Ask Me Anything

How to be an IT consultant for small and medium businesses with "Tech Caddy" Anthony McMahon

Digital Transformation

July 13, 2021
min read
Anthony McMahon, founder of Target State Consulting

The self-styled Virtual CTO / Technology Caddy talks IT consulting with SMBs and the impact of emerging tech on the labor market

Anthony McMahon is the Virtual CTO and Founder of Target State Consulting (formerly The IT Psychiatrist), providing "the technology executive you need, when you need it, at a cost that works for you." Anthony sat down for an ask-me-anything with Pulse Product Manager, Lisa Peng.

In your bio you go by the uncommon title “technology caddy.” Could you explain what that means?

I don't like that term consultant because it has so many negative connotations to people. I came up with the “caddy” when thinking about golf: You've got a pro golfer who's out there playing golf, and right beside them every step of the way, advising them on the shots to take, the club to use, how to play a green, how to play anything, is their caddy. That's the role I'm playing in the tech space. The tech caddy is someone who may not be running the business, but they're walking every step of the way in the same shoes as the business owner or the business leader they are working with, and advising them on when to use certain systems, when to use certain data points, how to get the most out of what they've already got and whether to pivot away and actually replace systems. It’s a little bit of fun, and it actually got quite a lot of positive reactions from the fact that I was saying we're there walking every step of the way with you, not just trying to sell you more and more solutions.

Do you have a unique term to describe your role? Comment on this post in the Pulse community.

“[A technology caddy is] walking every step of the way with you, not just trying to sell you more and more solutions.”

I really love that. So, you've had a long career working in IT in-house before making the transition to your current role—what got you interested in making the transition from in-house to the more consulting role?

I had a fairly long career in-house with one of New Zealand's largest banks. I'd had a variety of roles there. The last one I landed on was an enterprise architect. I saw that big companies have the scope to take on roles like enterprise architect, to build a strategic function and a team that's future focused and looking at what the organization needs to be doing to overcome the challenges of tomorrow. They can also afford to pop down the road to a consultancy company and bring in the knowledge when they don't have it, and they can afford to absorb the mistakes along the way.

What I was starting to realize was, that's great at the top end of town, but in New Zealand, 96%-97% of our companies are classified as small and medium. So that's up to 200-300 staff, with turnover of between $5-$20 million dollars. And these smaller companies would get the same benefit of having that advice on how to structure their digital footprint to actually enable the business and make the jump from some of the legacy tech platforms, particularly on-premises to more cloud focused. They need it, but the problem [is] they can't afford it, and they don't necessarily have the budget to take that role in-house full time.

So when going out into a consultancy model from in-house, what I was looking at was to take that in-house model, big business thinking and put it in a mid-sized, mid-market budget. That is where the VCTO, Virtual Chief Technology Officer, and VCIO, Virtual Chief Information Officer, branding came from. Because if I go out and say, “hey, small/medium business leader, I'm an enterprise architect.” They'd look at me and go, “you're a what now?” And so by explaining it as, “I can give you the skills here, here, here, and here,” and branded as the Virtual Chief Technology Officer, that helped sell the value a lot cleaner than trying to talk about enterprise architecture.

Would you rather be an in-house architect or consult a variety of businesses? Comment on this post in the Pulse community.

What is your #1 piece of advice for IT leaders who are interested in making the same transition that you did?

Just get out and start talking to people, start talking to business leaders, start talking to anyone who's in a non-technology role, traditional non-technology role and find out what their pain points are and what it is they need help with. The main thing I'd stress there is, don't automatically assume that solutions will be the answer. Sometimes it literally is guidance and advice.

Do you have advice for aspiring consultants looking to establish themselves? Comment on this post in the Pulse community.

“Just get out and start talking to people [. . .] find out what their pain points are and what it is they need help with [. . .] don't automatically assume that solutions will be the answer.”

Based on your experience with a variety of organizations, do you feel the pandemic has increased or decreased the risk appetite of the business?

I think it's decreased the risk appetite a little bit, but it's increased the awareness of how technology, appropriately applied, can manage a risk portfolio for a company. If you go back 18 months, there are companies out there who would not have had a business continuity plan or considered remote working that are now working from home.

Do you think the pandemic has increased or decreased risk appetite? Comment on this post in the Pulse community.

You have spoken on the topic of mindset over method. Is that something you could expand on?

Having been in-house for a while and seeing the transition of waterfall to agile, I noticed how companies or people particularly have gotten a little bit territorial about projects and the way they're delivered. One of the things I started to realize was that it's not the methodology you use that's going to be successful in the project, it is the mindset that the team has around it.

And the reason I say that is, there's plenty of waterfall projects that have successfully delivered on time and on budget because the team had the right mindset towards it. And equally there's plenty of examples of agile projects that have failed to deliver, because the team involved haven't had the right mindset or haven't bought into it.

Two years ago, we had the America's Cup in New Zealand. A global yachting event. When team New Zealand launched their boat that they were going to be competing with, getting the boat on the water was a waterfall project. There is no minimum viable product for a racing yacht, other than the yacht floats and it's on the water and it's ready to go, so a waterfall approach made sense. But as soon as it hit the water, that project stopped and they pivoted to an edge delivery. They were taking it out and testing, making changes, making adaptations and getting it going faster, and faster, and faster. What they bought into there was the mindset approach. They never went, “we are waterfall” or “we are now agile.” They went, “we're just trying to make the fastest boat in the world and we will have the best people around it.” So that's where I am coming from with mindset over method: It doesn't matter how you deliver a piece of work. That's not what's going to determine the success of it. What's going to determine the successes is that you've got the right people involved and that they bring in the right mindset into it as well. It's a team and people that understand that change is constant.

What are your thoughts on waterfall vs. agile? Comment on this post in the Pulse community.

“It's not the methodology you use that's going to be successful in the project, it is the mindset that the team has around it.”

What do you do to foster that mindset in your team?

Minimize processes for the people that you've got around you. Avoid putting up all these barriers and forcing them to do process after process. You can't take all the process away. You've still got to have structure in there, but minimize it as much as possible so that they're not bogged down in bureaucracy and being mentally fatigued before they've even started.

Think incrementally about forecasting. You often hear it's impossible to forecast a project, so we're going to do a minimum viable product or we're going to do a sprint. Keep thinking like that, but also you've got to have an idea of the bigger picture at the end of the day. Coming back to that Team New Zealand yacht, their forecast was that they were going to have a boat that was capable of defending the trophy. So everything they were doing was incrementally improving their boat along the way, but at the end of the day, they had a very big picture vision on what they needed. Make sure the team understands the vision and they're aligned to it.

But, don't be dogmatic about the milestone or goal you set, be prepared to adjust it and adapt it. Don't get stuck on, we must be agile, or we must be waterfall to deliver this. Just accept that circumstances at certain times are going to demand a different way of doing things and a different approach to doing things.

And the last one, and this is a little bit poetic, if you can't coach the mindset or the team, poach it. If you haven't got the people around you that you need, if you've identified skills gaps, if you've identified people who are missing and you haven't got the opportunity to coach them, just go out and poach it. I can't coach it, poach it.

How do you foster a growth mindset in your team? Comment on this post in the Pulse community.

We hear a lot about the challenge to up-skill workers in order to adapt as jobs evolve with new technology. How optimistic are you about minimizing pains in the labor market as we make those transitions?

I'm fairly optimistic about it actually. There's going to be some pain. Unfortunately, some people are going to end up losing the job they may have had for a number of years. But at the same time, other opportunities are going to open up. And I think that's where it's on those of us who are fortunate enough to be in that leadership position, or making those decisions that are going to impact workers, to be transparent about it. If we are bringing in automation to take over certain tasks, explain to people that it's not about trying to cut costs and get rid of them. Point out what's going to happen as a result of that introduction and explain to them what that means for their jobs as well, and make sure they're comfortable and confident because that's probably the biggest thing. If you're open and transparent at the start, even if it's to the point of, “we don't know what impact this will have on us as a society, but let's deal with it together,” that's going to get a lot more buy-in, than, “no one's going to lose their job as a result of this.”

How do you minimize transition pain with emerging technology? Comment on this post in the Pulse community

“It's on those of us who are fortunate enough to be in that leadership position [...] If you're open and transparent at the start, [...] that's going to get a lot more buy-in”

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