Sales Professionals are getting worse. I’m serious.
After 15 months, over 1000 hours of role-plays with various teams, and more than 1500 sales calls reviewed, the patterns and takeaways are a bit staggering.
At The Question First Group, here’s what we’ve discovered across B2B and B2C. And please take notes, because there’s a good chance your team is somewhere in here as well:
Top 8 Sales Team Skill Deficiencies of 2026 (In order)
1. Shallow discovery
Surface level questions is a cancer in sales today. Most reps have literally no idea how to ask deep, connection-based questions. This therefore means they uncover symptoms, not root causes. Fact is, every sales team needs to go back to the literal drawing board of learning how to ask deeper, follow up questions. This is #1 on the list by a country mile.
2. Generic outreach and weak personalization
Spend one day on LinkedIn and you see the problem. Outreach is an unmitigated disaster for roughly 90% of the reps we meet. Why? They’ve literally never been trained what “right” looks like, causing most to live in an extraordinary state of outreach ignorance.
3. Weak value articulation
Many reps can explain what the product is, but not why it matters in economic or practical terms. Therefore, the prospect only focuses on the “price” and not the financial impact of solving the problem. This is the death of B2B selling in a nutshell.
4. Pitching too early
Good golly Miss Molly, this one is bad. Especially in SaaS. That industry needs a sales facelift but we’ll save that conversation for another day. We rush to pitch without identifying fully the issues/problems the prospect is having, the impact those problems are leading to, and the importance of solving those problems immediately.
5. Poor listening and weak follow-up questions
This goes back to #1 but most reps “think” they are good listeners when they are a 3 out of 10 based on our scores. Most are much more interested in what they want to say next versus actually hearing what the prospect is saying. This is one of the hardest bad habits to break for a rep, but it is absolutely possible to turn it around.
6. Weak stakeholder management
This one is huge in B2B but we certainly see it in B2C as well. Bottom Line: Reps don’t know how to change their approach and communication style to meet the stakeholders where they are and, ultimately, win them over.
7. Inconsistent process discipline
Ask most reps what sales system they follow and they can’t give you an answer. This means most are just making up next steps as they go, walking blind because leadership has never picked a sales approach and stuck with it. (In our world, The Pathfinder System was addressed to solve this very problem.)
8. Low AI and data fluency
Unmitigated disaster. Nothing here across most organizations at all. It’s like AI was never even invented for most sales reps. Stunning. The few that use it can be 10x more efficient than their counterparts.
Well, there you have it friends. These are the biggest sales problems, B2B and B2C, thousands of hours of training and observation have shown us over these past 15 months.
And please, remember: These things don’t just fix themselves. Bad habits will only get worse until fully addressed. We’ve seen too many leaders blame “market conditions” on their poor sales numbers, when in reality their sales team, for lack of a better phrase, stinks.
But, remember, this isn’t a sales problem. It’s a leadership problem. It always is.
Leaders decide where to allocate organizational focus and priorities.
This is also why we’ve found that less than 5% of organizations have any type of weekly sales “training.”
Sure, they might have sales meetings, but not sales trainings—and there’s a big difference.
So ask yourself: How many of these issues is my sales team struggling with right now?
Do we have a culture of “sales meetings” or “sales trainings?”
Fixing this starts with you, the leader.
So now is the time. Lead.
If you want your team to stop pitching and start guiding, download our book, The 4 Pillars of Breakthrough Sales Communication, here.