26.2 Reasons Why Sales Success is a Marathon Pt. 2

By Marc Pollina

Okay, your legs are heavy, you’re starting to doubt you can hold your pace, and your hamstrings are angry, but you’re halfway home!

If you were running the NYC Marathon, you would be crossing the Pulaski Bridge from Brooklyn to Queens. Stay focused and keep that cadence at 180 strides per minute. We’ll get you through the Bronx and Manhattan. You’ll have a volunteer swaddling a mylar blanket around you in Central Park in no time. You got this!

14.0  Run the first third with your head, the second third with your legs, and the last third with your heart

Marathoners often repeat simple phrases to keep them on task throughout the race. My marathon mantra is “conserve, cruise, conquer” which is a stripped-down way of saying be smart and conserve energy in miles 1-9, get your legs in a rhythm in miles 10-18, and dig deep to conquer all the demons you’ll encounter in miles 19-26.2.

The 2011 Boston Marathon was rare because the weather was nearly perfect (44 degrees at the start, 61 degrees at the finish, and partly cloudy with persistent 25 mph winds from the west). For those of you who don’t know, the Boston course runs (nearly) due east, so a prevailing westerly breeze is a dream come true. Despite the ideal conditions, I hit the half in 1:31 and finished in 3:24, a massive positive split. Why?

Well, my heart wasn’t in it. I was physically and mentally prepared, but I wasn’t emotionally ready to give everything it took to actually run a sub-3. To be successful, you need all three.

Have you ever tried selling something when your heart’s not in it? There’s an old expression “if you have one more reason for your prospect to own your product than he or she has not to own it, you’ll win the sale.” I guarantee if your heart isn’t in it, you’ll run out of reasons pretty fast.

So, how do you emotionally prepare to sell? The answer lies within your “why.” Simon Sinek’s “Start with Why” says it best, “people don’t buy what you do; people buy why you do it.” When Steve Jobs was recruiting Pepsi executive John Sculley to become CEO of Apple, Jobs asked him “do you want to sell sugar water for the rest of your life, or do you want to come with me and change the world?”

How could John say no? When your “why” is that good, there’s really only one answer.

That’s heart. That’s why. That’s sales.

15.0  Gear matters

Okay, okay. I know I said “pause your Garmin” (see Pt. I, Reason 12.0), but this is 2020 and, well, gear matters, too. A lot.

Don’t believe me? One word. Vaporfly. Marathon world records were broken in 2018 (men) and 2019 (women) in, you guessed it, Nike’s controversial Vaporfly shoes. The first version of the Vaporfly was christened the “4%” because Nike advertised the shoe could make its wearers 4% more efficient, meaning they need that much less effort to produce the same pace.

The Vaporfly contains a “secret weapon,” a full-length carbon plate that propels a runner forward. Retired American marathoner Ryan Hall stated “when a shoe company puts multiple carbon fiber plates in a shoe with cushion between the plates it is no longer a shoe, it’s a spring, and a clear mechanical advantage.”

Does this mean a casual jogger can put on Vaporflys and challenge the elites? No. Does this mean an Olympic marathoner can’t run fast in another brand or model? Also, no. In fairness, Vaporflys are just one gear choice that can assist you in running faster. Compression socks, technical fabrics, smart watches, treadmills, and plenty more are available. But, it’s worth noting that advanced technology in the hands (or on the feet) of the right person can elevate performance to previously unachievable levels.

What about sales? Can the right MarTech stack make a difference, too? Yep. A lot.

The good news is there’s no shortage of technology to choose from. The bad news is there’s no shortage of technology to choose from. Let me explain. Because companies often acquire a plethora of tools and systems (many disparate and unable to communicate with one another), the biggest challenge is stitching them together to deliver coherent, actionable intelligence to do what they’re meant to do, increase operational efficiency and maximize recurring revenue.

Like the Vaporfly, can one specific sales and marketing tool make a difference? Yes, to a degree. If your company doesn’t have a CRM system, implementing a robust CRM will move the needle forward. But, much like running, you’ll benefit more if you incorporate and synthesize multiple technologies rather than rely on just one.

How do you manage customer relations? Cross-team communications? How about social media? Campaign management? User experience? Ad spend? A/B testing? Sales automation? Traffic conversion? Customer experience management?

Having the right “gear” is fundamental to sales success, too. Tools automate processes, save time and money, and help keep marketing and sales aligned and focused. Even better, digitizing your sales process creates dynamic assets (content, backlinks, social media engagement, etc.) that create a “flywheel” of revenue generation momentum. To create data-driven, personalized experiences for customers, you’ll need streamlined, connected digital tools.

Are you at risk of losing business because your competitors have better gear?

16.0  Find comfort in discomfort

My best year of running was 2016 when I set personal records (PRs) at every distance from 5k to the marathon. Why? Well, I raced a lot. It’s tough to PR when you don’t. But, more importantly, racing allowed me to “find comfort in discomfort” in a way that training never could.

I had an epiphany when I raced the 2015 BAA 10k, an out-and-back course on the streets of Boston that allows runners to see the entire field. I watched the elites in the lead pack fly by me at 4:30/mile pace. Let’s be clear; you can’t run six successive miles at world-class pace without tremendous discomfort.

Later in the race, I saw back-of-the-pack runners averaging more than 14:00/mile. There was plenty of discomfort among them, too. The difference was the elites looked so darn comfortable with their discomfort. They could “redline” their effort and remain calm. How?!?

It turns out, the answer isn’t so complicated. Race. Professional runners race far more often than we amateurs do. And, when they train, elites incorporate quite a bit of speed work and fast tempo runs that approximate the discomfort they’ll experience on race day. My success in 2016 was due in large part to my increased threshold for pain and my heightened ability to tolerate it and stay relaxed.

Is there discomfort in sales? Plenty. Have you ever made 300 dials in a day? That’s not easy for anyone, no matter how talented the person is dialing the phone. How about cobbling together reports to assess performance across a complex web of vendors, campaigns, and content assets?

A significant difference between elites and back-of-the-pack sales professionals is the ones who have found success find comfort in discomfort. They’ve given so many presentations that those uncomfortable objections (which would derail less-hardened professionals) have been answered dozens and dozens of times. And, much like elite runners, the best salesmen and saleswomen maintain a Zen-like calm in the face of such adversity. They don’t just answer objections. They highlight features, reinforce benefits, and close the deal.

Find comfort in discomfort. Your best year in sales won’t be possible until you do.  

17.0 Plan the work. Work the plan.

To date, my best marathon has been the 2016 NYC Marathon (2:58:49). I ran the 2017 Chicago Marathon (2:58:31) faster, but I was in better shape and Chicago is far flatter and faster than navigating NYC’s five boroughs and final hills of Central Park. There are many reasons why, including a little divine intervention (see Pt. I, Reason 1.0), but the biggest reason was I plotted out a four-month daily training schedule and followed it to a T. I planned the work and worked the plan. Easy in theory. Not so easy in practice.

If the day said “8 miles – easy,” I ran eight miles easy. If the day said “8x400m @ 5:20/mi. with 90 seconds recovery,” I went to a local track and ran eight 400s, averaging 1:20 lap. It didn’t matter if it was raining sideways, sunny and 90 degrees or windy and 15 degrees. You get the idea. I was a machine. I was determined. I wouldn’t be denied.

“Plan the work. Work the plan.” reminds me of the 2011 Boston Marathon, too. I was one of ten members of a charity team that year and we were having our post-race celebration party, lamenting about how poorly our races went. One teammate who had run his very first marathon disagreed. He was ecstatic; he went sub-4 (3:54) in his debut and he was the only one of us who had negative-split the race (see Pt. I, Reason 13.1). The rest of us were defeated and admired him with awe. “How did you do it?” we asked. He looked at us and answered, “remember that training schedule we got with our welcome packets?” We had all ignored or discarded it, but we nodded in unison “yes” because we knew what he was talking about. Then, the first-time marathoner laid down some Yoda-like, timeless wisdom and matter-of-factly said…

“Well, I followed it.”

Boom. Mind blown. Lesson learned.

Peter Drucker, the legend often regarded as the greatest management thinker of all-time, said “if you can’t measure it, you can’t improve it.” So true. That’s why we runners time our races and workouts. That’s why we sales professionals develop business plans, create metrics, and chase quotas.

If you can’t measure each part of your business, you can’t manage or grow it. Your plan should focus on improvement and developing a strategy for maximizing your sales performance in both the short- and long-term. Monitoring sales analytics increases performance and improves accountability.

Plan the work. Work the plan. Don’t be denied.

18.0 Sometimes you just have to do something before you think you’re ready to do it

One of the most inspirational stories from the 2020 U.S. Olympic Marathon Trials was the surprise 2nd place finish of Molly Seidel. In arguably the deepest field in Trials history, Molly seemingly came out of nowhere and pushed the leaders. One by one, marquee American runners (Jordan Hasay, Molly Huddle, Sarah Hall, et al.) dropped out of contention, yet little-known Molly plugged along on a hot, hilly Atlanta course.

In the 2015 NCAA outdoor nationals, Molly’s coach told her “sometimes you just have to do something before you think you’re ready to do it.” I love that. Molly believes her coach meant finish in the top-eight to secure All-American honors, but Molly pulled off a huge upset and won the 10k NCAA title that day. Not to be a one-hit wonder, Molly employed that same logic to earn her spot on the U.S. Olympic team.

When I first started in sales as a financial advisor, I was asked by my supervisor to mentor a newly hired broker on the floor. It was 8:30 a.m. EST and I was helping the recent college graduate make some of his first sales calls. One particular call went south in a hurry. My trainee was chased off the phone by the prospect in less than 20 seconds. When I asked him what went wrong, he answered “the guy’s in California. Just woke him up. He told me he’d give me 60 seconds before he hangs up. I apologized and let him get back to sleep.”

As his mentor, I had a decision to make; do I tell the trainee to move forward and dial the next prospect on the east coast or do I step out of my comfort zone and turn this into a teachable moment? Despite nearly every fiber of my being telling me otherwise, I chose the latter.

I picked up the phone and dialed the California number. As the phone rang, I explained to my trainee that it was okay for the prospect to hang up on you (a firm “no” is always better than a “maybe”), but it was unacceptable to give up on a prospect that has expressed interest (even if it’s 5:30 a.m. local time and the level of interest was questionable at the time). As the phone continued to ring, my heart was racing. I thought I’d get off the hook and leave a message, but then the unthinkable happened… he picked up.

“Hello. My name is Marc. I just overheard my colleague talking to you. I understand it’s early and you’re tired, but I have a stock idea that has Wall Street wide awake. I’ll take those 60 seconds.”

One minute later, I transferred the call to our account administrator who helped our new client fill out his new account form. Sometimes in sales you have to do something before you think you’re ready to do it. It might be digitizing your sales. It might be purchasing a new software tool to amplify your sales. It might be as simple as picking up the phone to make an important dial.

Just do it. Do it today. Do it now. Before you’re ready.  

19.0 Run slow to run fast

On an idyllic Southwest Florida day long ago, I raced Deion Sanders in a 60-yard dash. It was a Cincinnati Reds tryout camp, and I needed to run fast to impress the scouts. It went great for Deion. Not so much for me. For those who don’t know, Deion is fast. Superhuman fast. One-of-the-fastest-in-history fast. I’m not. He ran a 6.3 in unlaced basketball hi-tops. I ran a 6.9 in laced cleats. But, I digress…

Oh, and then Deion became a Hall of Fame NFL superstar and Major League Baseball All-Star. There’s that. But, Deion isn’t a marathoner. And, I can say with certainty (and enthusiasm) that I am fully capable of beating Deion in a marathon on any given Sunday (or day that ends in –day). And, Deion, if you’re listening… game on. Bring it. I will race you. It’s time to even the score.

Okay, marathoners are a different breed. Running slowly allows marathoners to improve the energy system most essential to long-distance running, the aerobic energy system. When you sprint, you reach your aerobic threshold very quickly and your body switches over to its anaerobic energy system.

To maximize the efficiency of the aerobic system, you have to run slowly. One of my favorite marathon training runs is an early morning, very slow, pre-breakfast long run of more than two hours. Why? Because you not only engage your aerobic system, but you get the added benefit of exhausting your glycogen stores, enabling your body to learn how to burn fat as a source of fuel.

So what does this all mean for sales? The “energy system” for sales is aerobic. HubSpot defines inbound marketing as a journey: you attract strangers, convert visitors, close leads, delight customers, and transform customers into promoters. That’s far from a sprint. Each stage takes time.

It takes confidence to run slow. It takes confidence to trust the sales process. But, if you don’t develop the proper habits, you’ll underperform as a salesperson. The slow, deliberate pace of a long distance runner is the proper cadence for the successful sales professional. 

Much like marathoners want their bodies performing in the aerobic zone for as long as possible from the start to the finish on race day, sales professionals want to nurture prospects methodically from the top to the bottom of the sales funnel. If you’re partial to the flywheel metaphor that recognizes there’s no end to the customer journey, you know that “feeding” any part of the flywheel (attracting customers, engaging with prospects, or delighting advocates) takes time. Customer-driven sales momentum doesn’t occur overnight.

The beauty of running slow is it allows you to run farther. And, the farther you run, the more efficient you become. Your form improves. Your aerobic engine strengthens. The net result? You’re better. You’re faster. And, that’s the end goal of sales, right?

20.0 One run can change your day. Many runs can change your life.

I like to run at sunrise. Before breakfast. Before work. Before I’m fully awake. My run is my time. My legs are on auto-pilot so my brain is free to contemplate whatever demands my attention that day (work priorities, family matters, creative endeavors, or otherwise). My run sets the tone for my day and changes it for the better.

By contrast, my running “career” has spanned more than 20 years and it has truly changed my life. When I ran 16 straight Boston Marathons, running wove itself deeper and deeper into the fabric of my identity. Baseball was my childhood religion and first love and I played it from age 6 to age 23, but running has transformed me in ways that baseball never did.

Running is part of my lifestyle. I love the challenge. I love the escape. I love the peace. I feel like running and I were meant to discover each other. I, literally, run for my life. And, I intend to keep running for a lifetime. The miles are measurable, but the rewards are infinite. 

One sale can change your day. I’ll never forget receiving a phone call from a significant prospect in Boston when I was in Naples, FL. The prospect called to inform me that she and her company had chosen to work with me and my firm. The sale had taken one year from first contact to signed contract. I was elated. She was elated. She reached out to me when I was on vacation because she just couldn’t wait to share the good news in person. She made my day. 

Many sales can change your life. In a previous life, I helped leadership teams monetize their hard work when their companies went public. By helping founders and top executives sell their hard-earned equity awards, I saw enormous wealth created first-hand. Many of the companies’ annual recurring revenue had reached critical inflection points, allowing them to file their S-1 and launch an initial public offering (IPO). In many cases, executives’ net worths grew 25x to more than 50x. The wealth that was created was truly life-altering.

But, the benefits of sales success aren’t just monetary. Like runners’ accumulation of miles, success in sales spills over into other areas of executives’ lives. The confidence, rigor, and superior communications skills necessary to achieve sales success are life skills that translate quite nicely outside corporate walls. The “beat yesterday” mentality that is ingrained in sales professionals comes in handy in many facets of life, too. And, I’m never surprised to learn a successful sales executive has earned accolades or rewards beyond the office.  

Sell. Sell, again. Sell often. Nothing happens until someone sells something.

21.0 Breathe in strength and breathe out weakness

Olympian Amy Cragg once said her marathon mantra is “breathe in strength and breathe out weakness.” She said it calms her down and helps her focus. It worked pretty well for her when she won the U.S. Olympic Trials in 2016.

Any mantra that keeps you strong and indomitable in the latter stages of a marathon is a good mantra. Heck, a marathon is a long way. But, I particularly like this one because the idea of inhaling strength and exhaling weakness is so compelling I’ve borrowed it during races and tough workouts.

An efficient sales funnel or flywheel breathes in strength and breathes out weakness, too. By identifying and fortifying weak areas in your sales funnel, you can improve the percentage of leads that become clients, repeat customers, and promoters of your brand. Often, the weakest area of the funnel is the “nurturing” area in the middle. Marketing controls the top (demand generation). The sales team controls the bottom (customer generation). It’s the gray area in the middle that needs more attention (and often gets the least).

A good amount of qualified leads may start on the trail to making a purchase, but a relatively small percentage of prospective customers will make their way to the bottom of the funnel to become sales. These potential customers will disappear through the cracks in your funnel.

So how do you fix the cracks in your sales process and breathe strength into your funnel or flywheel? Finding out where along the customer journey your potential customers are getting lost is the first step. Are you monitoring and measuring how users are interacting with your site while they’re in the early stages of the funnel? There are analytics tools that can be used to track the customer journey. A funnel visualization report helps you identify what the culprits are (poor content, confusing designs, weak calls to action, etc.).

Many of the weaknesses in the middle of the sales funnel can be strengthened by “digitizing sales” and tightening the automated sales process. Heat maps and A/B testing can help improve website weaknesses. A robust CRM makes it easier to track each customer’s journey and identify where customers need more support.

Once you understand what parts of the customer experience you need to improve, you’ll want to employ a wide variety of contact methods to answer questions, nurture them, and provide every prospective customer with the guidance he or she needs during the latter stages of each personalized customer journey.

Breathe in strength and breathe out weakness. You don’t need to be an Olympic marathoner to reap the rewards.

22.0 She believed she could, so she did.

This one is a shout-out to my only sibling, my awesomely driven sister Connie. If her peers in her youth would have voted, she would have been selected “most likely to earn a 4.0 GPA” followed closely by “least likely to run a marathon.” Sports, in particular, were my thing, not hers. But, we’re very alike in one way; we’re both Type A high achievers.

So, when she told me she started to run for the first time at age 52, I was in shock. I thought she’d run a few miles, get a few blisters, and give up. I should have known better. I should have known it was in her DNA to do just the opposite. She became obsessed.

She built up slowly and eventually ran a 5k. Then, she ran a 10k. Then, multiple half marathons. Then, she asked the question I knew was coming next, “do you think I could run a marathon?” I told her she could, but she didn’t really believe me.

Fast forward one year later, at an age when most humans are giving up on fitness, I watched my sister cross the finish line of her first marathon, the Celebration Marathon, beating her sub-5 time goal with a 4:58:21. She had the biggest smile on her face I’ve ever seen. The sleeves on her raised arms were inscribed with her mantra, “she believed she could, so she did.”

We’ve all worked at companies where sales are “in a rut” and some of us have been fortunate to work at companies that have “rocketship” trajectories. What’s the difference? I would argue your rocketship has no business being in the sky unless it’s pointed at something previously thought to be unattainable. But, before you fire up the engine, you need to believe. You need to believe you will get to $100M ARR when quarterly revenue is just $500k.

To be successful in sales you need vision. You need to see a far away goal even if others don’t. But, there are plenty of visionaries who are just dreamers. That’s why you need to believe to achieve. And, once you do, you need the discipline to execute a plan that plots your journey to your destination. I would argue the action plan is the easier part. It’s the belief that takes guts.

And, as my sister will attest. It’s never too late. 

23.0 You can’t outrun your fitness

To run a sub-3 marathon, you need to run 26 straight miles at a pace of 6:52/mile or faster. That’s it. Pretty straightforward formula.

To pull it off, you’ll need to keep your heart rate (HR) in check (I averaged 156 bpm during my sub-3 at NYC). You’ll need to be healthy. You’ll need a strong training cycle. You’ll need good weather. You’ll need a happy stomach. You’ll need to fuel properly. You’ll need a lot. And, all those things are subject to change. But, the formula will never change.

By contrast, I ran 5.1 miles this morning at 7:21/mile in ideal conditions and my HR averaged 152 bpm. Ouch. That’s not good. And, that’s my point. I worked hard to run 30 seconds/mile slower for 20% of the distance. I’m not in shape to run a sub-3.

I ran the Celebration Marathon in January. I hit the half in 1:33:23 and positive-split my way to a 3:14:01. That’s an accurate representation of my fitness. To be fair, it’s June and we’re in the midst of a global pandemic, so I’m likely in worse shape today. It hurts to say it, but it’s honest.

You can’t outrun your fitness. And, that goes for sales, too. If your ARR is $2M and you want to get to $100M, you’ll need to look in the mirror and assess whether your company has the fitness to pull it off. Probably not. At least not yet.

It reminds me of my college baseball days. Our team was down by seven runs in the fourth inning. I led off the top of the fifth and took a mighty cut on the first pitch (which happened to be out of the strike zone). The third base coach called time-out to talk to me. His advice was simple, “Marc, you can’t hit a 7-run homerun. Be patient. Walk if you have to. Just get on base.”

You can’t leapfrog from $2M ARR to $100M. The good news is you can chip away to $5M, $10M, $25M, etc. on your way to $100M. You’ll just need to incrementally improve your fitness (tech stack, headcount, operational efficiency, and more) to scale your way to success.

What shape is your sales organization in? Do you have the fitness to reach your goals?

24.0 No two races are the same

People often ask why I ran 16 straight Boston Marathons. I understand the question. It seems a little redundant to run the same race over and over again. And, from the outside looking in, that’s true. But, we runners know a secret. No two races are the same.

In 2012, Boston was sunny and 86 degrees and I finished in 4:10. In 2007, Jim Cantore from The Weather Channel was in Hopkinton as 70 mph gusts blew signs off buildings when I clocked 3:36. In 2013, I crossed the finish line in 3:28, just 35 minutes before the bombs tragically interrupted near perfect conditions. But, it’s not just the weather that changes.

Life changes, too. In 2004, I ran with a friend who has since passed away. In 2005, I was in the midst of a divorce. In 2017, I ran step-by-step with my wicked fast girlfriend and we finished in 3:28:29. No two races are even close to being the same. And, that’s part of the fun.

No two customers are the same either. And, no two customer journeys follow the same path. We sales professionals and marketers like to build ideal customer profiles and segment our audiences, but we shouldn’t trick ourselves into thinking we’ll ever run the exact same race twice.

Don’t believe me? Market conditions fluctuate, too. How about a global pandemic to throw a curve into your 2020 sales forecasts? The financial crisis of 2007-2008 wreaked havoc, too. When the dot-com bubble burst in 2000-2001, the corporate landscape was altered forever.

So what do you do if change is the only certainty? The answer is test, test, test. Test your content. Test new vendors. Test new technologies. Test, again and again. And, look for ways to gain a competitive advantage, always.

The corollary to test, test, test is customize, customize, customize. Just like a marathoner needs to customize his or her effort given the course, race day conditions, etc., sales professionals need to customize customer journeys to suit decision-makers, market conditions, and all other factors that enter into the buying decision.

Do you feel like you’re running the same race over and over? You’re at a disadvantage if you do.

25.0 HTFU

We sales and marketing professionals love our acronyms (MRR, ABM, SQL, KPI, ARPA, etc.). Runners have a few of their own, including this gem I learned in 2011 while running with a charity team whose founder is a nun. I’ll refrain from spelling out the expression the letters represent. A simple Google search should do the trick.

A marathon is hard work. At some point(s) during the race (typically later, but negative thoughts can creep in at any mile), you’ll face a gut check. You’ll be in significant pain. Your legs will be filled with lactic acid. Your calves will be cramping. Your thighs will be chafed. Your thinking will be fuzzy. You’ll hit a point where you’ll ogle a spectator holding a beer or see a hammock, lake, or subway, and you’ll ask yourself, “why am I running?” This hurts. I’d rather be drinking that beer or in that hammock, lake or subway.

That’s precisely when you need someone to yell “HTFU” in your salt-stained ear. Sorry, not sorry. You deserve it. You signed up for it. Pain is temporary. Pride is forever. Get to the finish.

Sales is hard work. You’re going to be rejected. A lot. You’re going to be ghosted. Your top prospect will go dark. Your customers will squeeze you on price. Your competition will undermine your credibility. Your demo will freeze in the middle of your presentation.

Oh, and your territory will shift. Your mandate will change. Your quota will increase. Your total compensation will be altered. And, an unforeseen pandemic will shock the world.


26.0 Don’t celebrate too soon

I once ran a 5k and my goal was to go sub-19 for the first time. As I was approaching the finish, the clock read 18:50. I had my goal “in the bag.” I was in typical race pain, so I backed off the throttle, high-fived a spectator, and coasted through the timing mat at the finish line. I figured I finished in 18:55-ish. But, no. On the way home from the race, I looked at the online results and saw “19:00” next to my name. I was livid. Actually, worse. I was nauseous. How did I mess that up?

I was to blame. And, in fairness, it was only a 5k, so I had only exerted effort for as long as most people take to eat a sandwich or play a hole of golf. But, what if it were a marathon?

I know a runner who finished in 3:00:22 and missed going sub-3 for the first time. I can only imagine how many times he replayed the race to figure out how he could have run just one second faster per mile.

Have you ever celebrated a sale too soon? I once worked with the leadership team of a private company that was planning to go public. I got to know the founders, Section 16 officers, members of the board, general and outside counsel, and started customizing trading schedules for all company insiders. I had spent a year of my life working on the sale.

On the eve of the IPO, the company was acquired in an all-cash deal. No IPO necessary. No trading schedules necessary. Poof. The opportunity vanished.

The good news is even though the equity management opportunity had disappeared, the unforeseen acquisition created a new opportunity to manage wealth on the back end of the sale.  

Don’t celebrate too soon. Sell your hardest from the top of the funnel to the bottom. Control your effort. And, if something goes awry that’s out of your control, sell again. You might just uncover an opportunity you never expected.

26.2 Finish smiling

So, you’re in the homestretch. You’re in significant pain, but the crowds are going crazy and a wave of adrenaline will help you move your legs faster than you thought humanly possible. Don’t be a curmudgeon. You know who I’m talking about. You’ve seen the runners who look like they’re angry at the world. They’re the same ones who ignore your wave and run past you with RBF at your local park.

And, when I say “finish smiling,” I don’t just mean flash a quick grin for the photographers at the finish. You just ran a marathon. I’m talking full-on perma-smile, the kind that should be etched on your face for everyone: family, friends, teammates, coaches, volunteers, spectators, passersby, women, children, pets, and anyone and anything else in your midst.

Why? This isn’t all about you. Sure, you trained for it and ran it, but what about your significant other who woke up at 4:30 a.m. to make you breakfast and coffee before your race? What about the thousands of volunteers who handed you Gatorade, water, Gu, and bananas? What about the fans who screamed your name at mile 21 when you were feeling rough? The least you can do to return the favor(s) is to be grateful and smile.

And, while you’re at it, take note of how you feel in this moment. Trust me; you’ll want to experience it again. You’ll have much to assess in the days ahead. What went right? What went wrong? How can I improve? But, no matter how much analyzing you do, please promise me you won’t forget the feeling of crossing the finish line. Channel it when you need it. It’ll come in handy on the roads and off.

There’s plenty of repetition in running and no shortage of it in sales. It’s not too difficult to become robotic when calls, emails, presentations, and follow-up meetings start to blur from one prospect to the next. Are you glazed-over like a tired marathoner when you’re giving your third presentation of the day? How about your virtual meetings (Zoom, UberConference, Google Meet, or otherwise)? A camera tends to sap the life from you, so that abbreviated smile that works in person needs to be a bit wider on screen.

Much like when a runner completes a marathon, a sales professional who closes a big sale can use the opportunity for two important, often overlooked, imperatives: 

  1. thanking everyone who contributed to the win for his or her support and help (colleagues, vendors, assistants, etc.) and 
  2. bottling up the magic (and learnings) responsible for the success and using it as a blueprint to improve the sales process and better position the company for further success going forward.

Smile. Be grateful. Thank your team. Learn from your success (and mistakes). Repeat.

Congratulations! You’ve persevered. You may not have a medal around your neck, but you deserve one, and you’re now empowered with 26.2 reasons to sell circles around your competition. So, you’ve got that going for you. Which is nice. 

If you had just finished the Chicago Marathon, you’d be sprawled out in Grant Park quaffing a celebratory Goose Island IPA. Enjoy every sip. And, rest. You’ll need it. But, don’t simply rehydrate, kick back, and rest on your laurels. 

I have a hunch you can run even faster, am I right? You’re in sales. You’re a competitor. This isn’t just a checkmark on your bucket list. This is life. You got this. C’mon. HTFU. Why don’t you lace up again and give it another try?  


11 Essentials to Digitize Your Sales Process