“Transactions are about two things: transfer of ownership and allocation of risk,” observes Gavin McGuire, seasoned business advisor and former tax partner, during a recent Platforum9 session. Drawing from his unique career trajectory—from corporate lawyer to tax specialist to business advisor—McGuire shares insights on what makes deals succeed or fail in today’s complex business environment.
The Evolution of Deal Advisory
After years as both a corporate and tax lawyer, including time with leading firms and PricewaterhouseCoopers, McGuire has witnessed how different professional perspectives can shape transaction outcomes. “Tax can drive whether a transaction takes place or not,” he notes, “but how that transaction takes place is often determined by tax.”
This multilayered understanding has led him to advocate for a more holistic approach to deal-making, one that looks beyond immediate transactions to consider longer-term business journeys.
Common Deal Breakers
McGuire identifies several key factors that frequently derail transactions:
- Lack of preparation, often due to opportunistic circumstances
- Unrealistic expectations from either party
- Unwillingness to compromise as deals progress
- Breakdown in communication between parties
- Attempts to change agreed terms late in the process
“I always say at the start, this is not going to be comfortable,” McGuire explains. “There’s going to be bad days, but at the end, once we get the results you want, it’s all worth it.”
The Power of Transparency
One of McGuire’s core principles is the importance of owning your narrative—both strengths and weaknesses. He shares an example where a transaction initially failed because issues were downplayed in vendor due diligence. When the same company later approached the market with complete transparency about its challenges, it achieved a better outcome.
“Own your narrative, own all the things that you do good and all the things you do bad,” he advises. “Always put it out front in a conversation if you’re trying to do a transaction.”
The Role of Legal Teams
While lawyers play a crucial role in transactions, McGuire suggests the profession could learn from the Big Four accounting firms’ approach to project management. “Even on something you’ve done multiple times, get one of your colleagues to bounce it off them,” he recommends, citing the value of “four-eye review” processes.
He also advocates for dedicated project managers on larger transactions, noting that expecting corporate partners to both negotiate and manage complex deals may be unrealistic. “If you have a project manager ensuring everybody’s moving at the same speed at different parts of the transaction process, it’s going to lead to a much more efficient and better result.”
Current Market Trends
Despite global volatility, McGuire observes that deal activity remains strong, though transactions are taking 20-30% longer to complete than previously. “That volatility hasn’t stopped the movement of cash,” he notes. “It’s just more about the timing and execution and the allocation of risk as part of that transaction.”
Looking Forward
For successful deal execution, McGuire emphasizes several key elements:
- Early involvement of all necessary advisors
- Clear communication throughout the process
- Regular in-person meetings for resolving blockers
- Transparent fee discussions and early communication about any overruns
- Focus on building long-term relationships rather than just closing deals
As he concludes, success in deal-making isn’t just about technical expertise—it’s about understanding human dynamics, managing expectations, and maintaining clear communication throughout the process.
