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Demo Fails: How to Turn Challenges Into Triumphs

Sam Hillestad
Director of Product Marketing
Same Hillestad Session

Table of Contents

    At last week’s Demos Reimagined, a lively panel of Solutions Engineers had a candid discussion on their biggest “demo fails.” Panelists from Qualtrics, Codat, Black Kite, and HubSpot shared stories of demos gone wrong, but more importantly, how they recovered and turned them into learning experiences.

    The key takeaway? Demo fails are often not nearly as bad as we think they are. There are also some easy ways to recover in the moment, and some best practices to avoid them altogether moving forward. Let’s dive in!

    Top Demo Fails

    The panelist shared a wide range of demo fails, spanning from the mundane to the embarrassing. Here are some of the most notable fails shared:

    1. Manually setting up a demo environment — then expecting reps to do the same
    2. Laggy or buggy product leaving a bad impression
    3. WiFi outages or difficulty connecting to a new network
    4. Having your environment reset mid-demo
    5. Unresponsive prospects and awkward silences
    6. Unwanted Slack notifications appearing

    Lessons Learned

    The good news about demo fails? You can learn from your mistakes!

    The panel discussed the top ways to manage demo mishaps in the moment, as well as strategies to avoid future demos fails altogether. Here are their top lessons learned:

    1. Take a breath

    One of the top pieces of advice was “don’t sweat the small stuff.” The panelists, especially Maria Lat, reminded us that demo fails are rarely as bad as you think they are. Your first reaction might be to panic and apologize profusely. Instead, the panel agreed that it’s okay to take a beat and regroup. More often than not, you can just carry on like nothing happened, and odds are the prospect either didn’t notice or didn’t care. And when in doubt, blame the WiFi!

    2. Use mishaps to build rapport

    Matthew James and the panel agreed that demo fails are often not that bad — they can even be helpful! You can easily laugh off minor hiccups, or even call attention to them. Your prospect has probably faced similar challenges, and you can bond over it. Even embarrassing accidents can be humanizing and memorable in ways that can actually help the deal! Leaning into your failures can also be a sign of confidence.

    3. Don’t demo selfishly

    Another shared lesson from the panel was around the need for interactivity. Kalyan Ramkumar impressed upon us that instead of showing how smart you are and how amazing your product is, talk to your prospect like a human. Understand their problem. Ask questions. Go slow, and change what you’re showing based on what the prospect is telling you. Alex Nation summed it up with some of the best professional advice she ever received: “Don’t demo selfishly.”

    4. Lean on specialized demo software to make your environment fail-proof

    Slow load times, bugs, unexpected product changes, and unreliable demo environments were all hot topics. The panel talked about ways to handle those challenges in the moment, but they also acknowledged there are technological improvements that can avoid those mishaps altogether. For instance, creating a clone of your app in a self-contained demo environment can make demos much more repeatable and dependable. It can also help you scale. Instead of cloning and resetting demos, you can send your reps a single link that will work for everyone, every time.

    5. Lean on specialized demo software to automate manual processes

    Moderator Sam Hillestad shared a different kind of demo fail: asking reps for manual work led to a lack of adoption. This was unsurprising in retrospect. Reps have limited time, and they shouldn’t be spending that on unnecessary manual processes. Instead, the panel discussed ways that modern demo software can automate this manual work. For instance, specialized demo software can inject a demo environment with custom datasets. Instead of having reps create their own instance and manually add data themselves, they can populate a demo with data in just a few clicks.

    Tips for Making Demos Failure-Proof

    The panelists left us with some practical advice for proactively reducing demo issues and creating a resilient experience:

    ✅ Practice makes perfect: Just like you’d never perform on stage without doing a dry run, you shouldn’t be flying blind into prospect demos. Especially when heading into a high-stakes meeting, ask someone outside your usual team to sit in on your dry run for a fresh perspective.

    ✅ Pre-record demo flows: The panelists suggested capturing screenshots or recording flows to gather internal feedback, especially when crafting leave-behind assets.

    ✅ Make it a collaborative effort: Build strong relationships with account executives so demos happen in sync; the AE can help emphasize key points and ask pertinent questions to reinforce your story.

    ✅ Think of the demo as a journey, not a one-stop-shop. Supplement your live interactions with other assets, like interactive tours or leave-behind materials to reinforce key messages, dive into specific features, and leave a lasting impression. A short, recorded demo or tour can even be sent before the meeting, allowing prospects to preview the product and share questions in advance. This also alleviates the feeling that your live demo needs to be perfect; It’s just one touchpoint in a broad experience.

    Final Takeaway: Let Demo Setbacks Humanize the Experience

    As the Demos Reimagined panel showed, even with the best preparation, unexpected demo issues happen. And in a world full of bots and automations, people appreciate the mistakes and authenticity of human interactions. So when mishaps occur, accept that you’re human and lean into it.

    • Stay cool, calm, and collected — In the midst of a tech glitch, laugh it off or use humor to buy a moment to troubleshoot. Your prospects will probably have empathy for you, and you might leave a more memorable impression on them.
    • Be honest and humble — If a question stumps you, calmly admit that you’ll follow up. This honesty builds trust and reassures the customer that their needs come first.
    • Prioritize your prospect — When things don’t go perfectly, embrace the opportunity to show flexibility, adaptability, and empathy for your prospects’ experience.

    What matters most? Your ability to respond to your prospects’ needs and learn from mistakes, so each demo is better than the last.

     

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