Business Development Leadership

When is the right time to ask for business?

As a business coach working with lawyers one of the most common concerns that arises for my clients is the fear of coming across as insincere and in the words of some associates I know: “salesy” or “oily”.

They have a point.

When business development is badly done that is exactly how it can come across.  We have all met sales people and other professionals who have made us feel like some commodity they are trying to get off the shelf.

David Maister has drawn the analogy between our relationships with clients and our relationships with our romantic partners.  In those terms, asking for business right away is like asking someone to get into bed with you on the first date.

I have even heard some business coaches tell their clients to “just get over” their reluctance to ask for business.  I don’t agree.  That reluctance likely stems from your own deeply held values.  It comes from wanting to do the right thing.  The right thing is always to focus on building a trusting relationship first.  The right time to ask for the business will present itself, or in many cases the client will ask you for help.  By starting with a focus on the trusting relationship you will not risk coming across as insincere or salesy. 

How do you start building trust?

Start with listening. 

We naturally trust those people who genuinely listen to us and take the time to understand us.

In David Maister’s post on “Earning trust when there is too little time” he writes:

“The first point I’d make is to ensure that, in the limited few interactions you can afford the time for, you succeed as coming across as sympathetic and understanding. I don’t necessarily want a lot more of my doctor’s time when I see him or her, I just want to be treated a certain way when we are together.”

Listening is the key to coming across as sympathetic and understanding.  As Stephen Covey points out in his book, The Seven Habits of Highly Effective People, use empathetic listening to first seek to understand, then be understood.

To get ready to do your best listening, prepare for meetings with potential clients by thinking about what challenges they might be facing.  Develop a few truly thoughtful and open ended questions that you can ask them during the meeting.  These are questions that will open up the conversation and help you learn more about their interests, background, work, company, and any challenges they are currently facing. 

Engage your curiosity. 

When the person responds, listen attentively, watch their body language, try to keep the analysis in your own head to a dull roar and instead really focus your attention on the other person.  Let them know they have been heard by repeating back a little of what they have told you and then follow with another insightful question.

Insightful questions highlight your intelligence far more than a soliloquy on your experience ever could. 

About the author

Allison Wolf

I am the founder of AWAL and one of the most senior coaches for lawyers in North America. I have helped countless clients over the past fifteen years, develop thriving legal practices and before that served as director of marketing for award-winning law firms. My specialty is uncovering the thinking traps and gaps holding clients back and helping them acquire the mindsets, skills, and habits for growing successful and rewarding legal careers. After a career in legal marketing and business development with law firms in Beijing, New York, and Vancouver, I was trained as a coach in 2004 at Royal Roads University and now coach clients from across North America. You can reach me at or learn more about my coaching practice from the coaching section of the Attorney With A Life Website.