6 Common Mistakes Companies Make When Choosing a New Business Phone System in 2026

You work for a large company (hundreds or thousands of employees), and your phone system is end of life… so it’s time to start the phone system replacement project. 
In this video, I cover 6 common mistakes your company wants to avoid.

Which business phone system vendors should your company quote? Ask me today.

About Me

Mike Smith has been helping companies select the best telecom, WAN, security, and cloud services since 1999. He founded AeroCom in 2003, and has been the recipient of numerous business telecommunications industry awards, including being recognized as one of the top 40 business people in tech-heavy Orange County, CA. Follow Mike on YouTube, LinkedIn, Reddit and SpiceWorks.

Key Takeaway

You work for a medium to large sized company, meaning hundreds or thousands of employees and your companies in the market for a new phone system. Well, if that’s the case. I’ve been helping companies choose phone systems for over 25 years. So I’m going to share with you some information I’ve learned over the years. I’m going to tell you six common mistakes. Medium to large size companies often make when selecting a new phone system vendor. My name is Mike Smith. I’m the president. Aerocom, let’s put our heads together on this.

My Recommendations

But first, if you’d like to know which cloud phone system vendors your company should be quoting, reach out, send me an email or give me a call (714.593.0011). I don’t charge anything for my advice, and I’ve been a broker for all the major vendors in the marketplace for over 25 years. I know the industry inside and out, and I will help your company make it a lot better decision in a fraction of the time. So join the thousands of other IT professionals who have used me to help them make a lot better decision, and a fraction of the time. Send me an email. Give me a call. I’d love to help you. I will also make sure you get better pricing than if you start calling these companies directly. Also, go check out our website Aerocominc.com where you can read reviews, write reviews on providers, sort them by features and capabilities, and subscribe to our YouTube channel so you don’t miss any of my weekly videos that I put out. Leave me a comment down below. I’d love to hear from you.

1. Taking current on-prem into the cloud

All right, so what are the six most common mistakes medium to large sized companies make when shopping for a new phone system? Well, why am I talking about medium to large sized companies? First of all, that’s just my area of expertise. That’s what I work with primarily. So that’s why I know the best. So that’s what I’m going to focus on. If you’re a small organization, I’m sorry, but that’s just not what I work with, and I’m not going to know that much about those. Okay. The first mistake is trying to go to their on prem phone system vendor and ask them to quote them on a cloud phone system, thinking that it will be an easier transition if they go from their on prem phone system to a cloud phone system with the same vendor. An example would be a company that has a Cisco call manager phone system in place today. And they have again hundreds or thousands of employees on this Cisco phone system.

It won’t save money or time

And it’s on prem. They’re thinking, hey, it might save us some time and money if we just go to Cisco and move to their cloud phone system. Well, you may want to look at Cisco’s cloud phone system, which is called WebEx. So you might want to take a look at that. But it’s not going to save you any time or money by doing that. It’s not going to do that is if you’re using a wire or Cisco or Mitel or any of the other on prem phone systems out there, you’re not going to save any time or any money by going with that same vendor. For a cloud phone system. You’re basically going to go through the same exact process as if you use any other vendor, so you might as well look at it as just starting with a clean slate. Hey, what vendor do we want to use, period? Those phones that you have are not going to work with any of the cloud phone systems, even if you stay with the same vendor. So Cisco on prem desk phones for the on prem, call manager phone systems are not going to work with Cisco WebEx cloud phone systems. They’re not going to work. So you’re going to have to get all new desk phones no matter what. So don’t worry about saving any money or time. Just look at it like which phone systems should we quote, period. What are going to be the best fit for organization regardless of what kind of on prem phone system we have today?

2. Not understanding hidden fees

The second most common mistake is not understanding hidden fees. Okay, so it’s a terrible thing about our industry, but a lot of times there’s hidden fees when cloud phone system called business phone systems quote you and it, they quote you their per user license fee and then that’s it. But what you may not know to ask is there’s also some hidden fees in there, like for instance, cost recovery fees per user and E911 fees per user. A lot of times it adds up to about $5 per month per user in additional hidden fees. And not every service provider charges those. Although the sales reps might want to tell you that that’s not true. Not every service provider charges an extra $5 in additional other charges on top of the license charge. So something you need to know there. But a lot of times customers get blindsided by that honestly, because the reps aren’t being forthcoming with that information.

3. Not looking into long-term viability

The third mistake is not looking into long term viability. It’s just looking short term like, hey, this vendor offered something really good and we like what they’re offering, but not really looking into what’s the long term viability of this vendor. Are they going to be around in five years? How do we know that? What are the tangible things that we can bank on that tell us that this vendor is going to be around for at least five more years, because the last thing you want to do is sign up with a new cloud phone system vendor, and within one year, they sell their company to another large company that large new company, grandfather, is the platform that you’re on and doesn’t touch. It doesn’t invest in it, doesn’t put any R&D into it. So then within a few years, you’re on an old, antiquated system that doesn’t have any of the latest and greatest features on it. And then that vendor’s trying to call you and tell you that you want to migrate to their cloud phone system. So you want to avoid that if possible. I mean, it’s technology, so you can never know for sure what these companies are going to do. But there are some indicators that you can look at that will tell you something about the long term viability of that vendor. If you want to know what those indicators are. Reach out and contact me. That’s something I can help you with.

4. Not doing a PoC

The fourth mistake is not doing a free proof of concept with the vendor that you’re looking into, and sometimes you might want to do dueling proof of concepts too at the same time or two back to back that your top two vendors. So a lot of vendors offer this. It’s called a free POC proof of concept. And what I recommend you do is don’t just do it with yourself. You know, just don’t within your IT department. Hey, here’s a couple IT guys and give them. They’ll usually give you 5 or 10 user accounts to use for a couple weeks. Well don’t just hand them out to other I.T professionals. Hand them out to power users and important users throughout the company and different departments. Because what that’ll do is it’ll help you get buy in from those folks, because there’s no way in it that you know what everyone else, everyone uses on the phone system every single day, every feature that they’re using, all that good stuff. The last thing you want to do is put this whole decision on your shoulders, make the call, and then all of a sudden get a bunch of complaints. Once it’s installed, go and, well, hey, I can’t do this anymore. I can’t do that anymore. And you’re like, well, you never told me that you do that. I didn’t. I had no idea you use that as a feature. Well, this is a way to avoid that is get other people involved on the proof of concept and get their feedback on the new service provider. It takes some extra time, but it helps make a lot better decision in the long run.

5. Devaluing new technology

Another mistake I see companies making sometimes is they’re devaluing technology, like companies will call me and they’ll say, hey, we have an old phone system, but we don’t need any fancy technology. We just need to answer, transfer voice mail, you know, just have those features and that’s it. All we want to do is phone calls. That’s all we need to do. And we barely use the phones. Well, there are some rare cases where that is really all that your company needs, but don’t automatically discount the new technology out there because some of those new features can help your company, even though you think all you need is answer transfer voicemails. Sometimes there’s a couple little bonus features that a few employees might like. Like, for instance, sending receiving text messages from their main number. Maybe they’re sending text messages today on their personal cell phone, and they hate it because now they have two phone numbers floating out there, and then customers are calling them back on their personal cell phone, and yet they want them to call them on their company, you know, landline. And yet they’re getting voicemails on both different phones and text messages on one phone and voicemails on the other. It’s a mess. Well, maybe they want something miss on their business phone number, or maybe they want.

AI Call Summary & CRM

AI call summaries on every call that they’re doing, so every time they have a phone call, I give them a call summary with next actions little, you know, ticker list of like here’s here’s the, you know, next actions that we want to do after this phone call. So maybe they’re driving and taking a call on their mobile phone. They don’t have any way to take notes. Well I is going to give them a call summary and tell them like, hey, here’s here’s the action items from that call. And here’s a call summary so they can search the call summary. They can look up information on that. So cool. New technologies that are out there that they may want to take advantage of that maybe you’re just not thinking of maybe the maybe the IT department isn’t going to use, or maybe sales is going to use. Maybe marketing is going to use it, maybe operations. Who knows? Other features out there or things like CRM integration. Maybe you want to integrate with your CRM so that automatically every single calls logged in the CRM with customers and that call summary is put inside the CRM as well. Maybe that’s beneficial to management or the executive team on some level, especially as AI comes into play. Maybe you’re maybe five years from now your company gets an enterprise AI solution and you want to ask it, hey, who are our top customers? Are we in touch with them? Are they happy with us? Well, they’ve got to get some information somewhere. And some of that is coming from the phone system.

Teams Plug-in

So you want to have a nice way to summarize that. So integration with your CRM might be something useful that you may not be thinking of, but that might be a useful tool within the. Next five years. As enterprise AI becomes more popular. Also, Microsoft Teams plug in. Hey, if your company is using Microsoft Teams for instant messaging and conferencing, but you maybe don’t want to use teams phone system because teams phone system isn’t quite, budget friendly, it’s a little bit too expensive. And and you’ve heard it’s got some feature gaps. Well, maybe one of the service providers out there offers a teams plug in where you can integrate their phone system inside Microsoft Teams. So features like that. So don’t always say like, hey, our company need is a super basic phone system. We don’t need any features. You never really know. You want to dive into that a little bit. And if you want to know some of the features you should be thinking about and additional ones I talked about, reach out and contact me. I can help you with that.

6. Over-valuing Teams

And last but not least, the last common mistake I see speaking of Microsoft Teams is overvaluing Microsoft Teams phone. So some companies call me and they say, hey, we want to get team’s phone system because we use Microsoft Teams for a lot of stuff. We we do all of our instant messaging on teams, and we do all of our conferencing on teams. So it just makes sense to us to to pile on some system. On top of that. So we had just one app, one app to support, one app to use for all that stuff. It just makes sense, right? Well, kind of yes. Kind of no. So sometimes teams is a great fit for teams. Phone I sell a lot of teams phone system to my customers, but sometimes teams is not a great fit and a company is really pushing for teams phone, but in reality they’re really putting too much value on putting everything into one app because there’s major feature gaps with teams phone, for instance, those I call summaries that I just talked about a little bit ago. Teams doesn’t have any of that. So you can’t do I call summaries included for free. I mean, you have copilot, but copilot is not with teams phone and you got to pay extra for copilot. Some companies offer that I call summary included with their standard call packages.

Teams Phone Feature Gaps

Also call analytics getting call analytics teams phone isn’t good at that. So if your company needs call analytics, if you have a lot of salespeople making a lot of sales calls, you need some extra features that teams phone is not going to offer. So don’t think that teams phone automatically, because it’s just a single app is going to be the best way to go. There might be some major feature gaps that really trump the advantage of having a single app. Yeah, single apps, great and everything, but we lose out on all these new technology features that can really help our company and help give us a better customer experience, help our salespeople sell more all kinds of good stuff. Also, integrations teams often is not good at integrating with a lot of the different software applications out there. So maybe your company needs to integrate a little bit. And lastly, cost teams phone unless your company already has E5 licenses. If your company has E3, E1 Business Premium, Business Standard, if you have any of those normal licenses other than E5 teams, phone is actually going to be your most expensive phone system option in the marketplace if you’re a medium to large size company. So something to think about. Teams phone is a good fit for some organizations, but for a lot of organizations, it’s actually not a good fit and some most expensive option on the table. So definitely want to look at teams phone with a grain of salt and really evaluate it in depth. Really get into the weeds on it.

Which business phone system vendor should your company quote?

Speaking of which, if you’d like to get into the weeds on any of this stuff, reach out, send me an email or give me a call (714.593.0011). That’s my job. I’m a broker for all the major cloud phone systems out there, for businesses, for medium to large size companies. So if your company has 50 or more users, that’s really my sweet spot. Again, I’ve been doing this for over 25 years. I know the industry inside and out, and I can tell you based on what your company’s requirements are, which vendors your company should be quoting, and which vendors your company should be avoiding. I can introduce you to the best salespeople to work with at those organizations. I can also oversee the coating process to make sure you get much better pricing from the vendor of your choice, as opposed to you calling them and getting quotes directly. And on top of all that, I don’t charge you anything for my broker services, if you use me, you won’t pay a dime because the service providers actually pay me my broker fee. So there’s no excuse not to at least reach out and get my opinion on this stuff. So send me an email. Give me a call. I’d love to help you join the thousands of other I.T professionals who have used me to help their company make a lot better decision in a fraction of the time. All right, don’t forget to watch my or subscribe to my YouTube channel. So you don’t miss any of my weekly videos that I put out and go check out our website Aerocominc.com Thanks for watching. I will catch you on the next one.