Tony Messina – How to become a IT leader from Mid level manager and overcome shortcomings



Could you tell me how you got started in your IT career and ended up in your current role?

My path to IT was somewhat accidental. I grew up in a construction family and worked in the business through high school and college. I expected to do this for a career. There is a certain satisfaction that comes from doing something tangible that lasts a long time. It’s been over 40 years since I last worked in the field. It is still gratifying to see buildings I worked on as a teenager still in use today.

I was never overly interested in technology. I was skeptical when a friend asked me to interview for a job in the Management Science Department at Campbell Soup. I graduated from college in 1980 amid a poor job market, flooded with baby boomers. I needed a job. Back then most IT departments were back-room programming shops. Systems were homegrown and primarily used to automate base transactions. What interested me was how the company was using information technology to support business decisions. There were linear programming models used to optimize which plants would manufacture and ship product. Statistical analysis tools were used to analyze shopping trends. One of the things I worked on was a financial model that projected profit as products made at the plants with differing manufacturing costs moved through the distribution system. The idea that technology was a means to an end not the end unto itself has been one of my guiding principles.

Over the years I bounced back and forth between IT and other functional roles gaining a broad array of experience. After a few years in my initial IT role, I transferred to Finance as an analyst. I returned to IT as a business unit IT lead and project director. After leading a successful Y2K project, I ran our Technical Services function and then led the Corporate Systems group. From there I transferred to HR supporting IT. I returned to IT, in a role best described as the Chief of Staff where I ran all the administrative and governance functions including security, finance, communications, vendor management, and program management. In 2015, I left the company for a role as an adjunct professor and consultant. As a consultant, I work primarily with emerging leaders and departments in transition to help them build out leadership and administrative capabilities leveraging the skills and experiences mentioned above.

What is your advice to Mid-level Managers who are aspiring to transition to senior roles in IT and what skills are critical to getting to that level?

Advancing from mid-level to executive leadership is a quantum leap. Many get stuck here, Generally, mid-level IT leaders have the technical skills but need to broaden the others and develop an executive mindset.  

To be a successful IT leader you need a broad set of skills. In addition to making technology decisions, you need to run the function. You must be able to manage vendors, manage budgets, develop people, and communicate up and down the organization. In a mid-level role, you may do some of these things, but it is unlikely you do all of them. You don’t have to do all these yourself but must be able to assess the quality of work delegated to others.

Executive mindset is critical. Up to this point, you are being good at what you do has been your path to advancement. You likely have someone above you serving as a buffer at the next level covering for any gaps in your portfolio. As an executive, you need to think more broadly than your group or the IT function. It’s about the company and the role you play in advancing the company’s goals. You must become a business leader in addition to your IT skills.

In most companies, sales/marketing, logistics, and in some cases product development drive the business. All other functions like HR, Legal, Finance and IT exist to support the core to achieve company goals. Fundamentally, IT is responsible for providing base services like transaction systems and office automation. It also provides information for decision-making and enabling technology. Sometimes mid-level managers get stuck in perfecting their craft or thinking their role is more important than it really is. You have to be pragmatic, not dogmatic in your approach. You don’t want to be in a situation where doing your job becomes an obstacle preventing others from doing theirs.

While you can augment your capabilities in many ways, the most important is the ability to understand what is important to senior leadership and to communicate it in terms that they understand. For example, there was a time when our company was trying to understand how IT money was spent. We had all the data and analysis. Our presentation to the executives was in the form of lists and tables. Our execs were used to seeing financial information presented as bridge charts. Once we realized that and reformatted our presentations, we were better able to get our message across.

How do you prepare for presentations or meetings with the leadership or board?

Presentations are is a big part of the job. I take it very seriously. An obvious first step is to make sure the facts and analysis are correct. Then I story board the presentation to make sure the message flows from beginning to end. Each slide should have a clear message that tells the audience what to takeaway. When possible I have others look at it for content and clarity. I rehearse several times to make sure it flows in delivery. Sometimes I even practice in front of a camera to ensure my comfort with delivery and body language. I developed my style by watching what effective communicators do and incorporated their best practices. I also find it important to adjust my format and delivery to the audience. Executive presentations for example are much different than let’s say departmental town halls. Companies also have certain ways they like to see and hear information. It has to be delivered in a format they are familiar. Finally, taking advantage of public speaking opportunities as a guest speaker or teaching a classes was helpful in honing my presentation skills.

What are the skills important for IT leaders to build for the senior leadership functions?

When assessing talent for advancement, I look for business acumen. It is important to know how your company makes money and its strategic priorities. That tells how IT can best serve the company. Financial acumen is also important. IT is usually one of the biggest administrative expenses in the company. You need to know where the budget is spent and what decisions drive spending. Also very important is the ability to communicate at the executive level. It doesn’t matter how good you are if you can’t get your message across. Finally is overall leadership potential and emotional maturity. All of these can be developed.

 What was one of the things you found surprising as you advanced to department leadership? 

In addition to stepping up in terms of performance and mindset, I wasn’t prepared for the changes resulting from the new reporting relationship. Up to this point, I had the cover of reporting to someone who was also accountable for my performance and provided guidance when needed. Suddenly, I was on my own and had to find support elsewhere. For me, it came from peer leaders outside the function and the various consultants we were using. I also had a similar experience with my former peers. Suddenly I was being treated differently. That really hit home for me one time when my wife and I were at a business social gathering. Afterward, she informed me that even though those around me laughed, my attempts at humor were not funny. Nothing like family to keep you humble.

If you want to advise young women to start an IT career, What would be the 2 or 3 things you would advise them to follow now to get a job quickly?

Frankly, it is disappointing we even need to address this question today, but I know disparity still exists, Overall, I would tell them what I tell everyone.

  • Learn your craft. The business world changes rapidly so never stop learning.
  • Build your network.
  • Stay connected. 

If you ever need to leave the workforce for any period of time, stay current with your field through trade organizations, and your network, and if possible, take small assignments even if they are volunteer. I left IT for a dedicated role in HR for around 18 months. I didn’t follow my own advice. When I returned, I was so out of the loop, that it took over a year to reestablish myself. 

I also recommend going to a school that incorporates internships into its program. There is nothing more valuable than graduating with real experience and having already made professional contacts. Finally, if you find the company doesn’t value diversity, go somewhere else. Demand for talent for the foreseeable future will continue to be great and there are many opportunities for growth. With the ability for remote work, geography is less of a challenge. There is no reason to stay somewhere that does not value you.

The biggest learning comes from learning from mistakes. If you look at your career, what would be 1 or 2 mistakes which you think you faced, how you overcame them, and is there any hindsight on you wishing you could have handled them differently?

Moving between IT and business functions multiple times was a great way to learn the business from all angles. It also proved to be a detriment. I left IT as a developer and returned seven years later as manager. In the process I missed several critical IT experiences. I was assigned to run a complex multi-million dollar warehouse automation project without having large-scale project experience. I was overconfident. Having a series of successes, I thought I could run this program without the burden of a formal project methodology. In hindsight, it was death by a thousand cuts. Project sponsorship and ownership were unclear. The project was being run by me at corporate using plant resources who were not all qualified for their roles. Our plants were used to competing with each other and not comfortable collaborating. As such, there was conflict over design among them. The software we purchased was inadequate and we were essentially rewriting it. At one point in the project, our CIO asked me if we should kill the project. I was so confident in my ability to make this work, I said no. About 18 months in our CIO left. New leadership was in and I was out.

There are a lot of lessons coming from this experience. Most obvious is the need for formal project and change management on a complex project. While you might be able to overcome some of these, collectively they were a recipe for failure. The bigger lesson was leadership maturity. I should have seen this project was doomed and had the courage to kill it. Instead, I saw it as an admission of failure and thought through my relationship abilities I could deliver a successful end.

Going forward, I lost my fear of killing projects when there wasn’t a reasonable chance of success. Fortunately, I had a strong internal network. It took a while, but I eventually landed on my feet.

Fantastic point, this is a gap with IT leaders touching their egos. If you have to run this scenario again, any advice on what are the top 3 factors on when you would decide on a project to be shelved than continue?

We know that there is no such thing as an IT project. If you don’t have clear business sponsorship and business ownership, you can’t be successful. Second is the lack of a change management plan. The bigger the project the more important the need for a good plan. Projects are efforts to make a change. Start with a change readiness and risk assessment. Be sure to assess all the individual people impacted by the change. Identify who is supportive and who may present an obstacle. If the project veers away from the plan, take corrective action or halt the project. Third, there are no heroes. Don’t overestimate your capabilities. You need the right skills and players on the team. The price for continuing a poor project both in dollars and career is greater than the price of killing it.

Building a peer network is important. Any advice on organizations to join, networks to improve that can help to build those skills?

For IT leaders, I recommend SIM as a great place. Targeted groups such as Gartner are another place where you can meet others with similar interests. If your company uses them, I also like to take advantage of the large consulting firms and suppliers. Their people have broad exposure to varying companies and can serve as a conduit for building industry relations and learning best practices.  

Are there any resources, training, books, or websites you would recommend to mid-level IT leaders to read or attend which would help them to build their careers?

These are my go-to books for all leaders. 

The Seven Habits of Highly Effective People by Stephen Covey. I don’t really need to elaborate.

The One Minute Manager by Ken Blanchard and Spencer Johnson. The title is misleading. It takes more than a minute to master the simple techniques outlined in the book.

True North and/or Authentic Leadership by Bill George. It is important to know your inner self to be successful.

The BLUEPRINT by Doug Conant. Doug uses his own personal leadership journey to provide a guideline for successful leaders.

What Got You Here, Won’t Get You There by Marshall Goldsmith. In this book, Goldsmith points out several behavioral traits that must be overcome to continue career advancement.

A couple of lesser-knowns

Decisive by Chip and Dan Heath. After reading this book you will look at decision-making in a completely different way.

Death by Meeting by Patrick Lencioni. Using a storytelling approach, Lencioni gives practical advice on how to structure various types of meetings to get the most out of them.

The Goal by Eliyahu M. Goldratt. This book was written in the 1980s but is still relevant. Again, applying a storytelling approach to ongoing process improvement. One of the things I like best about it is how he shows that siloed thinking can optimize one component of the process while sub-optimizing the entire process.


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Tony Messina

Author: Tony Messina

Tony has over 40 years of business experience, including 35 years at a Fortune 500 company. He is currently an independent consultant, specializing in IT Organizational Enablement which includes organization and staff assessment, organization design, staffing, team building, coaching, administration, strategic and operational planning, financial management, change management, governance, and program management. His business experience includes stints in HR and Finance as well as Division and Corporate IT. He has also taught as an adjunct MIS professor at Temple University’s Fox School of Business.

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