My Notes on Inside Selling #146: Larry Midler on How to Start Conversations With a General Counsel

Throughout my sales career, I’ve had the benefit of selling a range of products, to a range of geographies, into all different vertical markets. And, within each of these markets, I’ve come across different nuances in regard to how to interact with the audience that I am engaging with. Figuring out how to sell into a market most effectively, is part of the reason that selling can be so enjoyable.

It may surprise you to hear, but Sales is more a creative skill than any. Creativity is required to do the things that the others aren’t in order to facilitate a relationship with the target prospect. You won’t stand out if you’re doing the same as everybody else.

Recently, I’ve been targeting legal counsels with an EPA (Expert Process Automation) platform, which presented a good opportunity to learn some new sale skills.

These are my notes on Inside Selling episode #146 with Larry Midler on How to Start a Conversation with General Counsels.


This interview is with Larry Midler who is the General Counsel and Executive VP for CBRE, one of the largest Commercial Real Estate Services companies in the world. A Legal Counsel is essentially the Chief Legal Officer for a business and responsible for all legal affairs within the organisation. Examples could include public company filings, drafting legal documents, managing risk, ensuring compliance and conducting negotiations.

On a typical day as a Legal Counsel, Larry would receive anywhere from 5 – 6 emails a day, to hundreds that don’t make it through the spam filter. Of these emails, Larry will spend a nano second deciding to discard or consider an email proposition.

Mistakes That Sales Executives Make

  1. Pretending to be familiar with a contact when they have never spoken before. This is the quickest way to destroy credibility and ruin a reps chance of getting in the door
  2. Completely missing the mark in terms of the prospect you a trying to target. Whilst Larry is a Legal Counsel, he does not work for a Law Firm. Far too often Larry will receive email propositions that are completely unrelated to the industry that Larry works in. It’s important to do your research
  3. Targeting a General Counsel when in fact they are not the person that the Sales Executive should be speaking with. Whilst Larry may occasionally make a recommendation, it is often best to go straight to the key contact
  4. Persisting when you know you are being ignored. There is probably a reason you are being ignored and that is that they are simply not interested. By pestering, the rep just isn’t getting message and not doing themselves any favours. Think about total addressable market rather than burning leads that you won’t get anywhere with anyway
  5. Telling a prospect what a product does – prospects don’t care what a product does. Think, what can your product do for your prospects’ business
  1. Litigation and how it can be done better/more cost-effectively. This area of the business has always received a large amount of funding
  2. Invoicing technology to automate and process invoices within a business
  3. Cost and budget pressure are always prevalent, so if your product can do something more cost-effectively than a competitor product that can be beneficial
  4. eDiscovery used to be an issue but now there are many services available that utilise AI. Older Law Firms that haven’t adopted the technology yet could benefit. eDiscovery can be risky if not done properly, so seek pain points within their current process

Email Prospecting

The Fastest Path To A Prospects Inbox & Calendar

Reach out to a current customer with an email that says:

‘Hey [name], this is probably going to be a huge imposition, but do you know any [company position] in you network that may be able to benefit from [your product]? If not, no worries, but if so would be happy to send you some text to make it easier.

Do this to 5 people a day, some will at least come back to you. Then, when the prospect you want to reach gets that email, the email will be from someone that the prospect actually knows. Remember, even if you write a good email, you still need to get over the barrier of being a stranger.

Email Copy Example

Short and to the point, writing something like the below can be just as effective as long email copy.

[name], what are you doing to ensure you aren’t (problem) paying for outsourced legal fees. [company] is using us and just saved [value] last [time]. Interesting in learning how they are doing it?

General Sales Tips

  • Use third party proof that the prospect’s competitors might be doing things better than them
  • Address the problem, not what the product can do
  • When writing prospect emails try and personalise to the target prospect. Find out their hobbies, look on Linkedin and make reference
  • Be personal, but don’t pretend to know the prospect
  • Most people who you reach out to aren’t in buy mode, but they are in learning mode. Think of yourself as a teacher and educate your prospects. Send emails teaching a prospect on how to achieve (x) in the form of ‘deposits’. In a few months, you may be able to make a ‘withdrawal’
  • When providing social proof, always reference a company better than the one you are targeting
  • Don’t be afraid of being less corporate, we’re all humans and not robots in a machine
  • If you say you’re going to do something, do it

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