I have been on both sides of the deal. I founded, grew, and sold my own professional services firm, CD Anderson, then led its integration following the acquisition. Later, I managed the sale of an international business unit in Mumbai to a strategic acquirer. Over the past 30 years, I have advised on more than $1 billion in transactions.

Most deal failures are visible from the boardroom well before closing — if the board knows where to look.

Strategy comes before the target

The most dangerous board meeting is the one where an exciting target arrives with no strategic framework to judge it against. Boards should first approve an acquisition thesis: which capabilities, markets or talent we need, and why buying beats building. Every opportunity is then tested against that thesis. At a privately held design firm, I chaired the Strategic Initiatives Committee, that discipline guided the firm through its 2022 sale.

Quality of earnings is an audit-committee question

Headline EBITDA tells you what a seller wants you to see. Directors with financial expertise should probe normalization adjustments, revenue concentration, working-capital targets, backlog quality and how project revenue is recognized. In professional services, one large client or one mis-priced fixed-fee contract can erase the premium you paid.

Integration starts before signing

Selling CD Anderson taught me that integration is not a post-closing project; it is shaped by the promises made during negotiation. Boards should see the integration plan, the retention strategy for key people and the first-100-days priorities before approving the deal. In a people business, the asset walks out the door every night.

Culture risk is real risk

Cultural fit is often dismissed as “soft.” It isn’t. Mismatched compensation models, decision rights and client-service norms can destroy deal value faster than any accounting surprise. Boards should ask how culture was assessed in diligence and who owns it after closing.

Cross-border deals add layers boards underestimate

The Mumbai divesture meant working across regulators, tax regimes, currency exposure and employee protections, each on its own timeline. Boards overseeing international transactions need those risks mapped early, not discovering at closing.

Selling is a governance decision, too

Divestures and ownership transitions deserve the same rigor as acquisitions. Whether the path is a third-party sale, an ESOP or an internal succession, the board’s job is to weigh value, legacy, employees and risk — not simply to default to the highest bid.

The board’s role in one sentence

Management leads the deal.

The board makes sure it is the right deal, at the right price, for the right reasons, with a real plan for the day after. My NACD Directorship Certification reinforced what my deal work taught me long ago: the board’s value in M&A comes from asking the questions no one on the deal team is paid to ask.

What’s the one question you wish your board had asked before its last deal?

ABOUT THE AUTHOR

Cindy Anderson, CPA, NACD.DC, is Founder & CEO of Thinc Strategy, an advisory firm serving owners and executives of engineering, design, construction and technology companies on growth strategy, M&A and ownership succession. She serves as an independent director of a privately held holding company and an outside director of a regional architecture firm, and holds the NACD Directorship Certification and the CERT Certificate in Cybersecurity Oversight from Carnegie Mellon University’s Software Engineering Institute. She has advised on more than $1 billion in transactions over a 30-year career.