When negotiating a deal, M&A or otherwise, the order in which you tackle issues can make or break the outcome.
Some negotiators want first to lock in the headline terms, such as valuation, structure, and key economics (the big stuff).
You know if there’s a deal before racking up time.
But you risk locking yourself into a price before you’ve built any trust or goodwill in the negotiation process.
Others start with the small stuff, such as employee matters and operational details. Often, some of these “small” things can be essential to the vendor but may be lost if left to the end.
You build momentum and bank easy wins.
But you risk deal fatigue before ever agreeing on the hard points.
For example, I once advised a seller whose top priority was ensuring two key employees had retention bonuses and clearly defined roles post-deal.
If we’d left that until the end, the issue could easily have been squeezed out during final price negotiations or seen as a bargaining chip against valuation.
By surfacing it early, we secured agreement while goodwill was high. It even reassured the buyer about post-deal stability, strengthening their confidence in the deal overall.
Personally, I lean toward a hybrid approach:
Confirm directional alignment on the big stuff early (so you know you’re in the right ballpark).
Then work through smaller items to build trust and momentum.
Finally, tackle the thorny issues when everyone’s invested enough to want to get it done.
