The members of your sales team watch you intently!
They observe your approach in 1:1s, team meetings, pipeline reviews, Teams and CRM comments. From all of that, they pick up what to prioritise. They learn your view of what “good” looks like.
It’s often not so much what you say that matters as much as how you choose to communicate and what they see you do.
In those everyday moments, they’re picking up one message: “These should be the priorities and behaviours of members of this team when we engage with customers.”
If you want your team members to use coaching skills with their customers, they must experience that kind of conversation with you.
And, of course, it must be consistent.
The pattern they copy
Too many salespeople experience:
Team meetings where the sales team leader talks for 20 minutes, and they’re expected to listen
1:1s that focus on dates, value and “when will it close?”
Teams/Slack replies that are instructions: “Send X”, “Book a demo”, “Update CRM”
CRM comments that are all about the sales stage and forecast numbers
These team members will copy that pattern with customers:
They’ll talk more than they listen
They’ll focus on process and timing, not outcomes and stakeholders
They’ll default to explaining and persuading instead of exploring implications
Nobody is being lazy. They’re following the signals you send every day.
To embed better coaching skills, they must experience conversations with you in which you lean hard into your coaching skills.
Why is this MUCH harder than it sounds?
There are solid reasons this feels uncomfortable.
You were probably promoted for having answers and hitting numbers. Senior leadership want forecasts and predictability. Reps want clarity, decisions and fast direction.
Directing is much faster and more controllable than requiring someone to think things through thoroughly.
Almost every external influence pushes the old pattern. LinkedIn, YouTube and most sales books still celebrate pitches, persuasive stories and “overcoming objections”. Very few show what it looks like to dig deeper with follow-on questions on carefully selected essential points.
And in a remote world, it feels efficient to fire off short instructions via Teams, Slack, or a CRM. Taking a moment to ask one or two good questions can feel like a delay you can’t afford, especially when you’re tired, stressed and preparing the Board Pack.
So if this feels awkward at first, that’s normal. You’re swimming against the current. That’s also why it matters.
Use every interaction as practice, not just formal coaching
You don’t need a new programme. You need lots of small shifts in how you already communicate.
In 1:1s, when a rep brings a deal or problem, try questions first, then advice:
“What do you think really matters most to them and their colleagues here?”
“Where did you decide to dig deeper in the last conversation?”
“If the next call goes really well, what would you want them to be saying by the end?”
In team meetings, move from broadcast to facilitation:
Start with: “What are the best conversations about outcomes this week where your follow-on questions changed the entire direction?”
When someone shares, stay with it
“What did you choose to explore in more depth?”
“Who else came into view once you asked who might be affected?”
You’re showing the whole group what it sounds like to explore implications and involve stakeholders, without turning it into a lecture.
In Teams / Slack / Email, you can often add questions before the instruction they’re seeking:
“What have you already heard from them about what success would look like?”
“Who else on their side might feel the impact if this works?”
“What’s the next question you could ask to dig deeper on that point?”
In CRM comments, you can pull attention back to outcomes:
“What outcome have they actually said they want, in their words?”
“Which stakeholders have you identified so far?”
You still give clear direction. You’re just making it normal that thinking about outcomes, implications and stakeholders comes first.
A simple way to raise the bar in 1:1s
Within this broader shift, you can use 1:1s as a deliberate practice ground. Not necessarily every time, and not with a big build-up. Just often enough that people start to expect it.
Pick a real opportunity and say something like:
“Let’s look at one recent conversation. Where did you decide what to explore in more depth?”
If they jump straight to stages and next steps, bring them back:
“I’m interested in the moment when you chose what to dig deeper into. What did you pick, and what were your next few questions?”
You’re not testing their memory. You’re helping them notice how they chose their second, third and fourth questions on the most important themes. Over time, that becomes a regular part of how you talk about deals: not just “what happened?”, but “where did you decide to dig deeper, and what did that change?”.
If you have AI summaries or transcripts, you can use them to find a short clip and replay a key moment together. The point isn’t to catch people out. It’s to make exploring implications a visible, discussable skill rather than a vague idea.
What starts to change when you stick with it
If you keep nudging conversations this way, you’ll start to notice some significant shifts.
Reps will bring you better questions, probably with solutions already prepared for discussion, not just problems to fix.
Deal updates will include clearer outcomes and more stakeholders, not just later-stage optimism.
Team members will learn to pause before saying “they’ve gone quiet” and instead ask “where did we stop digging deeper?” or “who else have we not brought into this yet?”.
You’re still accountable for achieving your team’s quota. That doesn’t change.
What can change is this: every time you engage with your team, in person, online or in writing, you’re either rehearsing the old “talk and persuade” script, or you’re modelling the kind of thinking and questioning you need them to use with customers.
Over weeks and months, that difference compounds.
Use this communication style and coaching approach consistently, and you’ll end up with a team that uses excellent coaching skills with customers, because they’ve learnt them by copying you!
