Get WISER with Your AI Prompts - A guide for sales managers

Everyone’s wittering on about AI like it’s the second coming. But here’s the rub: if you give it half-baked prompts, you’ll get half-baked answers. Garbage in, garbage out.

The problem? Most people type into ChatGPT/Claude etc. the way they’d WhatsApp a mate: rushed, vague, and with zero context. And then they wonder why the output sounds like a space cadet wrote it. If you want useful, business-ready answers, you need to "brief the machine" properly. .

Embedding AI into your sales process and unleashing its productivity benefits means providing your team with guidance on how to achieve good results from their interactions with AI...ohh and permission to experiment and share the results, after all, we are still living in the era of AI wild west and it's often unclear where the wins will come. The WISER framework will help you and them. 

In our experiments at g2m, I have adopted the WISER framework as a starting point and connected ChatGPT to our HubSpot CRM. It's been eye-opening. Analysing closed won and lost deals, forecasting near and long-term scenarios based on seasonal actuals has been a big win for me.

What’s WISER?

It’s a five-step checklist that forces you to stop being lazy and tell AI what it actually needs:

• W – What you want: Spell out the problem or goal.
  
  
• I – Information you have: Give the background facts.
  
  
• S – Steps you’ve taken: Explain what’s been tried already (so it doesn’t parrot it back).
  
  
• E – Expected output: Describe what format you want and how detailed it should be.
  
  
• R – Role: Tell the AI who it should pretend to be.
  
  

Sounds obvious. But try running your next challenge through those five lenses and see how much sharper the response gets. It's a good starting point; you can always dig deeper on specific elements of the challenge. 

Let's Take A Common Business Headache: Sales Pipeline Visibility

Here's a scenario every B2B sales leader knows too well:

• Forecasts are a guess at best.
  
  
• Sales reps update deals late (if at all).
  
  
• Each team uses pipeline stages differently.
  
  
• Dashboards exist, but no one actually looks at them.

The WISER Prompt

Here’s how you’d brief AI on that problem, WISER-style:

W – What you want
“I want to improve visibility into my sales pipeline so my leadership team can make better forecasting decisions.”

I – Information you have
“We use HubSpot CRM. Reps often update deals late, stages aren’t consistent across teams, and reporting is messy.”

S – Steps you’ve taken
“We built dashboards (ignored), told reps to update weekly (ignored), and never standardised pipelines.”

E – Expected output
“Give me a step-by-step action plan with quick wins for 30 days and bigger fixes over 90. Break it into process, tech, and people.”

R – Role
“Act as if you are an experienced HubSpot consultant who’s fixed this exact mess dozens of times.”

The Full Prompt

“I want to improve visibility into my sales pipeline so my leadership team can make better forecasting decisions. We use HubSpot CRM, but reps often update deals late, and pipeline stages are inconsistent across teams. We have some historic deal data, but reporting is messy. We’ve created dashboards with low adoption, coached reps to update deals weekly (compliance is spotty), and haven’t standardised pipelines. Act as a HubSpot consultant who has seen dozens of B2B companies solve pipeline visibility issues. Give me a step-by-step action plan, including quick wins for 30 days and longer-term fixes over 90 days, broken into process, technology, and people.”

That’s a world away from the sort of limp prompt most people type in: “How do I fix my sales pipeline?”

Why It Works

• The AI knows the problem.
  
  
• It has context (tools, adoption issues).
  
  
• It won’t regurgitate things you’ve already tried.
  
  
• It knows the deliverable (step-by-step plan).
  
  
• It’s wearing the right hat (consultant, not motivational speaker).
  
  

The result? A practical, tailored response instead of a reheated listicle.

The Takeaway

AI isn’t clairvoyant. If you brief it like a junior hire, you’ll get junior-level answers. If you brief it like a grown-up consultant, you’ll get grown-up output.

So next time you’ve got a thorny business problem, don’t just type your frustration into the chat box. Get WISER (see what I did there?)