If your well-trained salespeople are having trouble getting into — then being effective in — the C-suite, you aren’t alone. It’s pretty common. There are a couple main reasons, some of which are easier to correct than others.

I’ve been in the sales performance industry for almost a decade, and have engaged with a lot of sales forces in a lot of industries. I’ve also been an executive, and sold to them; through all of that, I’ve observed a couple of major problems.

Problem 1: The “Salesperson Doesn’t Add Value” Loop

This is a problem wider than just C-suite selling. The sales profession has hurt themselves. CSO Insights published a research note which describes what they call the apathy loop (contact me if you’d like a copy). The basic idea is this:

  • When sellers act unremarkably, customers no longer consult them (currently B2B buyers prefer using company salespeople second to lastout of 10 resources when gathering information…ouch!).
  • Sellers self-inform using one or more of the 8 better information sources and self-diagnose their solution.
  • They then distribute a requirements document and ask sellers for proposals/bids/etc.
  • The request traps most sales teams into a response every bit as undifferentiated and unremarkable as expected in the first place.

Sellers need to add value–go beyond customer expectation– to break out of the apathy loop. Challenger salespeople shake up a customer’s thought process by challenging (hence the name) assumptions and thought processes – generally by “telling”. Insight sellers might ask questions or tell stories. Perspective sellers build credibility, then offer business insights. These insights might take the form of:

  1. Enlarging – or shifting– the customer’s conception of their situation and/or problem.
  2. Altering – ideally expanding — outcomes that a client envisions and desires.
  3. Helping a group improve the quality or efficiency of decision-making. This kind of perspective is useful, but doesn’t move an executive’s needle – today’s topic.

A lot of training programs “yada yada” business acumen:  they tell sales people to “just use yours” and provide perspective. Has everyone in one of your selling roles really achieved a level of business acumen sufficient to provide insights?

It’s pretty hard to provide insights into something you don’t understand.

Some of the best sales forces in the world buy their sales people MBAs. You can build a lot of business acumen into your sales force for a lot less…so why are you choosing none at all?

Problem 2: Executives Only Want to Talk About Executive-Level Topics

Top executives organize their companies. That is, they define and arrange organizational silos, then direct how work flows between them. If an operation or process lives inside a silo, execs don’t generally want to hear about it. Instead, executives summarily push functional-level discussions down into the appropriate silo (and place the offender on their “time-waster list”).

The work of getting executive time is often the work of making your topic relevant to them. While sellers should show the same respect for every persona’s time, the stakes are higher for executive meetings.

Only approach an executive on a topic/issue they will value.

If you don’t have anything, wait until you do. If your people can’t tell the difference, they need more business acumen.

Of course, your training and enablement included techniques and practice for talking to executives (it did, right?).  Now, did you feed them executive-worthy issues…or the business acumen to generate them? Or, did you simply coach your sales people to “get out of your comfort zone.”?  How did you coach actual conversations? Did you get out of your comfort zone in training and enabling them?

Problem 3: Customers Often Buy in Silos.


Another reality: your customer reinforces the apathy loop via their org chart. Silos shape buying processes by simply existing. Companies self-examine their needs through a silo-specific lens. Requirements, RFIs, RFPs, etc. often signal how narrowly your customer is thinking through their own problem. Despite this, the easy – almost automatic — reaction is to follow the customer’s self-limiting thought process.

Remember the customer who called your salesperson in after internally developing their own requirements? Have you explicitly trained your reps to ask:

  • Who had input into the proposal?
  • What other functions and silos were consulted? How heavily was/will their input be weighted?
  • What functions/silos weren’t consulted…and why not?
  • What requirements were proposed, but rejected…and why?

When you haven’t trained and coached reps to ask these questions, they won’t. Your basic sales methodology can work just fine for this, but nobody takes it there. Enable explicit skills, analytics, and tools to apply your methodology across silos to hunt for value gaps…with functions they seldom talk to.  If you don’t, you’re reinforcing avoidance of the unfamiliar…and the apathy loop

If your solution positively impacts more than one customer silo, you need to make sure you uncover every possible ally. Remember, cross-silo benefits are often a valid reason to engage with an executive.

Business acumen provides a foundation for all sellers. Reps need business acumen to talk comfortably about broad business issues across organizations — and function-specific issues “outside of the ordinary”.

Articulating different ways your product or solution could impact functions and roles across a target company requires a different kind of product training. I know of some great tools to help sellers understand the networks of value their product/service can have at a customer. Again, if you can’t articulate an executive-level impact, you won’t have success in the C-suite.

Problem 4: Your Selling Activity is Siloed Too.

Maybe you’re unconsciously reinforcing the apathy loop yourself.  The customer interface is siloed, too. In the past few decades, most B2B companies have exponentially increased the number of roles who “touch the customer”.  Think about it.  We now have:

Sales (hunters), account management (farmers), business development, inside sales, technical sales, demo specialists, sales development (appointment setters), installation, customer success, tech support, customer support, operations, finance, underwriting…

Now ask yourself how many of those roles have been trained and coached to take a few extra seconds to conduct value-uncovering questions, like, “that sounds like a problem”. “What happens in your organization when that happens?”, and “How much does THAT cost you every year?”  Think of all of the silos – potential customer insight-producing vantage points –you’ve engineered into your customer interface, but haven’t taken advantage of.  This one kills me.

Since sales is now a “minority shareholder” within the customer interface, ask yourself why your sales people aren’t able to come up with insights and perspectives worthy of an executive conversation.  If you have team customer interactions, turn it into team selling.  Then structure, train, and coach team selling. Only a few of them need the full-blown sales training and coaching you give to “sales”, but everyone needs a few basics, including basic business acumen.

Think of how this full-spectrum customer interface might close a powerful loop in product training.  Then, imagine the C-suite conversations your salespeople can conduct when theyarticulate the valueyour product/service delivers throughout a customer.

Problem 5: You’re Rewarding Mediocrity

You may have also erected another barrier to your own success: your compensation plan. Do you have a compensation plan and discounting review process that incentivizes sellers to get outside of the apathy loop and discover value? Or, do comp plan and discounting process equally reward both differentiation and commoditization? Humans– buyers and sellers — take the easiest route to an end. If sellers can, they will make discounted sales by sticking inside of the apathy loop: meeting expectations, acting unremarkably and not differentiating themselves or their offer. Ability to manipulate your discounting/price exception system is the only competency required…and is often easier to master than being a great seller.

Sales People Want to Be Great. Let’s Help Them

I am happy to talk about how to help close all of these gaps.  Contact me if you’d like to discuss further. As always, like and share with your networks if you think they might find value.

To your success!

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