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Probing in Copywriting: 12 Ultimate Tips

Nothing is more important than mastering the ‘art’ of probing in copywriting.

Copywriters must ask their clients questions (probe) to:

  • Assess problems
  • Provide the best solutions
  • Succeed in copywriting.

But to save you learning the hard way (through ‘trial’ and ‘error’) and scouring the net (for hours) let’s discuss 12 ultimate tips to master the ‘art’ of probing in copywriting.

Read on or use the the table of contents to ‘jump’ to a specific section in the post.

Table of Contents

1. Be a Master Planner and Win

Great research is needed to conquer the ‘art’ of probing. And keyword, market and competitor research is your starting point.

But to come up with questions for your ‘client probe’ you need to put time, effort and energy into the:

  • Type
  • Wording
  • Number of questions (discussed next).

Note: For best results limit ‘preparation’ time, so that only ‘smart time’ is invested into preparation for the probe.

Type of questions: And these questions are unlikely to be what you first write down.

For example: What is your goal? 

This is a common question but it may not get you a clear answer.

So you could try: What is your exact goal?

By adding the word ‘exact’ you have made it clear you want an ‘exact’ answer.

Or you could try: I want to know (and in your own words) your exact goal for this project and what it would mean for you to achieve this goal?

Because (although this is ‘art’ – no right or wrong answer), in the previous step by:

  • Adding
  • Revising
  • Fine tuning

You’re more likely to receive the answer that brings you closer to the solution.

And the wording of questions?

That’s an ‘art’ and as discussed in this blog post – copywriting is 80% art.

But adding, revising and fine tuning words (as just mentioned) in your probe questions helps you master the ‘art’ of wording questions quicker.

And finally, the number of questions?

That’s ultimate tip #2 for probing in copywriting and let’s discuss it now.

2. Limit Your Questions to Enhance Quality

The greatest probers know that quality matters and you can only achieve best results from the probe if you limit the questions.

And we are talking about the big-picture questions that matter.

Try to limit your probing questions to 10.

But don’t sweat it if you go over. Because (as we discuss in ultimate tip #4. be personal and sincere to get further) if you are ‘sincere’ and ‘personal’ most clients will find the time to answer your questions.

But (by limiting them to 10) you are focusing on what matters.

3. Listen, Learn and then Act (absolute key)

When probing it’s critical to ‘be in the moment’ and not just ask a question because it’s on your list.

Never assume you’re a good listener – because according to Lifehack (in this resource) 90% of people are poor listeners. And if you’re needing further proof, check out this resource by Insider (12 signs you’re a bad listener – even if you think you aren’t).

Mastering listening is an ‘art’ (as discussed here by Lonerwolf) but when ‘probing’, hear the ‘complete’ answer to your probe.

And that means (even if you think it’s needed – for whatever reason) no interruptions!

Doing this means you are:

  • Listening first (whether that’s good or poor listening skills)
  • Learning (by being ‘in the moment’)
  • Acting (and ‘reacting’ based off what you hear).

These are all key to great probing results.

4. Be Personal and Sincere to Get Further

Personalisation and sincerity both matter in probing and will get you:

  • Further with questions (time becoming less relevant)
  • Completeness (getting to the end of the process with what you want).

And the power of using your client’s name (discussed in this great resource) is your starting point in ‘personalising’ the probing experience.

Don’t be afraid to repeat (without overdoing it – it’s an art) your client’s name throughout the ‘probing’ process to put them at ease more.

You can even compare ‘probing’ to shopping in terms of personalisation.

Because 70% of customers expect a personalised experience when they walk in the door.

Tip: If you’re looking to take your ‘personalisation’ skills to the next level, be sure to check out this great resource by Neil Patel.

Now to Sincere: Because the beauty of being sincere (and personal) is that you can never ask too many probing questions.

Because it’s more likely your client (within reason) will give you more of their time.

And being sincere (if not already obvious to you) can be mastered with these 8 great tips from Amerikanki, discussed here.

5. Be Direct and Get Direct (what you need)

You’re more likely to get ‘direct’ (from your client) when you’re direct, and the best outcome. But being ‘direct’ is an art (as copywriting is an art – discussed in this blog post).

Important: Never confuse ‘bluntness’ with ‘directness’, because being:

  • ‘Blunt’ is being honest (but often in a rude manner)
  • ‘Direct’ is being honest and genuine (while remaining diplomatic and respectful).

And if you’re still confused, check out this resource by Inc: 3 ways to be direct (without being rude).

But be aware that we live in a multicultural society (and Australia is a successful one).

Therefore, you cannot always be ‘direct’ and succeed in probing.

Because (sometimes) and for (certain cultures) being ‘direct’ may have you perceived as confrontational (or even rude).

Dealing with different ‘cultures’ in copywriting is a whole new ball game – and if interested – check out this blog post (coming soon).

6. Use Open-Ended Questions (to dig deeper)

Open-ended questions require more than a ‘yes’ or ‘no’ response.

Here are some examples in the table.

Open-Ended Question Example

Close-Ended Question Example

What were the main reasons you choose our product /


Would you recommend our product / service?

How do you feel about our customer service?


Did you experience good customer service?


How would you describe your experience with us?


Are you happy with your experience with us?


Asking ‘open-ended’ questions in probing is more likely to:

  • Encourage ‘in depth’ responses
  • Lead to greater discussion
  • Achieve a better solution.

Sales Hacker lists the top 35 open ended sales questions that keep conversations going (as a great starting point for any prober) but open-ended questions is an ‘art’ as discussed by Bill Cates here.

And it’s an art’ that is fundamental to probing success. 

7. Never Fear Being Dumb (as it may turn out smart)

Fear of looking stupid is the #1 killer of dreams.

And in ‘probing’ you must quickly master any fear of looking stupid (discussed here by Forbes) to gather all information necessary to:

  • Identify (the key) problems
  • Provide the best solution (that adds value).

Because remember, even the smartest people can make the dumbest mistakes.

And no one ‘knows everything.’

Because your client (whether they perceive the question as ‘valuable’ or not) will judge you off your results.

Therefore, never fear asking a ‘dumb question.’ As more often (than not) it will turn out smart!

8. Let them Speak (in their own words)

Great probing can help reach great conclusions with your client. 

But unless your client is speaking to you in another language (besides your native one) you should let them say it exactly how they want to say it – yes (in their own words!)

Because (to be discussed in ultimate tip # 12) when you ‘summarise’ your probe at the end (to capture everything) it’s your job to:

  • Digest
  • Interpret
  • Relay (back to your client) in words they ‘can understand.’

Takeaway: Because your client is speaking to you with ‘their own words’, you can easily find the right words, that will ensure you’re both communicating effectively and moving towards the goal quicker.

9. Inspire Creativity (it's all you!)

You can research what inspires the most creative people we know, but creativity is in ‘your hands’ – yes, it’s all you!

Be the leader (5 keys to becoming an inspirational one discussed here by Achievers) and ‘inspire creativity’ by probing about ‘alternatives’ that may seem unrealistic at first.

Because by setting expectations high (even what may be perceived as ‘unrealistic’) you and your client:

  • Encourage creativity
  • Inspire creativity
  • Get creative in your solutions.

Because whether it is:

  • Using the right ‘words’
  • Your ‘positive’ nature
  • Convincing them to like your ‘creative ideas’ (how to discussed here)

‘Creativity’ can result in better solutions that you and your client find feasible.

10. Triangulate for Completeness

The goal of your probing is completeness (with accurate answers).

Triangulate (in probing) is the process of asking related (but different questions) to achieve that completeness.

It’s an ‘art’ (as copywriting is 80% art – discussed in this top blog post).

Takeaway: If a prober has ‘doubt’ in their mind about ‘completeness’ then it’s best they back their ‘instinct’ (as discussed in the 3 golden keys to success in copywriting). Because even if it’s the smallest doubt then triangulate for completeness.

11. Give Feedback Before Offering Solutions

Although you may be tempted, don’t (when probing) come out with the solution right away.

The solution is your goal and you get your chance to be the problem-solver your client needs at the end of the probing process.

But (during the probe) respond to your client with:

  • Ideas
  • Concerns
  • Assessments
  • Data
  • More questions

To get the ‘best results’ out of the probing process, which will give you the best solution (that you and your client will agree on).

And if you’re looking for great tips on providing feedback – check out this great resource from Entrepreneur here.

But to summarise that resource (when it comes to giving feedback):

  • Create safety (by making people feel ‘comfortable’)
  • Be positive (makes recipient feel ‘open’ to a new direction)
  • Be specific (as leads to a better ‘outcome’)
  • Be immediate (human ‘brain’ learns more like this)
  • Be tough, not mean (a starting point is to get their point of ‘view’).

12. Summarise to Capture Everything

At the end of the ‘probing process’ you must summarise to:

  • Capture everything in your client’s mind (most important)
  • Capture everything in your mind (also important).

Because then, you and your client’s communication is in ‘sync’, which increases the chances of the best solution.

And while summarising is an ‘art’ (as discussed by Karen Tui Boyes here), you can master it by summing up key ideas in your own words.

Lumen ‘summarise’ how to do this (in this great resource) by asking yourself the following important questions:

  • What is the primary message I want to communicate?
  • What are the most important points that convey this message?
  • What do I want my audience to take away from this?


French anthropologist and ethnologist Claude Lévi-Strauss once said: “The scientist is not a person who gives the right answers, he’s the one who asks the right questions.” 

And you too can start asking the ‘right questions’ to your client by mastering the fundamentals of probing (by following these 12 ultimate tips) to get maximum results for any client.

Over to You…

Do you agree with the 12 Ultimate Tips to Probing in Copywriting? Or would you like to add or remove some?? Would love to hear from you in the comments – any feedback is greatly appreciated.

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