I’m a Sales Manager - How Should I Start Using AI Today?
Three coaching workflows you can run in any LLM today
DEAR STAGE 2: I saw your post on ideas for AEs to start using AI in live deals and wondering if you have similar advice for managers? I manage nine AEs and feel constantly reactive. How can I start using AI more effectively? ~OVEREXTENDED MANAGER
DEAR OVEREXTENDED MANAGER: If you missed it, here’s the article on how AEs should using AI in live deals. To be clear, there are lot of great solutions out there, but I was trying to share some actionable advice that an individual could implement (aka not company-wide, no business case or new budget). Addressing the same question at the manager level, it comes down to coaching. Here are 3 ideas to get you started with any mainstream LLM:
1. Pattern Recognition Across Calls
Instead of reviewing one call at a time, upload 5–10 transcripts and ask:
What patterns show up in lost deals?
Where is discovery shallow?
Are reps multi-threading effectively?
What objections are recurring?
Most managers rely on anecdotal memory when AI can surface trends quickly. You still validate the conclusions, but you start from signal instead of guesswork.
→ Key Takeaway #1: Use AI to find patterns. Use your experience to interpret them.
2. Create Personalized Coaching Plans
After reviewing a rep’s recent calls, prompt:
What 3 skill gaps are most evident?
What drills or role-play scenarios would strengthen those areas?
What metrics should I track over the next 30 days?
Instead of vague feedback (“ask better questions”), you can walk into a 1:1 with:
Specific moments from calls
A clear development focus
A measurable improvement plan
That changes the quality of the conversation and allows you to scale yourself as a manager. One thing worth knowing: managers tend to lean into the back-and-forth style v. being told what to do. That’s exactly why coaching-plan workflows like this work best!
→ Key Takeaway #2: Coaching should feel hyper-customized.
3. Upgrade Your 1:1 Prep
Before your weekly 1:1:
Input CRM notes and pipeline data (connect the data sources to make this easier if you can!).
Ask for a summary of leading indicators.
Identify deals at risk based on stage aging
This gives you sharper questions:
Why has this deal stalled?
What’s the next customer-committed action?
Where are we single-threaded?
AI sharpens your agenda and saves you meaningful time on admin work. You can even take this a step further and start automating these workflows to land in your inbox morning of a 1:1 or summaries at the end/start of a week.
→Key Takeaway #3: Managers spend less time on administrative prep.
Until next week!