Over the course of managing enterprise IT initiatives at various scales, I’ve encountered challenging stakeholders, unexpected obstacles, and projects that (at the time) seemed determined to push everyone past their limits. In retrospect, during many of those turbulent times I am in wonder that we still delivered meaningful outcomes. Over the years, I’ve distilled a few lessons that continue to shape my approach on hectic Ops and Infra projects. Before I get into it, here’s the main takeaway early: Projects Are People and are are the key focus ahead of whatever it is your team is delivering.
Listening and Acknowledgment
People are why we’re here (why we are anywhere), and in IT project work this becomes crystal clear the longer you operate in the PM arena. In complex enterprise environments, it’s tempting to rush straight to a solution—after all, we’re there to drive projects forward, implement systems, and realize tangible results. Yet, sometimes, stakeholders simply need to feel heard. That need even competes sometimes against the very deliverables we’re working toward. Stakeholders may already suspect the best path forward, but want to test their thinking against our perspective. Or they may be frustrated by organizational friction and look to us for validation and empathy. Sometimes the best thing any PM can do…is just listen.
Early in my career I managed a project where every status meeting opened with a lengthy airing of grievances. On the surface, it seemed like a waste of valuable time and tested my patience. I was young and impatient, myself. But over the course of that long project, I learned: rather than pushing back, or moving into solution mode, I showed my stakeholders and core team that I was listening. I listened carefully. I acknowledged their concerns. And then I asked questions, and listened even more. I let my teams and stakeholders know that I truly understood the pressure they felt and, without my even realizing it, I was delivering something they needed: affirmation. Even when I moved to address their issues in my PM role, by developing corrective measures, I found that poeple craved direct and overt recognition that I grasped their struggles. This taught me that active listening, and explicit acknowledgment, can be just as important as offering any well-structured solution.
Owning Our Errors
Because Projects are ultimately people and because we’re all humans: mistakes are inevitable. Whether due to shifting project requirements, overlooked details, or misunderstandings between teams, even the most experienced professionals will occasionally stumble. Add in timelines and pressure from project sponsors or the C-Suite, and…things happen. Mistakes get made. What matters is not that a mistake occurred, but how quickly and transparently we address it.
A mentor once impressed upon me that what stakeholders truly care about during pivot events like this: what is the remediation plan—what we will do, and by when, to get back on track. In IT project management this often means aligning corrections with critical timelines, possibly working nights or weekends, to ensure that no cascading impacts derail other milestones. Hiding the truth or sugarcoating the situation never helps. When trust is at stake, forthright communication and a clear plan to correct the course are invaluable. Repeated errors signal systemic issues, of course, but that’s a separate conversation. People want to do good, and I have found people on teams want each other to succeed past mistakes when they happen. And they will happen! So the bottom line here is: we own any misstep together, we fix it promptly, and we move forward together as a team.
Ensuring Alignment
“Alignment” is such a dry buzz-term these days, but really means something: people on projects need to regularly align (and re-align) with why they are there on the team, and doing what they’re doing. So among the most crucial lessons I’ve learned through the years, alignment is definitely way, way up there. Contracts and statements of work spell out formal responsibilities, but not everyone reads them thoroughly or interprets them the same way. I’ve found that periodically aligning (and re-aligning) all parties—internal teams, vendors, and executive sponsors—on the project’s Scope and objectives prevents a host of downstream issues.
It’s not enough to assume everyone recalls the original vision or the intended deliverables. Take a few moments in each major phase to restate the project’s purpose and requirements in plain language. This can be as simple as giving a two or three-minute talk at the start of a meeting. Check that every participant shares the same understanding, and reference the scope or any contracts when necessary to ground the conversation. This may not be a one-time effort. As the project evolves, context grows richer and perspectives change, requiring a renewed focus on alignment.
On one initiative, we had reports of mounting “roadblocks” halting progress. Reviewing those issues, it became clear we were suffering from misalignment rather than any inherent technical barrier. We gathered everyone—developers, business owners, security leads, and support staff—and confirmed where we stood, what we aimed to deliver, and how. Within half an hour, perceived obstacles faded away, and the team regained momentum. Had we focused solely on the symptoms, we would have missed the underlying cause and continued to falter. People need alignment, and projects are always at-risk of their humans getting overwhelmed or a bit lost in all the work.
Projects Truly Are People…
Projects only ever exist because of people, and they succeed or fail because of people, and so it stands to reason that as PM your highest work (and largest role) is showing-up to listen and work with people every single day. Enterprise IT projects demand more than technical savvy. They require the ability to acknowledge stakeholders’ feelings, transparently resolve errors, and foster ongoing alignment among a diverse group of human contributors. By making a conscious effort to listen actively, own any missteps, and regularly reaffirm the project’s guiding principles and plan: we create an environment where issues can be resolved more smoothly and outcomes are more reliably achieved.