Why Tech Companies Suck at Risk Analysis

Apple Podcasts: https://apple.co/2NHRRDl
Spotify: https://spoti.fi/3AyHCUd
Youtube: https://youtu.be/7uIOwxWU_HU

In the tech world, we tend to focus on the tasks that directly correlate to our work. But if we only focus on things like fixing firewalls and cybersecurity without understanding our clients - that is what makes tech companies suck at risk analysis.

That is not to say that what we do is unimportant. Our clients would not have hired us if they did not need our services. What is important is that we understand that to our clients, there is a difference between technical risk and business risk.

It is only natural that tech companies focus on technical risk. It’s what we do! But, you must remember that business risk will always outweigh technical risk to your client. Make it a point to talk to your customers. Understand what they see as risks and threats to their company, and then align your services with their needs. For example, if you have a client that runs a dog kennel, their main concern is the health and safety of the animals. If you only talk to them about everything you have done to improve their cybersecurity, your words will fall on deaf ears. But, if you can explain to them how improvement to their cybersecurity helps oversee all dogs that they are caring for and allows owners to safely access live streams of their pets from work, you have proven how your goals match those of your customers. Now your client has more features to sell to their customers, and you have opened the door for your business to provide additional services to build an ongoing relationship.

Aligning technical risk with business risk benefits you and your customers by providing a clear path to success. It helps your clients prioritize the factors that threaten their business and enables you to understand how your services help them meet their goals. Use this as a foundation to expand your business.

Business Risk x Technical Risk = Opportunity

When your client understands how the risks and threats to their business can be resolved by addressing technical issues, it allows you to cultivate your business relationship and the opportunity to offer additional services. In turn, it is your responsibility to ensure that you understand your customers. Focus on what your clients care about and what is most important to them. Learn how to identify the problems they face and then mitigate them to how IT can help prevent problems from happening. This strengthens the trust your clients have in you, provides direction for you and your client and creates a base on which you can expand your services.

Tech companies don’t have to suck at risk analysis. We just need to listen and understand how our work impacts client businesses and reduces the threats they face. Building client rapport is more than just doing a good job. Remember, we have conversations, not presentations! Take the time to understand what they value. Turn your risk analysis from sucking to spectacular!

PitchIT Volume 2

Apple Podcasts: https://apple.co/2NHRRDl
Spotify: https://spoti.fi/3AyHCUd
Youtube: https://youtu.be/xK0KEi-AKD8

Welcome to the second part of PitchIT with Sean Lardo of ConnectWise! We’re diving deeper into our IT world and how to provide your service to clients.

For those of us who work in IT, we know that our industry is ever-changing and growing. However, the growth that we’ve seen over the last few years has been exponential. When Covid hit, our services had adapt and expand in ways we did not anticipate. People had to stay home and run their businesses while out of the office. Innovation wasn’t what we wanted. It was what we needed!

Serving our MSPs is, of course, always at the forefront of our work. But how do we ensure they have the resources and understanding needed to do their jobs? The answer is simple, and ConnectWise has broken it down into 3 promises they make to their clients.

Be easy to work with
Invest in partner growth
Bring more innovations faster

Being easy to work with sounds simple, but it’s more than being friendly and showing up with a smile. You need to know your clients’ needs and develop solutions they can understand. Your clients deserve to know your company’s value and how it betters them. When people think of IT, their first thought is cybersecurity. But MSPs work with everyone from mechanics to bakeries by providing services from HR automation to accounting. Understanding what your clients want and need makes it easier for everyone to achieve their goals. Make it a point to know your clients and be personable! Ask them about their weekend. How’s the family? Let them know you care and are genuinely invested.

Investing in partner growth helps your client achieve their goals and keeps ongoing business by building stronger relationships with your customers. At MSPL, we believe in conversations, not presentations. Before meeting with a client, send them an agenda with your understanding of their needs, how you can address them, and how to move forward in the future. It tells your clients you are listening, invested, and have a firm grasp of their goals. Don’t use your PowerPoint or slides as the basis of your meeting. Use it to keep the conversation on track and address the topics that need to be discussed. An hour-long conversation should only require 20 minutes of slide show presentation. Tailor your conversations to your clients. Showcase your understanding of their needs, that you’re invested and how you can be of service.

Your clients want results, and they want them now! When you talk to your customers, you’re telling a story. Let them know how far they’ve come, where they are now and what the future holds. Each conversation needs to be better than the last. It allows your client to see how quickly you’ve improved their organization, where they are now, and the potential yet to come. Know your vertical, your space, and own it! New IT companies sometimes get into the pitfall of, “We can do anything!” but that’s not necessarily true. Sometimes a request goes beyond the scope of your abilities, and that’s OK. Be honest with your clients and help them find another venue to fulfill their needs, even if that means sending them to your competition. It shows the clients that you care and want to get them the best results as soon as possible.

Serving clients is the primary goal of any business, IT or otherwise. By being easy to work with, investing in partner growth and bringing more innovations faster, you are setting yourself and your customers up for success!

The evolution of Entertainment

Apple Podcasts: https://apple.co/2NHRRDl
Spotify: https://spoti.fi/3AyHCUd
Youtube: https://youtu.be/f3VfzE4CSW4

Entertainment and business - do the two of them go hand in hand? Absolutely! This week, we will talk about the entertainment industry and how to apply it to your business.

It is easy to fall into the old idea that the streams of work and play should never cross. But that is not necessarily true. If you think about it, our society is driven by entertainment. For you to be successful, you have to pay attention to what is going on in the entertainment industry.

When you are at work, what tools do you usually utilize? Do you use messaging platforms like Slack or Discord? Do you host virtual meetings with your clients or staff? You can thank the gaming industry for that. Think back to the 90s and early 2000s. Games went from platform leaping side scrolls to remote play. Suddenly, we were able to play games and connect with people all over the world. Next came VR. Now you can share virtual worlds, games and sports with people from the comfort of your own home. Whole companies and businesses have been created using what they learned from gaming messaging platforms and applied it to develop tools that organizations of every kind use on a daily basis.

Need more evidence? Look at crypto-currency. It’s not something you can put in the wallet or purse, but it’s definitely got value! They have turned graphic cards into something that is more than just something cool to look at. It’s an actual form of currency.

Our world is always changing. What engages people, what pulls people in - like it or not, it has to be entertaining. If you want people to lean into your message, they have to enjoy it. This means you have to pay attention to the ongoing trends. Check out the latest YouTube videos or what’s trending on social media. What are people tuning into? What are they watching? What online games are popular? Why? Now, put yourself in your clients’ shoes, answer those questions and help them implement plans to push the envelope and keep them fresh. The same goes for you and your business strategy. Keep up with the times and keep your audience entertained! Your impact will be much stronger when people have fun.

So, how does the formula to success in entertainment match a business model? The answer is simple: When demand increases, so does the value. When the value increases, there’s money to be made! Learn what makes a business tick. Whether it’s you, a client or MSP, it’s up to you to keep things moving. Success is essentially a gaming model. You start on level one, master it and then move on to the next level. It’s up to you to ensure that each level is mastered before moving on to the next.


Now, that’s not to say that everything “old” is obsolete. There’s a whole market for people who still listen to music on cassette or records for the “right” sound. But trends come back! When you know what is happening and what is driving people to engage and tune in, it helps you understand what people value.

Entertainment is successful because it is constantly evolving. It tries something new, releases it to the public and tests the waters. It may not always work, but when it does it can lead to big wins. Businesses do the same thing and like entertainment, they have to change in order to stay relevant. Switch on, power up and be entertaining!

Opportunity Preparation and Failure

Apple Podcasts: https://apple.co/2NHRRDl
Spotify: https://spoti.fi/3AyHCUd
Youtube: https://youtu.be/1NypPGLGvW0

As a business owner, you probably spend a lot of time planning. Generally, your plans probably don’t happen exactly how you thought they would—but, when they do then all the time you spend prepping is worth it. That’s exactly what this week’s episode is all about. Opportunities, preparation and failure.

Engineers have a more difficult time getting used to the concept of strategy and having a plan for the future. If there is a piece of technology that is broken, there are steps to take in order to fix it. The fix is also right there in front of you as is the solution. Once you fix the problem then you close the ticket and call it accomplished and feel the satisfaction of starting a solving a problem quickly and seeing results instantly. The effects of your efforts are visible.

For businesses, it’s not the same. Business owners have to spend time coming up with a general idea of where they want to be in the future and figure out how to get there over time.

This prep work is super important. If you have no aim for your business, then what are you really trying to accomplish? Wanting to make money is not a good enough reason to be in business. You have to have a strategy for how you will actually be successful.

It all comes down to making a plan, working that plan and then reviewing that plan. First, you need to access what the goals are for your company. What are you currently doing and what do you hope to be doing in 1, 2 or even 5 years? Have a vision for the future of your business. Then, get everyone in your company on board. If only one person knows about what your goals are, then they will not be achieved. When everyone is on the same page, start looking at current and future opportunities and match up those that will line up with your vision. Be careful not to spread yourself too thin. You can’t and shouldn’t say yes to everything just because it’s available. That will set you up for failure. Be okay with saying no to things.

If saying no is really hard for you, then think through this process any time you are considering an opportunity. Look at your goals and who your company is. Does this opportunity match who you are and will it help you get to where you want to be? If you answer no to either of these questions or don’t know, then it’s safe to say no to that opportunity.

The last piece of prepping your business is learning from failures. There are going to be opportunities that you take that will not pan out. There are going to be situations that you didn’t prepare for or prepared incorrectly. Do not beat yourself up or get frustrated with your business plan. Look at these things and learn what you could have done differently. Adjust your goals. Move forward knowing that you will most likely make that same mistake again.

To sum everything up, Look at the opportunities ahead of you, match those up with the vision and goals for your company and then make preparations for those goals. And just know that you will never get to a point where all your goals have been met and you’re done. You’ll always be adjusting and changing as you grow into a better version of your business.

The Importance of Vacations

Apple Podcasts: https://apple.co/2NHRRDl
Spotify: https://spoti.fi/3AyHCUd
Youtube: https://youtu.be/YWobWj0OcGU


Every single person is super unique, but we all have one thing in common: a need for rest and recuperation. You may be convinced that you can work and work and work with no breaks. In a world that is so fast-paced, we reward people that are hardcore and refuse to step back or take a deep breath.

Although hard work is great and should be rewarded, it’s also pivotal that you take breaks. You can only work efficiently for so long without resting. The longer you work on something with no break, the more mistakes you will make.

You’ve probably been in a situation where you’ve tried to solve a problem or fix something and the longer you stare at it, the harder it seems to come up with a solution. Contrary to popular belief, that problem will not magically become clear by spending more time staring at it. The best thing to do is put it away and come back to it in a little while. You will most likely find that time away makes the solution easier to figure out—maybe even obvious!

Your brain needs time to work stuff out and process. It is a muscle and should be treated with the same respect and care that you treat the rest of your body. Give it time to relax and put good stuff in so you can get good stuff out. Take working out for example. You can’t do your maximum lifts every single day or you will wear your body out. You have to give your muscles days to do light workouts in order to come back the next day and work hard. You also wouldn’t put the heaviest weights on and expect to be able to lift over and over without feeling completely tired and burnt out. And, after a workout, you have to stretch your muscles to allow the best recovery—basically, you have to take care of yourself.

Even if your company offers unlimited paid time off, it can be hard to take advantage of that. You want to get stuff done and you probably think the harder you work, the more you’ll get done. When you’re tired, your body goes into autopilot and simply plays the part. You may feel like you’re being productive when really, you’re getting as much done as you could.

Your brain needs a change of scenery. That doesn’t mean simply slowing down on work; it means you need to switch up what you’re doing. Find something that you enjoy like reading, playing video games or going for a walk to give your mind a much-needed mini-vacation. When you return to your desk, it will be easier for you to focus on the tasks at hand.

Vacations don’t just mean taking a week off and traveling. Taking 30 minutes or 2 hours every day to focus on something else or rest will help you put your distractions on hold. There is a value in dedicated away time that includes unplugging from your work, your phone and anything that might cause you stress.
You may think that this topic doesn’t pertain to you. But, if you find yourself snapping at people, eating or drinking more or having a hard time sleeping, then you are out of balance and your body is trying to overcompensate for your lack of energy. It’s time to take a vacation, trust us!

You should definitely still take that awesome family vacation in the middle of summer. But, make sure that isn’t your only vacation this year. Take time every single day to do something that will make your brain relaxed and make work more enjoyable. Humans were not created to constantly work. Relax and give your body time to recharge and focus!

Why are you in Tech?

Apple Podcasts: https://apple.co/2NHRRDl
Spotify: https://spoti.fi/3AyHCUd
Youtube: https://youtu.be/ArFI83D0yUE

Not only are we talking about the reasons we got into tech, but we’re celebrating 100 episodes of Humanize IT! Our podcast has really evolved from specifically talking about how to have conversations with businesses to focusing on how to build MSP culture and learning what’s going on in this industry.

Thank you for being on this journey with us! We’re excited to see what comes in the future. But for now, let’s talk about why we’re in tech!

Both Skip and I have different stories and reasons why we ended up in IT. I am an analytical person—you might have noticed. I found computers really cool in the 80s and found a love of figuring out how things work and how things are built.

Tech fascinated me, so I got a degree in computer science. When I landed my first job, I realized that the college classes had taught me important information, but I hadn’t learned the things that I actually needed to know. Most of the stuff I know now is from doing hands-on work.

Overtime, I learned that I didn’t like computers as much as I like problem-solving and strategy. I’m happiest when I can lead others and strategize solutions. But, I got here because of the IT industry and working on computers.

Skip’s decision came down to his personality and love of problem solving. In the 90s, if something technical wasn’t working, you just had to figure it out, and that resonated with him. He’s not one for a step-by-step approach. He just wants a starting point and an ability to figure it out in his own way.

Skip got an electronics degree because that was the closest thing they had to anything technical. It wasn’t exactly what he was looking for, but he learned more while working in a computer store.

Overall, Skip loved the newness of technology. It was exciting to work with something brand new and figure out how it works. Eventually, the newness wears off, but that excitement sparked an interest for him.

The thing about tech positions is no one really knows what you do fully—especially back when the tech was new. You have to be able to pat yourself on the back when stuff goes well, because no one else will probably understand the gravity of the work that you are doing.

With that being said, if you own a business, you should let the IT people be the heroes. They never get that kind of attention, and knowing that they are valuable will make their work so much more rewarding!

As an IT person, you might go underappreciated, but we get to solve problems and that is the exiting thing. Look how far technology has come! Look at all the things that we’ve done and built as a tech community. We all have our own parts in this and it’s really cool.

Here’s to 100 episodes, and here’s to the next 100!

Are you a bad MSP?

Apple Podcasts: https://apple.co/2NHRRDl
Spotify: https://spoti.fi/3AyHCUd

In your job, you most likely assume that you’re doing well. Why wouldn’t you? But, if most people think they’re performing well, how do we actually gauge that and test performance? It’s really easy to talk about what makes a good MSP, and that’s generally what we like to focus on. This is a touchy subject, but one that can really benefit you in your pursuit to be a great MSP. So, let’s get started with how to see if you are a good or bad MSP!

The first thing to look at within your MSP is client retention. If your clients are only staying with you because of an iron-clad agreement, then you may have a problem. If you’re only keeping clients because you’re the cheapest bid in town, that is also a red flag. You should be offering a value to your clients that would make them want to stay with you, no matter what. Client retention should not come from force or a constant effort on your part to convince them to stay.

If you can provide an easy out for your clients and they choose to stay, then you’re doing well. We always stress conversations with your clients, and this is a great way to talk about your value and what you provide for them. You shouldn’t have to beg them to stay!

The next thing you should dive into is whether you are continuously improving. If you’re not growing, you’re dying. Essentially, continuous improvement is the cornerstone of what makes you a good MSP. Do you know if you are operating better than you were last year? Do you have the metrics to analyze to see that growth? If you haven’t improved or don’t have ways to track data, then you’re a bad MSP.

If you answered no to the following questions, it probably doesn’t feel like you’re doing badly. Generally, a lack of improvement happens from ignorance or pride. The best thing to do is identify what could be improved within your organization. It doesn’t have to be monumental changes—just small steps that will help you grow in the long run.

The third and final metric is whether your clients are in your lane. Basically, are your clients looking for the type of MSP that you are providing when looking at both services and culture.

People are always looking for different things, and there are a ton of options for MSPs. The thing to look at is what you are providing your clients. Do those services line up with what your client truly needs? If so, great! But, if not, it is time to refer them to another MSP that will align with them better.

Let’s say you work really well with schools, and that is your niche. Almost all of your clients come to you knowing that and looking for high-quality services that might cost a bit more but will align with the education field. If a hospital comes to you looking for the cheapest option, chances are they are not going to be a good fit for you. As a good MSP, you would refer them to another agency that will be able to serve them best.

Use metrics—customer retention, continuous improvement and whether you align with your clients—to test whether you’re a good MSP. If you aren’t, then it’s not too late to improve in each of these areas! If you are doing well, then maximize those skills!

Tech and Teens

Apple Podcasts: https://apple.co/2NHRRDl
Spotify: https://spoti.fi/3AyHCUd

We’ve got a very special guest with us for this week’s episode: Lizzie Walter, my daughter! We’re talking about one teenager’s opinion on technology and how it affects school, home life and friendships. Here’s a glimpse into our conversation!

Adam and Skip: What kinds of technologies rule your life right now?

Lizzy: Snapchat and Instagram. I don’t have Snapchat, but most teenagers have them. I usually use Instagram over most other things, even though Instagram is pretty similar to Facebook.

Adam and Skip: When we were in school, we used to have books for classes and carried them around in our backpacks. Today, most people have Chromebooks for school. What do you guys use for school?

Lizzy: Google Classroom, a portal with all of our textbooks and video platforms, Google Keep for notes and Google Classroom to plan and keep track of assignments.

Adam and Skip: Do you trust these technologies, or do you feel the need to check on it and make sure everything is working properly?

Lizzy: I trust that it’s going to be there and give me the information that I need.

Adam and Skip: Google Classroom is pretty accessible. Given the choice, would you rather pick up your phone or your Chromebook?

Lizzy: I prefer my phone to quickly check assignments, but if I have to do something on a Google Doc, then I prefer to use my Chromebook because it’s easier to see and type on. And, It’s less distracting.

Adam and Skip: VR is the new, cool technology in town. How big are you on VR stuff?

Lizzy: It’s cool and all, but most of my friends don’t have a VR headset, so I can’t really talk to them or play with them on that. I have other stuff I can do with my friends.

Adam and Skip: What’s your digital life like at home?

Lizzy: We turn on the TV and everything that we want to watch is there. Sometimes we have to pay for stuff, but that’s becoming less and less of a thing. My phone, the switch and the Xbox are my favorite technologies at home.

Adam and Skip: It’s pretty normal to get mad at technology. Do you ever get frustrated with technology?

Lizzy: Yeah. I probably yell at my phone on a daily basis because something isn’t loading.

Adam and Skip: Do teens unplug or take technology breaks?

Lizzy: Some of us do, but not a lot. I feel like I need that every once in a while. I like being outside and it’s nice to get a break from technology. I really don’t think about how much I use my phone or other technology. I can see how much I use it, but it doesn’t really bother me because I am just used to it.

Adam and Skip: What do your friends think about technology controls or people watching over them on their devices?

Lizzy: I have gotten a few complaints about restrictions, especially when I run out of time on a game.

Adam: Can you explain to everyone what our deal is and how you get restrictions with your phone?

Lizzy: I usually get more restrictions when I am abusing the phone, spending too much time on it or downloading games I’m not supposed to. But, if I’m open with how I’m using my phone and my screen time goes down, then I get more freedom and my restrictions get loosened.

Adam and Skip: To wrap up, what’s one piece of advice you can give tech leaders and parents?

Lizzy: Restrictions are good because they help turn your kid in the right direction. You may think you’re being mean, but in the long run, it’s super helpful.

Just like at Humanize IT, good conversations and open communication help everything run smoothly. Thanks Lizzie for chatting with us about your take on technology! Join us next week for another episode.

Operations Vs. Strategy

Apple Podcasts: https://apple.co/2NHRRDl
Spotify: https://spoti.fi/3AyHCUd

If you’re an engineer then you might not like to talk about strategy. We get it! But, strategy is super important in any successful organization. This week, we are going to focus on how strategy is a component that we need to focus on as well as operations.

The simple fact is, strategy is not just simple planning; it’s a larger item that shows where your organization will be going someday. If you’re technical, you might not understand this. You might be someone who hears a bunch of strategic ideas and instantly thinks that none of it can be done. You might be thinking that the ideas are crazy and completely impossible.

The important thing to keep in mind is that none of these strategies and tactics need to be done tomorrow. These are ideas that are going to take time and very small steps forward. Strategy is where your organization is headed. You don’t have to get there by the end of the week!

Where your company is currently and where you will be in the future will look drastically different. You just have to focus on what you’re doing right now and then build to that future company bit by bit.

Look at strategy as the goal that your company is aiming towards, and operations are how you will get there. Strategy should be done in steps and you never have to know what the future step will be. If you’re on step 2, then do what is necessary for step 2 and slowly, step 3 will work its way to your understanding and become clear to your company. Once you’re on step 3, that can be your focus until step 4 begins to form and take place.

Another important thing to keep in mind is, while strategy is important, it’s not everything. Some people get too lost in strategy and nothing ever gets done. Those are the people that engineers hate. Their heads are always in the clouds and nothing ever happens. Operations are the day-to-day tasks that allow strategy to be accomplished. Both strategy and operations must work hand-in-hand.

The frustrating thing about strategy is you most likely will not see the fruits of your labor for months if not years. Results from operations can be seen by the end of the day. This doesn't make one more important than the other — it simply means that you have to be patient and know that both are very critical to your organization no matter the length of time it takes to see results.

In order for both of these to work together, there must be trust. People in strategy need to understand that their engineers will have the ideas and the operations people will be able to accomplish it. The people in operations need to look at the strategic people and know that they have great direction and know where the company is headed. When both work together, that’s when success happens.

In order to understand if your strategy and operations are working together, look back at your company and where you were a couple of years ago. Have you accomplished what your strategists thought would accomplish with the operations help? If not, be honest and make changes based on what you see that is working. Essentially, don’t just take steps to take them. Take steps to get where you’re trying to go.

The moral of the story: strategy is where you are going and operations are how you get there.

Talk Like a CEO

Apple Podcasts: https://apple.co/2NHRRDl
Spotify: https://spoti.fi/3AyHCUd

Last week, our focus was talking like a CFO. This week, we’re tackling how to talk like a CEO!

You might have heard the phrase: one throat to choke, one back to pat. Well, that’s the CEO of a company. They are responsible for their company in the good and the bad, for better or worse. CEO is a title that a lot of people want, but it comes with a lot of weight.

As an MSP, when you’re talking to your clients in a meeting, the CEO might be trying not to fall asleep. Don’t take this personally, their focus is just mainly on the success of the company at large.

With that information in mind, there is one sure-fire way to get the CEO on your side. Make them look good. Yep, it’s that simple. Let them know how your products and services will make their company excel.

More than half of the CEO’s job is politics — essentially, making their company look good and being responsible with their decisions. They are looking for success, which means you need to let them know how your products and services are going to bring that success.

One thing to keep in mind is that success looks different for every CEO. Just like finding success with a CFO, talking to your client’s CEO is how you can determine how success is measured in their company. It is going to be a moving target, really. You can not take one thing that is important to one CEO and assume that it is going to be the same target that the next CEO is shooting for. Having conversations with each CEO will allow you to aim for the right things.

Another important tip is to get a grip on what the company’s culture is. Knowing what the culture is will allow you to get to the table in front of the CEO seamlessly. Some companies are hierarchical where there is an order of people that you must talk to or go through in order to chat with the CEO. Go through that process and be respectful of the way their business is structured. Other businesses are more of a level playing field and it’s okay to go directly to the CEO or upper-level management. Just be aware of that culture and go through the process of communicating accordingly. If you don’t, the CEO will be much less likely to meet with you at all, or they will choose to skip any meetings going forward.

The last tip we have for you is to learn the CEO’s vision for the company. The CEO is constantly going back to the basics of what the mission and vision of the company are and how you fit into that. Figure out what that vision is and put what you’re bringing to the table in that context.

A great way to do that is to go to your client or potential client’s website and write in your own words what you believe their vision is. In your meeting with the client, ask the CEO to take a look at it and make sure that what you wrote is correct. This will let the CEO know that you understand them and desire to make them look good with your solutions.

The CEO’s opinion is important, so have a listening-focused conversation, learn their measure of success, get a grip on their company culture and understand their CEO’s vision for the company. If you do all of that, you’ll be talking like a CEO and bringing success to you and your client in a heartbeat.