Selling a business is often the largest financial transaction an entrepreneur will ever undertake. Yet many owners underestimate the time, preparation, and scrutiny involved once a deal enters the due diligence phase.

In this episode of Are You Ready?, Neil Cockburn is joined by Hugh Watt, Chief Operating Officer of Acera Insurance, to explore the realities of due diligence during a business sale or acquisition. Hugh brings firsthand experience from multiple transactions, both on the buying side and the selling side, and shares lessons learned from helping guide companies through successful transitions.

The conversation covers what business owners should expect once a letter of intent is signed, why due diligence often takes longer than anticipated, and the importance of assembling the right team of advisors. Hugh discusses everything from quality of earnings reviews and financial reporting to confidentiality, management presentations, and the challenges of keeping a business running while simultaneously preparing for a transaction.

One of the key messages throughout the episode is that preparation creates options. Business owners who invest in strong systems, accurate reporting, and experienced advisors are far better positioned when an opportunity arises. Hugh also shares practical insights about deal fatigue, valuation expectations, legacy considerations, and why successful transactions are about much more than simply reaching a purchase price.

Whether you're considering a sale in the next year or the next decade, this episode offers a valuable look at one of the most critical phases of any business transition.

About Hugh Watt

‍
Hugh Watt is Chief Operating Officer and Partner at Acera Insurance, where he helps lead operational strategy, partner integration, and growth initiatives across the organization. With more than 20 years of senior leadership experience in insurance, professional services, finance, and operations, Hugh has played a key role in numerous mergers, acquisitions, and business transitions.

Throughout his career, including leadership roles with Foster Park Brokers, NFP, Nilex, and Acera, he has worked closely with executive teams through acquisitions, ownership changes, post-transaction integration, and strategic growth initiatives. His practical experience on both the buy side and sell side of transactions provides a unique perspective on the challenges and opportunities business owners face when preparing for a sale or acquisition.

Known for his disciplined, execution-focused leadership style, Hugh is passionate about helping organizations navigate change while maintaining a strong focus on people, culture, and long-term success.

About Neil Cockburn

‍
Neil Cockburn is a Chartered Professional Accountant (FCPA), Family Enterprise Advisor (FEA), and Trust and Estate Practitioner (TEP), and the Director of Family Enterprise Advisory Services at Kingston Ross Pasnak LLP. With more than 40 years of experience working alongside business owners and family enterprises, Neil specializes in succession planning, intergenerational wealth transition, and estate strategy. He is known for helping families navigate complex transitions with clarity and confidence—always grounded in one central question: Are you ready for what comes next?

‍

To learn more and connect with Neil Cockburn of Kingston Ross Pasnak, please visit: https://www.krpgroup.com/our-people/neil-cockburn

This video podcast series is proudly produced by the team at Road 55 - located in Edmonton, Alberta. For more information, please visit: www.road55.ca