PRO Partners

Engaging LegalTech Decision Makers in the New Business Environment

Peter GillSeven Critical Factors  & Four Underlying Principles

For years CRM systems, sales coaches, pipeline reports have annotated contacts/organisations as ‘Suspects’.  Suspects being turned into ‘Prospects’ is a ratio often reviewed by the Management team with key metrics around how many suspects become prospects, then are taken through the sales pipeline to being a ‘demonstration’, then ‘proposal’ onto ‘negotiation’ and finally ‘closed – won’.

Sales is a process.  There should be a process to identify the people/organisations that are looking for the type of solution your business delivers, so that time, effort, energy, and cost can be spent in the right areas.

So, what happens, from a prospective customer’s point of view, when the would-be vendor makes them really feel that they are the suspect.  And the hunter is after them.  The sales hunter, the one with the knowledge, skills, tenacity, hunger, and desire to take on a sales quota and chase after new business where the company may not have any relationships in place.

Sitting in an enviable position of being both actively involved in growing businesses, through sales of solutions, and being the prospective buyer of products and services, there are countless emails hitting my inbox daily, all vying for attention and seeking to alert me about a product or service that could be of relevance and interest to my businesses. 

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Note and in the spirit of transparency, if I see an approach I like, I borrow from it. No need to reinvent the wheel.  Equally, if I see something which I find hard to believe, I’m cautioned against it and check I haven’t done it, or only done it once and learned from it.

After the couple of years we’ve just had, we’re all coming to terms with the fact that life, business life certainly, will not be the same again.  We can’t turn back the clock prior to March 2020 and carry on in the same way.  

Zoom, MS Teams and similar systems have been our contact tools, replacing the in-office/in-coffee shop meetings with something which at least gave us a face-to-face experience.  Email inboxes have grown with a burgeoning number of emails demanding our time and focus.  Telephone calls and voice mail messages, to prompt a response seem, generally, to have dropped off.

People are busy.  Decision makers and influencers within businesses are busy.  There’s barely a soul you speak to who says they have time for anything.  Action lists are long and often unactioned as they lurch from one Zoom/MS Teams meeting to another.  In some, still limited, cases the decision makers are moving back to real face-to-face meetings, particularly with colleagues as they seek to rebuild connections, business relationships and business culture.

Then there’s the hunter.  With the suspect in their sights, or rather in their CRM and Outlook schedules, as they strive now to win business that was seemingly impossible to win during the lockdown-years.

How have they changed?  What new tactics are they deploying? How are the decision makers and influencers feeling about them?

With the recent experience of an enthusiastic hunter having me in their sights, the feedback from several decision makers within the legal sector and feedback from some great sales leaders & coaches who saw the approach, here are seven critical factors to ‘pause and consider’ when pursuing the decision maker.


1.Creativity.  Decision makers enjoy creativity and people demonstrating it.  In a bid to stand out from the crowd, being creative in a way that fires the imagination is positive as it shows that you’re prepared to try something different to engage the recipient in conversation.  Be creative.  Be respectful.  Try something to fire the overwhelmed decision maker’s imagination.

2. Humour is such a danger zone.  One person’s humorous is another person’s rude!  This feedback came from a large percentage of the people commenting on the hunter’s tactics.  

If the use of humour is designed to reduce the audience size and for the hunter to focus on those that liked the email/image used, by way of then managing those people though the buyer/seller process, it clearly can work. 

Beware that just because a person found the email humorous does not mean to say that they are the prime candidate for your product/solution.  Or vice-versa. Amazingly it splits audiences and creates a lasting impression that may not be the one you wish to create. Sanity check any attempt at humour, particularly in early-stage contact with the decision maker.

3. Frustration is something that must be managed internally and cannot be seen to spill externally, particularly when the vendor is seeking to build rapport with the decision maker. In a post lockdown world this frustration translates through the keypad, onto the email, and into the mind of the decision maker in less than a 2 second read. Yes, they’ll dismiss you in a heartbeat.

Things take time.  If you’re starting the process, the contact strategy, it takes time for the decision maker to respond unless they have an immediate need or are about to assess the market for a solution/product to meet their up-coming need.  Time when they cannot be pushed or cajoled, typically, as they will engage at their pace, not yours. As oft said in the legal space ‘the firms and decision makers within them will move at a pace to suit the partners, not anybody else.’


4. Multiple messages.  Whether it be the product or marketing team setting up the contact activity, or it’s the sales quota carrier building a series of messages to send out to the decision maker over a period, spamming the person with multiple messages in a short period of time is feeling like overkill.  Spam, simply put by most decision makers, will only get you into the trash folder and never to be added to the ‘review when needed’ list.

There are experts in the field that build contact lists, messages to each persona, sequences of messaging to plant seeds and germinate interest.  Marketing has long followed the principles of AIDA (Attention, Interest, Desire & Action) to move a decision maker to the point where they engage with the prospective vendor to discuss requirements.   

That fine line of creating awareness, interest, desire and then action through messaging should not be confused with contacting the decision maker multiple times with generic messaging, which has the opposite effect as they sift through the hundreds of emails received every day.

5. Marketing-speak.  This hit a nerve.  The use of what is seen as generic marketing speak, with terms of reference that look good on a website or on marketing collateral, but you would never ordinarily say in any kind of business discussion are a red flag. 

It might read like the greatest email, or series of emails ever, but your audience, typically has seen it all before.  Your audience is human, so communicate with them as a human.  Your product/solution may be able take them to the moon and back and make them the highest-flying firm in the stratosphere, your decision maker will typically want to know that it can do something more based on worldly aspirations.  

Stop the Partners getting frustrated, picking up the phone and bemoaning to their EA’s, management team and IT team that they have to use 7 clicks to send something to a client?  Great.  Make their iced latte with a cinnamon twist because it did that for their major competitor? No thanks.  Get real is the feedback from decision makers.

6. Authenticity.  Not always easy, unless face-to-face, however but it’s better to try to be authentic rather than be yet another vendor with another great marketing team pushing generic emails out from Mail Chimp (or others) to be consigned to the ‘lazy sales technique’ pile.  

Being authentic is easier face-to-face, however, the hunter salesperson has to get to that stage and the approach has to enable the decision maker to feel that there’s a connection through the contact and initial stages of getting to know each other.  

Being human, with personality and warmth, is often seen as more persuasive than ‘pitch-perfect’.

7. Providing insights is powerful, when done with authenticity and without overloading the decision maker with marketing-speak.  

The business behind the sales hunter can do the research, provide great insights, and share the company message.  Getting these insights onto the sight lines of the decision maker is important as insights are only insights if the decision maker reads them.  Feedback from decision makers engaging in review processes is that they are aware of generic insights from leading consultancies/advisories.  Bringing them more specific, relevant insights, based on ‘local’ experience is compelling.

Have considered these seven critical factors, there are also four underlying principles that will help the salesperson stand out when the decision maker is moved to action.  

  1. Empathy – to build a relationship you need to demonstrate empathy with the decision makers position, to ask the questions that help them to open up about the situation they/the business is in and feel that you’re interested and informed enough to understand it
  2. Building trust – decision makers will seek you out to work with you if they trust you.  Careers can be built and conversely disrupted, based on the selection of solutions/products.  The decision maker has to be able to trust the supplying company and the person they’re reviewing requirements with; the salesperson and the team they bring to the process
  3. Long-term view – the simple fact is that if a decision maker has made an alternative decision, or is in a contract cycle, doesn’t have the bandwidth/budget or a whole host of factors, then they are not buying from you at this time.  Sales quota’s often create short-term thinking but managed properly (back to metrics and understanding your own ratios for success) then a long-term view can be taken.  Some of the best, most successful salespeople have taken a long-term view to ensure they create deals now and, in the future, when everyone else has burned their bridges
  4. Trusted advisor – aligned to building trust in the buying/sales cycle, becoming the person that the decision maker trusts means that the salesperson can adopt an advisory position; even if that means advising on taking another vendors solution/product because it’s the right thing to do

There are many great companies out there, promoting their solutions/products and enabling their sales teams to engage in conversations with decision makers about their business, the challenges they face and how they can benefit from working collaboratively with the team of interested, helpful and supportive people from their company.

Even at the simplest solution/product level, those responsible for buying them often want engagement.  A relationship of sorts.  To feel a connection.

There are several great books that are designed to help the sales ‘student’ in improving their skills.  Far too many to mention, though The Chimp Paradox (Prof Steve Peters) and Conversations That Win the Complex Sale (Erik Peterson & Tim Riesterer) are great books to read and re-read.

Coaches provide great advice and in many organisations there’s a budget for investment in skills development, using external coaches to bring their own experience and expertise to the party.  You never stop learning and the best always want to be better – take any example of a person at the top of their game, particularly in sport, and you’ll find a person open to learning, applying the basics day-in, day-out and being coached.  

As a person sitting in both camps i.e. the decision maker/influencer when buying solutions/products and the business owner seeking to grow revenues through sales, it’s great to be able to learn from others.  We’re all human, we all make mistakes, and we should always keep trying different strategies and approaches.

For the hunter stalking the suspect, maybe it’s time to realign thinking (even if the sales quota demands deals every month) to putting the decision makers’ shoes on for a while.  Consider how, with empathy and authenticity, to understand their situation, work to their time frame, provide relevant insights, though ditching the marketing-speak and being human.  

As they start the ‘dance’ of their buying process, align the sales process to it and be there, creating a relationship of trust where you can become a trusted advisor when they need support.  Be the disruptor, challenge thinking when it’s necessary, show them how your business can be the best business partner because you’ll do what it takes.  

Then you’ll have buyers wanting to use your solution/product and being your biggest advocate.  In time, because it takes time.

Peter is the co-founder & Director of Business Information Group Ltd and the Commercial Director of VirtualSignature, a rapidly expanding SaaS based business enabling firms to digitally sign & exchange documents, verify identity & onboard clients securely.

He has been leading sales and business development in the legal, accountancy and professional service sectors for a number of years having previously operated at senior leadership level with businesses including Thomson Reuters Elite, One Advanced, Wolters Kluwer and LexisNexis.

Engaging with key stakeholders he has grown business revenues in UK and internationally. His remit has also been as a buyer of services, working with providers to ensure the alignment of requirements and their services.

As such, Peter sees both side of the coin; the drive for sales revenues and the customer buying experience.

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