Do Right. Be Effective.

Efficiency without effectiveness is wasted effort — and this series is about changing that mindset. I’ll be publishing a new post every week with real-world examples and lessons to share. Subscribe or check back weekly for the next installment of Do Right. Be Effective.

AI in Project Management — Exciting, Powerful… and Worth a Little Caution

Do Right. Be Effective.

Having spent my career as a project manager across healthcare, mortgage banking, and financial services — always focused on technology — people are often surprised when I tell them I’m not an early adopter.

I love technology. I follow innovation closely.
But I also understand how software is built, tested, and deployed — and how many points of failure exist along the way. Because of that, I tend to fall into the early majority category: I adopt when I see evidence that a tool solves real problems without creating new ones.

For me, successful adoption requires intentional testing and validation — not blind trust.

AI Raises the Stakes — and the Opportunities

With the acceleration of AI, avoidance isn’t an option. What is an option is how we approach it.
We owe it to our organizations — and ourselves — to adopt AI with equal parts curiosity and caution.

After returning from the PMI Global Summit, I had the chance to explore how different tools are experimenting with AI to improve the lives of project and portfolio managers. What surprised me most was how varied the use cases were. No two vendors were focused on the same problem.

A few that caught my attention:

• Intelligent resource selection
Tools using historical work patterns to predict which available resource is most likely to successfully complete a task.

• Portfolio-level “what-if” scenario modeling
AI that can evaluate different combinations and timing of projects to determine which path delivers the strongest strategic outcome.

These use cases are exciting — but they’re only the beginning.

Where Do You Want AI to Help?

I want to hear from those who live in the project and portfolio world every day.

What would make your work easier, more accurate, or more strategic?

I’ve created a short, 4-question survey:
👉 https://forms.gle/HmffYiy7jHxs719NA

Your insights will help shape where I focus next — and I’ll share the aggregated results in a future blog post.

I look forward to learning from you.

Why Adopt Modern Strategic Tools?
Do Right. Be Effective.

Do you ever wonder whether your industry is behind the times?
I do — often.

After more than 20 years as a thought leader and project management professional, across four different industries, I’ve watched modern strategic execution tools evolve dramatically. I’ve been part of their development. I’ve watched them scale. And yet… many industries still haven’t adopted them.

Some teams continue to build and track product roadmaps manually or use very rudimentary systems that require huge amounts of duplicate data entry. Some still manage project portfolios through spreadsheets and status emails. And unfortunately, my own industry — Financial Services (specifically Wealth Management) — appears to be among the slowest adopters of modern strategic tools.

What I Saw at PMI Global Summit

Returning from the PMI Global Summit this week, I was impressed — and honestly reinvigorated — by the innovation happening in strategic execution platforms.

The growth of these tools is extraordinary:

• AI embedded in planning, risk monitoring, and forecasting

• Real-time visibility into strategic initiative progress and ROI achievement

• Dashboards that give senior leaders answers instantly

• Seamless alignment between strategy, roadmaps, and work execution

And here’s the kicker…

Jira and DevOps weren’t there.
Because they aren’t strategic execution tools.
They’re work management tools — valuable, but not built to show the health of organizational strategy.

Meanwhile, the industries embracing these modern capabilities and well represented at the conference were:

• Government

• Department of Defense

• Manufacturing

• Construction

• Product-based industries like Procter & Gamble

• And a handful from banking

But major players in Financial Services? Virtually absent.

Why Is Financial Services Missing?

It raises uncomfortable questions:

• Do firms not know what exists outside their bubble?

• Do they assume spreadsheets and manual reporting are “good enough”?

• Are they too overwhelmed by FinTech noise to invest in strategic discipline?

• Or is the industry simply too shortsighted to prioritize efficiency?

With Broker-Dealers and RIAs drowning in vendor choices, this lack of strategic tooling is even more concerning. Every dollar spent on long-term strategy should be a dollar that moves the firm forward — not a dollar wasted on avoidable delays, rework, misalignment, and data entry tasks.

Yet many product and project teams are still:

• Manually tracking progress

• Preparing status decks

• Merging data from multiple systems

• Explaining delays that could be predicted automatically

All while modern tools could free them to focus on the work that actually drives outcomes.

A Reality Check

If your strategic tools don’t give you:

• real-time status

• resource visibility

• risk forecasting

• roadmap alignment

• what-if capabilities

• ROI tracking

…you’re not managing strategy.
You’re managing chaos — manually.

And if your vendors can’t provide this level of transparency and integration?

They may not be worth your time.

Final Thought

Financial Services is too competitive, too fast-moving, and too resource-constrained to continue operating with outdated strategic tools.

If you’d like an evaluation of the tools you’re using — or the ones you should be — reach out and schedule time https://calendar.app.google/xdLqfneFB1FEs6gZ9

Your strategy deserves better than a spreadsheet.

A vision and an ROI that are clear… so what could go wrong?

Do Right. Be Effective.

After three decades of helping companies implement technology, I’ve seen both transformative successes and painful failures. One question I’m often asked is:

“What actually causes technology initiatives to fail?”

Most people assume failure happens because the vision wasn’t clear or the ROI wasn’t defined. Yes — that can derail a project. But far too often, even when the vision is clear and the ROI is compelling, time and misaligned incentives become your enemy.

When Everything Looks Right… But Still Goes Wrong

Let’s assume best-case scenario:

• The customer sees the value and knows what efficiencies the technology should create.

• The vendor has the capability to deliver it — whether today or through a roadmap aligned to the customer's timeline.

Both sides agree on the vision. Both believe in the ROI.
However, even with the right technology and the right plan, incentives often aren’t aligned across the people who need to act, focus, and adopt.

This misalignment shows up in three places:

• Incentives to act — Do people have time? Priority? Accountability?

• Incentives to focus on the target — Are stakeholders motivated to hit deadlines?

• Incentives to adopt — Are end users rewarded for embracing change, or is it easier to keep doing things the old way?

When these incentives aren’t aligned, you face an uphill battle — delays, frustration, and unrealized ROI.

To Break the Cycle……

Before you begin, ask a few key questions  — and build the answers into the project agreement where possible:

• Are the customer’s internal resources truly given the time and authority to provide guidance during implementation?

• Has the expected ROI been clearly communicated to all project participants? Do they understand what’s at risk if the target date slips?

• Are impacted teams expected — and measured — on adoption? Is proficiency tracked as part of performance expectations?

If the answer to any of these is “no,” misalignment is poised to undermine your success.

✅ Let’s Make This Real

Imagine the ROI target is a 3-day reduction in average accounts receivable through technology that streamlines invoice-to-cash operations.

Achieving this would save $500,000 per year, enabling the company to reinvest in new hires and expand product offerings.

Now reconsider the incentive questions:

• Do delays in gathering requirements push the go-live past the fiscal window?

• Do missed development deadlines erode trust between customer and vendor?

• Does poor user adoption prevent the 3-day reduction — even when the technology works exactly as designed?

Great vision. Great ROI. Great plan.

But without aligned incentives, the benefits evaporate.

Collaboration Over Competition: Reflections from The Wealth Mosaic Conference

Do Right. Be Effective.

On October 8–9, I had the privilege of attending the first U.S. Wealth Mosaic Conference in Atlantic City, NJ. (thewealthmosaic.com)

As I left the conference, two thoughts stayed with me:
1️⃣ There are so many creative and impactful fintechs in the wealth management space today that it’s challenging for firms to identify the right tools for their needs.
2️⃣ Even when firms assemble the perfect tech stack, friction often arises when trying to make that vision a reality.

These reflections aren’t new—across my years in healthcare, mortgage banking, and financial services, I’ve seen the same patterns repeat. Bringing a technology vision to life requires reducing several key friction points:

• Conflicting product roadmaps

• Perceived competition among vendors

• Short-term versus long-term priorities

• Limited configurability for end users

So, who’s really driving the vision—the fintechs or the firms?
The truth is, neither can do it alone. The industry as a whole must shape that vision. No single technology stands on its own, and building everything in-house rarely scales. The real opportunity lies in weaving together an ecosystem of expert solutions, allowing each to thrive in its area of strength.

Fintechs, when faced with the future, have two choices:

• Compete and try to build it all themselves, or

• Collaborate and leverage each other’s expertise.

History shows that those who collaborate win. Firms succeed when fintechs “play well in the sandbox”—aligning with industry trends, staying true to their core strengths, and integrating seamlessly.

Ultimately, it’s the firms and the industry that decide which fintechs endure. We’ve spent years focusing on client experience within individual products; now it’s time to focus on the client’s experience across the entire ecosystem.

Things will evolve and settle, but the real winners will be those who choose to work—and win—together.

Including Innovation in Your Portfolio – No Longer Optional

Do Right. Be Effective.

Welcome to the final post in my 4-part series on managing technology portfolios.

·       In Part 2, we explored the cost of over-investing in support and maintenance.

·       In Part 3, we examined the importance of having (and sharing) a roadmap, even as it changes.

·       Now, in Part 4, let’s focus on the role of innovation—why it matters, how to include it, and how much time to devote to it.

Innovation Isn’t Optional Anymore

Technology evolves by the hour. We fear it, test it, adopt parts of it, and eventually adapt to it. Innovation isn’t a one-time big bang—it’s a continuous cycle.

In just 75 years, we’ve gone from the first computer to AI shaping nearly every industry. Standing still isn’t an option. Ignoring change almost guarantees being left behind.

Adding Innovation to the Roadmap

In developing and managing your roadmap, you should include not only planned initiatives but also a separate innovation category—think of it as your lab or “skunkworks.”  And it is ok to share that you are.

Innovation means that you don’t have all the answers.  It needs to be a place where you can test and fail and test again.  Just remember—testing for testing’s sake isn’t the goal.

Successful innovation requires you to:

·       Test with purpose. Identify a problem (e.g., reducing customer implementation costs) and explore how technology (like AI) could solve it.

·       Fail fast, learn faster. Not every test will succeed—but the lessons inform future success.

·       Engage multiple teams. Sales, support, customer success, and marketing all bring perspectives that shape whether an innovation is viable and valuable.

Innovation doesn’t happen in a vacuum. Cross-functional involvement ensures experiments can actually make it to market.

Managing Expectations

Yes, innovation items should appear on your roadmap—but as innovation initiatives, not promises. Share what you’re exploring without committing to specific outcomes until the ideas are validated.

Successful innovations may push existing items off the roadmap. Unsuccessful ones may quietly disappear. Both outcomes are healthy.

How Much Time Should Innovation Get?

In earlier posts, I argued that:

·       At least 50% of time should go to executing the roadmap (planned work).

·       Less than 50% should go to support and maintenance.

 So where does innovation fit in?

·       There must always be some space for it.

·       The share depends on market speed and competitive pressure.

·       When change is accelerating, innovation time needs to expand—the key is to provide balance by reducing support and maintenance work that may be considered non-essential now with new innovations.

Managing your technology portfolio means balancing all three deliberately—support, roadmap, and innovation—so your organization can do right, and be effective.

Support keeps the lights on.
Roadmaps guide the way forward.
But innovation is what ensures you’ll still be relevant five years from now.

📅 To bring it all together, join me at the Project Insight webinar “Shaping Your Company’s Future with Your Project Portfolio”—where we’ll translate these ideas into practical steps for your organization. 

Register:  https://projectinsight.com/project-management-webinars/turning-projects-into-strategy?c=20251001-ref-coreconcepts

Enterprise Portfolio Management — The Importance of Roadmaps

Do Right. Be Effective.

Welcome to part 3 of my 4-part series on managing technology portfolios. In part 2, we looked at the cost of over-investing in support and maintenance. Now, let’s shift from firefighting to planning—and explore how roadmaps shape your organization’s ability to deliver on its goals.

Why Roadmaps Matter

An organization’s successful future depends on its ability to deliver on planned goals. In technology, that means the roadmap (aka portfolio). Key questions every team should ask:

• How far ahead does your roadmap extend?

• What belongs on it—and how is that decided?

• How often should it change?

• How much time should be devoted to executing roadmap initiatives?

Most organizations (outside of very large enterprises) plan with a 3–5 year roadmap. Early-stage companies may look shorter-term while they search for their niche.

Sharing the Roadmap (Even When It Changes)

Too often, companies hesitate to publish or even discuss their roadmap because they expect it to change. But that’s a mistake. A roadmap is more than a static plan—it’s a tool to:

• Communicate strategy

• Spark conversations with executives, sales, employees, and customers

• Align around where the market is headed

Changes aren’t the problem. Avoiding transparency because you fear explaining change is the problem.

Building Roadmaps with Real Input

A roadmap should be based on both industry trends and customer feedback. Data sources include sales, marketing, support, customer success, and end users. Build a process for engaging regularly and collaboratively, inside and outside your organization.

If there’s no clear “why” behind roadmap decisions, executives and employees will struggle to explain them—or avoid sharing altogether—leaving prospects and customers uncertain about committing to your organization.

How Much Time Should Roadmaps Get?

In part 2, we explored how support and maintenance should consume less than 50% of your team’s time. Where should that time go instead? To the roadmap.

Organizations should aim to spend at least 50% of their time on non-urgent but important planned work—the initiatives that bring the roadmap to life. That includes:

• Executing roadmap projects

• Reviewing market and customer feedback

• Adjusting priorities to validate or update the plan

When organizations consistently execute on near-term (1-year) roadmap goals, they prove they can use critical and scarce resources effectively. Even if years 2 or 3 shift, success in the short term builds confidence and credibility with customers and employees.

In short: support keeps the lights on, but roadmaps light the way forward.

📅 Stay tuned—next we’ll talk about innovation and how to make space for it in your portfolio. And don’t forget: we’ll bring all of this together in an upcoming webinar with Project Insight, “Shaping Your Company’s Future with Your Project Portfolio.”

Technology Portfolio Management Starts with Support

Do Right. Be Effective.

Welcome to part 2 of my 4-part series on managing technology portfolios. In this post, we’ll explore where your team spends its time—and how too much focus on support and maintenance can quietly sabotage your organization’s future.

Start by Measuring Time

At the end of each week, ask your team two simple questions:

1. How many hours did you work this week?

2. Roughly what percentage of that time went to:

• Support & Maintenance

• New work for a client or product

• Innovation

Don’t make this complicated. Gather responses from across the organization—project managers, business analysts, engineers, support teams, QA, customer success managers—and then summarize the totals. Were you surprised by the percentages?

Research shows that support and maintenance often consume more than half of IT budgets, leaving little capacity for innovation and growth. (source) If your team is spending 50% or more of its time on these activities, it may be time to rethink resource planning.

The High Cost of Too Much Support Work

• Clients leave frustrated with performance and look for alternatives.

• Teams burn out as they spend every day fighting fires.

• Sales struggles to offer the new capabilities your market is ready to pay for.

A Framework to Break the Cycle

The first step forward is to categorize support requests using the Urgent/Important Matrix:

• Urgent & Important: Issues with measurable client impact—these must be fixed.

• Important & Not Urgent: Link to your roadmap—avoid quick fixes; build long-term solutions. (We’ll explore this more in the next blog.)

• Urgent & Not Important: Issues that seem urgent but may have simple work-around that clients are supportive of. Monitor these. Communication with clients is critical here, and if volume grows, they may move categories. 

• Not Urgent & Not Important: Track them, but deprioritize. These are “nice to haves” that may become innovation backlog items.

If your organization isn’t categorizing support this way, you’re likely diverting too many resources away from the initiatives that truly drive growth.

📅 Don’t forget—this series will wrap up in an upcoming webinar with Project Insight: “Shaping Your Company’s Future with Your Project Portfolio.” That session will bring the blogs together into a practical roadmap you can apply in your own organization.
👉 Register here: https://projectinsight.com/project-management-webinars/

#DoRightBeEffective #ProjectPortfolio #Leadership #Innovation

Future-Proofing with Technology Portfolio Management

Do Right. Be Effective.

Welcome to my third post in my Do Right. Be Effective. series.

This week, senior leaders in the Wealth Management industry gathered in Huntington Beach, CA for the Future Proof conference—a meeting point for innovation, strategy, and the future of business. It sparked a bigger question: how can companies ensure they are truly future-proof?

After decades of working with start-ups and small technology companies—and watching both successes and failures—I’ve seen one theme emerge: the way you manage your technology portfolio of projects determines your long-term viability.

Here’s the challenge:

• Innovation without effective execution is bound to fail.

• Moving too soon to market can backfire, opening the door for competitors.

• Moving too slowly leaves space for nimble disruptors to leapfrog laggards.

Today, AI is the next big disruptor. But how prepared is your organization to thrive—not just experiment—when the stakes are this high?

Over the next three weeks, I’ll explore how technology firms can organize their portfolios across three critical areas: maintenance/support, product development, and innovation. When managed and coordinated deliberately and effectively, these pillars allow organizations to scale with purpose and avoid the pitfalls that stall growth.

Do Right. Be Effective.
Welcome to the first post in my Do Right. Be Effective. series.

So what do I mean by this phrase?

Over my 40+ years as a project manager, I’ve seen projects succeed brilliantly and others fail spectacularly. Each one has been a lesson — and the biggest takeaway is this:

👉 Too often, project teams focus on doing things right instead of doing the right things.

That’s the difference between efficiency and effectiveness.

• You can be efficient at solving problems.

• But if you’re solving the wrong problem, your project is still at risk.

A Common Example:
A project manager runs a solid meeting, identifies new issues, and assigns them out. A team member then spends 10 hours fixing the issue before the next meeting. At the update, the problem is solved — but now that person is behind on critical path tasks that actually determine project success.

The result? The project slips, even though the team was “efficient.”

The Lesson:
Success requires prioritizing the right work at the right time.
This blog series will share pitfalls I’ve seen — and how to avoid them — by adopting a Do Right. Be Effective. mindset.

Do Right. Be Effective. Because success comes from focusing on what truly matters.