Episode 499: The Sales Reset: Aligning Strategy, Mindset & Execution for Real Results

Wesleyne Whittaker [00:00]: When I hear making sales social, it reminds me that sales is human-to-human selling. I am a human and I am selling to another human. And so I think a lot of times, especially in this digital world, we remove the human element.

Bob Woods [00:14]: Welcome to the Making Sales Social podcast featuring the top voices in sales, marketing, and business. Join Brynne Tillman, Stan Robinson Jr., and me, Bob Woods, as we each bring you the best tips and strategies our guests are teaching and using so you can leverage them for your own virtual and social selling.

Brynne Tillman [00:35]: Welcome to the show. Welcome back to Making Sales Social. I have an incredibly special guest today, someone that I have known in real life for years and is now leading women sales experts, Wesleyne Whittaker. She is the founder of Transformed Sales and the author of The Sales Reset, the framework CEOs use to drive consistent sales execution. Wesleyne works with CEOs who are frustrated by inconsistent sales performance, leadership turnover, and pipeline meetings that feel more like guesswork than strategy. While many organizations assume their issue is talent, Wesleyne helps them uncover the real problem: misalignment between leadership systems and execution.

Before launching Transformed Sales, Wesleyne built and led international sales teams, executed major business turnarounds, and drove measurable growth in complex technical environments. Today, she helps companies move forward from inconsistent results to structured execution where leaders lead teams that perform without constant micromanagement. I love this. Welcome to the show, Wesleyne. Thanks for being here.

Wesleyne Whittaker [01:48]: Thanks so much for having me, Brynne. I’m so excited.

Brynne Tillman [01:51]: So, just for the listeners to know, when COVID hit and I had to bring my entire company, as everyone did, online, Wesleyne… I’m like, we’re on a call and I’m like, “I don’t know where to start.” And I don’t know, we spent three hours and you downloaded my brain and came back with what is now my full entire business. So I just want to share that impact was enormous and now 70–80% of my business is what I shifted to during COVID. So, I just want to say how grateful I am and will always be appreciative of your brilliance. What I really loved was how you interviewed me and I was able to take all that mush that was going around my head 24/7 and then you and your team put it into a process—and this was before AI. So I like the fact it was just amazing. Thank you.

Okay. So before we jump into sharing your genius with everyone, we ask all of our guests the same first question, which is: what does making sales social mean to you?

Wesleyne Whittaker [03:12]: So for me, when I hear making sales social, it reminds me that sales is human-to-human selling. I am a human and I am selling to another human. And so I think a lot of times, especially in this digital world, we remove the human element and we don’t speak to someone like we would speak to them in person. So making sales social is all about the human-to-human interaction and how can I connect with you at that deeper level, below the surface, below what we just see online—just really having that human-to-human connection.

Brynne Tillman [03:45]: I love that. That’s perfect. All right. So I first want to start talking about your book, The Sales Reset. Your argument is that most sales problems are actually strategy problems. So talk to me a little bit about what led you to that conclusion and how that really inspired the “Belief Selling” methodology.

Wesleyne Whittaker [04:08]: Yeah. So, you know, I think one of the biggest things that I found after working with tons and tons of founders and salespeople is that we have a skills gap, but the skills gap is because we don’t have strategy. And so, we don’t know where we’re moving towards. We don’t have process built into anything. We don’t have accountability. And so, the output of that is lacking sales, inconsistent results, and not hitting quota. And so when I came up with the “Belief Selling” framework in my book… so the book is called The Sales Reset and we use the “Belief Selling” framework inside the book.

I really sat and I said, “Okay, so what is a thing that helps make people successful long term?” It’s the first thing that we have to do: we identify that there is a problem. And once we identify that there is a problem, we have to say, “I want to fix this problem. It is going to be hard to fix this problem.” Those are the first two steps in that framework. And then we move to learning skills. A lot of sales training or methodology that’s out there, we go straight tactical. We don’t think about the mindset gaps. We don’t think about the barriers. And so that’s why I find a lot of times what we’re doing in the sales world, it doesn’t stick because we aren’t addressing the things that are holding us back.

Brynne Tillman [13:40]: So I really love that. And then just for the record, say the name of the book again for everyone.

Wesleyne Whittaker [05:49]: It’s called The Sales Reset.

Brynne Tillman [05:51]: The Sales Reset. And I know I’m so excited to get to really read it. I got a sneak peek and it’s amazing. So talk a little bit about how leadership is going to use the framework in the book to really level the traditional sales training that is often missed.

Wesleyne Whittaker [06:12]: So “BELIEF” is an acronym for the steps that you need to walk through to really make true change in your organization. In the book, at the end of every single chapter, I have a section called “Belief Selling in Action” to show you how to use these steps for something like having better discovery calls.

“BELIEF” stands for:

• B is for Break Barriers, because you have to identify what is holding you back.
• E is for Embracing Growth, because growth is hard and nobody likes change.
• L is for Learning Skills, where we start learning the new things.
• I is for making a decision to Implement skills boldly. We’re going to try the scary thing, do the new skill, reach out to the person, and ask the funny question.
• E is for Execute consistently and practice. Just like elite athletes, they practice, practice, practice.
• F is for Fueling Others. We know the cycle of learning is complete when we can teach it to someone else.

Every single skill that I introduce, from prospecting to discovery calls to territory management, it all has that framework built in.

Brynne Tillman [07:51]: It’s brilliant. I love that. And I love a good acronym. So, you know, talk a little bit about how CEOs can tell the difference between a talent issue, a system issue, or an execution issue.

Wesleyne Whittaker [08:06]: So, I really think that you have to do a really good triage and ask yourself hard questions. Have I given this team a strategy that they can execute on with accountability, with key performance indicators (KPIs), and with deadlines? If your answer is no, then you start there and work on strategy. If you do have a strategy, the next thing you have to think about is: do I have a documented process for everything within this organization? How do we qualify leads? Is there a process to enter things into the CRM? If not, work on the process.

If you have strategy and process, then we go to people. If you have strong people but no process or strategy, they’re going to leave. Then you look at your people and you say, “Have I given them everything they need to succeed? Am I coaching them? Am I training them? Am I developing them?” That order is very important because if you start training and coaching people but they have no strategy and no process, it’s still going to fail.

Brynne Tillman [09:41]: I love that it’s linear because what happens often is you jump to what you think is “on fire.” But if you’re pouring in oxygen at the same time, that fire is not going out.

Wesleyne Whittaker [10:08]: Nope. And I think that a lot of times because as a CEO, there’s so many things, they’re like, “I have so many issues I should fix.” What is most important is to go deep instead of wide. Start and figure out where you can make the most impact. If you build out a sales strategy with accountabilities and KPIs, even if your people aren’t trained and don’t have a process, they now know what they’re striving towards.

I worked with a client recently who wanted to triple revenue in the next 10 years. I asked how he wanted to grow it: by building out existing accounts, by acquisition, or by going after new business. He said, “I want all three, Wesleyne.” We all do, but we have to start somewhere. If we do all three at one time, I call it “random acts of selling” because we’re just randomly doing everything.

Brynne Tillman [11:31]: I use “random acts of social” all the time, so I love that. So, I’ve heard you talk about how you evaluate teams across 21 core competencies. What are the most common gaps you uncover?

Wesleyne Whittaker [11:51]: I like to break those 21 core competencies into soft skills and hard skills (tactical skills). Oftentimes someone is strong in tactical areas but their intangibles are weak. Some of those intangibles include not being comfortable discussing money, not being motivated, or having a negative outlook on the organization. If those things aren’t there, it doesn’t matter how well they can hunt; they won’t do it.

Organizations focus so much on tactical skills like prospecting, closing, and qualification, but we don’t realize what is actually flowing into that. When I go in, I tell the organization we’re going to work on a soft skill and a tactical skill at the same time for long-term change. Otherwise, you teach them how to qualify and they’ll do it for a few months, but then self-limiting beliefs will make them stop.

Brynne Tillman [13:30]: That’s really powerful. So how does mindset consistently affect sales execution? And how can a leader identify that, since there’s no KPI for it?

Wesleyne Whittaker [14:14]: A self-limiting belief is a “wall” you have up about yourself personally or professionally. One area we assess is “sales posturing”—how I perceive myself as a salesperson. If I don’t feel like a good salesperson, a client can see that lack of confidence. I might be passive, avoid eye contact, or mumble.

Key things leaders can do: get out and actually do sales calls with your salespeople. Join as an observer, not to take over. Pay attention to non-verbal signals: where do their eyes go? What’s the cadence of their voice? How are they dressed? It tells you what someone is struggling with. Then, as a leader, you can say, “I noticed some things and I want to see if we can come up with a plan to help you improve.”

A lot of times leaders don’t want to dive into these things, but you must because there is something behind it. Maybe that person is going through a divorce and finding it hard to get out of bed. As a leader, you help figure out how to move them to where they need to be. This directly impacts how they sell and, in turn, your numbers.

Brynne Tillman [14:40]: I’m not sure leaders recognize how personal lives affecting professional lives can cause a lot of misalignment. If a leader identifies they are misaligned with their team, how is that showing up in pipeline and forecasting?

Wesleyne Whittaker [15:33]: I call it “irregular funnels.” A funnel should look like a funnel—more at the top than the bottom.

• Cylinder Funnel: Straight up and down. Close rates are near 100%. This person is not going after risky enough business, possibly due to a fear of rejection.
• Bloated Funnel: Really big in the middle. These salespeople “nurture to death.” They take you to coffee or golfing but never ask for the close. They are more focused on the “likability factor” than driving value.
• Inverted Funnel: A few leads at the top and a lot at the bottom. I call these “whale hunters.” They focus on a few big deals at a time, meaning they have tunnel vision. If those deals fall away, they have nothing.

If your job is to grow existing accounts, you should still be looking for new people or different business units within that organization. Otherwise, you risk a company pulling their business from you.

Brynne Tillman [18:30]: That’s a great visual. These were huge insights. Is there a question I should have asked you that I didn’t?

Wesleyne Whittaker [21:05]: The question would be: “What about me as a sales leader? What should I be doing?” As a leader grows, so does the team. I worked with a leader who was ready to demote himself because he was tired of leading and was on a performance improvement plan (PIP). I asked him, “What are you running away from?”

I found out he and his wife were living paycheck to paycheck, maxing out credit cards every month. I made them get on a budget. At work, his financial desperation meant he was accepting discounts and bad business just to make money. Once we removed the personal barriers, in nine months, that team went from PIP to President’s Club. As a leader, you have to put your oxygen mask on first. You must know what is holding you back so you can lead your team better.

Brynne Tillman [20:13]: I appreciate this so much. How can people get a hold of you?

Wesleyne Whittaker [23:41]: The best way is yoursalesreset.com. You can grab a copy of the book there or book a call.

Brynne Tillman [21:52]: Well, this is great. Thank you so much. And to all our listeners, when you’re out and about, don’t forget to make your sales social.

Bob Woods [24:32]: Thanks for watching and join us again for more special guests. Hit the subscribe button below to get the latest episodes. You can listen on Apple Podcasts, Spotify, Amazon Music, and other platforms. Visit our website, socialsaleslink.com, for more information.