If Your Sales Strategy Feels Safe, It's Already Failing

Take a look at your team's last 50 outgoing sales emails. Read their LinkedIn messages. Listen to their voicemails. Are they sharp, challenging, and memorable?

If Your Sales Strategy Feels Safe, It's Already Failing

Or are they a sea of polite, predictable, and utterly invisible "just checking in" messages?

Let's be honest. Most sales teams are playing it far too safe. And in the noise of 2025, ‘safe’ is the most dangerous place you can be. It’s the fast track to being ignored. If your sales strategy doesn't feel a bit uncomfortable, you're not pushing hard enough—and you're leaving money on the table. This isn’t about being aggressive; it's about having the courage to be memorable.

The High Price of Being Polite

In a crowded market, comfortable is invisible. Your buyers have already heard the standard pitches. Their inboxes are graveyards for safe, boring emails. If your approach doesn't make them stop and think, it’s already failed.

• The Follow-Up Fallacy: Most salespeople give up after just one or two attempts because they don't want to "be annoying." But research from sales platforms like Outreach shows the average deal requires eight or more touchpoints. The teams willing to be professionally persistent are the ones who get the conversation started.

  
  

• The Insight Imperative: Buyers don't want a walking brochure; they want an expert who teaches them something. Studies consistently show that B2B buyers will take a meeting if the seller leads with a compelling insight about their business. But offering a real, challenging insight feels risky, so most reps fall back on just listing product features.

  
  

Stories from Teams That Dared to Be Different

Making your prospects a little uncomfortable—by challenging their thinking—is a sign you're providing value. This is "productive discomfort."

I know a SaaS company in the region that made a terrifying decision last year. They banned generic, one-hour product demos. Their sales team was panicked. Instead, leadership forced the team to create short, 5-minute personalised videos addressing a prospect's specific problem, which they sent in advance of any call. The result? Their pipeline of tyre-kickers shrank, but their close rate on qualified deals doubled. They started having fewer, but much more serious, conversations.

Another team I worked with was getting ghosted after their discovery calls. The calls were pleasant but ultimately pointless. We trained them to ask one direct, 'uncomfortable' question towards the end of the call: "Forgive me for being direct, but what is the real cost to the business if you don't solve this problem in the next six months?" The tone of the conversation changed instantly. It moved from a casual chat to a strategic discussion about risk. They started closing better deals because they were solving bigger problems.

A Playbook for Productive Discomfort

Injecting this approach into your team isn't about creating chaos; it's about a calculated strategy.

1. Start Chasing 'No'.

If your team isn't getting told "no" several times a day, their outreach isn't ambitious enough. A "no" is clear data. "Maybe" is a time-waster that clogs your pipeline. Track your rejection

rate—if it's near zero, you're not asking for enough or aiming high enough.

2. Ban "Just Checking In" Forever.

This phrase is a white flag. It signals you have nothing of value to say. Every single follow-up must offer a new insight or perspective.

• Weak: "Just following up on my last email."

  
  

• Bold: "I saw your company announced its expansion into Vietnam. When other firms in your sector do this, they often face [a specific customs challenge]. Here’s an article on how to get ahead of it."

  
  

3. Your Job Is to Challenge, Not Just Agree.

A true expert doesn't just nod along. They reframe the problem.

• Safe: "What are your biggest challenges right now?"

  
  

• Impactful: "Many leaders in your position are focused on solving problem X, but they often discover the real, hidden issue is actually Y. Has that been your experience at all?" This positions you as a strategic advisor, not an order-taker.

  
  

4. Make Bold the New Standard.

Build uncomfortable but effective actions into your standard sales process. Make it a rule that instead of generic LinkedIn connection requests, your team sends a short, personalised video. Instead of offering a standard demo, make an interactive workshop the default for highly qualified prospects.

This is how companies like Drift built their entire business—on the 'uncomfortable' idea of replacing lead forms with live chat. It made traditionalists uneasy, but it created a better buying experience.

The Difference Between a Challenger and a Pest

It's crucial to know the line. Being bold is about challenging a prospect's perspective with valuable insights that benefit them. Being pushy is about ignoring their needs to serve your own. Productive discomfort makes the buyer think, "Huh. I hadn't thought of it that way." Annoyance just makes them block you.

If your sales strategy feels completely comfortable, take it as a warning sign. It means you are invisible. Real growth lives on the edge of what feels slightly uncomfortable. That feeling isn't a sign you're doing something wrong; it's a sign you're on a path your competitors are too scared to walk down. Go there.