Finishing Strong: How Digital Leaders Close Out the Year

Summary

This was the 193rd episode of “Coffee with Digital Trailblazers,” marking the show’s fifth year of discussing leadership in digital and AI transformation. The main topic focused on how digital leaders can finish strong in 2026 to ensure a successful start to 2027, covering three key areas: building vision and strategy, avoiding Q4 security crises, and taking care of teams while managing personal well-being.

The discussion included insights from multiple experts including Isaac, Joseph, Heather, John, Derek, Elizabeth, and Joanne, who shared advice on celebrating successes, managing risks during the holiday season, handling difficult stakeholders, and maintaining team morale during the busy Q4 period.

Key recommendations included implementing regular governance processes throughout the year rather than just at year-end, establishing clear escalation procedures for security incidents, setting firm cutoff dates for new AI agent deployments before November, and focusing on specific recognition rather than general praise for team members. The episode also highlighted the importance of maintaining calm leadership during stressful periods and ensuring proper preparation for the post-holiday transition into 2027.

Speakers

• Host – Isaac Sacolick
• Digital Trailblazers – Derrick Butts, Martin Davis, Joanne Friedman, John Patrick Luethe, Liz Martinez, Heather May, Joseph Puglisi

Discussion

1. Build the vision: You’re coaching a Digital Trailblazer whose 2026 brought real AI and innovation wins, along with underperforming initiatives with dissapointed stakeholders. With 10 weeks left in the year, what specific actions are you coaching them to take so stakeholders head into 2027 enthusiastic about the budget and plan?
2. Avoid a Q4 crisis: A Q4 security incident can wipe out a year of wins, and it tends to hit when teams are running on skeleton crews. What added precautions should risk leaders take to finish the year strong, especially around the AI tools and agents they rolled out in 2026?
3. Win as a Team: After a stressful year, what specific steps should leaders take before the holidays to recognize their teams, recover their own energy, and set everyone up to start 2027 strong, rather than burned out?

Research

Transcript

[00:00:00] Isaac Sacolick: Greetings everyone. Welcome to our 193rd episode of the Coffee with Digital Trailblazers. Our fifth year, I had to go look this up. We started our first episode, four years of losing my mind on math. But we started it several years ago, four years ago, this is our fifth year and it was at the end of September. And if you don’t know the story, LinkedIn launched their audio program.

I turned it on. I had about 20 people joining. One of those people is Joanne Friedman. She has been here all but one episode and that’s almost all 193 episodes. And here we are starting our fifth year.

And if you don’t know the program, we have discussions for those of you leading digital and now AI transformation in your organization. And we will be here for at least another year doing this, trying to help everybody run transformations in your organization, run AI in your organization. Do it in a balanced way between innovation and resiliency and taking care of yourself and your people along that journey. And that is our discussion today, almost in summary format. Right. I wanted to have this discussion. Here we are mid October, heading into the holiday season and get some advice for all of you about how we finish strong, how digital leaders close out the year. What does that look like so that we don’t burn our teams out, that we don’t have a hiccup at the end of this year that causes us to get off next year off to a left footed start.

And how do we close out what we promised and said we would do this year and make sure that our organizations are ready for next year’s new challenges? So that’s our talk this year.

Let me bring up some research I’ve done around this today.

First, on the value side, the left side of this slide is giving you some of the areas around value. The right hand side is giving you some data points around risk.

On the value side. This is very interesting. Three different surveys with very different findings around the value from AI.

At the top half is this KPMG global survey saying 89% of organizations report measurable value from their AI. That’s a global study, but somehow the US is only at 58%. And I have to guess this is both KPMG studies. I have to guess this is either the same survey, you know, segregated by us, or maybe two different surveys with the same question. But this is kind of astonishing to me that 89% in the world says we’re getting value, but somehow the US is underperforming in that the opposite side of this is coming From Gartner says 13% of CIOs say their enterprise has realized significant or transformational value from AI value. That means 87% of you have not. You’re getting either no value or tactical value, incremental value, productivity improvements, the things that really just don’t meet the move the needle. And so we’ll talk that as a backdrop. How do we finish off what we committed to this year and get off next year to a bank? And for those of you who don’t update your strategies frequently enough, chances are what was in your strategy and in your roadmap January of this year probably needed several updates because we were just getting started with agents this year. We, we were just learning how to do AI code generation this year. And that has accelerated significantly over the course of the year. Only 17% qualify as AI adoption leaders.

This is coming from Creatio’s recent study. And organizations automating more than half of their workflows with AI are more than twice as likely to report increased revenue as a positive impact of AI as those automating less than 10%. So in other words, if we’re automating more with AI, we’re more likely to see increased revenue. This is what the CREATIO study has reported on. I think that’s very interesting. I think that what’s happening there is as you increase AI literacy in your organization, it might start at productivity and efficiency, scalable operations, and it’s going to bleed into areas that drive confidence on the front end of the house and increase revenue. Now, on the right side here, I didn’t know this, kind of interested on Derek’s read of this chart. But this is.

Claude helped me put this together from obviously a number of different studies. You could see all them linked at the bottom and they talk about reported ransomware attacks by quarter. And what you can see in the orange bars is there’s a jump up from sort of a quiet Q2 and Q3. And then all of a sudden there is a bump up a 32% increase in 24, a 48% in 2025 going into Q4.

And I think part of that is, you know, the incentives are larger. I think it’s harder for organizations to respond during Q4 when there’s plenty of other things they have to worry about.

I think the bad guys know this and they just step up their efforts during a time when companies are more vulnerable. And so part of this discussion today around finishing strong is recognizing that, right? If we have a blow up in Q4, whether it’s in our, whether it’s in our programs or in our security or in our operations, it’s going to be having lingering effect until our Q1 start and prevent us from going after all the things that we’re promising our management teams, our boards, our customers, and really getting us, you know, backpedaling our way through our plans into 2027. So that’s our conversation today. Finishing strong, how digital leaders close out the year.

I have my two hands raised already. John and Derek are up there ready to talk about this. I want to say hi to everybody who’s here joining us, Carla, Don, Daniel, who else is here? Chalpati Craig, talked to a couple of you guys this week. It’s great to see all of you here.

I have celebrated my 10 year anniversary at Star CIO.

Almost 1300 articles, 4 years of doing coffee with Digital trailblazers. Some of you saw me post around that yesterday. Thank you for all that and thank you for my team here, my colleagues and friends, for being a part of this coffee with Digital Trailblazer all through this year. So let’s talk about building the vision First. John, I want to put you in the role that you’re coaching, a digital trailblazer whose 2026 brought real AI and innovation wins along with some underperforming initiatives that probably disappointed their stakeholders. We’ve got 10 years, 10 weeks left. 10 years, 10 weeks left. What specific actions are you coaching them to take?

So stakeholders, head into 2027 and think enthusiastic about the budget, meaning what was prioritized, what was planned, and be your supporters getting off to the year and off to a good start. Hello John, welcome to the floor.

[00:07:53] John Patrick Luethe: Hi Isaac. Happy Friday and thank you for having me on. I think, I think what’s really important for people to do is spend some time reflecting over the last year and looking to see what was successful and looking to see where they didn’t get the success that they wanted. And what I have seen looking at a lot of companies is that companies have gotten pretty good AI efficiency gains without doing comprehensive change management and without really looking at the way they’re using AI both in their systems and in their organization. And so I think starting with some reflection on kind of what’s going well and what’s not going well. And then I think almost everyone I talk to has come to the conclusion that if you want to use AI in your organization, it’s like putting a big ERP system in. It’s like it changes the way you work. Right. And so I think it’s it’s really important to try to think about, you know, how do you want to use AI in your organization? Like where do you want to use it and what processes and what, and what are the systems. Right? And just, and, and from there build, build a plan so you can get what you want with this and so that you can, you can have, you know, if you don’t like the word change management, do change management and call it something else. But basically, I mean it’s really, really important to, if you want to, if you want to get something going, it’s not enough to have the tools. You have to figure out how people use the tools. You have to do enablement activities, you have to do communication activities, you have to do coaching activities. But do a multimodal to get this thing going and really get the value you want.

[00:09:21] Isaac Sacolick: John, what are you coaching? The digital trailblazer who has a thorn in the portfolio and needs to know come to make ends meet before year end.

[00:09:35] John Patrick Luethe: Well so, so, so I, I think it’s always important to say like look what is the highest priority right now? And when I read the news I, I, I think what was the highest priority last week and what the highest priority this week is probably really different. Right. Honestly. And so I just, I always recommend that people look to see like of all the work like what do we really got to be focusing on and, and just get to crystal clear what we’re focusing on. Because with, with AI have I hear about so many companies saying that oh we can build anything, we can build everything and it’s like no focus on what you’re not going to do.

You just, and just like put those conversations away like we’re not even going to talk about those things. But what, what, what is the most important thing that we have to do? What’s the most critical thing? And put all your efforts there and then actually build a plan for the rest of the year so that you actually are getting, getting what you want. Like build, build a plan, figure out how to get it.

[00:10:24] Derrick Butts: Derek.

[00:10:25] Isaac Sacolick: Thanks John. Derrick, I know you want to talk about Q4 crisis, but we’re going to talk about building the vision first and I promise you when we bring up the crisis, we’ll bring you up first for that one. So go ahead Derek.

[00:10:36] Derrick Butts: Sounds good. First of all, congratulations for the number of episodes that you’ve done in your 10 year anniversary.

[00:10:40] Isaac Sacolick: Thank you.

[00:10:41] Derrick Butts: Awesome. So when I look at this, the points that John brought up are great. The fact that reflect to see what worked, what didn’t but I don’t think I’d really be focused so much on finishing strong the end of the year. I’d be looking at what are we prepared for, what’s coming next year. And I think in looking at that, we do have to take a look at as far as what worked in the previous year. So when we looked at the separate outcomes from the activities, we’ve hedged our bets, we made all these investments. What worked and what did. If I put in, you know, large amounts of money investments to these AI tools and these AI services, how many of those actually were successful? How many of those actually showed an ROI based on what we’re doing? I also look at the fact that we’re looking at, you know, the budgets, what’s been outcome, the resilience more this. What’s the business been building as far as capability to protect and scale and improve the things that we’re doing and doing as well, while reducing the amount of risk. I’d also look at the wins behind what we’ve done well, when we’ve done this, what actually enabled us to do the things well that we’ve done. What are the business success, what’s the data access, how have the models changed, what have been critical when it comes to employees leaving, going through this effort? I’d also look at kind of a model, I said, look at what we’ve proved, look at what we’ve learned, look at what we’ve been able to stop as far as risk concern. Look at how we’ve been able to scale utilizing these tools, and what are we looking to protect moving into 2027? And I think in breaking it down in that simplistic format, it makes people kind of think of all the different elements, aspects between the technological investments, the business culture investments, the training, all those things that are taking place. It makes it come back and say, what can we do now to finish strong based on where we’ve been?

[00:12:13] Isaac Sacolick: You know, Derek, you went in front of Joe and you’re preaching communications, and so it’s that fair. We have to talk a little bit more. So Joe comes back with another area to focus on. But I like this idea of not dwelling on what didn’t work.

You’re obviously going to have to talk with your stakeholders who are in that camp and disappointed. I don’t think you can avoid them. But when you talk about the greater organization, I like, you know, pointing at the future, what worked, and then instead of talking about what didn’t work, I think what you’re getting at is talk about what you learned, right?

[00:12:48] Derrick Butts: It’s all from a resilience mindset. What have we learned based on being able to do these new things without increasing our risk in doing it?

[00:12:56] Isaac Sacolick: Got it. Go ahead, Joe. He took your communications line so well.

[00:13:00] Joanne Friedman: He.

[00:13:01] Joe Puglisi: He did and he didn’t. I’m gonna, I’m gonna first give you my comments grounded in my philosophy about the B before the T. You all know the story, right? It’s called BT not it. Because the business is more important than the technology.

So in my year end staff meeting, when I get the team together, the whole team, it’s usually a town hall, the first thing we talk about is measurable impact, much like the surveys you cited. What did we do right this year in the eyes of the business?

I know we got all the software patches in on time and, and the firewall was replaced in under 24 hours without disrupting the network. Yeah, that’s great. But let’s talk about what did we do in terms of revenue, ebitda, customer satisfaction, external customer satisfaction, as well as internal customer satisfaction. So a lot of measurable things that we’d like to talk about. And the first and most important is let’s collectively celebrate those successes. We. Let’s talk about what went really right this year. We planned it, we executed. It worked. It had the right kind of outcome. Second, let’s be honest, we planned a few things that didn’t work as well as we expected. And much like Derek just suggested, you know, there are lessons to be learned. It’s not taking someone to the woodshed, it’s going to school on what we did that didn’t pan out the way we expected.

Was it something we could have done different? Was it software that didn’t live up to the expectations or the, you know, the proverbial demonstration that always works.

And then third, I like to allow the entire town hall audience to identify winning moments. What did you guys feel best about this year? And maybe there is some technology improvements or, you know, new piece of software that somebody introduced that really worked well.

So we talk about winning moments as a way of bringing spirits up and keeping everybody positive. The last thing is not necessarily in that meeting, but in accordance with my golden rule number one, I always want to be the first to know when something went wrong. If I’m aware of something not only at the end of the year, but throughout the year that has gone wrong, I’m the guy who’s going to go to marketing or finance or the chief operating officer and say, hey, this is messed up. We know and we’re working on it.

Kind of reflect on that over the course of the year when you meet with business leaders, other business leaders in the organization. Let’s talk about how well we communicated. Yep, there’s the C word. How well did we communicate throughout the year?

Not only when things were going right and we were beating our chest with pride, but when things went awry and we were on top of it and took care of it to continue to build that relationship, that trust that you need from the rest of the leadership team.

[00:16:01] Isaac Sacolick: You know, of all the great advice you have here, Joe, I think the one everybody listening needs to put on their radar is celebrating successes.

I just think that you’re not going to bet a thousand.

Even with good communications, even with good, well defined success criteria and targets, you’re going to have some hits and some misses.

When you create a culture that celebrates successes, it’s really hard for your stakeholders to just create a negative vibe.

It doesn’t look well on them. Right. When you have seven programs that delivered revenue and growth and efficiencies and demonstrated value from AI and you had three misses.

Right. You know, whatever those are, it’s really hard to have the stakeholders in those three misses be able to go to the megaphone and say it’s been a bad year and spoil what was a good year and prevent you from getting your next year off to a good start. So I think that’s. There’s plenty of time here. It’s October 23rd.

Even if you’re having a holiday party, that’s a holiday party, right. Find the opportunity to say, look, we’re going to bring some people together and say we did some really good things here. Go ahead, Heather. Welcome back.

[00:17:27] Heather May: Thank you.

I would just add also to what Joe just said.

Yes, celebrate the wins, but learn, make new mistakes.

The comments that I have relate to the time of year.

Just because it’s the end of the year, in some ways, you want to forget about that. So you should be doing consistent intentional actions and consistent incremental budget reviews and don’t let the enthusiasm at any point during the year overshadow any of those consistent activities. So, you know, yes, it’s the end of the year and there’s more to look at. But if it’s going, if you’re having these activities all year, then the end of the year is just another one

[00:18:15] Isaac Sacolick: trying to not look at the end of the year as a special point.

I don’t know, Heather, I’m probably going to disagree with you that one. I mean, I Think in logic, sense. That makes sense. But we’re all trained on looking at New Year’s resolutions. Our businesses run on four quarters with budgets being set right now. There’s always a debate about what’s getting funded going into the end of the year. Q4 just is, you know, one of those difficult periods where a lot of things come together. I’ll let you. I’ll let you feedback on that.

[00:18:53] Heather May: Yeah, I think, yes, in terms of the content and the information that you’re getting, but it’s the process.

You still have to be consistent. You still have to look at the reviews, the view of what happened in the previous quarter and how that impacted the future. But it’s not like, oh, it’s the end of the year, let’s rush to do X, let’s try to do something different. No, if you’re consistent, then you are calculating, considering everything that happened in the previous quarter, the previous month, whatever, and you’re just collecting all this information. But make sure that the end of the year shouldn’t stop the. The process you process that you’ve been doing all year and be intentional and not rash.

[00:19:35] Isaac Sacolick: Got it. You know, for those who were at the FW SIM event a couple weeks ago, Joe was there. I know. Carl listening here, she was there.

You know, I told people they needed to keep meticulous notes and keep meticulous data. And part of that reason is when you get to the end of the year, right. And people have short memories, you need to be able to go back around what decisions were made when what things happened out of your control. Where did you have some successes along the journey that people forgot about?

And you got to be able to tell that narrative and have the data around that narrative. And I think that’s what you’re getting at. Heather, Joanne, I’m sorry about the delay getting you on. I clicked a couple of times, finally got you here, so I’m thrilled you’re here. Our 193rd episode. I was telling everybody in our four years plus of doing this, I think you missed all but one episode. Maybe.

And I think it’s. I think it’s a maybe. So we’re talking about building the vision toward next year, making sure we finish off this year strong so that we’re not starting next next year with our hands tied behind our back and our ankles shackled because of something we missed last year. I’d love to hear your thoughts around that.

[00:20:57] Joanne Friedman: Well, I think I have five lessons and I’ll make them brief each. First of all, lead with Truth, not a victory lap.

And I, I say that with all sincerity, not because I don’t want to celebrate wins, but celebrate the measurable ones. Own the disappointments and explain what you learned. I think the thing that most leaders don’t want to own up to is where they failed. But if you turn that into a learning moment, it’s much better for your team, it’s much better for the organization. And stakeholders really will forgive a setback than a, a spin, right? Credibility is always your best investment.

So that would be the first. The second is make the hard calls, you know, scale fix or stop double down on what had value, what proved that it gave value like AI or not AI because only 11 of the pilots actually made it into production and are being run in any significant way. So shows stakeholders that you’re invest with discipline, not just defunding sunk cost.

The third, I would say is try and deliver one meaningful win. Yes, there’s only 10 weeks left in the year, but you can pick something small, visible, measurable and somewhat important to stakeholders. You know, if you’ve disappointed a particular group, if there’s anything possible to do that’s not like a band aid that appears like a band aid, try and deliver it.

Make your co owners by the way, your, your stakeholders should be your co owners for 2027. So bring them into the fold now.

Finance, business, I t team itself, agree on the outcomes, the priorities, anything that is that you are able to do for people support, do it.

Build the 2027 budget backwards. You know, I’m big on reverse engineering from business value or realized value. Tie every single investment that you’re going to make to revenue to margin, ebtida resilience.

Invest in your cyber security, particularly if it’s PHP related, as we all well know.

Establish your milestones.

But really you don’t rebuild confidence by promising a better 2027. You rebuild it by demonstrating better judgment in the last 10 weeks of the year. Because the next budget isn’t a reward for what you tried, it’s an investment.

It’s an investment in what you’ve proven you can deliver. You will deliver according to plan. That brings all stakeholders, regardless of who they are on your team or in the business, some form of a better quality of work, a better quality of life.

[00:24:06] Isaac Sacolick: Thank you, Jaron. We’re going to bring Liz up for our last part of our discussion on vision. Then we’re going to talk about avoiding a Q4 crisis ready and giving the baton to Derek to be the first comment around that.

Liz, I’m going to give you an open mic around this one. I’m kind of interested which part of this question you’re going to respond to.

[00:24:25] Liz Martinez: Well, I, I love what both Heather and Jim were talking about in terms of honesty, openness, making sure it’s a regular pattern of reporting that it’s not just a year end thing. God forbid we should go back to the old days where we actually had status reports and quarterly reviews, et cetera. But that’s, that’s really my mantra as part of value realization office. But I want to look at something that, let’s see, Wayne Anderson was saying in the comments about trying to run at the end and chase back ROI measurement is just a disaster.

And this is really where I know nobody likes to use the word governance. Governance is not a four letter word.

But this is all about making sure that if you put in the structures in advance and you are collecting that data all throughout the year in status reports, monthly reviews, quarterly reviews, making sure all your ROI is set up in advance that you actually know how to, how to measure it, then you can move into this fact based reporting like Joanne was talking about. The only caveat I have is it, it does depend on the culture and if the culture is open to making sure we’re talking about quote unquote mistakes in terms of learnings, that’s the best type of culture that you can have. If the culture is one where mistakes need to be covered up because someone’s going to get their head blown off if they talk about them, then you have a different type of problem anyway. But having said all of that, the lead into the next section which I know is going to be all, all Derek’s arena is the future looking preparation for 2027 is going to be all about preparing for you know, cyber, AI and cyber. It’s just, it’s, it’s that looming, it’s looming on the horizon. Actually it’s hitting already but I’ll turn it back over to you.

[00:26:34] Isaac Sacolick: Thanks Liz. You know I do have a question for you and if we can can’t get you back to talk about it, maybe you can put it in the comments. There’s always one program, one stakeholder, you know, that is just, you know, you know, undermining the entire portfolio success and the downer and you know, if that person is, is, you know, three levels down the totem pole, maybe not so important if, if they’re, you know, a key voice into the CEO’s ear, we’ve got a problem. So I may bring you back if not put it specifically around that. When we talk win as a team, think about how you’re advising digital trailblazers around that one program, that one stakeholder. That’s just spoiling the message when you had a good year, right. Particularly this quarter. So give you some time to think about it. I’m going to do my break now. Then we’ll bring Derek on and we’ll talk about avoiding a Q4 crisis. Folks, thank you for joining us for four years of Coffee with Digital Trailblazers. We have 193 episodes that we’ve done. We will be keep going at this. I’m thrilled to have you here. We are always looking for ways to grow our audience to bring more of you up on stage to be guest speakers, to get your ideas around topics and just to have you commenting here on the LinkedIn stream, sharing notes that I sometimes get over here into the dashboard. It’s great being here for you for this and I’m excited to be continue to host this for all of you. I’m starting to get ready our topics for next month and even into December.

Next week’s going to be a doozy, one you do not want to miss next week’s one. I have to figure out how I’m going to orchestrate this. But I think we have different perspectives around where AI agents are going, with some of us leaning toward more human augmentation and others leaning toward prepare for an automated agentic world. And I think we’re going to end up with somewhere in the middle where it depends on what agents we’re talking about. And we’re going to try to classify which agents are going agentic and which agents will end up human augmentation. So that will be on the 30th.

I believe this will be our topic on the 6th. This may change, but I’m hoping we’ll talk about planning 2027 where transformation leaders are placing their AI bets. We kind of do a forecast of what people should be prioritizing toward the end of the year. We’re going to do it a little bit earlier this year.

So that will be on November 6th, unless I have to put a different one in there. Look for my announcement later next week around November and December’s lineup. For those of you who might have missed this, I was on a huge webinar yesterday that freshworks put on on the next chapter for itsm went really, really well. Jake Cohen, who was here was listening to it.

If you missed it and you are in the service operations world or the Enterprise service management world or trying to figure out how AI is either creating more complexity in your operations or how to use AI so that your service desk can be more efficient and improve customer satisfaction. We covered all of that during our webinar yesterday. Please visit starcio.com/ai/itsm it will redirect you to that webinar and you can watch it on demand when you have some time. So thank you for that. Folks, we’re back. We’re gonna bring Derek up to talk about this. I actually want to hear from everybody about it.

A Q4 security incident can wipe out a year of wins. Tends to hit when teams are running skeleton crews.

What added precautions should risk leaders take to finish the year strong, especially around the AI tools and agents they rolled out in 2026?

Derek, I know you’ve, we’ve all been there. Like the security bomb hits you at the worst time, right?

And so I’m using Q4 as sort of an alias. It is the worst time for most companies to get a security incident. What are we doing differently this year to avoid that?

[00:31:04] Derrick Butts: Yeah, it’s the worst time for companies, but it’s the best time for adversaries. The reason being you’ve got Thanksgiving, Christmas and New Year’s, all these holidays pretty much went in a 30 day period. And they take advantage of the fact that these companies are running skeleton crews now that those companies that are actually looking to adopt artificial intelligence to help fill that void when people a little bit more lax, they’re not looking at stuff as much as they’d like to. The question comes about, you know, what is the agent actually doing? How is it really helping you? What do they have access to, what they can do once they have access to it and what can notifications or risk mitigation strategy connect to employees? And that’s something that companies are still trying to figure out. The chart that you showed earlier, you know, with the big push in ransomware is I think because of that the fact that the they’re trying to figure it out with the bots, but they don’t realize what the bots have access to until after the fact. And when that’s the case is they get breached and you’ve got more people clicking on stuff because of the holiday promotions and all the ads that are coming out. They want you to buy stuff. And with artificial intelligence, we’ve talked about the deepfakes, these things look very realistic. People see it, it looks familiar, they click on it. So these are the things that kind of help and help bring Businesses down to their knees because they’re not fully proactively paying attention to what are the things I need to mitigate up front, to kind of think about asking the questions up front before the holidays take place and figure out what the business can sustain and what it can’t do is going to be realistic. We need to figure out who’s going to be watching it, what validate the SOC coverage we’re going to have, what’s going to be the incident escalation if something is identified either by a person or a chat bot, who the vendors I can contact. And these are all the key things that need to fall into place as far as the puzzle to solve the demise. Because what we’re finding out is the holiday periods is supposed to be time of relaxation, not the time of hype. But for an adversary, it’s their, it’s their Christmas. They’re looking to prey on you because they realize you’re not going to be as diligent as you have in the past as far as doing that, so they’re going to take advantage of it. I think the other thing to look at is the frameworks that people have in place to kind of combat some of these things. We’ve talked about the CyberSecurity framework, the NIST 2.0, we’ve talked about MITRE, ATT and CK, MITRE Atlas, these all things that need to be escalated as far as looking significant AI threats as they become and they evolve. And companies evolve their processes to accompany these so they don’t get caught flat footed in the process.

[00:33:18] Isaac Sacolick: Derek, before I hand the mic over to Joe, you’re standing with your team, you got your soc, you got your analysts, you know there’s going to be a spike of activity.

You know, Jerome says, you know, you know, one piece of feedback is look for the vulnerabilities, the zero days that come out and address them quickly. It’s probably because somebody got infiltrated and you have, they’re, they’ve exposed something. It’s, it’s time for you to address them. What are you telling your team to look for in Q4? Just to get them, you know, on their toes, ready to find something before it becomes an impact?

[00:33:54] Derrick Butts: Well, I, the thing I think I’m looking for is one. Do you understand that we, does everybody understand what our current network looks like when it’s supposed to be running at optimal speed or when it’s considered good? And a lot of times when I talk to customers, they don’t know what a quality network looks or what their network should look like. So when these spikes, anomalies take place, and if there’s been a credential compromise, they’re not going to be able to recognize what’s abnormal versus normal. So I get my team online to understand that. That’s the first thing. The second thing I look at, if something happens and it does seem to abnormal, what is your process as far as who do you call next or who do you engage to make sure we can identify and validate it as a true threat? The zero days are something that’s hard to predict because it’s something new. But I go back to the first thing. If I understand the posture and the reactions and how my network works, I can now tag that as this is something that’s abnormal. I need to look at this further.

Quarantining, sandboxing, all these things that come in place, do they exist? Are they the things you want to have and have not put in place yet? It’s all part of that resilience, mindset and strategy changing, educating the business culture, my staff, the technologies and services and the tools, all they need to be in line and in sync and they need to be tested and vetted before the holidays take place.

[00:35:02] Isaac Sacolick: Thank you, Derek. You got three right here OR four Jerome Advising. Look for the announcements of where patches need to happen.

Derek is saying, you know, don’t ignore the anomalies. Oh, that’s just a spike. Don’t worry about it. It’ll go away.

Button down your escalation procedures. I think that’s really smart. What was steady state for escalation? May have some new rules during the holiday season when people are off and sandbox anything that has risk. Right. You know, the retailers have been doing that for a long time. If you have an E Commerce site, you’re pretty much in a blackout period during Q4. They’re not letting you release. Right. And it’s just a good discussion to have. If you haven’t had it with your business, your security, your technology groups, what aren’t we doing right during this season that may create more risk than reward? And maybe deploying, maybe deploying that agent right now is just not the best idea.

[00:35:59] Derrick Butts: But keep in mind, also, it’s not just the holidays. I do this in my companies throughout the year. So the holidays, just when it speaks, but you should be doing it more than just the holidays.

[00:36:08] Isaac Sacolick: Thank you, Derek. Joe, what do you have for us?

[00:36:12] Joe Puglisi: I. I think Derek has cited all the right things from a, you know, tactical perspective. I agree with his observation that this is not only a year end activity, these activities, but it should be throughout the year. The, the end of the year is heightened anxiety.

Sales wants to get, you know, they want to make their quota.

Salesmen want to get their commissions.

The warehouse wants to ship everything they can before that 1231 date.

There’s a lot of stress, not only in the IT department but throughout the organization. And that anxiety can create an era of, I don’t want to say carelessness, but really high anxiety inside the IT department. And so I pull out of my toolbox one of my tried and true rules. And that is rcat fact. I’ve said this a number of times, remain calm at all times. You have to build the discipline into your team. That panic is not an option. Let’s keep calm heads at all times. As Derek said, this is, you know, it’s not only fourth quarter, it should be throughout the year. But when those heightened anxieties are driving people up a wall, you know, that’s the time when you really need to take a deep breath, stay calm and deal with whatever inevitably happens. Something’s going to happen. We can deal with it.

Stay calm and be confident.

[00:37:39] Isaac Sacolick: I love that. You know, we’re, we’re. I’ve been laughing to myself the whole time here saying we need this agent that sits on the background for us, Joe, that will flag when we say a word too many times. You know, so I don’t know when I say transformation or Liz says governance is a four letter word or whatever it is, you know, Joanne mentions providence. And then we need ones that will pick up the things that mean so much. You know, the five whys from Joanne. And I haven’t heard you say RCAT all year.

And then I heard you say it to someone two weeks ago, maybe it was on stage at sim and now you’re bringing it up here. I think that’s a really important point.

That panic in the organization for them to close out their years on a bang.

Particularly in sales.

You know, if you have sales organization that creates a stress that trickles down and sometimes that’s needed when you need to make certain numbers but other times it has, most of the time it has collateral damage. And we talk about avoiding a crisis, it means paying attention to what’s really important. I think that’s what you’re getting at.

[00:38:50] Joe Puglisi: Yeah, yeah.

[00:38:51] Isaac Sacolick: Heather, what you got for us?

[00:38:53] Heather May: Well, I want to focus on. You were talking about the skeleton crew and then something Dana mentioned in the live stream that hackers don’t have a calendar. So it’s not a question of having a skeleton crew or the number of people, it’s having the right people so that you balance where the people that are missing with the right people that are strong enough and focused enough to be there when you need them.

[00:39:20] Isaac Sacolick: Have your team well prepared is what I’m hearing from that. Right, Heather?

[00:39:25] Heather May: Absolutely.

[00:39:27] Isaac Sacolick: Hey Joanne, what you got for us on avoiding a risk in Q4?

[00:39:34] Joanne Friedman: Well, one of the I want to focus for a moment on AI and agents.

If you don’t have this now and you’re trying to prepare it, first of all put your cutoff date before the end of November for new release. But you need to look at the back end plumbing.

Right? Disconnect if you can. Whether it’s through agencies and some infrastructures have some companies with heavy infrastructure have already done this. And particularly in manufacturing mission critical systems, which is everything in production. You want to look at the threat vector as the widest possible plane and disconnect the notion that every application and every agent is going to have some carry of permission. Disconnect that from the actual agency that you’re giving an agent to run. In other words, you have to do the rbac, the abac, all of those wonderful things, as I’m sure Derek would agree, and look at a way of disconnecting credential from the agent hitting the application.

There are plenty of tools out there that do this. It’s very much infrastructure as code in some cases. In other cases it’s policy as code. But the more of those things that you can put in place before we get to that critical time period, like you know, December 1st, before the world kind of turns off for the holidays, the better the results you’re going to get.

And part of the reason to do that is because there’s two levels of execution in AI and in agents in particular.

There’s runtime execution, which a lot of people focus on, but then there’s also execution that’s created within the agent. So it’s not just about go read this MD file or, or have a particular skill. It’s about looking very carefully at where credentials can and cannot be picked up as MCP servers are running, as APIs are running, etc. Because it turns out, if you’ve read a lot of the most recent research and archive is a really good place to find this, that this is where some of the most malevolent agents are running and where the most malicious code is coming in so you can protect yourself that way. The other point that I would like to make is to something Isaac, you said, which is stop shipping new agents till the beginning of the year. Like put a firm cut off. If you have things that are already in production, great. If you, if you’re in the process of looking to promote from Pilot through an SDLC into production, hold up, keep it in the sandbox. The month is not going to make a huge difference unless it’s really, really being pushed by the business.

[00:42:34] Isaac Sacolick: Yeah. This idea of delaying risky deployments but also having blackout periods and also thinking about when is a low risk time to deploy. We’re not riskless here. We’re just saying this is a good conversation to have with your business and come up with a calendar.

Joanne, before we go to our next question, Raymond kind of extends what Joe was saying. Yeah. We can have crisis hitting us from outside threats. Joe brought it inside. And say the internal inertia of everybody trying to hit their goals for the year creates a stress and potentially a crisis. And Raymond suggesting that the current uncertainties has resulted in a climate of survival, not one of thriving.

And that to me is potentially coming from the CEO down, from the board down.

What are you doing with that? First is, are you hearing those things? I think that’s his question. And what are you doing that when the leadership team is creating a Q4 crisis?

[00:43:42] Joanne Friedman: I’m trying to.

First of all, I’m not hearing it that way. I think that’s a lot. There’s a. A lot of doom and gloom associated with that. What I’m hearing is we need better solutions to help us mitigate the risk of these crises.

And you can’t control geopolitics, you can’t control supply chains. So what you can do is look for better ways of mitigating the risks and mitigating the costs. So the notion of a trusted path. Right. Like we built on our platform, you don’t promote things unless they’ve proven to be satisfactory to every member. But at the board level and the C suite level, I would say that if you show them the plan, how you’re building these things, where you’re taking, where you’re mitigating the risks, where you’re optimizing and what the value is going to turn out to be, it dispels a lot of that myth of things that we can control versus things we can’t control. We can’t control tariffs, we can’t control, control the straight of Hormu. We can’t do a lot of those things. What we can do is look at our individual businesses and say, where do we need to go from here because it’s finally starting to permeate the SE suite that you’re changing your whole business operation. You’re not just doing digital transformation and the two things are not unrelated, but certainly changing your operating paradigm is where they have to aim instead. And that sort of puts a little bit less of the panic attack mentality at bay.

[00:45:25] Joe Puglisi: I think it’s also a golden opportunity. Forgive me for interrupting here, but this is a golden opportunity to be the voice of reason.

Yes, you’re right, Joanne. You can’t control things that you can’t control. But you know what? You can control your reaction to it. You can control how you talk about these problems.

I’ve been in a number of situations in boardroom or senior management settings where people start standing up and shouting and, you know, it’s just not productive, it’s not helpful. You have to be that calm voice of reason to say, okay, the straight of four moves is closed or partially closed. Fuel prices are high. How can we deal with it? You know, you’re the transportation guru, Mr. Mr. X.

What can we do? We can put a fuel surcharge, surcharge on our customers.

We can buy electric vehicles. I mean, let’s look at the alternatives or how we deal with it. Let’s not just lose our heads.

[00:46:29] Isaac Sacolick: I’m going to answer Raymond’s question and then we’re going to go on to. Sorry, I’m going to go on to win as a team. Because I do want to cover that today. Sorry, Joanne.

Raymond, I am not hearing that. What I’m hearing is a rationalization that AI is doing things now that we didn’t contemplate at the beginning of this year.

It is not ignorable.

You cannot ignore it as a leadership team. So if there’s any panic in the leadership group, it’s, you know, does our strategy make sense?

Do we have a plan to execute on it? Do we know where our risks lie?

Those are the conversations I’m having is we can’t ignore this. We can’t expect our business to run in 2027 like it was in 2025.

And, you know, it’s both a value statement and a risk statement. We’ve seen, you know, the frontier models with their AIs doing some pretty bad things. And I think that, you know, that is a panic among the risk oriented leaders in our C suite. And that will be part of their conversation. And then there’s the others who see that disruption that might hit their business and saying, we better figure this out. Now let’s bring up our conversation back to our teams and ourselves.

I want to talk about, you know, the stressful year we’ve had. What specific steps should leaders take before the holidays to recognize their team and recognize re, recover their energy and set up a strong year from 2027. But before we do that, we’re going to bring Liz back and talk about the downer. Right. And how do we, Liz, I say this, you know, just honestly, you know, you manage Value Stream, you’ve managed portfolios, you’ve seen it all and there’s, there’s always a group that’s just perpetually unhappy. Right. And true.

So what are you either saying to them or to the people who are impacted by their message?

[00:48:37] Liz Martinez: Yeah. So first of all, it depends on your relationship to them.

[00:48:43] Joanne Friedman: Are you peers?

[00:48:44] Liz Martinez: I got to assume that your peers and also to, you know, in the setting.

My best advice is, number one, get with that person in advance, one on one to have a conversation about their concerns and what the messaging is going to be so that you can actually get them to vent in private

[00:49:10] John Patrick Luethe: and

[00:49:10] Liz Martinez: then actually ask them about, you know, what, you know, let’s brainstorm on possible solutions or what could define success so that not only are they heard, but that you can actually move them into a positive, proactive direction. And it kind of piggies back on what, what Joanne and Joe were just talking about. It’s like you have to, if you’re constantly lamenting the problems, then you’re wasting energy and not building solutions. Not that you shouldn’t ignore, you should ignore them by any stretch of the imagination, but acknowledging that, you know, you’re cold and the window is open, that’s fine, you’re cold. So let’s move on to what can we do? Can we close the window? Can we move to another room? Can we turn a heater on? Let’s develop options so that we can actually move past the complaining.

Complaining. Complaining in and of itself usually is a sign that there’s some energy there.

Capturing that energy and turning the energy is what you really want to do.

[00:50:18] Isaac Sacolick: Thank you, Liz. I didn’t really want to leave that stone unturned because it just, it’s happened to me, it’s happened to people on my team. It’s usually the same people causing it. And you know, in our attempt to give our digital trailblazers some advice, I thought that was important for them to hear.

[00:50:34] Liz Martinez: Yeah, one on one conversations are so important in those instances because typically the downer feels like they’re not being heard and so they’ll just get louder and louder depending on the person you can actually move into. Now let’s talk about the impact this is happening on the team. But maybe that’s not even a conversation you want to have.

[00:50:56] Isaac Sacolick: I think, look, I think you’re giving sound advice. I think the important thing here is bring it to a side conversation, Let them vent and make sure you’re hearing and that they hear that you. That they know that you’re hearing. And then you can have that conversation about what can you do.

[00:51:12] Liz Martinez: Yes. And what they can do, what ideas they have. Because if they generate it, that actually displaces the negativity.

[00:51:21] Isaac Sacolick: Love that. I’m going to change that. In the dashboard, what we they do, who raised their hand? I saw some hands up and then they disappeared. We’re talking about winning as a team now and taking care of yourself. Derek, where do you want to go with this?

[00:51:36] Derrick Butts: So I think when you look at it, I think it takes a look at looking at your entire people process, your whole business system as part of your resilience architecture. And I think there’s three areas we need to focus on. One is going to be recognize, recognize, recover, and then reset. And recognize is going to be the point. And looking at the things that worked well, looking to recognize the people that kept the system running, working through the challenges, decision making, all those different things. And look what we can do to make sure the resilience is in place to make that event never happen again. The recovery piece of it is looking at telling your team to disconnect, but also realizing that you have people and workflows and models in place for the recovery aspect that needs to take place and qualify, what coverage needs to be escalated during the holidays. And the reset portion is looking at. If we’re doing this resilience strategy for 2027, what worked? What do we continue doing? What do we stop doing? What do we automate? What are the things unnecessarily we don’t need to carry over? What are the dependencies we need to look at most of all? Know that everybody needs to go enjoy their leave, but make sure we have everything set so we can start 2027 strong.

[00:52:38] Isaac Sacolick: Thank you, Derek. Go ahead, Heather.

[00:52:42] Heather May: Sorry. Sorry. I couldn’t find the mute button. I really focused on, and I’m usually not selfish, but I focused on myself. But I think if, if you as a leader, one, as a leader, as a role model, there are things that you want to do for 2027 that maybe you want to do in a longer term horizon. So you have to be introspective. You have to be self reflected on what your goals are, have those personal goals related to your business goals. And at all times, be honest with yourself because you’re saying, well, I want to keep going, going, going in this direction. And you realize, no, you really don’t.

And sometimes you may need to take a pause and sometimes you got to take a stop.

[00:53:25] Isaac Sacolick: Thank you, Heather. Let’s. I’m just going to keep going around the room because we’re down to our last few minutes.

[00:53:30] Joanne Friedman: Joanne, I, I would say in very brief terms, ask the five wise and ask them of everybody, either in a group setting or one on one. And, and to Heather’s very valid point, ask yourself the same question.

Why are we doing this?

Why? You know, get to the root cause, whether it’s the person who’s filibustering against and always causing difficulties and doesn’t feel like they’re being heard or the person who is, you know, the shining star on the team.

As a leader, you need to find root cause. What’s driving everybody? In many cases now, it’s fear.

Not only because of economic issues and job loss because of a particular technology, but just generally speaking, everything that’s going on in the world is causing everybody to be on edge.

So ask your five wives and ask them with chocolate.

[00:54:31] Isaac Sacolick: There’s another one. We’re gonna have to remember this. I’m laughing because, you know, Heather had a great idea that December 18th is going to be our 200th episode. And we should talk about the 2000 areas of advice that we’ve all said and reset over these 200 episodes. I said we probably left at least five really good pieces of advice at every single one of these episodes. And chocolate’s got to be one of them. And the five whys. And I actually love this, you know, recognize recovery reset from Derek today. And obviously we’ve talked about celebrating successes multiple times, but folks, keep that December 18th locked on your calendar. I don’t know how we’re going to celebrate it, but that will be our 200th episode. Whose hand is up next? I think it’s Joe.

Or is it Derek?

We got Derek already, so I think it’s Joe. Go ahead, Joe.

[00:55:26] Joe Puglisi: Sure. I have five. Maybe they won’t make those, you know, the 2000 list. But five quick things when you’re winning as a team. First of all, recognition has to be specific or it’s noise. So it’s got to be the person and why they’re, you know, why it was special. What made it possible.

Great, great job. Team is too broad. We got, we got, we got to pick a person and get specific about it. That’s one. The second is private gratitude actually lands harder than public praise. It’s nice to say something nice about somebody that did something, but it’s even nicer when you send them a personal note, you know, an email just to them or a phone call perhaps, or even a handshake in person.

Private gratitude definitely lands harder.

Third, do as I do, not as I say, if we talk about people needing to unwind, take a vacation, unplug, disconnect, whatever you want to use as a term there, you know, you need to do it too. And I think Heather just alluded to this. You need to go to the beach and unplug the phone for a week, show people that you really can do it. Not only does it help you and help them, but it also, and there’s a little bit of trust in your team, right? You trust them.

Last is for those folks that are the so called skeleton crew that holds it together in Q4 when everyone else is on the beach, maybe they get a little something extra. I don’t know whether there’s a, you know, an uptick in their bonus or it’s some form of special recognition. But you know, let’s not forget the guys who, who are there working in the late shifts and the end of the quarter and whatnot. Let’s recognize them. So just a couple of points to help keep winning as a team.

[00:57:14] Isaac Sacolick: I think that’s a really good closer there. Recognize the ops groups.

They’re only recognized when there’s a failure. Liz, I’m going to give you the last word today.

[00:57:24] Liz Martinez: Well, I was going to take it in a slightly different direction, which is winning as a team.

Actually, if you want to sort of metric that out, it’s actually what you’re doing for your customer and showing the value that you’ve brought to your customer over the year and sharing that as. Look what we’ve done.

Like we can say that we did this.

It might just, it might be revenue, I guess, but I mean, that seems a little bit meaningless if in fact you’re working for a company that’s actually delivering something of value to your customers.

Like if you’re at a bank, look at all the people that we actually got mortgages for and look at all the people who we were able to support in going to college. Look at all the people, whatever, whatever the metrics are.

But sharing that win for your entire team in terms of what we did together is inspirational into the next year.

[00:58:25] Isaac Sacolick: Thank you. Liz. I think you’re bringing up the idea of connecting with customers. I can’t believe we left that to the last word, but I think that’s actually really important.

Also your key, you know, solution providers, your suppliers. Also a good thing. And for me to just thank all the folks here who have been commenting. There’s a lot of really good comments today from Dana, from Jason, Wayne, Raymond, Rick, just some really good comments here. Carla earlier, thank you for being part of this knowledge sharing, collaboration and community The Coffee with Digital Trailblazers if you missed my webinar earlier this week on the next chapter for ITSM talked a lot about AI as a way to help our operating teams. Visit starcio.com/ai/itsm I have at least one person who heard me here last week say I’m running an executive roundtable next Tuesday in Houston. If you are in Houston and want to join that, do Message me on LinkedIn. Isaac Sokolik and I will talk to you about getting an invite to that particular event. We’re going to talk about next week, AI agent strategy, Human augmentation versus in the middle versus Agentic, and we’re going to try to set up a debate here. I don’t know how we’ll do it, but that will be our conversation next week. I’ll announce our definitive list of November December dates sometime this coming week. Right now we’re planning on talking about where transformation leaders are placing their AI bets and planning 2027 on November 6th, folks. Have a great weekend. Thank you for being here. We’ll see you here next week at the Coffee with Digital Trailblazers.