The 5 Questions I Ask Before Any Enterprise Sales Call

Enterprise buyers give you a limited number of conversations. The first one sets the tone for every one after it, so I prepare questions before I prepare anything else.

I learned this while selling enterprise software and teaching sales methods at Oracle. Solution selling, SPIN selling and executive selling each have their own vocabulary, and they share one habit: understand the buyer's situation first, then describe the product. These five questions are that habit on one page.

1. Who feels this problem most?

Name the person whose day gets harder because of the problem. This is your likely champion, the colleague who will explain your idea to others when you are out of the room. Write down their title and one sentence on what a hard day looks like for them.

2. What does the problem cost today?

SPIN selling calls this the Implication question. Plan one question that invites the buyer to size the cost in time, money or risk, in their own numbers. For example, if a team re-enters data by hand each week, ask how many hours that takes and what those hours could produce instead.

A cost the buyer names carries more weight than a cost you estimate. It also gives the next meeting a reason to exist.

3. What does success look like in their words?

Solution selling starts with the buyer's picture of a better future. Prepare one open question, such as: "If this works well a year from now, what is different?" Repeat their phrases back in your follow-up note. Buyers trust people who use their language.

4. Who else needs to say yes?

Enterprise decisions travel through several people: a user, a champion, someone who controls the budget, and often security, legal or finance. MEDDIC-style qualification keeps track of these roles. Before the call, list who you expect to meet and who you still need to meet, and ask about the rest in the last ten minutes.

Executive selling adds one more step: earn a conversation with the person who owns the outcome. A champion who offers an introduction is a strong sign the buyer sees value.

5. What next step do I want, and what earns it?

Decide the exact next step before the call: a technical review, a second call with a colleague, a pilot plan, a date. Then choose the one moment in the call where you will ask for it. Calls that end with a dated next step keep deals moving.

Your one-page prep card

1. Champion: who feels the problem, and what does a hard day look like?
2. Cost: which question helps them size the problem in their numbers?
3. Success: what open question draws out their picture of a better year?
4. People: who decides, who influences, who is still unknown?
5. Next step: what do I ask for, and when in the call?

Print the card or paste it into your calendar invite. Five minutes with it before each call is a habit that grows stronger with every conversation.

Why this suits founders

Founders already hold the strongest asset in early sales: deep knowledge of the product and the problem. The card adds structure so every call teaches you something and every call ends with a next step. After a dozen calls, patterns show up in the answers, and those patterns become your sales playbook and the job description for your first sales hire.