Politely Pushy
How great sellers guide with confidence, care - and a bit of pressure to successfully earn trust, and close more deals
Hey everyone -
Back at it this week with an analogy I’ve used over the years to help sellers make sense of their role in the sales process.
When you're selling something complex, especially to enterprise buyers - the analogies are abundant, but also helpful to simplify and reframe what’s really happening in the buying journey.
Here are a few I’ve heard over the years:
The Sherpa Analogy: You're not the hero; you're the guide. Your job is to help the customer scale their own Mount Everest.
The Doctor Analogy: You’re not just asking about symptoms. You’re diagnosing, prescribing, and giving expert guidance even when it’s uncomfortable. You’ve earned that wisdom.
The GPS Analogy: Buyers may know their destination, but you're the system that reroutes them when they take a wrong turn or get stuck in traffic.
Each of these is useful, but one I’ve used with my teams over the years is this:
The Politely Pushy Tour Guide
If you’ve ever traveled to a foreign city, or key destination without a guide, you’ve likely had a good time, but missed a few things. You might hit the highlights, grab a pastry, wander into a museum.
Thinking about some cool places I’ve traveled like Costa Rica, Dominican Republic, Hong Kong, Tulum, this holds true. If you want to experience the full value of that city, and its hidden gems, peak experiences, and cultural nuance, a good tour guide changes everything.
And not just any guide…
I’m talking about the kind who’s polite, but kinda pushy:
“We need to leave in 5 minutes if we want to catch the last cable car.” or….“Trust me, this café doesn’t look like much - but it’s a local favorite.” or… “I know you’re tired, but you’ll regret skipping this view.”
The best enterprise sellers operate the same way.
They don’t just hit the bullets on the list of things to do - they direct.
They anticipate obstacles, keep things moving, and help buyers get more value than they would on their own.
Here’s what that looks like in practice:
Guiding the Process
Most buyers haven’t bought your product before. Even if they’ve bought something similar, they don’t know your exact process, your stakeholders, your landmines. You do.
That makes you the expert. Own it.
Spotting What’s Ahead
Whether it’s legal, procurement, or executive buy-in, great reps don’t wait for trouble - they navigate based on what “may” come up…
They identify bottlenecks early and help buyers plan around them.
Driving Toward Real ROI
Buyers often don’t know the full potential of what they’re buying. A good tour guide shows them what’s possible, and not just what they asked for, but potential risks, loss of revenue, and missed opportunities of “inaction” or “indecision”.
This means pushing where needed to explore value levers the buyer hasn’t considered just yet.
Balancing Authority with Empathy
Being pushy isn’t about pressure, it’s about understanding your role in the process, being present, and picking up on subtle cues to “slow down” or “speed through” any calm/rough waters.
The best sellers have confidence in their role as a guide, but also emotional intelligence in how they show up.
Now…does this style actually work?
Absolutely. Here’s why:
A recent Gartner study found that buyers are 147% more likely to purchase when they receive information that helps them advance their journey with confidence and clarity.
As I wrote about previously on The Challenger Sale: sellers who teach, tailor, and take control consistently outperform others - especially in complex, multi-threaded deals.
…
In fact, I saw this in action with one of my own reps.
Let’s call him Bradley. He worked a particularly long and complex opportunity with a Fortune 100 company over 18 months from first call to closed-won.
Twice during the process, we lost our internal champion. Each time, my rep had to rebuild trust, re-educate the new stakeholder, and resell the value proposition from scratch.
But what stood out wasn’t just his persistence, it was how he embodied the Challenger mindset.
When the second new champion wanted to pause and “reevaluate options,” or even slowly whittle away at the deal, my rep didn’t just nod along. He leaned in.
He taught them what other successful companies utilizing our product were doing and solving the very same problems they were having. He tailored the solution to their emerging needs. And most importantly, he took control - making it clear that waiting would cost them far more than acting decisively. And that “inaction” was actually costing them more than moving forward.
He reframed the conversation - not with pressure, but with insight, and emotional maturity.
Politely Pushy.
Won Deal.
STRETCH SNIPPETS
Matt Dixon with “The Challenger Sale: Taking Control of the Customer Conversation” explores how Challengers don’t shy away from tension: 80% of business is lost to no decision. Only reps who press politely and assertively win complex deals
Challenger Inc. describes the Challenger Sales Methodology. This deep dive highlights the three core skills: Teach, Tailor, Take Control, and emphasizes that Challenger sellers are comfortable with constructive tension and pushing tough conversations around commitments, pricing, and next steps
Again - I wrote a bit about this a few years ago. Stretch VP: Learning the fundamentals of The Challenger Sale and The Challenger Customer to win more deals.
🧠 Mindset
Thanks for reading!
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— Grant 👋
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Compiled and aggregated from a network of sales leaders in SaaS, Stretch VP showcases learnings, insights, and experiences as well as best practices to overcome common hurdles, obstacles, and setbacks in your quest for excellence as a sales leader in SaaS.
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