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The Mental Game

Time for some philosophy. Let’s think about the thought process. Consider sales strategy and ponder the Big Picture. If this really is your calling, it warrants some contemplation.

Credit is Overrated

Let’s make a bold prediction. Your sales success is inevitable.

Of course, there will be setbacks and obstacles along the journey. Losses and low points. Huge quotas and ‘problematic’ product offerings. Bad bosses and lousy territory assignments. You’ll have moments when you doubt your abilities and wonder if your decision to pursue a career in sales was the right one. We’ve all been there. It comes with the territory. (I had a regional sales manager throw a phone at me once. Seriously.)

But you’ll also have plenty of great meetings and presentations, successful negotiations and fantastic follow up. You’ll win deals and earn new customer relationships. They’ll pile up, a testament to your abilities and your dedication. Again, it’s inevitable.

When that happens, let others take the credit. Better still, be proactive and effusive with detailed accounts of how your teammates stepped up. Make sure that others, and especially the team that helped bring it in, get the recognition and attention. Advertise their contributions, praise them in public settings and remind senior management of their efforts. Be specific and memorable. “Tony spent countless hours, stayed late all last week to get the Winklebinder file out” or “Have you seen the new demo that Linda put together for InterTechnoCorp? It’s amazing!”

The thing about credit and recognition is that they have a remarkable shelf life when bestowed on others, but go stale almost immediately when self-directed. Imagine soccer great David Beckham celebrating a corner kick goal. Regardless how stunning the achievement, he has seconds to run around in jubilation before it becomes unseemly. Within moments, his coach will have returned to a ‘What can you do for me now?’ attitude. And so should Beckham.

And while your own accomplishments may be Beckham-caliber, the self-congratulatory pronouncements had better be similarly short-lived. But weeks later you can very confidently gush that “Sarah here saved our ass on the StratoComm demo last month! We couldn’t have won it without her.”

Victory is intoxicating, certainly. It’s thrilling to relive the Herculean effort and brilliant execution that you put together to bring in the big win. That’s what selling is about, at least as much as the money. Savor your wins. Appreciate them, of course, and quietly celebrate them.

But credit is a by-product best spread generously around. You don’t need to be quiet about that.

Five Things to Bring to Every Industry Conference

Killing Your Deal

A critical skill for any sales professional is the ability to determine a genuine, qualified sales opportunity from a time sinkhole. Few things are better at derailing a salesperson’s productivity, reputation, compensation and morale than truly fruitless sales efforts. This isn’t about deals above your ability or tough competitive slogs, but specifically about opportunities that won’t close because there isn’t a reason to buy, they can’t or won’t make a decision, or they simply aren’t buying from you. Your job is to be able to identify a genuine, qualified sales opportunity and differentiate it from those that aren’t.

But how? The best way to figure out if you’ve got a deal is this: Try to kill it.

To be specific here, this is not to say you should let your efforts slide, neglect your client, or otherwise practice shoddy sales efforts. And we’re not suggesting that you under- or misrepresent your product/service offering. You still have to deliver 100% throughout the process. Suit up, present your ass off, be your reliably charming self 24 x 7. But part of your showing up requires you to actively challenge your customer to prove that they want and can buy what you’re offering. There is a point, and in a long sales cycle there may be multiple points, where you need the prospect to convince you that they can become a viable, genuine customer.

It’s ‘trying to kill the deal’ because you’re actively scrutinizing whether it is a viable opportunity for you. This is a serious examination of the sales opportunity from the perspective that the potential doesn’t justify the effort. Is this deal worth your company’s time and effort? And is it worth yours?

Here’s the kicker. To do this, you’ll need to engage the customer.

How exactly? Essentially, the customer needs to actively justify their motivation to purchase what you offer. They need to confirm their purchasing intentions and convince you that they’re serious. You’re asking them to make a business case for moving forward.

I was working on a high-profile data warehousing opportunity with a large financial institution, a strategic deal that meant millions in future revenue. And while we had a good technical story and could win in theory, we were the clear underdog to the incumbent, approved-vendor alternative. The sales process had been unusually demanding, with multiple technical presentations, reference calls, and executive meetings. And to that point in the sales cycle, the customer hadn’t made any indication that we had a legitimate shot.

The client then announced that they wanted us to coordinate a site visit with a specific, similarly high-profile customer of ours. The requested visit meant a significant investment for my company, juggling multiple schedules, getting cooperation from our customer (who had to suffer through too many such interruptions already), flights and hotels for several staff. It even required hosting the prospective customer’s team for a dinner the evening prior to the on-site session.

To that point, we had no idea if we were winning or losing and every reason to believe that the deck was stacked against us.

Facing valid internal concern that this wasn’t a deal worth chasing, it became clear that we needed some indication that we were being taken seriously. If not, we needed to back away and accept our losses.

The person who could definitively answer this burning question, and the key decisionmaker for this deal, was a director who’d been instrumental in selecting the incumbent vendor. Gruff, respected and hard to pin down, he was the guy we needed to talk to.

On the premise that we had to discuss details of our upcoming site visit, I was able to arrange a brief one-on-one meeting. After some formalities, I wound up my resolve, enumerated the various steps we were taking and the scrutiny being placed on me to win this deal, and reminded him that he was the company’s executive sponsor to our primary competitor. Then I asked “Respectfully, do we have a legitimate shot here? We’re making a significant investment here and I need to be able to reassure my executives that we aren’t chasing our tails.”

The question seemed to amuse him. He smiled, leaned back in his chair, and said “Honestly, it’s yours to lose.” Almost like a criminal that, finally caught, feels compelled to share every detail of their crime, he then proceeded to explain the situation and the ensuing sales process. That his current vendor had become complacent, that our technology impressed him, that for political reasons he needed to be particularly rigorous in bringing another database technology to support.

Ultimately, we did win the deal as he predicted (or pronounced.) But why did the meeting succeed? Three reasons. First, timing. We had by that point invested enough effort and energy to prove we were a serious option. To have asked the same question early in the process would have shown impatience and arrogance. Second, that it was a one-on-one meeting meant no witnesses. He could keep to his plan knowing that anything I might repeat would be discounted as some rookie sales guy’s optimism. And third, the question was direct and even confrontational, an approach that any self-respecting Wall Street executive would appreciate.

Hopefully, the value of this tactic, however frightening it may seem, is self-evident. Done correctly, you end up knowing with much greater certainty that there is a deal, how to properly forecast it and what level of investment you should make to achieve the win. But the customer gains in equal measure because if it’s a real deal, they should be able to expect better support and access to resources throughout the sales process. Plus, they gain a vendor with better insight into their problems and objectives, one better prepared to craft a tailored and more effective solution.

How you manage this is the challenge, and a lot of it has to do with experience and confidence. After all, nobody wants to intentionally sabotage a perfectly good sales opportunity.

As intimated above, your ability to employ this approach is somewhat dependent on style and geography. In my experience, you can be more direct and even confrontational on Wall Street than on Main Street. In other cases, perhaps the easiest technique to adopt is a Columbo-esque (a 70’s era TV detective) confusion that starts with something like “This doesn’t seem like the right time for you/your company to take this initiative on.” Or “Is your organization really in need of this level of product/investment?”

You can be even more specific, stating something like “This project seems fraught with all sorts of political/financial/ implementation challenges. Is everyone bought in?” Let the prospect explain their reasoning for the deal (if there is one) and leverage your curiosity and ‘confusion’ with follow up questions. The key is to deftly but seriously challenge their reason(s), and compel the client make the case for moving forward.

Another effective approach is to state that “We’re at a point where we need to evaluate and confirm the process so far,” followed by some specific probing questions. Maybe you bring your sales manager along as the bad cop to “evaluate your sales skills and grasp of the client requirements.”

Or bring a senior executive to help, previously coached on the sales objective and armed with specific questions about where things stand from proposal, contracting or timing perspectives. In this scenario, I might let the client in on my executive’s style beforehand and mention that the questions could be direct and even confrontational. In this way, the client is prepared for the worst (which never materializes) and can accurately represent where the deal stands.

If, during the prep call with the client, it becomes clear that the deal isn’t where it should be, there is no longer reason to get my executive involved, and a potential career-limiting disaster has been avoided.

In any case, your approach need not be negative nor condescending. Rather, simply show a genuine curiosity about understanding the problem. Make the statement or ask the question. Then sit back and wait. Don’t sell. And don’t flinch.

Yes, actively trying to kill your deal is a little like jumping out of an airplane. Terrifying. But if the plane is on fire and plummeting downwards, you’ll need to jump eventually. Freeing yourself from a plummeting deal is equally lifesaving.

Get ready to jump.

Paint the Picture

Assumptions can be a dangerous thing.

I recently had a follow up sales call with marketing people at one of the premier health systems in the country. Both individuals were super sharp, knew their stuff and were particularly innovative. I knew this having attended their respective presentations at a conference just a month prior to our web call. In advance of the call, I’d sent along some background material on my company and a couple emails meant to keep us top of mind and reinforce some key points.

Given this particular audience, my strategy was to quickly review the materials previously sent and explain what it was that my company did. Once the stage was set, my thinking was that the conversation would then flow and these two marketing geniuses would ask their probing questions, make some suggestions, and then ultimately land on a potential pilot or experiment of their own clever design.

My assumption was that this particular audience, given their company’s market size and reputation, wouldn’t respond well to being told that they should just sign up for ‘the standard package.’ Instead, I thought it best to keep things conceptual and without specific boundaries for what a relationship might be, given that my company is a tiny start-up and any relationship with these guys would be worth pursuing.

I was wrong.

While the call wasn’t a complete disaster (as I write this, we’re still in active sales mode with them), the conversation floundered. I got meandering questions about our web traffic. They wondered how we engage consumers. I found myself forced to explain esoteric, trivial details about our platform far afield from where I thought any meaningful collaboration might have been headed. Basically, I’d squandered the opportunity. And I’d wasted their time.

The lesson that I had to relearn here was that my assumption was woefully naïve. I’d expected a lively, productive brainstorming session, but what this prospective customer needed were boundaries. And they always do. Customers need a frame of reference. Rather than being constrictive, having one or more defined choices gives the customer a baseline or foundation within which to work.

You need to paint the picture. Provide the vision and show them the way. Maybe your customer will say no, or deviate from the path you’re suggesting, but you’re giving them parameters. Maybe they get creative and want to color outside the lines, but they can only do that if you first give them the lines. Be consultative, of course, but give them choices. Not ‘the sky’s the limit.’

Because, as I just painfully relearned, “We’re proposing that you start with…” is invariably a better sales strategy than “We’re leaving this entirely up to you.”

Five Great Books on Sales (That Aren't Sales Books)

Selling... or Buying?

Here’s something to think about. In one of Seth Godin’s many brilliant blog posts* he talks about how things are either bought or sold. As a business person, it’s important to understand the difference because there’s more to it than marketing and awareness. Being adept at understanding the specific drivers behind buying and selling will considerably enhance the direction and shape of your career, your brand and your expertise.

Notably important to those of us carrying a bag, the compensation is typically different when people are buying from when you’re selling. Things that need to be sold lead to greater compensation than things that get bought. Obviously. If you’re just taking orders or standing behind the register, there may be plenty of marketing at work but probably very little real selling required.

In the opposite extreme, when the item is expensive, complicated, rare or optional, the rewards for getting the sale usually are commensurate with the greater sales effort required.

Why does this matter? For a professional salesperson, the ideal job is at a company where ‘things are bought,’ but the structure, staff and compensation are built with a ‘things are sold’ mindset. In this latter instance, there exists some brief but wonderous window of time when the company and its product have taken off but the compensation plan hasn’t yet had time to catch up. Think relational databases in the 1980’s, SAP and PeopleSoft in the 1990’s and maybe Salesforce in the early 2000’s. It’s great while it lasts but, sadly, it seldom lasts long enough.

Alas, in this hyper-competitive world, those wild but lucrative rides are harder to find, and they run their course more quickly and unpredictably. (In lieu of this, there is the possibility of pre-IPO stock, but divining the potential value and likelihood of a meaningful liquidity event is crystal ball territory.)  

A more reliable career strategy is to find yourself wherever you are and then invest in your development, your skills and your reputation. Because while they say it’s better to be lucky than good, being good is the one thing you can control.

When Winning Isn't

There are deals you shouldn’t win.

Just as there are bad movies, bad restaurants and bad spouses, there are bad customers. Impossible to work with, slow to pay, constantly reorganizing, certain to oversee a failed implementation, untrustworthy, etc., etc. As difficult as it may be to walk away from any sales opportunity, there are definitely situations where you’re better off losing. Or not even competing.

Back when I was selling on Wall Street, I was in the hunt for a big project for a large financial services company. Under normal circumstances, we had a legitimate shot. But the RFP was miserably long and onerous, the customer was belligerent and caustic (even by Wall Street standards), and they had a longstanding reputation for being notoriously slow to pay.

As the customer’s selection process dragged along, we did our own internal evaluation. Did it make sense to jump through the various hoops that the prospects set for us? Not really. Did we see significant additional business coming out of this relationship? Again, not likely, as the company was highly siloed and cross-selling into other divisions would take more of the same tedious effort. Did we enjoy working with their team? And did we trust them? Again, no and no. These answers prompted some serious soul-searching.

Ultimately, we ‘lost’ the deal. At a certain point in their evaluation process, we simply realized that it wasn’t worth the aggravation. We politely withdrew and wished them success. (Wall Street, like most verticals, is surprisingly small and tight-knit. Those on the selection team would inevitably turn up at other firms and be making other purchasing decisions. We calculated that making a deft and graceful exit would be the best potential outcome.)

From both the company’s perspective and my own, it was a tough decision. It’s hard to turn away from potential revenue and the corresponding commission payouts. And we thought that adding a big brand name to our client list would have been a coup. (In retrospect, not so much, as one of their contract restrictions prohibited us from mentioning them in marketing materials or using them as a reference.)

But the benefits from taking ourselves out of the race weren’t insignificant, either. Imagine the wasted time chasing down accounts receivables or dealing with poor references, or the suffering that comes with adversarial contract disputes over tedious tasks you would gladly perform as part of normal customer service.

The vendor evaluation experience is a reliable indicator of the future relationship. Who wants years of that kind of misery? Instead, that time and energy would now be available to invest in better, more valuable relationships and projects. Or playing golf. Plus, in doing so we were able to burden a competitor with a miserable, resource-sucking, perpetually dissatisfied customer.  

It’s never easy to say “no.” Walking away from a deal flies in the face of what the entire sales mentality is supposedly about. But it pays to recognize bad deals and bad customers when you see them. It may not feel like winning at the time, but sometimes the best battle is the one you avoid, and the chance to fight another day.

Top Five Tips for Customer Golf

It's About Triangulation

As any given sales opportunity gets bigger, more strategic or expands across multiple divisions, it inevitably becomes more complicated to manage and more difficult to close. Every new variable brings with it the possibility of more potential, but also greater risk of loss or delay.

Among the potential headaches you should anticipate include:

  • New players and organizations that come into the picture.
  • Different budgets and purchasing rules that come into effect.
  • New legal and contracting constraints that need to be addressed and mitigated.

These added factors make navigating to a successful outcome more difficult. (They also make things more interesting, but that’s a topic for another day.) Fundamental to reaching that successful outcome is an ability to anticipate, respond and guide the sale based on all these new and competing perspectives.

Your ability to step back and think about the deal from the perspective of the various decision makers and influencers, one at a time, is a skill worth developing. Because the particular motivation for one constituent in the deal is often inconsistent with another, even if they’re in the same division or department, you need to weigh and address these different perspectives. To accurately understand and appreciate each person’s purchasing motivations, you need to be able to triangulate.

Triangulation, from a sales standpoint, is the concept of engaging with a broad, informed and influential group of contacts within a given account and then validating amongst them in order to determine the organizational (sales) reality.

The key assumption is that you’ve identified all of the decision makers and influencers in the deal. You also must be actively engaged with them individually and with adequate frequency. Individually because you want direct, candid and critical feedback. Adequate frequency because the sales situation is likely to be even more fluid, biased and fraught with political undercurrents than your run-of-the-mill sale. (Most big, expensive and strategic decisions are. Turf is being challenged, departments are being rewarded or punished, and organization/power structures can pivot significantly on the outcome of these deals.)

When selling to a large bank, I had a respectable license contract set to close during our third quarter. But in the process of doing my usual ‘selling by wandering around,’ a discussion with another division manager found them eager to jump onto the deal. As such software sales go, adding this this new group to the previous deal would decrease the per license price as the total contract value increased. In theory, everyone comes out ahead. So far, so good.

But the larger deal, now involving two different divisions, became a more complicated one for various reasons. Some of the software would be deployed in their foreign branches, which required a new contract review and a rash of edits and more legal work. The product mix wasn’t completely consistent between the two divisions, causing changes to the price schedule. Finally, new approval processes were required that added to the delay, jeopardizing what had now become a December 31 signature under the best of circumstances. (The contract actually became even messier because my company’s various international sales teams learned where many of these licenses were to be deployed and started angling for commission credit.)

To orchestrate all these moving parts required staying in ongoing conversation with the various technical, management and trading groups involved in each of the divisions. One of the takeaways was that it was easier and more insightful to have a quick series of individual conversations than try to coordinate group status calls. More importantly, these one-on-one updates positioned me as a reliable communication channel between these quasi-competitive divisions.

This process enabled me to monitor the pulse of the sale as it dragged its way slowly into December. Despite these complexities, the delay remained manageable and all the deal terms were settled and executive approvals completed with a small cushion to spare. After a complex and protracted sales journey, I was assured that a purchase order for the entire contract could be expected any day.

But the fax machine sat idle and the purchase order didn’t materialize. Instead, I was told there would be a meeting with the vice president of purchasing scheduled for the last week of December. It was a formality, I’d been reassured. This purchasing executive made it a point of meeting the vendors whenever a contract exceeded a certain dollar threshold. I briefed my sales manager and we headed downtown to say hello and wish the VP a happy holiday.

But this VP had other ideas. After brief pleasantries, he explained that the purchase wasn’t approved and wouldn’t be unless we dropped the price by another ten percent. The specific threat was that this deal wasn’t going to happen if we didn’t comply and that they’d go with our direct competitor instead.

So here we are. It’s the last week of the fiscal year with an enormous contract hanging in the balance. I’m stuck in the impressive corner office of some executive issuing a plausible threat, pondering whether to acquiesce to the demand for an additional price cut. (A curious thing about software sales is that every extra dollar is essentially pure profit, so that the whole dynamic of discounting has a weird, theoretical feel to it. Thus, giving in on price isn’t the same when there’s no direct ‘raw material cost of sale.’ Or at least that’s how software salespeople often see the problem.)

Except that we didn’t acquiesce.

Because we knew we didn’t have to. We knew that their engineering teams had already started developing, that the trading desks liked the functionality and that management had already bought off on the proposal.

Most importantly, we knew that they had serious production deadlines that would be jeopardized by a change in software. We even knew that the ten percent shake-down this VP was attempting was trivial compared the cost of any delay. (You can’t fault the guy for trying, though. As is often the case, he was measured and bonused based on how much savings he could squeeze out of vendors like us.)

Instead, I explained that we already negotiated the deal, had assurances from the business heads that the proposal was acceptable and that they were ready to move forward. “We’re sorry, but we can’t help you out here.” What followed was a tense back-and-forth conversation about pricing, other vendors, and rebidding the project. Finally, he wrapped up our meeting with a blunt statement that he wouldn’t be able to approve the deal. That it was effectively dead.

With the full backing of my boss, I chose to hang tough through the negotiation for two reasons: principle and money. Principle because we’d already negotiated in good faith with the senior executives that had the approval authority. I wanted to avoid undermining their reputations if some purchasing functionary bullied us into a different arrangement. And money because that ten percent loss in revenue was all commission overrides. Let’s just say it was significant.

A cloud hung over the rest of the holiday season as I’d effectively traded a deal that would have assured me hitting my quota for one that, theoretically, would have put me into some very attractive accelerators and propelled me into the annual sales club. Now I was looking at neither.

For the waning few days of the quarter I kept in touch with clients while wrapping up the typical year-end purchase orders. I also had now begrudgingly resigned myself to the realization that that my huge strategic win had flatlined.

And it was verifiably dead, until the morning of December 31st, when the fax machine kicked on and that glorious purchase order came through. For the full contract value.

While I’d like to say I knew all along that our take-it-or-leave-it strategy was a winner, mostly I felt like I’d dodged a bullet.

Still, it also felt good to be right. But being right wouldn’t have been possible if I hadn’t been triangulating among everyone involved and knew the situation from every important perspective. And the only way to do that is through lots of conversations with lots of different people and asking lots of different questions. Questions like:

  • What happens if this deal goes through? And if it doesn’t?
  • How is the proposal being received?
  • Where is the funding coming from? Is it one source or many?
  • Who stands to gain (or lose) from this new initiative?
  • What effect is there on staff, territory, status?
  • Does anyone benefit/suffer from this decision (versus a different one, for example)?

Again, every deal is won in the day-to-day execution. It’s in these individual conversations where the selling really takes place, and it’s where your sale will either flourish or die. Skip these conversations and avoid thinking about how everything triangulates among those that have a stake in the outcome at your peril. Break it all down and that’s what makes the whole thing challenging, interesting and rewarding.

And fun.

Five Memorable (and Printable) Sales Management Quotes *

It Should be Fun

Work should be fun. (Say it out loud, like a mantra, to yourself, over and over.) Sales should be satisfying, rewarding and even fun. You should enjoy what you’re doing. You should find satisfaction and challenge in the discipline of sales, in the process, and in working with customers.

Certainly, there are pressures and stress. There are unpleasant clients and moments of frustration. There are failures and setbacks, too. Of course, every job or endeavor carries this risk. But if you’re not enjoying yourself most of the time, you’re probably not doing it right.

To do it right, you need to make the job your own. The job has to be complementary to you and your identity. You need it to fit.

This is both easier and more difficult than it seems. It’s easy in the sense that you simply make the job and how you execute it consistent with who you are.

It’s more difficult because you’re up against the well-established pressure to conform to the culture of whatever your peers, company, management and industry dictate. After all, you can’t be a wild and crazy sales machine in the staid, buttoned-down world of surgical implants or amongst the green eye-shade types in financial services.

Or maybe you can. That’s up to you to figure out. It’s surprising how many wacky, creative, undefinable (and successful) salespeople are able to thrive on their own terms in industries as boring and hidebound as defense contracting or manufacturing.

My corporate sales experience started in telecommunications and financial services before ending up in healthcare, the latter being an industry that might have a near-monopoly on the dry, detailed and mundane. (Spend some time understanding revenue cycle management, patient billing, or clinical trials and you’ll know what I’m talking about.) And yet there are plenty of successful sales professionals who walk (dance, skip, strut?) to the beat of their own unconventional drum.

Admittedly, this takes a measure of courage and self-confidence to pull off. You’re battling conformity and the status quo, so expect resistance. But the rewards, both psychic and financial, are worth the initial discomfort, most of which is imaginary.

And let’s be practical. If this is something you’re going to dedicate yourself to, you might as well make it fun.

Here’s the fascinating part: Your customers want to enjoy their time with you. Most people want to work with interesting people. It’s fun for them. Few things enliven and improve the numbing tedium of the average customer’s day like a refreshing blast of authentic, creative enthusiasm from someone genuinely dedicated to their personal and business success. So be on the lookout for fun.

I’ve been to baseball games and car races with clients, events that are squarely in my wheelhouse. (Maybe my favorite baseball experience was seeing the Durham Bulls play just after the movie came out, and that’s true even having been to the World Series.) But I’ve also been to rodeos and local museums and high school football games with customers, all of which have been great adventures.

During the tail end of one particular sales call in Florida, my customer explained that the space shuttle was launching that afternoon. I responded like a nerdy 5th grader…“Really? That would be cool to see!” To which he said, “Well, let’s go then.” And we did. He even packed sandwiches and beer.

Hit the top restaurants when you travel, or the ones Guy Fiery discovers. When in Baltimore make your customer go duckpin bowling, check out the airplane ‘boneyard’ in Tucson, and visit the Eisenhower Presidential Museum if you find yourself in Kansas City.

You don’t need to show up at the client’s office in a clown suit or sing your voicemail messages, but this job should be fun. Again, if it’s not, you’re not doing it right.

Ease into it. Begin simply. Give thought to who you are, what you stand for (or can stand) and what might be different or out of the ordinary. What would your job look like if it were more like you thought it should be? Armed with that awareness, add whatever ingredients to your selling style that will make it more satisfying, more real and more authentically you.

Trust me. It’ll be fun.

Practice Effortlessness

Just because selling is hard doesn’t mean you have to make it look that way.

Yes, there is a chance that you’ll elicit customer sympathy by being rushed, disorganized and overwhelmed. That’s the world we live in. But it’s just as likely that you’ll be regarded as underpowered, unreliable, unprepared, or otherwise not up to the task. Just because the customer is flustered, behind schedule, dysfunctional, or otherwise in a state of never-ending chaos doesn’t mean they want their vendor partner to be that way.

What your client needs is partners to surround themselves with and align with that make things easier, more enjoyable and more profitable. And that lessen the risk in the bargain.

Part of being one of those select few is to look like you know what you’re doing. And getting your client to see you as capable and professional requires you to make everything look easy.

The first step to be aware. The simple act of examining how you’re going about what you’re doing is the place to start. Notice your pace, your tone of voice, how you carry yourself. Take a breath. Relax. Remember that this job should be fun, or at least satisfying.

Next, make things easy on yourself. That means having tools, resources, people, dates and times, etc. ready when you need them. Plans and strategy can change in the heat of the battle, but having the right tools at your immediate disposal are both confidence-building and enabling. (See page 49.)

If you can draw quickly from an already stocked warehouse of tools, effortlessness takes less effort. If you’ve got a guy back at HQ that can fix a support issue with one phone call, your burden just got lighter. Similarly, knowing someone that’s a wizard with PowerPoint is like gold. Developing that team of people and assemblage of resources takes time. But the payoff is huge for both you and your customers.

Once that’s in place, then you just have to figure out how to make it look like it’s second nature. Image is everything, or at least it counts for a lot. Visualize success. Imagine yourself being smooth and patient. This might seem basic and obvious, or even unnecessary, but it bears consideration. Great athletes play the big game out over and over in their heads before they ever step onto the playing field. In exactly the same way, professional salespeople know how to project themselves as calm, composed and professional.

For the record, effortlessness didn’t come easily for me. I’m something of a ‘scrambler,’ and capable of waiting until the last minute to get things done. To combat that tendency and make things easier on myself, I try to follow up quickly. I aim for more, shorter meetings. And I’m constantly trying squeeze time out of the sales cycle. These practices help take the pressure off and makes it easier for me to seem like I have it all under control.

Because customers expect it. They do not want to engage with someone stiff and robotic, or someone stressed out and disorganized. They expect the person that is you, but an effortless version of you.

Before your sales call, spend a few minutes in mental rehearsal. Walk through how you want the meeting to go. What’s the ideal outcome? What needs to happen to achieve that outcome? How does it feel? Conduct your mental pre-game ritual and see the outcome in your mind before it happens.

Finally, manage your commitments. Be scrupulous when customers ask for things that require tremendous effort. That’s not to say that you shouldn’t volunteer. But be selective and discerning.

Don’t make the mistake of committing to a request for something you shouldn’t commit to. It’s easy to do but worth applying the discipline to seriously evaluate the ask. (See page 123.) I’ve seen countless salespeople (including me, more times than I care to count) promise to follow up on some pointless task brought up by a prospect, usually not even remotely critical to the deal.

Ultimately, it’s all part of the performance. As hard as the job may be at times, don’t make it look that way.

Make it look easy.

About Marketing

Most companies’ marketing departments (with the help of data, AI, and a broad sweep of software and tools) have made great strides at customizing and tailoring the marketing message to better meet the specific interests of each prospective consumer. That trend will no doubt continue, bringing with it a genuine reckoning for many sales professionals as the move towards more self-service further reduces the scope of direct sales. (But that’s a topic for another day, and a different book.)

That said, the effective salesperson will continue to have value so long as marketing efforts can’t fully personalize and inform the buying experience and process as much as prospective customers will demand. (This is another argument to support the old saw that that the weaker your marketing, the stronger your sales effort and/or product need to be.) Which is to say that good sale people aren’t obsolete. Yet.

As important as market awareness and regular prospect contact is, it is unlikely that a new deal will appear in the pipeline thanks to any blog post or ‘blast’ email campaign. An eight-page white paper won’t help a prospective client recognize their need for your solution if they don’t read it. Nor will a generic video with animated stock figures and thought bubbles that rattle off a feature list but gloss over the implementation process required.

A good marketing team will work hand-in-glove with sales to make sure that strategy and tactics are well defined and appropriate for the target audience, providing the air cover to effectively support your sales efforts on the ground. But lately, the collective marketing mindset seems to have morphed to accept the notion that marketing is now ~90% of the sales cycle, with the actual sales team needed only the to wrap up the nasty loose ends. With that perspective, certain problems arise:

  • You reduce direct client input, replaced by feedback collected by marketing efforts.
  • The mentality of ‘more is better,’ and with that a greater pace and volume of messaging and content.
  • The dominance of Google and Facebook, and the insatiable demand for fresh content, drive the priorities. Marketing goals are more focused on engagement and SEO and less aligned with sales goals.


So, what can you do about this?

Mostly, it’s doing what you’re already doing. Ask questions, understand the client’s business, their competitors, and the issues driving their decision process. Then be proactive and generous with what you learn, sharing it marketing team early and often. Basically, you’re helping marketing when you:

  • Collect real-world client case studies – Get clients to explain how they use your product. Good data points include things like implementation time/effort required, ROI/break-even, reduction in turn-around time, increased market share/sales, etc. These can turn into full-blown campaigns, but at a minimum the folks back in HQ are getting real-world insight.
  • Solicit customer feedback How are clients and prospects hearing about your company or product? What do they think? Did they read the last white paper? What did they think of the last webinar? What would they like to see? What are other vendors doing? The insights you gain can help your marketing counterparts craft better tools and events.


As one example, a recent consulting engagement had me working with orthopedic surgeons. The feedback I gathered was that doctors couldn’t dedicate the time to watch a 45 minute video. In response, marketing pivoted by creating short bulleted emails, lightly formatted and incorporating supporting data.

  • Solicit references – Recruit your happy clients to volunteer to talk to the press, and then loop in your marketing team. These are big wins for your marketing brethren, and as the sales pro you’re better positioned to make it happen.
  • Volunteer – Offer to review draft marketing material and content and provide quick feedback. Shag down a client quote. Act as guinea pig for their next campaign. Being active in the process may add to your workload, but it’s the best way to get the marketing support you need when you need it.


You’re ultimately tasked with establishing and nurturing the client relationship, so be aware of what the marketing team is sending out, understand the material and, most importantly, do what you can to make it worthwhile. An unspoken part of the job is to protect the client. After all, they’re your customer. And you’re their advocate, and that responsibility starts before you even meet or speak with them.

Despite focus groups and opt-ins, click-through and web surveys, the customer-sales relationship remains the best, richest and most consistent channel to understand the customer and address their needs.

That’s your channel. Don’t neglect it.

Telling Stories

The Apollo space program is universally regarded as one of man’s great achievements, and simultaneously a marvel of complexity. And yet, those involved with the program at the onset basically simplified the entire endeavor into three key goals:

  1. Send a man to the moon;
  2. Get him back safely to Earth; and
  3. Do it by the end of 1969.


A huge, unimaginably difficult task distilled down to three simple, digestible objectives. Of course, any big, worthwhile endeavor benefits from a simple, well-defined set of objectives. Such a vision works to keep the focus and motivation on the tasks at hand, whether it be beating the Russians to the moon or exceeding your annual sales quota.

That’s a story. It’s a true story, and summarized to the bone, but it makes a point. Stories sell. They draw you, engage you, and paint a picture. And ideally, the pictures you paint help your clients see a brighter, more successful future as a result of selecting your solution.

I actually sat in on a longer version of that story, told by a director at Bell Labs, who used the Apollo program as a roadmap for the important project they had facing them. The details of that meeting remain vivid almost thirty years later, which had to do with the rate of innovation and the impact it had on NASA’s launch strategy. It worked to make their project objective concrete and understandable – and inspiring by virtue of being wrapped up in the mythology of the space program.

Stories sell. Anthropologists and psychologists will tell you that this is because we’re a tribal species accustomed to learning around the campfire or the kitchen table from family, friends or tribal elders. It’s in our culture and our community. Physicians and neuroscientists can more specifically explain that the brain has evolved to encourage and support certain synaptic relationships, that stories and storytelling are hard-coded right into our DNA.

Ultimately, stories sell because they deliver information to us in a format we’re comfortable with and easy to process. They capture our interest because we don’t know where we’re being taken or how things will end. There’s an element of expectation that a good story creates, whether it’s the possibility of learning something new or just seeing that same thing from a fresh angle. (For example, I hadn’t previously appreciated that you could simplify the Apollo space program down to three simple objectives.)

How can you weave stories into your sales repertoire? Consider your style and delivery. What can work authentically for you, and what wouldn’t?  Collect examples from other industries and draw parallels. Read about things outside your industry. You can easily draw from history, and technology folks love a good science reference.

The dogged determination of the intrepid inventor making the earth-shattering discovery after innumerable setbacks is a winner in almost any crowd. But remember to keep it fresh, and ideally even surprising. How Thomas Edison invented the light bulb is now tired ground. (Besides, the guy was an SOB and is more revered than he deserves.) Instead, a story that weaves in Lewis Howard Lattimer, a black inventor who developed the carbon filaments that made the light bulb possible, would be unexpected and thus interesting.

Sports anecdotes are reliable territory, of course, but they quickly become cliché and aren’t meaningful to every audience. But an exception might include a little-known anecdote about the trials and ultimate victory of a local sports team that demonstrates your interest and investment in the client’s community.

A good story shouldn’t feel like a sales pitch. It comes at you obliquely and gracefully. Ideally, it doesn’t have anything directly to do with what you’re selling. And if it’s about you, it pays to be humble and self-deprecating.

A good story should also adhere to a few other guidelines. It shouldn’t preach or lecture, and it should probably steer clear of subjects fraught with dodgy subject matter: sex, drugs, current politics. (You know…all the fun topics.) Clearly, you need to know your audience.

Most importantly, it shouldn’t drag on. To resonate, it needs to keep your audience engaged, so move them efficiently to the big finish.

And a big finish is critical. Your story should have meaning, and should connect them in some way to the shared objectives that you will achieve together.

Finally, telling a good story takes practice, and even a little courage to pull off. Like any skill, being able to tell a compelling, engaging stem-winder that has people waiting eagerly for its ending takes practice. Test it out. Conduct a few auditions. Perhaps practice on your friends or family or at a dinner party before you inflict it on a prospect.

That said, your stories can be about anything. They can be about you, or your dog, or a friend’s bad summer job. They don’t even have to be true.

They just need to be true enough.

The Big Night

One of the more underrated and underused perks that come with a big win is the celebratory dinner. To get to this point, there have been weeks or months of work and tension and probably some confrontation, with lots of players involved and lots of expectations set. After the relief (or resignation) that comes with a signed agreement, you need to change the collective mood. It’s time for a reset.

I propose ‘The Big Night.’ Best executed shortly after the deal is signed, it’s a chance to get the respective customer and vendor teams together for an official congratulations, thank you, and ‘we can’t wait to get started’ dinner.

Oddly, this is a rare event. Customers don’t get to experience an official kick-off or thank you dinner often enough, and this is especially true for the folks in the trenches. A relaxing, celebratory event creates a great initial bond between the organizations that can help keep things on track through any tense and sticky post-signature rocky spot before real progress is visible and momentum is established.

I’ve done a bunch of these and they’ve always been huge fun. One particularly memorable celebratory bash involved a stressful sprint from Boston to New York City to be there. It should have been an easy flight with time to spare, but unpredictable East Coast weather had me switch to Amtrak and a soggy slog through Greenwich Village to make it in time. (Try to hail a cab in a New York City downpour.)

I finally arrived drenched and forty-five minutes late. Fortunately, the evening festivities were just picking up speed. A boisterous and animated evening played out for the next several hours, with too many wine bottles to count, behind-the-scenes stories about the sales process, and photos taken of the ridiculous bill. That dinner would come up in conversations years later with intense fondness. More importantly, it bonded the two groups together and kept the project on track when obstacles inevitably arose.

We’re not talking about pizza in the conference room, but it doesn’t need to be flamboyant. It does need to be meaningful and special. The Big Night should include as many of the right players from both the customer and the vendor side of the initiative as practical. Ideally, you want people from all levels of both companies. And it shouldn’t be about work.

Pick a venue that provides a distraction, but nothing too rustic or you risk losing senior executives. (Orchestrating a chance to have the troops mingle with their senior management is something that scores huge points). A restaurant is probably the best and easiest. Ideally, get a private dining room. Consider group chemistry. If it helps to include a couple extra fun people from either side to make the whole event more engaging, do it.

Plan to say a few words. Do it early, before too much celebrating occurs. You will want to say “Thank you” for being selected, of course, but use the time to recognize individual contributions and effort on both sides.

Stress the team’s excitement at the promise of a successful project and a long and happy relationship. Give your client executive the opportunity to speak, with advanced warning. Then encourage people to meet and mingle and congratulate themselves for a job well done. At that point, step back and let the evening play out. Because you’ve done your part.

Five Things Customers Never Say

Thank You

Thank you for reading this book.

Feels good to hear it, doesn’t it? Who doesn’t enjoy the chance to be recognized for their contribution? And while it’s obvious, I feel compelled to reinforce this most basic social lubricant.

Say “thank you.”

Say it early and often. Make it second nature and genuine. Thank administrative assistants for scheduling appointments, tracking down projectors, getting you a conference room and whatever else it is that they do to make your job easier. Thank your product manager for shifting her staff meeting to be available for that key demonstration. Thank the unappreciated person managing the front desk for, well, whatever.

A simple card with two sentences is all it takes. (See page 61.) Or a Starbucks $5 gift card. (I try to keep a bunch of them in my bag for these opportunities. But cash works, too.) For the unappreciated hotel staffer that gets you the clutch dinner reservation, or the administrative assistant that perfectly handles all the ‘big meeting’ logistics, or for the guy in marketing put the beautiful finishing touches on a key proposal. Say “Thank you.”

It’s common courtesy, of course. But it’s also smart. Nobody gets thanked often enough.

Nobody.