This article is part of our Outreach on Outreach content series, in which we showcase our own revenue team’s use of the Outreach Sales Engagement Platform to help you drive success at your own company. We share workflows and strategies, backed by original research and data from the results of our own experiments and customer base.
Most sales coaching is a waste of time.
I’m sorry, but it is.
Sales managers pick topics at random and jump between reps without much thought or planning.
But I’m not blaming managers.
The problem is that old-school sales coaching is designed to fail.
Consider this: My SDRs make an average of 50 touches per day. With 14 reps in my team, that’s 3,500 touches per week.
I can manually review 5% of those conversations — 10% if I’m lucky.
It’s impossible to provide great coaching for reps when you see such a small portion of their work. Old school coaching feels like working in the dark.
What I needed was a way to analyze 80, 90, or 100% of my reps’ conversations — and I found it in Buyer Sentiment Analysis. Using artificial intelligence (AI), our sales engagement platform can review every single meaningful conversation a rep has.
The AI analyzes each conversation and categorizes the prospect’s response as:
Positive response: This is the magical reply that goes something like, “Funny you should email me because I was just thinking there has to be a better solution than what I’m doing today. When can we meet?” Everything you do should be optimizing for this reaction.
Unsubscribe request: Your prospect doesn’t want to hear from you. You’re completely out of the running here. You legally cannot continue to cold email this prospect, or you will be out of compliance with CAN-SPAM laws.
Objection: Your prospect replied to your email only to let you know that they don’t have budget. Ideal? No. With the right strategy, can you turn this into a deeper conversation? You bet.
With Buyer Sentiment Analysis, I’m no longer reviewing 5% and hoping they're beneficial. Instead, I’m analyzing them all and focusing coaching conversations around where I can make the most difference: objection handling.
If you want to know how to turn your salespeople into sales champions…
Sentiment analyzes every conversation and categorizes the prospect’s response into one of three buckets. But it doesn’t stop there. If it labels a prospect’s response as an objection, the AI digs deeper, unpacking their objection.
At the moment, we flag five different objections:
Prospect already has a solution
Not right person
For a sales leader, these insights are money.
Recently, I noticed that Katie, one of our SDRs, was receiving a lot of bad-timing objections. Around 15% of her responses were bad-timing objections, compared to a team average of 7.8%.
That told me something was wrong with her approach.
I dug into her conversations and discovered she was mishandling the objection. Instead of doubling down on urgency, she was kicking the can down the road.
Over three months, we refined her skills and improved her bad timing objection rate to 5.9%!
Without sentiment, I might have stumbled on that coaching opportunity. But if I were reviewing just 5% of her conversations, I’d probably have missed it. That’s the harsh reality of old school sales coaching.
At Outreach, we’ve had access to sentiment data for six months. It’s been transformative. It’s provided a brand new perspective for sales leaders. We can identify new insights, uncover fresh opportunities, and work out how to best support our reps.
Here’s how I’m turning those insights into coachable moments.
Unless you’re offering a brand new invention, you’re going to hit this objection — a lot. It covers everything from prospects who have a competing service in place to buyers already deep in their procurement process.
Whatever the specifics, this objection is a very good thing. If someone is already paying your competitor, they’re bought in on your value prop. All you need to do is nudge them from your competitor’s product to yours.
We coach two ways to do that.
If a prospect comes back with a specific competing product, we have pre-prepared battle cards detailing our key differentiators.
To prep SDRs, we roleplay conversations. I play the prospect who’s using our competitor and my rep tries to sell me on the Outreach’s differentiators.
The second coaching opportunity is for generic pushbacks. In these cases, our prospects have a solution in place but won’t tell our SDR which one.
If reps are getting this objection, it usually comes down to how they’re articulating Outreach’s value proposition or that they’ve misunderstood the prospect’s pain points. I’ll encourage them to double down on discovery and build out more personalized responses.
Bad-timing objections spiked in the early months of the pandemic. Even a year down the road, it’s still one of the most common objections we’re seeing. Companies are still flying holding patterns and their budgets are still thawing out.
A bad-timing objection feels like a deal in limbo. But it’s not.
If one of my SDRs gets a response, we know there’s a heartbeat. They just responded, so we know they’re thinking about us. Our SDRs have to work out how to bounce back from that.
The key to overcoming bad-timing objections is urgency. If a prospect tells one of my SDRs that it’s not the right time, they’re admitting there’s a need for our product, but it’s not urgent enough to act on right now.
If an SDR like Katie sees a spike in bad-timing objections, I’ll dig down into what they’re doing to create — or not create — immediate urgency. Are they bringing in background research? Are they pushing personalization? Are they tying everything back to the value of Outreach?
I encourage our reps to be persistent. If prospects acknowledge the need for our product, there’s a deal there. On average, it takes three touches and two weeks after a bad-timing objection to reach a positive response.
This objection is a catch-all for whenever a prospect refers us to one of their colleagues. Say, a VP of Sales sends my SDR to their sales manager. Or a sales enablement manager forwards a cold email to their director.
We coach for three specific responses to the objections.
If a persona refers us down the chain, our messaging is off. Usually, when our SDRs hit this objection, their pitch is too tactical. They need to get above the line and speak less about features and more about percentages or dollars.
If someone refers us up the chain, that’s about as good as it gets. We’re suddenly speaking to someone with more authority and more buying power.
But we encourage our reps not to take the intro as a given.
We teach them to stay on their current contact until their next conversation is underway. We’ll also encourage them not to wait for an introduction. Instead of waiting for an intro email, they’ll start multithreading immediately.
And if someone refers us to a different department, there’s clearly something wrong in our messaging or value prop. If a prospect bounces one of my SDRs from marketing to sales or sales to operations, we’re clearly not telling the right story. We’ll revisit their target persona and review their pain points. Then we’ll compare that information to the SDR’s messaging. Usually, there’s some misalignment there.
No one has a budget, right? Not until you drop your pricing, at least.
We coach two strategies to defuse budget objections.
First, we get buyers to name their price. If a prospect says, "I don't have the budget for this," we encourage our reps to push them for a figure. Reps can ask something simple like, "Well, how much would you pay for it?”
Getting a prospect to provide a ballpark figure doesn't mean we’ll achieve that price, but that's just a way of getting them to justify the outlay in their head.
The second strategy we coach is pushing past the objection to align on pain. Our reps will say, "I totally understand. The purpose of this call is actually just to see if we can align on the value and then we can take it from there."
Nobody is going to pay hundreds or thousands of dollars a month for something they don’t understand. Instead of wasting time dancing around dollars, our reps will ignore budget entirely until they’ve demonstrated Outreach’s value.
As with bad-timing objections, persistence closes deals. If our reps roll over, the lead is dead. But if they keep pushing, they're able to chase it back down.
Sentiment is a powerful coaching tool — but its impact doesn’t stop at individual reps. Recently, I was working with one of my enterprise SDRs in the UK. He was experiencing significantly higher objections than his North American counterparts.
We worked out that it wasn’t his individual performance that was letting him down but the templates, plays, and sequences we gave him.
Now, we’re building out sequences specifically for the European enterprise accounts.
We’re shrinking the word count, cutting the color, and getting straight to the point.
Sentiment isn’t just helping to improve our coaching. It’s enhancing our underlying sales motion, too.
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Stay tuned for our next Outreach on Outreach in a couple of weeks.