363: Simplify Your Tech Environment with Denis O’Shea

Denis O’Shea, Founder of Mobile Mentor, helps organizations pursue a clear goal to simplify your tech environment while strengthening security and empowering employees to remain productive. Driven by the joy of learning and intellectual adventure, Denis left a 15-year career at Nokia to build a company that learns about emerging technologies, translates them into business outcomes, and mentors customers through change.

In this conversation, Denis introduces The Tech Stack Streamlining Framework: Understand Current Tech Stack, Assess Capacity for Change, Benchmark to Peers, Build the Roadmap, and Deliver Simplified Tech Stack. He explains how immersing his team in a customer’s environment, asking thoughtful questions, and benchmarking the organization against its peers can reveal a clear path toward a simpler technology stack. Denis also discusses Mobile Mentor’s fast-growing mentoring service, how its Microsoft partnership transformed the business, the challenge of finding technology professionals who are natural mentors, and why people must remain responsible for the quality and accuracy of everything they produce with AI.

Good day, dear listeners. Steve Preda here, Management Blueprint Podcast. And today my guest is Denis O’Shea, the Founder of Mobile Mentor, a technology service provider helping thousands of clients find and maintain the right balance, securing devices, protecting data, and empowering people to be productive. Mobile Mentor is also a five-time Microsoft award winner. So Denis, welcome back to the show. 

Thank you, Steve. Thank you for having me back. And I have to say, you look fantastic. You’re aging gracefully, and I hope I’m doing the same. 

Well, unfortunately, my barber is on vacation, so I couldn’t visit him last week. But it’s great to have you back on the show, and we couldn’t agree whether it was two or four years ago that you were here. Anyhow, it’s great to have you back, and I’ve got some questions for you that I’m curious about. And first and foremost, the question is, what is your personal Why, and how are you manifesting it in your Mobile Mentor business? 

My personal Why is probably learning. And I think the reason I went into business in the first place was to learn and grow as an individual. It certainly wasn’t money. I expect money as an outcome from the process, but I didn’t go into it for money. It was really to learn, and the trigger for me was I did an executive education program in Switzerland. I was living there for a few years, and that blew my mind. That just exploded my mind when I started learning all about mergers, acquisitions, turnarounds, management buyouts, all these different ways of growing a business that were nonlinear. 

And that motivated me to go on and do an MBA, and that then motivated me to leave my employer, who was a great company. I was working for Nokia for 15 years. They were amazing, but I decided to leave them and go out and embrace all this nonlinear stuff and found a company from scratch. And one day I thought maybe I’ll do a spin-out, or maybe I’ll do an acquisition, and I’ll do all these different things. And it was purely for the joy of learning and the intellectual adventure. So I think that’s my Why. It’s learning. 

Yeah. Well, learning is great, and it’s a big driver of businesses when they are able to learn, especially in today’s age. So tell me a little bit about how Mobile Mentor is reflecting this way of learning. Is it a learning organization, and in what way is it? 

Oh, that’s an interesting question, Steve. I would hope we are a learning organization. Something I’ve been saying to my kids and my staff for years is, “We’re a learning species. We can learn anything we put our minds to.” And so I would hope we are a learning organization. And the word “mentor” plays a huge part in not just our brand, but how we work. So we’re a technology service company. We’re always unpacking the latest technology and helping customers figure out what to do with it and how to extract value from it. 

So I would hope that we’re good at learning what the technology can do and then translating that into outcomes for customers and helping people unlock the full potential of the technology they’ve just purchased. And when we started 22 years ago, we were focused on mobile devices. That’s why the company’s called Mobile Mentor. Nowadays, it’s mainly AI and security and all that. And by the way, we’re going through a rebrand. The company’s just going to be called Mentor going forward. Just Mentor. So that we can work with all technology, so we remove any association with that small device where we started 22 years ago. So I think we are very good at learning, internalizing the new technology, and then translating that into business outcomes for our customers. 

Yeah. 

That’s what I feel like our core skill is. 

Yeah. And I love this concept of mentoring because essentially it’s not about teaching people, it’s about helping people discover how to be great. And if you can do that, that’s amazing. So that brings me to the next question, which is about frameworks. So this, as you know, this podcast is about frameworks, and what I’m curious about is, what’s a framework that has helped you grow this company, build this company, or help your clients or mentor your clients? Maybe it’s a mentoring framework. Maybe it’s a technology framework. So something that comes to mind that can be explained in three to five steps to our listeners. 

Sure. We have a really strong framework at the front end of our sales process. It’s an assessment and roadmap we do for customers. And it’s something that’s on our website. It has a price point, so it’s got a value, but we choose to give it away for free when we get a strong, well-qualified opportunity, or when we have a channel partner bring us a strong lead. We will use this assessment and roadmap process to build a vision for the customer. And the way we do it, we’ve got a good framework for this. 

We go through an assessment. So we tell the customer, “We’re going to have a look at your environment holistically and get a really good understanding of the technology stack you have today, all the different technologies you’re using, and also get a good understanding of your organization’s capability and capacity for change, and how you embrace change, how you make change happen. “And we’re going to show you how you compare to a whole bunch of other organizations.” I think we’ve done 174, 175 of these in the last maybe three years.

And so we show the customer how they compare to others in their industry and also against others roughly their same size. And then, most importantly, we build out a roadmap, and we show them, “Here’s how you can potentially go from where you are today with today’s technology stack,” which is usually very busy, it’s usually a long list of technologies, “to a much simpler technology stack in the future if they’re willing to consolidate on one or two platforms and do all the possible integrations, automations, and simplifications so that they’re extracting much more value from one or two platforms, like Microsoft, than having a whole colorful mix of different technology vendors.” 

So we’ll say, “Here’s a journey you could go on,” and then we describe it in vivid detail, showing all the different parts and how they would go passwordless, how they would automate setting up new employees and all the technology they need, how they would automate all their patching and security, how they would embrace AI into their operations, how they would use AI for productivity improvements, and kind of show this technology journey. That process, or that framework, of doing an assessment, and it covers 120 different topics. So we do the assessment, the comparison, the roadmap. 

We find that to be extremely powerful because customers will look at that, and they’ll look at the destination and say, “Right. We want to be there. We want to get that outcome,” and then they’re buying off us. We’re not selling to them. They’re basically saying, “Okay. We want to get there. How do we do it? Help us. How can you come in and help us do it?” So the narrative flips from us being a sales organization to then being a mentor and helping the customer figure out how to get there. 

And of course, we want to sell services, and we want to sell long-term contracts to say, “Yes, we can take you from here to there, and it’s a three-year engagement to do all those changes.” So that’s what we want. But the customer is buying it off us because they’ve bought into the destination. 

Yeah. And that’s the modern buyer’s journey, right? They research you. Before even they come to you, they want to listen to you because you might have something for them. So I love this framework. So what I noted down was step number one, understand the technology stack that they have. Step number two, assess their ability to manage change or to handle change. 

Yeah. 

Then you benchmark them to others in their industry or in their peer group. Then you build the roadmap, and then you show them the simplified end state, the simplified tech stack. 

Correct. Correct. And then we give them options around how we can help them to get there. Usually, there’s three options. And we say, “Well, what style of engagement works best for you? How would you like us to work with you?” And then it becomes a very comfortable, easy sales process from there, and it becomes easy because we’ve done all the listening. 

So when we do the assessment and we cover 120 topics, we do 60 questions in 60 minutes. So it’s two one-hour sessions. And we call it our “friendly interrogation.” But what happens during that time is what I call a selfless immersion in the customer’s world. So we don’t talk about us. We never talk about us. Everything is about them, their technology stack, their environment, their processes, their technical dependencies, all the things about their organization. 

So we get this really rich understanding of their environment. And at the end, guess what they say, Steve? Or guess what they say at the end of that interrogation or that assessment session? 

I don’t know. Give it to us. What do they say? 

They say thank you, which is extraordinary, and it surprised me when it started happening. But people love to be heard. We’re not selling. We’re not pitching anything. We are just seeking to understand their environment and asking a whole bunch of really good questions. So we don’t need to tell them who we are and what we’ve done, that we’ve won Microsoft Partner of the Year and blah, blah, blah. We don’t need to do any of that. 

They know that we know our stuff because of the questions we’re asking, because those questions have been refined and refined and refined. So we’re able to get right into the heart of their issues, and they tell us all about their environment and their issues and concerns and frustrations. And at the end of the assessment, they say, “Thank you.” And I remind them, I say, “We haven’t delivered anything yet. All we’ve done is asked you a whole bunch of questions.” But they feel like it was almost a cathartic process of unloading and sharing all of it. And then we do the second session, and the rapport gets even better, and they bring in some different people. 

So by the time we get to the end of the assessment, we’ve had a really good conversation about 120 different things. There’s now a high degree of trust. And so when we come back in the third session, we say, “Okay, we heard you. Here’s where you are. Here’s how you compare to others. Here’s where you could be, and here’s what the journey would look like to get you there, taking all the complexities into account, all the dependencies, all the legacy, all the technical debt you might have. “Here’s what it would take to get you to where you want to be.” They’re now listening and they’re trusting us because we’ve listened to them. 

Yeah. I love that. That is very powerful. And asking good questions is actually not always easy. In the age of AI, answers are omnipresent, but good questions, good prompts, that’s a skill, right? To ask the right question. 

It is. And it’s interesting you mention AI because we’re not using any AI in the way we do this. We could choose to send out a form to the customer and say, “Please fill out this form.” Actually, we tried that. We tried that 10 or 12 years ago in our New Zealand operation, and it was a complete disaster. Nobody wants to fill out a long form and answer all those questions. But if you have a conversation face-to-face, on Teams or Zoom, whatever, you can have the conversation. You’ll get all the information. 

But now we’re establishing rapport between us while we do that, and that also gives them a flavor of what it’s like to work with us. How we interact and how we follow up the question, how we drill down, how we clarify and confirm, “Did I understand that correctly?” in a way that you don’t get from just filling out a web form. And we also don’t use AI to analyze the transcript and try and fill it out. We actually do it based on us understanding it, because we find we get way more detail and nuance than relying on a transcript. 

That’s very interesting. Definitely, when there’s a human on the other end who is interested in what you’re saying and is listening deeply, it’s a highly motivating and even inspiring thing. That’s why it’s hard to make a talk without the audience, because you need the energy of the audience. So you provide the energy for them to come up with the goods and explain where they are, right? 

Yeah, yeah.

So let me switch gears and ask you this. What drives growth in your business? 

What drives growth? Two things. One, that process sets us up to be able to sell something. The fastest-growing thing that we sell is a service called mentoring, which is very closely aligned to our brand and the way we work, and it’s something that’s very unique to us. So what we figured out is that there are some customers who just want to bring in a partner to build something for them let’s say to deploy some new technology, and then they want the vendor to go away and leave them with it. There are other organizations who don’t want to touch the technology. They want somebody to provide a managed service, so you get all the outcomes. 

And those two technology service categories have been around forever, right? Microsoft has 400,000 partners doing this kind of work, doing project work, or providing managed services. We found a huge white space in the middle between those two. We found there’s a big white space in the mid-market, in particular mid-market organizations, where they have their own IT team. They don’t want to give the keys away to a managed service provider and let go. They want to learn all about the new technology. 

They want to internalize the knowledge, and they want somebody to come in and help them deploy it with them, and be hands-on-keyboard, and do it together with them, and do lots of knowledge transfer, and help them build the documentation and the knowledge base, and get the experience and the skills so that their skills grow, their confidence grows. And we call that service mentoring, where we’re doing that for them. So we’re not just building it and walking away, we’re building it together with them. And it can be a one-year, two-year, five-year engagement where we’re building out this complex technology capability, but we’re doing it together, and they become the experts over time. That is our fastest-growing, top-selling service. 

That’s fascinating. So it’s essentially coaching, mentoring, and still you turn it into an ongoing engagement because it’s not simple, right? There are a lot of layers to it. And what’s the timeline of such a relationship? 

Typically three years. Typically. It can be as short as one, it can be as long as five. But for most of the technology transformation projects we’re doing, I would say they’re two, three, four years for the organization to change and embed all the changes and turn off all the legacy technology and fully embrace the new way of working. So our typical contract is three years. And then we set up all the cadences so that we’re working together every week through specific things, and there’s a weekly cadence, our engineers doing all that stuff, and then monthly coming up for air to see how we’re doing against the roadmap. Do we need to make any changes? What’s the focus for next month? And that’s a rolling process that keeps going on and on. And so the two teams end up working extremely closely. 

Our engineering team, and we’re bringing in different architects, engineers, and there’s obviously a consistent project manager across it. And on the customer side, they’re bringing different engineers or architects depending on the piece of work we’re doing. But it’s generally all modernizing the way they work with Microsoft technology primarily, and changing from legacy stuff to very modern, invisible security, embedded AI, really trying to accelerate their maturity as an organization. 

Yeah. Love it. 

Does that make sense? 

So it makes sense. I’m wondering, I mean, most businesses these days, they want to have recurring revenue, and even though you have a three-year engagement, it’s still not an evergreen engagement. So what do you do to turn these engagements into more of an enduring one, or you’re not trying to do it because it’s not the purpose? 

That’s the $64 million question for our business, Steve, is how do we turn a two-year or three-year engagement into something longer? And it actually comes back to where you started with the learning thing. So what we need to be doing, and this is a constant battle for us, is learning about the latest and the newest technologies and staying ahead of the customer. Always staying ahead in terms of our knowledge so that we can keep adding new things to the backlog of work that needs to be done. 

So that we might deploy technology A and get that done and do the migration and modernization, but then we need to move on to B and C and D and E. And there’s always new stuff, and actually the rate of change is accelerating now with AI. Everything is changing so fast, it’s unbelievable. But our job is to stay ahead so that we can always have something new and edgy that we can bring to the relationship. That we’re always able to give new knowledge, information, value. 

So is it a managed technology business or is it more of a consulting business? 

Ah, we are three different things. We do a lot of project work where people will come in and say, “Migrate us from platform A to platform B.” So we do that. We do this mentoring service where we’re doing the change and modernization together with the customer. We’re also a managed service provider. We have a lot of small and medium businesses that say, “We don’t have an IT team. We don’t want to have an IT team. Manage this stuff, make it invisible to us. Just give us great service and give us great reports and be transparent with us.” And that’s part of our business too. 

So I would say we’re roughly one-third professional services, project work, one-third mentoring, and one-third managed services. So more than half the business is recurring revenue in any given year. 

So what makes this kind of business hard to scale, or what makes it easy to scale? 

What makes it hard to scale is finding great people who can learn and share that learning with customers, so people who are natural mentors. So what we do not want is to hire geeks who want to just put on noise-canceling headsets and sit in front of a screen coding all day. They would not work for us. We want people who are head up, good people skills, want to learn it, but want to share it. Naturally very good at sharing. So getting the right people, that’s one constraint to growth. The thing that makes growth easy for us is our relationship with Microsoft. That’s unbelievable. 

We didn’t have a relationship with Microsoft 11 years ago, and they came to us and asked us to become a partner, and we did. And they asked us to work with them on a specific technology that was very immature at the time. And I set a goal for our team. I said, “What would it take us to become the best in the world at that one specific technology? To become the best in the world on that technology as it matures and grows?” And we set that as our North Star and really went after that and focused everything on that. 

And that enabled us then to win Microsoft Global Partner of the Year based on our focus on that. And by winning that award, that got us noticed because they got 400,000 partners. So at the time, I was based in New Zealand, so basically the second-last rock before the end of the earth. And so we were nobody in a nowhere place and not noticed, and we’re just one of 400,000, completely lost in the noise. We got noticed when we won Global Partner of the Year and when we got recognized for being the best in the world at that one technology, and that changed everything, and I moved to America. 

Then Microsoft introduced us to a whole bunch of customers, including the largest healthcare organization in the world, the largest education provider in the world, and largest government departments. And so now our business is totally different to what it looked like 11 years ago before Microsoft. And this goes on and on. So almost every day, they contact us to say, “Hey, we got this customer over here, and they got this problem, and we thought of you.” And then they introduce us, and we do our assessment, show them how they compare, build a roadmap, and say, “What would you like to do from here?” 

Yeah. I’m just very curious about what is that technology, and what is the ideal customer for you for that technology?

That technology is a platform called Intune. It’s a device management platform, so it’s for managing desktops, laptops, MacBooks, smartphones, tablets, and all that. And everything we do, of course, starts with a device. And so it’s the technology that secures and manages and configures our devices. Microsoft Intune is the name of the product, and that’s where we’ve got very, very deep expertise. But that leads us to all the other parts of the Microsoft 365 environment, and most organizations are using Microsoft 365 to some extent. 

So in most cases, they’re coming to us and saying, “Hey, this customer has bought our licenses. They’ve got Microsoft 365 E5 or E3, whatever. They’re not using it all. They’ve got all these overlapping competitive products. They want to consolidate, reduce costs, or they want to improve security, or they want to simplify their environment. Can you help?” And we’re like, “Hell yeah, we can help. That’s right in our wheelhouse.” And so we have a discovery call with the customer. They tell us what they want to achieve, and if they’re a good fit for our assessment and roadmap, then we’ll propose that. So we’re not trying to sell anything at that stage, and we’ll do that. 

It’s many, many hours of work. We’ll do that roadmap and assessment at our cost. Sorry, that’s our investment. That’s our investment in the relationship, so that we’re showing that we’re giving value back to the customer and to Microsoft because they brought us that lead, and we’re creating value from day one. And sometimes the customer will go, “Thank you. We understand the journey. We’re going to do it ourselves,” or, “We’ve got an existing partner,” or, “We don’t have budget,” whatever. And so we don’t land them all, but we’ve got a very high conversion rate. We land a lot of them. 

And even if we don’t, I know that we deliver a huge amount of value through the process, and the customer goes, “Wow, that was great. That was a great process. We learned a lot. We can see where we need to go. We might be back in touch in the future when we do have budget or when the stars align.” 

Or they refer someone else. 

Yeah. 

So if you had a magic wand and you could fix one thing in your business in the next 12 months, what would that be? 

I would say it would be doing more with AI internally. Some days I feel like an imposter because we are selling a lot of AI services, and we do a lot of AI work for our customers. But I, as the leader, I don’t do enough. I’m not doing enough with AI. I’m not building enough capability. I’m leading the charge, but I’m not savvy enough myself. And I feel like our leadership team could be doing more. So I feel like doing more, embedding more AI into how we work, is something I want to change or fix in the next year. Not just doing it for customers. 

Yeah. I mean, you can never do enough with AI, right? There’s so much out there and so much changing, and to stay ahead of it, one’s head is spinning all the time. It’s very inspiring, but can be also overwhelming. 

That’s true. And one of the things I’m dealing with is managing what we call AI slop, where we see people internally and externally producing things that are not good-quality outcomes because it hasn’t been double-checked. So just because it could be produced quickly and easily by AI doesn’t mean it’s great or specific enough or detailed enough or accurate enough for the result, whether that’s an internal report or an external thing. 

So the coaching I’m giving people is you’re still responsible for the thing, the quality of the thing. You have to read it, make sure it’s on point, it’s detailed enough, the customer’s going to be happy with it or your manager’s going to be happy with it. We are still responsible for the thing we produce. Let’s not get lazy. 

Yeah. And the more content you generate and the more solutions you generate with AI, the more the mental load on the decision-makers to actually filter out what’s not real and what’s real. 

Yeah. Yeah. Yeah. 

Yeah. I can see that happening. So if someone is listening to this and says, “Wow, I love this idea that you benchmark me, you figure out what our tech is, learn our tech, benchmark us, come up with a roadmap, and evaluate the organization, how fast we can manage change, and then come up with a roadmap and mentor us to get there and simplify our tech stack,” and would like to learn more and perhaps connect with you, where should they go? Where can they find out more information? 

I’m on LinkedIn only. I’m not on other social platforms. I’m a bit of a Neanderthal in that regard. But Denis, with one N and O’Shea, O-S-H-E-A, on LinkedIn, and my company is Mobile Mentor. It will be Mentor soon, but we’ll keep the Mobile Mentor alive for quite a while. And so go to the company, mobile-mentor.com. And yeah, love to talk to any of your listeners and audience if this is a technology journey they want to go on or want a partner to work with them. That’s the role we play, being a mentor and helping people get the outcomes, but internalizing it and becoming experts while doing so. 

Yeah. So if you want to filter out the AI slop and the AI noise, and you want real people who will look at your specific situations and help you and mentor you and help your staff get up to speed and simplify, then reach out to Denis. And if you enjoyed this conversation, stay tuned because every week I bring a couple of entrepreneurs who are sharing their frameworks of how they’re improving and growing their businesses, and you can implement some of these things yourself. 

So thanks, Denis. Denis O’Shea, the founder and CEO of Mobile Mentor, soon to be called Mentor. Thanks for coming on the show, and thank you for listening.

Thank you, Steve. Always a pleasure.

• Denis’s LinkedIn
• Denis’s website