56 Questions to Ask During a Sales Cycle

I’m sure there are 500 questions that could be asked in a sales cycle, but below is a list that has helped me hone my sales ability over the years.

A professional salesperson asks great questions.  They listen.  And they ask more questions.

Real information leads to clarity.  Clarity leads to solving problems.  Solving problems leads to deals.

Insert these at various points in the life of a deal.  They’re broken down into Money | Decision | Options | Challenges | Urgency.

Happy selling.



Is this something that would be allocated in your department’s budget?

Have you struggled to stay within your budget in past years?

What happens if your entire budget isn’t spent?

Is it rare for your company to increase your budget year over year?

Money is always a sensitive topic, can we talk about it early on so we can be sure this is a fit for both of us?

Is there a specific dollar amount that you’re allowed to approve without input from others?

Will this decision be based solely on price?

What happens if we come in higher than our competitors?

What happens if we come in lower than our competitors?

If you were to build the perfect proposal for this solution, what would you pay for it?



Who else, besides yourself, needs to be involved in this decision?

Can you unpack your company’s decision making process for me / who specifically is involved?

Would you be able to describe the personalities of the team making the decision?

What factors are critical to them?

Could we schedule a meeting with all of the appropriate parties?

At what point does the board get involved?

At what point does the legal team get involved?

Is that internal or external counsel?

How will your team react to your decision?

Should we include some of your team in these meetings so adoption is higher when we move forward?

How can I help you?

What would make your job more fun?

Is there anything I can do to serve you?



Who else are you considering for this solution?

Our competitors do a great job, what specifically appeals to you about them?

What concerns do you have about them?

Do you have a specific evaluation criteria set to evaluate all options?

If so, can you share those requirements?

If not, we’ve built these for other clients before, would you like us to provide an evaluation criteria for you?

What happens if you don’t do anything?

What happens if you move forward with a vendor and it ends up being a bad fit?

Why would you change vendors / partners at this point?

Who can be promoted or demoted because of this decision?

Do you trust us?

How can we earn your business?



What work stuff has kept you up at night?

Why is this a priority now?

Has there been a specific decision that this needs to be addressed soon?

Why are we meeting?

What do you have to lose if this doesn’t get solved?

What does your team have to lose if this doesn’t get solved?

How will the impact be measured if you take action?

How will the impact be measured if you don’t take action?

How is that working for you?

How have you tried to address this in the past?

Is there a personal agenda for you in this?



Is this a real priority or a perceived priority?

Would you classify this as a top three issue for management?

If we presented the perfect solution, how soon could we get to work?

Are there things on the horizon that will take precedent?

Do you have the internal team in place to execute this plan?

Why would this get delayed?

Why would it get accelerated?

Has this been a problem for over a year?

Has this been a problem for over five years?

Why hasn’t it been taken care of already?

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