Talent acquisition and retention are top challenges for businesses in the Chicago region. As such, a top priority of the Chicagoland Chamber is supporting businesses’ efforts to find and engage the talented people they need to drive growth. We are proud to publish this content, which is authored by the CEO and Founder of the Chamber member Steadfast.


 have heard from many managers and owners of small and midsize enterprises (SME) that they don’t feel they have the expertise necessary to identify and hire good IT people, or they’re having trouble finding enough good IT talent. At this point in time, IT is critical to almost every business. The data and communications your IT team is responsible for can be the heart of your entire business, so failing to have the right IT experts can be a major problem. With 20+ years of experience in the IT space and seeing these things across hundreds of businesses, here are my key points of advice to address these issues.

1. Hire for passion

You can train skills, you cannot train passion. Technology is constantly changing. There is always something new. Someone who has gotten all the certifications with just the purpose of getting a job may not have the same passion for learning once he or she already has a job. There are a lot of people who got into technology just to make money, not because it is a passion. Find people for whom IT and technology are a passion, who will want to learn more on their own and see new projects as a challenge and an opportunity to learn.

Ask about what got them interested in technology, the technical solutions they found that they are most proud of, or what projects they have simply done on their own.

2.    Keep your options open, let yourself be surprised 

Don’t limit yourself in your requirements or expectations from candidates. If you’re already having trouble finding good people, how will limiting your pool even further help?

The most common restrictions I see being placed on people are requiring a college degree or a very specific set of experience. If someone has the 5+ years of systems administrator experience you’re looking for, does it really matter whether he or she has a college degree or not? A lot of good IT people are self-taught, and those people can be amazing employees, as they’re often the ones with the most passion (see item #1). Additionally, you can’t expect that someone is coming from an environment just like your own workplace. He or she will need to be able to learn no matter what. So, why would you expect this person to already be familiar with every single system, application or programming language with which you work? List those things as recommendations, as nice-to-haves — not requirements, unless you do have a very specific need.

Additionally, IT job descriptions and responsibilities can vary wildly between companies. Someone’s resume may make him or her seem underqualified or overqualified based on job title, but you really need to dig into what this person’s specific role was. A network engineer at one company might have been involved in the planning, architecture and troubleshooting of the company’s entire network. Yet at another company, she might have only done base switch configurations based on a template. Be wary of requiring an amount of experience based on just a title. There are probably a lot of people out there with the experience you really want, just not the title. There are just as many people who have had the title, but not the experience you want.

Keep your mind open when looking for candidates, don’t shut out potential opportunities.

3. Do not fall for “buzzwords” or “experts”

It is easy to be impressed by people who seem to know technology at a level that is over your head when they use buzzwords you’ve heard before but don’t understand. It can make you feel stupid. So the other person must be smart, right? Don’t be fooled. The use of buzzwords is not evidence of knowledge, and it is common for IT people to speak this way to mask a lack of actual knowledge. It is up to you, as the one doing the hiring, to make sure they really know what they’re talking about. If they’re using jargon, be direct and upfront about it. Ask them for clarifications, repeatedly. Ask them what they mean, to explain more. Make them explain things to you until you fully understand what they’re talking about. If they cannot make the technology they’ll be using understandable to you and other team members, how are you ever going to be able to manage or understand their work? If they cannot simply explain what they’re doing, or the technologies involved, that is a clear indicator that they don’t really understand it that fully. There is no excuse for an IT person to be speaking over your head, about anything. If he or she truly understands it, he or she should be able to talk to you about it in plain, simple language that you understand.

A person who uses such buzzwords or talks over your head is often the type of person that claims to be an expert in everything, or someone who would give themselves a 10/10 in knowledge of a technical topic. Any truly smart person in technology knows there will always be more to learn and that one person cannot know everything. You want someone who knows and understands their limits and is open to learning more — not someone who already thinks they know everything and is infallible.

4. Hire generalists, not specialists

As an SME, you need to be able to do a lot, without a lot of people. In a large enterprise environment, IT workloads can become extremely specialized, where someone will work on just one application or system. This person knows that one thing like the back of their hand  and is a true expert, but likely knows nothing about the network, storage or other systems it is connected to or dependent upon. While this is efficient in a large enterprise that employs many thousands of people, it is not very useful for SME’s, which can’t hire as many people. What you need are IT generalists; people who understand many aspects of technology and how those things work together.

I have seen it happen way too many times that an SME hires a very experienced IT person from a large enterprise. The SME is so excited to find someone so good and qualified. Then everything falls apart. Why is that? The IT person had spent 10 years working on one thing, in one environment. The IT person didn’t know or understand how everything worked together or really anything outside of their specific domain. When looking at resumes, look for people with diverse experience, who have worked in several environments and systems by having been on multiple different teams in a company — or have worked in a service provider or consulting role where they’ve had to work with many different systems across different customers. If you’ve already listened to item #1 and found someone passionate, your new hire is also more likely to have broader experience due to a thirst for more knowledge.

5. Set priorities, and hire for those needs

While you should hire a generalist, that does have limits. One of the most common issues I see is a company will say it just “needs an IT person.” When hiring, there is not just an “IT person” job listing you can put out there. There are many diverse skills and needs in the IT space. Are you looking for a help desk technician or desktop support person to help your employees with day-to-day technical issues and support such as installing software, fixing a broken workstation or helping individual employees to better utilize their software? Do you need someone to manage your internal servers, storage, security or network? Do you need a cloud architect? How about managing an overall IT plan or strategy to improve the production and efficiency of your entire business?

All those different facets require different skill sets, and different IT people will have different skills. You cannot count on any one person having all the skills you’re looking for, so you need to fully understand your needs and have those prioritized before you even begin your search. There are also, then, different ways to fill the needs based on the priority of each need.

Make sure your job description is written for your biggest needs and focused on those needs. If you write your job description across numerous different needs and skill sets, you’re not going to find anyone. You are not going to find a systems administrator or network engineer who is good, and has 5+ years of experience, who is also going to want to do desktop support. You are most likely not going to find a network engineer who is also a software developer.

6. Utilize vendors or consultants

From item #5, you’re probably now seeing that you cannot count on one person to fill many gaps across different skills. And if you’re an SME, you probably can’t hire enough people to focus on every need you have. So how do you get past this problem? Work with vendors or consultants that can help you fill gaps.

One clear example is here at Steadfast. What sparked me to write this post was a recent conversation I had with a company looking for an IT person. The company needed someone who could do all the desktop support for its employees. But it also had needs for infrastructure management, systems administration and cloud architecture. All those needs were important, but the biggest workload was around the desktop support. This company couldn’t find any one person to meet all its needs. No one who knew enough about infrastructure management, systems administration and cloud architecture was also willing to do that much desktop support. The easy solution, then, was to split those into two roles, and keep the total budget the same as before. With splitting the role, the company could find someone to start within a couple weeks, while saving $15,000 per year on salary and benefits, as this person was only dedicated to doing help desk support.

And what about the other areas of expertise? The company worked with Steadfast, where it could access our systems administrators, network engineers and cloud architects when it needed them as a part of its overall IT infrastructure spend. All this additional support and expertise came at no additional cost over its options with Amazon Web Services or Microsoft Azure. In the end, the company quickly found the expertise it needed, had access to the expertise it needed, and saved money.

This doesn’t happen only with Steadfast. A lot of IT services providers and consultants can offer vast amounts of expertise, either as a part of their base services or on an as-needed consulting basis. Just remember: don’t pick your vendors based only on price. Find the ones that can take things off your plate and allow you to focus on your core business. This belief is why my company’s motto is “Strengthen Your Focus.”

To read more and see video about Karl Zimmerman and the founding of Steadfast, click here.