Stephen Gold – The Rainmaking Lawyer: A Short Guide for the Fearful Perfectionist

Stephen Gold – The Rainmaking Lawyer: A Short Guide for the Fearful Perfectionist

Guest post by Stephen Gold.

I make mistakes like the next man. In fact, being – forgive me – rather cleverer than most men, my mistakes tend to be correspondingly huger.

So said Professor Albus Dumbledore in Harry Potter and the Half-Blood Prince.

The law is full of men and women who are cleverer than most. But unlike Dumbledore, they dread being thought of as less than perfect.

Sales is Overcoming Fear

There is a direct link between lawyers’ fear of failure and their general ineptitude at selling themselves. Their client work is arduous. There are difficult problems to solve, deadlines to meet, expectations to manage. But at least they feel most of the time that they know what they’re doing, and are operating on familiar terrain. Clients respect their expertise, and they have a degree of control over events.

Pitching removes that control. Fickle creatures as they are, clients can move potential suppliers up or down their agenda as they see fit, like or dislike them at their whim, accept or reject their proposals for good, bad or no reason. However charismatic and determined a rainmaker one may be, getting a bloody nose from time to time is inevitable. This is not good news for the reserved, risk-averse perfectionist. How best to deal with it?

The root of the issue is confidence, and to firm leaders falls the task of creating a culture in which it blooms.

Company Culture Boosts Confidence

A healthy firm makes it explicit that:

  • Everyone has an obligation to put their heads above the parapet and be involved in winning work, not just doing it. “No time”, “No need”, or “I’m no good at this”, are unacceptable excuses.
  • People who make an exceptional contribution to sales and marketing will receive commensurate recognition and reward.
  • Not winning a piece of work despite one’s best efforts attracts no stigma. Not all sales and marketing efforts will be successful. Where they do not bring a win, they will be learned from and built on to make the firm more compelling next time.
  • On the other hand, not trying will be glowered upon.
  • Billing is not the be-all and end-all. Really. Developing relationships and creating opportunities takes time, much of which will not be chargeable. The firm will grant that time, and also sufficient resources, while expecting them to be thoughtfully spent.
  • On the subject of time, the golden rule is that unless you are very lucky, from spotting the target to hitting it takes at least twice as long as you expect. The firm will understand this, and not pile on unreasonable pressure. It will get behind your efforts.
  • Winning work is a skill of at least equal worth and difficulty to doing it. Accordingly, the firm will invest in training and personal development to help create confident, knowledgeable rainmakers. All are expected to participate.
  • It is inevitable that a lot of activity will be outside normal office hours (whatever they are), and while colleagues are expected to take this on the chin, red eyes are neither a good look, nor a sign of virtue. The firm will support with more than just lip service, the aspiration to have the best work-life balance possible.
  • The firm’s most successful business developers may not be one-eyed megalomaniacs, as is often the case, but have an obligation to mentor colleagues, recognising that a rising tide lifts all boats.

Teams Achieve More Than Lone Strikers

Good leaders can create the culture in which confidence thrives, but ultimately, building it is our personal responsibility. “Wanting to be someone else is a waste of the person you are,” said Marilyn Monroe, and while she might not be the best role model for living a great life, she had a point.

Begin by reminding yourself that you are doing something of real value. People need your skills. You have the ability to make their lives better and more successful. Not everyone can say this.

Do not make the mistake of believing that there is a particular personality type for rainmaking. Successful business developers come in all shapes and sizes. Be thoughtful about playing to your strengths and addressing weaknesses.

Do not even think about trying to do this on your own. Business development is a team sport. Volunteer to be involved. Just as in football, players who are great at providing assists are prized almost as much as strikers. Supporting a team effort successfully is one of the best confidence boosters there is. It provides the chance to observe and learn, and the colleagues you help will want to help you in return. Seek out people who are willing to mentor you and share their wisdom. Not all will (see above, under “one-eyed megalomaniacs”), but they will be there.

Structure & Direction: The Antidotes to Fear

“I have a plan, Baldrick: a plan so cunning it could have been devised by a fox who used to be a Professor of Cunning at Oxford University”. Thus spake Lord Edmund Blackadder. Much good his plans did him. But success is rarely achieved without them. One of the biggest problems in rainmaking is knowing where to start. The market looks huge and amorphous. Where to find the needles in the haystacks?

As the Cheshire Cat said in Alice in Wonderland, “If you don’t know where you’re going, any road will get you there.” 

Finding our direction begins by asking a few basic questions: What markets do I want to be in? Within those markets, who are my ideal clients? How can I stand out from the competition? Bear in mind that the answer to this last question will almost always be more closely related more to the quality of service you give – responsiveness, accessibility, clarity of expression, sector knowledge, connectedness – and your personal likeability, rather than knowledge of the black letter law.

Set up a Plan

Once you have decided, draw up a thoughtful set of objectives, and activities to support them. If you are typical, you will be juggling development activity with the demands of a heavy work schedule, so be forensic about what you’re going to do. As to choosing targets, when I was in practice, I had a crude, but effective formula, which involved asking two questions: On a scale of 1-10, what were the chances of landing this client, and if I succeeded, what was the likely value of the work? The answer would provide a league table of realistic targets worth pursuing. Never forget that there may be more to gain from concentrating on doing more and different work for existing clients, than gunning for new ones. Do colleagues have clients you could serve too, but who currently go elsewhere? Can they get you in the room with them?

Sell the benefits and only later support them with evidence

As to activity, there is no magic formula. The golden rule is to put yourself in the client’s shoes and ask, “If I were them, what would be most likely to appeal?” What are their needs? Why am I the answer? Your activity may involve events, advertising, PR, entertaining and all the rest. But sometimes simple and direct is best. The largest contract my firm ever won, worth many millions, came from a brief letter I wrote to a bank executive saying, “We’ve never met, but here is an idea you may be interested in that I believe will give you an edge on your competitors if you implement it. Can you spare me an hour?”


This is a process of constant trial and error. Be clear about how you will measure success, and willing to adapt. But do not forget the “everything takes twice as long as you expect”. rule. Many a marketing effort has perished because it was given up on too soon.

Finally, practise, practise, practise. It’s the only route to the deep expertise which creates confidence. Practising means you will fall sometimes. But never forget that if your amazing proposal is turned down, nobody dies. Time to reflect, learn, and move on, confidently, to higher ground.


This article was first published here


Stephen was the founder and senior partner of a multi-award winning law firm that became a UK leader in its sectors. Today, he works as a consultant and non-exec with leading law firms throughout the UK and Ireland. You can read testimonials here:

If you would like to link with him, you’ll be very welcome:

Stephen writes regularly on law firm strategy, business development, performance and culture. You can access his article here:

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