4 Keys to Making a Deal That’s a
Keeper
These
simple steps to take early on in any negotiation will save time and money and
increase the likelihood that the arrangement will be one you can live with.
EXPERT OPINION BY HOWARD TULLMAN, GENERAL MANAGING PARTNER, G2T3V AND CHICAGO HIGH TECH INVESTORS @HOWARDTULLMAN1
Nov 4, 2025
One of the first things
they teach young corporate lawyers is to leave the ugly and difficult stuff to
the very end of negotiations, when the parties are weak, tired and sick of the
entire proceedings. In fact, the most experienced M&A attorneys will admit
that an even better idea is to paper over the present and future problems, push
the tough questions down the line, and leave the heartaches and the lawsuits to
the next group of bloodsuckers. They tell you that your litigation partners
will thank you in advance for their future fees.
This concept is also a
critical part of the ground rules and gospel of all divorce lawyers, regardless
of which side of the argument they happen to be on. No one who’s ever been
there believes for a moment that these avaricious advocates can serve anyone’s
interest but their own. The basic idea—after creating every delay possible in
the proceedings and wringing all the fees possible out of their victims—is to
get some closure so they can get on to their next case and never look back.
For the perspective of
any poor entrepreneur sucked into one of these seemingly endless negotiation
sessions, there really isn’t any simple or foolproof way to avoid the mess.
There is, however, one rule to absolutely keep top of mind throughout the entire
process. The easier the deal is to get done, the harder it will be to
implement. This is why it’s your basic job to be difficult when it
matters, regardless of what your own attorneys argue or caution and
notwithstanding all the pressure from everyone else in the room to just get
things done. This is a difficult position to put yourself in and it takes a
while and a few different attempts and contexts to develop the thick skin,
blank stare, and willingness to ask the same questions over and over until you
get a solid and clear answer to them. You need to forsake peace for truth
telling. The price you pay for momentary peace is always too high.
All of which is
presently and painfully on display as the world watches Trump’s latest deluded
lie about bringing peace to the Middle East fall apart in just days after it
was touted and paraded everywhere. It was foolish, naïve and embarrassing for
experienced negotiators and the public at large to think for a moment that an
agreement with dozens of deferred terms and concessions including disarmament
of Hamas and its expulsion from Gaza would ever come to pass in the absence of
further military intervention. Once again, the Trump art of the deal turns out
to be a fraud on us all. It appears that Putin’s not the only one to make a
fool repeatedly of the Orange Monster. China’s leader, Xi Jinping, also just
made Trump look like a clueless clown by giving back a small fraction of what
China took away in exchange for major further concessions by Trump trying to
save face as he backs away from a tariff battle that he stupidly started.
But even this miserable
example provides simple negotiating lessons for entrepreneurs in their own
business dealings. There are a few simple steps to take early on in any
negotiation in order to save time and money and significantly increase the
likelihood that the ultimate arrangement will be one that you can live with.
1. Start at the end, not
the beginning.
Make it clear that
certain basics are non-negotiable and that they are absolute requirements for
getting any deal done. Don’t let these be deferred or glossed over. You
should never deny your firmest convictions for the sake of peace and quiet. There
is zero chance that Hamas will ever give up its weapons and only a fool would
believe otherwise. They’ve said it before the ceasefire and now they’ve said it
after the ceasefire—even going so far on TV as admitting that it’s only a
“hudna” which means a pause. On the other hand, Mamdani campaigned for Mayor in
the NYC primary on some very risky propositions and made some over-the-top
promises and, to his credit, he has maintained those stances, for better or
worse, and even doubled down on some which has made his position abundantly
clear to all.
2. Stick to your guns
and stand alone if necessary.
Everyone in any meeting
will have their own agenda, including the folks on your side and the
professionals working for you. It’s rare that all these will be aligned. Open
declarations and consistent clarity on your part will save everyone time. It’s
far better to be an asshole in the moment and even risk the deal than to suffer
years later with an agreement, terms, and conditions that you knew wouldn’t get
the job done but settled for in order to keep the peace. Seeking consensus on
aggressively contested points is more likely to lead to a mediocre outcome than
to a happy ending.
3. Acknowledge that some
deals just can never get done.
Wishing, hoping and
beating a dead horse aren’t ways to get where you want to go. Sometimes, you
just can’t get there from here and it’s smart and prudent to acknowledge that
as soon as it’s clear. If you sit there long enough, all that happens is that you
get subjected to a constant stream of asks for compromises, small concessions,
deferments or flat out give-ups—all in the name of good faith, false hopes and
sharing the pain. It’s like being slowly pecked to death by a flock of angry
geese.
4. Remember the rule of
the slippery slope.
Every negotiation
contains a number of detours, rabbit holes, and slippery slopes which all need
to be avoided. Detours and rabbit holes merely waste your time. Slippery slopes
are outright dangerous because they’re inducements and invitations to settle various
matters for everyone’s sake except your own. But even worse is the end result.
You need to always remember the rule: the minute you settle for less than you
deserve, you get even less than you settled for.
