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How to Run a Discovery Session to Get to Know Your Clients Quickly

A discovery session allows you to zoom out and look at the bigger picture before dealing with the nitty-gritty details.

It also allows you to understand the business context, operations, audiences and marketing techniques uses allowing you to find value-adds.

All this helps you to write a custom proposal which is more likely to be accepted.

What is a Discovery Session?

The goal of a discovery session is to ask your client lots of questions about the piece of work they think they need and listen to their answers.

It’s your job to get a good understanding of the issues and pain points they have leading up to them contacting you.

The ultimate takeaway from a discovery session is a clear understanding of the client’s business needs now and in the foreseeable future in the form or an achievable roadmap document/proposal setting out goals, milestones, actions, schedules and costs.

If your discovery session is great, the client should be able to take the outcome document to any designer, developer, consultant or agency allowing them to jump-start right into the project.

We kinda want the client to go with us though!

What to Include in the Discovery Session

Be prepared to ask a lot of questions, some uncomfortable for the client with awkward pauses.

You will need to do a deep dive on their business and the reasons why they think this work is needed.

Warning: most discovery sessions will uncover a whole heap of issues and questions the client had never thought of and may not even have answers for.

Essential Questions to Ask in a Discovery Session


You should find many more questions to ask at a discovery workshop but here are what I think are the essential ones.

What Are Their Main Target Audiences?

Demographics, ages, geolocation, habits, etc.

You want to knuckle down in this area and explore their target audience in as much detail as you can.

Who Are Their Main Competitors?

So that you can analyse how they are selling to the same audience.

What is the Budget For This Work?

Don’t work for free and make sure the client is willing to spend.

What are the Timescales?

You need to know the urgency of this work.

Why They Need This Done?

This is the nitty-gritty of the session – why do they need this work done.

You may find that the reason is something your client didn’t realise at the onset of commissioning the session!

That’s good – best to find out now than half-way through the project.

What is Their Biggest Pain Point Right Now?

A big win-win for you if you can nail and sell a solution to that issue.

What Would the World Look Like if the Above Was Fixed?

Get your client to tell you what goals reached would make them happy.

They are writing their own proposal for you!!

What Did They Try Before? What Worked and What Didn’t?

If it ‘ain’t broken don’t fix it! Conversely, don’t gift wrap a turd!

Here is a good opportunity to find out what marketing campaigns they have tried before.

What is Their Customer Lifetime Value?

The Customer Lifetime Value (CLV or CLTV) is the amount of money your client gets from selling their stuff to one of their customers over many years including repeat buying.

What are Their Business Goals Now, 1, 2, 5+ Years?

Where is the business heading now and in the future – make sure your solution is future proof.

What Areas of the Business Are Underperforming?

Perhaps not directly related to the initial reason for the workshop but it could give your proposal the edge in solving any current business issues like saving time and money.

It’s worth asking!

What Does Success Mean?

Get the client to paint a picture of what their ideal business world would look like,

Sometimes it’s worth looking at the end picture and exploring how to get there by working your way backwards.


A small but powerful word when used correctly.

Keep diving deep by asking your client “why” when something they say isn’t obvious to you.

It will make for some uncomfortable pauses and silences.

It will also unlock gold for your proposal!

How Long Should a Discovery Session Last?

That is a difficult question to answer as it really depends on the size and scope of the perceived project.

I tell clients to free up at least 2 hours minimum, ideally a half-day for more complex projects such as eCommerce and membership related sites.

Anything more than a day and you are turning the discovery session into a project of its own.

Time to plan on breaking that sucker into multiple deliverable projects.

Can I Hold a Discovery Session Online?

Totally, of course, you can.

It really depends on how you work, where the client is located and how prepared you are.

Some people prefer face-to-face on-site sessions and that’s fine for local clients.

Unless interstate or international clients are prepared to pay your travel and accommodation costs, online is definitely the best choice.

If you are planning on holding an online discovery session, I would highly recommend using a visual communications tool such as Zoom or Skype so that you can see the client’s face and posture.

You will find that being able to read body language signals during discovery sessions will become invaluable in understanding the client’s answers.

I often find that in asking questions around money and personal commitments, the client will tell me one thing but their body language will hint at something else or prompt me to ask more leading questions.

Where Not to Hold a Discovery Session

I realise that some of you will be new to this and perhaps new to running a business, however, that being said, you still need to appear professional.

If you are meeting a client face-to-face IRL (in real life), suggest their office space where they will feel more comfortable.

Otherwise, you can rent out a room from a co-working space for a few tens of dollars per hour.

Don’t do noisy public spaces like coffee shops, regardless of how good their coffee is!

Can I Charge for the Discovery Session Workshop?

Absolutely yes!

You need your client to be in “Buy Mode” at the top of your sales funnel or prospect pyramid to sell them a discovery session.

Otherwise, if they are not in “Buy Mode” they will not perceive your solution as something they see value in and/or need.

It’s your judgement call and qualification questions you ask the client or prospect that will determine whether they will be willing to spend the time and money on a paid discovery session.

What is the Difference Between a Session and a Workshop?

It’s really in the semantics, the meaning.

I use the two terms interchangeably but regard the time as a workshop because both yourself and the client should be working together, exploring and bouncing ideas and facts off each other.


From all the information you have gathered at the discovery session, you should have a good idea on which key areas to focus your proposal on.

This may include a website redesign, a new social media strategy, integration with third-party systems, marketing and PPC campaigns and new web content.

Writing a winning proposal sounds like a title for another blog post. Stay tuned!

Let me know in the comments below what other great questions you ask at a discovery workshop?

Keep In Touch


Wil is a dad, consultant, developer, conference organiser, speaker and business mentor. He co-organizes the WordPress Sydney meetup group and has been on the orgnising committee for WordCamp Sydney since 2014. He speaks at many technical events and contributes to the WordPress open source project. His likes are chillies, craft beer and electrogravitics.

1 thought on “How to Run a Discovery Session to Get to Know Your Clients Quickly”

  1. Pingback: The Differences Between Cost-Based Pricing & Value-Based Pricing

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