The Top 5 IT Team Challenges

I’ve spent a lot of time working closely with Customers and this blog post aims to summarize my most valuable learnings from those interaction in the hopes that it will help others with their Customer Relationship Management!

My time with the Customers gave me a front row seat to various IT teams ranging from those that consider themselves inadequate (⚠️ SPOILER ALERT! ALMOST everyone thinks/knows that they have some issue - organizational silos, lack expertise, lack leadership, lack discipline or lack organization skills. Based on my observation, you’ll be glad to hear that no one is perfect! ) and with those that know they are a big deal. I’ve had plenty of time to observe what works well and what didn’t work well within a team.

The 5 common problems that you’d see in most IT teams ranging from the biggest to the smallest, from the most organized to the most chaotic are provided below. Additionally,thoughts on ways to address these challenges have been shared below

1. Testing Discipline

Chances are that your team is understaffed, overworked.. or plain lazy!


Bad Mood

Do you often catch yourself saying

  • “We don’t have an UAT, we do our testing in our PROD environment”
  • “We don’t have time for testing”
  • “It will take a long time to set up a test environment”


As a Manager, understand how your teams are sized and their workload. For a given Software and how critical it is to your business, do you have enough resources to install best practices in Change Management

As an individual contributor running operations and bearing the responsibility of providing the best experience for your Customers, a lot is riding on your choices! An extra step of validating the change in UAT should only give you the reassurance needed to complete the change in Production. If you don’t see this happening in your Organization, time to raise the RED flag. Feel free to refer back to this post as a means for building justification 👍

2. Weak Leader

Chances are that you are/have a weak leader.


Do you see you or your team try to fix what are clearly People problems through Software features? Do you find the room going silent when you walk into a room filled with your team?

Bad Mood


As a Manager, This is a major problem brewing in your ranks. This may not be very prevalent or apparent but beyond what is tolerable Office Politics, when your team members are not partnering with other teams to achieve an outcome, it is time for a team building exercise! It is also critical that you earn the trust of your team.

As an individual contributor, If you feel mentally drained or always on the defensive when talking to a certain team member, you are probably at fault as well. It is time for an introspection and try to understand how you can improve your side of the equation - maybe you need more research to backup your ask or maybe you need to change your approach with this individual. If nothing works, what can i say.. some people just wake up on the wrong side of the bed…everyday! 😣

3. No Culture

Chances are that your team lacks a culture or simply nothing that ties them together towards accomplishing a single vision and objective!


Do you find that no one on your team is taking initiatives and lacks self motivation? Do you find yourself with/in a team full of contractors?


As a Manager, ensure you are cultivating ownership or fostering thought leadership amidst your team. Rewarding the right actions is often a great way to reinforce positive behavior. Finding and tapping into the the inherent motivation of individuals on your team and turning that into positive momentum is the crucial skill any manager needs to obtain!

As an individual contributor, if you find yourself in this position and if you are a high agency individual, you should be able to single handedly influence a positive energy amidst the team. If you aren’t being recognized or valued for making any headway to improve the team’s culture, that’s your cue to start looking for a better team to work with.

4. Lack of Collaboration

Chances are that you have a divided team in your hands. Teams develop these silos for a number of reasons ranging for ego, politics, lack of clarity etc.


Do you do more of the talking that your team in a team meeting? Do you find it difficult to have your team engaging in a conversation? Do you sometimes have your Vendor trying to broker or negotiate a discussion within your teams?


As a Manager, ensure that

  • you are enabling your teams to stay connected in these primarily remote first culture these days and ensure there are no huge egos within the team
  • you are setting clear goals (strategic and tactical) and socializing that amongst the team so they can work in unison to achieve it
  • that there are clear career progression paths established so you don’t have a few individuals pitting against each other and causing a division amongst the team

As an individual contributor, ensure you are a team player first and initiating conversations that squash confusion. The biggest problem that we have is mostly around Collaboration. Bringing people together is difficult at first, starts making sense with the second attempt and is recognized as the most critical element for success in every subsequent attempts.

5. Lack of Expertise

Chances are that your team is not adequately certified to manage the product for day 2 operations!


Do you often need Professional Services to do anything with a Product? When something bad happens with a Product, do you scramble to make a call to the Vendor first? Do you feel like your organization is behind the curve on IT innovations within your Industry?


As a Manager, encourage your team members to get Certified on the Products that are considered Business critical. If your budget is limited, plan on a rotational program to get your team certified in batches so at least a few members of your team are certified any given year.

As an individual contributor, the industry loves those that are experts and your career growth depends on your proficiency in the area you claim to work on. There are a number of ways to be an expert on Technology domain and keeping yourselves relevant. Some ideas are

  • Subscribing to blogs, Vendor knowledge base and Experts in the domain
  • Hands on Labs or maintaining your own Lab
  • Staying connected with Peers in the Technology domain

BONUS: Lack of Vision

Chances are that you don’t have a vision for your Team. Chances are that you are not causing the change but you are reacting to those changes.


Do you often rely on your Vendor’s road map to get a sense for where you should be focussing on for your Company? Do you find your team are often firefighting more than leading projects that could positively impact Business Outcomes? Do you see yourself copying others? Do you find your team has difficulty in anticipating change and being able to respond as quickly as the business needs? Do you find you or your team always running from one project to another not having the time to focus or strategize?


Stay aware of your technology domain to get a sense for where you and your industry will be in 6 months, 1 year and 5 years. Even as a draft, write down your idea of the direction you need to take. Start talking about your road maps to your Vendor and be open to identifying areas of improvements.

Any team in this time period are bound to have atleast one of the many challenges we’ve attempted to cover. The suggestions provided are the various successful solutions that I’ve come across. I’d love to hear what your experiences have been - as a Customer or as a Vendor. What has helped you move the needle within your team or with a Customer? Finally, If you agree which some of these thoughts then please consider sharing this blog post with your peers!