Tent Talks Featuring Harry Max: The Power of Priorities: Transforming Teams and Organizations

[00:00:30] Chicago Camps: Your new book, Managing Priorities emphasizes the importance of intentional prioritization. Can you explain why prioritization is often a deceptively tricky topic for leaders?

[00:00:45] Harry Max: Certainly the fact of the matter is prioritization is something that we’re actually remarkably good at in simple static environments and the fact that we’re so good at it in simple static environments means that we don’t actually think about prioritization as being a challenge in more complex, dynamic, organizational, at scale environments.

The reason it’s deceptively tricky is because as you move into larger, more complex, more dynamic environments, we tend to rely on the things, especially under stress, that we’ve done in the past, that we think are going to help us in the present, but in fact nothing can be further from the truth.

We actually need to have a repeatable, consistent, methodology for prioritizing. We need to be aware of the approaches, the tools, the techniques, the visual frameworks, the sorting techniques, the marketplace simulations. It gives us more, a greater range of options for choosing how it is we’re going to prioritize whatever it is we’re going to prioritize.

The other piece of it is that individuals tend to conflate prioritization With personal productivity or time management. But in fact, nothing could be further from the truth, right? You can prioritize anything. You can prioritize risks. You can prioritize symptoms. You can prioritize investments. You can prioritize targets. You can prioritize all sorts of stuff.

But if you think about prioritization as a function of stuff, you’ve got to do or work or projects, you tend to ignore a lot of the things that need to be prioritized and don’t actually attend to them at all. So for me, it’s really about prioritizing prioritization and making it a first class citizen and thinking about it holistically so that you can get better results.

It’s a skill and it’s a lot like any skill, like playing a guitar or playing piano or skiing or anything that requires that you either learn something new or relearn something if you have bad habits.

In a sense, it’s easier to learn how to play the guitar right if you already know how to play the guitar wrong because you’re already familiar with the instrument. But if you’re going to learn how to play the guitar for the first time, it’s not as easy to learn it upfront, but you’re much more likely to develop a better set of skills right off the start, and then you can play your three chords really well.

[00:03:10] Chicago Camps: You’ve worked with a variety of companies from startups to global brands. What common prioritization challenges do you see across these different organizations and how do you address them?

[00:03:22] Harry Max: The fundamental challenge in organizational life is that, as individual contributors and frontline managers and even as folks in middle management, Throughout the organization, we don’t actually see what’s happening as prioritization is taking place. It’s a little bit like the water we’re swimming in, right?

There’s that David Foster Wallace joke about the two young fish that are swimming by and an older fish, passes them and said, Hey boy, how’s the water? And then, A few minutes later, the young fish turned to one another and say, what’s water. And in an organizational context prioritization is happening all the time.

And in fact, excellent organizations are typically prioritizing pretty well. And those organizations rely on teams that are, prioritizing reasonably well. And those teams are composed of individual contributors and frontline managers that are prioritizing pretty well. But if you don’t actually know what to look for, you can’t see it.

And unless you understand what the patterns are it’s hard to discern what prioritization looks like at the individual level, at the team level, but especially the organizational level, because it is just part of the air we’re breathing in the water we’re swimming in so that the better organizations tend to have a fairly explicit vision And fairly mature operating models, the definition of how work gets done.

For example, when I was at HP, they had this whole process that involved Hoshins, which are basically giant ginormous goals. I didn’t know what they were as an individual contributor there even though I was in a little strategy consulting group internal to the company, I couldn’t have told you That what we were doing was going through an organizational prioritization process, but that’s in fact what was happening.

By learning what prioritization looks like inside an organization, by understanding that, as a team, if you use a method like speed boat, which I talk about in the book, one of Luke Holman’s methods for looking at, what are the things that are constricting your team or slowing it down, or could be speeding it up. What are the risks you’re trying to avoid, Getting good at working with a team and then not stopping there, but taking care of your own business, right?

Really doing what’s necessary to identify what’s most important for you and the work that you’re doing and taking care of your life every day and linking all that together, the awareness of what’s going on in the organization, the alignment of working with the team and really focusing on what matters most in your own life .

Put that all together and things are going to start working a little bit better.

[00:05:50] Chicago Camps: In the book, you introduce the DEGAP strategy. Can you walk us through this process and share an example of how it has been successfully applied in a real world scenario?

[00:06:03] Harry Max: DEGAP, D E G A P, it’s an acronym . And the idea of the acronym is that in all situations where there’s a current state, as is in a desired state to be there’s some kind of gap.

There’s a gap between what you’ve gotten what you want. And so if you want to close that gap, you want to de-gap it. And the idea here is that prioritization is like any sufficiently complex process. I talk about this in the book, using the example of animation. When I joined DreamWorks Animation, where ultimately I got to participate in the making of Shrek 2, what I didn’t realize was that animation wasn’t a bunch of people sitting around, making characters move.

Animation is actually a whole series of complex steps. One of which is about making the characters move, and prioritization is the same, right? It’s not just the fact of prioritizing, which is really the P, the last part of DEGAP. There are actually four other really critical stages. In any prioritization effort.

The first one is D. Decide whether you’re going to prioritize. And by that, decide if you’re going to do it intentionally or decide if not right. There are lots of situations where, you’ve just got to act. You’ve got to rely on your training and you’ve got to rely on your knowledge.

You’ve got to rely on relationships. You’ve got to rely on The tools you have at hand because you’ve got to move really quickly. You don’t have time to sit around and plot things out. Decide is really the first step.

And if you decide to be intentional or methodical or conscientious about the process of prioritizing, you move into the second step, which is engaging in the process.

And that’s really fundamentally about identifying who your stakeholders are. And identifying potentially where the sources of information are going to be that you might want to engage with and it’s about getting traction. Once you’ve made a decision, you’ve got to start getting traction way to do that is figure out where you’re going to collect the items that you want to prioritize.

I call them items because they’re not priorities until they’re Prioritize their potential priorities. So where are you going to collect the items? Where are you going to? Where are you going to collect information about those items? Who’s involved? Who matters? And so on and so forth.

Once you figured that out, you dive into the process of gathering that information.

So now you actively engage the stakeholders in those information sources and you interrogate those information sources and figure out what are the items you’re actually collecting and What’s the metadata and what are the criteria that you need to consider? And what’s all the stuff, right?

And then you’ve got all this pile of stuff and, once you’ve got this pile of stuff, then you’ve got to clean up that pile of stuff. So you go from the gathering to the arranging, and this is now about sorting things out, de duplicating. Potential duplicates. It’s about clarifying things that might be, vague or ambiguous.

It’s about starting to consider, okay I now understand that what’s important is this and what’s critical is that like, How might I go about prioritizing this? What sorting technique might make sense or what visual framework might make sense or what marketplace simulation might make sense or some hybrid method that strings them all together.

And then once you’ve sorted that out, then you prioritize , right? Then you lean forward and you ski down the hill, right? But you’ve already put on your boots. You’ve already figured out that it’s not cross country. It’s downhill. You’ve got your goggles. You’ve learned how to ski. So you’re not going to go down that black diamond thing first.

You’re going to take a more sensible route given your particular skill set. And that’s what DEGAP is. And at this point, it’s a muscle, right? You build it. It’s a skillset and a practical experience of that was, and I talked about this pretty extensively in the book was I actually boomeranged back to a startup that was growing very rapidly.

And after I left DreamWorks, I went back to a company called all Clear ID, which Had grown to national prominence, very small company, but had grown to national prominence because they were the company that was servicing data breaches like Home Depot, Anthem, Blue Cross Blue Shield, Sony, you remember that with the North Koreans and so on and so forth.

We were the people behind that, and I had helped start that company back in 2005. And when I returned, they had a completely unscalable system that was starting to crack at the seams. And we were under enormous pressure because data breaches back in 2014 were happening like every couple of weeks. And I had to figure out how to communicate to the board what we needed to do to replatform the system.

And in replatforming the system this thing had to be up 24 by 7 by 365, no downtime. The SLAs on this with the Department of Homeland Security were steep. Let me just go there. And so slowing things down. I was like, okay, I clearly got to prioritize. I’ve got to go through a methodical process.

Who are the stakeholders? I figured all that out. What are the sources of information? I figured all that out. And I started working with the team and I wrote all these priorities on a big whiteboard. And I started using this prioritization pyramid that’s in the book and started sharing with people how I was thinking about all this and this rolling whiteboard.

I was going office to office, deduplicating things and adjusting stuff and clearing up the categories and so on and so forth and finally got to a place where I had a model that. Was robust enough that I could present it to the executive staff and the CEO were comfortable, presenting it to the board, although I didn’t roll the whiteboard into share with the board.

I actually did a presentation, but once they could see the logic of the process that I went through and they recognized that the trade offs that they were going to have to make. We’re going to involve millions and millions of dollars. It was a much more sensible conversation and they wrote a check for an awful lot of money for a 24 month replatforming effort that system did not go down because we prioritize very carefully.

What were the new features and capabilities? Where are we going to pay down technical debt? What was the new process automation we were going to put in place? Where was it that we were going to focus on defect removal and so on and so forth. And that was a pretty heavyweight application of that, that worked out remarkably well.

And the outcome of that was we re-platformed the system and the business actually sold that part of the business to Experian.

[00:12:41] Chicago Camps: How do you advise leaders to balance personal and team priorities, especially in high pressure environments where everything feels urgent?

[00:12:50] Harry Max: That is the tough question, right? And I think it starts with recognizing that to a large extent, our sense of urgency is built on a false sense of urgency, and that is to say that if you rather than looking at urgency, start to think about things in terms of cost of delay, which is a kind of concept that I pulled out of the scaled agile community, it starts to take the idea of urgency and turn it into something that you can either look at qualitatively or even better look at quantitatively so you can start to evaluate the economics of what it means to not feel pressured to invest in.

Jump on top of something at the expense of something that might be more important and the. The book tries to address this by saying, look, it’s really hard to do things at scale if you’re not doing them well at the team level. And it’s really hard to do them at the team level. If you’re not doing them well at the personal level.

So I’m about let’s start with self, right? Look at yourself and the practices you’re engaged in and start focusing on what matters most to you in your life. And for your direct stakeholders. And I make a clear distinction that not all the stakeholders are people that you know, they might be people inside your own head, right?

They might be parts of you, right? You might have like your inner CFO, I joke around. And so really, understanding number one, whether what the cost of delay Is going to be whether you can really tap the brakes on something and not say no to it, but potentially say not now to it.

And then number two recognize that if you really focus on your own stuff first, you’re much more likely to be in a stronger position to be able to help your team and your team is going to be in a stronger position to be able to help your organization. And at the individual level, what I do is say, look, focus on the stuff that you’re avoiding.

First then focus on the stuff that has the highest cost of delay. And then focus on the stuff that’s going to move your strategic game forward. If you do those three things on a regular basis, and you turn that into a practice and then sit down with your team and use, as I mentioned earlier, use something like speedboat, Luke Coleman’s visual framework for identifying what’s holding your team back, man, when you’ve got your own stuff going on and you’re doing well and you’re working with a team that’s figuring out how to remove the impediments and obstacles to success.

And you’re working with other teams that are doing that. And those teams are composed of individuals that are really working on their own stuff, man. It’s amazing what an organization can pull off.

[00:15:28] Chicago Camps: For those new to leadership or struggling with prioritization, what are the first steps they can take to start making better decisions and creating more effective plans?

[00:15:38] Harry Max: So the, the simple answer to that is to prioritize prioritization in your life. How do you do that is what the book is about. And understanding that there’s a case to be made.

That prioritizing prioritization is going to be the difference that’s going to make the difference in your personal and your professional life. Once you’ve accepted that as axiomatic, you can look at, the five chapters that talk about each of the process steps, just to orient yourself to what these steps are, and then really focus on the following chapter, which is really about prioritizing for yourself by yourself.

So that you can make a routine out of every day asking yourself, what am I avoiding? And then if it’s multiple things, which is the thing at the top of the list, and then addressing that in a small amount of time so that it releases all the pent up energy that comes with trying to stuff that thing down and hold it there all day long while you focus on everything else.

Perhaps the thing I forgot to mention is the setup for that is when you wake up in the morning, and I push hard to get people to do this first thing in the morning because, by the time the morning’s over, it’s just the day is unfolding and it’s out of control. Do this before you check an electronic device.

Do this before you check news. Do this before you look at your slack. Do this before anything else with the exception of coffee or a shower or, getting dressed or whatever. Because when you wake up in the morning, your mind is clear, tends to be clear. And if you’re honest with yourself, you don’t have to be honest with anybody else, but you really got to be honest with yourself about what you’re avoiding.

And if you’re honest with yourself about it, and you give yourself just a little bit of time to work through, okay, I’m avoiding this tough conversation, or I’m avoiding, putting on my calendar that I need to do this particular thing, or I’m avoiding whatever it happens to be. And then, Allocating just enough time to knock it off the list.

It creates this incredible virtuous cycle of energy. And that is the beginning. It’s almost all I do now is just run through that practice because the rest of it comes so naturally. So I would maybe it sounds like cheap and easy, but oh my God, it is such a life changer. And back to your comment about Christina (Wodtke), to some extent, she was a huge inspiration for this book on so many different levels.

They talk about inciting incidents in the movie industry, right? What’s the thing that caused the thing to happen and you take my conversation with Christina back, I don’t know what it was like 2014 or 2015 at south by southwest and she like grabbed my shirt she’s like, how do you do it?

You get so much done! Tell me your secret and we sat down and I outlined for her The process that I had developed over years and then she wrote it up You And it’s called the morning boot routine, right? She was the one that first documented this and put it out there on the internet. And I’ve gone and pressure tested that against all sorts of other people that have this mise en place oriented level of habit to, to tackle the things that are going to be most impactful in their lives.

But she was really the one that I think the wake up call for me that there was something here. And then I set it aside, really not paying much attention to it, but it always sat in the back of my head. And then it wasn’t until I was at USAA giving a talk on problem framing and diagnostic thinking.

And then I did the same at the Innovation Game Summit at Adobe. That all the hands went up when I touched on the topic of prioritization. And that was where the penny dropped. It was like, Ah, I’m a product guy. That’s a demand signal. There’s something that’s missing here for everybody.

How hard could it be to write a book? But most of the book is not stuff that I invented.

But most of the book is stuff I discovered and then just simplified and packaged up so people could read it.