Put a person from 1835 in a room with someone from 2025 and they could talk effectively. Strip out the nouns, old or modern sounding place and product names, and the underlying language would be very similar. They would still communicate well.
Every deal behind every part of modern business would, at some stage, have involved a conversation between two key parties, usually a buyer and a seller.
And this is what all good sales comes down to.
Strip out the tools, the noise and the repetitive processes, and you still need two people on opposite sides of a situation to come together on the same side by exploring ideas and reaching some kind of consensus.
Yet, it can seem our whole profession, from sales leadership to front line salespeople, is doing all it can to stifle, automate and remove key conversational moments.
This is a huge mistake.
Despite what some studies would have you believe, B2B sales needs a lot of conversations to occur, ideally face to face, to ensure that deals are closed and desired customer outcomes are successfully delivered. To get to meaningful outcomes you need deep understanding, and this comes from a sales approach where conversation is prioritised.
So what behaviours can you encourage as a Sales Leader to avoid this trap, help your team stand out from increasingly vanilla competitors and make a difference to both your results and the buying experience you deliver? Here are 10 things as a starting point.
1. Remove Scripts
Have examples and processes if you need them, but sales is not pitching.
It is questioning, listening to the answer and going on the journey wherever the conversation takes you. Real conversations do not follow fixed patterns, so teams need to get comfortable with variety.
2. Role-play Scenarios
Set aside team time to practise customer-facing conversations and build the mental muscles needed to listen and respond to what is actually being said, rather than simply waiting for a turn to talk.
Look at body language, energy levels, and natural versus forced speech patterns, all of which can influence how a buyer feels.
3. Remove Jargon and Internal Product Language
Buyers do not know your internal world, and they usually do not want to.
They want help. Internal shorthand and product language can create distance instead of clarity.
4. Ditch Pre-prepared Decks
Try having conversations without supporting materials.
Focus on the person in front of you and send additional information afterwards.
This helps the interaction feel more human and less like a performance being delivered at someone.
5. Do Not Take the First Answer at Face Value
Especially if it tempts the seller to jump straight into a solution.
Go deeper.
Stay curious.
Ask more questions.
Explain, describe and imagine questions are often useful for helping buyers open up and feel more connected to the conversation.
6. Prioritise Talking as The Communication Method
If someone asks for an email, suggest a call.
If you are sending an instant message, consider a voice note or video message.
Spoken communication creates more human connection and gives the buyer a better sense of your tone, intent and presence.
7. Handle Important Moments in Real Conversation
Discovery sessions, presentations, negotiations and solution-building conversations are all stronger when handled in real time.
When possible, do them face to face.
These are the moments where familiarity, trust and shared understanding are built.
8. Remove Barriers in The Setting
The environment influences the quality of the conversation.
Sitting alongside someone can feel more collaborative than sitting opposite them across a large table.
A walk or a relaxed setting can often produce a better conversation than a formal meeting room.
9. Encourage The team to Listen More Than They Speak
Simple, but often ignored.
Better listening leads to better understanding, better questions and stronger buyer trust.
10. Measure Meaningful Conversations
Make meaningful conversations a more important measure than some of the other data points in the funnel.
If you increase the number of genuinely useful, trust-building conversations, pipeline quality and outcomes often improve with it.
Key Takeaways to Make Sales Conversations Count
– Great sales still depends on meaningful human conversation.
– Over-automation can remove the moments that build trust and understanding.
– Better sales conversations come from curiosity, listening and adaptability.
– Important buyer moments are often best handled in real-time conversation.
– Teams that improve conversation quality are better placed to improve trust, pipeline and results.
At The Humble Sale®, these are the very skills we train through our playbook-led approach: helping sales teams develop the confidence, curiosity and conversational quality that drive better outcomes.
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