How to outsource a critical service: one of the hardest (and best) business decisions you'll ever make

Date Posted: May 18, 2022
Tressa McLaughlin

Outsourcing critical processes to an outside resource can be nerve-wracking. It’s hard to know who to trust. It may involve more time and more cost than you originally planned for. And, it’s absolutely necessary if you want to grow. 

The outsourcing decision that made the biggest impact for us was handing off our day-to-day IT and server maintenance to a company with that expertise. Before that, we always relied on an internal person to manage a server, stay up on the updates of the server and keep up with all the software. We didn’t have anyone internally who had the expertise, so we kept shuffling those responsibilities from person to person based on who we thought might have an interest.  

The whole process was really disjointed. We were always in a scramble. We were always behind, because one of us had read an article or a blog, or someone had heard of something we thought we should implement. Lifting that out of our company and handing it off to an external expert helped us with soft costs and eliminated a lot of the things that we were behind on or were having to figure out on our own.  

Doubts and questions: what does it really take to outsource? 

A lot of my questions going in were around the actual true costs. A lot of times you get a quote from a company based on what you think you know, and a lot of unexpected details come up because you’ve done it internally for so long. You have issues you didn’t even know needed to be resolved. 

I was concerned that the monthly cost would be higher than expected. I was also concerned with whether our team would receive the level of service that they deserve. And I was concerned with whether all of the different platforms that we rely on would come together and work well. 

I had doubts that an outside company could understand our business and our workflow, why these pieces are so important, and who could help us bring them all together and simplify them. 

How many of those questions and doubts ended up being an issue? 

Every single one of them. Every single one.  

Anything that I had a doubt or a concern about did come to fruition. Nothing was as easy as it sounded. I can make things sound easy when I'm in my field of expertise. However, I know that I'm still going to encounter challenges. How can you work through those? When I'm in my expertise, in my zone, it's easy for me to do that. So I was counting on that from the IT company. 

How to navigate outsourcing challenges 

I got through those challenges by asking a lot of questions, staying in the sweet spot of the conversation, and focusing on working towards a solution.  

  • I understand you can't do this. What can you do?  
  • What are your suggestions?  
  • What would you do if this was your company?  

Also, if there was a hard no, something that’s non-negotiable (like a core piece of specialty software I knew we were not going to change) the solution was to get the two people together that could make it work and step out of the conversation myself. Let the experts work out the details and give the results of what needs to happen. Getting the experts talking to each other worked really, really well. 

Stepping back from the details  

It was a relief to step back from being part of those conversations, and it was also scary. We're talking about the backbone of our business. We need our IT up and running or we can't take care of customers. So, this outsourcing decision was a big leap of faith, even though we had vetted our choice carefully. It's still a big leap of faith to say, okay, I trust you that you're taking the thing I need to run my company, and you can make it work in the timeframe that you say, and it will actually be better. Scary.  

How do you navigate that fear around outsourcing? Communication.  

Ask for check-ins and milestones all along the way. Where are you in the project? What’s coming up? How are you resolving it? When can I expect an update? Keep that process moving. 

Information is power, and knowledge is one of my company’s core values! I work best when I'm informed. That doesn't mean I have to do the thing. I just want to be informed or consulted. That’s what gives me confidence and trust in the solution. 

How to handle the unexpected challenges that WILL come up 

There will always be more to the project than you know setting out. In our case, I suspected but didn't fully grasp that we were not as current on our software versions as we should have been. And that meant there was a lot of back work that needed to be done to get us up and current just so we could get on the server. It also made us realize how much not having the latest tools might be holding the team back.  

I kept thinking, were there things that maybe Microsoft had updated that would've been great to have? And then I also had to self-reflect and say, where was I complicit in that? Why did I not know that?  

But ultimately, it turned out really well, one of the best outsourcing decisions I’ve ever made. It was painful, but a lot of good things are painful. 

Why finding the right outsourcing partner is completely worth it  

Some of the benefits of outsourcing are obvious. I expected that we would forklift a huge responsibility off of our team and put it in the hands of an expert. By doing that, you’re going to free up time, remove stress, and free up a lot of unnecessary energy going into things that are beyond your scope.

I also expected that we'd be faster. Our tools would be faster, and we could work from different locations rather than all being tied to the building.  

I expected that our outer offices would have the same quality of experience with their IT as we did at corporate. That was always something that bothered me – I felt we were under-serving their needs, and that's not where I like to be as a leader. 

We also had benefits I didn’t expect. Yes, we did have to replace a lot of equipment and we did have to update some software, which had a financial cost. But by doing that, we saw something unexpected: our team just felt better. They could accomplish their work and tasks much more effortlessly, without the extra energy it takes to do workarounds, things like restarting their computer several times a day or copying and saving in multiple places.  

When you’re handling tasks internally that should be outsourced, you end up expending a lot of extra energy on workarounds and inefficient processes just to keep all the plates spinning. It is 100% worthwhile to hire an expert company… Share on X

How do you find the right outsourced service provider? 

My best advice: do your homework. Get references, ask about projects they've done with companies your size or similar. Ask about what worked well and what could be improved. Ask the company, and ask their customer references. I think you'll get a lot of information that will tie the pieces together so you can feel confident moving forward. 

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