A few years ago I was leading IT for a large organization in the middle of a vendor selection. My team had opinions. The sales reps had plenty to say about their products. What I did not have was a neutral peer. Someone who had been through the same process, with no agenda, who could tell me what they actually experienced on the other side of the contract.
I made the best decision I could with the information I had. But I always wondered what I was missing.
That question stayed with me longer than I expected. Not because the decision turned out badly, but because I recognized something in that moment that I had been feeling for a while without naming it. IT leadership can be a genuinely lonely role. You are often the only person in your organization who fully understands both the technical landscape and the business pressure at the same time. Your team looks to you for direction. Your vendors want to close deals. Your executives want results without complexity.
None of them can give you what a peer can.
I do not mean a peer in the loose sense. Not a LinkedIn connection or someone you see at a conference once a year. I mean someone at the same level, facing the same pressures, who has no stake in what you decide. Someone you can call when something goes sideways at 4pm on a Friday and say what you actually think without it getting back to your CEO.
That kind of relationship is rare. For most IT leaders, it does not exist at all.
I have seen what happens in a room when it does exist. At a recent IT Connections session, one of our members mentioned they had just completed a migration to a new phone system and collaboration platform. They shared what went well, what they would do differently, and what surprised them along the way.
Four other members in that room were actively evaluating the same type of project. The conversation that followed was not on the agenda. It happened because the right people were in the right room at the right time. They compared notes, asked hard questions, and pushed back on each other's assumptions. By the end of the session, those four leaders had scheduled time together to go deeper.
That kind of conversation cannot happen in a webinar. It cannot happen in a vendor demo. It can only happen when trust has been built and everyone in the room is there for the same reason. Not to sell something, not to look smart, but to actually help each other do the job better.
There are a few things a peer community gives IT leaders that are genuinely hard to find anywhere else.
The first is honest, unfiltered perspective. When someone in the group has been through a vendor evaluation, a team restructuring, or a budget conversation that went sideways, their experience is the most useful thing you can access. They have nothing to gain from shading the truth.
The second is a simple but underrated thing: validation. Sometimes you just need to know that what you are dealing with is normal. That other IT leaders are facing the same pressures, making similar tradeoffs, and figuring it out as they go. That feeling of not being alone in the room is more valuable than most people admit out loud.
The third is accelerated learning. The collective experience in a room of ten IT leaders is worth more than any conference or certification. Practical knowledge from people who have actually implemented, failed, and adjusted is irreplaceable. You cannot get it from a vendor whitepaper or a LinkedIn post.
When I launched IT Connections, I was trying to solve the problem I had experienced myself. Not just in hindsight, but for the IT leaders who are navigating those decisions right now without the peer they need and cannot find.
If any of this resonates, that is not a coincidence. It means you have felt it too.
Reflection for this issue:
Think about a decision you made in the last twelve months where you wish you had a neutral peer to call. What would that conversation have looked like, and what was the cost of not having it?
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