I never like to sell technology or push technology. What I like to do is educate people about technology and alongside the implementation of a solution, be it WorkGuru or something else, what you’re selling is relief, resilience, a smoother way to keep doing what’s already been done, and possibly sleep, restful sleep.

If you’re a young adult listening, your job is not to win the argument. It’s to run a small experiment that makes the owner’s life easier while protecting the business that they’ve worked so hard to build. And if you’re the parent who’s running a family business, listening may open up the opportunity of trying one small thing without signing up for a total overhaul, without signing up for handing over the keys.

– Heather Smith

In this episode of the Accounting Apps Podcast, I explore a situation that comes up often in family businesses. The younger generation can see the benefits of modern systems, but the parents who built the business may be reluctant to change. It is easy to assume the conversation is about software features, but in reality it is often about identity, control, risk and pride. The business represents years of effort and success, so changing systems can feel personal.

I share some practical ways to approach these conversations with respect and patience. Rather than pushing a full technology overhaul, I suggest starting with a small, low risk experiment using what I call a “tiny pilot”. By solving one annoying problem and making the change reversible, you can build trust and show the benefits of modern tools without disrupting the foundations of the business.

This was inspired by a LinkedIn post from Tony Harcourt.

Key discussion points:

• The generational technology gap in family businesses
• Emotional drivers behind software resistance: identity, control, pride, risk
• Insights from Xero’s behavioural research on tech adoption
• Why trust and communication shape innovation success
• The “Tiny Pilot” method for low-risk digital change
• Practical scripts to reduce defensiveness and build collaboration
• Handling common objections like “It’s too expensive” or “We’ve always done it this way”
• The role of external advisors in supporting family dynamics

Key Takeaway:

Successful technology adoption in family businesses is about protecting legacy while reducing friction. Start small, make it reversible, and focus on outcomes, not features. 

Contact details: 

Tony Harcourt: https://www.linkedin.com/in/tony-harcourt/ 

LinkedIn Post: https://www.linkedin.com/feed/update/urn:li:activity:7432901025231159296/ 

WorkGuru https://workguru.io/ 

Behavioural Research by Xero: https://www.xero.com/au/media-releases/behavioural-research-by-xero-uncovers-barriers-for-au-small-businesses/ 

Scroll down for a full transcript (AI-generated transcript)

Today’s episode is inspired by a LinkedIn post from Tony Harcourt, who is the co founder of WorkGuru.io. Now, in his post, which I’ll put a link to it in the show notes. I’m just going to read you a sort of a small extraction of his post.

He’s talking about the son of a business owner who is desperate to move a family business onto modern system, but the older generation won’t have a bar of it, because they’ve always done it that way, because pen and paper works just as well, because it doesn’t work, and they’re bleeding money and the son count can see it, but he can’t make the decision. He’s not in the position to make the decision.

So as I mentioned, Tony Harcourt is the co-founder of WorkGuru. WorkGuru is an Australian cloud-based job-management and inventory software platform. It’s designed for product-based and project-based businesses, so commonly used by manufacturers, wholesalers, importers, field service businesses, installers and trade based businesses. Now I tell you that because you can understand it’s sort of it’s a big, impressive system, and I imagine Tony has come up against that situation, scenario multiple times as have I through my implementations.

I thought it would be useful to talk about this scenario that maybe you too have experienced young adult wants to help parents modernise the business. The parents have run it successfully for years, possibly decades. So from their perspective, the business itself is proof that the current way works. And so what needs to happen here is we need to influence them to make a decision on the technology. Now, I actually never like to sell technology or push technology. What I like to do is educate people about technology and alongside the implementation of a solution, be it WorkGuru or something else, what you’re selling is relief, resilience, a smoother way to keep doing what’s already been done, and possibly sleep, restful sleep. And you’re possibly building in capacity and tracking those profits, and you know, really hoping that you’re building in profit into that implementation.

But it gets emotional. It astonishes me, in fact, how emotional the purchase of software can actually be. And I sometimes say to people, when they’re trying to move someone off one system onto another system, you’re they’re almost married to that system, and you’re asking them to divorce that system. And we all know that people stay in marriages longer than they necessarily should, and to go through that divorce and to separate from their system to another system is emotional. So the technology is not necessarily the features and functionalities of the technology is not necessarily the conversations that need to be had.

Why the scenario is challenging? It’s identity. The business represents me. I built this business. It represents me. It is part of me. I am the fabric of this business. Control. If I let you change something, am I going to lose grip on the business? If I let you do something and change the workflow, am I going to understand it? Do I need to understand it? Am I going to understand it? Will I get lost if I need to do something risk, what if it breaks? What if it doesn’t work? We all hear about implementations that go wrong, what if it doesn’t work? And there’s also sort of along with identity, pride. Are you saying I’ve been doing it wrong? Are you saying that there was a better way that I should have adopted a decade ago? Are you saying that I don’t know what I’m doing? I do. I’m making money. I’m turning up to work every day. I’m working hard, I’m employing people.

So it is really far more than, than, than, sort of, if you’re coming into this new the behavioural piece is really important. Now, Xero actually released a behavioural research on this back in 2021 and I’ll pop a link into the research notes that they have, and they found in that that the biggest hurdle was not actually information, but anxiety around the complexity and the sort of the final cost of the solutions. I thought that that was interesting. So let me just small businesses in Australia tended to put off technology decisions if confronted with too many options, six out of 10 agreed with that, or because the decision doesn’t feel urgent, seven out of 10 agreed with that. And I think that that’s playing into the family business scenario. They feel reluctant about changing things they’ve done. They’ve been doing since day one. Six out of 10, I’m agreed with that, and they lack confidence in getting support they need for beneficial new technology from from leaders. So seven out of 10 felt that. So that’s kind of an interesting research to refer to, and I’ll put sort of notes in in the show show notes there for you.

It’s about a key thing here is respect, and another key thing here is reducing that perceived risk now, and maybe I’ve just been to a workshop on how different generations communicate, and I thought that it would be good to sort of bring that into the conversation. Because, of course, if you’ve got a parent and a child scenario, they communicate in different ways. So different generations communicate and deal with change through different defaults, which can create friction, even when everyone is trying to do the right thing. So the older generations and look, I’m 56 I’m old. So the older generations tend to value experience, face to face conversations, and calm considered pace, and they often prefer decisions that feel proven, that feel low risk and that feel practical. Whereas the younger generation are usually more comfortable with fast feedback, messaging, messaging, so direct messaging, Slack messaging, that sort of messaging, experimenting in smaller iterations, and they’re more likely to see change as a normal part of work, rather than a disruption.

Put those together, and you get classic misunderstandings. One side hears, we should try this new tool, and translates it to it as what we’ve done isn’t good enough, while the other side hears we don’t need that, and translates it as I’m not being listened to. And so sometimes it might sometimes the fix may be to slow the conversation down, to agree on goals first, and to make small steps that are reversible, so small iterations move forward in small iterations. So what are the levers that actually move a longtime owner so they want to protect what they’ve built? So position the text as an insurance policy for the business. It provides backups. It provides security and less single point of failures, remove one reoccurring annoyance, choose one pain that they already complain about. They must be complaining about something. What is something they complain about? Is it delaying and invoicing? Is it stock areas? Is it job tracking. Is it finding documents? Is it payroll stress? Find something that they already stress over, and see if that’s something that you can solve. And as I mentioned before, make the change reversible. If they believe they can stop without damage, they’re far more likely to start. So this ties to another point from sort of family business research, if trust and communication are low, innovation simply doesn’t stick.

So I’m going to link to another article that refers to low trust, resistance to change and intergenerational communication. Gaps can prevent. Use strategies and collaboration from taking root, and that’s from a publication called Family business.org So yes, you’re implementing software, but you’re also managing family dynamics. So there’s a method called the tiny pilot. We have the copilot. Let’s talk about the tiny pilot. Look at it and pick one workflow, so one, not five, just pick one and set a short trial window. So four weeks is enough to usually see if you’re going to get wins, but feel short enough to feel safe. So set a short trial window and define what’s going to happen in really plain English. Don’t use the technical terms. Put it in real layman terms, what’s going to happen. So invoices are going to go out on the same day, or less time is going to be spent on admin after hours, or there will be faster cash collection. Very, very simple, straightforward. What are the outcomes here? And set the young adult up as support. The parent only needs to use it, the support and refer to the support as they need it, but the young adult focuses on being the support process here.

This reduces the cognitive load on the business owner, this reduces the cognitive load on the elder business owner, and it keeps their dignity intact. So one of the things when we talk like this, it’s, I encourage you to sort of do some research, but use the word so I’m going to share some words with you that awesome lines with you, feel free to use them, but also have conversations. Tony Harcourtalways up on LinkedIn and in the community group, so you can always sort of communicate with him.

How does he influence the older generation? So here are a few lines that work. They’re respectful, they’re specific. You’ve built a business that works. So I’m not here to change that. I want to shrink the annoying bits. Can we try one small change for four weeks and it’s if it’s not better, we can stop. If this saves you even one hour a week, what would you do with that time? And that’s a really good one. What would you do if I gave you one hour a week of extra time, and you might even want to encourage them to to look at golf, to look at travel, to look at getting home to their grandchildren. Let’s choose the option with the least disruption. Let’s choose the option that’s going to be easiest to implement but doesn’t have the fanciest of features. Oh, went fancy. Ah, that’s my English Heritage coming out, isn’t it? So let’s choose the option with the least disruption.

So when you have technology in a business, there are some small things that you can implement, and once you just get used to them, you don’t even know that they’re there. But, but we want to, we don’t we want to have we want to build trust, and we want to see benefits from that. And so with that, there are going to be some common objections. And so let’s think of the common objections, and then think of some practical responses to that. So common objections were, it’s too expensive. Well, look at something that is the cheapest, high impact tool, and see how, how that goes in the small, the micro, small, medium sized business. A lot of the software is really reasonably priced. So, you know, look around, and sometimes it’s a matter of parts can be implemented and sort of you can build on them. So start with the cheapest, high impact tool. It will be too hard to learn. So help them with the setup. Don’t, don’t get the business owner necessary to involve with the the the work of setting up, but teach them how to use it. Focus on how to use it. The actual setup can be really. Hard so get experts in for that bit and teach them how to use it. We tried the software once, and it was a nightmare. Goodness. I’ve heard that statement so many times. When did you try it? Was it a decade ago? Did you have proper training in it? Did someone come in who knew how it should work? Set it up for you.

Acknowledge that, yes, yes, I hear that, but then reframe it perhaps as a process, problem. Pilot, one of the workflows, not, not fully, fully roll out the whole system. Pilot, part of it and work on training, training, training, training, everything I focus on, all of my education, is around training. And then the common objection of, we’ve always done it this way, and to respond to that, well, you’ve always done it this way. What’s one part that you’d happily never do again, and yeah, see what their response is, and build up from that that’s kind of a matter of refining. What do they secretly hate doing? What’s one admin task that they, as long term business owners secretly hate doing but they’ve just normalised one thing that I secretly hated. I didn’t even know I hated it. Actually, no, I’m going to say I didn’t know I hated it. But installing software from from floppy, not floppy disk. What do we call them? Those installing software upgrades. And I didn’t know I hated it until I never had to do it again. And then, oh, my goodness, when a client who needed a manual upgrade doing I just didn’t, didn’t want to work with that. So yeah, installing upgrades did become normalised, and not having to do that is a good thing.

Also, have they asked them if there’s any small piece of technology improvements they’ve seen over time that that have have actually helped them in their business, talk to them about that, has anything improved the way that they operate and that they’re actually enjoying so highlighting that, one of the things I always try to bring to that conversation is, what piece of technology are they using in their Personal life? Are they using a modern phone? Are they using a watch that’s tracking their fitness? Do they have a modern TV at home? Are they using a robot vacuum cleaner? And it’s interesting, because I do find sometimes there’s a sort of a separation there, and that they’ve got a lot of modern tools at home or their car, but not prepared to do it in their business, and sort of try to have that conversation, to sort of unpack what’s going on there.

As I’ve mentioned, and I’ll pop in the link, Xero, in their research, found the biggest barriers were are emotional, not necessarily informational, and they’re driven by anxiety about change, about feeling uncomfortable, about feeling threatened. Family business culture can unlock or block innovation, and if they’re not prepared to move ahead, maybe it’s blocking innovation, especially when there’s trust and communication breakdowns, and it may be worthy of bringing in an external consultant to have those conversations. And I know I’ve gone into I go back. I never tell someone what to do, but I will go in and talk to them about things, and I typically go into those conversations wearing a cardigan because it’s softening, and with cupcakes because it’s softening so that they sort of I’m coming in and I’m resonating, and I’m trying to connect with them and have that conversation with them. That doesn’t always work. People have different ways of doing things, but sort of those were some of my strategies, and also talking about how the benefits I saw of other business owners who had adopted the technology.

Another paper that I’ll link to is the OECD has a white paper called “SME digitalisation to ‘Build Back Better'”, and they highlight that many smaller firms lack a digital culture at the management level. So that is a. Are the older people in the business aren’t comfortable with digital technology, and again, that’s leading to that level of mistrust about the adoption of digital technology. You know, is my existence here still valid, so hopefully that was a sort of bit of a useful conversation.

If you’re a young adult listening, your job is not to win the argument. It’s to run a small experiment that makes the owner’s life easier while protecting the business that they’ve worked so hard to build. And if you’re the parent who’s running a family business listening, well maybe open up to the opportunity of trying one small thing without signing up for total overhaul, without signing up for handing over the keys and everything. Just say, okay, look, I’m happy for you to come in and make one small change. I want to understand it and but I’m going to leave you to roll it out, and then you come and show me how it works.

Thank you so much for listening to the accounting apps podcast. I encourage you, if you’re listening in, to hit subscribe, to jump over and sign up for the Accounting Apps newsletter, and to sign up to up to join the Accounting Apps Mastermind group, so you can find the newsletter at accountingapps.io. I also encourage you, if I talked about WorkGuru at the start, and if that’s a solution that’s of interest to you, jump over and take a look at that and connect with Tony Harcourt on LinkedIn. I’ll pop a link to the post that he made, and you can share your thoughts there as well. Thank you so much.