Live demos are simultaneously the best and worst ways of selling your product. When they go well, demos join the dots for the buyer, making it easy to buy. When they go badly, they can cannibalise hard-won goodwill. The good news is that killer software demos are all about planning, practice and presentation (plus a sprinkling of personality).

These are our tips from buy and sell-side perspectives on what makes or breaks a legaltech demo, and how to demo legaltech (or any tech) like a pro.

1. What to demo

Demo relevant

Assuming you spent time before the meeting and at the start of the meeting qualifying your buyer’s needs, demo only to those needs. Do not follow the same old script that rushes through any and all features and use cases.

Buyers hate a boring checklist style demo of feature, after feature, after feature with no demonstrable value beyond quantity or cleverness of features. Focus on quality, not quantity.

Be specific. Frame your demo within the identified prospect need or problem. Why? It reinforces that you’ve listened, taken the time to understand the buyer and their needs. Furthermore, it makes it easier to join the dots between what the buyer needs and what you provide to fill that gap. The easier it is to join those dots, the better the demo’s persuasive power and influence. Specific examples of how to do this are set out below.

Demo well

Never work with children, animals or technology. Several of us at lawtomated demo many times a week, sometimes several times a day. We also demo to external and internal “buyers”. Something more or less always goes wrong. The small stuff is kind of an accepted cost of demoing, e.g. having the wrong or missing cables to connect to a display. But there is also a plethora of inexcusable and avoidable faux pas.

Here’s our tips for killer software demos:

Do this:

  1. Be prepared. Have a list of targeted features, use cases and benefits that map to the identified needs of the prospect. Focus on these, the buyer’s questions and nothing else. Just because you could demo something, doesn’t mean you should if it is wholly inapplicable and distracts from your narrative and why it’s relevant to the buyer.
  2. Invite questions, but don’t be afraid to put a pin in them if you are about to answer that question or just coming to a feature or use case that will answer the question. Don’t lose your flow. The more “all over the place” the demo, the easier it is to wrongly infer the product is similarly dysfunctional.
  3. Use data relevant to your prospect. If you are an AI contract review vendor, build demos that simulate real world – as opposed to esoteric or make-believe scenarios – and better still, prove they work scalably. For instance, extracting a clause from two or three virtually identical documents with very well signposted clauses is not impressive. Doing that across 10s (or better still, 100s…) of very different documents is impressive. If you can prove performance on a sight unseen document introduced by the buyer at the meeting you will get the cheque right there and then… sadly that hasn’t happened yet! The point is this: make sure your tech isn’t a merely clever toy, but is instead a scalable product that works in real world scenarios and not just contrived situations.
  4. Don’t forget the basics. To continue the AI example, the real challenge that these tools try to solve is maintaining quality and consistency of legal review through technology in the face of ever mounting quantities and complexities of legal issues. If your tool doesn’t have, or you don’t demo, the necessary collaboration features to enable a team of users to work efficiently then your demo will be cool but ultimately impractical. Sadly this is all too often the case with legaltech.
  5. Know who’s in the room. Weaponise this information – use it to help you target your demo content and patter. If you can, identify who are the decision-makers, research them beforehand and demonstrate your understanding of their role and their work, ideally also how your product solves their need. Engage them throughout the meeting with questions to confirm and curate their understanding of your product and how it solves their need.
  6. Know your tech. Ideally know your tech inside out, in particular basics regarding how it is hosted, delivered, manages data and the core technologies and integrations it includes. If you don’t know the answer, acknowledge this fact but immediately promise to find out the answer and report back promptly. Simply saying “I don’t know” and moving on, or dodging the question, looks terrible. It goes without saying, but don’t lie.
  7. Demo tested product. Make sure the version you are demoing has been tested… too often, speaking from experience, releases are pushed onto demo sites without proper testing. Don’t get caught short. It looks terrible.
  8. Explore concerns. Use the demo to dive deeper into understanding the buyer’s needs and wants. Try to get ahead of objections by anticipating them beforehand and having demo content and patter that tackles these concerns constructively.

Don’t do this:

  1. Being totally unprepared for obvious questions about your product and / or its fit to your buyer’s needs. It looks awful and suggests you don’t care.
  2. Having the wrong person demo. Don’t send your most technical person to demo to lawyers or business users unless they do so regularly. Likewise, don’t send your least technical salesperson to demo to a technical audience. it always fails and fails hard.
  3. Skirting around obvious issues with the product… you may not think it’s obvious but it almost always is. If something in your demo environment is down or not quite fixed, be upfront. Don’t try and polish a turd. Sooner or later it starts to smell. Rolling it in glittery patter doesn’t help either.
  4. Have your technical team updating the demo environment. Demos going slow or offline is never a great look. Be sensible and plan maintenance, upgrades and migrations outside of your and your prospects’ business hours.
  5. Have a single demo environment that multiple sales / presales people use simultaneously. This happens rather a lot. It looks awful if you’re midway through a demonstration only for the background data in the app to disappear or change completely because your colleague is interacting with the same environment. It’s pretty basic and creates an impression of disorganisation and poor design.
  6. Window / tab switching. Sometimes this is inevitable if your app communicates with other apps and services. If so, ignore this point. However, often vendors run jaunty demos flipping back and forth between multiple tabs and windows to demo features located in different demo versions. This is super distracting and totally spoils the narrative thread of your demo. It can also create a sense the product is at worst fake, or at best half baked. You should avoid creating either impression. Where possible, keep things within the one window.

Remember, we are looking for a partner, not a vendor. This is about trust. Build it from the beginning and things are a lot easier. Your demo is often a large part of early impressions. Being able to deliver killer software demos repeatedly to wider stakeholders will set you apart from the competition.

Demo what you have, not what you hope to have

There has always been, and no doubt always will be, a gulf between your demo and your product. That’s sales. That’s marketing. That’s tech. This holds true for the little players as it does for the big boys. If what you’re demoing is something hacked together an hour before, the night before or the weekend before your meeting… please, please do not demo it. The buyer will find out sooner or later it’s BS. Remember you need to make the buyer look good, not bad. Tricking buyers into believing you have products or features you don’t (or worse won’t) have is only going to backfire and kill your prospects rather than ensure killer software demos.

Worse, legaltech is a village. Sooner or later word gets around about the honest vendors vs. the loose and fast.

Which do you want to be?

The exception that proves the rule…

The only caveat to this is if you are either:

  1. being asked to demo a minimum viable product or prototypes from your future roadmap; or
  2. have been asked to build something bespoke to demonstrate your stretch capabilities.

In which case, demoing potential rather than the here and now might be welcome and an additional route to killer software demos. That said, in either case, be honest about the assumptions and qualifications involved. If what you’ve built can’t scale, or won’t scale without significant R&D or hardware, be honest and open about those concerns.

2. Who to bring

Opposites don’t attract

Provided you’ve done your homework beforehand, you should know who your audience will be. Generally speaking, try to match the audience to your team’s skills and experience. For instance:


Who to bring

1. 100% IT

A. Your best IT people who know the product inside and out. If the buyer-side IT include deep specialists in areas such as data science, machine learning or cyber security then bring your own experts in these fields to the extent you have them. Don’t let sales answer technical questions… or data science questions… it is invariably misjudged.

2. 100% legal / busines persons

B. Your sales and presales team plus subject matter experts (if any). Some legaltech vendors employ former lawyers specifically as subject matter experts, i.e. to talk lawyer to lawyers, build trust, demonstrate understanding and identify and qualify scope of needs and product fit.
3. A mix of 1 and 2 A mix of A and B.

Where you bring a mix of sales and technical people to the meeting, be sure to have created a culture of mutual respect and trust in your team. Let technical people answer technical questions and salespeople answer sales questions. You each bring something unique and valuable to the table – recognise and respect that.

Try to collaborate beforehand to agree the demo strategy, focus and likely objections and how best to respond to each.

We set out below a cautionary tale in the context of Slido where this went farcically awry.

Your best self

It can be extremely boring and forced demoing similar demos one after another, as is often the case in sales and presales. Try to be high energy, friendly and genuinely curious about your prospect. Doing so will create a positive feedback loop within yourself, but also between yourself and the buyer.

3. What to bring


Cables. Cables. Cables. First impressions matter and everyone, whether buyer or seller, hates the awkward and seemingly inevitable pantomime of finding the right cable to connect vendor laptops to buyer meeting room displays.

Yes, buyers should have their proverbial together, but often cables are lost or accidentally taken home from meeting rooms.

It costs very little to buy and maintain your own stash of the most popular cable connections, certainly much less than the cost of a lost deal.

Make sure all of your sales and presales (or anyone who is demoing) has at least these types of cables and / or adapters:

  1. HDMI
  2. DVI
  3. VGA
  4. Displayport

Your charger

Believe it or not, it does happen. Vendors sometimes turn up with a dead, or close to dead laptop and no charger. If you are selling to legal users they expect not only your product, but your individuals to be a safe pair of hands.

Turning up so ill-prepared never looks good.

Apart from anything, your demo will be rushed due to battery life paranoia, or worse, impossible should your laptop die mid demo.

4. Conference calls

Plan ahead

Make sure you are 100% clear regarding:

  1. The attendees, and ensuring everyone who should attend has been sent the correct diary invite and dial-in details.
  2. The dial-in format – is it audio, video or audiovisual? Make sure you are set-up beforehand to deal with whatever format is required, including having the necessary hardware, software and / or settings configured, tested and ready to go 5- 10 mins before the call starts.
  3. What provider is being used? Webex, Zoom, GoToMeeting etc? Have you used them before – did they work? If not, try suggesting an alternative beforehand.
  4. The time and date, including the timezone. Too often diary invites are sent out for the wrong time due to a timezone misunderstanding. Getting this wrong demonstrates a lack of attention to detail, nor understanding of the buyer’s business.

The above sounds obvious, but too often come together to derail any chance of delivering killer software demos.

Be somewhere connected and quiet

This ought to go without saying, but sadly it doesn’t. Whilst buyers appreciate vendors are often moving around clients and prospects, it’s no excuse to take a conference call somewhere noisy and / or with woeful internet connectivity. If you can’t make the call in proper surrounds try to rearrange as early as possible.

A poor quality or noisy connection isn’t worth the effort.

Be on time

Don’t be late. Treat this exactly like a physical meeting. Too frequently vendors turn up late, or on the dot, yet aren’t set-up to begin the call at the stated time. Just because it’s a conference call doesn’t mean it’s any less important to get the basic stuff right.

Pay attention

It’s all too easy to go on your phone, scroll around on your device whilst the recipient audience is talking. Don’t do this. It’s obvious and you look dumb, especially if the buyer asks a question that you don’t hear.

5. Conferences & Events

They are no different

All of the above applies to conferences and events. This applies regardless of whether the conference or event is hosted by the vendor or third parties.

Slippery Slido

In recent years Slido has become very popular at events and conferences. It’s an app that works on any device and lets participants:

  • ask and answer questions; and
  • vote in polls.

In each case, the feedback is live, i.e. real-time. This can be great to get instant feedback from an audience of their opinion on a key theme, topic, question or your product, presentation or pitch. But use it at your peril.

At lawtomated we can recall a toe-curling scene that wouldn’t have been out of place in an episode of The Office, The Thick of It or Silicon Valley:

  • At a packed event before circa 100 financial services professionals, including senior regional heads of IT and data science, during a presentation, the presenting vendor of an AI solution asked the audience “Based on what you’ve heard, would you buy X product?”.
  • After the initial presentation, votes for “Yes” were bumping around 85%. Great result.
  • However, shortly into the Q&A a bombastic salesperson suffering from the Dunning-Kruger effect kept jumping in answering extremely technical questions asked by the very senior data science leaders seated in the front row.
  • Unfortunately, the answers provided were at best inaccurate, and at worst, misleading. As each answer was given, the Slido score tumbled toward 45% and finished up around 10% by the end of the Q&A.
  • The worst part was that the Slido results were up on a big screen behind the presenters for all to see… not the best result, but a reminder of the points made above regarding who to bring. If you can’t answer a question, don’t bluff and bluster – it doesn’t work unless, except perhaps in today’s US and UK politics.

Avoiding the above will ensure you have killer software demos at conferences, untarnished by poor stage management of Slido polling.


Be prepared, be relevant and be your best self. Know your audience and match them with equivalent expertise able to ask and answer appropriate questions where needed. If you do so, you’ll deliver killer software demos!

Ensure your demo environment is running, not subject to maintenance and actually available when you need to demo.

The more precisely you can match your demo to your prospects needs the easier it is for them to join the dots and sell your solution to themselves and to their stakeholders. If your demo can prove a ROI, even in limited circumstances, it will make things much easier and more impactful, increasing your ability to nail killer software demos that persuades.

Last of all, don’t fake it or half-bake it. Demo only what you have, and not what you wish you had.

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