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Welcome to the “Savvy Seller”
Shadow Seller’s stories that  simplify…

Welcome to Shadow Seller's blog, where we're all about ditching outdated sales methods for cutting-edge excellence. Here, we offer insights and strategies to boost the savvy of sales leaders, pros and CEOs. Dive into innovative sales tactics, bust myths, and discover hidden gems to streamline your workflow and enhance productivity. Our posts are packed with practical tips and real-world examples to shake up your sales approach. Whether you're a sales vet looking for an edge, a sales leader trying to finally overcome some of those repetitive problems or a CEO aiming for growth, you've found your resource. Join us on this journey to sales success and stay tuned for content on making sales simpler and more effective. Welcome aboard Shadow Seller's world



I always hated the Sunday Scaries (who doesn’t?), even in the early part of my career when sometimes I thought I had nothing to worry about. They weren’t bad when I worked for a good company that treated people well. That seems to be a thing of the past. The Scaries were much worse when you had a loser boss or “teammates” – particularly the bullying types, which seems to be the majority these days. Without dwelling on the toxic workplace let’s figure out what the Sunday Scaries are and maybe how we can use (yes, you guessed it…) artificial intelligence, to combat them.


What Are the Sunday Scaries & Why Do We Get Them?


The Scaries? They’re that feeling of dread that creeps up on you as Sunday afternoon starts to turn into Sunday evening. They’re the wave of anxiety about the impending work week. The shadow that’s cast by looking ahead. What's really happening in your brain and body during these moments? It's a fascinating interplay of psychology, neurology, and sociology.


  1. Anticipatory Anxiety: This is your brain's natural response to upcoming stress. It activates the amygdala, triggering the release of stress hormones like cortisol, as you think about the upcoming workweek.

  2. Modern Work Culture: Societal pressures equating busyness with success intensify feelings of anxiety and dread about work, particularly evident on Sundays.

  3. Weekend-Weekday Contrast: The shift from weekend freedom to weekday responsibilities creates a psychological jolt, leading to heightened anxiety on Sunday.

  4. Disrupted Routines: Changes in sleep patterns and routines over the weekend can disrupt your body's internal clock, contributing to Sunday evening stress.

  5. Coping Strategies: Recognizing these patterns allows for better coping mechanisms, such as mindfulness, relaxation, and strategic planning (like using AI tools) to ease into the workweek.


How to Combat the Scaries


Now, let's not just wallow in our Sunday sorrow. Here are some tips to combat those Scaries:


  1. Plan Ahead: You could spend a few minutes on Friday jotting down Monday's tasks. Don’t wait until Sunday night to do this, which is what most of us do. It's like leaving breadcrumbs for your future, anxious self.

  2. Sunday Funday: Keep yourself engaged in activities you love. Distraction is a powerful tool. In my twenties, during the Summer months, I used to play cricket (it’s like baseball) ALL weekend.

  3. Relaxation Rituals: Whether it's yoga, reading, or watching your favorite show, establish a Sunday ritual that calms your mind.

  4. Perspective Shift: Remember, work is just one aspect of life. Don't let it steal your Sunday joy.

Focus on planning


Planning? What a bore! Lett's spice it up with a couple of (pretty good) clichés – "those who fail to plan, plan to fail." AND the law of the Seven Ps “proper planning & preparation prevents p*** poor performance.” As much as you want to defend the weekend and squeeze the last juice of joy from it, you don’t want the specter of last minute catch-up on a Sunday evening looming over you, but that problem isn't gonna solve itself. Plan your way out of it! Get the planning & prep out of the way on Friday and then crack on with your weekend.


Sales World


People not in sales tend to think of it as all back slapping & palm pressing, golf and dinner, and all that jazz. Newsflash - It’s not that entertaining. If you’re not travelling on a Monday morning (and even if you are) there’s usually “team” meetings coming up. You know the ones - where a cast of thousands want to review your pipeline and provide sage advice from their years of meaningful experience in development, or marketing, or HR or finance, or law or janitorial services – you know lots of useful (less) sources. Or there’s other team planning, deal meetings, and God forbid you have client/prospect calls to plan for.


The problem with this approach – proactive planning for the week - was that it took time. In fact you could spend all weekend planning the following week, and by the time you were done with the planning it was Sunday night already! Without being a bore, the era of artificial intelligence is able to better equip you and really deliver on the idea of working smarter NOT harder.


In spite of my trying to avoid being self-serving here – there are lots of emerging ideas and tools in the Sales sidekick category of ai. Whether you use ours is not really the point here – but our tool (and I’m sure some others) will literally save you hours and frankly do a better job with research, insights, thought provocation, preparation, strategy identification and helping you create plans, strategies, tactics & find answers, so you’re better prepared, faster and with less effort for the roller coaster ride of the following week!


Final thought – sales is obviously not the only “world” out there – but it’s what we deal with. There’s lots of jobs where you suffer the Sunday Scaries, and you can plan your way out of all of those just as well. What you shouldn’t do is kick the “Monday Morning” can down the road into Sunday night. One of the things we dread, whether is Sunday night or not, is being unprepared. Who doesn’t, or hasn’t, suffered the dream of showing up for an exam to realize you know nothing about the subject…plus you may, or may not, be wearing any clothes! Having a considered plan that we feel good about can take hours, if not days to formulate, and it can cloud your mind when you’re trying to enjoy your weekend. In the case of sales, whether it’s an account plan, a territory plan, or a reactive plan to changes in a sales pursuit, they are challenging and time consuming. With the selective use of a.i., the cliché of “working smarter, not harder” might actually be achievable.  

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Updated: Jun 18


Imagine a seller we'll call Jack. Jack just sat through a week-long sales boot camp (in person or otherwise) – in person or even worse on seemingly endless, soul destroying (but cheap) zoom calls. By Friday, his brain is like a sponge that's been left under a running faucet—dripping with excess information and incapable of soaking up another drop. Jack, like so many in his field, is a victim not just of bad timing in training, but also of the corporate belief that when it comes to training, more is always better. Spoiler alert: It's not.


When Just-in-Time Beats Just-in-Case

Traditional sales training operates on a "just-in-case" model. It's the equivalent of learning how to fix a tire before you even know how to drive—sure, it might come in handy someday, but by the time you need it, you'll probably have forgotten which tool does what. Contrast this with the "just-in-time" model, which is like having a mechanic show you the ropes when you're roadside with a flat. This method ensures that learning is immediately relevant and applicable.


The benefits of just-in-time learning aren't just anecdotal. The Forgetting Curve—a concept first introduced by psychologist Hermann Ebbinghaus—demonstrates that without reinforcement, we start losing the memory of learned knowledge in a matter of days. In fact, research suggests that within one hour, people will have forgotten an average of 50 percent of the information presented. Within 24 hours, this number rises to 70 percent, and if a week passes without that knowledge being applied, up to 90 percent could be lost. That’s not just a curve; it’s a cliff.


Imagine we plot Jack's training retention on a graph. It wouldn't be a slow, gentle slope but a steep dive, like a rollercoaster when you've just reached the peak and are bracing for the drop. Now, that’s the type of adrenaline rush you want your sales team to avoid - right?


Cognitive Overload: When More is Less

Then there’s the information overload. It’s the age of big data, but bigger isn't always better, especially when it comes to learning. Cognitive load theory tells us that our working memory has limits. Bombard it with too much information, and you'll jam the gears. Sales training is full of too much information, and crammed with complexity.


In our age of multitasking myths, cognitive overload is the supervillain. It swoops in when we pile up the sales techniques, sales methods, strategies & tactics, industry insights, political know-how, psychology, neuroscience, expecting sellers (veterans, rookies & everyone in-between) to switch gears at lightning speed. But here's the kicker: A study published in the journal 'Computers in Human Behavior' found that participants who multitasked during cognitive tasks experienced significant performance drops. In terms of sales training, this means that the more we dump on our trainees at once, the less they’re actually learning. It's like expecting Jack to learn to juggle while riding a unicycle. Entertaining, yes. Effective? Not so much. And as our window of opportunity to spend time with prospects continues to close – we have to be at our best when these opportunities present. 

 

It's complicated…and expensive

There's a peculiar badge of honor that sales training seems to pursue—complexity. Somewhere along the line, we started to measure the effectiveness of a training program by how intricate it could become. Instead of sticking to the core principles of sales we've entangled the process with a labyrinth of techniques, acronyms, and processes and the modern affliction of “cleverness.” This convoluted approach may have succeeded in making sales training seem like an arcane art only accessible to the few with a Rosetta Stone, but in reality, it has done a disservice to many sales professionals. They're often left with a toolbox so overstocked and disorganized it's nearly impossible to find the right tool when the moment of truth arrives in front of a prospect. Simplicity is the soul of efficiency, but sales training has forgotten this, opting instead for a complex system where more is less.


The sales training response to this has been the deployment of the “invaluable” “deal coach.” This is a  more recent phenomenon (compared to the much older one of getting bent over by the sales method & training experts). This is where company leaders seem to admit that they are unwilling or incapable of quarterbacking their sellers through more convoluted deals, and bring in expensive, fraudulent “experts” – deal coaches. Once again the actions of the leadership come into question. Clearly the question should then be “well if you can’t guide & coach your team through the more challenging deal cycles and sales motions (another fabulous BS phrase), what are you doing?”


Shining the light

So, what’s the takeaway? The old approach to sales training needs to be put out to pasture. And this idea of needing the modern version (the deal coach) is an admission of defeat.

Instead, it's time to accept the weaknesses of training & take a new approach. —use targeted, timely, readiness thinking, ideas and tools. Provision advice, insights and ideas as close to the prospect engagement point as possible, getting  sellers better prepared, faster and with less effort. Let's give Jack and his colleagues what they need when they need it, so that information is a tool they use, not a flood they feel will drown them.

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Updated: Sep 17




Introduction As this year winds down, we’re all prone to contemplate the coming year.  Some things will change, some won’t. One of the latter being how companies are increasingly looking towards roles traditionally not associated with revenue generation, such as Project Managers and service delivery professionals, to contribute to sales targets. This shift raises important questions about the implications for these professionals.


The 'Why' Behind the Trend Two primary factors are driving this trend. Firstly, ever present cost savings – by leveraging existing staff in revenue-generation roles, companies can potentially reduce the need for a larger sales force. Secondly, there's always been a healthy sentiment of skepticism towards traditional sales roles in the consulting and technical services fields. There's a perception that non-sales (service & delivery) professionals, offer more subject matter expertise and an authentic and less 'salesy' approach to clients, due to their intimacy with the product, service, or industry.

The Argument Against Expecting non-revenue staff to take on sales responsibilities can be seen as unfair for several reasons:


  1. Skill Mismatch: These individuals are hired for their expertise in areas other than sales. Asking them to perform tasks they weren't trained for can lead to stress and job dissatisfaction.

  2. Divided Attention: Their primary role, which is crucial to the business, will suffer if they are also focusing on revenue generation.

  3. Potential Conflict of Interest: A project manager's goal is to deliver the project efficiently, which might conflict with the aim of maximizing revenue.


The Argument For Conversely, involving these professionals in sales makes sense due to:


  1. Deep Domain Knowledge: They often have a better understanding of the product, service, and the associated resources skills and tasks which can translate into more natural selling.

  2. Established Client Relationships: Their existing relationships with clients inspires more organic and trusted sales interactions.

  3. Business Acumen: Their supposed understanding of the business can enable them to identify and exploit revenue-generating opportunities that pure sales roles might miss.


The Gap in Sales Skills The crux of the issue is that while these professionals have the potential to contribute to revenue generation, they typically lack sales “know how”. While that know how might not be magic, it plays a role. You can try to bridge the gap by implementing sales training for this group, providing more tools and resources and orchestrating greater collaboration across the organization. The first and third alternatives here have been done before. The first, training, has been done to death with limited success. Obviously, people look at technology these days, but not just technology in its broadest sense - but artificial intelligence of course!


Leveraging Technology to Bridge the Gap In the era of a.i. traditional approaches to equipping non-sales staff with sales skills are no longer the only, or preferred, solution. AI-powered sales coaching tools can help in several ways. Currently, these tend to be focused on areas like Automated Lead Scoring and Qualification, Predictive Sales Analytics, Sales Assistance and Customized Learning Paths.


AI-powered sales enablement tools: There’s a bunch of labels emerging, or being re-used, to categorize this collection of tools and software products: sales enablement, sales readiness, sales effectiveness - AI sales coaching tools, AI-powered sales readiness software and AI-powered sales enablement. This space will get more crowded and noisier. Companies big and small are already appointing people to look at a.i. We’ll see more companies using a.i. as the first lens they look through as they contemplate their strategies. When it comes to a.i. for sellers, company leaders need to firstly decide what their view of sellers and the selling world really is, and what role does it play in their business. Then they can tool up accordingly.


This is particularly relevant to those leaders of services companies – consulting, professional services, technology consulting, etc. These companies have demonstrated indifference to the need for sellers but not the need for revenue! Hence, they park that problem with the partners and service delivery leaders. Often, when they do recruit dedicated sales teams, the support provided is weak – no training, little support, no respect – “figure it out yourselves, that’s why we hired you” type of attitude and a smirk when it fails. But the wringing of hands and gnashing of teeth continues. It’s ok to decide sales teams are not your answer while remembering that revenue always is! If this is the case, then you have to sales enable your “non-sellers” accordingly.


Sales training isn’t the answer. It’s overcomplicated, clumsy, and poorly delivered. AI-powered sales coaching tools are a more promising area – sales co-pilots and sidekicks. This technology can significantly bolster the capabilities of non-sales professionals in revenue-generating roles. It can deliver at, or just before, the point of prospect engagement (not three months ago), thereby maximizing retention, while allowing people to maintain a sense of autonomy and self-reliance.


Conclusion As businesses continue to blur the lines between sales and non-sales roles, the key to success lies in empowering all these professionals better. Relieve the burden of sales leaders with the right tools to help revenue generators attain situational fluency. In an age where a.i. and technology are more capable than ever, it's possible to plug any sales skill gap, and elevate performance in innovative and efficient ways. This approach not only leverages the unique strengths of non-sales staff but also ensures that the core quality of service delivery remains uncompromised, and sales behaviors become more intentional and consistent.  Ultimately, it's about admitting your opinions and confronting the weaknesses (even if it looks unfashionable to do this) and thereby finding the balance required for more serenity in sales! 


Happy Holidays from us at ShadowSellerai.

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