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This sales podcast episode is on the fundamentals of sales leadership with focus on behavioural change and sales coaching. I have taken the transcript from the sales podcast episode and am providing it below with minimal formatting or grammatical changes. It’s rather conversational but I’m providing it to those of you who prefer to read or want to highlight specific statements. It’s based upon the lessons I have accumulated working with sales organizations and delivering leadership training programs over the past 20+ years. Following is the full video version of this Podcast and below that is the transcript:
Here’s the transcript:
I’m shifting to both video and audio, so you’ll be able to find the video of this podcast on YouTube. But I’m also going to be sharing those on my Sales Academy website as well. You can find that at Salesacademy.ca.
So, my goal, of course, is to take this content I’m creating in my podcast and distribute it further and in different mediums depending on how you like to learn. I’m also going to be throwing these onto my Instagram channel @ShaneGibson and my TikTok channel @ShaneGibsonLive if you want to access this content in sound bites versus a long podcast.
Today, I’ll be focusing on the fundamentals of leadership sales coaching, particularly the coaching process tailored for sales leaders. Now, if you’re a salesperson listening to this and you start to check the boxes around what your leader isn’t doing for you, this is really not what it’s about. In no organization is the coaching process perfect. It’s constantly evolving. And sometimes, as a salesperson, you have to step up to the plate and proactively seek that coaching from your peers and your sales leader in your organization. By no means is this meant to be an exhaustive list of criteria you should use to judge whether your leader is any good, but rather an indication of what gaps exist in your organization and where you might need to seek help. And of course, for sales leaders, I’m hoping this gives you a foundation to build upon, so you can have a more solid process in your sales coaching.
Let’s talk about leadership in general, particularly in behavioral training for sales teams. Sales leadership, first and foremost, is all about driving results. And at the end of the day, driving results is often about behavioral change. So, as a sales leader, the better you become at sales leadership, the better you really are at driving behavioral change, whether it’s in your leaders, if you’re managing a group of sales managers, or your direct line salespeople, if you’re a sales manager yourself. Leadership truly builds people who then build the business. That’s the real core. Leadership also fosters innovation, accountability, momentum, and organizational growth. One of the most powerful parts of leadership is the coaching skill set—the ability to develop people. By integrating behavioral training for sales teams, sales leaders can better inspire and cultivate the skills and behaviors necessary for sustained success.
With that said, I also know great leaders and great coaches who fail to meet their potential or sustain their organizational growth and success because they lack management skills. A great sales leader is one part coach, one part manager, and, I would argue, one part CTO or Chief Technology Officer. But we’ll delve into that at another time. Today, our focus is on coaching.
Before we delve deeper, let’s consider management skills. Managers maintain systems that sustain the vision. They create systems that grow that vision, and they manage both people and processes. Great managers are often excellent communicators, and they excel at developing systems and processes. It’s also about accountability. Thus, effective managers often have robust systems in place and demonstrate habits and disciplines centered on accountability. They are acutely aware of return on investment and adeptly organize their efforts around their goals. They also bring stability, credibility, and consistency to the table.
It’s not just enough to be a visionary leader or an exceptional coach; one must also develop these fundamental management skills. Many of us, having transitioned from Salesperson to Sales Manager, then to Director of Sales and eventually VP of Sales, might have bypassed these traditional management skills. We might rely heavily on our ability to sell and inspire others. But there’s a threshold we’ll inevitably hit unless we commit to a more systematic approach to sales leadership.
In my opinion, a significant portion of success in sales, as mentioned earlier, revolves around facilitating both behavioral and organizational change, primarily because we always need to address and adjust to the dynamics of the marketplace. And if we’re going to effectively communicate our vision, we should remember that understanding the ‘why’ comprises 90% of achieving any goal.
90% of getting your salespeople to shift their behaviors, habits, or to implement new disciplines or processes is often about effectively communicating the “why.” When we communicate our vision, I think the first step is asking, “Is it SMART?” Of course, SMART means Specific, Measurable, Attainable, Realistic, and Timely. However, what’s missing in the SMART acronym? It also has to be contextual. How do I relate what’s beneficial for the salesperson with the impact it has on the organization and the significance of the team overall?
To succeed merely because “upper management wants it” isn’t enough. We truly need to understand, inspire, communicate, and contextualize significant shifts in the organization. Are you, as a leader, inspired by it? If you’re going to communicate your organizational sales vision or a major goal or initiative, you are the first person that needs to buy into it. Have you linked it to their individual needs? And is it easy to understand? A famous quote suggests that if it’s too complicated to explain, it’s too challenging to implement. If you can’t explain it succinctly, you probably don’t understand the topic well enough.
So, when I’m communicating a sales vision or goal, I aim to contextualize it in such a way that I can rally my team around it. If my communication feels top-down and isn’t tied to their values or the overarching “why” for them or their team, I’ve missed the mark. I won’t get buy-in from the team.
Now, let’s talk about coaching. This is one of the fundamental tools I’ll use to communicate vision and induce behavioral change. It’s intriguing how many sales leaders claim they are “too busy” for coaching. In my opinion, they’re not too busy; they’ve simply deprioritized it. They would never skip a meeting with their company’s CEO, yet many often neglect or postpone scheduled one-on-ones with their sales team.
A healthy sales organization’s key performance indicator suggests that the sales leader doesn’t just check numbers and projections but also conducts meaningful one-on-one developmental meetings. I challenge many sales leaders to move beyond coaching to a spreadsheet or dashboard. That’s not coaching; that’s ensuring compliance. Instead, focus on generative coaching which involves skill development and specific deal insights.
Coaching should align with the process. Successful sales coaching emphasizes the qualitative aspects of your key performance indicators. For instance, the quantitative aspect of a discovery call might involve asking seven key questions. The qualitative aspect, however, focuses on the manner of questioning, depth of understanding, and efficient note-taking. By integrating these qualitative aspects, we can offer a structured learning regimen to the whole team.
Sales scorecards and a corresponding sales playbook can help. By documenting best practices and scoring each step, we can produce projections based on how well the sales team executes these steps. Being formal is vital. Drawing a parallel with martial arts, I’ve realized that just as training requires regimented processes and timed check-ins, so does sales coaching.
My martial arts mentor, Fred Shadian, taught me this importance. Fred Shadian actually lives on Saturna Island. No matter how you look at it, it takes about 5 hours to reach him from my home, involving a couple of ferries, some driving, and other logistics. Because of this, we started doing Zoom check-ins. These are at a specific time each week. I have a series of specific activities I undertake, which he evaluates, measures, and coaches me on.
The combination of accountability and structured practice with specific exercises in a short period has refreshed and sharpened my skills. I had been pondering the idea for a while and practiced sporadically on my own for several months. But the moment I incorporated structure and accountability, I noticed improvements in my skills, awareness, and other aspects. My confidence also increased due to a consistent feedback loop. Good sales coaching operates similarly. As sales leaders, we need to prioritize formality.
One thing worth mentioning is the SalesAcademy,ca sales coach assessment. If you go to Salesacademy.ca/Salescoachassessment, there’s a downloadable PDF available for free. This document allows you to evaluate your sales coaching skills and the processes of your organization to identify areas needing improvement.
It’s also worth noting that as salespeople, and even entrepreneurs, begin to reap the benefits of coaching, they often attribute all the success to themselves. They may neglect the behavioral shifts brought about by the coaching. Hence, as a leader, it’s crucial to summarize the impacts of the coaching sessions on their sales results. This isn’t about claiming credit but highlighting the value of the coaching relationship.
On the subject of coaching, it’s about inducing behavioral change. Trust is foundational. Questions of credibility, integrity, and a proven track record in sales or sales leadership are paramount. Beyond this, the sales team must feel that their leader supports them. If coaching isn’t systematic, you’ll struggle to maintain momentum. Establishing routines, utilizing assessments, employing forms, maintaining credibility, and setting a consistent cadence are pivotal to the success of your coaching endeavors.
Being an effective coach means:
In essence, while the process and business side of sales is vital, personal aspects like mindset, empathy, and personal challenges equally impact performance. A skilled sales coach comprehends this duality and acts accordingly.
Now, not saying you need to be a therapist, but there are times when issues arise that are beyond our competency set. In such instances, referring someone to professional help might be the best course of action. However, at the bare minimum, we should be good listeners, exhibit empathy, and provide constructive feedback.
Unfortunately, I can’t delve into this deeply today, as this podcast episode is already jam-packed. That said, “Radical Candor” is an insightful book on delivering direct and effective feedback. Both leaders and their teams can benefit from its teachings. If everyone agrees to approach each other with candor and empathy, trust and transparency will thrive. Effective feedback fosters an environment where individuals can be both vulnerable and direct, eliminating the fear of treading on eggshells or suppressing feelings and thoughts.
Starting with a Benchmark: Begin with an assessment, plan, or benchmark. A strategic sales plan for the year or quarter is an ideal starting point. Incorporate a mindset plan, assessing aspects like confidence, personal development, communication skills, empathy, and emotional intelligence. Determine developmental goals for the next 6 to 12 months.
Understanding Connection: Every individual is unique. Recognizing their learning style, personality profile, motivators, and energy drainers is essential. This insight will allow the coaching process to adapt to each individual’s specific needs.
Setting Clear Criteria: Coaching must be goal-oriented, aiming to make impactful shifts both personally and professionally. Short-term objectives should hone in on specific competencies, attitudes, or behaviors.
Having a Structured Timeline: Regularly scheduled monthly coaching sessions, punctuated by laser-focused coaching sessions, can make a difference. These sessions delve deep into major challenges and also provide quick tactical solutions.
Using a Formal Process: Implement templates for feedback and tracking progress.
Contrary to what many believe, coaching isn’t just doling out advice based on personal experiences. Rather, it’s about molding someone’s thought process, shifting their perspective. The art of questioning plays a pivotal role here. While it’s impossible to run through all the valuable questions in one session, introducing a few of these during coaching can induce profound shifts in a salesperson’s mindset.
These questions are a mix of tactical and strategic inquiries aimed at understanding, guiding, and assisting salespeople in their roles.These, among many others, can become instrumental in steering conversations towards growth and development.
An essential point of discussion is the idea of being coachable. Dr. Denis Cauvier, author of “Coachable,” stresses the importance of leaders being open to coaching themselves. If a leader isn’t growing or evolving, it seeps into the team’s morale and productivity. Leaders should continually seek out new learning opportunities, mentors, and coaches, ensuring they remain relevant and valuable to their teams.
This has been Shane Gibson’s podcast from closingbigger.net. [end sales podcast transcript]
The post Top 40 Sales Coaching Questions – leading behavioural change through coaching and powerful questions appeared first on Shane Gibson's Podcast – AI and Digital Selling – B2B Sales and Influence.
This podcast episode is focused on sales leadership. As a sales leader, whether we are a CSO, VP of Sales or frontline Sales Manager – we want A-level results from our sales teams.
You can’t get A-level results with C & D players on your team. You need a team full of A-level players or players that are willing to pay the price to become an A.
It’s my belief that we can talk about A-level goals and exceeded targets but if we tolerate C and D level mindsets and behaviours it will erode the momentum and sales productivity of the entire team.
In this sales leadership podcast I dive into how to segment your sales team and where to invest your time. I also dig into when you want to move people up, across or out QUICKLY.
Identifying the Players:
A Players: The Absolute Performers A players represent the top 20% of your team, contributing to 80% of the sales results and energy within the organization. These individuals possess a growth mindset, are eager to develop personally and professionally, and understand the importance of teamwork. They strive for more than just closing deals; they seek to contribute to something larger, making them invaluable assets to your team.
B Players: The Beneficial Team Members B players are open, aware, and show significant potential for growth. They may face challenges such as lack of confidence, newness to the market, or a need for skill development, but they are receptive to growth and improvement. Investing in B players can yield substantial returns as they have the potential to ascend to A player status with the right guidance and support.
C Players: The Convenient Players C players tend to be complacent, content with their current status, and lack the desire to grow. They may not actively harm the team’s performance, but they do not contribute to innovation or energy either. For C players, the choice is clear: grow or go. As a leader, it is crucial to help them make this decision swiftly to maintain team momentum.
D Players: The Disengaged Sales Team Members D players are in urgent need of change; they either need to adjust their attitude and performance quickly or exit the team. Their negative impact can erode team morale and drain energy from leaders that could be better invested in A and B players. Swift action is required to address the issues posed by D players to preserve the team’s integrity and performance.
Understanding the different types of players in your sales team is crucial for effective team management and success. By identifying and investing in A and B players, addressing the issues posed by C players, and swiftly dealing with D players, you can create a high-performing, motivated, and energetic sales team. Remember, the key is not just to manage but to lead and inspire your team towards growth and excellence. This also means making the hard decisions to protect your A’s and B’s from being pulled down by a C or D level sales culture.
The post Sales Leadership Podcast: Building A High Performing Sales “A-Team” appeared first on Shane Gibson's Podcast – AI and Digital Selling – B2B Sales and Influence.
A good sales kick-off should do more than energize the room for a day. It should help the sales team reset priorities, understand the market, sharpen their daily disciplines, and leave with a practical plan to grow pipeline.
As a sales kick-off speaker and B2B sales trainer, I get to see how sales organizations are thinking as they prepare for a new year, a new quarter, or a new growth mandate. The best teams are not looking for motivation alone. They are looking for alignment, resilience, better business acumen, and a repeatable plan for execution.
Sales success this year is not going to look exactly like last year. Buyers are more cautious. Decision-making groups are more complex. Competitive pressure is high. Even when the market is strong, your competitors may be acting as though it is harder — and that changes the playing field.
Tough and competitive markets are when great salespeople and great sales cultures are built. The companies that win are the ones that take disciplined action while others wait for conditions to improve.
Here are nine B2B sales kick-off strategies to help your team build momentum and execute with more consistency.
Following is my outline covering the key points in this B2B Sales Podcast:
This includes knowing why people leave suppliers and scan the market for:
Tell stories using video, most industries don’t have a well known salesperson that is building a brand using short-form video such as TikTok’s, Reels, and Shorts. These videos also get a lot of engagement on LinkedIn. Short-form video can include:
Advice
Events
Personal stories
Educate yourself on your clients
Know the regions and markets
Know your own solutions, applications, history, limitations, and the future direction. What vision would your CEO or CMO paint for the company. Get good at telling that story.
These 9 things you can focus on to make sure your B2B Sales efforts are successful in the coming year. If you’re looking for a sales keynote speaker or sales training for your team you can reach Shane Gibson at [email protected].
A VP of Sales should look for a speaker who can connect the company’s growth strategy to practical sales behaviours. Motivation matters, but it is not enough. The speaker should understand B2B selling, pipeline pressure, complex buying committees, account growth, outbound discipline, and the realities of leading a team through change.
Start with the business outcome. Decide whether the priority is pipeline creation, account expansion, sales discipline, resilience, business acumen, or sales culture. Then build the keynote and agenda around one or two core behaviours the team must execute after the event.
Strong themes include disciplined growth, winning in a tougher market, building resilient sales teams, expanding strategic accounts, improving business acumen, sharpening outbound execution, and becoming more relevant to executive buyers. The best theme should match the actual market conditions your team is facing.
Involve the speaker once the leadership team has defined the business objectives for the event. A good speaker can help shape the message, identify gaps in the agenda, and align the keynote with the sales leader’s priorities. Waiting until the agenda is already locked can limit the impact.
Share the team’s goals, sales challenges, market conditions, buyer objections, pipeline issues, competitive pressures, sales process, strategic priorities, and the behaviours leadership wants reinforced. The more context the speaker has, the more relevant the keynote will be.
Experienced salespeople respond to speakers who understand the field, not just the stage. Credibility comes from practical insight, real-world examples, clear business language, and respect for the pressure salespeople face. A credible speaker challenges the team without talking down to them.
Yes, when the goal is behaviour change. A keynote creates alignment, urgency, and shared language. Sales training allows the team to practise, apply, and personalize the ideas. Many organizations benefit from pairing a keynote with a workshop, breakout session, sales manager session, or post-event reinforcement.
A sales kick-off can support pipeline growth by resetting expectations around prospecting, lead nurturing, account targeting, trigger-event monitoring, and outbound activity. The event should help salespeople identify where new opportunities will come from and what daily actions are required to create them.
Sales managers should turn the event message into coaching conversations, pipeline reviews, team meetings, and activity standards. If the keynote focused on outbound discipline, managers should inspect outbound activity. If it focused on business acumen, managers should coach stronger account research and better pre-call planning.
Do not measure success only by audience feedback. Stronger indicators include improved clarity around sales priorities, manager adoption of the message, increased prospecting activity, better account planning, stronger pipeline conversations, and visible behaviour change in the weeks after the event.
The post 9 B2B Sales Kick-Off Strategies – Keynote Sales Speaker Shane Gibson appeared first on Shane Gibson's Podcast – AI and Digital Selling – B2B Sales and Influence.
This podcast was inspired by a sales troll on TikTok. I posted a TikTok video on “Why sales is not like dating.” The response was 99.5% positive but there’s always one guy out there. His response was “Sales is like dating …. value-based selling is weak.” This got me to think of this analogy and why it’s so popular and also how sales and expectations of salespeople have changed significantly.
In this sales podcast I dig into how much sales has moved from a “skill set” to a true profession, one where today you can even become a certified sales professional.
True sales professionals are no longer about tactics and explaining the value of their product. The sales professional today knows they need to partner with their clients to create value. It’s a collaborative process and in many cases the customer knows just as much about the topic as we do.
Here’s the original TikTok Sales Video:
The post Sales Podcast: Moving from Extraction to Collaboration Based Selling appeared first on Shane Gibson's Podcast – AI and Digital Selling – B2B Sales and Influence.
This sales podcast episode is focused on shifting our mindset to one that drives sales success. Sales process only works as well as the mindset of the person using it.
Unproductive mindsets are often what is holding back exceptional people from reaching their true potential. Developing an empowered mindset can you produce greater results, consistently.
Here’s a list of common negative sales mindsets and a set of empowered mindsets that can help you take your sales career to the next level:
The post Sales Podcast: 10 Mindsets for Sales Success appeared first on Shane Gibson's Podcast – AI and Digital Selling – B2B Sales and Influence.
This sales podcast episode is focused on how B2B sellers can plug the most common holes in their sales pipeline. When I am working with sales teams part of my sales training and sales enablement process involves getting out in the field and helping individual salespeople build their sales strategy. I often hear people make statements such as:
I don’t understand why deals aren’t closing, I haven’t changed my approach!?
People just aren’t getting back to me, they were excited but now they have disappeared.
Many of my projected deals aren’t going to close this quarter like I thought they would.
I have a lot of new deals stuck at the proposal evaluation stage.
The client is going to buy but the order is going to be much smaller.
Do any of these sales pipeline pains sound familiar?
In this B2B sales podcast I cover 7 common reasons why opportunities get stuck or die prematurely and key strategies we can deploy to breath life into your sales pipeline.
In the podcast we discuss these challenges and how sales professionals can overcome them preemptively.
The post B2B Sales Podcast – 7 Big Sales Pipeline Challenges and How to Fix Them appeared first on Shane Gibson's Podcast – AI and Digital Selling – B2B Sales and Influence.
Today’s sales podcast is on how discipline is the secret ingredient to massive sales success. Why I call it a secret is it’s not obvious to a lot of people that what they’re missing isn’t sales process, methodology, tactics or luck… it’s the lack daily disciplines that is holding them back from massive sales success.
Jay Conrad Levinson author of the Guerrilla Marketing series of books said this about consistency:
“Mediocre done consistently beats brilliant done once every time.”
When I am delivering my sales training or sales keynotes I find many people are excited to learn what’s new in the world of sales success, only to be surprised to learn that they already “know” the best practices. What most need to do to improve their success is simply be more consistent with their best practices in sales.
The post Sales Podcast: Daily Disciplines for Massive Sales Success appeared first on Shane Gibson's Podcast – AI and Digital Selling – B2B Sales and Influence.
Selling to senior decision makers or the “C-Suite” requires that we truly understand how our solution can impact their business. Not only that but we need to understand how we do it in a unique way that adds value over and above what competitive solutions do. Everything from our first conversation, to discovery calls, presentations, proposals and delivery needs to highlight how you’re driving positive outcomes in a unique and advantageous way.
Senior executives and business decision makers are results-orientated. Both tangible results and intangible results appeal to them. In order to be seen as a resource and potential supplier you must tap into their desire to produce results.
Show them how their overall volume can be increased; in other words, an increase in sales.
If they see that their employees, or their equipment, or other capital will be more efficient, then the chance of their buy-in is higher.
Top level decision makers are the ones who have to answer to the Board of Directors and to the Shareholders in a large corporation. Keeping the Board or shareholders happy is their main priority.
Lowering costs equal better margins and bigger profits. There’s many ways our solutions can do this directly and indirectly.
They are interested in advertising, marketing and business development strategies, tactics and methods to increase market share.
Can you show them how they will get a bigger return on their investment for the money they invest with your services, products, ideas and concepts?
If you come with solutions for market changes that affect them, then they will take the time to explore the possibilities with you.
The types of intangible results that appeal to top level decision makers are:
Anything that you can do to lower or eliminate the risk makes them feel better.
Senior executives and top level decision makers are at the top because they have personal pride and are proud of the business results that they achieve.
Yes the car they drive reflects their success level. The suits, the shoes they wear, the house they live in, the office address, and the image their marketing material portrays are all examples of personal and/or corporate image.
One could argue that these are tangible, there is a lot of data that shows that organizations that embrace these types of initiatives have lower staff attrition, more corporate goodwill, and have access to opportunities that organizations that score lowly in these areas can’t access. Are there ESG an EDI advantages and benefits to using your solution or partnering with your company?
The top level decision maker knows that you win when you have exceptional people working with you.
This is by no means an exhaustive list but I hope it gets you started. The key is for you to understand at a forensic level the top challenges and goals of your key prospects and accounts and how you can effectively and uniquely solve them – then put that into terms that resonate with their specific values, perspective and context.
*IMPORTANT NOTE: Don’t present outcomes and solutions generically, use your one-on-one conversations and research to customize your value proposition.
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The post Sales Podcast: Selling to C-Level and Senior B2B Decision Makers appeared first on Shane Gibson's Podcast – AI and Digital Selling – B2B Sales and Influence.
Building an effective Sales Playbook for your organization is vital to your ability to scale and sustain your sales success. It’s your franchise success manual for your sales team.
There are many comprehensive and highly detailed guides out there on how to build a sales playbook, but I wanted to focus on a format that can get you started quickly.
In this podcast I cover the key components of an effective lean sales playbook. Here’s a quick list of what I cover:
Each can be less than a page or can include everything from in-depth sequence information to product case studies. I would suggest starting lean and keeping each section down to one page, if possible, the playbook doesn’t have to include every piece of information on your sales process and tools BUT it should tell them where to find the information and how they will be measured.
This document can also be a great framework for your sales onboarding process, as it provides a checklist or road map of what they need to learn to effectively execute their role.
For sales managers, leaders and coaches the Sales Playbook becomes a reference guide and coaching tool. We want to train or team over time to refer to the playbook and self-assess using the score card before coming to us with a sales challenge.
In many cases I have found that building the habit of self-reflection helps salespeople get more out of their coaching sessions and builds the discipline of self-directed learning and improvement. Yes, we want them to come to us for help but we also want them to take ownership and self-direct and adjust as much as possible. The sales manager and sales leader should direct and lead not be a walking sales encyclopedia, our job is tell people where to look not to give them all the answers.
Playbooks don’t replace coaching or training. They also don’t replace job shadowing or peer mentoring. Their role is document and define best practices and processes and give the sales team a true understanding of what they need to get good at to succeed.
If you’re looking for consulting, training or Sales Playbook development visit SalesAcademy.ca
The post Sales Podcast: How to Build a Lean Sales Playbook appeared first on Shane Gibson's Podcast – AI and Digital Selling – B2B Sales and Influence.
This podcast is based upon my recent digital-reinvention keynote for the World Trade Center Vancouver’s export awards. I had a number of attendees want my notes and slides and I thought a better way to share them is through my social selling and influence podcast!
In this podcast we discuss:
Following is my slide deck (Click on the image to download)
The post Digital Sales Podcast – Growing Your Business in a Digital-First Economy appeared first on Shane Gibson's Podcast – AI and Digital Selling – B2B Sales and Influence.
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