Summary
We covered reskilling mid-career leaders in the AI era, with Dean Cantave as the special guest. The discussion covered how senior professionals can stay relevant as AI technology transforms the workplace, with participants sharing personal experiences about career transitions and skill development. Key topics included the importance of critical thinking, collaborative leadership, data governance, and AI agent orchestration, along with strategies for making leadership competencies visible and credible in today’s job market. Guests emphasized the need to move beyond traditional certifications and focus on demonstrating tangible results through visible professional activities, thought leadership, and effective communication of personal brands. The conversation highlighted how roles are becoming increasingly cross-functional, requiring leaders to adapt their approaches and develop new skills to remain competitive in the evolving AI-driven workplace.

Speakers
- Host – Isaac Sacolick
- Guest speaker – Dean R. Cantave Sr., Deputy CIO
- Digital Trailblazers – Derrick Butts, Martin Davis, Joanne Friedman, John Patrick Luethe, Liz Martinez, Heather May, Joseph Puglisi, Elena Putilina
This week’s discussion
- Many mid-career leaders are feeling anxiety about their future career opportunities. What advice can you share with them from your experiences that remains relevant today in the AI era?
- Where’s the gap between the experience senior leaders think they have and the skills the AI era actually rewards?
- How should a mid-career leader actually make these competencies visible and credible?
This week’s research

Transcript
[00:00:01] Speaker A: Greetings everyone.
Welcome back from the July 4th weekend. We took last Friday off to give everybody a chance to just get some time away and not have to break from your time with family or time with friends to do a coffee hour or listen to a coffee hour.
And we are back this week. We will be here most of the summer. I may have another week off but this week’s topic should be important to all of you. We’re talking about reskilling mid career leaders. What senior talent needs to stay relevant.
And just in case you are wondering whether you are to be here, you’re in the right place. When I call mid career leaders, it’s pretty much everybody except for entry levelers and those coming into the job force. We actually had a conversation with people new to the job force and graduates three or four weeks ago.
If you are here listening and you’re a graduate, let me know and I’ll send you a link to that particular episode. But right now we’re talking about something we all have done, we all have to do, which is keep current is what used to be called when I was in college and continues to be a phrase you’ll hear from people.
And obviously in the AI era this has taken on a lot more meaning.
This is, I don’t think anybody is immune from it. I think the pace of which we have to reskill is increasing. I think the importance for us to stay employed or find new jobs is really important and so we’re going to go through a lot of that here today.
If you are here new, we do have a comment stream. It’s pretty lively.
I want to say hello to Jason who will be on, I think it’s next week’s episode so we’ll talk about that when I announce next week’s episodes. Hello Renato, Cheryl, welcome back. John, welcome back.
Great to see you all here.
Derek, we’re going to let you in right now. I didn’t see you were waiting in the waiting room. Derek is joining us. Hi Dave, good to see you. And Maxim, good to see you. So let’s just get started.
Let me remove the banner and let’s talk about reskilling mid career leaders. What senior talent needs and what you’re seeing here is on the left side is just some motivation. Some of the data points I found about reskilling, the first data points actually come from the Society of HR Management.
They said 41% of U.S. workers use AI at work, 47% of U.S. organizations use AI. I don’t know if I believe that number. I Think that number is actually a lot higher than what people are admitting to. But here’s what surprised me. And if you think about previous technology transformations and evolutions, we usually think about the digital natives, the younger folks, the individual contributors who are the ones adopting faster and the ones who are potentially most disrupted and getting benefit from it. And what you’re seeing here comparing individual contributors, managers and directors, the hours per week is double for the director.
The percent of using AI assistance is one and a half times those of individual contributors and its importance around career prospect and around experience is that much higher.
So you, you have quite a bit of, of, of of incentive. Let’s just call it around you, you know, getting involved in AI and get, and, and finding ways to use it and getting benefits from it. I also like this data point from beautiful AI. AI’s impact on the work.
58% of managers rate AI’s output at least equal to an experienced manager or better.
Oh, that’s frightening. So now, yes, we are in competition of outsourcing ourselves our management skills to AI. 17% it’s at least equal to an expert manager. And 12% per se, it is better than human manager Albert’s. That is really, really, really scary.
So let’s.
Oh gosh, somebody is moving my screen. Not good. Whoever just did that has to move it back or I cannot see it.
Let’s talk about some of the the future of jobs report that I say Future of jobs.
Just several different skills that I want to call out that I think are really important.
Number one is critical thinking, creative thinking.
And I think that that’s really important. I think number two from Atlassian’s report, Collab, what they call collaborative leadership is really important. I have just lost our banner, which is really, really bad because I don’t know how to bring it back.
And let me just see if I can bring it back so we could all see it again.
Here we go.
And here it is. Okay, Liz, please lower your hand so that we don’t have this moving around again and I’ll call you up a little bit later. All right. World Economic Forum Creative. You know, they gave us some data points around critical creative and analytical thinking.
Atlassian has a really good report called the State of Teams 2020 collaborative leadership is where they highlight 77% teams are more horizontal with fewer layers. And 73% have blended roles with hybrid responsibilities.
Change management, something we’ve talked a lot about here. I don’t see Martin here. I hope he joins us. If not somebody else, take the softball and let’s talk about change management as a critical skill set.
Adobe in their 2026 AI and digital trends reports highlights the importance of data and AI governance skills. It’s not just a job or a responsibility, it is a skill set. Marielle on the screen will come back or we’ve got it back up and running.
So very important. If you’re building your skill set up, think about data and AI governance and then something we’ll have a dedicated section to AI Agent Orchestration. We had a previous coffee hour where we talked about managing AI agents and managing AI agents is now scaled up to a larger conversation around how do we orchestrate workflow that includes multiple AI agents and people. And it’s not just human in the middle, it’s human augmentation.
And for those of you who want an insight around what AI agent orchestration is all about, I gave you some links from IBM, Snowflake, Data iq, Deloitte. I have a research paper that’s coming out on that in September.
And if you want this slide new format that I’m doing Today, go to drive.starcio.com Coffee pretty easy to remember. Drive that starcio.com Coffee and you’ll get this slide. It’s clickable so you can get to all the references. The questions that we’re covering today will be up here and then the dashboard we’re about to start working on will be up in here. So folks, welcome to this week’s episode and I want to welcome our guest, Dean Cantav. Dean and I are friends.
We’ve been on each other’s programs a couple of times and I just said, you know, he had, he had some leadership program that he was doing a couple years back that he had me join and I said I think you’d be the perfect guest to join us. Dean, I want to hear a little bit what you’re doing now since we last talked and then I want you to go back in time. You know, go back to when you had the realization moment that you had to invest in yourself and in your career. When you where you start feeling nervous a little bit that maybe what your expertise was in and where you had experience was started to get a little bit of fading and you had to retool yourself, talk about how that felt and how what were some of the inflection points that said you needed to do something different. And let’s put ourselves in the eyes of everybody listening here and say what is your advice for mid career leaders? Dean, welcome to the floor.
[00:09:28] Speaker B: Good morning Isaac. Thank you for inviting me back to the program. Can you hear me okay?
[00:09:31] Speaker A: I can.
[00:09:32] Speaker B: Awesome. Awesome. Well, what I’m doing now actually ties in with the theme of what you’re presenting here.
I’m 25 years in tech and starting help desolate in the military for six years and starting to help desk with the city of Chicago and then just work my way up through moving through roles. Spent most of my time in project management and that’s where I developed my IT infrastructure and leadership chops over several years and then moved into leadership positions after that.
But in 2018 I had well over 2017. 2018, I had between those two years, I think somewhere between three to 400 interviews in those two year periods including phone screens. And I could not land a leadership role.
And I went to a party in 2018, late 2018, I met a gentleman, his name is Ralph Kendrick, and met him at a party, didn’t know he was and come to find out He’s a former CIO of DeVry. He had been a former CIO and CTO for several universities out west.
And he taught me about the difference between being an operator and being an executive. And he taught me and was explaining to me after he had talked to me a while about the problems that I was having in terms of advancing my career. He explained to me the language that executives use that operators don’t use. And he explained to me and taught me about risk.
And he talked about the first 90 days and he talked about all these concepts that I was not aware of. And then I sat down and thought to myself, well, if I’m not aware of these concepts, I’m pretty sure there are thousands of IT professionals that, that want to be competent, more competent in IT space that don’t know these things. And nobody taught me these. There’s nowhere for me to go for me to learn these things.
And I worked with him and that set off a different strategic direction for my career where I started applying for roles and eventually moved up into some leadership roles, eventually to where I’m at now as a deputy cio.
And what, what happened is that I realized that I needed to turn around and now give back to the community and help teach people about what it means to actually grow a career the right way.
So what I’m doing now is I’m developing a platform to help people do that. And in the age of AI, what I think is important for mid to senior level professionals to understand is that AI is collapsing the labor market. That’s one. And then two, the reskill is really understanding how all these systems blend together because AI has the ability to do that.
So the domains that I think that are important are number one, communication, leadership, project management, data literacy, AI literacy, and then a systems thinking mindset. Because now technology systems, they’re, they’re ubiquitous. You can have a workload in GCP over here, you can have something AWS over here. And you need to be able to understand how to link all these systems together for companies to accomplish whatever the task is.
[00:12:47] Speaker A: Love it, Dean. I love hearing what you’re doing.
Is there a place people can go get involved in your programs? Is there a URL we can put up for that?
[00:12:58] Speaker B: Yeah, it’s GetSkillsGap AI is the website and I have a list which is on my LinkedIn profile page. If you go there, you can opt in as well. But the primary website is getskillsgap AI.
[00:13:12] Speaker A: Excellent. Let’s bring up our speakers.
Liz and then Derek were our first hand raisers. Liz, your sort of inflection point where you decide, I need some better skills and how you went about doing it, or different skills? Not better, different, different skills.
[00:13:33] Speaker C: Well, so what I was thinking as they started talking about this topic is really you should always be learning, always. Everybody should always be looking for where they can stretch either their existing expertise or find new expertise that it’s so important, I mean, not only for your brain, right? Just think about, you know, your plasticity of the brain itself as you grow and as you age, how you want to make sure you’re continually challenging yourself. It’s the best way to keep out dementia, first of all, but just to keep yourself interested.
So it could be something as silly as, you know, well, I might be interested in picking up Spanish that could actually open up, you know, bilingual opportunities.
But in today’s day and age, and I’ve been doing this myself with Claude and ChatGPT or whatever, you know, pick your poison, build out ideas about what you might want to work in the future, what your next role might be. And ask ChatGPT or your preferred AI to give you some, an outline of, you know, skills gap, skill gaps based on your existing resume and experience and maybe even create a plan for yourself. Like, I like to work an hour a week or 15 minutes a day on building these skills. Give me some ideas on what I can do and what milestones might be appropriate and let it rip because this thing can really help you structure not only, you know, your, you know, learning path, but really what your future role might be.
[00:15:20] Speaker A: Liz, what I love about what you’re saying is this concept of partnering with AI, let’s just say I’m in the midst of writing something new without calling what it what it is.
And that’s a big part of what I’m writing about, is that transition point where you’re not just going to an AI with a specific question or something that you need and you make that sort of mental shift. And now you’re working with AI not to get your work done, but to partner with you to help you get your work done smarter and not even necessarily faster.
[00:16:02] Speaker C: And that’s why I raised my hand before, because you were talking about AI as having as good or better results than other than, you know, existing, you know, mid career or senior executives. Here’s how I think of that. I get to have somebody at my side who is as good or better than I am on my team.
That’s amazing. That’s not threatened by it. That’s, that’s my buddy, that’s my pal, that’s my team.
[00:16:34] Speaker A: Derek is giving you a thumbs up for that one. Derek, welcome to the floor. Your story on reskilling.
[00:16:41] Speaker D: Yeah, good morning everybody. Yeah, the reskilling thing, I mean, I think it was mentioned earlier and Dean had a good point there as well as Liz, the changing of the mindset. You know, years ago we looked at this, it was about you were paid for what you knew. And I think with today’s age is scaling of adaptability, how value you can become not just based on your expertise, but how quickly you can learn to adapt. And I think when you look at the way the landscape, the change and the way companies and individuals are using artificial intelligence, it’s now looking at how can I use it to become smarter, how can I use, as Liz mentioned, to be my partner, my buddy? We know, we talked a while ago about AI augmentation, not replacing, but how’s the supplement. And these are the things that we have to understand. You know, as Dean mentioned, being technical is one thing, but now it’s become more of a leadership and executive. Now you have to become more digitally fluent. So if I look at this and look at how I can do it, how can I use artificial intelligence to help me reskill my thinking and the way I want to do and achieve my objectives. I’m shifting now from managing operations to shifting to managing risk and managing strategies. Those are kind of things that I think if we look at reskilling, those are things that need to be focused on. Because when you look at the careers today, everybody’s built now Careers are built on efficiency and execution. But now today’s environment, they will look at something a little bit more differently. Now it’s me more risk aware. I’m using technologies and tools and going into spaces I’ve never been into before. How can I adapt to these spaces and move into them without disrupting what’s currently taking place? How can I get quick responses and information to make better decisions? And how can I determine that uncertainty of things I don’t know about using this tool? So again, it’s a mind shift to figure out what do I need to do, how do I get there, and how can I use artificial intelligence to make that happen. And I think by looking in the context of the rescaling factory, that’s what we need to look at. I’m looking at everything, as you mentioned, from a cyber resilience perspective. And those are the kind of things I look at and how I had to retool myself. You know, I’m looking at the risk associated with these new tools and technologies, but also using cyber resilience strategies and leadership competence, not just an IT function. I’m using AI to help me get there.
[00:18:47] Speaker A: It’s a good point. I’m going to throw the softball out, Derek, that you introduce. I mean, a lot of what we think about reskilling is learning new technologies. And what you’re hearing here is a lot of just ways you’re applying yourself differently, ways of looking at your objectives and how you articulate them as being something very different.
But I’d love to hear, you know, Joe’s going to go next. I’m sure he’s going to talk about communication, leadership. John or Joanne or Elena. We should talk about the shift in technologies as well. Hello, Joe.
[00:19:24] Speaker E: So I’m actually going to talk about the question you asked originally. I think Joe, Liz and Derek have pointed out exactly right and build on what they were saying about focusing on, you know, building the business, developing ways in which you create value.
Initially in my career it was all about knowing the technology really well and picking up new tools so there there’d be new software, new applications, new techniques.
It was all about the technology.
At some point in my career, I realized that it’s important to leverage people to accelerate all the progress along the value creation, risk mitigation and business objectives. Whatever it was that you were trying to achieve, you had to become skilled in leveraging your people, bringing them along, training them, giving them the opportunity to use new tools, new techniques.
Now AI is on the scene.
I think of AI in much the same way as I think of a carpenter who was limited to using a handsaw, suddenly there’s a skill saw, it’s an electric saw and it’s got beams that allow you to cut straight or angles perfectly.
It can cut wood on its own.
How do I identify that, the technology component, how do I enable my people to learn how to use it and continue to accelerate the business through the use of these new technologies? So it’s, it’s AI in my view, is just another very powerful, very different kind of tool. But learning what tools are there, what they’re capable of, and how you enable your people to leverage those tools are really what the game is all about.
[00:21:21] Speaker A: Joe I love that shifting from being hands on to finding the people who are going to be the experts working with you and then, you know, your vantage point of guiding them, leading them, mentoring them is really smart. Hey John.
Welcome to the floor, John.
[00:21:38] Speaker F: Hey Isaac. Yeah, thank you for having me on. And I think as a society, like we’re literally all using AI right now. Like if anybody’s using a search engine, they’re using AI.
And so I think when people want to stay relevant, I think they really have to start looking at where things are going and kind of looking ahead. Like, how are the most innovative people using AI right now?
And I think it’s really important to start looking at what are the people that are most successful doing? Well, they’re plugging it into things and they’re having things run in the background. And so I think if you want to stay relevant, you can’t just be using artificial, artificial intelligence by chatting with it through like a web page. It’s like you have to, you have to start looking at the, the ways that are kind of like the next, the next evolution of it and start looking at how maybe you can have agents reading through emails and coming up with, with, with responses. Maybe you can have like live transcription going on your meetings and as people are saying things like have it, you know, ask you if you wanted to, you know, start looking into things. And so it’s, it’s so much better to like, look at where the puck’s going and try to try to like build your skills towards the puck’s going rather than just staying where everyone else is because that just, that won’t make you, you know, any better than anybody else out there.
[00:22:57] Speaker A: John, where’s the puck going?
[00:23:00] Speaker F: Well, so I was spending last night with a guy that worked at one of the frontier companies and it’s, it’s pretty interesting. He, he so he, he has. So like personally like I looked at my usage last night and I’m, I’m in for like 2000 credits on, on OpenAI and ChatGPT and it’s like I spent a ton on Fable last, you know, the last couple weeks when they enabled it again. And so like my, my credit usage for, for AI is a lot higher than it should be, but he has unlimited uses of it. So he has six agents running 24, seven basically. And so he, he has agents that run on his, his inbox that come up with proposed answers to everything that he agrees or disagrees. All his development projects, he has just continuous loops going on, on the tasks that he gives it.
Every time he’s in a call, there’s live transcriptions, it’s researching everything that people are saying if there’s a question on something that they can’t answer right now, it’s creating action items for things.
And so he’s able to kind of sit back and the AI is doing a lot of the heavy lifting. And I have some other friends that aren’t at the frontier companies but they’re kind of like at the very top of things and they’re doing very similar things. They try to figure out how to put agents in on the activities of their life and they’re very senior directors and so they have, you know, a director personality that goes through the inbox. Anything that looks like it needs a director’s decision or, or something like that, it gives a proposed response to and then if it asks if, you know, should I take action on this thing?
[00:24:25] Speaker A: Very cool, John. Let’s keep moving on to Joanne. Let’s hear about your mid career advice, any stories and let’s start pivoting into our discussion also on what leadership skills are needed for, for the AI era.
[00:24:41] Speaker G: Good morning. Thanks.
I guess my story would be I made a huge transition mid senior level career from being a CIO to becoming an industry analyst.
And that was a head turn in more than one way. And I, I don’t mean that to be egocentric at all, but rather to say that it forced me to look at technology in a much broader sense. And I think it’s one of the reasons why I still maintain that critical thinking skills and systems design skills are the way you need to move if you are in it as a leader.
It’s old stuff, but it’s now again new stuff. Because when you think about AI and when you think about agentic AI in particular, those agents that John was just describing are, you know, closed Loop workflows that get productivity enabled and you moving faster. But you have to start looking at things from the biggest, broadest arena. So from my own transition, I would say start looking at are you happy in the industry that you’re in? I mean, is this a job or is this a chore? Is it a job where you’re happy with what you’re doing, you feel fulfilled, etc. Etc. Or is it something that, yes, I have to go to work to earn a paycheck and that’s it.
If you start looking broader, then the AI tools are not only good thinking buddies, but they can also be your nemesis, your devil’s advocate, and, and use them in that respect because nine times out of ten, the frontier models are designed to, to make you happy.
You need to kind of take that layer away and say, don’t give me fluff, don’t give me bs. I want fact, I want to know where I should go and why, where those opportunities are going to be, how can I learn to adapt to them and go from an industry or something else that really you have, you know, even in John’s case, right, going into an area which is personal to you, which gives you great satisfaction.
This, this is the way I think AI should be used. It’s not just about productivity. Use it to unleash your own creativity because that’s the skill that will become in high demand. You know, we’re not at a point yet where everything is about one last mile. There are several last miles in AI. We’re not even close to the edge of it yet. But from that perspective, the more broadly you apply it to where you personally want to go, use it as a vision board, use it in a way that is going to give you an opportunity to be adaptable, to be broader thinking, to re. Engage in the linguistics of boardroom, let’s say, or executive, if you’re not there yet, and learn how to manage and leverage the capability of the technology.
You know, you can have agents running 7 24, that’s true, but they still require you to have some approval process.
There’s still governance that has to kick in. Use it for life governance as well.
[00:28:17] Speaker A: What I like this idea is picking an angle of creativity, you know, and being humble, that there’s always room to grow. That’s a good way of developing a partnership with AI. The other is just like if you’re mid career and you know you’ve only done industry or you’ve only done being a consultant, or you’ve worked for a software vendor, or technology vendor. There’s an entire ecosystem of opportunity in a lane that’s outside of where you started your career and you can be looking at the same work from a completely different vantage point.
You see it a lot with CIOs, right? CIOs, CTOs, they go from enterprise into some kind of advisory or sales function for a technology company or they become an analyst like the path you did Joanne, or they become an entrepreneur like what I’m trying to do. So lots of different opportunities there. Heather, love to hear about your advice for mid career leaders.
[00:29:28] Speaker H: I want to build on what Derek said about mindset because it’s a shift on how you approach your personal life and your professional life and recognizing what is it that you do well and figuring out again being creative, figuring out how that can be applied to something else. I can tell you for myself where my core is research. I applied that to executive recruiting now but what I did is I undertook my own research project to say okay, I want to get out of investment banking. Where do I want to make a difference in academia or in healthcare? And I embarked on an absolute research project to determine where I could go, what would be possible and made the decision that no, academia was not going to be financially appropriate for me. So I made the decision not to go in that direction. So sometimes what you find out is what it doesn’t work.
So if you’re going to be self reflective and, and have that sense of being self actualized then you can really start looking at I really don’t like what I’m doing, I want to try something else. And then when you open yourself up like that, you will find new opportunities and then of course the technology will help you do that.
[00:30:57] Speaker A: Super Heather. I mean it’s, you know, there’s a little bit of bravery that comes with that, particularly when there’s a down market.
You know, when there’s an up marketing you can say hey, I don’t really like what I’m doing or I don’t like my boss or I don’t like the culture here. And you could see lots of places that you can go to and maybe the recruiters are calling you up. It feels a lot more comfortable today.
I’m not sure everybody feels that comfort that they can just pick up, unplug and land somewhere relatively quickly. And so part of developing your competencies as a mid career leader is, you know, is, is going broader than who you are today.
Not just in your skills and in your learning but your ability to network.
I forget who it was I got a comment this week from from our listener saying can we cover networking during one of your coffee hours? We will have a topic in August around networking and give you a whole bunch of ways maybe you didn’t think of before to actually go out and network in today’s world. Before I take our break, Elena, love to hear about your advice and your leadership skills for the AI era.
[00:32:13] Speaker I: Thank you Isaac. So yes I’d like to focus on the leadership skills because I think what we are seeing is the familiar swim lanes in the corporate world are merging and the roles are becoming increasingly cross functional and the skills needed are becoming increasingly cross functional and therefore the KPIs have to be increasingly cross functional. So as leaders we have to come up, we have to understand that there is no longer a defined swim lane, that swim lanes merged. We have to KPI ourselves and our team against this merged swim lanes and one of the very important leadership behaviors and I’m representing commercial end of the spectrum here is to get commercial people to understand that in the age of AI the role of CIO and Chief Security Officer has changed and it’s no longer the team that we see once a year. It’s the team that we should be hand in hand with at all times because on the commercial end that’s where we experiment. We want to run pilots, we want to innovate and the most important thing is is to stay close to the CIO and the security officer to understand risks potential implications also applies to regulatory as well of what we’re trying to accomplish on the commercial side.
[00:33:48] Speaker A: Elena, I think you’ve made the statement of the day. Roles are increasingly more cross functional. I bolded it here that is going to create some angst with people who see themselves as X and X can be be a software developer, a tester, a content marketer.
These roles left and right of what you are doing are now collapsing into higher level more thinking, more strategic roles and this is why this conversation for mid career leaders on reskilling and becoming broader in what you’re doing is so important. I want to thank everybody for your comments today folks. This is dashboard and the slide that I started with will is available on drive.starcio.com Coffee please go visit that URL to see our upcoming events, to be able to listen to previous events, to get access to the leadership dashboards that I leave here and just be a part of the overall community again. That’s drive.starcio.com Coffee next week’s episode July 17th does IT leadership in the AI era require an IT background anymore. I expect a debate around that. We’re inviting Jason Goodyear to come and join us. He is an active, frequent listener. We’re bringing him on stage for this discussion on the 24th. I have an architect, Rameshwar Bengaluru, who will be joining us to talk about FINAI and managing AI cost, innovation, production and life cycle. This has come up quite a bit in this balance. You even heard Jason John talk about the rising cost of tokens and being able to manage that. So that will be our discussion on the 24th. And on the 31st, we’ll be talking about evaluating technologies in the AI era. How do we balance value, risk and ecosystem evaluation? That will be our 31st discussion. The links to all three of those, if you want to sign up early, are available@drive.star cio.com coffee. There’s also a button there to add all the events to your calendar so you don’t miss one. And if you do miss one, there are links to go listen to any of the events as well as being able to sign up for Apple or Spotify and listen to them on those platforms. So thank you for joining us. I want to bring Dean back and let’s shift gears. Dean, you’ve already given us some of your leadership skills. You talked about communication, data literacy, systems thinking and leadership. You can build on that. What other leadership skills you think are very important.
But I want to also pivot and start talking about how to make competencies visible and credible. And this is, you know, an increasingly more challenging issue. Is hard to, like, talk about soft skills on our resume.
And now our resumes are just AI food.
They’re not really what’s getting people jobs. Some of you will talk about, you know, your activities on social platforms, your activities writing and speaking.
Joe, myself, Liz, and I know Joanne all get involved in those different areas. Martin as well, Derek as well.
That’s not for everybody. So let’s talk about what the leadership skills we should target in the AI era, but then how do we make them also those competencies visible and credible, particularly as we think about expanding our roles, if you like your current one, or moving out and looking at other roles. Welcome back, Derek. Let’s go to Dean first. Hello, Dean.
[00:37:41] Speaker B: Okay, you want me as me. You want me to go?
[00:37:44] Speaker A: Yeah, go, Dean.
[00:37:45] Speaker B: Okay. All right. Awesome. Yeah. So one of the reasons. So I am working, actively working on developing a framework around something I call demonstrated competence. And I started researching this because this old traditional framework of how we get into roles that has been around for, I don’t know, 50, 60 years, however long it is because of AI and because of AI’s threat to human capital, we now have to find more tangible ways to demonstrate our competence and our abilities and our capabilities. And so making your talent and your, your, your skills legible to people is for example, what you’re doing Isaac, which is these live streams that you do every week. If anybody ever questioned Isaac’s ability to lead or to, to be in a IT leadership role, they would never question it because there’s enough evidence of his presence on the Internet where his presence on the Internet far outweighs anything that I could put on a resume. You make competencies visible by turning them into evidence and the resume in and of itself does not really do that thoroughly.
So what I encourage some of my, my mentees is that you now have to start being visible on the Internet. You need to start posting on LinkedIn through thought leadership. You need to present something. There has to be something more visible about you than a resume. Because now what’s happening is, and especially if you’re 45 or older, companies now are actively pushing out those mid career professions. We’re being filtered out. There’s a lawsuit with Workday right now that’s been talked about a lot.
They want this next generation of people to come in, you know, some leaders maybe, and I won’t make any assumptions, they may think or assume that they can replace a lot of us with technology. And we know that a lot of companies are quietly rolling that back as we start to see hiring tick up again.
So you, we, you need to be more visible. You need to present something, you need to build something, you need to talk about something. It could be a podcast, it could be, you know, what Isaac is doing here, which is phenomenal, but you need to demonstrate, show people what you can do, talk about your passions and skill sets on the Internet and build a brand. We are, we’ve talked about this a lot about brand building. A lot of people don’t do that. Folks are just accustomed to updating a resume, applying for a job and just sitting back and waiting for somebody to come get them that is dying.
You need to be out front and you need to be visible.
[00:40:36] Speaker A: Thank you, Dean.
Looking for more ideas of skills and how we make them visible and credible. Go ahead, Derek.
[00:40:44] Speaker D: Yeah, some of the skills that come to mind and Dean was spot on with the things he mentioned, but I think leaders in the skills they need to learn become more comfortable with constant change. AI is bringing now New elements we’ve never experienced before at a faster pace we’ve never experienced before. I think also as we’re looking at this leadership skill, leaders need to become more AI literate. You know we talked earlier about The Claude, the ChatGPT, the Co Pilot, all these different platforms that exist, they all have variations but some similarities across them. I think also when you look at the leadership, we need to look at the resilience thinking and the new strategic way of thinking. And I think what Dean mentioned earlier, you know, the things that AI is trying to replace, we as leaders need to focus on those human skills, skills that machines cannot replace. We need to look at the emotional intelligence, we need to look at the trust building, we look at the critical thinking and most of all the ethical judgment. We still talk about human in the loop, that those things are required and now these things will become a competitive advantage for those people that are entering the marketplace because they can’t fully be replaced. And those are the things I think we need to focus on when we’re looking at how can we continuously learn the new habits and traits, but also in doing that, what things are going to be resonating. We also have to be comfortable with being uncomfortable. We have to know there are going to be challenges, there are going to be risks that AI is going to be bringing to us. And leaders need to understand and to what extent and how that may impact their organization or them personally. These are all things that we need to understand. The business impact, it’s not just a technology decision, but it’s a longer business impact decision. And by looking at this and how it’s going to affect the operational resilience, the customer trust, the revenue protection and the organizational reputation, these are the hardest things we need to look at at a deeper dive and not just on the surface because when you drill down into it, there are things that are relevant and will stick out, but we just can’t say automatically as companies, as Dean alluded to, we’re going to replace so many people in our workforce because AI is going to do it. Companies have tried it and has not been successful. So we got to think a better way of how can we do this. Better crisis leadership skills are going to be still important. I can only do but so much moving from prevention to recovery type mindset, those are type of things we need to look at because AI is going to bring challenges to us that we haven’t been exposed to before.
We always talked about working along AI. We need to figure out how we can do that better it’s one thing to say it, but are you training to understand what does that really mean? So there’s a list of things we can go through, but I think at a start from leadership perspective in this AI era, those are some things to consider.
[00:43:07] Speaker A: You know, Derek, let’s, let’s go one level deeper with you.
If you opened up a, a role or somebody that was, you know, let’s just say for argument’s sake, was a cissp, you know, security professional, you’re going to get, you know, 500 resumes sent to you with a whole bunch of other Alphabet suit of credentials and things like that. And you know, let’s say there’s 10 of them, you know, in front of you that you’re talking to in a group setting or something like that. How are you going to know like what has somebody done to say not only have they gotten the certification, but they can clearly show they’re competent and they’re credible in the subject matter area that they’ve learned.
[00:43:56] Speaker D: So I, I think from an executive point of view, I’m going to look if the certifications are valuable and that’s a nice flag because it puts you or elevates you that much higher in the, in the, the pool as far as potential hires. But also I think they look at, as you mentioned, the AI competencies. What have you done, what’s been visible, what credibility you can show me as a professional that you understand how to use AI for business outcomes, use AI to reduce business risk, use AI to improve efficiency. Those are kind of things, I think even as those people in college, not just those that are experience in mid level, but how are you looking to understand and interpret and engage in those processes? How are you looking to use AI to make better decisions? We talked about critical thinking earlier. How am I doing measurable productivity gains? So I ask myself, if I’m looking at this and I’m looking at you as a candidate, what problems have you solved using AI? What’s been the measurable impact you’ve been able to achieve using AI? And what organizational learning have you been able to bring to your organization, even to yourself using AI? I’m looking at those things that are beyond the credentials and by that it gives me better value because as I mentioned earlier, to be able to adopt, to change is going to be a key thing. And that shows me you’ve got done a little bit better than just got you the certification. You’re now using it to be tangible and show results that’s going to give you more credibility and it’s going to raise your, your score as far as being a possible candidate with me.
[00:45:14] Speaker A: Awesome. Thank you, Derek. Liz, Skills and how do you make them visible and credible?
[00:45:21] Speaker C: I love it. So just, I want to build on something that Derek just said because the question that you toss to him is extremely relevant. In the millions of years that I’ve worked in project management. Right. The pmp.
The pmp. I used to tell people the PMP means actually nothing.
That certification means nothing.
[00:45:44] Speaker G: It’s.
[00:45:45] Speaker C: It’s just something that you passed a test. We have somebody that you bring into an interview that you really want to be running some project, work for you, program work for you.
Throw a problem at them, let them talk through how they actually solve that problem.
Put them in a situation. That’s the way to really understand how people think and how, and really how they would leverage AI.
And if you think about it, if we go back to the what skills do I need to learn? It has to do more with. Are you interested in moving upstream into the business world of strategy and market share and profitability? Are you interested in the technology and really moving. I call that downstream. Moving into the architecture of what it’s going to take to actually support all these amazing tools. I recently published an article, is AI the death of It? And when I brought that out in this call, people were like, laughing me off the stage. But it really is about moving away from the traditional roles of IT and moving hardcore into the architecture world or moving hardcore into the business world. And in either of those situations, you can actually leverage ID to act to tell you what you need to learn and do to actually build those skills and actually make progress in that career path.
[00:47:07] Speaker A: Yeah, Liz, you and I are saying the same to them this time around. You need to be able to tell the story.
Right. It’s, it’s not the facts. It’s not the certifications.
It’s. It’s. It’s not even just outlining your experience.
It’s being able to answer, to have a conversation about what you’re, what you’ve learned and what you’ve accomplished. And it’s particularly important when you’re starting to veer into areas that you don’t have expertise in yet.
Right. So it’s sort of like a how do you tell the story before you have a story type of problem? And that requires some work. Let’s go to Joanne.
[00:47:48] Speaker G: Okay, so, so here’s a really good example of how you take a skill set and bring it into a broader situation, make yourself demonstrable so our principal architect, who’s an extremely wizard like person, like pulls rabbits out of hats all the time, very, very competent, extremely valuable, also has a passion for music and making videos and studied to be an artist, et cetera, et cetera, and leverages open source to show some of his skills. He just put something out the other day which is about video clips. We all struggle with them. We all. It’s a little utility program, but that’s a perfect example of how you demonstrate your overall ability and your overall capacity. You can point to things like that to say, this is how I adapted my day job into my passion or my passion into my day job. And I think that framing of creating a little video utility that is gaining a lot of attention because it is just the. A simple fix to a really big problem that everybody seems to have is a way for people to demonstrate, hey, this is my expertise.
This is where I’ve applied and adapted my expertise to a real world problem that everybody seems to have, that nobody seems to think about until they have the problem, which is putting video clips together, that they look seamless and transition beautifully, etc.
So that story is what I would say is the way people have to distinguish themselves. Open source is a great community. It’s huge.
Whether you contribute to it or just explore it and comment about it. That’s a way to give you a path to show more than just your expertise, which can be, and I don’t mean this to sound disrespectful, but a dime a dozen because you have a cert.
It’s how you apply your knowledge and your perspective to bigger problems. You know, when I talked previously about the transition I made from being a corporate CIO for a very large enterprise into being an industry analyst, it was a head turn like nobody’s business. Because what used to be memos and documents of length had to be newsworthy items in 35 characters or less.
That’s a mindset shift. But the whole notion of being adaptive and adaptable, it’s developing a new set of lingua franca for yourself. It’s using your creativity to showcase what you are capable of. And it’s also something that has lost a lot of credibility but now goes to what’s called authority. And that’s thinking quickly on your feet.
And that’s a skill.
And that’s a skill every leader should develop. You can’t sit and not have an answer, even if your answer is I’m not 100% sure and need to do more research. But my gut is Telling me blank. That’s a way that showcases your experience, your expertise and your ability to adapt all in one shot.
[00:51:13] Speaker A: Love it. You know, Mariella has this comment on here. I don’t know who wants to say something about this. And it’s like, you know, we’re talk. I agree with what Les said, right. It’s not about the PMP or the cissp. It’s being able to articulate how you have or how you’re going to be able to apply it. But she couldn’t even get through the door. I was told by three HR recruiters that I could not move up on the inter process because I had not had a PMP cert. I will tell you, Mariella is one of the best product program manager architects that I know and it would be completely meaningful, meaningless for her to have a PMP certification. And yet our recruiters are still trained to look for, you know, an Alphabet soup of certifications.
And I’m not just picking up bnb. It could be all could be a safe agilist. I don’t care.
It’s all over the place and we still haven’t gotten people looking beyond the acronyms and looking into the people. So Heather, that’s the prompt for you. How do we make sure that our expertise is visible and credible?
[00:52:23] Speaker H: It’s both something that you do inside your organization while you’re currently working as well as outside. I can’t emphasize enough the importance of being visible.
It’s been said here before and Joe is queued up and he’s going to most likely talk about communication, how you communicate internally.
I know a bunch of millennials, including my own children, who create a 5:15 document every week.
They tell their boss, their immediate supervisor, what they’ve accomplished that week, what their priorities are, what their challenges are. Business leaders are not mind readers. So unless you communicate and tell them what’s going on, both the good and the bad, and if you can’t promote yourself, then nobody else will, so that’s really important.
And then outside the organ, there’s no question that being visible, there was a feeling that I had several years ago. Does anybody really care what I have to say?
And when I started pushing myself and putting more and more thought into what I wanted to say, I was amazed at how many people liked what I said on LinkedIn, would comment, would have a conversation, would develop this whole communication with me back and forth.
It’s just a fear, you know, potentially. But you’ll find that what you have to say is interesting. And the more that you feel good about it, the more others will feel good about it. And I think Joanne’s example of the passion that someone has for their role, her engineer, their passion, their personal passions, why shouldn’t that be shared? Because we are not singly dimensional, we are multi dimensional. So the more that you can share when you do get that interview and you will, you’ll be have more to talk about.
And then we have not lost sight of a resume yet.
So anything that’s on that resume has to be quantifiable. Dollars, numbers, percentage change, say what you’ve done. A laundry list. That’s what the job description is. Do not just list. I did this, I did that, I managed. You have to show where your impact is because when someone does read it and you’ve got to get them to do that, make it compelling, they’re going to say, ah, that’s what I need. So you want to be the one that is doing the job currently that they need for the future.
[00:54:53] Speaker A: Thanks, Heather. I can’t believe how fast the time has gone, so I’m going to go straight to Joe. Joe, how do you make competencies visible and credible?
[00:55:01] Speaker E: Well, Heather stole my thunder as usual. You predicted accurately that my watchword would be communication.
And communication is bi directional. It is absolutely a massively critical skill from, from start to finish in your career. Learn how to listen to people and learn how to talk to people in terms they can understand. Dean mentioned your brand, building your brand. You, you guys know how high I am on this whole notion of having a personal brand.
Every week I counsel people on how to represent their value through their personal brand. You must be able to communicate and, and how you communicate your brand is how people are going to see you. They’re going to think about. Well, Derek is all about resilience.
Heather’s all about people skills. You know, it’s, it’s what you talk about and how you talk about it that creates your personal brand. So I would say sharpen your communication skills. You’re going to need them when you’re explaining AI to the board. You’re going to need them when you’re motivating your staff and you’re going to need them throughout your career to make sure people know who you are and what you can do.
[00:56:14] Speaker A: Joe, there’s a really important point about what you’re saying. If you’re at that dinner party and somebody asks what you do and your answer is, I do X job for Y company, you need some help in this area, right? That’s what you’re doing. That’s who you are right now. Maybe it’s at least what your job title is and where you work, but it’s not who you are. Right. And so when we say personal branding, it doesn’t mean go out necessarily and you know, become an influencer, thought leader. It means know how to answer that question and know how to represent it on your LinkedIn profile.
[00:56:51] Speaker E: That’s exactly right. And we spend an hour every Thursday morning with a group of people from, from SIM Sim members talking about that very point. That when I ask you what do you do? The answer is not. I’m a senior IT professional and I have expertise in transformation skills and AI.
That, that means nothing to me. What I want people to say is I’m a chaos to order guy. I take messed up IT departments and straighten them out. Boy, anybody can understand that. And that represents your underlying skill.
[00:57:24] Speaker A: There you go. I was hoping you’d give your, your one liner because everybody needs to hear that and how well and polished you are in saying it and answering it. John, I’m giving you the last word today.
[00:57:37] Speaker F: Thanks Isaac. And I, I sometimes see people say like this one is the best or that one’s the best. And I just, I encourage everyone to go out and, and try as many of these tools as possible and, and look, look at, at some of the advanced features of them and, and just try them out in a safe environment and because you know, we don’t do anything dangerous but it’s, and then try the different tools and see, see how one compares to the other one and put the answers from one tool and the other tool and, and just there’s so much really, really neat stuff you can do on a shoestring budget. It’s a free tier and, and once you want to start spending money or if you can get your companies to pay for it, there’s all sorts of amazing stuff you can do if you got a lot of credit. But yeah, there’s, it’s just like a whole new technologies got dropped on us and there’s, it’s like so many things that people haven’t even discovered. So go, go discover some neat ways of improving your workflows and your life and all the stuff going on at your company.
[00:58:30] Speaker A: Thank you, John. Thank you, Dean for being our special guest today. Joanne, Elena, Heather, Joe and Liz for joining as our speakers. Great episode, folks. I think what we’re talking about here goes well beyond how you position yourself and the skills that you’re learning, how you make them visible. Incredible. I personally believe that every one of us will have to reinvent who we think we are over the next few years. And I am deliberately dropping a hint around something. If you want to know more about it, reach out to me. If you’re struggling with being able to reinvent yourself, please do reach out to me. Folks, this dashboard will be up later today atstar@drive.starcio.com Coffee.
My original research slide will be up there. If you missed part of today’s episode, you can listen to it. That link will be up there.
If you want to listen to previous episodes, those links are there. Again, it’s drive.starcio.com Coffee Next week we’ll bring Jason on as our special guest. Does IT leadership in the AI era require an IT background anymore? The 24th we’ll be talking about Fin AI and managing AI costs, how we balance innovation, production and life cycle. And on the 31st we’ll be talking about how we evaluate technologies in the AI era.
I do accept recommendations for speakers and recommendations for topics.
Next week I will actually announced the August topic, so if you have any that you want to recommend, please do reach out to me. Folks. Everybody have a good weekend. Stay cool and enjoy the soccer. If you’re a soccer fan, I’ll be back here with everybody here next week. Again, it’s drive.starcio.com Coffee everybody. Have a great weekend.

























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