
“I’d really love to spend more time coaching, but…”
When have you heard this before?
If you are anything like half the sales managers we talk to, you've probably heard of this today. In fact, the thought has most likely been rattling around in your brain for a while.
You are not alone.Â
“For the last five years, sales coaching has had the greatest impact on win rates and quota attainment. However, less than half of the study participants leverage sales coaching effectively.” - CSO Insights‍
Yikes.
Yikes, because sales coaching, and I mean structured, regular sales call coaching has been proven to DOUBLE conversion rates.
Now isn't that leaving money on the table?
Counterpoint, can you blame sales managers, though? Companies rarely, if ever, have KPIs for sales call coaching. In fact, according to the CSO Insights study above, nearly 63% of organizations "follow a random or informal approach” to call coaching.Â
If sales is the lifeblood of an organization, inconsistent call coaching is like building a circulatory system out of paper straws and glue and hoping it all holds together.
What is sales call coaching?
To put it simply, sales call coaching is empowering your reps with the knowledge and skills they need to achieve success on their calls.
However, this is one of those cases where the “what” is less important than the “how”. Specifically, how do managers help their reps, especially when it is highly likely that there are no structured coaching processes in place?
In fact, even when people are committed to the cause, even when they have invested in the tools, they find it difficult to invest the time.

So here is a 5-step plan you can implement RIGHT NOW to begin to fix your sales call coaching woes.
How can you get started with sales call coaching?
Step 1: Get a culture in place.
Even the best tools and methodologies fall flat if there is no culture to support their implementation. Before you do anything else, ask yourself - What kind of coaching works best for your organization? Is it…
- Manager led, where the manager provides the feedback?
- Peer led, where peer reviews reign supreme?
- A mix of the two?
A manager-led approach is more structured while a peer-based approach is more likely to lead to discussion and openness. Sometimes it’s best to start with a certain approach and move towards another. How you get the culture in place is up to your team. What’s critical is that it happens.
Step 2: Stop call shadowing. Like, yesterday.
Ahh, call shadowing. The age-old method of sales call coaching, where the rep is either too stiff and scared to act naturally because they know the manager is listening in, or likely to defer to the senior at the slightest problem because there’s always a safety net.
Point is, call shadowing doesn’t work. Which is why it is so important to record calls and review them later. This is where software like Wingman come in handy — instead of spending 45 minutes reviewing a 30-minute call, you can streamline the review process and optimize the time spent.
Step 3: Walk a mile in the buyer’s shoes.
Imagine a cook who has never tasted food. An architect who never walked into a building. A tailor who… you know, you get the idea.
Fact is, reps rarely, if ever, get to be on the other side of the table. And yet, it is an invaluable experience — to be in the buyer's shoes and to be able to see what the seller is doing right or wrong.Â
As a manager, try to create as many opportunities as possible for your reps to be the buyer. Looking for a new tool? A new service? Have them join the pitch meetings. Later, ask them to review the performance of the sales person at the other end. Your reps are more likely to be honest and open when they are the buyer, and more likely to remember the lessons learnt as well.
Step 4: Insist on an agenda.
Thirty percent.
That’s how much higher the win rates are when the meetings have an agenda.
And yet, sales reps avoid agendas, feeling that agendas cramp their style, or make them sound artificial.
However, what sales reps miss is that setting an agenda right at the beginning of the call sends a signal that the rep is respectful of the buyer’s time. By setting a stage and a clear goal for the meeting, they instantly grab more attention from the prospect and subtly nudge them towards actively participating in the discussion.
Step 5: Believe in your reps.
Yes, we’re being a little Disney on this one, but it’s incredibly important to believe that your reps have both the ability and the motivation to succeed.
None of the points outlined above have any meaning if you don’t believe in your reps. Sure, you may need to nudge them along the way by asking them the right questions and providing a tip or two, but ultimately, you gotta have faith in them.
Don’t try to wing it.
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Now that you have the playbook, make sure you have your team and tools on your side. Ultimately, you need the right wingman so you can execute your coaching plans to perfection. To supercharge your sales call coaching, book a demo here.