Direct answer: Anyone can sabotage your exit — including you. The most common saboteurs are the business owner (through emotions and fear), attorneys who kill deals for sport, spouses, adult children, business associates, and vendors. Do a saboteur audit before signing the LOI.
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Why Most M&A Deals Do Not Close
When it comes to selling a business, one of the more eye-opening things is that 8 out of 10, up to 9 out of 10 M&A deals do not close. They start, they progress, they get close to the finish line, and then they die. The reasons vary — numbers, timeline, emotions, trust, and the overall relationship inside the acquisition all contribute. But behind every dead deal is at least one specific person who acted as the saboteur.
Understanding who sabotages your exit — before the sabotage happens — is the difference between a closed deal and a story you tell for the rest of your life about the one that got away. This concept sits inside the Exit Ratio 360™ system as the risk-side analysis that pairs with the operational and financial preparation layers.
The Number One Person Who Will Sabotage Your Exit — You
Here is the uncomfortable truth I need to share up front. One of the persons who will ultimately become a saboteur in your deal will be you. Not always. But a lot of the time.
The business owner is the person who ends up destroying the deal more frequently than any other saboteur category. Not consciously. Not maliciously. But structurally — because of what happens inside the owner during the multi-month process of actually selling something they have built for decades.
You cannot address this risk if you cannot admit it exists. Almost no M&A advisor will tell you this because it implicates you as the client. That is why the first step in the saboteur audit is the honest self-audit. Are you the one who is going to sabotage your exit?
How Emotions Cause You To Sabotage Your Exit
Emotions really matter a lot, and they get in the way when it comes to business exits. You have been at this business for 10, 20, 30, 40 years. You have watched it grow from nothing to something. You have watched a lot of good things happen and you have watched a lot of bad things happen.
When the exit process starts, you have three specific emotional loads to carry:
- Grief — for what you are leaving behind, including relationships that will not survive the sale
- Fear — of what you do next when the identity of “business owner” is gone
- Identity crisis — the “what do I do next?” question that has no easy answer
Any one of these can cause you to inadvertently make bad decisions and torpedo the deal. All three at once produces even higher risk. See the founder’s post-sale identity crisis and how the fear of acceptance can ruin a business exit for the deeper analysis of both dynamics.
How Due Diligence Fear Makes You Sabotage Your Exit
The second way you sabotage your exit is through fear during due diligence. When the buyer’s team starts turning over the papers, there are a lot of different people involved. There is a lot of movement, a lot of drama, a lot of conversations.
You start to worry about specific questions:
- What are they going to say about what they find?
- What are they going to do with the information?
- What information are they going to find that they were not supposed to find?
- What can I use to my advantage now that I know they know something?
Now you have trickery going back and forth. What could have been a straight-line diligence process becomes a chess match. This can happen at the last minute. Deals get stopped, held up, or postponed because the fear-driven maneuvering damages the trust that allows the deal to close.
How Attorneys Sabotage Your Exit When You Give Them Too Much Power
There will be times where attorneys destroy your deal because you gave them too much power. Some attorneys are killer for the sake of being killer. Winning for them is being killer for their own sake, not for yours.
What they do specifically:
- Alienate the other side of the deal
- Alienate other people involved on the other side
- Use the fact that everybody is afraid of legal proceedings as leverage
- Strong-arm parts of the deal that were not actually in dispute
- Get you locked into things you do not necessarily need to be locked into
- Restrict things you should not necessarily be restricted from doing
The attorney who wins does so because you gave them the mandate to win at any cost. Sometimes that cost is the entire deal. See the five times to fire your advisor mid-deal for the specific signals that an attorney is starting to sabotage your exit rather than protect it.
The Advisor Trust Factor — How Their Reputation Prevents Sabotage
This is why picking your advisors and consultants ahead of time matters so much. Get to know them well before you need them. Have conversations with their prior clients. Understand how they do business. Look at their reputation in your industry.
Then ask the deeper question — once they get out of your industry, do they have a reputation to uphold? Or are they the lunatics who just crash deals for a living, cash the fee, and move on to the next unsuspecting owner?
There is a specific question worth asking directly: “How many deals a year do you crush?” They are not going to tell you honestly. But how they respond to the question reveals plenty. An honest advisor will laugh and give you a real number in context. A defensive advisor will pivot. A dismissive advisor will attack the question itself. All three responses are diagnostic information about whether they will sabotage your exit or protect it.
For the framework on advisor selection that prevents the crash-and-fee pattern, see before you hire an advisor or consultant, understand this one rule.
The Saboteur Audit — Everyone Who Could Sabotage Your Exit
Sit down and write out a list of everybody who could potentially end up ruining your deal. Your saboteurs. Just about anybody with information about your deal could sabotage your exit — even people who are just on the surface of it.
Categories to consider:
| Saboteur Category | How They Sabotage |
|---|---|
| Spouse | Silent veto through friction, verbal veto through direct objection, or kitchen-sink veto through relationship escalation |
| Adult children | Family dynamics around inheritance, succession, or perceived exclusion from decisions |
| Dog or emotional attachment | Sounds funny — but genuine emotional anchors to the current life can create resistance |
| Cousin or extended family | Loan requests, business investment demands, competing loyalties |
| Business associates | Partners, JV relationships, referral partners whose income depends on your continued ownership |
| Employees | Key personnel who fear the transition and either leave early or leak information |
| Vendors | Suppliers whose margin depends on you specifically; competitors of the acquirer |
| Attorneys | The “killer for the sake of being killer” pattern discussed above |
The audit exists to make each potential saboteur visible. Once visible, each one gets a mitigation strategy. Some need conversations. Some need NDAs. Some need distance. Some need to be pulled closer. The mitigation varies but the visibility is required.
The Specific Categories Who Could Sabotage Your Exit
For the human categories — spouse, kids, cousins, business associates, employees, vendors — the common thread is that they may say some version of the following: “I do not want you to do this deal because it hurts me. It hurts my business, my income, my opportunity to make what I would like to make.”
They may not say it in those exact words. They may express it through delay tactics, emotional escalation, information leaks, or open resistance. The mechanism varies. The underlying incentive is the same — your exit affects them in a way they experience as loss, and they will act to prevent the loss.
Recognizing this is not a moral judgment about them. It is an operational reality about how your exit affects everyone in your network. Understanding whose incentives are misaligned with your exit is what allows you to structure conversations that address the misalignment before it becomes sabotage.
The Pre-Exit Conversation Strategy
Have conversations with vendors, staff, and others before you exit. Explain what is going to happen and when. Depending on the level of the deal, this is very important. Sometimes when you skip these conversations, it comes back to bite you at exactly the wrong moment.
Not everyone gets the same conversation. The template varies by relationship:
- Key employees — legal NDA in place first (see how you could use an NDA to your advantage), then structured conversation with clear timeline and continuity commitments
- Key vendors — NDA and conversation about continuity of the relationship under new ownership
- Family members — private conversation with your spouse first (see the three conversations you owe your spouse before signing the LOI), then extended family as appropriate
- Business associates — depends on the specific relationship structure and any contractual obligations
The Honest Self-Check On Whether You Want To Sabotage Your Exit
Here is the direct question worth asking yourself. Ultimately, if you are going to be the person who sabotages the deal — is that really what you want to do?
In some cases, the honest answer is yes. Not consciously — but in your heart of hearts, you do not actually want to sell. In that case, the sabotage may be a delay tactic. Your subconscious is buying time to see whether you could have gotten more, or whether you actually want to keep the business, or whether you need more time to prepare emotionally.
Ask yourself these questions. Have some alternate conversations with yourself. Talk to a therapist or a business consultant. There are normal responses to what you are feeling and what you are doing. Recognizing self-sabotage is not shameful — it is diagnostic. If you actually want to keep the business, do not sell. If you actually want to sell, address the self-sabotage before it becomes a deal-killer.
For related context on why a therapist belongs on your exit team specifically for this work, see why you need a therapist on your exit team.
If you are looking to sell your business in the next zero to thirty-six months, doing at least $2 million a year in revenue with a ten percent profit margin, the deal hotline is 888-DEAL-919. One of the team members will get back to you. No deal is too big.
Related cluster reading: the five times to fire your advisor mid-deal, how to identify key personnel risk before selling your business, why your first buyer isn’t your best buyer.
Frequently Asked Questions
Who is most likely to sabotage your exit from a business?
You are — more often than any other category. The business owner ends up destroying the deal more frequently than attorneys, spouses, employees, or any external saboteur. Not consciously, but through emotional decisions, due diligence fear, and self-sabotage patterns that the multi-month exit process activates. Almost no M&A advisor will tell you this because it implicates the client.
Why do business owners sabotage their own exit deals?
Three primary reasons: emotions (grief, fear, identity crisis after 10-40 years in the business), fear during due diligence (worrying about what the buyer’s team will find), and unconscious resistance to actually leaving. Any one of these can cause bad decisions that damage the deal. All three together produce the highest sabotage risk.
How do emotions cause business owners to sabotage their exit?
You have watched the business grow from nothing to something over decades. You have carried the good and the bad. When exit approaches, you have grief for what you are leaving, fear about what you do next, and an identity question with no easy answer. These emotional loads cause inadvertent bad decisions that torpedo deals.
How can due diligence trigger self-sabotage?
When the buyer’s team starts turning over papers, you begin worrying about what they will find, what they will do with the information, and what you can use to your advantage. Now you have trickery going back and forth. What was a straight-line diligence becomes a chess match. Deals get stopped, held up, or postponed because the fear-driven maneuvering damages trust.
Can attorneys sabotage your business exit?
Yes — when you give them too much power. Some attorneys are killer for the sake of being killer. Winning for them means being aggressive for their own sake, not for yours. They alienate the other side, strong-arm undisputed parts of the deal, and get you locked into or restricted from things you should not need to be locked into or restricted from.
What is the “how many deals a year do you crush?” question?
A direct question worth asking any advisor or attorney before hiring them. They will not tell you honestly. But how they respond reveals plenty. An honest advisor laughs and gives context. A defensive advisor pivots. A dismissive advisor attacks the question. All three responses are diagnostic information about whether they will sabotage your exit or protect it.
What is a saboteur audit and how do you do one?
A saboteur audit is a written list of everyone who could potentially ruin your deal. Categories include yourself, your spouse, adult children, cousins, business associates, employees, vendors, and your attorney. For each, name the specific mechanism of potential sabotage and the mitigation strategy — NDA, structured conversation, distance, or closer engagement. Visibility is required before mitigation is possible.
Who else can sabotage your exit besides you and your attorney?
Spouses through veto behavior. Adult children through family dynamics around inheritance. Extended family through loan or investment demands. Business associates whose income depends on your continued ownership. Key employees who fear the transition. Vendors whose margins depend on you specifically. Even pets and emotional attachments can create resistance patterns that manifest as sabotage.
Should you have pre-exit conversations with vendors and staff?
Yes, depending on the level of the deal. Skipping these conversations frequently comes back to bite you at the wrong moment. Not everyone gets the same conversation — key employees need NDAs first plus continuity commitments, key vendors need NDAs plus relationship-continuity discussions, family needs private timing, and business associates need conversations calibrated to specific contractual obligations.
How do you recognize if you are self-sabotaging your business exit?
Ask yourself the direct question — do I actually want to sell? In some cases the honest answer is no, and the sabotage is a delay tactic your subconscious is running. Talk to a therapist or business consultant. There are normal responses to what you are feeling. Recognizing self-sabotage is diagnostic, not shameful. If you actually want to keep the business, do not sell. If you actually want to sell, address the self-sabotage before it becomes a deal-killer.
Full Transcript
When it comes to selling a business, one of the more eye-opening things is that 8 out of 10, up to 9 out of 10 M&A deals do not close for whatever reason. Why does that matter? Why does it happen? What are some things you need to know about it? This is a fantastic question. I am Scott Sylvan Bell coming to you live from Consulting Secrets on a perfect day to talk about business growth strategies, business exit strategies, and a fantastic day to talk about you.
When it comes to selling your business, the reasons that deals do not close range from numbers, to timeline, to emotions, to trust, to the overall relationship in the acquisition. One of the persons that ultimately becomes a saboteur in your deal will be you. Not always — but a lot of the time. The business owner is the person who ends up destroying the deal.
Emotions really matter a lot, and they get in the way when it comes to business exits. You have been at this business for 10, 20, 30, 40 years, and you have watched it grow from nothing to something. You have watched a lot of good things happen, and you have watched a lot of bad things happen. You are going to have grief. You are going to have fear. You are going to have what do I do next. You may inadvertently make bad decisions and torpedo the deal.
You may torpedo the deal from the other side out of fear, because when they start turning over the papers, there are a lot of different people involved. There is a lot of movement, there is a lot of drama, and there is a lot of conversations. You start to worry about — what are they going to say? What are they going to do? What information are they going to find they were not supposed to find? What can I use to my advantage now that I know they know something? Now you have trickery going back and forth. This can happen at the last minute. It may stop the deal, hold up the deal, or postpone the deal.
There will be times where attorneys destroy your deal because you gave them too much power. They are killer for the sake of being killer. Winning is being killer for their sake, not for yours. They alienate the other side. They alienate other people from the other side, because everybody is afraid of legal proceedings, and some attorneys try to strong-arm parts of the deal and get you locked into things you do not necessarily need to be locked into, or restrict things that you should not necessarily do.
This is why picking your advisors and consultants ahead of time and getting to know them, having prior client conversations, understanding how they do business, their reputation in the industry, and once they get out of your industry — do they have a reputation to uphold, or are they these lunatics that just crash deals for a living? Because if they crash the deal, they can just get paid, and go rinse and repeat. Or they are not really working for you. They are not really working for your exit. That is really important to know. How many deals a year do you crush? Because they are not going to tell you.
Sit down and write out everybody who could potentially end up ruining your deal — your saboteurs. Just about anybody with information about your deal, and even people just on the surface of it. Your spouse. Your kid. Your dog. Your cousin. Your business associate. Your employees. Vendors. Anybody who is going to say — hey, I do not want you to do this deal because it hurts me. It hurts my business. It hurts my income. I do not have the opportunity to make what I would like to make.
You want to have some of these conversations with your vendors, with your staff, and with others before you exit. Explain what is going to happen and when. Depending on the level of the deal, this is very important. Sometimes when it does not happen, it comes back to bite you.
Ultimately, if you are going to be the person that sabotages the deal, is that really what you want to do? In some cases, yes. In some cases, in your heart of hearts, you do not want to sell. Then you may be doing this as a delay tactic. You want to see, could you have gotten more? Ask yourself these questions. Have some alternate conversations with yourself. Talk to a therapist or a business consultant. There are normal responses to what you are feeling and what you are doing.
