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 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.

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 broke 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 to one-day for more complex projects such as eCommerce and membership related sites.

Anything more than two days and you are turning the discovery session into a project of its own plus you will find people will start to flag or burn out.

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

Can I Hold a Discovery Session Online?

Totally, of course, you can as long as you can see the other persons face.

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.

Being able to read a person’s expressions and body language is critical to understanding how comfortable they are at answering certain questions and being able to dig a bit deeper if you hit something uncomfortable.

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.

If you are holding a remote session, try to make sure that everyone is sitting at their own computer rather than all together in a conference room. The sound is clearer, you can better read facial expressions and they will have access to your online tools such as screen share and whiteboards.

Where you hold your discovery session 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 video chat is definitely the best choice.

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!

Recanting on the previous section, don’t hold a session over the phone – it won’t work – you need to see the person to ready their body language.

Who Should Attend the Discovery Session?

Of course you and any team members who will be directly involved in the proposed project such a project manager, sales and marketing person and a developer.

From the client site, you will need the project champion.

Usually, this will be the person that initially reached out to you for the scope of work. If not, you will need somebody in the client’s business who will directly benefit from the outcome of any proposed project.

It can be useful to get client key decision-makers involved as well as any department heads that will need to do work/set up during the project such as sales & marketing or IT.

Keep the number lean though, maybe 4-5 total, otherwise you will spend more time managing people than getting information out of them.

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 and you need to be able to position the service in a way that the client can understand it’s a business benefit and not you just trying to squeeze some extra dollars from their wallet.

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 the 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.

How To Sell a Discovery Session

As mentioned above, you need to be able to position your discovery session to be of business value to the client.

Telling them they need to pay $1000 for a discovery session before you will work with them is a sure-fire way of making them hang-up on you quickly.

You should be pitching the discovery session as a piece of work that is going to save them wasted time and money in the long-run.

In your pitch, mention that the consultancy session is a way to end up with better outcomes because of a more accurate assessment of their business.

Tell them that you want to make their business better, generate more leads and make more money and by looking at the business issues surrounding their original proposal/solution they stand a better chance of achieving the outcome with less time and money.

Ask them how many other companies they approached have been willing to sit down and chat with them in-depth to really understand the problems they think their solution will solve, versus those who just came back with a time frame and a cost estimation straight up?

Without asking any detailed questions, how can they deliver the very best solution for the prospect?

Dealing With Client Kickbacks

If the prospect is still pushing back on parting money for a discovery session you could try giving a couple of analogies to help push the message across.

The two I love giving are the mechanic and the doctor.

The Mechanic Analogy

mechanic working under a car

Imagine one day you are driving around in your car and suddenly there is a strange mechanical noise coming from inside the hood.

You’ve had this car for many years and done a good job servicing it so you know it pretty well.

After poking around under the hood you think the problem is something to do with your alternator, maybe it needs a replacement.

You make a few calls to local garages asking how much it would cost to replace your car alternator and get some costs and time frames.

Choosing one (the cheapest by far!) you take the car in and get the alternator replaced.

Job is done!

A few short weeks later your car electronics short out. Disaster!!

Calling out your roadside assist company, they do a diagnosis on the car and find out that the electrical wires under the hood are old and bare causing severe short cuts which have overloaded all the system.

He sees the brand new alternator and asks why the mechanic who replaced it didn’t check the rest of the car – surely he would have discovered the corroded wiring.

You realise that you had dismissed the mechanic’s suggestion to do a comprehensive paid inspection to discover any additional issues – you told him you just wanted a new alternator.

The Doctor

doctor diagnosing a patient

If you’re ill and you go to see a doctor, does the doctor take your word for what you think may be wrong with you?

Definitely not!

The doctor performs their own diagnosis to make sure that the solution (medication) they give you will have the best chance at making you better (solving all your problems).

If the doctor gives you treatment for what you think is wrong it is likely to make things a lot worse.

Turn it on its head and you get the same result.

Would you trust a doctor that gave your child medication without performing a comprehensive examination on them and asking extensive questions about their condition?

Hint: that’s what we do in a paid discovery session – we want to give you the very best solution to the problems you have and even those you weren’t currently aware of!

Selling A Paid Discovery Session

You need to overcome the objections from the prospect and show them how much business benefit they will receive from a paid discovery session. Specifically answering these questions:

  • What is a discovery session?
  • What is the benefit of a discovery session?
  • What happens after discovery?
  • What do they get from the session?
  • How long is it and who’s involved?
  • Where does it take place?
  • How much is it?
  • When can they do it?

Upselling A Paid Discovery Session Email Template

Here is an email template that you can use and tweak for your own business to send to a prospect after an initial meeting or chat, upselling the benefits of a paid discovery session.

Hi [Propects Name]

It was great to chat with you [yesterday/the other day] and I’m confident that we can help you [solve their problem].

The next step we should take is to schedule a discovery session.

A discovery session is a deep dive into your business to examine the problems you’re facing and gain a shared understanding of what success looks like to you.

The discovery session will allow us to plot a course forward and find out the quickest, most effective and least risky way to solve [the problem they are having].

After the session, you’ll receive a PDF report which includes the detailed requirements of the proposed project, potential risks and how to avoid those and an action plan to get your business from where it is now to where you would like it to be.

The discovery session is a [length of session] meeting [on zoom/at the location] with myself and you along with any other key business representatives who need to be involved in the conception of the project.

The cost for the session is $[X].

Below are some potential dates for a discovery session according to my availability. Please let me know which date works best for you so that we can get the ball rolling.

  • [Date and Time 1]
  • [Date and Time 2]
  • [Date and Time 3]


[Your Name]

How Much Should I Charge For a Discovery Session?

I get asked this question a lot.

As a general rule of thumb, I charge between 5% to 10% of the overall perceived project value which you have already asked the client when pre-qualifying them.

So, if the prospect has indicated that they are budgeting a piece of work up to $40,000 then you could charge them between $2,000 and $4,000 for the discovery session.

Of course, you may not know exactly how much the end project is going to cost until you do the discovery session so that may be a bit of a chicken and egg for you at the beginning, or your client may still be a bit cagey over their overall budget commitment.

You could sell a discovery session at an hourly rate, so a 4-hour session (1/2 day) at an hourly rate of $200 would come out at a cost of $800.

What Deliverables Are Sent At the End of a Discovery Session?

The actual deliverable is up to you, however, it should ideally be some type of unmodifiable report such as a PDF.

The key component of the report is that the prospect can take it to any other designer/developer to kick off the project.

I know that sounds a bit dumb at first. Why would you want to let a prospective client go?

But it’s a mindset that you have to get over. A paid discovery session is a stand-alone body of work.

Yes, you did the work and delivered the report, but the prospect can choose to go to another provider. That’s their choice.

However, experience has shown that 98% of the time, the personal relationship that you have built with the people coupled with your now deep understanding of their business and issues is more than enough to win you the contract.

At a minimum, your report should include the following:

  • The original brief
  • Why this piece of work was undertaken
  • What is in and out of scope
  • Who has been involved – names, positions/responsibilities
  • Stakeholder’s goals and priorities
  • Industry and competitor analysis (if relevant)
  • Problems, solutions, costs and timescales – in-depth but in components
  • Roadmap from start to finish to implement solutions
  • Total cost and payment plan
  • Here’s what you need to do next


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?

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

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