Early in my career, I sold high-end IT solutions to enterprise clients. I was working a deal with a big bank. My contact was an Executive GM. Senior, confident, and excited.
Everyone from her to the tech team seemed on board. It felt like a done deal.
Then the end of the quarter came and went. (You can imagine the pressure from my boss… “Are we there yet???”
Eventually, we heard back:
“Legal’s holding it up. Procurement wants a better price.”
The buyer loved the solution, but she didn’t know how to navigate her own internal process.
That’s when I learned a painful truth:
Most B2B buyers aren’t experts at buying. They rarely make large purchases and don’t always know who needs to be involved. If you don’t guide them, deals stall.
Here are the questions I now insist every salesperson I coach ask:
- How long has this been a problem?
Old issue? Why hasn’t it been solved yet? New one? Are they ready to act?
You’re not just qualifying urgency and priority. You’re testing readiness to change.
- Have you bought something like this before?
First-time buyers need more help. Your job: de-risk the decision. Provide more social proof. More handholding. A clearer implementation roadmap.
This isn’t just about selling. It’s about helping them feel safe.
- Who signs off at this price point?
Don’t assume your contact has the final say. Ask who else is involved.
Ask directly:
“When you’ve bought something at this price point before, who’s typically needed to sign off?”
You’re not challenging their authority. You’re showing experience and helping them realise this isn’t just a one-person decision.
- Who could block this? Who’ll push it forward?
“If someone were going to object, who would it be?”
“And who’s most likely to push it forward internally?”
You’ll uncover hidden landmines and unexpected allies. Deals often get killed by someone who never speaks to the salesperson. Don’t get blindsided.
- Do you have budget or are you trying to get it?
Big difference.
One means the money’s there – they just need a yes. The other means you’re still in justifying-the-spend mode. Different timelines. Different pressures. Different conversations.
If the budgets not secured, shift your focus to helping them build the case internally.
- What’s your internal sign-off process?
This question does two things:
- It gets the buyer thinking ahead (which speeds them up).
- It uncovers unseen steps that can derail you later.
If they can’t articulate their internal process, you need to guide it.
- What role will legal and procurement play?
This is where many deals get stuck. Legal’s job is to slow things down. Procurement’s job is to squeeze margin.
“Have legal and procurement been involved yet? What do they usually care about in deals like this?”
Just knowing their process lets you pre-empt roadblocks. And it shows your buyer you’re not naive.
Final Thought:
Stop letting your buyer fumble their way through a decision-making process they barely understand.
Take control. Ask the deeper questions. Map the internal maze. Guide them step-by-step.
Because when you do?
- Forecasts become more accurate.
- Fewer deals slip.
- Your CEO and board start seeing consistent results.
That’s when sales move from guesswork… to strategy.
That’s what strategic selling looks like.
