The Curious Case of Ambiguity in sales (and probably, life)

Vineet V. George
5 min readJan 23, 2024

Sales, as a profession, has taught me a lot about life, people and situational intelligence. I’ve had the opportunity of selling quite a few different ‘things’ from books to cloud services, from maps to marketing analytics tools.

Given some of the diversity of the products (and services) I’ve ‘sold’, I’ve had the opportunity of working with a variety of individuals over time — founders, leaders, product managers, growth hackers, procurement managers, finance gurus, influencers, champions, discontent customers, negative reviewers, angry executives and every now & then, an intern or two.

Across all these different types of roles, age groups and power dynamics, the core of the relationship remains the same — a seller pitching to a buyer.

Each of them is trying to capture higher value from the other. A clear win-win situation arises when the buyer and seller are happy (or better still, delighted) with the overall transaction.

‘Yes we negotiated well and got a great deal!’

The buyer-seller relationship is a very unique one and at the same time, it is a relationship hat we all don, throughout our lives — sometimes even multiple times in a day. We’re always selling (or buying), without even knowing it — Kids pitching to their parents for a toy, an employee pitching to their boss for an appraisal, or even lovers, pitching to each other at various stages of a relationship. We are all engaging in ‘sales’ all throughout our lives.

In the realm of business-focused sales, as one can imagine, different buying-selling situations exist. The situations would vary enormously depending on the industry, the economic environment, people involved, the stakes and the goals. There could be a multitude of different scenarios that we could think about but there is a simple way of dividing all these engagements into two distinct types of sales processes (especially in B2B sales) -



Now, what could this mean?

Well here’s the definition of ambiguity from the Oxford Dictionary —


‘The state of having more than one possible meaning’.

Consider a very simple case of negotiation in a B2B sales process and let’s take a look at two different types of sales scenarios. Here’s how they could play out:

Sales Scenario #1 (The dream deal cycle)

  • Seller shares a quote, buyer reviews, checks features and asks specific queries about the product + features. Seller gets back with answers to those queries.
  • Buyer then talks about pricing and asks for some reasonable discounts in an open way, speaking about budgets, timelines etc.
  • Seller comes back with possible discounting options and implementation scenarios.
  • Buyer confirms one of the options. Seller gets required approvals.
  • Deal is signed. They start working together.
  • Seller and the selling team are so happy with the attitude of the buyer that they go out of their way to support the buyer’s team.
  • The buyer is a great ‘client’ now.
  • The buyer is also happy with the engagement and goes about utilizing the product/service to achieve their goals.

Sales Scenario #2 (The ambiguous sales cycle)

  • Seller shares a quote, buyer says the price is too high. Seller asks for expectations. Buyer asks seller to send their best offer. Seller shares discounting possibilities and volumes.
  • Buyer then sends ridiculously low number. Seller informs buyer they cannot do that number but happy to help if buyer can share more around their use-case, budgeting process etc.
  • Buyer adamant to close at low price or they’ll go to their competitor. Seller apologizes and shares inability to go down further.
  • Buyer remains silent for a few weeks. Seller shares some good collateral that might be helpful for the buyer to make the decision. Another couple of weeks go by.
  • Seller has moved on but Buyer suddenly gets back, says it’s urgent now and they would be okay closing at slightly higher than the ridiculously low price quoted earlier. Seller has to refuse again.
  • Buyer asks for final quote from the seller. Seller sends the discounting scenarios again. Buyer finalizes one option, asking for a one time lower price (slightly more reasonable now). Tired seller gets required approvals for the final number.
  • Buyer finalizes, closes the deal. Seller is exhausted and can’t wait to move on to the next deal. Hands over the relationship to the support team asap. Buyer’s team does not receive the kind of engagement & support a happy seller would have provided.

More often than naught, most of us would want to work with Scenario #1 — It is quite obvious — Scenario #1 saves so much time, effort, resources and costs.

The sad reality is that many sales experiences are composed of Scenario #2. This scenarios plays out considerably more frequently than Scenario #1.

This is quite interesting because Scenario #1 feels like the right choice for everyone in the equation right — The buyer, the seller, the teams involved, the overall goals that need to be met and , in general, for humanity as a whole. (Okay I took things a bit too far)

So why does Scenario #2 become a reality in so many instances? What causes this? And how do we try and steer conversations to Scenario #1?

{P.S. In many cases, regulations, legal requirements, compliance and other auxiliary factors tend to cause delays in the sales process but for the purpose of this discussion we will limit the conversation to the actual ‘sales process’ — a buyer finalizing a product or service with a seller}.

The Why

Why does ambiguity exist? Well, in my experience, there are two main reasons why ambiguity exists -

  1. Trust or the lack of it
  2. Competence and Connection

Trust, in this case, is a two-way street. The customer may not trust the seller and vice versa. Most of the dynamics of sales cycles are built on this very core human value.

How do we build trust?

In most of the sales conversations I have had in the last decade or so, trust usually comes with vulnerability. Being vulnerable with others, being open to them about our pros as well as our cons helps build long lasting trust.

For instance, when we tell a prospective customer that these are the three things that we do very well but these three things are better served by our competitor, they usually appreciate the honesty, and in most cases also ask us how they can work around these challenges with our product or service.

Competence and Connection are the other two traits that have always helped great sales & consulting people stand out from the rest of the crowd. I learned about this from an amazing podcast by Matt Abrahams and Jacob Morgan (YouTube Link).

A competent sales & consulting rep knows their product/service exceptionally well and is able to dive deeper into the problem statement of the prospective customer better, connect use-cases to the product/service and in the end answer the very crucial value question of ‘Is this product/service going to help the customer achieve their goals?’

So what can we do as sellers?

Understand that we are selling to ‘people’. B2B, B2C, D2C, B2B2C — All sales scenarios are, at the core of it, a simple value-based conversation between two human beings. Two human beings with their own perceptions, perspectives, idealogies and unique thought process.

If we approach these conversations as we would approach our conversations with friends — with vulnerability, openness and trust, we’d most likely fare better than if we didn’t.

To be or not to be (ambiguous), that is the question.

Happy buying and selling!



Vineet V. George

A sales and consulting professional who enjoys writing about things that are close to his heart.