What Career Lessons Can Be Learned from a Deal that Didn't Go as Planned?
Ever wondered what hard-earned lessons lurk behind the scenes of investment deals gone awry? Featuring insights from a Chief Financial Officer and a Founder, this article sheds light on crucial career lessons learned from unexpected challenges. Experts kick off with the importance of verifying assumptions and conducting thorough due diligence, and conclude with the need to look beyond numbers in investment decisions. With a total of thirteen insights, this compilation offers invaluable wisdom for anyone in the investment field.
- Verify Assumptions and Conduct Thorough Due Diligence
- Manage Expectations and Stay Flexible
- Never Skip Environmental Assessments
- Prioritize Clear Communication and Set Realistic Expectations
- Communicate Regularly to Save Deals
- Align Product Timing with Market Readiness
- Ensure Alignment in Values and Goals
- Conduct Detailed Technical Audits
- Be Adaptable and Find Middle Ground
- Run Extensive Background Checks on Tenants
- Validate Assumptions with Small-Scale Tests
- Research Business Models and Market Trends
- Look Beyond Numbers in Investment Decisions
Verify Assumptions and Conduct Thorough Due Diligence
Perhaps the most valuable career lesson I learned from a deal that didn't go exactly as expected was the importance of due diligence, and not allowing assumptions to get the best of you. Early in my career, I was working on a deal, and I leaned really heavily on very optimistic financial projections that the other side had given me that I took at face value without probing as deeply into what the underlying assumptions were. Still, halfway through, unexpected liabilities emerged, and the deal's possible returns dropped sharply. The lesson was that even trusted sources must be validated and assumptions verified. For investment professionals, actionable lessons learned from this experience include source diligence being a must-have for every deal regardless of time pressure or counterparty credentials. That means looking beyond the surface and examining their financials, market conditions and operational risk. If viable, incorporate specialists to evaluate legal, monetary, and industry-associated components in a complete method. Deals are rarely clear-cut, and when risks are discovered, the ability to adjust course or negotiate terms can mean the difference between success and failure. Setting clear expectations with stakeholders upfront and providing clear communication mitigates the fallout if things don't go as intended. Finally, use failures as a way to improve your strategy. Successful or otherwise, each deal teaches important lessons about strategy, risk management, and decision-making. I hope that by following these lessons and iterating to make things better, you can turn failures into stepping stones for future success. The strongest professionals are the ones who continue learning, expanding, and evolving after every encounter.
Manage Expectations and Stay Flexible
One of the most valuable lessons I've learned is managing expectations and maintaining flexibility, especially when unforeseen challenges arise.
A particular deal stands out, where everything seemed to be going smoothly. However, midway through the process, we faced a series of unexpected setbacks—an appraisal that came in lower than anticipated, an issue with the title that wasn't discovered until the last minute, and some last-minute buyer concerns. These hurdles tested my ability to remain calm under pressure and adjust the strategy without compromising the deal's integrity.
From that experience, I learned how crucial it is to stay solution-oriented and not get bogged down by obstacles. Being proactive—addressing concerns before they become issues, maintaining open communication with all parties involved, or being willing to pivot when needed—was key to ultimately salvaging the deal.
Another critical takeaway was the value of having a strong support team. In real estate, things rarely go exactly as planned, and having a network of reliable partners—inspectors, attorneys, appraisers—who are responsive and trustworthy can make all the difference when navigating bumps in the road.
The lesson? No deal is ever truly "done" until it's done. Stay adaptable, keep communication lines open, and be prepared to adjust quickly when things don't go according to plan. These strategies are crucial for long-term success in a fast-paced industry like real estate.
Never Skip Environmental Assessments
I made the mistake of skipping environmental assessments on what seemed like a perfect multifamily property deal, only to discover major soil contamination issues after closing. The cleanup costs ate up our entire profit margin, and we had to hold the property much longer than planned. Since then, I've developed a comprehensive pre-purchase checklist and never skip steps, no matter how promising the deal looks on paper.
Prioritize Clear Communication and Set Realistic Expectations
One important career lesson I learned came from a software development deal that initially seemed promising but ultimately didn't go as planned. We had underestimated the complexity of the client's requirements, leading to scope creep and delays. The project failed to meet our original expectations, and the client's frustration impacted our relationship. From this experience, I learned the importance of clear communication and setting realistic expectations from the very start, as well as the value of constantly reassessing the project's progress.
This experience also taught me to prioritize contingency planning and to never underestimate the importance of thorough due diligence. Now, in every business venture, I make sure to establish clear milestones and open lines of communication with all parties involved. The deal didn't go as expected, but it provided valuable insights into managing risks and adapting quickly, which have contributed to more successful future endeavors.
Communicate Regularly to Save Deals
Clear communication is crucial when a deal starts going sideways - I learned this the hard way after losing a promising property deal because I wasn't up front about timeline changes. Now I make it a point to send regular updates even when there's bad news, which has actually helped save several deals that hit rough patches.
Align Product Timing with Market Readiness
During a tech investment deal, I learned a critical lesson about overestimating market readiness. We invested in a platform with incredible potential but underestimated the time it would take for target users to adopt the technology. The product was solid, but the market wasn't ready for that level of innovation yet.
In hindsight, we should have conducted deeper user research to validate assumptions about adoption timelines. Now, I always emphasize aligning product timing with market readiness, even for groundbreaking solutions. It's not just about what's possible—it's about what customers are willing to embrace today. This experience taught me to weigh timing as heavily as potential when evaluating deals.
Ensure Alignment in Values and Goals
One of the most valuable lessons I learned came from a joint venture deal I was brokering between two companies in the UAE. The proposal seemed flawless on paper, with both sides offering complementary strengths. However, as the negotiations progressed, communication issues and misaligned expectations began to surface. One company was focused on short-term profitability, while the other prioritized long-term market dominance. The deal collapsed just weeks before the launch, resulting in significant frustration for all parties involved.
My years of experience taught me that even the best business models will fail without alignment in values and goals. I revisited the situation, acting as a mediator, and facilitated a clearer dialogue between both companies. By applying the skills I honed from my MBA in finance and my military training in structured problem-solving, I helped restructure the partnership under more realistic terms. This resulted in a smaller but ultimately successful collaboration that allowed both companies to benefit. The experience reinforced the importance of communication and adaptability in business, as well as ensuring alignment from the outset to save time and resources.
Conduct Detailed Technical Audits
I learned the hard way about thorough due diligence when we rushed into acquiring a promising AI startup without properly vetting their tech stack. What looked great in demos turned out to have serious scalability issues, costing us months of engineering time and resources to fix. Now I always insist on detailed technical audits and proof-of-concept testing with real data, even if it means slowing down the deal process.
Be Adaptable and Find Middle Ground
Negotiation flexibility saved one of my trickiest deals when the seller suddenly needed a longer closing timeline due to family issues - instead of walking away, we worked out a creative lease-back arrangement. Generally speaking, being adaptable and finding middle ground has helped me close more deals than sticking to rigid terms.
Run Extensive Background Checks on Tenants
I learned the hard way that running extensive background checks on potential tenants isn't just paperwork - it's crucial protection for your investment after losing $8,000 in damages and unpaid rent from what seemed like a 'perfect' tenant. Now I always tell new investors that gut feelings aren't enough - take the time to verify everything, even if it means losing a few days of potential rental income.
Validate Assumptions with Small-Scale Tests
I learned a tough lesson when a major marketing campaign flopped because we didn't validate our assumptions about the target audience's pain points. Now I always insist on running small-scale tests and gathering real customer feedback before committing significant resources, which has saved us from several potential misses and helped us pivot early when needed.
Research Business Models and Market Trends
For example, I had an experience with a tech startup that at first seemed like a good idea. They had a groundbreaking concept, a formidable team, and a substantial investment. But unexpected market trends and execution problems caused the valuation to plummet. Although the result was disappointing, it taught me a very valuable lesson about due diligence.
We could have learned more about the business model and scaling capabilities of the company in retrospect. We underestimated competition and market disruptions, too. This experience taught me that you should research thoroughly, ask questions, and test a variety of scenarios.
Look Beyond Numbers in Investment Decisions
The biggest lesson I've learned is that research alone isn't enough - I once recommended a seemingly solid stock investment that tanked because I missed some crucial management red flags in my analysis. I now make it a practice to look beyond the numbers and dig deeper into company leadership, culture, and market sentiment before making any investment decisions.
