Managed IT service is foundational to all businesses these days. Whether your company’s technology is in the cloud, hosted in your office or somewhere in between, it is critical to find the right Managed IT Service Provider so your organization gets the most from its IT investment.

We know how it is. You start an IT relationship with high hopes that the partner can take the IT tasks off of your plate, elevate your company’s experience, and give you time back to do your primary job. Somewhere along the way this falls short and you spend too much time managing and defending the relationship. The expectations plummet and you end up just hoping they respond to support tickets on time.

If this sounds familiar, you are not alone. At Ripple we have helped hundreds of companies in a similar position. 

We developed this guide to help you find the best possible IT service partner for your company. Get your time back and get the IT experience that your company deserves.

5 Key Elements to Consider When Choosing your Next Managed IT Service Partner

There are few decisions that will affect your company as substantially as switching your managed service provider. IT is at the core of almost every business, and choosing a great IT partner makes all the difference.

Would you guess that most managed IT service providers do about 90% of the same stuff? It’s true! We use the same tools, implement the same hardware, and suggest the same software.

With so much the same how can the results be so different? Why can one managed IT provider be great and another not-so-great if they are 90% the same? This is where it gets interesting. 

Managed IT glory or ruin revolves around 5 key elements. Deciding which of these 5 elements your organization might be lacking is important to know before making a decision.

Before we get into those elements take a deep breath and decide what this decision is about. 

It is about helping you win, right?

Win back your time.

Help your coworkers win by eliminating their technology issues.

Position yourself and your team for success.

No matter which win you are going for; this guide will simplify the IT buying experience. Focus on these 5 elements to get you there.

These Elements are: 

  1. Philosophy
  2. Daily Execution
  3. Consistent Support Experience
  4. IT Strategy
  5. Security

Philosophy – Do you align with their approach to managed IT?

IT managed service provider became the in vogue term for IT companies to use in the mid to late 2000s. 

Prior to managed IT we were either IT consultants or IT support companies. Both handled the standard function of support but beyond that the approaches were vastly different. 

Consulting companies

Worked very closely with a handful of active clients. Often being involved in decision making and strategy (e.g. suggesting and then migrating your email server to the cloud). 

Support companies

Were break-fix style firms specializing in firefighting. They successfully came to the rescue when a client was most in need (e.g. all-nighters getting a crashed mail server back online). In addition projects were executed as their clients identified the need. 

They each associated their value to something different. Consulting companies hung their hats on the relationship and transformative results they delivered for their clients. Support companies on the other hand pointed to their record of heroics as the key value to their customers. 

The evolution of the industry shifted us from hourly services to fixed fees and contracts. During this time, a new generation of tools were brought to market. The intent of these tools was to make the service more proactive and ultimately better for our clients. So the Managed Service Provider (MSP) was born. Ripple was one of the pioneers in this process completing the conversion to MSP in 2004. By 2008 most of the IT companies in the space were now using the term MSP to describe their businesses. 

In theory the idea of an MSP sounded great. However in practice, the name and structural change did not change most companies’ philosophy and approach. This is why understanding these are so important. How do you go about doing this?

Here are a some items to listen/ask for during the sales conversation:

  • Can they simply state what results they will deliver for you and your organization?
  • Do they use a lot of adjectives to describe the service they provide?
  • Do they use results, process and methodology to describe the service they provide? 

Look for simplicity and objectivity here. The more subjective or adjective based the discussion the less likely the service will match. 

  • Is their discussion and discovery focused on your infrastructure or people?
  • Do they outsource any functions? Why? Where? 

The best result an IT company can provide your organization is always helping your people get more work done. Focus is a large part of that. If the MSP doesn’t focus on your people or are not in control of the experience. This can have a negative impact on the success of the relationship. 

  • If nothing changes in your environment (you had no service complaints and you did not ask), how often would someone reach out to you and/or schedule a meeting to speak with you in a year? 

You will commonly find that after on-boarding there is a reluctance to come on site or meaningfully engage with your organization, outside of the support experience. This all boils down to the MSP support business model. You want to look for a more consultative IT partner. Specifically, a partner with a set process and schedule for engaging with you outside of the support experience. 

Does the approach of your IT partner align with what you and your organization need to win? 

Daily Execution – Do Your Job!

Execution, a sophisticated term for getting stuff done, is the next key element to choosing the right IT partner. 

You can survive without good strategy for a while before it rears its ugly head (more on that later). Execution is non-negotiable because without it, everything falls apart right away. It is at the core of everything the IT partner will do for you, so it’s important to evaluate.

Remember how 90% of IT companies are doing the same stuff? Execution largely falls into that 90%. But the other 10% is what makes the difference. 

Review your current situation and ask yourself a few questions:

  1. What challenges you about your current relationship? 
  2. How much time does it take in your day to manage the IT relationship? 
  3. What did your last inquiry into a service issue look like? Who did you talk to? 
  4. How did the last project that was completed go? Would you consider it successful or did it just get done? 

With your current situation in mind you can evaluate if the prospective IT partner will be any different. 

Typically size and structure will dictate this. If you are looking at companies with a similar size and structure as your current IT provider; then the chances of the execution being different over time is less.

For example, an IT partner that has 15 people or less typically has a one technical person that is 100% involved in your support requests. In addition they do much of the relationship management and project work.

This is not ideal for a lot of reasons but let’s look at a specific issue. Consider the example of a bad user support experience.

The flow looks like this:

  • Your teammate has a poor support experience
  • Your teammate has no outlet for the frustration caused, so they remark to co-workers about the experience
  • Another teammate shares a similar experience
  • Someone gets fed up and talks to you (because you manage the relationship) 
  • You initiate a call to the provider 
  • After lots of back and forth you set a time to talk with the provider
  • Conversation happens and promises are made
  • Service improves (or doesn’t) but eventually everything goes back to the way it was

If you only work with one person, can you really give candid feedback? Is every let-down worth the friction that it will cause when there is only one person? 

Now contrast this with a mature IT provider, where at the bottom of every support ticket is a survey link for instant feedback. In addition, quarterly there is a longer form survey sent out to each user to provide feedback. It’s an important mechanism to start getting real-time feedback that can be acted upon. With a larger team, your feedback can be heard and acted upon without any one person bearing the emotional brunt. You can give candid feedback, and the team can fix the process that led to the feedback.

How would this change the user’s experience above and yours?

If getting back your time and having a less frustrated team is important to you – you win!

If your standards for execution are not higher than just “getting support” than you are being under-served.

A Consistent Support Experience is More Important Than a Great Experience

Support is the single most used function in a managed service engagement, so it should get a lot of attention. Why is a consistent support experience better than a great one?

Obviously a consistently great experience is the best of all. But an inconsistent experience punctuated by occasional heroic greatness is costly – and unfortunately very common. It’s a product of well-meaning people, traditional IT hero-culture, and ill-defined process.

Can you tell why consistent is more important than great when it comes to this core function? 


So can you simply ask a prospective partner, how consistent is your support? Perhaps, but it’s better to look for strong proxies of consistency.

There are many, but here are a few:

  1. How long has the IT service provider been around?
  2. How long have the majority of your clients been with the company?
  3. How long have your support personnel been with the company?
  4. What is your average time to resolve tickets?
  5. What is your average response time to tickets?

Time is the critical return on your investment from a managed IT provider. Your team can now focus on their most important work. – Win!

IT Strategy – Where are we today?…Where are we going?…Why does it matter?

“IT strategy.” This is by far one of the most overused yet under delivered parts of a managed IT services engagement. Every managed IT provider knows they have to say strategy, but what is it really? 

How does the IT strategy show up in sales conversation and then later in the engagement? 

Quarterly Business Reviews or a QBR are the typical proxy for strategy. If the IT service provider is mature enough you’ll also frequently hear about a virtual Chief Information Officer or vCIO. 

Having a regularly scheduled meeting with your IT partner is a good thing for a lot of reasons. But a regular meeting is not strategy. Quarterly talks (if they even occur) almost always default to being tactical in nature. Typically these discussions are used for reviewing the latest service tickets, security scans, and what needs to be bought or upgraded. Does that sound strategic?

The term strategy means, a plan of action or policy designed to achieve a major or overall aim.

Major or overall aim…it is much bigger than day to day, quarter to quarter or even year to year.

How are you and your organization going to win? 

When looking at IT strategy we like to boil it down to this:

Where are you today? Consider:

Are you serving your customers in the best way possible?

Are you hiring the right people? 

Are your people free to do their best work? 

Is your new employee onboard experience helping retain your people? 

Are the tools you use enhancing the experience your customers and employees have?

What challenges do you face and is there a plan to overcome them? 

Where are you going? Consider: 

What challenges are we going to have to solve in order to get there?

What does an IT road map look like that can help us win? 

What does success look like from an IT perspective in a year? 

If being led from a technology perspective is important to you. Then get a huge organizational win by finding a partner that can lead you.

Security: The CEO has been Phished…

Did reading that make you shudder or remind you of a horror story you heard from a peer? 

Security feels tactical compared to stuff like philosophy, strategy, execution. Surely every managed IT service company includes it. Yes, most responsible IT companies include some form of security in their solutions. But the 10% here makes an enormous difference. So security makes the list.  

Consider this, 43% of cyber crime is targeted towards small and medium sized businesses. In addition, since the Covid-19 pandemic started the FBI has seen a 300% increase in cyber crime overall.

Make no mistake, if the IT service company you choose does not have a solid process for securing your organization no matter where your people work (in or out of the office), then you are likely to be calling them about an incident within the next year. 

So how can you assess who has a comprehensive plan? In addition to the tools, check for 5 additional things:

Ease of Use

Nothing derails security faster than a poor user experience. If the prospective IT partner does not address this (which they absolutely should). You need to get specific enough with them to understand what your users will likely experience.  It’s not security if everyone can’t use it.

Secure Experience From Everywhere

Will the entire security capability follow the user when they are out of the office? Does it require too much from them? Covid has forced a new normal with remote work being common. The old way of securing the perimeter of the office is no longer a viable strategy. Making sure security is no longer dependent on your physical office is critical.   

Non-Technology Based Solutions

A lot of the value from an outsourced IT partner comes in the form of exposure and experience. They should be able to educate you on best practices they have seen and developed as part of the security effort. A simple example of this is a double (electronic and voice) verification/authorization process for all wire transfers. 

How Do They Secure Themselves?

Your MSP’s tools and access represent a large potential security hole in your environment. If they are not implementing security best practices themselves, then working with them increases your risk rather than lowering it. 

Are They Willing to Compromise?

Security is a commitment not just a suggestion, it is only as strong as the weakest link. Typically the largest push back on security comes from the executive suite at a company. Understanding how a potential IT partner will navigate that is crucial. Do they make exceptions for the executive suite? Or instead do they stick to their commitment and work to get the executive suite onboard? Are they equipped to help you persuade executives? When security and strategy are your goals, you need a provider that can work with your team as a partner, not a  vendor. If that shift does not take place then accomplishing this goal becomes very difficult.

Find an IT partner that can deliver the technology and address the other key aspects of a strong security stance. Once you do the chances that you will need to pay a ransom or report to your clients about a security breach go down tremendously. – Win!

In Short..

So there it is! You now have 5 key elements that will help you cut through the noise. Now you can actually evaluate your next managed IT service provider on the critical 10% rather than the table-stakes 90%.