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3 Tactics That Are Losing You the Executive Sale
Blog / For Sales Pros / May 11, 2015 / Posted by Ago Cluytens / 4768

3 Tactics That Are Losing You the Executive Sale

When it comes to selling to executives, there’s a lot of well-intended, good advice out there – unfortunately, as the years have passed and buying has evolved, some of it has become more than a little outdated.

There are three things that are still very commonly recommended in sales training, books, blog posts, and videos across the world today – yet simply don’t work when it comes to selling to executives in today’s world.


Over the past decade or so, buying has evolved tremendously – and so have buyers themselves. They are more savvy, informed, critical, demanding, and able to spot nonsense from a mile away than ever before.

How do I know? Simple. I used to be one.

For about a decade of my career, I didn’t sell anything – yet, I did a whole lot of buying. I personally acted as decision-maker or influencer in close to a dozen multimillion dollar deals. As a manager and later on executive for a Fortune 100 financial services firm, I spent thousands of hours in conference rooms listening to someone trying to sell me something.

Tactic #1: Trying to Circumvent the Gatekeeper.

A lot of the well-intended advice that is commonly preached revolves around getting past the gatekeeper. The idea is that, if you were somehow able to get around or bypass the gatekeeper, the executive you are targeting would be accessible, willing to listen to your story, instantly see the value that deliver and consider doing business with you immediately (or at least at some future point).

Bad gatekeeper.

From personal experience, I can tell you this is probably some of the worst advice out there. If you’re trying to get around the gatekeeper – even if you succeed – the only thing you’re building is a reputation as an intrusive, needy seller who uses below-the-belt tactics in order to meet a short-term goal.

Most senior executives have tremendous respect for those who work together closely with them, as executive assistants, business managers, and other trusted advisors. They value their opinion, and frequently and proactively seek it out in order to make decisions about how to spend their time in the best possible way. They often hand-pick these people, and stay with them over the course of a career.

Getting past the gatekeeper is an obsolete idea from a time when life was different – simpler, perhaps. Where corporate hierarchies were still command and control, and the corporate democracy was a far-flung idea. Gatekeepers were generally lightly educated rank-and-file professionals, who saw their primary responsibility as making their boss look important.

In today’s world, hierarchies are flatter than ever before. No one (including senior executives) makes decisions in isolation anymore and employee empowerment is seen by many as a core business strategy – not a buzzword.

When it comes to gatekeepers, seeing them as allies, internal champions and expert professionals worthy of an investment of your time, energy, and resources is probably the best advice I can give you.

A couple of years ago, I started a new business venture. In under three months, I managed to secure a six-figure deal with a large privately held firm that was the undisputed industry leader in their field.  There was no competition, no bidding process, and hardly any negotiation before closing the deal.

How did I get this deal? For about two out of those three months, I built a relationship with the assistant for a pool of project managers (not even an executive). Every once in a while, I shared some useful information, asked for her opinion about how to best further the sale, and got her feedback on some of the key stakeholders inside the firm.

After about eight weeks, she called me asking me to come in for a meeting later that week. Two weeks and two meetings later, the deal was done. Later on, I learned her recommendation was a key factor in inviting us in to speak with their CEO.

Tactic #2: Building a Personal Relationship, First.

Another tactic I hear mentioned a lot is this: focus on building a personal relationship early on. The idea behind this one is that, if you’re able to build an “up close and personal” relationship with a buyer, they’ll trust you – and they’ll trust you with their business.

Know you. Like you. Trust you. Something like that.

The challenge is that an early, budding relationship between a buyer and a seller  is almost never seen in a truly objective light – there’s a lot of baggage lying around. Buyers will almost always assume the seller is out to sell them something (and let’s face it: in most cases, they’re right), and therefore be more guarded than they would normally be in social situations.

In a situation like that, if you’re trying to come off as too personable, buyers will assume it’s a trick to gain their trust – and you’ll end up causing an opposite reaction. Plus, some people are naturally guarded, meaning your tactic will backfire and you’ll be seen as non-genuine and overly friendly.

Here’s what I recommend doing instead: focus on delivering business value early on in the process. Executives value counterparts who are peers, have an opinion, and the intellectual firepower to back it up. They value people who approach them on a basis of equality, and “tell it like it is.”

Over time, delivering business value first will get you the result you seek (building trust), but without the potentially harmful side effects.

Tactic #3: Downplaying the Downside

Nobody’s perfect. And no product or service is, either. Whatever you’re selling, no matter how good you are, there’s always a chance things don’t turn out the way you want them to.

Many buyers have been burned by negative experiences – sellers over-selling and under-delivering. Budgets blown out of proportion. Scopes stretched into eternity. Functionality reduced to a fraction of what was promised.

And, being human just as much as everyone else, that experience tends to linger on and influence their behavior. Over time, the default reaction many buyers have when hearing a seller speak has become: “Where’s the catch ?”

(Kinda reminds me of the old joke: “How do you know a salesperson’s lying ?” Answer: his lips are moving).

Point is, buyers are skeptical of sellers’ claims. Intuitively look for downsides and risk. And often find the holes in your plan faster than you’d have ever imagined.

Some of the most powerful, professional sellers I’ve ever witnessed did something extraordinary: they proactively brought up the risks associated with their product or service – and explained carefully and in great detail how they would mitigate those risks if something went wrong. They immediately gained the buyer’s trust, cementing the relationship and standing out from the pack.

If you’re selling to executives, and you’ve been told to “bypass the gatekeeper,” “build personal relationships,” and “downplay the risks” – there’s only one piece of advice I can give you:

Stop doing those things. Right now.

Instead, start seeing gatekeepers as allies and trusted advisors, and work with them every step of the way. Start every business relationship by delivering value, abundantly, frequently, and early on. Bring up any risks proactively, and with a clear path to mitigating or eliminating. Take it from someone who’s been on both sides of the table: any games being played are painfully obvious, for all to see.

About Author

Ago Cluytens is Practice Director EMEA at RAIN Group, and a recognized global B2B sales thought leader on understanding the buyer's perspective in sales, Insight Selling, and selling to the C-suite.

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