When I worked in private practice, and later in-house, there were always things about the way lawyers behaved in relation to contracts that I never quite understood. More importantly, they often made no commercial sense. Perfectly good deals were slowed down by habits, reflex objections and legal ritual that seemed detached from what the client actually needed. Too often, the process felt designed to display caution rather than help the business move forward.
That is one of the reasons I wrote The Sales-Side Lawyer. I wanted to write about contracts not as abstract legal artefacts, but as they are experienced in real businesses, where revenue, margin and speed matter. The book grows out of my own experience in getting contracts over the line.
Part of the problem is how lawyers are trained. We are taught to handle rules, categories and precedent, but often not to think hard enough about the reasons behind them. Why is this clause here? What commercial purpose is it serving? What actual risk is it meant to address? And at what point does legal process stop protecting the client and start obstructing them?
Add to that the profession’s natural risk aversion and you get a legal culture that is deeply herd-like. Lawyers do not like straying far from accepted formulations or market habit because the herd feels safe. If everyone else does it that way, there is protection in numbers. But the herd has its own risks. It produces contracts that are over-engineered, badly communicated and unnecessarily hard to sign.
The fundamental difference between sales-side lawyers and other lawyers is not practice area but behaviour. In the opening section of the book, I describe lawyers by reference to two axes: their willingness to form a view on risk, and their desire to make the transaction happen. Many lawyers are comfortable acting as advisers from a distance, identifying legal issues but resisting judgement calls. A sales-side lawyer is different. They are prepared to make a call on risk and they are willing to get off the sidelines and help close the deal. In a B2B sales-driven business, that is not a stylistic preference; it is a functional necessity.
Sales-side lawyers also understand that they have to wear two hats at once. One is the traditional legal hat: protecting the business and spotting what falls outside acceptable parameters. The other is the commercial hat: helping the deal get done. Those two roles are not in conflict. In well-run businesses, they overlap substantially. The point is not to be reckless. It is to recognise that legal’s job is not merely to identify risk, but to help the business close good contracts quickly and intelligently.
That idea runs through all the main five parts of the book. The first, Sales-Side Lawyer, is about the lawyer behaviour discussed above.
The second, Sales-Side Contracting, is the heart of the book. It focuses on the sales-contracting process: the stretch between a customer deciding in principle to buy and actually signing. That stage is neglected in many businesses, even though it has a direct effect on time to cash, customer goodwill and lost deals. This section is about reducing friction, right-sizing contracts, understanding buyer concerns and making contracts easier to sign without giving away what matters.
The third part, Negotiation, looks at the reality that contract negotiation is rarely just about legal principle. It is about leverage, psychology, trade-offs and fear. Buyers and their advisers are not merely analysing clauses; they are trying to manage internal pressure, avoid blame and reduce uncertainty. If you understand that, you negotiate more effectively.
The fourth part, How Contracts Really Work, pushes back against legal theory in favour of practical reality. Businesses experience contracts through implementation, ambiguity, process failure and scope creep, not through neat doctrinal categories. This section is about how to read contracts properly, use term sheets sensibly, draft proportionately and build agreements that work in practice, not just on paper.
The fifth part, Lawyers, is a more direct look at the profession itself. It asks uncomfortable questions about legal incentives, hourly billing, over-lawyering and the persistent gap between cost and value. Why do lawyers so often import complexity into transactions? Why is ‘good enough’ such a difficult concept for the profession? And why do businesses tolerate legal habits that would be regarded as inefficient in almost any other function? This is not an attack on lawyers. It is an argument for better lawyering: more thoughtful, more commercially aware and more honest about what clients actually need.
If there is one message behind The Sales-Side Lawyer, it is this: contracts should help businesses move. Lawyers should not be the sales prevention department. They should be commercially aware, clear-eyed about risk and willing to think beyond the herd. That is better for deals, better for clients and, ultimately, better for lawyering.
Mark Sherwood-Edwards is the founder of Clearview Legal and the author of The Sales-Side Lawyer, available to buy here.
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