Weekly roundup by Ioanna, Co-founder & CEO, Dextego
Looking back 2025 was the year Dextego proved something big:
AI coaching isn’t the future of sales performance. It's already here, and it’s changing how teams operate in real time.
This year stretched us, sharpened us, and clarified what sales organizations will need in 2026 and beyond. Thank you to our team, clients, partners, podcast guests and all of you for your support! We posted a 2025 recap video here.
The reason enablement fails isn't what you think
Sales teams think enablement fails because of content. From my experience it fails because humans don’t change without feedback...
Most orgs are overflowing with decks, playbooks, and training sessions. The problem is that none of it meets the seller at the exact moment they’re trying to apply it with a live buyer.
Without feedback, content becomes shelfware. With feedback, even average content can change behavior.
I think of feedback in three levels:
None: reps are left alone with their calls so performance depends on instinct and luck.
Delayed: quarterly call reviews and retro sessions. These can be helpful, but the emotional moment is gone.
Live / near-live: specific, behavior-based feedback tied directly to what just happened in a conversation and this is where behavior finally shifts.
Proactive: brief prep before key calls aligning on intent, questions, and risks so the seller goes in with a sharper plan and not just a script.
When teams move from level 1 or 2 to level 3 and 4, win rates and confidence look completely different.
What level would you say your org is in?
Throwback to our Dextegon AI Summit 2025
Here is the full speech of Ben Bartolone, who talked about the growing anxiety around artificial intelligence creeping into our daily lives, especially in the workplace. We're talking specifically about the fear of AI replacing human connection, particularly in fields like sales. Is the future of sales really about robots closing deals, or is there a crucial element that machines just can't replicate? 🤔
Dextego on social media
Most companies promote people into leadership roles and hope they’ll figure it out.
But the truth is simple: leadership isn’t instinct, it’s a skill set.
And most managers never get the reps to build it.
That’s exactly why we built Arden, our AI Leadership Coach.
Arden helps managers master the skills that actually move a team forward:
-Coaching people instead of micromanaging
-Delivering feedback that lands instead of backfires
-Navigating conflict without avoiding it or escalating it
-Setting direction that creates clarity, alignment, and momentum
-Developing employees so they can develop others
Leadership is a chain reaction. When one manager grows, their entire team rises with them.
With Arden, we’re making that growth accessible every day (not just once a quarter in a workshop nobody remembers).
This is what the future workforce needs:
Managers who know how to coach, communicate, and create real human traction backed by an AI partner that supports them in the moment.
If you’re building strong teams for 2026 and beyond, this is where it starts!
Here are 3 ways in which AI Coaching makes sellers more human.
Vince talked about the real sales gap today. Watch the video here.
The #1 mistake leaders make when rolling out AI tools👇
Most rollouts sound like this: “Surprise, here’s a new platform. Training is on Thursday. Good luck.” Then everyone is surprised when adoption is low and resistance is high.
Tools don’t fail because of features; they fail because they collide with human behavior with no narrative, no support, and no coaching.
A simple 3-step sequence works much better:
Narrative: Explain the “why” in human terms aka what pain this solves for reps and managers.
Training: Show people what good looks like in their real workflows, not in a sandbox that doesn’t match real life.
Coaching: Commit to reviewing what the tool surfaces and turning it into specific, safe feedback loops, not monitoring.
Some Dextego Love
“Dextego has been a game-changer for me and the teams I work with. I’ve recommended it to clients who want to level up their communication at work, especially for sales meeting prep and real-time coaching. What I appreciate most is that Dextego doesn’t just throw out generic tips—it gives me tailored, actionable feedback after every call, showing exactly where my influence landed and where I can improve. This has helped me shorten sales cycles and sharpen my discovery skills.
The personalized experience is a standout: Dextego adapts its coaching and recommendations to our playbook, best practices, and even my DISC profile, so the advice actually fits how I work and who I am. As a fractional executive, I’ve found the insights on buyer personalities and conversation style to be spot-on, making it easy to flex my approach without losing my own voice.
-Ellissa Carol, Sales Enablement Consultant
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That’s it for this week.
We’re building the future of coaching together.
Thanks for being part of it.
— Ioanna & the Dextego Team
PS: Do you want to know your leadership style? Try our 2 mins quiz here.