(And What to Do Instead)
In complex sales, small missteps cost big money. The stakes are higher. The sales cycles are longer. And there’s more pressure to make every touchpoint count. But too often, enterprise teams rely on outdated tactics and gut-based coaching to get deals across the line and it shows in stalled pipelines, burned-out reps, and missed targets. Here are the top 10 mistakes enterprise orgs keep making in complex sales — and how to fix them with better systems, better insight, and better support.
1. Hiring for Output, Not Coachability
Enterprise teams often prioritize past performance over adaptability. But the reps who succeed in complex sales today aren’t just closers — they’re learners.Coachability is the leading indicator of long-term success.💡 Fix: Hire for grit, reflection, and feedback uptake — then give them tools like Dextego to accelerate their development.
2. Delaying Feedback Until the Deal Is Dead
Too many sales orgs run post-mortems after the loss — when it's already too late to fix anything.In complex sales, every insight delayed is momentum lost.💡 Fix: Build real-time coaching loops into the rep workflow so feedback happens while the deal is still alive.
3. One-Size-Fits-All Training
Enterprise buyers vary. So should your sales coaching. But most reps get trained like they’re selling the same way, to the same persona, in the same vertical.Generalized coaching = underprepared reps.💡 Fix: Use AI to personalize coaching based on each rep’s strengths, weaknesses, and deal complexity.
4. Overengineering the Sales Process
Lengthy playbooks and rigid qualification frameworks often slow down reps more than they help.Complex ≠ complicated. Don’t confuse structure with bureaucracy.💡 Fix: Keep the process focused on outcomes — and let coaching adapt to the nuance of the deal.
5. Forgetting the Human Side of Selling
In high-ticket sales, trust > tactics.No one wants to buy a $500K solution from a script.💡 Fix: Coach reps on tone, confidence, and presence — not just talking points. Tools like Dextego help track that in real conversations.
6. Making Managers the Bottleneck
If feedback only flows from the manager, coaching breaks when they’re busy (or out of touch).High-leverage teams don’t just coach top-down — they coach peer-to-peer and rep-to-self.💡 Fix: Equip reps with automated feedback tools so they’re not waiting on a calendar to grow.
7. Failing to Map the Buying Committee
Enterprise deals fall apart when reps focus on one champion and ignore the rest of the room.The bigger the deal, the more invisible blockers you’re up against.💡 Fix: Train reps to multi-thread, track engagement, and align messaging across the full buying unit.
8. Letting Ghosted Deals Linger in the CRM
Nothing kills pipeline health like optimism bias.If you’re coaching ghosted deals more than active ones, something’s off.💡 Fix: Score deals based on live activity and coach reps to move fast on next steps — or move on.
9. Ignoring Soft Skills Because They’re “Hard to Measure”
Soft skills are the silent deal breakers — tone, timing, curiosity, empathy. Yet most orgs skip coaching them because they seem subjective.Just because it’s harder to measure doesn’t mean it matters less.💡 Fix: Use AI to surface tone and pacing issues so you can coach with clarity, not vibes.
10. Underestimating the Cost of Plateaued Reps
It’s not just about hiring great reps. It’s about keeping them great.The cost of a stalled seller isn’t just quota — it’s morale, culture, and compounding opportunity loss.💡 Fix: Invest in systems that make reps better continuously, not just during onboarding.
Coaching Problems + Fixes
Start Winning Smarter
Don’t let the deal complexity become an excuse for coaching chaos.If you’re managing an enterprise team and want:
- Coaching that sticks
- Systems that scale
- A sales culture reps actually want to stay in…
👉 Try Dextego Freemium today
Because your reps don’t need more pressure.
They need better tools. Want more sales insights like this?
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