#62 Sales Connections: Hire Reps That Fit Your Work Map

glengarryArtboard 1@300x.png

I wonder if I could make a living as a sales trainer?

I spent ten years selling and managing sales forces that blew it out. Twice I helped crank up sales so fast that we IPO’d - reaching combined market values of close to three billion dollars. 

I’d use that experience to sell my services. And once I got your reps in the room, I’d hit them with my inspirational stories from the front lines. 

- Like tracking down a CIO in his parking lot on the last day of the quarter and nailing the big deal. 

- Or the one about the screaming purchasing agent that slammed the phone in my ear three times. But still ended up buying the product at my price. 

- Or the one about the huge company IT director that told me to never set foot on their property again. But eventually became a customer.

I’d blow all this smoke up their rear ends, then I’d teach them the patented Keith Daniel Sales System. It’d be pretty much the same as every other system out there, but I’d have my own buzzwords and cool graphics. 

Everything would be blue - I really like blue.

And your folks would walk out of that training room jacked up. Inspired. Knowing they could take on the world.

Unfortunately, my impact would be short lived. 

In a few months your team would fall back to their old habits. But your lack of sales growth wouldn’t be my fault. I gave you a gold-plated system, you just failed to implement it properly.

Maybe you need another week of training. Cha-ching. Or even advanced training. Double cha-ching.


OK, maybe I’m too cynical to be a sales trainer. It’s just that I’ve endured so much of this stuff and seen such iffy results.

Yes, there’s value. You have to get your reps on the same page and speaking the same language. But unless your team is completely random, a few days of training isn’t going to long term crank up your sales.

For those kind of results you need something extra special. Something that has to be in place before you bother with sales training. And I’m going to share that magical something with you today.


Two things before I share this valuable non-secret. 

Number one, my sales experience is 100% business to business. I’ve sold widgets to manufacturers, and I’ve sold development and database software to techies and CIO’s. The products ranged in per unit price from fractions of a cent to many thousands of dollars. And the transaction sizes ranged from peanuts to millions. On the other hand, I know absolutely nothing about retail or any type of consumer sales. Zero.

Number two caveat before I start - I’m less credible than I’ve let on. Recall in the opening where I tried to suggest that I was a sales god that almost walked on water? I may have forgotten to mention that I’ve also been a massive sales failure. Came within inches of being fired for poor performance and insubordination.

Actually, you already know a little bit about this failing. I touched on it back in post #38 - Please Fire Me. And also in post #60 - Growth With Friends.

In those posts I chalked up my sales success at Powersoft Corporation to great cultural FIT. And I blamed my sales failure at Oracle Corporation on terrible cultural FIT. 

So that's my extra special sales accelerating secret - hire reps that FIT your culture.

Let me explain.


On psychological tests I’m a strong introvert. Way more likely to read a book than chat someone up. 

Yet, I spent several wonderful years of my career in sales and sales management. How’s that possible? Aren't some people born to connect with customers and others aren't? Don’t all successful sales people share a certain personality type?

FITArtboard 1@300x.png

No, they don’t. 

The right personality type for your sales team is the type that FITs YOUR CULTURE. Building a successful sales force is an internal matching game.

I learned this lesson while selling and managing at Powersoft, a company where I FIT and thrived. Here’s an excerpt from my resume that explains my Powersoft responsibilities for a given year…

"Primary objective was to hire and train 40 sales, sales management, and technical personnel and integrate them into a multi-channel sales model."

And I’m not talking about bringing on reps and managers to hawk cell phones down at the Verizon store. We were selling complex software to IT directors, selection committees, purchasing agents, and CIOs. And we were doing it under the pressure of a Wall Street microscope. Our stock price was wildly inflated. If we so much as hiccuped our net worths would vaporize.

So you would assume we hired experienced prototypical sales types with great high level connections in our industry. And you’d be kind of right. At one point we did do that.

And the results SUCKED! 

Those folks collectively didn't fit our culture. And we ended up flushing a million or so dollars on the turnover that resulted from this hiring experiment.

In contrast, the bulk of our sales force hiring fit a much different profile. Here’s another quote from that same resume I referred to above.

"The average sales experience of the incoming sales representatives was less than 6 months and the average sales management experience of the managers was zero months."

It was these inexperienced folks that, in less than four years, carried our team to $50ish million in annual revenue and the company to $133,000,000.

And the non-secret to their success was that they…

FIT our company culture.
Were good at customer interaction.
Had a strong interest in selling our product.

Our process for hiring typically worked like this. We’d hire a technical person that also had an interest in sales. They’d learn our product and spend time in the field assisting customers with product evaluations and troubleshooting. During this time we’d evaluate them for cultural FIT and for customer facing skills. If they did well in both areas we moved them into sales.

And most of them thrived. 

Now, don't miss my point here. It's NOT that sales experience is useless.

That’s 100% not true. 

My point is that internal cultural FIT matters way more than anything else when building a sales team.


Without it, you’ll be dealing with headache after headache. Internal friction. Lack of trust. Deals that don’t quite fit your standards. Finger pointing. Commission battles. You might even go all the way to tears, fights, and lawsuits. And you’re definitely going to see turnover.

That last one is the biggest cost of hiring a salesperson that doesn’t FIT. I recall a small business that tried over several years to build an elite sales and marketing team. But they 100% ignored their culture when hiring. Last I heard they were batting zero for twenty over a multi-year period. They hired and failed with that many folks. Can you imagine the cost in dollars, time, and frustration?


Astute observation. I'm talking about sales success and I haven't once mentioned connecting with customers. Why is that?

Here's why. Below I’ve listed some descriptions of customers your sales folks might need to connect with. Ask yourself if it makes sense to hire specifically to match these customers cultures.

Situation 1: Your customers haven’t done the work to create a strong singular culture. So your points of contact in their organization are culturally random. How do you hire reps to match random culture?

Situation 2: Let's assume the best case, that your customers do have strong corporate personalities. OK, are you going to hire reps that match Customer A’s culture or Customer B’s culture or Customer C’s culture…?

Situation 3: You sell to a single marketplace. For instance, I used to sell to the automakers. And yes, these places had lots of stereotypical car people. So if this was 100% of my customer base I might hire a car loving gal or guy. But, even amongst these companies with closely related products, their cultures were wildly different. Selling to Chrysler versus GM was like being on two different planets. Do I hire a Chrysler type or a GM type? And, another point to ponder. I’m not a stereotypical car guy, and I still sold lots of software into this industry.

Bottom line, I’d strongly suggest that you hire reps that match your own culture.

Reps that FIT, that get what you and your company are all about. These kinds of folks tend to use the pronoun WE not THEY, and customers feel that pride and connection. They want to do business with that kind of company.


All you need to do to implement the Keith Daniel Amazing Sales System That’s Unstoppable and Big League is hire reps that FIT your culture.

But that advice has a huge assumption built into it. It assumes you have a clear, consistent culture for your reps to FIT into.

Which is not true for most businesses. Most owners haven’t done the hard work to nail down their defining principles. Or maybe they’ve written them down but they’re not living them. The principles aren’t being consistently practiced companywide each and every day. 

Which means any money they’re spending on sales recruiting or training is being wasted. 

Don’t be that business owner. Get your culture defined, aligned, and implemented. Then hire sales reps that FIT your culture and get them trained.

Once that’s done, I think you’ll be surprised how much fun sales growth can be. 

That’s all for today. I usually like to close by explaining how everything relates back to my Maps, but I’ve already gone on too long. I’ll have to do that next time.

***Note: This site works best when you read the posts in order. So please head to the ARCHIVE to get started.