Professional regrets are often viewed as mistakes to move past. But according to Daniel Pink, bestselling author and 2027 AFP FP&A Forum Opening Keynote speaker, regret can be one of the most valuable sources of learning.

In a conversation with AFP’s Director of FP&A Practice Bryan Lapidus, FPAC, Pink described regret as "our most instructive emotion," arguing that it reveals what we value and can help us make better decisions in the future.

To see what that looks like in practice, we asked members of the AFP FP&A Advisory Council to reflect on a professional regret and the lesson it taught them. Their responses reveal how experiences involving stakeholder alignment, accountability, decision-making and professional development became lessons they carried forward throughout their careers.

While their situations varied, many pointed to the same underlying challenges, mirroring three of the recurring regret themes Pink identified in his research: connection, boldness and foundation.

Key Takeaways

• Build alignment before decisions are made. Many finance leaders regretted entering critical conversations without stakeholder buy-in, clear ownership or shared expectations.
• Balance speed with rigor. Finance leaders cautioned against sacrificing legal rigor, expert input or data integrity in pursuit of faster decisions.
• Turn career gaps into development opportunities. Some finance leaders reflected on missed opportunities to build technical skills, strengthen attention to detail or accelerate their professional growth.

Connection Regrets: Lessons on Relationships, Alignment and Influence

For finance professionals, outcomes depend not only on strong analysis and technical expertise but also on bringing the right people into the process, building alignment before key decisions and engaging stakeholders while there is still time to influence the result.

This idea of reaching out before it’s too late is central to Pink’s concept of connection regrets. Pink describes these as regrets arising from frayed, undone or incomplete relationships and centered on the thought, “If only I’d reached out.”

In a professional context, Pink’s broader lesson about the importance of connection can apply both to building a network of trusted relationships over time and to bringing the right people into individual decisions. The following examples show what AFP FP&A Advisory Council members learned when alignment, stakeholder involvement or collaboration came too late.

Entering a Critical Meeting Without Consensus

Alignment issues often emerge before decision-makers ever enter the room. Tyler Vonderheide, Senior Manager, FP&A, Southwest Airlines, shared, “I regret going into a steering committee meeting unaligned with my VP.”

When you’re not on the same page walking into a meeting with high-level stakeholders, you reduce the likelihood of gaining consensus on a proposed course of action. The lesson is to surface disagreement early enough to resolve it or, at minimum, to enter the room with a shared understanding of where the differences lie.

Sacrificing Legal Rigor for Transaction Speed

The pressure to keep a transaction moving can make review processes and stakeholder involvement feel like obstacles. But bypassing those safeguards often creates bigger problems later.

One finance practitioner explained, “During an M&A transaction, the team moved forward with a decision before securing proper stakeholder alignment, and the term sheet wasn’t drafted with sufficient legal rigor due to time constraints. As a result, the terms became ambiguous during final negotiations, introducing avoidable risk and uncertainty.”

Through this experience, the finance practitioner learned the importance of involving qualified counsel early to ensure the negotiated terms are both technically enforceable and realistically achievable.

Prioritizing Analytical Perfection Over Timely Collaboration

FP&A professionals are trained to value rigor and precision, but analysis creates value only when it reaches decision-makers in time to influence an outcome.

“One of my professional regrets is not recognizing earlier that great analysis alone is not enough,” said Wesam Alayyad, Head of Financial Reporting & Analysis, Jeddah Airports Company. “I learned that engaging stakeholders early and delivering timely insights often creates more value than pursuing technical perfection.”

Engaging stakeholders early helps finance understand the decision behind the request, test assumptions with the people closest to the business and deliver insight while there’s still time to act.

Boldness Regrets: Lessons on Judgment and Execution

Finance leaders sometimes face situations where the easier response in the moment can create a bigger problem later. Taking on an issue that belongs to another function may keep things moving, but it can also blur accountability. And while postponing a difficult accountability conversation may avoid immediate conflict, it allows underlying problems to persist.

Pink describes boldness regrets as those that arise when people hesitate at a crossroads and choose safety over taking a chance, leaving them with the thought, “If only I’d taken the risk.” In the workplace, that broader lesson about courage can apply when sound judgment requires accepting discomfort rather than avoiding it.

The following examples show what AFP FP&A Advisory Council members learned from choices that avoided short-term discomfort but created longer-term problems.

Becoming the Default Owner of Non-Finance Problems

Finance often sees the consequences of broken processes before anyone else because those problems eventually show up in budgets, forecasts and financial results. That visibility can create pressure to step in and solve issues that belong to another function.

“I regret the times I took on problems simply because others (who are really better placed to solve them) kept avoiding them,” said Connagh Hopkins, Head of Financial Performance, Murdoch University.

Hopkins noted that stepping in can create role ambiguity, confusion within the finance team and, ultimately, leave finance accountable for outcomes it doesn't control. She explained that the better response is to make the problem visible, help define the solution and support the function that owns it.

Delaying Difficult Accountability Discussions

Accountability doesn’t become easier with time. Delaying the hard conversation only widens the performance gap, sending the unintended message that the results are acceptable.

Barry Huisman, CFO, Oil & Gas, UCC Energy, shared, “I regret waiting too long to hold a business leader accountable for underperformance.”

Addressing performance issues early gives the person an opportunity to respond, creating space for course correction and protecting the organization from a larger problem later.

Foundation Regrets: Lessons on Growth and Core Capabilities

Strong foundations matter in finance because weaknesses that seem manageable in the moment can have broader consequences. Compromising data integrity can erode trust in the work, and underdeveloped technical skills or attention to detail can limit learning and effectiveness over time.

That compounding effect is central to Pink’s concept of foundation regrets. Pink describes them as regrets that arise from failing to build a stable base for the future and realizing later how earlier choices can create longer-term challenges. The experiences below shared by AFP FP&A Advisory Council members show how those consequences can surface in finance careers.

Allowing Speed to Undermine Data Integrity

Deadlines create pressure to deliver answers quickly, but finance credibility depends on getting critical information right.

“Everyone wants something fast until the speed compromises the quality,” said Bryan Lapidus, FPAC, Director of FP&A Practice, Association for Financial Professionals. “I remember the COO of my company throwing a 60-page presentation at me because he found a wrong number. He said, ‘How can I trust anything in here?’”

A single incorrect number can cast doubt on every correct one around it. Data integrity is the very basis of finance’s credibility. Finance leaders need to distinguish between directional analysis and work that must be exact, then set expectations about timing accordingly.

Underinvesting in Technical and Data Science Skills

A common career regret is not developing skills early on that, in hindsight, have become critical to career growth.

“I regret not having a stronger accounting and/or data science background,” said one finance practitioner. “I would have benefited from more academic work in those areas, so I lean heavily on my financial controller and data science teams.”

The finance practitioner is seeking out the missing knowledge while also relying on colleagues with deeper expertise. That combination of continued learning and collaboration demonstrates that foundational skill gaps don’t have to become permanent limitations.

Underestimating Early Attention to Detail

Professional habits developed early in a career can shape future opportunities just as much as formal expertise.

“I wish I had been more detail-oriented within the first three years of my career,” said Marcus Gadson, AVP of Capital Management, Ascension. “It would have generated more learning experiences and stronger relationships with internal business partners.”

Attention to detail early in your career is about more than preventing mistakes. It accelerates learning, demonstrates respect for the people relying on the work and builds a reputation for dependability. While this regret focused on the beginning of a career, the lesson remains relevant at any stage: Precision is a professional habit you can always strengthen.

How Confronting Past Missteps Shapes Better Decision-Making

The regrets that finance leaders shared were not career-defining failures. They were moments that changed how they approached stakeholder alignment, accountability, decision-making and professional development.

That reflects the point Daniel Pink made in his conversation with AFP. The professional regrets we remember most often reveal what matters to us and can shape how we approach future decisions.

At the 2027 AFP FP&A Forum in New Orleans, March 22-24, Pink will expand on those ideas in his Opening Keynote, “Beyond Resilience: A New Path to a Strong Culture,” exploring how organizations can use reflection to improve decision-making and strengthen performance.