# Resources · Articles

The LOI Is Not the Finish Line: Why Due Diligence Is Where the Real Work Begins

A signed letter of intent feels like the end of the journey. In reality, the heaviest lift of the sale process is still ahead.

Many sellers believe the deal is done once they sign a letter of intent. After months of preparation, marketing and negotiation, a buyer has put a price and terms in writing. It feels like the finish line.

In reality, that is when the real work begins. The letter of intent sets the framework for a deal, but the buyer still has to confirm that the business is what it appears to be. That confirmation is called due diligence, and it is one of the heaviest lifts in the entire sale process.

Where the LOI falls in a sale

A typical sell-side process moves through four phases. The letter of intent arrives at the end of the third. Everything that follows, from due diligence to the definitive purchase agreement to closing, still has to happen before the deal is done.

Phase 1
Information gathering
Set the seller’s goals, review legal, accounting and tax considerations, prepare the company for sale and build the marketing materials.
Phase 2
Initial marketing
Research buyers, distribute a teaser and the confidential information memorandum, collect indications of interest and hold management presentations.
Phase 3
Letters of intent
Answer follow-up questions, solicit and negotiate letters of intent, and select the final buyer.
LOI signed ✓
Phase 4 · The heavy lift
Due diligence and closing
Open the data room, work through the buyer’s due diligence, negotiate and finalize the definitive purchase agreement, make any regulatory filings, and close.

The four phases of a typical sell-side process. A typical timeline runs between six and nine months from start to close.

Nine workstreams, often at the same time

Due diligence is not a single review. It is a set of separate, often overlapping workstreams, each run by a different specialist on the buyer’s side, and each with its own list of questions for the seller.

Legal
Legal structure, material contracts, licenses and permits, regulatory matters, and pending or potential liabilities.
Tax
Income tax filings, state and local taxes, sales and use tax, and confirmation that all liabilities have been paid.
Financial
Historical and projected performance, working capital, quality of earnings and key accounting policies.
Operational
Day-to-day operations, processes and systems, how efficiently the business converts inputs to outputs, and whether it can scale.
Technology
IT infrastructure, cybersecurity, data management, software systems and related risks.
HR and benefits
The employee roster, compensation and benefits, retention of key people, and HR policies and practices.
Insurance
Policies, coverage limits and claims history, including workers’ comp, general liability and property.
Facilities
Real estate and leases, environmental matters, structural condition and required capital expenditures.
Customers
Top customers, contract terms, concentration and attrition risk, and the stability of key relationships.

A Taste of the Request List
Every workstream comes with its own list of documents and questions.
A handful of typical requests shows the level of detail buyers expect. Multiply them across nine workstreams, add follow-up questions on every answer, and the scale of the job becomes clear.
Insurance
Workers’ compensation payroll for the current policy year, by state and class code
HR
A list of employees by title, with wages and years of service
HR
Employee policies and handbooks, including the performance review policy
Customers
The top 10 to 20 customers in each product line, and each one’s percentage of total sales
Facilities
Environmental and structural reports, appraisals and leases

Why it is so hard to do alone

Owners who try to manage due diligence on their own usually discover the same problems.

You still have a company to run
Due diligence lands on top of your day job. If performance slips while you are buried in requests, the buyer will notice, and it can put the price or the deal itself at risk.
The volume is relentless
Several workstreams run in parallel, each with its own deadlines and follow-up questions. Keeping track of what was asked, what was sent and what is still open is a job in itself.
The negotiation isn’t over
Most of what is agreed in a letter of intent is non-binding. What due diligence turns up can reopen the price and terms, and the definitive purchase agreement still has to be negotiated line by line.
It is personal
Having every decision you have made questioned by a stranger is hard. Fatigue and frustration can lead to rushed answers or concessions you would not otherwise make.

A successful sale takes a team

Strategy and execution are an integrated process. A well-run sale brings together several professionals, each with a defined role, and someone has to keep all of them moving in the same direction.

Business owner

  • Evaluates strategic alternatives
  • Helps identify potential buyers
  • Provides due diligence material
  • Leads management presentations
Leads the process
Investment banker

  • Values the business
  • Prepares the buyer list and marketing materials
  • Leads the sale process and negotiations
  • Evaluates proposals
Legal counsel

  • Evaluates the sale process and deal structure
  • Prepares and reviews acquisition documents
  • Handles trust and estate planning
  • Identifies regulatory issues and assists in negotiations
Accountant

  • Examines and refines the transaction structure
  • Identifies tax implications
  • Provides materials for due diligence
Wealth advisor

  • Advises on liquidity and retirement planning
  • Advises on investment alternatives
  • Helps prepare options for minimizing taxes
Others as needed

  • Lender, insurance representative, environmental consultant
  • Provide input on key diligence items
  • Support execution as needed

What an experienced advisor brings

An investment banker’s value in due diligence starts long before the letter of intent is signed.

Preparation before going to market
Legal, accounting and tax issues are reviewed in the first phase, so problems are found and addressed before a buyer finds them.
An organized data room
Documents are gathered and organized ahead of time, so requests can be answered quickly and consistently.
Someone managing the flow
The advisor tracks requests, keeps the timeline moving and coordinates your attorney, accountant and other professionals, so you can keep running the business.
An advocate at the table
When diligence findings come up, an experienced negotiator puts them in context and protects the value you agreed to in the letter of intent.

Start preparing before you need to

The best time to prepare for due diligence is before a buyer is involved. Reviewed or audited financials, organized contracts and leases, a current employee roster and a clear picture of your customer relationships make the process faster and give buyers fewer reasons to revisit the deal.

How we can help

At Windward Advisors, we prepare clients well before they go to market, run the sale process, and manage due diligence from the letter of intent through closing. Through Cornerstone Valuation, we help owners understand what their company is worth before the first buyer asks.

If a sale is on your horizon, even a few years out, a conversation now can make the work after the letter of intent far more manageable.