The Top 8 Questions to Ask Prospects to Sell More Effectively

There are plenty of sales questions we need to ask throughout the buying/selling process to help uncover a need, create urgency and gain commitment.

There are plenty of sales questions we need to ask throughout the buying/selling process to help uncover a need, create urgency and gain commitment. Here are the questions I ask and the reasons why:

1. What are the details of the decision-making process and who is involved? Or, 2. How have decisions like this been made in the past?

This might seem obvious but you’d be amazed at how many sales reps I see don’t ask this question or don’t get the details they need. If you don’t have a clear understanding of the decision-making process and exactly who is involved then you shouldn’t be surprised at the end when all of a sudden you have to go talk to procurement, legal, other stakeholders, or extend the trial or do a bake-off, etc. When someone gives a vague answer to this question you should push back and explain that by you understanding the details, you can help them make their buying process as efficient as possible by ensuring you have the right resources lined up on your end. If someone is unwilling to share the details I’d be worried about the quality of the opportunity and the likelihood of it closing in the first place.

3. What are your top business priorities for the upcoming year?

Hopefully we can do our research and find this information before any meeting but if not we need to understand the overall business priorities to ensure our solution aligns with them. The top business priorities are different than the priorities of the individual you are speaking with. They are typically what drive all decisions throughout the year on what the company will invest in and what the executive decision makers will sign off on. If your solution does not align with their business priorities then the likelihood of you selling them anything drops significantly. This also gives you a chance to move upstream if you’re dealing with someone below the ‘power line.’ Ask them this question and if they don’t have a good enough answer then you can say something like “I appreciate your insight but I’d like to understand then in a bit more detail so I can ensure the solution I put together not only supports your needs but also aligns with the overall business priorities directly so we can show an impact across the board. Is there someone else I might be able to speak with to gain this insight?”

4. What are your top priorities when making this decision?

This question is more directly related to the solution you are talking about and their evaluation criteria. By understanding their top three priorities when making this decision you can then hold them accountable throughout the rest of the process if they stray or change for whatever reason. As an example, if you ask this question and “price” is not on the list then towards the end when price inevitably does become an issue you can ask them if it is more important than the other three top priorities they spoke of earlier and you build your solution around. I usually ask for the top priorities and then include them in a ‘summary e-mail’ I send after the discussion and ask them to e-mail me back confirming they are accurate. This creates an audit trail that you can use throughout your conversations to reconfirm and remind them what they said.

5. Are you ok with telling me no?

This seems like a weird one to ask but you’d be amazed at how effective it is. No one likes telling anyone no which is why many times clients don’t even call us back towards the end of the process. If you get it out of the way upfront and let them know you are cool with them telling you ‘no’ then they are more likely to stop the conversation sooner if you really aren’t the right fit. Also, if you ask this question then towards the end you can remind them if they are avoiding you and have some fun with it by leaving a voicemail that goes something like this: “Hi Bill, this is John again with Salesforce. Remember early on when I asked you if you were cool with telling me no and you said you were? Are we at that point? If we are please let me know because this ‘maybe’ or ‘no response’ zone is killing me.” Remember, the worst sin in sales is not to lose a deal, it’s to take a long time to lose the deal. You want to get to a ‘yes’ or a ‘no’ as quickly as possible.

6. What’s the best way to communicate with you moving forward?

If you get someone on the phone and there are agreed upon next steps you should ask this question. Different people like communicating in different ways. Some like e-mail, some phone, some text, cell phone, etc. Don’t guess. Usually the answer to this one is going to be e-mail. If it is, then qualify it a little with something like “I’m sure you probably get 100-200 e-mails a day like me. Is there something I can put in the subject line that will get you to open it and respond to me?” You can then ask “I promise I won’t abuse it but when I do reach out to you it will usually in the interest of getting you what you need to make an informed and timely decision. With that, can I get your commitment that you’ll respond back to me in a timely fashion?” You need to set the communication ground rules and expectations upfront and let them know you respect their time as much as you do yours.

7. Will you be my Champion?

Too often reps think they have a Champion when they really have a Coach or a Fan. The two main characteristics we look for in true Champions are 1) they can steal budget and 2) they agree to be your Champion. This is someone who either has budget authority or has a heavy influence on the budget and sits at the table when the time comes to make the decision. With VPs of Sales you can ask this question directly since they understand what it means and will usually appreciate the approach. With other titles you may have to rephrase and say something like “do you agree our solution is the best one to address your needs? If so, when the time comes to make the decision on this will you fight for me as hard as I would if I was there?”

8. What happens if this decision doesn’t get made?

You should ask this question every time. The #1 competitor we all have is “no decision.” If the answer to this question is not specific and it seems like status quo would be ok for them to deal with then I would not forecast the opportunity. However, if there will be a specific impact to them (ideally negative) then you know what you need to focus on.

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