How to Get Your Salespeople To Think Like Bootstrappers

Most salespeople don’t hit their target consistently. It’s a sad reality, but it’s the truth. Maybe you’ve got a good company (if you read this blog, you probably do) but statistically, not everybody is a sales superstar. The ones that are superstars are usually proficient Bootstrappers.

Bootstrapping means thinking outside the box and taking action with minimal resources. It means hacking real-life to find new sales angles. When the crowds zig, bootstrappers zag. They’re not wasting valuable time at pointless networking events; they’re thinking of uncharted methods to build relationships with prospects in a way that will close business and smash targets.

A company with a team of resourceful, bootstrapping salespeople will be a profitable company. You could drop off a bootstrapper in any state, in any city, with little to no resources and they’ll make money on day one. Put me in this situation, give me a squeegee and I’ll have my rent covered for the night by sundown. Bootstrapping is all about finding your squeegee.

A Creative Exercise to get Bootstrap Juice Flowing

Ok, that subheading doesn’t sound too attractive, but you get the idea. Before we give a few examples, here’s a great strategy to get your people thinking the right way. Take your salesperson or sales team, sit them down in front of a whiteboard and ask them what strategies they’re currently using. Write down strategies for closing, prospecting and all other sales activities carried out daily.

Now, take your whiteboard marker and cross them all out. Something just happened and these strategies are no longer available. Whatever the reason, they can’t be used any more, but targets still must be met, ideally exceeded. It’s time to get creative. What does your team do next?

Examples of Bootstrapping

Any decent sales team should start presenting some good examples. Remember, it’s not just about thinking outside the box, it’s also about acting outside the box. Don’t be afraid to use the strategies that come up, no matter how outlandish. To give you some ideas of great bootstraps, here are a couple of examples.

Benchpress Sales Superstar

After-hours networking events can be good… if you want to go somewhere for a Jack Daniels and an idle chatter. If you want to close business and secure more clients, they’re probably not the best places to spend your time. Instead, do a little investigative work and find out where your prospective client works out.

Let’s say you discover on LinkedIn that a big account starts every day by hitting XYZ Gym at 5:30 AM. Instead of going out drinking, get an early night, wake up early and spot him while he bench presses. Don’t try to sell him anything. Just focus on building the relationship.

Waiting-Room Health Insurance Sales

Doctor’s waiting rooms might become your new favorite place if you’re a health insurance salesperson. Head down to your local doctors, grab yourself a chair and have your telephone “ring” in your pocket. There’s a client on the phone and he’s keen to hear about your new health insurance plan. Unfortunately, you’re in a packed waiting room, but you need to deliver your sales pitch over the phone right there and then to this eager client.

I guess the people in the waiting room will just have to listen. How many people do you think will speak to you after you’ve delivered your pressure-free sales pitch? That’s right, plenty. And they’re all warm leads coming to you.

It’s all about Getting Creative

We all know thinking outside the box puts us ahead of the pack. Whether you’re using the whiteboard exercise above or you’re actively forcing your salespeople into positions where they must think outside the box to get the job done, this kind of creative thinking is the way to bootstrapping proficiency. I even heard about one salesperson who sold two-way radios that took a part-time job at a hotel for several months to build a relationship with the owner. You better believe he hit his annual target that year…

Don’t let anything stop you. Take your sales figures to new heights and achieve bootstrapping glory of your own. 

In the world of sales, hitting targets consistently is a challenge for many. However, those who excel are often proficient bootstrappers—resourceful individuals who think outside the box and take action with minimal resources. Bootstrappers find new sales angles, bypassing conventional networking events and exploring uncharted methods to build relationships and close deals. Companies with a team of bootstrapping salespeople are likely to be profitable, as these individuals can generate revenue even in unfamiliar territories. Encourage creative thinking among your sales team by challenging them to come up with strategies beyond their usual approaches. Embrace outlandish ideas and act upon them. Examples of bootstrapping include identifying where prospects work out and building relationships in unconventional settings or leveraging waiting rooms to deliver sales pitches to warm leads. By fostering a culture of creative thinking and resourcefulness, you can achieve bootstrapping glory and elevate your sales performance to new heights.