Navigating Progress, Wins, and Support in Problem-Solving

Back in 2022, I wrote a post called 20 Things I've Learned as a Systems (Over) Thinker—”over” was in parentheses—and I've since received so much feedback about that post. I recently re-shared it on LinkedIn and it obviously strikes a chord. And so I thought that for this episode, I would just quickly go through that list, provide a little bit of extra color, and hopefully clarify some things.

I'll be back to interviewing guests in the next episode, but I'd just like to experiment with this format and be curious what you think.

Here is the list for reference:

* Take care of yourself. Your brain is working overtime—all the time. Practice “radical” recovery.

* You may spend a lot longer thinking about things than most people. Pace your delivery.

* If you go deep first, and then simplify…keep in mind that you don’t need to show all of your work.

* Your default description of (almost) any problem will be too threatening/overwhelming.

* Do your deepest thinking with co-conspirators (not the people you’re trying to influence).

* Informal influence is often not formally recognized. Prepare mentally for this.

* The people you’re trying to influence spend 98% of their day overwhelmed by business as usual.

* Remember to also do the job you were hired to do (if you don’t you’ll be easier to discount).

* Seek “quick wins”, but know that most meaningful things will take a while.

* Some things take ages to materialize. It is discontinuous, not continuous.

* Make sure to celebrate your wins. They will be few and far between, so savor the moment.

* The people who support you in private may not be able to support you in public. Accept that.

* Hack existing power structures—it’s much easier than trying to change them.

* Consider becoming a formal leader. It’s harder in many ways, but you’ll have more leverage. What’s stopping you?

* In lieu of being a formal leader, make sure to partner with people who actually “own” the area of change.

* Watch out for imposing your worldview on people. Have you asked about what people care about?.

* You’ll need a support network. And not just a venting network. Real support.

* “Know when to fold ‘em”. Listen to Kenny Rogers The Gambler. Leave on your own terms.

* Don’t confuse being able to sense/see system dynamics, with being about to “control” them. You can’t.

* Grapple with your demons, and make sure not to wrap up too much of your identity in change

TRANSCRIPT

[00:33] Take care of yourself. Your brain is working overtime all the time. Practice radical recovery.

I would basically find myself at the end of a multi day effort . I wasn't aware of just how tired I was and just how fried I was. How muddled my thoughts were. And I think part of the reason for that is if you enjoy going deep on things, and if you enjoy picking things apart, and if you enjoy analyzing things, you sometimes don't notice just how much effort that takes and how much bandwidth that takes.

And so it was important for me to try to set aside time to just completely disconnect, not jump into another thinking topic, not jump into something else that had high cognitive load, but try to strive for zero cognitive load. One of my favorite things is just watching cartoons with my son. Because I completely disconnect.

[01:29] You may spend a lot longer thinking about things and most people. Pace your delivery.

So if you've spent many hours going deep on something, you can't walk into a meeting and expect someone in three minutes to follow your thought process. It's just not going to work. You're going to have to pace your delivery to bring someone along on that journey.

And if you're good at analyzing things. If you're good at this type of systems thinking or overthinking, you can go so far in a couple hours. You can focus and go so deep. And there's no way you're going to be able to deliver all that information to someone. You have to get really really, really high level and rewind. And be super deliberate about how you deliver that information.

[02:17] If you go deep first and then simplify, keep in mind that you don't need to show all of your work.

So what I used to notice is that I would keep all of my work and the three bullets. And I would start with the three bullets and say, well, this is where I arrived at. And I felt like it was important because for some reason it's important to me to show how I got there.

So instead of just saying, here's the solution, do this. I would say let's try to unpack all the layers of this particular problem and how I arrived at this particular solution.

It turns out that that can greatly diminish the impact of the destination that you arrived at. And honestly it can open you up to all sorts of debate. It can open you up to all sorts of questions. And somehow it makes you seem less confident about what you're doing.

Now, not that I agree with any of that and I wish it could be different, but realistically you don't need to drag people through the whole mess.

[03:17] Your default description of almost any problem will be too threatening or overwhelming.

This is something I've had to come to grips with. The default detail that I want to go into on something is just going to seem threatening.

And the more I try to sugarcoat it the more weird it sounds also. So this is a tough one to come to grips with, but the important point here is understanding that the depth that you go into on something and the thoughtfulness you try to put into something and the different perspectives you try to discuss can be very threatening.

In fact, I used to think that describing something as a systemic issue was in fact less threatening. Because in some ways, by describing it that way you understood that well, there's a lot of contributing factors. There's not one person to blame here. There's a lot going on. And we're going to be able to figure this out. Or so I thought.

Realistically, when people hear systemic issue, when you don't point to one specific person or one specific situation and say, that's, what's messed up, it's actually highly threatening. So keep that in mind.

[04:24] Do your deepest thinking with co-conspirators not the people you're trying to influence.

In an ideal world, at least for me, everything would be co-designed. Everything would be a result of deeply exploring things with everyone involved. And you would arrive at the solutions that everyone believed in.

That's not the case, in many situations.

You might have other people that you're close with who are willing to go on this deeper journey to understand what the problem is. And I call those co-conspirators in this case. These are fellow system overthinkers who don't mind the ambiguity, who don't mind exploring different paths and then rewinding. Who don't mind dredging up these particular issues and looking at them from different angles.

Realistically, if you're trying to influence someone, it might be a good idea to bring them on that journey. But it might actually completely defeat your cause to bring them on that journey. So in that particular situation, if the person you're trying to influence isn't necessarily on that wavelength, and doesn't want to take that journey with you, you don't bring them along that particular journey. And you might be more influential in the long run.

[05:36] Informal influence is often not formally recognized. Prepare mentally for this.

If you're expecting the same kind of recognition that goes to people with formal influence and formal authority, you'll probably go off track. In fact, I think if you're seeking that, if you're seeking that recognition, if you're seeking to be in the limelight, if you're seeking that kind of gratitude publicly, you will be sorely disappointed. And it will probably send you off track.

So you have to prepare mentally for the fact that many of the things you do will influence informally in ways that people might not be able to immediately recognize. You might have a small number of people come up to you and say, you know, I really liked what you did there. Thank you so much. I really appreciate it. But it's not going to be this groundswell thing. You're not going to win the president's club trip to Hawaii or something with your sales team. And as long as you prepare mentally for that, I think you can be in good shape.

[06:39] The people you're trying to influence spend 98% of their day overwhelmed by businesses usual.

If you're trying to influence senior leaders you need to understand that they are really busy. This seems to be such common sense. But if you imagine that they're going to have any amount of time to go deep or as deep as you've been going on something, and appreciate all the nuances-- if you're expecting that-- you're going to be disappointed.

So you need to imagine that you are delivering the message to people who are overwhelmed. Who are under incredibly high cognitive load. Who are not necessarily in the right frame of mind to explore some kind of systemic issue.

You have to be prepared for that. Remember, you've set aside a couple hours to go deep on something. You've had all this time to do this focused work on something. This person is getting bombarded by every single person in the company. Back and forth. Everyone has a problem. Everyone is trying to sell them something. Everyone is trying to influence them. Everyone's telling them their version of what's wrong. That's the person you're trying to influence. And so you need to modify how you talk to them accordingly.

[07:53] Remember to also do the job you're hired to do. And if you don't, you'll be easier to discount.

So you might've been hired in the company to do job a. But upon arriving and because of the way you think you discover all these other problems that are probably deeper problems impacting the ability to do a. And so you go and you try to solve those particular problems.

Just be aware that if you don't do the job you are hired to do or don't work to clarify the job you were hired to do-- because maybe they didn't know the job you were supposed to do so you have to craft that role when you walk in-- when things get difficult, or if someone's looking for someone to blame, or if someone's looking for someone to say, well, I don't know what they're doing, you're going to be pretty vulnerable in that regard.

So keep that in mind.

[08:41] Seek quick wins, but know that most meaningful things will take a while.

Things don't change in companies in a matter of days or weeks, it can take years for things to change. So it's important to be realistic about the change efforts or the things you're trying to influence in your company. It's unlikely that things are going to just happen right away. So obviously enjoy the quick wins. But be prepared to play the long game with most of the things that you're working on.

[09:12] Some things take ages to materialize. It's discontinuous, not continuous.

I guess this is extending number nine to make a point that progress is also not continuous. So someone might say, well, we'll take three years, but progress towards that will be pretty incremental and every month things will get better, but even that doesn't work like that. You could be going for a year and not really see noticeable results. Maybe there's leading indicators that things are working. Maybe there's small signals that things will improve. But progress isn't always continuous. You'll often have to put in a lot of time, and then suddenly you'll see the fruits of your labor appear and then things will level off again. And then suddenly the fruits of your labor will appear again and then level off again and then probably drop again and then go up again. So just be prepared for that.

[10:02] Make sure to celebrate your wins. They will be few and far between. So savor the moment.

When something does go right, make sure to enjoy it. A lot of passionate problem solvers and systems thinkers and other folks are, are so zeroed in on the big picture and how everything is connected, that they don't give themselves the opportunity to savor the immediate wins that they have. They don't tell people about it. They don't think, Hey, maybe I'm going to take a day or two off.

They keep pressing on and on because they see the bigger nut they want to crack. And so don't forget to celebrate your wins.

[10:43] The people who support you in private may not be able to support you in public. Accept that.

So if you are an informal influencer, if you're someone who's trying to pick apart a wicked problem for people, you probably will have people thanking you for your effort.

And they might support you in private. But remember that supporting you in public is a much different proposition. It's very, very different.

And so that person who's supporting you and helping you along the way, or is a co-conspirator with things, might not be in a position to, in a public setting say, and I'm working with X to be able to influence that. They might not have that privilege and it might not be good for them to do that. So don't expect that in return.

[11:31] Hack existing power structures. It's much easier than trying to change them.

If change happens in a certain way in your company, as a result of certain power dynamics and power structures, it is so much easier to latch into those dynamics than it is to try to change that.

And so a lot of kind of deep thinkers or change agents try to upend the whole shebang. And it's very, very difficult to do that. And so, very importantly, if you see something you can hack, if you see something, you can latch your efforts on to consider that.

[12:09] Consider becoming a formal leader. It's harder in many ways, but you'll have more leverage. What's stopping you?

I've noticed this in myself. And I've noticed this in other folks who have some of these characteristics. But, it's a fear of formal leadership.

And in some cases, I think this is because they see potential abuses of power. Abuses of formal leadership. And they don't want to be that person, or they are afraid that they might commit those same things and be seen as a little bit of a sham right? Seen as a bundle of contradictions. Oh, when I wasn't a leader, I said this was broken. Then I became a leader and I became just the same people that I was railing against when I did that.

So they talk themselves out of formal leadership positions. And I guess it's important to know that, Hey, if it's not you, then it's going to be someone else. And I think that's an important consideration for many people.

[13:04] In lieu of being a formal leader, make sure to partner with people who actually own the area of change.

This is a little bit like hacking existing power structures, but basically there's people whose job title is to fix something. There's people whose job title is to improve something. And if you work separately from them, You will be seen as working in contradiction to them.

There's a reason why they have that job title and have those responsibilities. And you just don't want to end up in a battle with someone with that formal responsibility. It's much better to partner with them.

And in many cases it's much better to let them get the credit for it because they need the credit because it's part of their job description.

[13:44] Watch out for imposing your worldview on people. Have you asked about what people care about?

I've fallen into this trap so many times. I'm a raging collectivist. If it was me, we'd have, you know, 150 person retros and people self assigning to all these improvement areas and managers would be primarily coaches and wouldn't really be micromanaging these teams and the improvement stuff. It would be crazy town. Because that's me.

It's easy for me to impose that world view on other people. It's important to ask, what do they care about? How do they think the world works? How do they think change happens?

Some people imagine change is primarily a function of people's merit, about individual effort, about individual responsibility and accountability. And if you run in there like a raging collectivist, and expect them to just do what you want to do in the way you want to do it. It's not going to work.

[14:42] You'll need a support network and not just a venting network, real support.

Venting networks are groups of people who get together and just vent about the current situation. They whinge. They talk about how messed up it is, how circular it is. It's almost a spectator sport at that moment.

And at every company they have these venting networks.

However, that's not going to be enough. You need a support network. You need people who are going to listen to you, and are going to try to nudge you towards being proactive. And maybe let you do the same for them in return. Right? You're going to need a support network, not a venting network.

[15:23] Know when to fold them, listen to Kenny Rogers, The Gambler, leave on your own terms.

Pretty self-explanatory, but for your own health and wellbeing, it's often good to know when to move on. You've tried your hardest. Hopefully you did your best. You learn from, maybe, the mistakes you've made, but it's time to move on.

[15:41] Don't confuse being able to sense/ see system dynamics with being able to control them. You can't.

For people who are able to go really deep on things and who are empaths or highly sensitive people or any combination of these things, you are sensing things and seeing things that many other people don't see. However, it's super dangerous if you think, just because you can map it out, just because you can sense it just because you can describe, it means you can control those forces. You can't. Now you might be good at figuring out good places to start experimenting. You might be good at figuring out higher leverage places and lower leverage places, but just because you can see and understand something doesn't mean that you're able to just jump in and fix it.

[16:28] Grapple with your demons and make sure not to wrap up too much of your identity in change.

Huge one for me, I've fallen into this trap a bunch of times. When you self-identify with some outcome, some change outcome, and it's reflecting some deeper part of your past or how you grew up, or how you interact with people. And once those things connect together, it's very, very difficult to find a positive outcome. You'll find that it's never good enough. You'll find that you're never able to work out whatever you were trying to work out through your work and through some particular piece of change. So when you are trying to work out some of your demons through the change efforts or thinking efforts you have in a work environment, just be very careful.

I hope this format was interesting and that you found it helpful. I'll be back to interviewing guests in the next episode. Have a great day, have a great weekend. Take care of yourself.