When it comes to selling your business, choosing the right investment banker is a crucial step. Frank Williamson, founder and CEO of Oaklyn Consulting, shares his insights on what questions business owners should ask before making this important decision. You can read his full column over at Forbes, but here’s a brief overview to get started.

Why These Questions Matter
Selling one’s business is a significant milestone, and for most business owners, it’s a once-in-a-career event. Investment bankers function as strategic partners who guide business owners through complex negotiations and tough decisions. It’s essential to find the right fit in expertise, approach and communication style to ensure a smooth process and successful transaction.
Four Key Questions to Ask
How Does Hiring You Benefit Me?
A good investment banker should be able to explain their strategic approach, provide clear expectations and support you throughout every step — from preparing the business for sale to closing the deal.
Would You Even Want to Work with Me?
Confirm that your investment banker specializes in your industry and transaction size to avoid surprises and ensure you receive their focused attention. Boutique firms may offer more personalized service, while larger banks often handle bigger, less complex deals.
What Does Assisting Me During the Business Sale Journey Look Like?
Selling a business often takes 10 to 12 months. It’s important to understand how involved your banker and their team will be — from managing documentation to negotiating and resolving unforeseen hurdles.
Would Your Past Clients Recommend You?
Seek direct references to learn how your banker works in practice, instead of solely relying on testimonials or promotional materials.
Read More at Forbes
Deciding to work with a particular investment banker often goes beyond credentials. It’s about finding a transparent, communicative partner who shares your business goals and supports you through every phase of a sale. For a deeper dive into Frank’s insights, check out his full Forbes column here.