Wise Advice for Experienced Salespeople!
By Leenna Jayachaandran of Transdefy and Michael J Griffin of ELAvate
6 minute read
Thirty plus years in B2B Sales and sales coaching has given both of us a wealth of experience building win – win relationships with customers whether it be hunting new accounts or farming existing ones. But it has also taught us to be careful with our experience that can lead to wrong assumptions or snap judgments resulting in lost sales.
Leenna says, “There was a time when walking into a customer meeting with years of experience behind me gave me confidence that this meeting will lead to move the sale forward. My confidence was supported by experience.”
Had seen similar situations.
Heard similar objections.
Negotiated similar deals.
Met similar personalities.
And naturally, I begin to think:
“I know where this conversation is going.”
Today, Leenna far more careful with these thoughts.
Because experience gives us something incredibly valuable: pattern recognition.
But it can also quietly give us something dangerous: premature certainty.
We stop asking because we think we know.
We finish the customer's sentence in our head.
We hear “price” and assume budget.
We hear “let me think about it” and assume hesitation.
We meet a familiar personality and assume familiar behaviour.
And sometimes, the more experienced we become, the better we become at defending those assumptions.
One thing Leenna has learned over the years is “Experience should make us more curious, not more certain. Today, I probably walk into important conversations with more questions than I did 20 years ago. Not because I know less. Perhaps because experience has taught me how much I could still be wrong about.”
Has your experience ever made you rethink something you were once absolutely certain about?
Michael gives a resounding “YES” answer to Leenna’s question! Recently, he lost a large deal because he banked on some of the assumptions Leenna mentioned above. He very painfully learned that there was more information he needed to uncover about the customer’s internal relationships, personal motivators, and new processes in an account he has been serving for over 7 years. Michael also learned about how is own attitudes and motivators (based on his experience) blinded him to optimistically assuming the deal would close.
This experience led Michael to write a leadership blog last week on “Curiosity Culture” and how being continually curious is a must even when you believe your wealth of sales experience, pattern recognition and “wisdom” will carry the sale to the close. John Maxwell this week captures being curious in sales by his simple quote:
Don't be a know-it-all.
Be a learn-it-all.
Curiosity Is Your Sharpest B2B Selling Skill
Experienced B2B salespeople aren't the smoothest talker/experts — they're the best askers. Behavioral research keeps landing on the same finding: buyers trust salespeople who ask respectful, genuine questions far more than those who arrive with all the answers. Curiosity, not confidence, closes deals.
Don’t treat discovery or probing as a formality. Have the attitude of being a “curious servant leader” no matter how experienced you are. Experienced salespeople remain ever curious with the vision to exceed client expectations, never assuming they have the full picture. They ask "what am I missing?" and they listen to understand. Wisdom with humble patience is what surfaces the real problems, issues or needs that the client has not yet mentioned.
Curiosity Wins Deals and Prevents Losing Them
Curiosity slows down premature judgments, which keeps you from projecting your own “wise” assumptions onto a buyer's situation. It also builds deal safety: when a buyer feels genuinely heard rather than you sprouting your experience, they share the budget constraints, internal politics, and real timelines that usually stay hidden until late in the cycle, if they surface at all. Salespeople that sell this way consistently report shorter cycles and more long-term customer loyalty, simply because they're building proposals on real information instead of guesses or assumptions.
The Six Habits of Curious B2B Salespeople – No Matter What is Your Experience
Be Curious with a Desire to Exceed Client Expectations
Salespeople who truly want to serve customers by exceeding expectations are a competitive advantage. They strive for win-win by “seek first to understand then be understood.”
Comfortable and Secure to Say "I don't know."
Confident, secure salespeople ask when they're unsure instead of assuming or guessing or showing off your expertise.
Ask "Why" Before Pitching.
Probe & understand the “need behind the need” behind a customer problem or need before proposing a solution. Don’t a be a feature push expert!
Listen to Understand, not to Respond.
Resist rehearsing your next line while the buyer is still talking. Be curious and humble enough knowing there is always more to know – if you listen.
Be Patient with Ambiguity.
An unclear buying process, fuzzy situations, or a surprising change aren’t reasons to force a close — it's a reason to ask more questions.
Treat Objections or Concerns as Valuable Information.
A pushback is valuable information about what the buyer actually cares about, not an obstacle to overcome. Our research shows salespeople who are curious about what and why of objections are better at creating collaboration with customers to overcome the objections.
Cultivating the Curious Habit
You don't need a personality overhaul — curiosity is a trainable habit. Build all sales calls around open questions instead of a feature checklist or your past assumptions. Selling well was never about having every answer ready. It's about asking the questions that get you to the real problem or need — and the salespeople who make curiosity a consistent communication habit are the ones buyers trust enough to buy from and keep you the experienced salesperson from making expensive mistakes.
Michael J Griffin
CEO & Founder of ELAvate
Maxwell Leadership Founding Member
Global Sales Productivity Coach
Salesably AI Partner
michael.griffin@elavateglobal.com
+65 – 91194008 (WhatsApp)