start with the “WHY” to spark interest and gain the opportunity to sell
  • 12. 12 hook Watch video 1
  • 13. 13 The Golden Circle Watch video
  • 15. 15 Understanding your buyer 1. What is their role / responsibility in the organization? 2. Who do they report to? 3. What trying to achieve? How are they compensated?
  • 16. Uncover the business issue (don’t assume) 16 1) Time to market § Funding or resources too low § Lack of expertise 2) Cost management § Redundant or manual processes § Not understanding variable cost contributors 3) Reliability & Quality § Excessive complexity § Lack of testing
  • 17. Ask questions to uncover the business issue 17 Open § Shows the client you're interested § Helps you understand their perspective § "Can you tell me about...", "Why is...", "Tell me more...” Probe § Shows you have a good understanding of the problem § Uncover more specific needs Confirm § Shows you understand their paradigm § Playback / confirm
  • 19. Connecting your solution to buyers’ issues 19 1. Ask "WHY" to elevate the discussion of business issues and any unrecognized problems 2. Probe to steer toward problems you can uniquely solve and 3. Frame the solution around their point of view 4. Quantify the value proposition / outcome 5. Make it personally rewarding for the buyer to solve this problem
  • 20. 20 Ask questions to determine value Open § What is it worth to you? § How would you measure the payoff? § What will having this do for you? § How does this impact you personally? Probe § Have you considered how this relates to cost management or revenue? § Can you give me an idea of how big this issue is? Confirm § Is this enough for you to buy?
  • 22. 22 Remove uncertainties with external support 1) How will you support your claims? § Case studies & customer references § Benchmarks § Awards, media, PR § Relationships, “halo effect”, (investors, advisors, academics) 2) Overcome key risks and objections 3) Make your buyer a champion to their stakeholders
  • 24. 24 Assess both sides of the power balance § Power in the buyer to make a decision § Power in the sales person to allocate resources and time to an opportunity
  • 25. 25 Mapping the decision making landscape § Who else is involved in this decision? § Who else is impacted by this decision? § Once this decision is made, who signs the paperwork? § Who can veto this decision? § If you had to get more funding, who would you go to? user influencer buyer
  • 26. 26 Develop a mutual plan for next steps § Ask for access to decision makers § Develop a “reverse timeline” working backward from success § Work together to fill in missing steps § Avoid scope creep by asking for something in return
  • 27. 27 Other factors for successful outcomes § Respect time and deadlines § Show empathy § Know their business § Shared understanding § Deliver on what you promise
  • 28. 28 Hook § What is your “WHY” | “HOW” | “WHAT” 2 3 Personal § List 3 things you know about the prospect § What are their roles / responsibilities § What are they struggling with § What do they personally want to achieve Valuable § How does your solution connect to their business issue § What is it worth to them / How does this impact their business § How would you measure the payoff § What does it mean for them personally 45 Credible § What support (e.g. customer references, benchmarks) can you use to support your claims § How may the prospect use this to be a champion for you Clear § Who are the other decision makers § Who are the other stakeholders in this decision, who are the users, who can veto § What is your mutual plan and next steps 1 Connection-based selling cheat sheet