Justin Sherwood spent a decade as Deputy CIO/Assistant Director before stepping into his first role as top technology leader at Franklin County, NC. He arrived knowing how decisions are made but less prepared for where the weight lands when they are yours. Six months in, he is building on an inherited foundation while deliberately meeting his team, his departments, and his organization where they are.
Cesile Johnson arrived at Core Bank with a clear view: the internal structure has to work before the technology can. She spent her first months rewriting job descriptions, rebuilding team alignment, and deploying a cross-functional pod model she had refined across thirty years of IT leadership. The result was a model that earned credibility through incremental wins before it earned broad adoption.
Joe Fousek spent 33 years in legal IT before taking a year on the vendor side at Aiden Technologies. That round-trip gave him a direct read on what separates trusted technology partnerships from transactional ones. The same lens shapes how he works with attorneys and develops his team at McDougall Gauley LLP.
Parag Pujari came into Jurgensen Companies as their first CIO with a board mandate to transform an IT department that had no strategy and no seat at the table. Four years later, he names a specific failure mode that most leaders don't address directly: technical ego, the dismissiveness IT professionals show toward people who aren't technically fluent. When that attitude goes unchecked, it kills adoption before transformation has a chance.
Conor Healy built IAB's IT function from the ground up after inheriting a failed Salesforce implementation and a leadership team that had already been burned. He explains how he used a 30/60/90 framework to earn trust without rubbing anyone's face in what had gone wrong, and why getting leadership to feel like co-owners of a solution is the actual work of building credibility in a role with no track record.
Brad Enneking, CIO of Mutual Bancorp, describes how compounding system conversions, locked-in vendor contracts, and tribal resistance make M&A integration far harder than the technology itself. His approach to building a shared identity across acquired teams offers a grounded alternative to the standard absorption playbook.
Nicole Coughlin has served as CIO of the Town of Cary, NC for over a decade, more than twice the typical CIO tenure. She explains how the breadth of centralized municipal IT keeps the role from stagnating, why handing out AI tools is not the same as having an AI strategy, and what it actually takes to get executive buy-in in a government environment.
Brad Gorka, CISO at Veritiv, describes how nearly 30 years in information security have reinforced one principle: assess the people first, then build the program. Running lean teams across organizations of every size, he explains why the essence of security strategy is deciding what you won't do, and why the CISOs who set honest scope build teams that actually deliver.
José Manuel Rodríguez Jiménez, CIO at Metro in Portland, Oregon, explains why AI efficiency claims fall flat without a plan for the reclaimed hours. Drawing on 25 years of IT leadership across two continents, he describes how building relationships at every level of the organization, starting with frustrations rather than requirements, creates the foundation for shared ownership of technology decisions.
Chuck Scharnagle, CIO at Revere Copper Products, describes how he rebuilt credibility at the oldest continuous manufacturer in the United States by delivering incrementally, speaking in business outcomes, and treating IT as a customer service organization. His approach turned a department that executives openly resented into one they no longer question.
Rusty Kennington, a four-time PE-backed CIO now leading Denali Water Solutions, explains how he builds credibility by speaking in outcomes, proving results in months, and preparing for exit from day one. His frameworks for AI investment and team development offer a grounded playbook for CIOs entering private equity.
How do you know that you are aligned with the business? There is a difference between something feeling off and true misalignment.
People can downplay titles, but you can’t overplay their power.
Anger is not misplaced in the workforce. But it is often mismanaged. Master it so that it doesn’t master you.
Four practices will bridge the generational gap you face.
Getting buy-in isn’t so much about the work you do but the way in which you do it.
Succession planning specifically, and leadership development overall, is generally lacking in companies and IT because they don’t understand the value of a leadership farm system.
You meet challenges and opportunities. The doorway in is for another to help you out.
It’s not the tyranny of the urgent that has you down; and only one practice will build you up.
Why you aren’t seeing what you need to be seeing is different from not seeing
Acquisition, engagement and retention starts with a different emphasis in hiring, onboarding and training.
You can only accomplish so much. The answer isn’t saying no.
Winning without listening is losing that’s running behind but soon catching up.
Eventually, what either trips you up or builds you up has to do with three leadership constants.
The person who can answer “then what” is more valuable than the leader who answers “now what.”
2024 was hard fought. I saw some things in tech leadership no other leader should overlook.
We don’t just change perception. We change persuasion.
Lack of cohesion in the company is the reason many CIOs lack a solid tech strategy. You don’t have to change the world overnight, but you can change your environment right away.
The leaders you admire and seek to be like practice one consistent trait and do it better than most.
You have a noise problem. So does your CEO. When information is unreliable, your relationship needs to be more reliable.
CEOs and their business and tech leaders don’t always work together smoothly. Unless corrected, losing streaks develop. Effective CEOs recognize the need to realign or suffer even greater consequences.
You lead a locker room. You can lose the locker room. Winning it back can seem overwhelming, but three essential responses can get it back for you.
Getting the authority to make decisions has never been about your position. It has been about your precision. Clarity, leverage, and peace shine the light into dark alleys.
Generational differences are not new. Resolving them must be.
Too many leaders focus on the process of change and not on the people enacting the change. If the soil is sick, the leader won’t stick.
CIOs who seek significant investments are outcome based. They understand the difference that will be made is the desire that the business seeks.
What worked in the past doesn’t always work well for you now. It’s not always the sacred cow that needs to be toppled; sometimes it’s your favorite pet.
What if growth under your leadership came naturally? How would you lead differently if what matters most happened all by itself?
Entropy sets in over time. Our system of work degrades. The effective CIO sees what is happening and resets, reinvigorates and renews how their team functions. They focus on priority over priorities.
Generative AI can never replace your voice. Attempting to have it do so will betray you and feel like betrayal to others.
Transitioning into a new company is a thrill. Five priority first-actions will cause you to thrive.
CIOs, perhaps more than any other title, are all over the map in who they report to. Take control of what you need to get done by making key three shifts in your mindset and relationship.
Building takes time. It also takes buy-in. And buy-in requires knowing the crucial, not just the superficial.
Your professional growth runs into resistance. Steal best practices from other professions to make your case.
Your CEO can be as pro-AI as any, but if they don’t take this one thing into account, AI will become a monstrous force against the company.
With all that the future of work entails, we have overlooked a treasured quality to value in employees. It’s not how long they stay; it’s who they bring with them.
Life has transitions. You have had them. You may be in one. We often waste them. Here is how you take advantage of those rare moments (gifts) when you are between leaving and starting.
Blended workforces are the new reality. Getting ahead of the wave requires meeting unique challenges with new priorities.
Workforce issues continue to trouble IT progress. A new way of thinking about your team opens new horizons to how you work and who you work with.
Big deals like attraction, retention and engagement, as well as succession, success and sustainability, all hinge on two letters: D and O. What we must undo and really do.
Two keys will communicate your competence and reinforce your credibility. But it all starts with one major difference maker.
We understand change leadership. We don’t talk as much about turnaround leadership. There is a difference, and it shows in whether you stay and leverage or leave and start again.
Coaching is a proven difference maker. Yet, CIOs are behind in having this key to professional advancement and IT effectiveness. Not all coaches are created equal - and CIOs need those who stand above the rest.
Fractional CIOs may be all you need. But getting the most out of the relationship is another matter. These four dynamics will help you hire the right fit and maximize the benefit.
The difference between CIOs and CTOs is more than internal or external facing. It’s about the direction from which you approach the work, and the mindset and behaviors people adopt toward you.
CIOs are leaders, but not all are high-performers. The difference isn’t what they do themselves but what they do for themselves.
Generative AI is only exceptional if used exceptionally. Our normal approach to problem solving won’t move AI past average. For better results, keep AI weird.
Hard markets and tight budgets don’t need to delay the spending you need now. Buy-in isn’t about the budget. It’s about the right decision. And that’s something you can lead.
The CIO search isn’t just about the resume or cultural fit. There are types of CIOs not typical CIOs. Knowing the difference, and who you should look for, is the difference between a CIO who will be effective and long term or a short term placeholder.
Urgent requests and unreasonable timelines are normal. Accepting those requests does not need to be the norm. Five responses will help protect your team to stay focused and your technology vision to be fulfilled.
CEOs want their CIOs to be of greater influence, especially where they don’t have decision making authority.. That means the CIOs need to invest and leverage three critical assets their CEOs have been utilizing for years.
Leadership is more than knowing and showing the way. It’s sharing in the way.
AI will bring revolutionary change. But not until we exercise our power as leaders to affect a greater change.
It’s not enough to tell CEOs what to think. They best manage their expectations of IT through processing three critical areas.
You will run into CEOs who do not have right expectations. They will run over you if you don’t know how to manage their expectations. How do you lead CEOs who have unrealistic expectations of IT while remaining an integral team player?
You can’t do it all, at least not in the timeframe others want you to do it in. There is a better answer than citing backlog - one that educates as well as protects you and your team.
Resistance to rollouts are common, and failure to overcome them is an agony of defeat in a class all by itself. The art of overcoming is anchored in three essentials often unknown or overlooked by CIOs and technology leaders.
Lists of priorities are merely voices competing for attention. Your CEO won't invest unless you show the real need behind four critical areas in 2024 that need buy-in.
It's not enough to form new habits to accomplish great plans.
When peak performers compete, it's not the skill in question but the equipment at play.
You led well in a year of the unforeseen. 2024 calls for one area of growth that must be your most intentional.
There are certain things in business that don’t get close attention until something triggers action. For CEOs, IT can be that place where familiarity has become enough. There are ten triggers that will move a CEO to take a closer look, and ten turning points CEOs can lead out in before triggers are ever needed.
There is one trait that is consistent with leaders who fall behind. It’s not about their knowledge, skill or work ethic. It’s about who is or isn’t with them.
What your team needs most is the best of you seeing and saying the best of them.
We can find ourselves hostage to a person in IT who alone holds access to key programs and data. How do you prevent such a vulnerability, and what do you do if it’s too late? Here are three practical plans to work through.
CIOs benefit from periodic resets. Approaching the end of a calendar year is a great time to reset for a new beginning in the new year. Reset to three essential needs.
Good AI policies are easy to get your hands on and modify. Good adoption of those policies is a different matter. It's not in the policy, it's in the presentation.
Transformation is a deep word being lost in translation. So what does it really mean to transform IT? It must be comprehensive, including eight key areas of development.
We know the CIO role is changing. Do you have to wait and see what those changes are? Or is there a better way to transform yourself? Move over Darwin, we have some designing to do.
Do CIOs drive growth? No and yes. And where it is a yes, they focus on six critical areas.
CIOs and their teams suffer from fatigue and fight against natural drags of complacency. One overlooked dynamic is key to restoring the fire and the push you need.
CFOs are in a tough, yet strategic position. Working with them is work; and it should be. How to work with them so that they are a Go rather than a No is a three-stop journey that you lead.
There are two reasons you are not invited to significant meetings and it isn't because you don't know what you are talking about.
I’ve been seeing a lot of mergers taking place, and with it, inheritance of another leader’s team. The work that follows between yours and theirs isn’t always smooth and often is troublesome. Unless you pay attention to one key factor effective CIOs agree has been their key.
We rely too often on our own credibility or research or vendor propaganda to sell our proposals. We rely too little on the best way we know that what we know is right.
We all work with people who are risk-averse. Reframing their perspective, and doing three things that support your cause will help move them to the right decision.
You may have arrived, but fail to keep investing in yourself, and you will be left behind.
Large Language Models are just that - large. Like much of our work with others, LLMs require a bit of mentoring and coaching. To draw out the best it has to give, we have to train it to think like the rest of our team thinks.
There are a lot of good reasons to hang on and press-in to your current situation. And there are three good reasons to take off.
You must lead the way for technology and business to communicate for a change. And for the change to mean anything, you are going to have to change the environment in which all this talking is taking place.
Intelligence Firms like Gartner have their place, but they alone may not best serve your purpose or be the first place to look. What must have first place in your leadership is a community of peers who get behind your purpose and bring practical answers to your pressing needs.
Steering committees fail on a regular basis. The one’s I have been on have been boring at best. A group of CIOs got together and revealed why theirs succeeded. The hard work is in the focus.
It’s not what you don’t know or overlook that bites you as a leader. It’s what is right in front of you that you choose to ignore. Two changes will change everything
Billions of dollars are being invested in generative AI. People see its power. They also feel the responsibility that comes with it. CIOs know that they can’t hold it back and they can’t rush it forward. Mostly, they can’t have their company ignore it. Let the investments others are making be a credible witness to your argumentation.
Change efforts fail because the hard work is done in the wrong place, and because we avoid resistance as much as possible. To succeed at change, create and embrace friction as early as possible.
Effective technology leaders are driven by a certain obsession. Fail to be consumed by it, and the work you put out will be a box to check but hardly art you can’t wait to display.
The question of fairness in remote work continues to be raised. It’s a distraction from the real need and the right question. Ask this, and you change the nature of the discussion once and for all.