Something I have noticed in conversations with IT leaders over the past year is that the hardest part of the job rarely makes it into job descriptions.
It is not the technology. Most IT leaders are good at the technology. It is everything around it. Leading a team of people who look to you for direction. Navigating a budget conversation with a CFO who sees IT as a cost center. Supporting a first time manager who was excellent as an individual contributor and is now struggling to let go of the work they used to do. Figuring out how to hire the right person for a role that did not exist six months ago.
Those are the conversations that keep IT leaders up at night. And for most of them, there is nowhere to have those conversations.
That is why I started writing.
I spent more than twenty years leading IT at organizations across the region, most recently as Senior Director of Information Technology at POET. I have sat in the chair you are sitting in. I have made decisions without enough information, managed through budget cuts with a team that deserved better, and learned things the hard way that I wish someone had told me earlier.
When I launched Simplify IT Consulting and built IT Connections, a peer community for technology leaders across the Upper Midwest, I kept hearing the same thing in different forms. IT leaders who were newer to their role or newer to their company felt like they were figuring things out alone. Not because they were not capable, but because the role itself does not come with a built-in support system.
The Candid Walk is my attempt to be part of that support system.
This newsletter is not a tactics playbook. It is not a list of things you must do to be a great IT leader. It is a conversation from someone who has been in your shoes, written for the reality of what it actually feels like to lead people and technology at the same time. Some issues will challenge how you are thinking about something. Some will simply remind you that what you are dealing with is normal. All of them will be honest.
I will write about hiring and how to find the right people for the right roles. About developing the people already on your team and helping them grow their skills and their voice. About communication inside your team and across the organization. About the first time manager who just got promoted and is not sure yet how to lead the people who used to be their peers.
I will not tell you what to do. I will share what I have seen, what I have learned, and what I think is worth sitting with. You will draw your own conclusions. That is the point.
If you are an IT leader who is earlier in your journey and sometimes wonders whether you belong in the room, this newsletter was written for you. If you are further along and still carry more than you let on, it was written for you too.
I am glad you are here.
Reflection for this issue:
What is one part of your role right now that you wish you could talk through with someone who truly understood it? Hold that thought. That is exactly what we are here for.
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