The Connected Enterprise: Why Leadership, Technology, Process and People Drift Apart
AI is a tool. What actually decides whether technology creates value is leadership, process, people, and the systems you already have. That was the message of The Connected Enterprise, an executive forum Reliable Technology Services (RTS) hosted on October 29, 2026 at Havenspace in Towson, Maryland, in partnership with Epic Solution Partners and Broadheights.
The morning started with a keynote from Microsoft and Hyatt leaders, three partner sessions and a panel. Each speaker tackled a different layer of the same problem, so this post explains that problem and how the layers fit together. Four follow-up posts go deeper into each one.
The drift: leadership, technology, and process have pulled apart
Lenny Giller, President of RTS, opened with a pattern RTS sees across organizations of every size, nonprofit and for-profit alike. Leadership, technology, and the way work gets done have quietly drifted apart. It shows up in four ways.
- Spending without a clear return. RTS often hears this from prospective clients: “I know how much I’m spending. I have no idea what I’m getting in return.”
- Tools nobody owns. Most organizations run a hodgepodge of tools. Nobody knows each tool’s full capabilities or what problem it solves, so teams buy new tools when something they already pay for could do the job.
- Teams moving without direction. Leadership often doesn’t set clear expectations for an internal IT team or a managed service provider. When nobody sets direction, teams make their own calls and pull in different directions.
- Risk nobody sees until it’s too late. Old, unauthorized accounts stay active. When people leave, nobody knows exactly what they worked on. Smart, well-meaning employees build their own tool sets to get work done, and the risk stays invisible until it becomes a problem.
Nobody is doing anything wrong. Nobody is connecting the dots.
Reconnecting the pieces: the four layers of a connected enterprise
A connected enterprise is one where leadership, technology, process and people work together. Here is what each layer means.
Leadership: setting direction before buying technology
Lenny Giller of RTS asked who is steering your technology. In many organizations the answer is nobody. Leaders hire technical people and tell them to “go deal with it,” so IT reports tickets closed and uptime while leadership wants growth, better service, and less risk. The fix doesn’t need more technology. It starts with knowing what you have, why you have it, who owns it and whether it’s secure, and then setting clear outcomes, priorities, and guardrails.
Technology and value: getting more from what you already own
PJ Sawchuk of Epic Solution Partners shared six things people say that signal value is leaking, from “We pay for Microsoft 365, but we still pay for Zoom and Dropbox” to “We don’t talk about that project.” Each one comes with a simple place to start, and all six point back to governance, visibility, standard processes, automation, and having the right people in the room.
Process: fixing the work before adding AI
Michael Bresler of Broadheights closed the sessions with a warning: if you put AI on top of a broken process, you just make the problem worse faster. Start with the outcome you want, find what’s getting in the way, simplify the work, and only then choose the technology. In Broadheights’ experience, about 40% of the solutions it identifies are already existing tools clients pay for.
People: closing the cultural lag
Organizations can buy and roll out technology in weeks, but the habits, roles and trust around it take much longer to catch up. Talisha Padgett of Microsoft and Carlee Wolfe of Hyatt Hotels called this cultural lag, and it explains many of the drift’s symptoms: licenses nobody uses, spending without a return, and teams unsure what they are allowed to do. Their message: people close the lag when they know why the change is happening, what success looks like, where the guardrails are, and that they will get time and support to learn.
How the layers fit together
The speakers came from different angles, but they described the same sequence.
- Leadership sets direction first.
- Next, you get clear on the systems you already have and whether they’re paying off.
- Then you fix the process, and only then do you decide where AI fits.
- People run through every step: none of it sticks unless your team understands it, trusts it, and has time to learn it.
The closing panel, facilitated by Talisha Padgett with Michael Bresler, Lenny Giller and PJ Sawchuk, kept coming back to that idea. Their practical advice on getting started, guardrails, experimentation, AI costs and making change stick is woven into the four follow-up posts.
Questions to take back to your team
The goal of the morning was to leave with better questions. Here are the ones the presenters asked every leader to take back:
- What outcomes do we want technology to deliver?
- What problem is each tool solving, and who owns it?
- Are we working inside our approved systems?
- Have we given our team clear guardrails and permission to move?
- Can each member of our leadership team name the same top three priorities, and does our technology spending clearly support them?
- Where are our people relying on spreadsheets, workarounds, or re-entering data to get their jobs done?
- If a key person left tomorrow, which systems, processes, or knowledge would leave with them?
- Are we fixing the underlying process, or just using technology to make an inefficient process faster?
- How will we measure success beyond efficiency, in capacity created, employee experience, and organizational impact?
The bottom line, leadership sets direction, process comes before tools, and people make or break every technology investment, AI included. When those pieces are connected, technology starts paying off.
Have questions? Contact our speakers.
Keynote speakers
Talisha Padgett
GM, Global Marketing Technology & AI Transformation, Microsoft; Co-Founder, Humxn Loop Consulting
Talisha Padgett leads AI transformation for global marketing technology at Microsoft, where she also leads responsible AI and started an AI center of excellence in 2023. Over 20 years she has helped companies such as Marriott and Under Armour get real value from their technology. She is also co-founder of Humxn Loop Consulting, which focuses on the human side of transformation and change management.
Carlee Wolfe
Associate Vice President, Integrated Talent & Organizational Effectiveness, Hyatt Hotels Corporation
Carlee Wolfe leads how Hyatt develops and supports its people, with a people-first approach to AI. Her team’s work includes performance management, from goal setting to feedback and reviews. She champions Hyatt’s mission to care for people so they can be their best, and its definition of care as empathy plus action.
Panelists
Lenny Giller
President, Reliable Technology Services (RTS)
Lenny Giller leads RTS, a managed IT services provider known for elevating technology conversations from the server room to the boardroom. Lenny emphasizes using technology strategically — not just to keep businesses running, but to help them become more efficient, profitable, and competitive. His approach focuses on aligning IT with organizational vision and using modern tools to drive growth.
Michael Bresler
Founder and Managing Member, Broadheights
Michael Bresler founded Broadheights to make work flow so people can do their best work. The firm aligns people and process first, then applies responsible AI to scale what already works, helping nonprofits, schools, foundations, and businesses free up staff time and redirect it toward greater impact. Michael brings more than two decades of experience in business operations, technology, innovation and client success, including executive roles applying AI to drive innovation and streamline operations.
PJ Sawchuk
Partner, Epic Solution Partners
pj.sawchuk@epicsolutionpartners.com
PJ Sawchuk is a partner with Epic Solution Partners, an IT advisory firm that helps organizations align technology strategy with business strategy and guides them through large transformation projects. His background started in technology, and he has since woven operations, large-scale project management and service delivery into his practice. PJ spent 12 years as Director of IT at a mid-Atlantic regional law firm and three years leading the global service team for a CRM software company, and has been consulting since 2020.