Looking to gain more clients or improve staff retention? A well-planned and implemented IT strategy can help improve all kinds of business outcomes. But first, it’s imperative to have the right IT partner or Managed Service Provider (MSP), in order to reach the outcomes you and your organization desire.  

Think of a sound IT plan as the equivalent of using good navigation software on a trip.

An MSP is like Google Maps:

  • Knows where you want to go.
  • Understands what mode of transport you are using (car, train, bike, etc.)
  • Regularly monitors the environment for changes and challenges.
  • Updates your plan based on the changes and mode of transport.
  • Describes the value of the updates to you before you accept it. 

Your MSP should deliver IT strategy pretty much the same way. However, if you choose the wrong MSP, you may find yourself moving in the wrong direction or not moving forward at all.

Here’s How the Wrong MSP Can Hurt Your IT Strategy: 

  • Doesn’t value your relationship – The MSP views your partnership as an opportunity to sell you more stuff in their “stack” rather than enhance your business.
  • Lacks interest in your business – The MSP does not take the time to understand your business, personnel, and other specific factors that must be considered in the IT plan. 
  • Sticks to static or outdated plan – You get an initial “IT roadmap” when you first onboard with an MSP and that plan doesn’t get reassessed regularly. Instead, it just gets bloated with the “technology de jour” (i.e. next generation firewall).

This is why you should take a good, hard look at your current MSP and figure out if they are the right fit for your business. On a serious note, if you have to ask your MSP about strategy or enhancements, you may be in an unproductive partnership. On another note: if a reactive relationship is valuable to you, this blog probably won’t be.

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However, if you have a proactive working relationship with your MSP, here are 3 questions that, if answered, will help better align your IT strategy. 

1. Where are we now?

This question is absolutely the foundation of any relevant IT strategy. You can’t follow any kind of roadmap if you don’t know where the starting point is.

The unfortunate part is most MSPs answer this in context of your technology, systems, and security. Worse, they may answer it while referring to (and promoting) their IT products you’re currently not using. 

Now, your current technology setup does have some relevance in the discussion, but starting in a less technology-centric place usually leads to a better-aligned plan. Asking yourself the questions below can help you pinpoint where you are today: 


  • What are the business goals for the next year or 3 years? 
  • Who are our customers and are we serving them in the best way possible?
  • What are the challenges we face? 


  • Are we hiring the right people?
  • Does the team have what they need to support the customer or business goals we have?
  • What functions do they perform?
  • Are there challenges that need to be addressed?


  • How do we hire and onboard? 
  • Are these experiences helping or hindering our ability to reach the business goals?
  • How do we retain talent/clients? 
  • How are we attracting new customers? 

By working through the above questions, you should start to get a sense of what challenges your business faces and what potential solutions could look like. Sharing this information with your MSP will allow them to tailor the IT strategy to business needs that have been clearly defined by answering these questions. 

2. Where are we going and why

Most MSPs are excellent at the “where” question. They have all kinds of technology in their repertoire they want to sell you and they’ll insist that this technology is where you need to be.

The “why”? Not so much. Mapping initiatives to value is where the rubber hits the road. Many times the default justification is cost savings. While cost savings are nice, it’s a tactic you mainly use for optimizing expenses. So, maybe challenge yourself to think of IT as an investment rather than an expense. 

What? View IT as an investment?! Yes, there is a mindset change when you do this. Whenever you invest you expect return on that investment. In the case of an expense there is no such expectation. So in this context, where could you get the most return for your IT investment? 

Easy. It boils down to people, clients, and processes. Armed with the information from the first question, you should be able to work with your MSP on finding the right initiatives that directly map to your business value.

Congratulations. You now you have a plan that is value-based. Is it time to start grinding through it? Not yet. You have one more question to answer. 

3. Is this still relevant? 

Situations change. Your company’s needs shift. And sometimes the universe throws you a curveball.

Your newly laid-out plan might be great for right now, but it needs to be reviewed regularly. In our experience, a monthly check-in is a great way to make sure the plan still aligns to your business goals. 

Remember March 2020 when the Covid-19 pandemic shifted everyone to a remote work environment almost overnight? This is a great example of why you need a regular reassessment. Imagine a company with an initiative of enhancing their environment security by implementing a next generation firewall. Thanks to the pandemic, they would need to rethink this move. If no one is in the office anymore, securing it does less to accomplish their goal. Instead they would need to pivot to a zero-trust, host-based agent so security follows each employee no matter where they are.

Another example would be a company experiencing major growth or an acquisition. An initiative that was lower priority before, like user onboarding or cloud-based file sharing, might all of a sudden be thrust to the top of their list.  

This is why a good monthly or quarterly meeting discussing your IT strategy with your MSP should be a permanent part of your process. It’ll allow for modifications to your IT plan so it remains on track with your business needs and goals. 

Next time you discuss your company’s IT strategy with your MSP, bring these three questions (and answers!) to the table and watch how relevant and valuable your IT plan becomes moving forward. 

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