Any person who has bought more than a handful of businesses has undoubtedly run into a challenging seller. You probably know the type of seller I am referring to: they are hesitant to hand over requested information, they make very strong (and sometimes seemingly nonsensical) demands, they may be unsure about continuing with an accepted offer, and yet they push for a faster and faster closing. Working with a challenging seller can be extraordinarily stressful – believe me, I’ve worked with my share of challenging clients. But with a little understanding, and following a couple of simple principles, you can bring most deals with challenging sellers to a successful (and happy) closing. Here are some tips for working with a less-than-helpful seller.

1. FOUR TIPS FOR DEALING WITH
A CHALLENGING SELLER
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2. Why are Sellers Challenging?
Here’s 4 Reasons.
They’re
Discovering
Their Way for
the First Time
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It’s personal to
them.
They are more
risk averse than
you.
They are scared
of being ripped
off.

3. They’re Discovering Their
Way for the First Time
• Most sellers are navigating
a complex process for the
very first time.
• Even if they have sold few
businesses in the past ,
they are still faced with new
decisions.
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4. It’s Not Just Business, It’s
Personal
• You may see their business as
just assets, revenues, and
earnings.
• For the seller, though, the
business is a part of their
personal identity.
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2

5. Risk Aversion and Tolerance
Even though you take on more
risk when you buy an online
business, you also likely have
more risk tolerance. Sellers
usually have very little risk
tolerance.
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3

6. Fear of Being Ripped Off
Finally, some sellers are simply
paranoid that, by revealing
details to a prospective buyer,
their idea or “secret sauce” may
be stolen.
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4

7. Tip #1: Never Draw a Line
Lines Make More Lines
7
Drawing a ‘line in the sand’
usually causes a seller to draw
their own line. This leaves you
with two people who have set
up “uncrossable” boundaries,
and it effectively kills any hope
of a deal.

8. Tip #2: Make Guidelines Clear
8
One of the single most
important tenets of effective
negotiation is to make your
goals, requirements, and
expectations extraordinarily
clear from the beginning.

9. Tip #2: Make Guidelines Clear
9
Put a Seller at Ease by Following 3 Principles:
Spend More Time on
Your Initial Due
Diligence List
Give Timelines (and
stick to them)
Discuss
Discrepancies

10. Tip #3: Work with the Broker,
Not Against
10
If you find yourself making reasonable
requests of your seller, and your seller
is challenging those requests, chances
are strong that you are not the only
person who is frustrated. The broker’s
goal is the same as yours: to try and
bring the transaction to a close and to
work through unreasonable objections.

11. Tip #3: Why a Broker Helps.
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The Seller Chose
the Broker
Experience Less at Stake
A seller doesn’t
necessarily get to “choose”
you – they choose your
offer. As a result, you need
to work to gain the seller’s
trust.
It is hard to stand that up
to a broker who likely has
worked with hundreds, if
not thousands of clients
and potential clients over
the years.
A broker has
proportionately less at
stake than both you and
the seller. The broker has
less to gain and less to
risk.

12. Tip #4: Be Willing to Walk Away
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If you are dealing with a challenging seller,
sometimes the best option is to just walk
away. There will be more opportunities,
and honestly, the vast majority of sellers
are really quite reasonable and easy to
work with.
Finding that right acquisition can take a
very long time, especially for cautious
buyers, and when the only real impediment
seems to be the seller, it can be tempting
to try and push through that and just close
the deal.