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Stretch. Raise your game. Add a new tool to your bag, and a new weapon to your arsenal.

Compressing Time

Stretch. Raise your game. Add a new tool to your bag, and a new weapon to your arsenal.

If you were to imagine the arc of a complex sales process, from the identification (or even better, the creation) of buyer interest to the point where a purchasing decision is finally made, there are any number of events (or client touches) along that arc where something happens.

There is a meeting, or some follow up, or a proposal, etc. There are mandatory events, like an initial client encounter or a purchasing decision (which might be to choose a competitor or not purchase at all.) There might be unanticipated events, such as a meeting cancellation or an objection. Or there could be other client touches intended to help position you or gather additional information.

Managing the Sales Process

Whatever those sales events happen to be, the sum of them delineate the many moments and events along that particular sales cycle. Some sales cycles have more events, others fewer. But the set of events for a given deal accomplished over time define that sales cycle.

Now imagine what would happen if you decreased the time it takes to get from start to finish for every sales opportunity over the course of a year by, say, 20%. How would that impact client satisfaction, your close rate, and ultimately your income?

A good sales executive does exactly that. He or she compresses time. It’s not about eliminating steps or trying to take shortcuts. (In fact, a good salesperson will deftly add touches and events throughout the arc of the deal.) But it is about ways to make things happen more quickly, with less elapsed time. Simply put, your job is to compress that arc and shorten the time span between “Hello” and “Let’s get started.” Or otherwise, get more quickly to “No thank you.” (See Killing Your Deal.)

Despite the likely obviousness of this statement, it’s rarely followed with the zeal and attention it warrants. Contrary to what you may have been told, good things don’t come to those who wait. Time is your enemy. Time kills deals. Delay seldom works to a salesperson’s advantage.

Finding Ways to Shorten the Sales Cycle

A fundamental tenet of your sales philosophy should be to continually find ways to shorten the time span between each step along the sales process. Think about how to respond at

least a little bit faster than expected. Cut an hour, a day or even a week out of the time between stimulus and response, between when something is promised and when it’s delivered. Every time you can shorten the time span between touches works to advance your deal to the next step and move things forward.

Compressing time as a fundamental sales practice accomplishes other objectives:

  • It identifies you as responsive and effective,
  • It gives your customer a sense of confidence in you as a business partner,
  • And it can help to set the pace of the process, and thus forces your competitors to keep up. By keeping things moving, you’re effectively positioning your competition as less responsive and less customer service-oriented.

This momentum works because an immediate B+ response is almost always better than an A- effort that doesn’t happen until weeks later. And it stands to reason that you can craft a better response immediately, when it’s still compelling and the details are fresh in your mind. (Besides, a thorough follow up reply, email or otherwise, can double as your sales notes.)

If necessary, send an early version of whatever deliverable you’re working on stamped with DRAFT all over it, or with highlighted questions soliciting client feedback, drawing from your sales toolkit of prepared resources.

Establishing Your Sales Advantage

By adopting a commitment to compressing time, you gain the added advantage of staying sharp and in control. You’ve established an active, customer-centric momentum that helps propel the process forward. You’re driving the sale rather than watching from the backseat.

Note that consistent efforts to compress time will often result in another client behavior. Customers certainly appreciate a timely response, but they can also start to expect it. So be prepared to sustain this practice. Getting things ahead of schedule, without having to ask or send reminders, allows your client to respond more quickly internally, look good with their peers, and generally appear to have their project(s) under control.

Admittedly, this tactic is simple (and obvious.) Respond quickly to emails, questions, or requests for additional information. Sales call follow up should be crisp and timely. Get the next step discussed and the next meeting scheduled as a normal course of the current conversation.

It’s the mindset that requires effort. It demands that you make an attitudinal shift, adopting a sense of customer urgency that enables you to think about how you can compress time. Once your attitude is where it needs to be, you’ll need to combine that with tools and processes to make time compression possible. (See Your Sales Toolkit.)

Now, squeeze.

Admin Assistance

Early and frequent contact with key executive contacts is instrumental to any salesperson’s immediate and long-term effectiveness. It is your best, most efficient chance to monitor the pulse of company objectives, organizational changes, and all the other inevitable and frustratingly unimaginative dysfunctions conspiring to ruin your year.

And who else is just as busy monitoring that pulse?

The administrative assistant. He or she (statistically speaking, executive office assistants tend to be female, so we’re going with one pronoun here) is squarely situated at the confluence of rumor, reorg, purchasing and various other news streams. And more importantly, she manages your key executive’s schedule, availability and attention span. Having her ear is a good path towards a closer relationship with her boss. So, you need to nurture that relationship.

Build Relationships Everywhere

Start by understanding that they aren’t secretaries making copies and fetching coffee. A good executive assistant makes a sizable (if unappreciated) contribution to the company’s accomplishments. And they can be invaluable to your success.

They’re dialed into organizational changes, corporate edicts, and all sorts of valuable insights. I’ve had admins juggle appointments, hand me company directories, let me know exactly when their boss can take a five-minute call, tell me of upcoming birthdays, and give me the play-by-play on ridiculous office dramas. They’ll email you org charts and explain why so-and-so in purchasing is a @#%!. And then they’ll share advice on how to navigate around that person. You underestimate their influence at your peril.

Nurturing that relationship doesn’t have to be difficult. Mostly, it’s just common sense. For example:

  • Keep the admin informed – Just like anyone, the admin wants to be viewed as smart, informed and capable. Make part of the conversation about the industry, about what’s happening elsewhere in the company, or other detail.
  • Pass along news – Use some important event or milestone as an opportunity to keep the executive informed, but do it through the admin. A short note or quick phone call explaining how “Sandy might find this of interest because…” has huge karmic value.
  • Solicit feedback and opinion – “We’re wrapping up our proposal and I wanted to ask you how…” or “What’s going on over in marketing?” can be the catalyst for a priceless twenty-minute conversation on the company.
  • Be brief – Ask for less time and let the admin be the miracle worker. Time is a valuable and misused commodity, so ask for thirty minutes (or ten) instead of an hour and let her show off her ability to juggle schedules. Then keep to it.
  • Make things easy – The executive assistant is dealing with complex schedules and lots of loose ends, so come prepared with the solution. Make the job easier. Send along a draft agenda, email the appointment invitation, set up the conf call #, look up the driving directions to the restaurant or golf course, etc.
  • Be profuse with appreciation – Quick follow up notes, updates and thank you’s are mandatory follow up. Plus, you’re front of mind it’s time to ask for that executive’s time and attention.

Invest in the administrative assistant and benefits accrue. You gain a valuable ally inside the company. You learn important details that will inform your strategy. And you get greater access to the executives that matter, when it matters.

Your Secret Sales Weapon

In one especially notable instance, I had been trying to hastily arrange a presentation with several key prospects but couldn’t get the calendars to sync up. The executive administrator, with whom I’d known for some time and with whom I thought I had a good relationship, seemed unable to find an hour that would work that wasn’t over a month out. Given the one-on-one communications I’d been having with the directors needed for the meeting, the delay was hard to understand.

Until the reorg, that is. It turned out that the administrator was slow-walking the process but couldn’t tell me about the impending changes to the reporting structure. But her savvy saved me a bunch of wasted effort and the possibility of a lost deal.

Treat admins with the same respect, interest and preparation you would any other prospect. Talk to them rather than through them. Be respectful of their time. Be professional, but friendly. Smother them in thank you’s. Treat them like the executive they report to, as though they are a key relationship in your overall sales strategy.

Because they are.

Companies ≠

Just as you wouldn’t confuse your job with your career, don’t confuse companies and customers. You might have a list of companies that make up your territory, but it is always the people at these companies that buy. Here’s the simple math:


                    Companies ≠ People

Customers = People


Over the course of your rich and varied sales career, you will likely have the good fortune to meet and get to know an overwhelming number of prospects, partners and customers. Chances are that some of them will turn into great long-term friendships and hopefully most have the promise to become future working relationships. Regardless, they will inevitably bounce around among companies and industries over the years. They might get promoted or need a recommendation. Or they may go work for one of your competitors. Or perhaps provide you with a recommendation or a reference. Anything is possible.


You Don’t Sell To Companies

It’s easy to fixate on the company as ‘the customer.’ For most of us in sales, the company is the defining entity, part (or all) of one’s sales territory, and ultimately the target, after all. It makes sense to equate someone in the company as the company, but it’s not that simple. People get recruited, fired, move, get fed up and quit. Even a CEO, the face of the company, can go somewhere else. (Some of them can be odd, narcissistic and even sociopathic, but even sociopaths are people. Right?)

This also means that there’s an excellent chance you’ll run into these people throughout the arc of your career. Personally, I’ve been hired by past customers, and I’ve frequently been referred to other customers by past customers. I’ve even had a customer invest in my business.

In one memorable example, I found myself in the midst of an especially heated, contentious negotiation on what was one of the largest and most strategic deals of my career. I’d developed several solid relationships in the account, and in partnership with one fellow in particular had devised the framework for an exclusive customer/vendor affiliation. The proposed deal promised to dramatically increase our revenues, strategically position us with one of the largest health plans in the country and deal a significant blow to several competitors. All at once. And after a series of meetings, presentations and proposals, both sides agreed that this new, bigger relationship made sense and that a deal should be hammered out.

As the negotiations played out and we worked through the myriad details, my primary counterpart became increasingly adversarial and ultimately opposed to the deal terms. But the executive team above him wanted this done, and over the ensuing weeks he was sidelined unceremoniously from the negotiations. In the process, the friendly relationship we had established over the years became frayed and he ultimately left the company.


A Happier Sales Ending

The story could easily end right there. Instead, we ran into each other awkwardly years later at an industry conference. Eventually, the conversation steered itself to that deal and our falling out. I ended up getting a much better perspective of the internal politics that he was enduring at the time and the implications of the deal. That chance interaction was the catalyst to reestablish our relationship, and he has since become one of my closest business friendships, something that would have been impossible to predict as I was consumed with one of the largest deals of my career.

In your daily sales efforts, keep in mind that your customers are people that go home to screaming kids and obligatory soccer games, have cats to feed, need to mow the lawn, have debts and ailing parents, and are hooked on Game of Thrones. So maybe it’s not about you. Maybe it’s the company culture that best explains their actions. Or something else entirely. And chances are they won’t always be at that company.

When it comes to people, take the long view. Ultimately, it’s not all business.

Sometimes it’s personal.

Old Dogs & New Tricks

It’s funny what you remember.

When I was a kid, one day my father brought home a set of cassette tapes. They were sort of a motivational program on creativity by a guy named Mike Vance. To give you some background, Vance’s job was to energize and activate creativity at Walt Disney and, later on, at Apple. (Working for Walt and Steve. So…a pretty creative guy.)

I think I pretty much have the entire set of tapes memorized. Vance had all sorts of crazy ideas, recommendations to try, and ‘out-of-the-box’ thinking throughout. (Incidentally, he’s the guy that popularized that term.) Listening to those six cassettes was like nothing I’d experienced before. It was transformative.

Learning New Sales Tricks

One particular anecdote had to do with the old saw that ‘you can’t teach an old dog a new trick.’ Vance goes on to explain that that thinking is ridiculous. “Of course you can!” And why is that?

Because an old dog appreciates a new trick.

This is a fundamentally important idea. People love a new thing, whether it’s the next gadget or shiny object or way to do something. They appreciate a new trick.

Be the dog that’s always on the lookout for a new trick, a new way to do things, a better technique or tool. Not necessarily the next shiny object, of course, but it’s hard to find gold if you don’t pick up a few shiny objects along the journey.

For me, using video conference calling was one of those new tricks. (See In Front of the Camera.) It came as a suggestion from a consultant that essentially insisted that our calls be conducted on Skype. Initially skeptical, I became convinced of the effectiveness of video when I realized how much less distracted my conversations were, and more memorable.

Everything is a Sales Tool

And with this whole internet thing right at your fingertips, you’ve no shortage of great ideas, troves of information, and innovative tools to discover, evaluate, and adopt (or not.) Maybe check out some of the many fantastic podcast options to pick up new ideas, listen to different opinions or simply stretch your brain. Or subscribe to a sales newsletter or two. (Or you might buy the occasional sales book, read it, and then buy copies for all your friends. It’s just an idea…)

In short, make it a habit. Be on the hunt for that next transformative or liberating idea. The payoff is worth it. And these days, they are abundant and yours for the finding.

Because who doesn’t appreciate a new trick?

Five Podcasts Worth Checking Out

  • ‘Exponential Wisdom’ Diamandis & Sullivan – For sheer out-of-the-box thinking
  • ‘The James Altucher Show’ For some of the best interviews on the Internet
  • ‘Accelerate! With Andy Paul’ Consistently good sales discussion.
  • ‘Akimbo: A Podcast from Seth Godin’ Because everything he does is worth checking out.
  • ‘The Gary Vee Audio Experience’ For sheer motivation and unbridled enthusiasm.

Links available at www.brendanmcadams.com

Sales Presentations

Disaster may await, but (at least in my experience), it’s incredibly rare that a roomful of people want to see your sales presentation fail miserably. They may be skeptical, they may prefer another vendor (or the status quo), or they may just want to get to lunch or back to their desk.

In reality, people seldom want to see you crash and burn. It may be a tough crowd, stern and silent, but they aren’t wishing for disaster. Disaster is painful to watch. It’s awkward and unpleasant. Plus, it makes time slow down and the meeting drag on. And nobody wants that.

So get that unproductive notion out of your head. Instead, consider this. They want you to win. Or at least not suck. For their own sake, if not yours.

Personally, I find the first three or four minutes the toughest. Get past that and things settle down. And as soon as someone asks a question or makes a comment, the whole mood of the meeting changes for me, so I actively solicit engagement early solely to help get me into my groove.

Figure out what works for you. Maybe it’s sitting down at the conference table with the attendees (not always practical,) or standing protected behind a podium (not always available,) or you’ve got a proven introduction that you know by heart. Think about what gets you in your groove.

Whatever it is that gets you into that place, know that your audience is probably pulling for you to get there.

Conference Ambush

There are lots of little tips and tricks when it comes to attending conferences, but here’s one that salespeople should do more often.

When attending conference presentations, make a point of being one of those people who go up and speak to the presenters afterwards. Say hello, mention some specific detail about why you enjoyed their talk, pose a thoughtful question or observation, and mention that you’ll likely follow up with them later. You might ask for their card, but chances are their email was part of the presentation. Worst case, you can track it down later.

After the session is wrapped up is better than before the presentation unless you’re very early and they’re killing time. The panelist will likely be distracted with last minute details or chatting with the moderator. (But speaking with the keynote speakers in the main ballroom is tougher, and then you’re looking more like an autograph hound than an interested colleague.)

Then follow up. You’ll need to let them get settled back in the office, so a couple days may need to pass. Then send an email. Remind them of the conversation. Maybe a LinkedIn invite. (Maybe?)

See where it goes.

Lobby Ambush

Truthfully, I wouldn’t believe this was still a thing if I didn’t recently witness it directly. Here’s how it goes…

It’s the end of the quarter and your customer still hasn’t signed off on the deal, so senior management commands the salesperson to fly to said customer’s city and park themselves in the company lobby with the explanation that they are there until the deal gets closed. (It’s evidently best to arrive a day or two prior to quarter end.)

Except that this can’t possibly work anymore, can it? It didn’t in the examples I witnessed.

If you’re in the situation where the sale hinges on harassment tactics like this, there are too many other problems with the deal, with your sales skills, or with the customer. (Not to mention sales management.)

And those problems can’t be solved by parking your ass in the lobby and waiting them out.*

Enough said.

* If you have stories to the contrary, please email me at brendan@brendanmcadams.com. I have to hear them.

The Big Meeting

Your CEO and other senior executives can be among the most effective sales tools in your arsenal. The operative words here: Can be. Think of them like cruise missiles. Very effective when judiciously deployed. Otherwise, you could be inviting disaster.

Key takeaway – Making sure it’s not a disaster is entirely your responsibility.

But stay with me, because having the right senior executive in the right sales situation is a truly beautiful thing to behold. Your customer relaxes and opens up, the conversation is elevated and expansive, new opportunities unfold before your eyes, and your sales credibility is exponentially enhanced. So you want to use this tactic. You just want to be sure you don’t screw it up because there’s no place to hide if everything blows up.

Managing the Enterprise Account

Perhaps the best opportunity to leverage your C-level resources is in the big meeting. The big meeting probably needs no additional explanation, but the basic ingredients are:

  • Senior executives from both companies,
  • A compelling event, and
  • You’re in the room.

There are things you can do to make sure nothing explodes. Rigorous preparation is key, which requires you to pay attention to the following:

  • Handle the details – This means setting up the meeting, confirming attendees, drafting and vetting the agenda, coordinating lunch, whatever.
  • Manage the message – It’s your account, so you should help determine the agenda. What needs to be accomplished? Who needs to say what? What issues might the customer bring up? Are there specific supporting documents?
  • Act as Master of Ceremonies – You’re not the senior person in the meeting, but you should nonetheless play a role. That includes introductions, coverage of relationship history, current status, small talk that gets the conversation going. Most importantly, you need to deftly keep the meeting on track. Which means making sure you’re hitting the key meeting objectives outlined above.
  • Follow up – The best part of a successful big meeting is the follow up. Own it. That doesn’t mean you have to solve the big hairy product problem or draft the legal language for an expanded partnership, but it does mean you’re making sure it gets done, and in a timely fashion. And the corollary is that it’s not the responsibility of your senior executive. Take that off their plate and assume the sales leadership role you’re supposed to be playing.
  • Communicate – Work your follow up list and keep everyone apprised of the progress being made and the accomplishments achieved, as well as any sticking points or obstacles. Be judicious and practical about what warrants escalation, but it’s the post-meeting activity that keep the momentum and dialogue going.

Of course, your senior executive needs to be the right fit and they need to be up to the task. Discreetly ask around to see what sort of experiences other salespeople have had, what the executive likes and doesn’t like, or any idiosyncrasies that you need to factor in. This is a big wager with outsized egos and personalities, so the potential for unintended consequences is significant.

Making the Executive Meeting Work

But hey, why not roll the dice? Some of my favorite meetings were completely unpredictable and totally off-script. But they were exciting, successful rides all the same. One particular CEO could keep you waiting an hour or more, then show up in shorts and Hawaiian shirt, and then simultaneously eat and talk for the next two hours of a scheduled one-hour time slot. But the conversations, wherever they happened to go, (and they could go anywhere,) were always brilliant and riveting,  leaving the client awed and convinced that this was the company to bet on.

The big meeting with the senior executive has its inherent risks, but the payoff can be worth it. Just keep things from backfiring and you’ll be fine.

What’s Plan B?

What could possibly go wrong? The self-help, positive-thinking crowd would suggest that you should always focus on the ideal outcome, force all negative thoughts from your being and imagine total, limitless success. Which is fine, up to a point.

But another way to think about things is to step up and ask yourself, “What can go wrong?” Sure, your solution is the best option for the customer. Yes, the client has all but signed. Still, in that moment, take some time and try to imagine all the ways your deal could go sideways.

Be Sales Ready

This isn’t a prescription for worry or a suggestion that you’re being too easy on yourself. Rather, taking time to imagine disaster has the curious effect of making it less likely.

Think about applying this tactic at the various stages of every deal. Make it part of your standard practice. Ask yourself what could go wrong. Where are the problems, weaknesses and unknowns? How could you lose the deal? Who is against you? What needs to happen for disaster to strike?

Use NASA as an example. There’s arguably no more skeptical, worrisome, hand-wringing crowd on the planet. They spend tens of thousands of hours trying to anticipate all the disastrous, life-threatening events that could befall any project. Most of them never come to pass. Fewer still don’t have a solution already in place.

Salespeople seldom formalize this ‘imagine a deal-breaking calamity’ component of the sales process. The result is, there’s no Plan B when a calamity does strike. There’s no deft recovery because nobody could imagine the need for one. Until there is.

Imagine the Worst

The interesting aspect of the NASA philosophy regarding serious problems is that they’re made less serious simply because they’ve already planned for them. By anticipating the problem, they’ve given themselves the time to resolve it beforehand. It’s not even really a surprise. It’s just another step, another plan that needs to be executed.

Make a habit of asking what can go wrong before it does, and then having a Plan B becomes second nature.

You won’t need it. Probably.B

In Front of the Camera

Here’s a quick tip. Whenever practical, turn your scheduled conference calls and demos into video calls. The advantages are innumerable, but here are a few:

  • Engagement – You see them. They see you. Which means they have to pay attention, and it means you have to pay attention. You can’t check email or surf the web (or shouldn’t), which means you’re getting more of them. And they’re getting more of you.
  • Information – Video delivers a better, more complete and nuanced interaction. You’re seeing facial expressions, boredom and excitement, distraction and the interpersonal activity of those on the other end of the camera.
  • Novelty – Video is still underutilized, so using it is a differentiator. If properly executed.
  • Impression – Done well, it provides you another chance to make a professional impact and convey competence.

These days, conducting a video call takes little more that activating the camera on your computer and hitting a button on the web conference application. But do it right. Wear a professional outfit. (Business casual is usually fine, but no ratty t-shirts or PJs.) And make sure your office environment conveys the right message.

Start by practicing with your internal team or partners before you start in on your customers. But start. It’s too easy and too effective not to.

Note: It’s important to note that this was written long before COVID-19…

Keep in Touch

This is particularly for the remote sales professional. If you’re not in the main office, chances are you work from home. You’ve cordoned off a room or the attic or wherever, and that’s where you ply your trade. (Mine’s in the basement now, and formally referred to as The Nerve Center.)

In this environment, it’s easy to hunker down and work away for hours at a time. You can settle in wearing your ratty t-shirt or pajamas and only extract yourself long enough to eat and use the facilities. But you shouldn’t. As a remote employee or freelance salesperson, you need to mingle.

Make mingling a habit. Find time for regular communication with others in the company. It’s easy to be ‘out of sight, out of mind’ when you’re out in the field, so let those back in HQ know what you’re doing and how you’re fighting the good fight.

Give yourself a reminder to call other team members regularly just to see what they’re hearing, share anecdotes about what works, or what you’ve learned about a competitor, etc. Emails and texts are okay, but they’re not enough. People need to hear a voice and see a face. A disembodied text message isn’t the same thing.

And find other ways to stay engaged. I’ve never been a college basketball fan and so the whole March Madness thing doesn’t resonate much with me, but I still do the brackets and try to ‘keep it real’ with the corresponding trash talk. (Bonus tip: Just pick teams randomly based on how much you like the uniform colors or the mascot. That strategy has worked perfectly for me, ensuring that I’m never burdened with the hassle of collecting the winnings.)

When you’re out in the field, it’s easy to be invisible. Stay in touch.

Sell by Walking Around

One of the seminal business books of the 1980’s, In Search of Excellence by Tom Peters and Robert Waterman, (kudos to you if you’re too young to know of it) explained the importance of ‘managing by walking around.’

The idea was that you learned things, absorbed the culture, uncovered problems and opportunities, and understood how things worked within your organization most effectively by being on the ground and among your team. Maybe this is obvious now, but it was then for many readers one of the bigger takeaways from the book.

Back in the early days of my sales career, I picked up on a variation of this approach from a Sun Microsystems sales guy. We both shared territory at AT&T and specifically Bell Labs. While I was selling them database software, Ed was busy setting them up with literally hundreds (or maybe even thousands?) of Sun servers.

One ingredient fundamental to his success was his vendor badge. By having a vendor badge, Ed could enter the building at will and roam the halls of various Bell Labs facilities with impunity. He’d poke his head into offices and cubicles, ask about projects, hand out literature and tchotchkes, and basically act like a fellow employee.

And for all practical purposes, he was. It was brilliant and transformative. He was part of the AT&T fabric and knew about projects and reorganizations long before I did. He was on top of technical issues before they blew up. He could track down and meet with engineers in real-time. This was an epiphany for me, and I immediately set to work finding a client to sponsor my own vendor badge. (A significant part of my pitch was that they’d no longer have to walk down to the main entrance to sign me in.)

Later, when I was responsible for selling to Citigroup, I was able to secure a vendor badge that gave me similar access. I’d arrive at the main IT offices early and have my coffee in the company cafeteria on most mornings. Parked there afforded me the opportunity to informally catch up with various people (especially the hard to reach executives) in an environment that lent itself to more casual, collaborative conversations. I’d become a familiar fixture, ultimately converted from being some outside vendor to part of the team.

Since Sept. 11th, it isn’t as easy to get customers to advocate a vendor badge, nor is corporate security as likely to grant it. But the idea of selling by walking around remains worth pursuing.

Be on the lookout for opportunities to walk freely among your customers.

Five Things Not to Order
at a Customer Lunch

  • Spaghetti
  • A (second) martini
  • Breakfast
  • A prune smoothie
  • Chocolate cake

You Gotta Eat

Get in the habit of frequenting a few good restaurants near your clients’ offices. Get to know the staff and the manager. Make a point of recognizing their effort, in both word and deed. Finally, let them know you’re planning to be a regular.

You don’t need to make a big deal out of it. There’s no need to show off, but having the restaurant looking out for you a little more than the average visitor makes a difference. Maybe you arrange to have an appetizer arrive just after you’re seated. Or the chef “throws together something he thought you’d like.”

This dining strategy gives you the ability to recommend entrees, know the wine list (and which expense-busting vintages to avoid,) and focus your attention on your guests rather than the menu.

And you definitely want to have the waiter run your credit card beforehand, so the bill never makes it to the table. As unlikely as it may be, this eliminates any possibility of a confrontation about who picks up the check.

These are little things. They’re just details, but that’s where the Devil is.

Who is Your Coach?

Big, complicated, strategic deals are invariably fraught with a maelstrom of people, issues, requirements and motivations. Companies seldom function with the silky-smooth precision of a Swiss watch. More often, you’re dealing with a hotbed of internal conflict, dysfunctional management, or simply an inability to execute. Getting a successful outcome and a closed deal requires you to effectively uncover, anticipate and address all these obstacles. And more.

Doing that without help is tough under the best of circumstances, and in a large organization with lots of players and complex office politics it can be impossible. You’ve got limited time, visibility and access. Even in situations where the salesperson is dedicated to one account, there’s only so much one can see and learn as an outsider.


You Need a Coach

By definition, a coach is someone in the client organization who can advocate for you and/or provide you with insider insights that can improve your odds of winning. They can read the tea leaves, tell you how your presentation landed with the key people, review documents before you send them to their bosses and help in countless other ways.

Having a sales coach isn’t a new idea, and I credit the Miller-Heiman folks for bringing the concept to life for me years ago. Basically, the goal is to have key people inside the company that can actively assist in your sales efforts. Typically (but not always,) your coach is involved in the deal, is looking for a certain decision, and has goals closely aligned with your own.

Simply put, your coach wins when you do. They have a certain, specific corporate outcome they’re looking to accomplish, and your solution helps them to advance that outcome. Your success is their success, and they’re savvy enough to know that helping you behind the scenes is good career and business strategy.


A Particular Sales Coaching Session

Perhaps the best example I can point to happened entirely by accident. I was deep into a strategic deal to be the data warehousing standard for a large Wall Street firm. Part of my preparation process is to work through the sales strategy on big sheets of paper. I would scribble out the various details of the deal: key buying criteria; decisionmakers, influencers, advocates, users; timelines; action items; etc. Each section of the worksheet would have items added and others crossed out. Each worksheet was a living document and my physical, paper-based CRM.

Placed purposely in the center of the worksheet was the most critical element to my sales strategy, the client’s organization chart. Drawn by hand, with hierarchies scribbled in and scratched out, it was rich with detail, check marks and notes alongside various names. It was also a mess, but one that I could interpret in a glance. It was my sales roadmap. Each important deal would have a similarly chaotic-looking but information-rich roadmap, the one source of truth that would go with me everywhere.

On a flight to Denver, I was seated in first class with one of my key clients for the deal. He had his nose buried in a book, so I quietly pulled out the sales worksheet for our deal, figuring I could use the time to do some last-minute preparation prior to the upcoming dinner meeting.

After a few minutes, my customer looked up from his book, curious about what I was working on. “Just reviewing notes before dinner,” I explained. My terse response didn’t satisfy his curiosity, which was now locked onto the worksheet (and the organization chart in particular), which he then pulled from my grasp and inspected thoroughly, muttering “Huh, interesting.”

An awkward silence followed. We were now months into the sales cycle for this particular deal and the worksheet reflected it. It was heavy with notes, comments and observations on all the key players. Including the guy now scrutinizing it.


Another Form of Sales Discovery

After a minute, he said “No, this isn’t right.” He then took my pen, flattened the page out on the airplane tray table, and began to edit my org chart. He added names and titles, simultaneously explaining what each correction and whether they were for or against the project and why. Stunned by the experience playing out, I scrambled to keep up and remember everything he was saying.

This coaching session continued for several minutes. He explained in specific detail the need for a new database platform, the reasons why our solution was better, who had a vested interest in the competition and why, and what I needed to watch out for. It was a sales epiphany.

To that point, we had what I’d consider a good relationship – professional and collaborative, but with reservations. Suddenly, we were at a completely different level. The conversation had changed, and he was now explaining details that were sensitive and even confidential, priceless information that would put him at some risk were it to get out.

What changed? Clearly, it was my dog-eared sales worksheet. With that document, he knew that I was serious and prepared. There were gaps and errors in the worksheet, of course, but he figured I had a coherent strategy, which meant that I could be trusted, was worth betting on and investing in. In short, we could be a team.

And from that moment onward, we were a team. He would tell me who needed more convincing, what the key messages were for which audience, who was still on the fence and whether they mattered. Maybe I could have won the deal without him (unlikely), but together we were unstoppable.

You need a coach. (And maybe more than one.) Someone to point out the blind spots, break down the competition, and elevate your game.


Finding Your Coach

To find your coach, you’ll need to figure out who wants you to win, (or who should.) And generally speaking, the higher up the food chain, the better.

Once you have that person (or persons) identified, it’s as much art as science, but it’s all selling. At a minimum, you’ll need to clearly demonstrate:

  • Competence – Your client needs to be confident that you know what you’re doing, that you understand the problem, the solution, and how to sell professionally. Without this, you can’t accomplish the next step.
  • Trust – The client needs to know that you’re reliable, that he or she can count on you, that you get stuff done. They cannot afford to hang their career on someone that can’t execute, that might embarrass them, or worse.
  • Influence – Your client has to believe that you have credibility and influence inside your company. Do you have the CEO’s ear, can you rally resources, will you be able to get things fixed when there is a serious problem?
  • Composure – Are you unflappable, presentable, executive material? Do you make the client look good? Will you stay cool when things aren’t?


It’s not easy to pull this off, and you may not be able to establish a bona fide coach for every deal. Customers are understandably wary, and it’s easy to get burned by some slick sales guy. But earn that kind of working relationship and you can expect your whole perspective on professional sales to change.

Along with your win percentage.

YES. And NO.

Saying YES feels so good. You’re being agreeable. It’s polite and accommodating. You’re satisfying the client requirements and thus, ipso facto, moving the deal closer to a win.

You can’t help it. You want to agree. You want them to be happy. And doesn’t saying YES seem like it will make your client a little happier?

YES is positive, and implies a certain momentum to it. It’s inherently optimistic.

NO, on the other hand, just sits there, imposing and stubborn and negative.

But to be a bona fide professional salesperson, you need to be able to say NO.

It’s not exclusively the right of customers to disagree or refuse. When asked, you need to be able to state clearly that the product doesn’t do something if it doesn’t do that thing. Or that it will cost (a lot) more to customize it so that it can do that thing. Or that they really shouldn’t want the product to do that thing, and here’s why.

Salespeople need to be able to say NO to incessant hoop-jumping, that thing where a prospective client makes ridiculous, pointless requests simply because they think they can.  Because they’ve come to the conclusion, mistakenly, that salespeople can just be told what to do.

And you must be able to really say NO to a bad deal or a bad customer. When confronted, sale professional can say NO:

  • When the product doesn’t do what they ask.
  • When the customer lies or makes an inappropriate request.
  • When the deal has no profit margin and none in the future. There are customers out there that refuse to recognize your need to generate a reasonable margin. Let your competitors deal with those customers.
  • When the customer is ill-suited to your offering. (Hard to walk from, but you know it’s right.)
  • When you know the customer is destined to become a support nightmare.

The thing about saying NO is that it gets easier to say once you’ve done it a few times. Your clients aren’t accustomed to hearing it from their vendor, so it might take them by surprise. But it’s another little thing that will differentiate you from the sales ‘talent’ they’re used to dealing with.

Done right, a well-intended NO will result in you hearing a lot more of YES when it matters.

Five Gadgets from
the Sales Archives*

  • Palm Pilot
  • RIM Blackberry Curve
  • Motorola StarTac flip phone
  • Motorola Bravo pager
  • Compaq Portable II computer (with Lotus 1-2-3)

*  And there’s a story for every one of them.

Making Introductions

Here’s a quick tip. Make a habit of introducing your customers to each other.

This is only my opinion, but part of your job is (or should be) to connect people and help foster relationships. Doing so further differentiates you by emphasizing your role, not as someone trying to make the next sale, but as a trusted advisor and colleague.

When you get your customers talking to each other about you and your company, you’ve got no choice but to stay on your toes and do your job. When you actively encourage and even invite that interaction, you’re making it clear you’re confident and have nothing to hide.

More importantly, consider the value it provides to your customers. These are introductions not otherwise likely to be made, for competitive reasons or due to geographic separation. But the benefit can be great, whether for career advice or sharing perspectives about the industry. Or just networking. And you will have made that relationship happen.

I’ve made more customer-customer introductions than I can count, and always to good effect. The initial logic was to help my sales efforts, figuring that a prospective customer is more likely to believe my customer’s favorable reference than they are me. And while it tends to be a ‘warts and all’ assessment, it has consistently proved a sound strategy.

It’s typically initiated during a meeting or phone call, as in “You need to talk to this guy. His application does exactly what you’re talking about.” Or it could be as simple as providing an unsolicited reference scrawled onto a business card, with a follow up email to both contacts.

One inevitable outcome of these connections is the personal razzing I receive, with my particular idiosyncrasies and character flaws explicated in painful detail. (I guess it’s a small price to pay.)

So, from time to time, give some thought to picking up the phone and telling someone, “Hey, you should meet…”

Smaller Calls

More is better. But smaller can be better, too.

We’re talking about sales calls, of course. The most effective, informative conversations are one-on-one. The same is true with sales calls. How often have you ever experienced a truly productive, interactive session when there are even five or six people?  The group dynamic becomes too powerful, and it only gets worse as more people get added to the mix.

Ideal sales calls are engaged, active conversations. The goal is to learn, understand, educate, connect, influence and motivate. With every added contributor, you’re also adding complexity and the problems inherent with that dynamic. Whenever possible, make your sales call smaller, with fewer participants.

More people also means more choreography and planning, so think carefully about who to include and specifically what role each attendee should play. A more complex chemistry is at work here. Who talks? What needs to get accomplished? Who leads? Orchestrating a meaningful, productive conversation among even a handful of people can be challenging, and it’s the rare team that pulls it off effectively. Personalities and egos are inevitable, creating a situation that’s difficult enough to navigate with your customer, let alone among your internal team.

Less is More Sales

Simple math also plays a role. Adding someone from your team to the meeting potentially subtracts from the time that the customer can speak. Perhaps significantly. That rarely leads to a good outcome. You want your customer to feel free to speak openly and at length, but every additional attendee works to eat into that possibility.

Ask yourself if a particular person is critical to the conversation. Can they help move things forward, build credibility, drive discovery or solution definition? If yes, then include them. Otherwise, they’re complicating the process, putting an added barrier between you and your customer, and decreasing the likelihood of a productive meeting.

Of course, some situations prevent you from disinviting attendees. This is less a problem with customer attendees (unless they’re at risk to share sensitive information with your competitor or disrupt the conversation) than with your fellow employees. In these instances, who attends will likely require some negotiation.

For your teammates that do attend, you need to clearly convey your meeting objectives during the sales prep session. Even something as simple as explaining that “during the first twenty minutes I want to learn about X and Y, and that I want to leave ten minutes at the end to talk about our support plan” can help your team appreciate that you have a strategy, and that they’re a part of it.

The Power of Smaller Sales Calls

If you can also explain what they should plan to contribute (and discuss what those comments might be), that guidance can have a significant impact on your meeting’s effectiveness. Importantly, detailing these roles and expectations helps to reinforce to the team that you’re leading the meeting and have a specific objective in mind.

When you can, consider breaking the meeting up. It’s almost always better to have three one-on-one conversations than one large session. (The obvious exception might be in the case of conducting a demo or a more formal presentation.)

A group engagement can be advantageous, but not always. People are more open when they are not competing with their peers for talk time, and they’ll often share specifics they would never volunteer in a group setting. The group presentation can prove invaluable to understand the political dynamic you’re contending with, but one-on-one conversations are a better avenue to establishing rapport and getting candid feedback.

Ultimately, touches and meaningful interactions are more effective in small settings. Invest in small calls. They lead to bigger things.

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