Thinking On Your Feet: How to Answer Difficult Questions

Did you close the deal?

Why should I hire you over someone else?

Do you love me?

Why should you get a bonus?

Questions… they can be simple to answer or they can get our adrenaline pumping and our palms sweating.

To have success in a sales role you need to learn how to answer difficult questions by thinking on your feet.

Because buyers don’t just ask questions to obtain information. Buyers ask questions for other reasons as well.

They might be trying to put you under pressure to see how you deal with stressful situations, they might be trying to understand your attitude on a subject without directly asking about it or they might be trying to test whether you are telling the truth in your sales pitch.

So lets jump into it and learn how to answer difficult questions…


When selling there are unlimited questions as a potential buyer could ask you. Therefore it is impossible to plan responses to each question ahead of time. So we need a system to answer tough questions and think on our feet.

Answering tough questions has two steps –

  1. Creating enough time to process the question
  2. Generating an answer that serves everyone in the conversation

Pretty simple right?

So let’s look at the first step to dealing with difficult questions which is to buy yourself more time.


Have you ever experienced this? A buyer throws a tough question in your direction and for some reason words start spilling out of your mouth uncontrollably?

One thing leads to another, to another and you’re suddenly wondering what the heck you’re talking about.

I’ve been there too.

This happens because most salespeople fear there being any silence on their side of a conversation.

Salespeople fear this silence because they assume the buyer will think that they lack knowledge on their product or their market and so will then reject them.

This isn’t very effective though. It would be like jumping in front of a train, expecting it to stop.

Unfortunately, when you blurt out a response to a tricky question without thinking it over, often this impulsive response is not going to be the best rebuttal you could have come up with.

So the most important thing you can do to improve your responses to difficult questions is to buy yourself a little bit more time for your brain to think.

How do buy this extra time?

Look at your buyer, pause in silence, making sure not to fill the silence with lots of “umm” and “errrr” and give yourself room to think.

Easy right?

A small pause like this will often indicate to a buyer that you’re not just a sleezy salesperson trying to flog whatever is the deal of the day and that you are truly trying to give them the best possible advice too.

If you need to buy yourself even more time to mentally process the difficult question, you can do what politicians do and repeat back the question to the buyer.

For example, if a buyer asks you –

“Are there are opportunities for discounts if we classify you as a preferred account?”

Well you can pause, then say –

“hmmm, are there opportunities for discounts if you classify us as a preferred account…? That’s a great question.”

This has now bought your brain an added 30 seconds to process the question and formulate a solid response.

Once you’ve bought yourself a little time to think up a response, step two of answering difficult questions is to hedge your response.


Most of the time in question becomes difficult to answer, not because you don’t understand what is being asked, but because you don’t want to answer all or part of the question.

This could be because the person who’s asking you the question is trying to manipulate you.

It could be because they’re asking you about something that is private that you don’t want to share.

Furthermore, buyers will often ask questions that are would derail you from the selling process if you answered them straight too.

Outside of your sales role, often the best response to a difficult question is to be assertive and say you do not want to answer the question. But things get complicated when need to continue a conversation to get a deal done.

So instead of directly responding to these difficult questions we are going to hedge our answers, so we remain in control of the conversation, but the buyer feels like the question was in fact answered.

There are two ways to hedge a question so let’s look at them now.  


If the difficult question is multifaceted and there are some aspects of it that you do not want to address, then focus only on the parts you do want to address.

For example:

Question – “I heard that there are big discounts coming with your product. I also heard that your business is in financial trouble and I even noticed that your website has not been updated in a long time. What is going on?”

Response – “We are doing an update on the website of the moment and so there’s going to be a lot of new content coming your way.”

Whilst on paper this example looks like it would leave the buyer dissatisfied with your answer, in reality most of the time that is not the case. If you respond to a single element of a multi-faceted question and then then follow on with an added question of your own the conversation will keep moving forward.

It’s rare that the buyer will yell stop and try and drag the conversation back.

If the buyer does circle back to the questions that were unanswered, then you can use the next method of hedging your question and refocus it.


To refocus a buyer’s question, pull out one word from the question and build your response around individual word. The more emotional the world you choose to pull out, the more satisfying your response will be.

For example:

Question – “Have you heard anything about the update that we were supposed to get? I really feel like this update will improve our team’s morale and make your service more useful to us”

Response – “For sure. The new update will dramatically improve your team’s morale”

Here we have focused on the fact that the new update will improve the buyers team’s morale whilst avoiding answering the question of whether the update is arriving.

Here’s another example with a price concern where we refocus the question and then ask our own question to keep the conversation moving towards the close.

Question – “Why would I sign a contract with you when your competitors services are significantly cheaper?”

Response – “Price is a crucial factor to consider. How much do you base your decisions the quality of the service being provided?”


The steps to think on your feet and answer difficult buyer question. To recap, the process is to –

  1. Buy yourself some time for your brain to process the difficult question
    • Embrace a moment of silence before you respond
    • Repeat the question back to the buyer to buy yourself more time
  2. Hedge the question and make it easier to answer
    • Respond to one aspect of the question that you feel comfortable answering
    • Refocus the questions down to one word and discuss that specifically

And if all of this fails it is fine to let your buyers know you’re unable to answer a question. You’re not on trial here in a court of law.

Don’t try and blag things, don’t tell white lies. Instead, assertively say you’re unable to answer the buyers question at this time and that will satisfy most people.

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