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Whoever asks the questions controls the conversation- Intelligent sales tips

Abhishikha Chatterjee
Published :
Nov 2, 2021
Updated :

Why should sales associates not be afraid to ask the right questions? What are the common mistakes when asking sales questions? Why do you need sales coaching for better probing skills?

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Remember your first date?

What a nervous wreck you were?

But what was that performance in front of the mirror? Were you rehearsing? Role-playing the situation? 

Haven’t we all been in the same shoes? We have asked weird questions to a mirror or a friend. Why? So, that we don’t embarrass ourselves in front of our date.

A date is as close a scenario as a sales meeting. Your date is a stranger (in many ways), yet you have researched them well and recognized the right questions to know them better.

Clearly, one date can lead to another or may not. And that depends on how well the conversation went. 

Did the date(the prospect) go well? Did they find any value in your questions, or was it plane bombardment? Did they feel heard? Was the conversation engaging or boring?

If anything we know about dates and sales meetings, both the scenarios can turn into success only if you ask the right questions and the other person feels heard. 

Now let’s wake you up from reminiscing about your first date and talk about serious sales problems. 

What we’ll discuss today?

1. Why should sales associates not be afraid to ask the right questions?
2. Become a master of asking Sales questions

  • Type of questions
  • Sequence of questions
  • Work on tonality 
  • Help buyers realize the root problem
  • Active Listening 
  • Validate with questions

3. Common mistakes when asking sales questions
4. Why do you need sales coaching for better probing skills?

Why should sales associates not be afraid to ask the right questions?

“You never lose. You either win, or you learn.” - Nelson Mandela

Often, sales associates are clouded by the fear of probing their audience.  They say;

I’m scared to ask a question because;

  • I don’t want to be rejected. 
  • I don’t want to hear a NO.
  • I don’t want to cringe with embarrassment.

But what they fail to realize is that if you don’t ask, you don’t get!

Do you want your prospects to open up? If you do, you have to ask the right questions. 

Seasoned sales leaders will testify- Even though all sales conversations don’t turn into winning deals or the perfect closure, they are learnings that help crack the next sales deal. 

The more questions you frame and ASK, the more insights you gain from your buyer.

As far as asking questions is concerned, we’ll help your reps create tactful and contextual questions that resonate with their audience.  

So, how do you ask the right questions?

1. Become a master of asking questions

“Telling is not selling. Only asking questions is selling.” - Brian Tracy.

Focus on the type of questions

For one thing, sales experts categorically advise focusing on the type of questions. Most sales managers will agree?

Because asking questions will help your team set the foundation for the story to narrate in the proposal. If not proposals, you can identify if the customer is a right fit or not and worth chasing.

So, here’s our take on the type of questions to ask:

  • Discovery questions (Foundational questions)

    Questions that clear the air and open the door for knowing your customer. 

    You can ask very general questions to set the stage for more specific questions. Such as:

    1. How can we help?
    2. Could you please tell me a little about your current process?
    3. Where is your business today?
    4. Where are you falling short?
    5. How do you envision our partnership?
    6. What business parameters would you like to improve?

  • Surgical questions(Specific Questions)

    Now that the foundational questions are answered, you can start extracting and framing more specific questions that answer more critical questions such as:

    1. What did you do in the past to solve the problem?
    2. What are you uncertain about?
    3. Does your competition face the same problems?
    4. Can this problem impact employee productivity?

  • Validation questions

    There’s a clear chance that you have researched about your buyer and their business and made several insightful assumptions about them. 

    You may already know a few pain points and figured the financial status, decision-makers, and organization’s structure. The client’s information could be traveling from multiple directions, coming from various stakeholders. That means facts gathered from numerous sources. Is that reliable?

    While at the sales meeting, validate the facts and be absolutely sure about every detail about the client. Make sure you check for assumptions, as well as any personal opinions or beliefs you hold. You can ask questions like;

    1. Besides the three stakeholders I know, is there anyone who could join us for the demo meeting?
    2. Could you share their name and designation?
    3. Have you recently joined this company?
    4. Is it safe to assume that your current process is manual and you are looking for automation?

  • Leading questions

    Indicative or leading questions are slightly risky yet the most thoughtful questions a sales guy can come up with. They’ll either offend the prospect or give you internal information that was hard to receive otherwise. (Try at your own risk!)

    1. It looks like your company needs software for employee reporting desperately. Am I right?
    2. We don’t see you continuing the current project implementation process. Do you?
    3. In case you have looked at any alternate options, where would you rate our quotation?

2. Be conscious about open-ended and closed-ended questions

Asking an open-ended question and a closed-ended question can direct the conversation in two different directions. So be careful how you frame your question.

1. Open-ended questions-  Let’s say you need feedback or need confirmation on a query. You use open-ended questions like; 

  • Tell me more about your business? 
  • How do you see the company using our solution? 
  • What do you know about our services?

The beauty of open-ended questions is it sometimes blesses you with more information that you need or aids in building better and more specific questions.

2. Close-ended questions- Looking for a question to wrap a conversation or get a to-the-point answer? For example;

  • Do you have a budget? 
  • By which month do you wish to achieve ROI? 

But what we’d like you to observe here is that 2 questions can mean the same but can be asked in different ways. What should a sales rep choose?

  1. Would you like to discuss the new functionalities another time? 
  2. What would you like to discuss the next time we meet?

3. Take charge of the sequence of questions

A sales manager realizes the importance of building a story. 

Unless there’s a sequence of events appropriately mapped, sellers can find themselves at the crossroads figuring out what does the prospect need? 

Focus on building a story and extracting information in a meaningful way. 

Pose like a detective or a journalist. See which information can help you build a powerful case. 

For instance, out of the many questions, some sales guys will prefer to ask questions in this sequence:

  1. How have you tried to fix the problem?
  2. Have you evaluated anyone else in the market?

Why do we sequence the question this way?

The first question will most likely answer the competition’s product features(if used) and incumbent solutions features and gaps. The second question will validate the competition’s name.  

The second question’s answer is dicey and sometimes kept confidential by the buyer. The first question is usually answered without any hesitation. 

Another example could be:

  1. What made you understand that your company needs to shift to automation?
  2. Which teams will be using the solution?
  3. Can you help us understand the timeframe for implementation and when you wish to start using the solution?

So, do you get where we are going with the questions?

3. Work on your tonality 

A question alone can’t play the game.

Your tone should be approachable and optimistic.

Don’t try to sound interrogative. You may lose them any moment!

Try to tone down and modulate your tone based on the reaction from the prospect.

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4. Help buyers identify the root problem

Often questions can help the buyer. How?

Clients are aware of the surface-level issues and overlook the root cause. (Or completely unaware of a blind spot in the business.)

For example:

  • You mentioned the finances look great. The company is making a profit. But yet the employees are overburdened with work and are unproductive. Are there too many manual tasks? 
  • If I hear this correctly, the other teams have a budget for the solution. But marketing doesn’t? Have you checked for surplus resources, or does the budget needs revisiting? 

5. Focus on Active Listening

Questions are essential and keep your prospects engaged. But prospects want to be heard too.

Keep all distractions away and give your 100% to the stakeholders.

Good news: This will help you frame better and more specific questions otherwise challenging to answer.

Make your prospects feel heard. Acknowledge there’s a problem and stop arguing about it. You need to give them the benefit of the doubt and accept where they are coming from. 

6. Validate with questions

This may not be a real question, but you’ll need to validate and confirm if your understanding is correct. 

For instance, you can ask;

If I understand correctly, you are planning to evaluate till November, and then the implementation starts by December?

From what I can gather, currently, the company doesn’t have a budget, but the company wants to understand if there’s scope to automate email outreach?

Keep checking with your prospect. 

Quick Tip: We have an in-house expert who validates statements like a pro. Catch our founder and CEO- Ashish Santhalia, on Sales Gambit podcasts. You’ll love his articulation and validation techniques!

Common Mistakes While Asking Sales Questions

1. Did you allow buyers to ask questions?

Call it courtesy or a must-do, but you must give your buyer a chance to ask questions. You can’t expect to ask all the questions and wrap up the meeting. 

Let’s say you ask 60% of the questions to qualify and probe the prospect. Let the prospect ask 40% of the questions. Just say-

Have you got any questions you’d like to ask me?

2. Did you confuse your prospect?

Reps often confuse the prospect by asking an overcomplicated question that could have been articulated in simple words. 

With complicated questions, you’re just inviting more challenging reactions. 

3. Did you sound condescending?

Okay, we accept you know more than the prospect at times. But they don’t need your arrogance and attitude when asking questions. 

Ask what you need to, but the questions don’t need to sound condescending to the audience. 

4. Are you asking close-ended questions?

We are not biased towards open-ended questions, but we see a problem with too many close-ended questions. 

Close-ended questions wrap up meetings quickly and don’t add any value to the sales conversation. 

We aren’t saying NO but use close-ended questions wisely.

5. Are you making decisions for your prospect?

Won’t it make sense to start the implementation next month?

Why don't you set up the meeting next week so we can get this done?

The above questions are not right or wrong, but they are not eligible for prospecting. 

Don’t make decisions for your buyer. Help them in making one!

6. Are you listening to the prospect?

If you aren’t listening carefully, you won’t read between the lines and, most importantly, have no questions to ask.

Be attentive and listen to the more minor details discussed on the call.

7. Are you referring to a script?

Using a script is fine. There’s no harm using it. 

But that doesn’t mean you mug up the entire script and don’t make any changes at all.

Disclaimer: A sales script is meant for reference, not to be consumed as it is.

8. Did you ask the wrong questions?

If anything can wrong in a probing conversation is that your rep ends up asking irrelevant questions. 

For instance: the product is for marketing purposes, and you keep collecting details of the HR team. Why in God's name would you do that?

9. Did you check with them?

A common yet ugly mistake is not to check with your prospect. 

They may be physically present but mentally in Rome. Just saying!

You must interrupt the meeting to check if they are with you?

Pay close attention to their tone, body language, choice of words, and anything else that indicates active listening. 

And, yeah, don’t overdo the checking thing. Keep it subtle and graceful. 

Now, how do you ensure you implement the best practices and avoid making these common mistakes in your next sales meeting? 

Why do you need sales coaching for better probing skills?

Without beating around the bush- Invest in sales coaching

Managers, if you want your reps to ask witty and meaningful questions, you must shift gears to ensure enhanced customer engagement. 

Sales coaching can help in sharpening your reps’ probing skills. They can not only ask better questions but also start framing questions independently and spontaneously with coaching in the background. 

Role-playing is the best way to charge the question-and-answer session.

Reps can boldly face the sales coach and ask questions in their mind without any filter. And sales coaches can ensure the best gets filtered for the customer.

Coaching doesn’t mean only role-plays and template creation. The right coaching can also teach your rep to ask killer questions for a better response. You’d know if the rep is ready to face a giant shark in the market.

Coaches who invest in conversation intelligence can identify a call the rep has blown while learning from the meeting. 

Now is the time to discuss the sales playbook. 

If your team needs reference questions, you’d need to keep prospecting questions ready in the store. 

Apart from the above, we missed one crucial point. 

“You see, when you ask questions, it takes all the burden off of you, and it feels like you’re giving control to them, to the person you’re asking the question of, because they’re the one doing all the talking.”

Hence teach your reps to use the weapon(questions) as a catapult to increase sales performance

Don’t be afraid to ask…

...the right questions!!

Not just in sales, but also life. 

Asking questions is harmless and usually solves the problem or completes the task at hand. 

Asking the right questions means you help your customers with directions.

Without knowing the customer well, you may end up delivering an incorrect outcome and find your sales targets flying in all directions.

And of course, you don’t want that!

Asking good questions cuts through the noise, and creativity gets them talking more.

Hence, ask questions and ask the right questions.

And what do you do about that?

You invest in sales coaching and practice asking questions to your prospect. In parallel, you work on a list of sequential questions and master the tonality of asking them.

Primarily, don’t leave your confidence at home. Ask questions and ask them with confidence!


Bonus Tip: We thought this is the best way to get you started. Here’s a FREE version of recording your role play with your sales manager and evaluating your confidence level as well as questions quality- GO SIGN UP NOW!

Like this blog? Here's a podcast that might interest you:
Sales Gambit Podcast
Host : Ashish Santhalia
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