AI Knowhow Episode 71 Summary
- With all the noise surrounding AI, how can leaders choose to invest in those AI initiatives that will have the greatest impact on their company and their team? Developing an AI roadmap is a good place to start
- Individuals interested in future-proofing their careers can also benefit from some strategic thinking about what their personal AI roadmap might look like
What does an AI roadmap really look like? And how does a corporate AI roadmap differ from a personal one? In this episode of AI Knowhow, CMO Courtney Baker is joined by Knownwell’s CEO David DeWolf, Chief Product & Technology Officer Mohan Rao, and NordLight CEO Pete Buer to break it all down.
First, the team explores how business leaders can chart a clear AI strategy—starting with vision, linking it to business goals, and balancing customer feedback with long-term objectives. David and Mohan share insights on making micro-pivots, avoiding roadmap confusion, and the key decision every professional services company must make: is AI a tool to facilitate work, or is it essentially your operating system?
Special guest Dr. Joan Palmiter Bajorek, author of Your AI Roadmap: Actions to Expand Your Career, Money, and Joy, sits down with Pete to discuss how professionals can future-proof their careers with an AI strategy of their own. She shares why a strong personal brand, multiple income streams, and financial security are essential in the AI era and how workers can position themselves for long-term success.
And in our weekly AI news segment, Courtney and Pete dig into a recent story from Entrepreneur about a new line of AI-designed shoes. A new shoe that’s the result of a collaboration between the founder of Reebok and a serial entrepreneur combines AI-driven custom fitting with personalized footwear, raising big questions about AI’s role in design, manufacturing, and consumer trends. Is it just a gimmick or a glimpse of AI-powered retail and a trend toward hyper-personalization to come?
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Show Notes & Related Links
- Connect with Dr. Joan Palmiter Bajorek on LinkedIn
- Buy Your AI Roadmap: Actions to Expand Your Career, Money, and Joy on Amazon
- Connect with David DeWolf on LinkedIn
- Connect with Courtney Baker on LinkedIn
- Connect with Mohan Rao on LinkedIn
- Connect with Pete Buer on LinkedIn
- Watch a guided Knownwell demo
- Follow Knownwell on LinkedIn
What does an AI Roadmap look like?
And what’s the difference between a corporate AI Roadmap and a personal AI Roadmap?
And how do they intersect?
Hi, I’m Courtney Baker, and this is AI Knowhow from Knownwell, helping you reimagine your business in the AI era.
As always, I’m joined by Knownwell CEO, David DeWolf, Chief Product and Technology Officer, Mohan Rao, and NordLight CEO, Pete Buer.
We also have a discussion with Dr.
Joan Bajorek, author of the new book, Your AI Roadmap.
Did you know the first AI shoe is now available?
True story.
Pete Buer joined me recently to break down the story and what leaders can take away from it, and where you can get your own pair.
Hey Pete, how are you?
I’m good Courtney, how are you?
I’m doing great.
Pete, I am curious to find out if you have space in your closet for a new pair of scintillates because they’re the first AI designed shoe.
Entrepreneur wrote about the shoe which is the result of a collaboration between Reebok’s 89-year-old founder and a 25-year-old serial entrepreneur.
All right.
So are you getting these things?
First, let’s talk about the merits.
So scintillates does custom fitting using some combination of AI and your smartphone camera to get an appreciation of your unique foot size and shape and to build a shoe that uniquely in a bespoke way fits you as a segment of one.
Personalized comfort and personalized look and feel, presumably.
Behind the scenes, of course, the company has the ability to gather the data and start making smart decisions about trends in footwear and foot sizes and I don’t know, things that matter to people at Reebok, I suppose.
So is it a gimmick?
Sure, it’s a gimmick.
But so are half the things I buy on Amazon from one month to the next.
Is there a business lesson for us all in this?
Well, sure, there is as well.
Pretty much anything can be AI-ified nowadays, right?
When you get right down to it, if I’m oversimplifying.
And so are you as a business leader looking everywhere across your business at all the different opportunities and making smart decisions about where you might spend a little innovation energy to bring along something maybe the world hasn’t seen before?
And also are you going back to first principles about design and manufacturing and making sure that whatever it is you’re creating has a purpose that it serves, it’s viable, and there’s revenue to be had in developing it as a product or a product line?
Now, on the question on the shoes.
These shoes were designed for someone who is not me.
And so I will not be buying them.
As a friend pointed out to me, they look like dinosaur feet.
And I don’t think that’s going to do much for me.
That’s your vibe.
I mean, no, I mean, it would be amazing.
I mean, if you got them, could you show us on the podcast?
Maybe we can provide you a pair.
I could, I won’t get them.
But if you were to mail me a pair, I would put them on camera and show you what they look like.
Yes, great for this show.
Well, I will say, Pete, this reminds me of something else you have said to me before, which is every company is a technology company nowadays.
And this kind of reminds me of that adage of yours, which is, will we all become AI companies at some point?
In some ways, Reebok is already making steps to become one themselves.
100%.
Okay, last thing, in case you’re wondering, Reeboks are back, people.
It’s the cool trend.
So if you liked them when you were a kid, they’re back.
So there you go.
Pete, thank you as always.
Thank you, Courtney.
This is the first episode that we’re running on Applied AI.
How can you take everything you’ve learned to date and put it into practice?
That is what we’re gonna talk about today.
David, Mohan, I wanna talk with you about how executives out there listening can chart their company’s path forward with AI.
I know every company is different and unique, but if you were to think of an AI roadmap for professional services leaders, what would it include?
You know, I’d start the roadmap every time that I start the roadmap.
There are some enduring principles, right?
So you start-
I know what you’re gonna say.
Tell me, tell me.
Well, actually, now that I said that, I’m like waiting to do two things.
I think my gut said initially that you were gonna say problems.
You start with the business problems.
But then I started second guessing and I thought you might say, you need to start with the vision of the company.
Oh my God.
Yeah, it’s the answer B.
That’s where I’m gonna start.
Yeah, it was my second take.
Okay, good, great.
I’m learning so much.
In a year and a half of recording this podcast, I feel like I just got an A plus there.
Okay, so vision.
Start with a vision.
I’d start out developing the AI Roadmap.
Just like anytime you have to develop a pretty big roadmap, what is the overarching vision that you’re trying to achieve?
So it’s got to start there, and then linking it with business goals and coming up with some high-level themes.
So you both know this.
I’m very top-down in my learning and in the way I explore things.
So you’ve got to go top-down.
It’s impossible to go bottom-up with these types of efforts.
So you’ve got to go down.
Why are you building the roadmap?
Just start there.
There are a few other things I’ll add.
You know, involving the stakeholders early and often.
So you’re getting a lot of inputs.
You’re early customers.
The mistake that a lot of people make is then they go into developing features, right?
So just going to hold off on that and start then thinking about the outcomes that you want to achieve.
And then have a set of outcomes that are more near-term.
This is what I want to do.
Mid-term, long-term, however, you want to do that.
Now, next, later type format.
But you start thinking about outcomes.
The key is to think of roadmap not as every little thing being documented, but there is enough detail for immediate action, but also that allows flexibility for changes.
So that’s how I think of a roadmap, and how you start laying the pieces down.
David, what do you think?
I think you guys are on the same page.
I mean, basically, you just said in three paragraphs what Courtney said in two sentences and expanded on it.
You guys are totally insane.
It’s awesome, right?
You start with the vision, you identify the pain, then you define the outcomes.
Absolutely, it’s like we hang out together all the time or something.
I would say there’s another aspect with this, with AI that I want to challenge folks to think about.
And it’s going to exercise your abstract brain a little bit here.
But we’ve talked about this before on the podcast.
I think that an operational applied AI platform and an execution-oriented applied platform are two fundamentally different things.
And the two don’t necessarily live together, and you will confuse your users, and you will confuse your value proposition.
You will confuse a lot if you don’t get clarity on that.
And so just to be the contrarian here, because I totally agree with everything you said, but it wouldn’t be very interesting if we all just kept repeating each other.
And so I’ve got to come up with something new.
I would say that really getting clarity of, are we looking to drive efficiency and productivity and just help individual workers to perform more work, better work, and execute their tasks better?
Or are we trying to orchestrate multiple business processes, bring them together, make better decisions, and orchestrate the business?
I think that’s actually a fundamental decision you need to make when you’re building an AI platform.
I mean, is it a tool or is it an operating system?
I like that.
That’s the way to think of it.
But David, let me take this in a different way that I know that you’re going to love.
When you start with the roadmap or even the company, the startup or a big project, you have a core vision and you have a very principle-based vision that you’re looking at, and you want to execute on it.
Then you start getting early customer feedback, and the two are in conflict.
We have said repeatedly that we are going to be customer centric.
Do you evangelize the product roadmap that you started with, or do you really listen to customers like we’re supposed to?
What is your answer there?
Like we’re supposed to.
If that’s not leading the witness, I don’t know what it is.
I think he’s trying to back me in the corner here.
You’re right.
I am excited about this question because I’m pretty passionate about it.
I think it’s actually the hardest thing about being an entrepreneur.
The hardest thing about being an entrepreneur is you have to live at the intersection of two things that seem in utter conflict, and you have to not only survive but thrive through that conflict.
The first one is to be a successful entrepreneur, you have to be maniacally focused, believe and have utter amazing confidence in your vision.
You are going to get there and you will not give up.
At the same time, you have to be incredibly humble, able to listen, to digest, to understand, and to evolve the roadmap to figure out how you’re going to get to that vision.
Now, one of the key things to making sure you do this successfully is that you have to think at a visionary level when you’re setting that vision.
Too often, people define their vision as something very, very pragmatic and tomorrow.
A vision, I love Good to Great.
Go back to Good to Great, the big, hairy, audacious goal.
It’s tend to, he recommends, 20 years from now.
How are you going to impact and change the world as a business?
That gives you enough space to navigate within it and stay committed to that vision, but to evolve that vision, to grow that vision, to refine that vision, and even more importantly, the roadmap of how you’re gonna get there along the way.
And so, I think both are essential, and you can’t choose one or the other.
You’ve got to have both.
If you just listen to customers and do what they ask, you’re gonna be thrown around all over the place.
You’re never gonna build anything of substance.
If you are not oriented the other way and you don’t listen to your customers, you’re never gonna find product market fit.
You’re never gonna sell anything to a customer.
You’re just gonna be a stubborn individual in an ivory tower that thinks they know more than anybody else.
You’ve gotta live at the intersection.
You’ve gotta thrive in that intersection.
David, you talked about living in that intersection.
But sometimes when you live in that intersection, things are not working.
So when do you, and Courtney, this is a question for you as well, when do you persevere and say, I’ll crack the code on this, versus when do you pivot on your roadmap?
Right?
So because you can live in the intersection, but the intersection might not be working.
So I think one of the axes is changing literally, not only every day, but every minute.
Like you are continually collecting information and applying that information to the roadmap.
And that means this is where entrepreneurs get a bad rap from their teams, because everybody wants clarity, and I just want to execute the entrepreneur keeps on coming in with the new crazy idea, and disrupting the roadmap.
And well, some of that is absolutely necessary.
Right?
And literally, you’re doing it best.
Go back.
We just had an episode about the lean startup.
Right?
These are the principles of the lean startup that are so important.
You’ve got to be testing these ideas that you have with real customers, getting real feedback.
And that needs to start with just conversations, then turn into a paper napkin, then a paper drawing, then a printout of the drawing.
All right.
Like it’s got to get higher and higher fidelity.
You got to test it very, very iteratively and rapidly.
I tell people a lot that when they ask about the journey of Knownwell and how did we find a market so quickly and all these things.
Literally, in the first few months, hundreds of customer names, like three, four a day of leaders that I was talking to, just collecting data points, synthesizing them, testing out my aha moments the very next day, the same, going backwards.
Those were all very little pivots, and the smaller the pivots you make, the smaller the pivots you make.
If you’re adjusting every single day, it doesn’t feel like a huge massive pivot.
Every now and then you run into a huge massive pivot.
But if you look at the Knownwell story and the Knownwell journey, you will not find this big right-hand turn or left-hand turn somewhere.
What you’re going to find is one-tenth of a percentage of a degree turn of the steering wheel, again and again, and then back the other way, and again and again and again.
And I think that is how I think about it, is always consume information, always question your assumptions, and continue to go over in your head this framework that you have about what that road map is, what that vision is, and continue to get the sandpaper out and just make it more and more and more smooth.
The only thing I would add to that is you just have to make sure as you make those micro pivots as the entrepreneur, that you’re bringing everyone along with you.
Yeah.
No, I was not pointing fingers at all.
Because then what it can feel like to your team is that bigger move.
And so you just have to bring people along as you’re making those adjustments.
You know, I’d also add, in addition to the people side, Courtney, you need to have a flexible technical architecture that’s going to be important here that allows you to make these changes, right?
And probably very flexible people.
People who do yoga.
Yeah, that’s right.
Actually, that’s where you should find your AI team.
Is that the yoga studios?
That’s what we did.
You know, and Courtney, I think another thing that, as we talk about this, is interesting to think about is obviously this is, we’re sitting here talking at the Knownwell journey and the way that we are applying AI in a product we’re building for services.
For a lot of our listeners, they’re services companies that may be moving towards more of a tech-enabled service.
And some of this thinking could be helpful as they go down that path, because you become more and more of a product company, should be thinking more of a product company, they’re different business operating models, right?
When you get there.
But also, I think there’s also, you know, having the type of clarity we’re talking about, moving with the type of agility we’re talking about.
Some of those underlying principles can still apply, even when you’re talking about not necessarily building a product, not even tech-enabling your service, but even when you’re thinking about, how do I take this new technology?
Maybe I’m looking at buying a platform.
Maybe I’m looking at some new internal tools that I’m building.
I would recommend that there are some underlying truths in here that can apply to those situations, even though they’re a little bit different.
Yeah, absolutely.
Really good point.
Well, David, Mohan, this one was so su-
I’m so glad you changed it up.
Mohan, you got to work on that.
David, Mohan, thank you for this conversation.
Really insightful stuff there.
We’ll add it to the roadmap.
Listen, guys, it’s the things that you didn’t know, you didn’t know that really gets you.
And that’s really true when you lose a good customer by surprise.
It is painful.
It’s one of the worst feelings in the world.
And it’s exactly why we created Knownwell, to deliver real-time insights into how your client portfolio is actually performing.
You can say goodbye to guesswork and throw those NPS scores out the window, because let’s face it, they’re not really helping you that much anyway.
Visit knownwell.com to learn more, and let us know if you’re interested in our AI-powered platform for commercial intelligence.
Dr.
Joan Palmiter Bajorek is the author of the just-released book, Your AI Roadmap.
She sat down with Pete Buer recently to talk about how to future-proof your career by laying out your very own AI roadmap.
Joan, hi, welcome.
Hi, Pete.
How you doing?
I’m good, thanks.
So nice to have you on the show.
I want to start with congratulations.
I understand you’ve got a book soon to be published.
And am I right to that the initial release date is tomorrow?
It’s tomorrow.
Tomorrow.
So the book, for the benefit of those listening or watching, is Your AI Roadmap, Actions to Expand Your Career, Money, and Joy.
Tell us about the premise.
Absolutely.
Well, I have been in two AI layoffs.
Super fun, but here in Seattle, this is actually more common than you might think.
But been very resilient through the ability to be an entrepreneur, to close six and seven figure contracts.
I had a robust network, but people have been in my DM saying, how did you do it?
I’m scared about layoffs.
What next?
Serving my community, literally with those answers, things that I answer people in quiet about career, personal brand, and money are all answered in these 200 pages.
Wow.
Two AI layoffs in one local market, large companies, I guess, and what kind of brand does AI have in a labor market like that?
Well, let’s see.
The funny thing is I literally work on building the AI, so it’s very metaphysical going on there.
But AI frequently takes jobs, people don’t want to talk about it, but we’re automating work, right?
And this volatility of you raise a ton of money and then, oh, you’re not closing up contracts internally, 30 percent of the company laid off in a day, right?
So workers ourselves have to be resilient.
So at the heart of the book is the notion of an AI roadmap.
What is it and how does a someone who’s looking to shape their life, you know, consider using it in the day to day?
Absolutely.
Well, my concept is I don’t think it’s going to become more stable from here.
I guess it’s kind of my assumption.
And so to build your own AI roadmap through the volatility, there’s so many opportunities in volatility, somewhat counterintuitively, we can use AI tools to help us.
But robust personal brand, who are you as a human, right?
Your network of humans who can help you land the next thing, and finances, basic one-on-one stuff.
I’m shocked that people around me seem to have tons of money, but don’t actually have the security that one might expect of someone who lives in Seattle or a tech network.
So really, nuts and bolts, how I built wealth and stay stable.
And I guess the notion of a roadmap kind of implies, it’s going to change and going to respond to market factors, etc.
Is that a fair interpretation?
It is, and it’s very actionable.
There are templates in it.
It’s not passive, like, I’m going to make you feel happy.
It’s like, let’s get down to business.
Let’s do these things.
Let’s take action.
And am I right also to understand that we’re talking about powering the individual to strike out on their own and figure out what’s next?
Is there a corollary for the individual inside of the business, who wants to stay with the business?
Does the roadmap serve that kind of career ambition as well?
Yeah.
I mean, it really focuses on having other income streams.
I kind of talk about diversifying income in and out, or money, money in and out, and being thoughtful about your finances.
I think being an entrepreneur and opportunities within a company, it’s not really covered in my book, but I personally can say that seeing opportunities, bringing them to your boss and saying, hey, I see value in this, love to tackle it.
How can I future proof myself at my current company in the, you know, a wonderful environment I currently love?
And so, do you advocate sort of the portfolio approach to career?
Like you should kind of have a bunch of irons in the fire, each to mix metaphors producing an income stream?
Yeah.
I have 22 income streams and I lost them all.
And it really helps me because they’re like when things are moving quickly on one, net 90 on a contract that takes 90 days to pay out.
Like, I’m dead serious that I write them all out for the public.
To share, because a lot of these I’ve learned from my mentors about signing bonuses and equity deals that I want other people to know about.
Let’s roll the movie forward and imagine a future where the workforce is some combination of hiring, hired and gigging with a bunch of revenue streams individually coming from a bunch of different sources.
As an employer, does my strategy need to change in the labor market?
Am I just trying to get a piece of everybody or am I trying to get, is it a wallet share game at that stage?
Ooh, I like this question.
I think smaller teams is certainly what I’m seeing.
Fractional, I don’t know if you’ve seen this movement in the fractional CFO, for example.
It’s a fabulous opportunity for employers.
I think it’s a, hopefully, we treat our employees better to retain them because they will have so many options, I believe.
I also really love advocating for alternative businesses.
Like there’s a really gourmet donut shop with a line around the block near my house.
They’re making hand over fist with donuts.
They don’t need to be in software.
So thinking outside the box.
I’m the head of HR, I’m a CEO who’s thinking hard about the labor market and winning share, getting the best people at a rate that I need to get them.
How do I approach talent acquisition and retention differently?
Treating your employees really well.
I was just talking to a CEO yesterday who’s really worried about some top performers leaving.
He was saying, I’m going to robust health care, taking care of their kids well, flexible hours.
It’s really pushing the future of work towards a more humanistic approach.
It seems like over the years, the balance of power between employer and employee has shifted back and forth from the old paternalistic days where the company called the shots to work for talent and so on and so forth.
Is the presence of AI and the uncertainty around it causing and the availability of gig alternatives causing another shift in the balance of power?
I really think it’s about the seniority of the individual actually.
I see people kind of entry level being pushed around, work 70 hours for the same paycheck type of behavior, but for senior contributors who are invaluable to their companies.
They say return to work and he’s like, actually hard pass, you’re going to fire me.
I know several individuals with that story.
If I’m a CEO listening to the podcast and you inject me with truth serum, what’s the question you’d want me to be able to answer as relates to employees and their careers going forward?
I think supporting them, or one of the things I’ve noticed, maybe it’s a generational thing, I’m not sure, but if a CEO is listening and you’re maybe more senior in your career otherwise, personal branding and networking can actually be very beneficial for the company.
I’ve taken a little heat from companies being like, Joan, you post a lot.
I don’t know how we feel about that.
Joan has the ability to walk whenever she wants, and some companies see that as a threat.
Yes.
Some companies see that as Joan can bring leads for us.
Yeah.
If we can use that messaging.
I really think that aligning on those brand, that brand piece, knowing that network, these evangelist type rules exist more and more.
But I hope that the CEO potentially listening to this says, what top performers can we leverage?
How can we retain talent through that upscaling?
Is there even a role that companies can play to broadcast or amplify individuals brands?
Does that come at the expense of company brand?
That’s fascinating.
I think it’s a brave new world of individual working at the company versus that I’ve literally got CEOs pinging me being like, I want to hire you because our brand aligns, because you have this technical acumen, people respect you, our company loves this, let’s work together.
That’s cool.
Something about when you take a job or when you stay with a job, you’re making all kinds of trade-offs.
There are dozens and dozens of attributes that include, but aren’t limited to how much you’re getting paid or whether you’ve got a good manager.
The degree to which a company makes me more marketable in the long run, maybe that becomes a lever that’s more important going forward than it has been in the past.
Well, isn’t that the paradox, right?
If we help people internally upscale, will they leave or, uh-oh, will they stay and we don’t upscale them, right?
It’s kind of this paradox, but I’ve literally been, I was working at a company and Google tried to poach me and they could have paid me more, et cetera, and it’s Google.
I loved my manager.
I was actively learning a bunch.
I’d signed the biggest contract of my life.
I was satisfied.
I was not interested in even taking that call.
I think hopefully other employers can look to that as well.
Right.
That’s such an important thing for managers to focus down on.
No two people are alike.
For the next person that Google tried to poach, maybe when they saw the salary, their eyes popped and they left, right?
But for you, that wasn’t the drivers.
There’s something about understanding the individual career drivers of your people that’s incredibly important.
Joan, it’s been a pleasure.
Thank you so much for being here.
We appreciate you sharing your insights.
Absolutely, Pete.
It was lovely speaking with you.
Thanks as always for listening and watching.
Don’t forget to give us a review on your podcast player of choice.
Seriously, it really helps the show and it helps other people find it.
At the end of every episode, we like to ask one of our AI friends to weigh in on the topic at hand.
So hey, Claude, what’s happening?
Haven’t seen you around much lately.
This episode, we’re talking about how to develop an AI roadmap.
So what do you recommend?
Start by getting clear on the actual business problems you want AI to solve, since that’ll keep you focused on what matters.
Then just map everything out in manageable phases.
Grab some quick wins first to build momentum, then tackle the bigger stuff once you’ve got some experience under your belt.
And now, you’re in the know.
Thanks as always for listening.
We’ll see you next week with more AI applications, discussions and experts.