B2B sales: Navigating the prickly patch

Political jostling, ego battles and inconsistency. Start today, change direction tomorrow. Stakeholders shifting and relationships sliding sideways are all signs that you are deeply immersed in the prickly patch, with no way out. 

And let’s not forget, (insert the cackle of a cartoon villain ‘Bahahah!’) … Scope creep! Retreat, retreat!

I am being a tad melodramatic. Yes of course, there are monumental pay-offs when you get through the thorns into the safe inner sanctum of trust when selling into a large organisation. Depending on the scale of the project, this can take many years and a multitude of stakeholders pushing and grinding your solution in from multiple angles.

But wait, ‘Did you hear, the CEO just resigned?!’ Okay back into the patch we march. New relationships and fresh internal players jostling for position. There goes another 12 months, not to mention new competitors to overcome. Game on.

The patch sounds like a ghastly place, doesn’t it?

Well it’s not just a single patch, it’s many minor patches that form to create a large Super-patch. Each patch has a protector, a defender of sorts.  It’s likely the patch protectors rarely communicate with each other, which makes navigating the prickly internal workings of a large corporation challenging. When you do get your deal over the line, there are more potentially skin-ripping experiences on their way, you can bet on that.

I’ve spent the best part of a career selling solutions into large companies, so I’ve learnt a thing or two about how to navigate the prickly patch. Let me be honest, I love it in the patch! Sure, I’ve lost skin over the years, almost lost an eye, but the thrill of walking through the big doors, unarmed and winning business, is exhilarating.

Seven steps for successful B2B selling into large organisations

1. Take your time, be patient. The more dynamic the patch, the more prickly and dense. A short-term approach rarely cuts-through, you need to augment a focused strategy with a long lense. When you’re not pitching or winning business, use this time to acquire new knowledge about the company, competitors, market and stakeholders. Arm yourself with meaningful insights as you slowly cut-through, build cred and a network.

2. Leverage relationships. You wont get far in any patch without relationships, but not just any relationships — valuable relationships with people of genuine influence who can move you through the outer layers into where critical decisions are made and the real game is played.

3. Back the right horse. Towards the upper layers of management the personalities are bigger and often brutal. Your critical influencers must not only survive medium to long term, they need to be equipped to play the game and win. Some will lose, so there goes your channel through. Back the right horses, and over time, they will chart upwards or be promoted and push-through. Empower them, be loyal and they will empower you.

4. Think big, but nothing’s too small. Any opportunity is a good opportunity in the early stages, even if it costs you in some way. To get multiple stakeholders aligned in across various areas of the business, you’ll need to deliver results, not just once, in multiple patches to ensure super-buy-in. This will lead to larger opportunities or projects down stream.  ‘Get your hands dirty’ should form part of your mandate.

5. Don’t buy in before you sell in. Don’t buy into any internal politics; this is not your business. Granted, you have to back the right horses, but you also need to understand how the game is played internally before you can really asset your views or ideas if they go against the grain. Push too hard too soon, and you lose traction.

6. When you get your shot, aim straight and deliver. One false move or failure can bring years of hard work undone. Don’t over-sell, instead keep delivering on your promises. Deliver and keep delivering for your stakeholders. Some stakeholders will go out on a limb for you, so delivering adds value, helps them build cred, which will ultimately serve you. Don’t let them down.

7.  Never get complacent, keep building.  This applies to relationships and your solution. People come and go, business units dissolve and are replaced, and technology evolves, nothing is static. Stay on your toes and always seek intelligence and insights to help you and your stakeholders improve and grow.

Remember, if you fall asleep in the prickly patch you may wake up with a thorn in your ass! This is not pleasant and often hard to remove.

Trent Leyshan is the founder of, BOOM! Sales and author of OUTLAW & The Naked Salesman.