AI Stories in Sales: Is Your Team Ready for 2026?

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If your company runs on a calendar year, you’ve just entered the final quarter of the year. And if you’re in sales, that means about six weeks of selling time left. Some salespeople may still be selling fourth quarter deliverables. Most are selling into next year.

And someone in the sales organization is focused on the official launch of the new year.

They’re planning for the big sales kickoff, whether it’s in December or January. They’re building the sales toolkit for 2026. And if you’re in sales, you know how important that toolkit can be. It provides guidance on new products and tools, it provides packaging and messaging for new conversations, and it makes a big difference in how quickly you feel confident about the sales goals for the new year.

So, what’s new in that toolkit this year?

Every sales team that we’ve talked to says there’s an AI element.

• Whether they’re asking their sales team to position products that are AI enabled… they’ll need the tools to do it.
• Whether they’re asking their teams to illustrate internal efficiencies and innovation within the company…they’ll need the tools to do it.
• Or whether they want their sales team to illustrate AI capabilities in the sales process itself…they’ll need the tools to do it.

Some companies are leading with AI initiatives, and they put that toolkit in place last year. Others have the foundation of it but expect to expand it this year. And still others feel a little behind and rely too heavily on their product teams to cover it.

But they all agree: AI capabilities and proof points have entered the sales conversation.

As we’ve worked with sales teams, we’re seeing some early challenges that will have to be addressed.

Consistency – Because many capabilities are really still experiments, salespeople aren’t consistent in how they talk about AI. I don’t think you can blame them. They haven’t been given very robust tools to support this conversation. But if they aren’t consistent in what they say, your AI strategy isn’t very repeatable. And that creates an easy way for a competitor to take the lead.

Confidence – Chances are everyone within your team isn’t really using AI yet. It’s a learning curve in every organization. Some know it from their own personal experience. Others know it’s in a product, but they need a product person to explain it as part of the sale. And many say they’re waiting until it shows up in the toolkit. Confidence is a leading skill for sales teams. They sell what they know. And if you’re counting on them to position AI well, you need to build their confidence around it.

Proof points – Sales teams have always sold products and services without deep technical knowledge. They understand pain points and outcomes. And their ability to communicate pain points and align a product or service to challenges helps them build credibility around your outcomes. AI feels different. Today’s communication is deep in HOW and not very clear on outcomes. That leaves a sales team without great proof points.

There’s a communication theme to these challenges.

Throughout 2025, we worked on AI storylines and storytelling, and what we saw was a small group of people in a company tend to own the message. And they’ve assumed that others will pick it up. It doesn’t work out that way.

Clarity builds momentum in communication, not the grapevine.

It’s always easier to invest in momentum at your starting point than to reset messaging after confusion sets in.

If any of these challenges resonate with your group, here are few things that you should add to the 2026 toolkit:

First, an updated, go to market storyline. You may have several of them to address different verticals or customers. But if you’re introducing new concepts and capabilities, it all has to align to what you’re telling customers about your future state in the GTM storyline.

Nothing signals change and innovation more to a customer than the way you communicate with them. Whether AI is prominent as a new enabler and gamechanger in your products or simply a story that illustrates a future state, be sure your team has a compelling storyline that expands your GTM view this year.

Second, your story bank. Stories illustrate how you get to great outcomes. We see sales organizations lose opportunities because they don’t tell great stories.

The examples just aren’t compelling or repeatable because they’re focusing too much on how they solved something rather than setting up a need and an outcome. When we go into a sales organization and coach how to tell stories, it leads to repeatability.

Most companies are tentatively talking about AI outcomes right now. And yet sales teams will tell you customers buy outcomes. So, companies have to find a way to talk about product differences and paint a picture of a future state that customers can buy into.

For many sales kickoffs, we lead story workshops to show groups how to bring outcomes to life, especially at a time when those outcomes may still be tentative.

And third, strengthen personal confidence. For an experienced sales team, confidence comes with discussion, roleplays and a communication strategy to back up AI. For a less experienced team that may be trying to gain visibility and exposure to different levels within a prospect company. And they may need coaching on customer audiences and personal presence.

Sales success in 2026 isn’t just about communication, but communication may make a difference in how your team feels about the year ahead.

And I have a personal story that validates that:

After thirty years of coaching, you get to know industries pretty well. And one of those industries for SW&A has been Fintech. In fact, once we get to know leaders, we tend to follow them from one company to the next. And the concepts you read in this newsletter are concepts we’ve set many times for sales groups: set the storyline and build great stories as illustration.

This year, I got a call from a leader within the industry who had never worked with me. But he told me he felt like he knew me. Because he said I’ve heard your name time and time again when I’ve asked peers in the industry how they learned how to tell great stories.

In fact, he said, “You’ve now beat me three times.

I’ve competed against organizations that you supported, and those organizations have won contracts over me in three different situations. In each of them, I’m fairly confident I had the better product. I just didn’t have the better story. And I want to know how you do that.”

You can see why I love the story!

But I was the supporting role. It’s really a story about well-led sales organizations that had the right toolkit to bring pain points and outcomes to life.

In each instance, it was a leader who understood the impact of communication and the power it plays as a differentiator. We can help your team get there, and your 2026 sales kickoff is a great time to get started.

Click here to schedule a call to talk more about this topic!

Also Read: Communicating the Value & Impact of AI

 

Technology & Coaching: Friends or Foes?

As 2026 planning gets underway every department in an organization is talking about how technology, specifically AI, might improve processes, might drive efficiencies and ultimately might lead to better outcomes.

Learning and development is no exception. In fact, conversations about technology within learning started before COVID and really accelerated when all training switched to a virtual format. It’s led to a lot of learning in the last five years about what works and what doesn’t. And it creates the question that teams considering coaching need to consider:

Do technology and coaching go hand-in-hand or does the value of one negate the value of the other?

It’s a conversation and a perspective we’ve shared with many L&D groups, and with planning top of mind in the coming weeks, it seemed like a good time to share those insights.

Our work on AI storytelling has helped many leaders and companies build understanding of what AI actually is and how it will play out in different ways and across different processes. We think of it as selling to the outcome and painting a clear picture of the end result. That’s how you get people aligned for the effort and work that may be required to get there.

Technology in coaching is a similar comparison. If you think through the outcome you want coaching to deliver, you’ll make better decisions about how technology partners with coaching.

But that wasn’t the approach five years ago. When the outcome was about finding ways to keep people involved in learning, technology served its purpose well. Give employees access to a platform, and they can find resources and short-form courses on many different topics. But as development goals have reset, giving people access to learning doesn’t seem to be enough. And that’s why many organizations are rethinking how they leverage coaching and technology together.

While the big coaching platforms provide coaching to everyone, anywhere and at any time, it comes at a cost of continuity and expertise. When the priority is reaching everyone, technology wins. When the priority is getting results, the 1:1 relationship with a consistent coach is essential. And in most companies, it’s a combination of both objectives reached in different ways that seems to be the best choice.

Specific to communication coaching, technology is very limited. There are innovative AI tools in the market that are exploring ways to assess the habits of a speaker– the number of um’s, the pace of speech, eye movement, etc. But it can’t adjust the habits, and that leaves a communicator with awareness of bad habits but little direction on new ones. More importantly, the emerging tools leave out the most essential ingredient of effective communication, the listener.

Communication is about influence and impact and less about preset patterns of voice modulation. In fact, when coaching focuses only on patterns for a communicator, you’re training to a standardized model rather than someone’s unique skills and strengths. And while it may be efficient, you won’t get great adoption or outcomes. For the best results, coaches and technology need to work together.

Consider these three Cs that we use to blend technology into our practice:

CONFIDENCE – The starting point of measuring results is a participant’s own feeling of confidence and competence about a new skill. We use technology to measure a starting point and end point. Regardless of frequency of sessions or activities someone does through an app, if someone isn’t feeling more confident, they won’t invest the time to strengthen a skill. Technology can track that measure and encourage an individual to see progress.

The coach notices the nuances that technology misses. A participant may say they feel more confident, but a coach can read the non-verbals and the subtle input that suggests the competency isn’t coming through. Working together, technology can give a coach added insights to enrich the engagement.

CONSISTENCY – To develop an effective communicator, you focus less on the occasional home run and more on consistent base hits. That’s when you know that skills are being adopted and adapted into an individual’s approach. A coach hears the results of different settings but doesn’t always see the progress first-hand.

Technology can complete the picture. Video recordings of live events taken from the perspective of a listener can help us assess how the communicator came across and how the listener felt in response to the message. Over a series of recordings, we’re tracking more than the habits of a communicator. We’re getting to group response and engagement with a communicator.

COMMUNITY – Videotaping opens the door to the listeners’ perspective which is the most accurate measurement of ROI. A communicator needs a 360 view to continue to assess and understand impressions.

Over longer engagements with high-profile leaders, we build a feedback loop to capture impressions after high-visibility events. This allows us to blend response to the communicator’s style as well as effectiveness of a communicator’s message. And on all engagements, we can add a pre and post assessment to measure how a communicator’s community is feeling about impact and takeaways.

Again, technology helps us blend anecdotal feedback with measured and tracked impressions. The coach leads the engagement, and technology adds the supporting inputs to validate impact.

So…is technology a friend or foe of coaching?

I would say a great friend, as long as you leverage the strengths of both to better outcomes. AI itself has a great term for how to think about technology in coaching: human in the loop.

Essentially it means keep the coach front and center and focused on guiding adaptable changes for an individual. Leverage technology to track improvement or catch the lack of it across a coaching engagement.

If you’re considering the role of technology in your L&D plans, we’d love to help you consider how you balance efficiencies with outcomes. And specific to communication, how technology and coaches can work together to deliver an impressive ROI.

Click here to schedule a call to talk more about this topic!

Also Read: Communicating the Value & Impact of AI

 

Communicating the Value & Impact of AI

Everybody’s talking about it.

It’s been called the most significant technology advancement we will see in this decade. Some say in our lifetime. And with all the noise, buzz and focus, communication has become a critical tool in how companies position AI within their strategies.

It’s a different conversation at a dinner party than it is on a work team or in a boardroom. Personally, we’re having a lot of fun asking AI to plan vacations and solve our everyday problems. We’re all eager for our own personal agent. It seems like Siri’s distant cousin showed up and can do 10x more!

But in our work environment, it gets much more complex and a little less fun. In fact, most technologists say that how we’re experiencing AI as consumers is confusing what we can expect from AI in our workplace. And when it comes to telling the story of corporate AI, communication isn’t quite as clear or compelling.

We’ve had a front row seat over the last two years supporting many companies with AI communication. We’ve heard groups over promise AI outcomes and lose trust with their audiences. We’ve heard groups over explain AI applications and confuse audiences. And we’ve heard groups downplay AI and disappoint audiences.

Everyone is trying to sprint to early outcomes, but by technology standards, it will be more of a marathon to integrate AI throughout our world. That’s OK. But it does mean that communication will be a critical tool to help AI leaders and business leaders manage expectations, align strategies and bring each of their key audiences along on the journey.

It’s a great example of our storyline methodology because it requires a communicator to focus on audience perspectives, clear messaging and the ability to balance a future state with an actual one. The hype of AI got everyone’s attention as a consumer, but our interest and expectations as a business audience are not the same.

Here are our insights into some of the most critical groups in terms of expectations and how to deliver on them.

BOARD MEMBERS:

This audience starts with their responsibility. And related to AI, they sit somewhere between the intrigue of what you think you can do and the reality of how fast and how well you’re doing it. They are both an internal and external audience, meaning they learn from your internal teams, but they also bring insights from their own experiences. This audience can get ahead of you, behind you or opposed to you based on knowledge they get from outside the company.

Most boards went into last year with expectations around AI investment and measurement. Your goal at this point should be consistency in how you keep them updated. You should have a storyline in place that they’ve aligned to with views of activity, pace and expected outcomes. Keep them involved enough to understand the misses and resets, so they own the learnings with you. Don’t reset the storyline every time you talk to your Board. If they don’t know your AI strategy and progress at this point, you are misaligned. Solve for that by repositioning a high-level storyline – and putting an AI report in place that gives them an enterprise view of what you’re doing.

Missteps: Your efforts around AI will pull your technology leaders into the spotlight. While it’s a strategy for a company, it is a career-defining moment for people leading these efforts. Coach them now on the language of Boards. It’s a different audience for them, and if the Board doesn’t have confidence in your AI talent, you’ll struggle to keep them in step with a strategy.

INVESTORS:

This is the skeptical audience.

Consider them the most knowledgeable in terms of industry perspective and a broad view across your competitors and partners. They’ve heard the AI hype story for a while, and they read between the lines on what you plan to do and what you’re actually doing. Generally, they believe the early adopters will win by getting ahead of everyone else.

They’re tracking progress by digging in on AI investment and AI value. They agree there is potential for AI to transform companies, but most say they don’t truly see it yet. So, they drill down to get to the core elements of what you’re doing. If it’s a new audience for you, know your AI story. It needs to represent a forward view, a current focus and measurable results. All companies are testing how they will report progress in this area. Expect to be held to these measures and get clear on how to communicate about them.

Missteps: Winning at AI from an investor view is delivering customer outcomes. For many companies, a starting point was to talk about their internal outcomes as they learned AI. Companies considered these outcomes; investors consider it activity. Repeatedly, they call out that companies aren’t proving that customers are taking the journey with them. In some cases, this is a lack of good storytelling and knowing how to tell success stories from the customer’s perspective.

CUSTOMERS:

Customers are eager to hear about AI efforts. Like investors, they care less about what you’re proving internally and much more about outcomes for other customers.

They’re also focused on the role of data in this process. We’ve helped many companies illustrate the AI integration journey within a customer’s world, and it gets results. It shows understanding and effort to consider where they can expect the most value and steps toward better outcomes.

Your customers hope to learn from you and other partners, and it’s a great entry point to new relationships within a customer organization. We’re helping elevate and broaden these conversations, so sales teams can use AI to get visibility to other decision makers within companies.

Missteps: Some companies miss the mark by not building AI into their go-to-market message. They give the sales team “hand me downs” from how AI was communicated as a strategy. That breaks a golden rule: the customer comes first. Until it has value to me, I don’t really care what you’re doing to transform, improve or evolve your products and services. That’s your thought leadership and belongs at conferences, not in a sales opportunity.

EMPLOYEES:

For this group, the storyline around AI should be inspiring! We all believe that AI is going to have tremendous impact on our lives, and we want to be a part of it. Share the strategy, and all the good and bad that comes with it. Talk about learnings, failings and next steps.

This is a group that is counting on you to educate them. Whether they’re literally working with AI or two steps away from it right now, they care about it. And if they learn AI in your company, it’s a huge retention tool. Too many companies are putting it in a small, exclusive space, so they can go fast. It’s fine to corner off the work, but don’t corner off communication. It’s too big of an initiative and too central to where you’re heading. Brand the journey and make AI a tool of inclusion.

This is the audience that will build a ground swell around your efforts. Make it understandable to them, and they’ll talk about it and your work around it. They’re the best PR machine you have. They’ll share stories with friends, examples with neighbors and strengthen your brand with AI efforts.

Missteps: For this group, it’s less about missteps and more about no steps. Don’t just recycle content here. Build a journey around AI that is inspiring and includes the entire organization. Employees are a captive audience right now because they want to be involved. Keep them out of the mechanics and engage them in possibilities and opportunities in their work.

 

If you’re in a position to communicate about AI, we can help you balance a future view with a current one. While your audiences have different perspectives and expectations around this hot topic, your storyline has to get to outcomes. And we can help you do that.

Click here to schedule a call to talk more about this topic!

Also Read: Can ChatGPT Write My Speech?

 

Can Chat GPT Write My Speech?

It’s an obvious question as ChatGPT continues to show up in things we google and ways we’re learning to work differently.

But the best response didn’t come from me. It came from a client who said:

Sure, ChatGPT can write your speech – as long as your expectation is a crappy, first draft!

I agree!

Your expectations should be higher than something that would work for anyone in any setting. As I’ve played around with ChatGPT, I’ve learned that there’s an art to how you ask, how you reframe and drill down to information that’s useful. But it is an incredible resource tool that has great potential to get you to that first draft. And that’s the part many people say is the biggest drain of time.

If you’ve worked with our storyline framework, then you know the difference in setting external insights and internal perspective. ChatGPT could be a great resource to help you find those insights to broaden, challenge or expand a locked-in belief. But be wary of easy facts that may not hold up. Be sure you re-research everything you get from ChatGPT to be sure it happened as it’s quote, and the metrics are valid.

As a coach, I’m always a little skeptical when the question is ‘can ChatGPT write my speech?’ vs ‘can ChatGPT find interesting facts?’. It makes me wonder if the goal was a shortcut versus a memorable speech. I’m all for leveraging these tools – as long as your goal remains impact versus efficiency. And before you rely on AI as a viable partner, here’s a quick reminder of what your expectations of yourself should be as a communicator.

Before you align to an easy way out, think about what good looks like and how you should evaluate yourself in terms of expectations and results.

Before every significant communication, ask yourself three questions:

Is it you? – Communication should align to a communicator’s brand. Would people in your audience say –“I can see why he did it.” Or “That’s so in line with who she is.” There are several ways to make content your own from storytelling to word choice to delivery choice and many more. Authenticity is the top attribute listeners describe with presence.

ChatGPT can’t give you that.

Is it memorable? – Attracting and holding the attention of any group is more challenging than it’s ever been. Listeners are distracted, impatient and many days, flat out uninterested. Your content has to break through that. And in many cases, it takes the ability to react to people in the room more than preplanned content you set a week ago.

It’s hard work to find the thread that will pull people into your ideas. You need to know them, you need to align to them and then you need to find a way to pull their interest into your ideas.
You want the content and context you share to be memorable so that the group you meet on Monday shares it with the group they meet with on Thursday. Whether you’re the CEO or the operations manager, the goal of communication is to help information travel.

ChatGPT can’t define that.

Is it actionable? – While I often say there’s no pass/fail in communication, there is impact. And all the effort you’ve put behind a message and a speech is best measured by whether or not listeners took away an actionable insight. Internally, did they rethink the way they’re approaching a project or a work team? Externally, did they have an “aha” about your solution or a broader view based on your insights? Did you ask them for follow-up or action steps? Did you create urgency to act or build trust to work together?

ChatGPT can’t do that…But you can.

You can gauge every speaking opportunity against those three questions. It raises the bar on expectations – and challenges you to take responsibility for making something happen as a result of your communication.

So, can ChatGPT write your speech? Not as well as you can.

Crappy, first drafts seem better suited for wedding toasts than business communication. Assign ChatGPT and AI a supporting role and maybe those swirling data points will inspire you beyond the crappy, first draft. Great communication deserves a little sweat equity and the best of you.