Authenticity Matters

When selling to legal teams, it is both saddening and surprising that these mistakes are made time, and time again in legaltech.

Selling, including selling to legal, is about building and maintaining relationships not one night stands. Being authentic goes a long way, both in the short and long term. All the more so when selling to legal where concerns of trust, confidentiality, ethics and generally being a “safe pair of hands” matter above all else.

This isn’t reality television, faking it means you won’t make it when it comes to selling legal teams legaltech. In legal enterprise software sales buyers want partners, not peddlers.

Three ways to nuke your sale

Steer clear of these three basic, but overlooked mistakes when selling legaltech.

1. Lying

Never. Ever. Lie.

This should go without saying. Sadly, too often this childhood lesson is often totally forgotten when it comes to pitching legaltech. It’s at its worst when that legaltech embodies some form of “AI” or “blockchain”.

Regrettably, some legal AI vendors are essentially Wizard of Ozing, using humans behind an interface to present an impression of next-generation contract review.

This is also known as fauxtomation, and is a topic we’ve highlighted here and here.

The worst part is these tools might genuinely be valuable if they were re-framed as LPO offerings, backed up by the necessary SLAs and other protections of an LPO.

Instead, pretending AI where none in fact exists simply means no sale… and a very tenuous market reputation. Better vendors are upfront and open about whether, when and how they use humans in the loop. Be a good vendor, please.

“We use true quantum machine learning AI blockchain that learns by itself”

Oh, and this goes for demos… often the greatest source of misinformation or downright fakery. Don’t do this, instead do this.

Don’t take our word for it. Remember the obvious fact legal teams are trained to detect BS. Sooner or later you’ll get caught out.

Therefore, in all interactions be confident, but don’t fake it until you make it. If you fake it, you won’t make it.

2. Bamboozle

Similar to the above, don’t attempt to mesmerise buyers with the latest buzzwords and technical mumbo jumbo.

Doing so will typically:

  1. Inflate expectations, on the assumption the jargon sounds clever, must be clever and therefore will be exceptional beyond all basis in reality.
  2. Turn people off, on the assumption they cannot understand what you are saying and either (a) feel dumb, or (b) genuinely can’t find a fit for your product vs. their need.
  3. Suggest that your product is fake, or based on BS marketing.

Keep it practical and grounded. The tech is often irrelevant so long as you can demonstrate scalable value. Focus on the ends and not the means.

3. Sneaky

Buyers invest huge amounts of time and energy gathering user requirements, surveying the market, meeting and vetting vendors and products.

The surest way to mess this up is to go behind the buyer’s back and pitch to other individuals within the organisation.

Inevitably the pitched other does one of two things:

  1. contacts the buyer straight away, adding yet another management overhead to the buyer’s list of stakeholders that need to be placated; or
  2. contacts the buyer weeks or months later, by which time said other has signed or hopes to sign a contract without having gone through the proper approvals and thereby created an expectations management timebomb… sometimes coupled with an expectation the product can also be deployed instantaneously into the organisation’s IT environment for a live matter… which is rarely, if ever, possible due to security and procurement reasons.

In either scenario, you make the buyer’s job harder not easier. And it never ever ends well for the vendor.

The only sure thing is that the vendor will end up on the naughty list, never to be contacted again.

Something to do instead – be honest, humble and hopeful

Overinflated expectations have a compound effect.

Over time mismanaged expectations exponentially inflate beyond an inflection point. After that point, no matter what you deliver, no matter how good it is, it simply won’t suffice. Once the genie is out of the bottle it’s impossible to put back.

This is when the buyer’s remorse, or cold feet, kick in.

Too often expectations are set into the stratosphere only to come crashing down once a sales cycle moves from pitch to proof of value, let alone from proof of value to production (if it gets that far). But there is a solution.

Underpromise and overdeliver is a winner

To avoid compounding overinflated expectations do what most business and career development books prescribe:

Underpromise and overdeliver.

Yes, this idea has its supporters and detractors. Yes, naturally, if used too often, this can become somewhat phony and disingenuous. But used well, this can deliver dividends in terms of relationship building, stickiness and trust.

If anything, it’s a useful yardstick to check yourself: is what you are promising the buyer overstretching what you can deliver? If so, rein it in, don’t promise it and certainly don’t hype it.

It’s also true that buyers get easily distracted by FOMO and Shiny Object Syndrome, falling madly in love with the solution and not the problem. Help them stay on track by coming back to their problem will help avoid a deathspin of hype. You can do this by focusing on the ends not the means and tackling the real issues they face vs. the supposed benefits of something that is simply “new”.

Selling to legal should be about what you can do, and not what you know you can’t do.

We know you have competitors, so should you

Be humble. You may be the best of breed in your niche but acknowledge your competition. Very rarely, if ever, is a single product or service without competition. If not, it’s usually anti-competitive and therefore not something a legal organisation can buy. Claiming to have no competitors comes across as arrogant, oily or just plain dumb.

Legaltech is an increasingly crowded market in need of consolidation – do buyers a favour and respect their intelligence!

However, don’t disparage your competition. One or two legaltech vendors seem to delight in publicly denigrating their competition, via thinly veiled attacks at easily identifiable vendor proxies. No one likes a bully. Don’t be one.

Smeagol Gollum

Instead sell your strengths, not the weaknesses of others. Describe the differentiating factors or features of your product. This might be your delivery and subject matter expertise.

Mention, to the extent you are legally entitled, other organisations working with your solution and why they’ve done so. If you can, provide data-backed ROI studies of such successes – this is extremely rare, and doing so will make you stand out vs. the competition.

Bonus point: when selling to legal it goes a long way if you can provide referenceable legal teams, not simply a slide with a competitor’s logo.

Help make buyers look good

Selling to legal should make the buyer look good. Anything you do to make the buyer look dumb, or worse, bad at their job will ultimately come back around and ruin your chances of concluding a successful sale or profitable longstanding sales relationship with the buying organisation.

Easy ways to make them look good are to come armed to presentations, pitches and demos (or better still proposals) with demonstrable ROI use cases based on disclosed assumptions, qualifications and context. Have pre-baked materials the buyer can review and share to sell you internally. If adoption is a challenge (it always is), how can you share the load and ease this painpoint? If your product is cloud-based but the users cloud wary, how are you building consensus with the legal buyers and their clients that need to bless the use of your solution before the necessary network effect can be established for its use? Likewise, if you can help the buyer prove ROI against their own use cases with ease then it becomes very easy to buy and much less effort to sell.

Getting to know the buyer identities, their needs and those of their above and below stakeholders can also go a long way, especially if it helps identify how to make the buyer look good.


Whilst it can be appealing to take shortcuts… DON’T. People buy based on people.

Trust over trickery wins over the long term.

Be upfront about your product or service, what it can do / can’t do and what is today vs. roadmap of tomorrow. If you could do something beyond current capabilities, be realistic with yourself and the buyer about the qualifications and assumptions delivering on that promise might entail.

Acknowledge competitors but don’t disparage them.

Sell to your strengths rather than crow about the weaknesses of others. Confidence is attractive, whereas negativity is not.

But in the end, be realistic but hopeful about the value you can provide as a partner, not peddler.

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