The IT Director’s guide to starting a new job

Ozzy Ornelas

IT Director – Legal Services.

People.

Get to know your IT staff. Connect with them one on one and ask if they could change one thing what would it be. Ask what you can do to make their daily task easier and more efficient. Do this quarterly throughout the year and implement some team building activities.

Get to know the leadership team and get comfortable with the decision-makers. Implement an IT roadmap and share your vision with them. Run every major project by them and get their blessing.

Don’t assume you know best; you don’t know everything.

Get to work!

It doesn’t matter how long you’ve been doing this IT director stuff. You’re new and must prove your worth. Know your worth! You must be confident in the direction you’re taking this company.

As usual, stay in the know of the latest tech and trends, don’t get lazy or comfortable.  Implement cloud wherever possible (in my experience hybrid is best). Keep things light and secure.
If you’ve done this before, bring in your network of support and service providers. Use people you trust that can get the job done.

Take your time and get a bird’s eye view of the infrastructure. Document everything and remember… you must be the senior admin, tech, or engineer.

Schedule a vulnerability scan and address all major issues. Follow that up with a penetration test when you’re ready. Don’t get caught off guard! Review the company’s cybersecurity incident response plan and if they don’t have one implement it!

Be ready; you’re in charge now.

Corey Jeffers 

Director of Technology – Education.

In my career, I’ve been lucky to work for three highly-effective directors of technology before becoming one myself. I attribute many of my own accomplishments in this area to the leadership they displayed for me when I was a classroom teacher, library media specialist, and instructional coach. Despite having great mentors in previous districts, I moved into a new position and experienced some significant anxiety, but also some notable success.

Choose Your District Wisely.

Familiarize yourself with the fiscal longevity of the school district. If there are only two years left of a thinly-passed, non-recurring referendum and three board members have recently been elected who didn’t support the referendum originally, you may want to reconsider if jumping into this setting is wise.

Understand the expectations of your role in relation to the rest of the administrative team and the superintendent’s cabinet. Will you be on the cabinet, so you have a voice in the discussion and planning stages of district initiatives? OR, will you simply need to support the decisions made by the board and administrative team?

Clarify to whom you report in the organizational chart. A wise tech director once told me never to take a position where you report directly to the business manager. Instead, look for a position where you report to the superintendent or an executive director of administration. There are times when the cheapest option is not what’s best, and sometimes the value of investment supersedes return on investment.

Know who mainly directs curriculum, instruction, and assessment initiatives in the district, and do what you can to understand that person’s vision, mission, and perception of the role technology plays in student learning. Find out as much as you can about the team you’ll be managing and what current roles have existed in technology services from the institution’s history. Furthermore, clarify what flexibility exists in adding or rearranging members and/or roles within that team.

“Go Slow to Go Fast”.

I attribute this to a previous administrator who had to quell my desire to change everything immediately. I’ve learned that this is incredibly important because taking the time to plan, articulate, communicate, criticize, evaluate, and review changes and initiatives will seem slow; however, if you put in the time to do these things carefully, initiatives will progress faster and smoother with all stakeholders whom you support.

Being in a position like this for the first time requires obtaining the trust from a large variety of people. This means progress in your first year may feel slow because you’ll need to do a lot of listening, auditing, prioritizing, and then planning. The listening and auditing should never be underestimated because these practices help you to know WHY things might be the way they are in your new position.

Understanding institutional history can help you gain empathy for those in your institution whom you may now supervise or support, and it can help you to capture and act upon the minute cultural details that can derail important change initiatives. Knowing these details and paying them some attention can help you help others to make some uncomfortable changes that might be necessary to create a better learning environment and institute more consistent procedures and practices.

“Phone a Friend – This Time You ARE Alone”.

Many districts have just one director of technology–which means you are alone–kind of. The weight of this becomes very real in the first month because you alone are the end of the line for a number of decisions in your district. Many times it’s very difficult to know how to make the right decisions with very little experience and no one else in an exact peer position with whom you can collaborate. This is why “phoning a friend” is important.

I was lucky to have a few fellow tech directors reach out to me, and I reached out to a few others. I am growing a trusted network of other directors to help me along the way. No one can give you the right answers, but you can learn from their experiences, and simply talking through difficult decisions will help you to remain true to what you believe is right. Much of this position is navigating ambiguity, so wisdom can be priceless. Furthermore, I learned critically important lessons about long-term budgeting and strategic planning from others who have been in this position for a number of years.

Tell Your Story or Someone Else Will.

It’s not always easy to show the impact you and your team have made over time. Documenting the initial “state of the tech” in terms of infrastructure, professional development, staff perceptions, and more are critical in showing how you and your team have brought positive change. Some people do this at state and national conferences; I chose to do this more locally to the board of education, the superintendent, the administrative team, and other cross-functional teams.

Images, video, monitoring data, drafts of procedures and policies, BrightBytes survey data–all of this contributes visibly to the impact you make as a director of technology. Sometimes the changes seem so subtle to stakeholders until you show them how much impact has been made. For example, before we overhauled every network closet and added APs to every classroom district-wide, we took pictures of closets, collected WiFi data, documented number of tickets related to the poor wireless connection, and we compared all of this side by side after the installation was complete.

Furthermore, we instituted BrightBytes and took a survey before the wireless change and before students received 1:1 devices in elementary school. That gave us a clear set of data to show how much it all improved after these changes were made. Now the difference is visible in multiple ways. If you don’t do this, you run the risk of losing out to under-informed anecdotes.

Align Technology Initiatives with Learning Initiatives.

As much as possible, try not to allow technology to be seen as a separate initiative or an isolated discourse in the district. When technology is introduced along with or directly in support of CIA initiatives that are already in or about to be in place, this can help stakeholders realize that technology is merely the tool that makes the initiative more scalable, achievable, or palatable.

Keeping learning outcomes at the forefront of every technology decision is an important filter for deciding which technology to support and when.

Collaborate with Other Administrators.

Making an effort to know your building and district administrators is important. You will clash at times with building administration in an effort to bring out necessary district change, but establishing a professional relationship with each, to whatever degree is possible, is something that will go a long way in helping to be certain initiatives, training, and change is managed effectively.

Attending staff meetings, department meetings, district administrative meetings, board meetings, and more can help you begin establishing and maintaining those relationships.

Lastly, these types of practices help you to be more visible, so stakeholders know there is a real human being behind the screen.

“Never Let a Good Crisis Go to Waste”.

I attribute this to another technology administrator with whom I worked. This is a mindset for longevity. Making change includes taking risks; therefore, you will find yourself at times in situations of very visible “failure.” The question you’ll always have to ask yourself is, “Does this failure define me as a director of technology?” Chances are, if you find a way to learn from the crisis and salvage something positive from that experience, the failure will not define you as a technology director. Instead, the ways in which you let that crisis change something for the better will define you as a leader.

Become a CETL.

Join the Consortium of School Networks (CoSN) and become a Certified Education Technology Leader. The Framework for CTOs will help you validate where your core focus should be, and the framework will help you reflect rigorously. Through becoming CETL certified, you will meet a variety of motivated, passionate technology leaders, and it’s a great way to build your network.

Furthermore, the CETL certification might help validate you in your early stages, and you will learn about the vast array of resources available at CoSN to help you succeed.

Jim Lipski

Operations and Engineering Director – Financial Services.

Moving from mid-level IT management to a Director position requires one to change perspectives, alignment, and strategies.

Managing Managers and Teams.

One of the most important tasks taken on is that of developing staff. Work with your managers and staff to understand their strengths, develop them, and align their teams to bring all the skills needed across the group. Proper delegation of tasks and clear direction on priority are essential.

Business Alignment.

Set up formal and informal meetings to get acquainted with your peers across the business. Formal meetings help to vet the what and when parts of the strategy, informal ones can help to draw out the why. These coffee/lunch type of touch bases are a great way to develop a rapport with your business partners and creates a greater sense of trust. This becomes invaluable as budgets, priorities, and crises occur. Having a trusting relationship is a vital aspect of success.

Strategy.

Develop a long-term roadmap of strategy and connect short-term efforts to align with it. This includes organizational development, skills alignment, and talent management from the people side, technology development that aligns to business needs and tech debt retirement to ensure a balanced approach is taken.

James Matelski

IT Director – Local Government.

Understand the situation.

The biggest challenge for any new IT Director is to continue to embrace the status quo and make minimal changes to existing operational workflows and technologies. A new executive is frequently hesitant on implementing disruptive technology that may have an immediate negative impact on existing business processes and workflows. Quite often, a business is stuck in a rut and continues to do things the way they always have been done. Employees have a tough time seeing where new or innovative technology can directly add competitive advantage and increase productivity. An organizational culture may be fearful of change, and the new executive is often too afraid of making large-scale changes in technologies or strategic direction.

Embrace the transformation.

The executive is often hired to formulate new visions and strategies, to achieve breakthrough transformation of technology platforms and associated personnel. You need to understand the underlying culture and its constraints, but this doesn’t mean you have to be bound by it and let fear of change undermine your efforts. This requires exceptional leadership that focuses on multiple skill sets. Fear and resistance to change shouldn’t dim your vision or significantly alter your beliefs on what the company should become.

Let creativity and initiative be your guiding light. There will always be those that grind their teeth with any element of change. These people will never go away. A transformative leader recognizes the need for change and formulates a convincing business case, all the while attaining new followers that will help propel the vision into reality.