As an advisor, I often observe middle-market sellers navigating the emotionally charged task of selecting the right investment bank to represent them in the sale of their company. It frequently prompts me to reflect: How would I approach this decision? While the question is rhetorical—many on our team have been on both sides of a transaction, as owners and advisors—it’s a worthwhile exercise. Too often, we’ve seen companies take the wrong approach and suffer avoidable setbacks in the process.

Here’s how I would proceed…

If I were in the seller’s shoes, I would begin by identifying a few reputable investment banking firms. Research shows that lower middle-market sellers typically evaluate around 1.7 firms before making their final decision. However, despite the flexibility that many deals may offer, there’s usually just one real shot to get it right. That’s why taking the time to find the right fit is a worthwhile investment. I’d likely source one or two local firms through trusted professionals—CPAs, attorneys, or wealth managers—while also considering regional or niche-specific firms found through independent research. While industry expertise can be valuable, it’s not as critical today as it once was.

Before stepping into any meeting, I would come prepared with a set of key questions for each investment bank presenting. These would include:

• What relevant experience do you have in my industry or market?
• What valuations are you seeing in my specific niche?
• Based on current market conditions, what sale price do you believe is achievable?
• How do you see valuations differ between strategic and financial buyers?
• Can you provide an estimate of my after-tax, after-fee proceeds? (This may require collaboration with CPAs or financial planners.)
• Can you walk me through your typical deal process?
• What is the estimated timeline for completing a transaction?
• What are your engagement and success fees?

I might even share these questions ahead of time, asking that they be addressed directly in their presentations. This approach helps ensure that conversations are focused, transparent, and productive. It also allows me to better compare the firms on meaningful criteria rather than surface-level impressions. Ultimately, the goal is to choose a partner who not only understands the numbers but also aligns with my long-term goals and vision for the business. Taking this extra step can make all the difference in finding the right fit.