3 Transaction Comments You Never Want To Hear (or Say)

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Selling your business is but one of the significant transactions or deals a company, its owners, and its management will navigate over the course of the business journey. While all deals have their unique nuances and circumstances, an outright sale can be one of the most meaningful, most difficult, and most scarce (many business owners will only do it once). Given the most common sale objective – maximizing the value of the enterprise – we can think about successful sale preparation and execution as a template for other transactions, since every deal a business executes is geared toward preserving, increasing, and/or realizing the value of the company.

With that said, here are three statements you never want to hear or say when it comes to these processes.

“I didn’t see it coming.”

Two of our core mantras are that businesses should always ready to transact, and that the way to get the best terms on any future transaction is to run your company as well as possible today. While any specific transaction may not be a current high priority, or even on the radar screen, this really should not matter. Every business should operate as if a deal might be on the table tomorrow.

Operating from a place of transaction readiness helps prepare for the best and worst case scenarios. In a perfect world, every business leader and owner would be prepared if a major competitor came knocking at the door and said, “Hey, I’m retiring. Do you want to buy my business?” On the flip side, sometimes transaction requirements arise from negative circumstances. Business owners need to be ready if illness or another life event triggers a need to leave or sell the business immediately. Surprises hurt a lot more on the downside than they feel good on the upside.


There are plenty of business owners who are opposed to certain transactions, and for understandable reasons, such as passing the business down to the next generation. While that is an admirable goal, I often challenge these same owners to think how this mentality would shift if someone knocked on their door tomorrow and offered them a billion dollars. I could be wrong, but I think many of those same owners would change their tune.

The “-ism” here is that there are no bad assets, just bad prices. Everything is for sale all the time under one major condition – the right price. I will caveat that dollars aren’t the only measurement of price or cost, as there are many intangible and emotional components that also feed into the calculus. The point here is that strictly holding to one path or targeted outcome can cloud decision-making and leave you blind to opportunities that may be available if your lens remains wide. Never say never.

“I want to transact…yesterday!”

Out of the three comments you never want to hear, this one may be the worst. Now there is a clear desire to transact, but the timeframe may be condensed (as in, it’s got to be now) and the business owner may not have taken the steps to prepare for a successful transaction process. We should distinguish this from the first comment, which is more about an external event forcing our hand or presenting an opportunity upon which we are unable to capitalize. Here, we are talking about the realization or inflection point when an owner says, “I’m ready.” You want to be ready for when you’re ready.

Transaction processes are time consuming and take critical leaders away from their day jobs. Sourcing capital partners, preparing marketing materials, assembling due diligence requests, meeting with buyers/investors, negotiations, iterating legal documentation, and managing communication (employees, customers, vendors) – there is a lot to do! When your transaction runway is three years instead of three weeks, you have a lot more flexibility to prepare accordingly and set yourself up for an efficient process. Plus, you are in a stronger negotiating position if you have time on your side versus working against you. Important note: it doesn’t take three years to get ready.

Cumulative, Not Static

Transactions are cumulative processes, not static events. By projecting out the impact of today’s decisions on future potential outcomes (including transactions), we successfully frame those decisions in the context of an incontrovertible goal – value creation. Then, by successfully preparing for and running an efficient process, we get at the other goal – realizing and maximizing the value that has been created.

Are you transaction ready? Growth ready? Finance ready? You can find out with our complimentary assessment tool, FiRe Score! Also, we invite you to check out our whitepaper, Capital Raising & Transaction Preparation, to help you proactively take control over your transaction process. If you enjoy our content, subscribe to our newsletter to receive the latest direct to your inbox.