Rob and Sherry talk through some strategies for solving big, complex problems. Rob shares a situation in which he and his co-founder had to work together to solve a problem, which further sparks the idea of how to work well with others and the benefits.

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Episode Transcript

Sherry Walling: Lots of coming and going in our life these days. I just returned from a really quick impromptu trip to Los Angeles with our two kiddos. It was something I had never done before, which was to very short notice impulsively buy plane tickets, which I found, I will have to brag about, from Minneapolis to LA, round trip non-stop for 250 dollars, so I was like, Oh yes we must go. So the kiddos didn’t have school last Thursday and Friday, so we hopped on a plane Wednesday night and went to the beach, and went to Harry Potter World at Universal Studios. Saw some great friends, and just had a really nice little momma-son weekend together. We ate a lot of frozen yogurt and spent a lot of time at the beach.

Rob Walling: Yeah that looked awesome. I would have gone with you, but I had some stuff I had to take care of here. It was just hashtag-FOMO for me all weekend. Fear of missing out, for those of you who aren’t hip to the jive.

Sherry Walling: Yeah, I think the other thing that you’re not hip to the jive about is you haven’t read all the Harry Potters yet.

Rob Walling: Yeah, alright

Sherry Walling: You’re not really entitled to Harry Potter World at this point.

Rob Walling: They wouldn’t have let me in to the park.

Sherry Walling: Yeah, there’s a test.

Rob Walling: And then I’m leaving in two days from now to go on my retreat. And the last retreat I had was in January, I think, and I know we tend to like to do one in June or July and then one in January, but with the move and everything, the chaos that was going on, I didn’t do that. So I’m heading four hours north of Minneapolis to Lake Superior and I’m going to be doing some serious founder retreat thinking and strategizing and relaxing to be honest. I just kind of feel like I need a break, just having been going full speed since January, and haven’t taken much time off.

Sherry Walling: Yeah this is really the first time that you’ve had much of a breather since the conversation about the acquisition began.

Rob Walling: Yup.

Sherry Walling: And it’s been sort of full throttle for you since then.

Rob Walling: Yep, so this will be nice. It’ll be nice to get away, and I’m going to take up my trusty copy of the Zen Founder Guide to Founder Retreats. If you haven’t read that book, it’s a book that Sherry wrote, an e-book, about how to take founder retreats and how to structure them and what to do and what questions to ask yourself. So I’ll definitely be referring to that while I’m up there. I think it’s 24 dollars? And folks can find the link to that at zenfounder.com in the upper right sidebar.

Sherry Walling: Hey, thanks for the plug.

Sherry Walling: So, I borrowed your phone and went for a run around Lake Calhoun. And my phone was dead, so I used yours. And while I was running you kept getting a ton of slack notifications from Derrick. And they were very positive, excited slack notifications. I didn’t really read them, but every time they came up they would interrupt my Spotify so I had to make them go away. So you want to let me know why you’re getting lots of gleeful messages from Derrick today?

Rob Walling: Yeah, so Friday, it’s Monday today, and Friday Derrick and I had this major breakthrough on a problem that we had been fighting on and off two, two and a half years. It’s a performance thing that happens when the database gets bigger and as more people use the app we work on. And we’ve always just taken a fairly linear approach to it, like let’s add another database index, let’s increase the size of the database server and give it more horsepower, let’s rewrite this piece of code. We’ve realized in the past few weeks that we are getting close to hitting the logical extent of that.

You can only optimize something so far, and so you have to take a different approach. And we’ve just been looking for a different approach, and the only different approach, the one that most people use, is just this really painful, complicated, time-intensive thing that you do and then you live with it forever after that. Once you make that choice, you can’t go back, it’s a restructuring of your database in essence. And it’s painful to do the first time, and then it makes everything more complicated. So we have just been … I have been agonizing over that choice, like really not wanting to do it.

And Friday afternoon we basically said, look we need to pull the trigger on this. Cause it’s gonna be months from now we’re gonna really start seeing a backup in performance issues and we need to get ahead of it … and we kind of said, if we don’t think of something better by Monday, we’re gonna start doing that thing that we don’t want to do, that restructuring. And then we just sat there for, 90 minutes or two hours, and we kept hammering on this problem.

And again we have thought about this over and over, where we’ve researched it, we’ve done this stuff … but for some reason in that 2 hour span we basically solved it. Like, we fixed it. And this is like a 10X or 100X solution. Like it’s gonna be 10 times or 100 times faster. It’s crazy how much this will scale. This could literally scale us out for 5 years or 10 years, some enormous amount of time. And that’s what we’ve been going back and forth about, texting over the weekend. We like talked about it on Saturday … That’s what the slacks were coming through, because now he’s working full force on this.

Sherry Walling: So you guys had this massive problem and thought that you were going to have to do this very complicated, very time intensive solution. But, you sat with it for a couple hours, and it sounds like you batted it back and forth and really thought through all of these different options and scenarios and like found this really novel, unexpected way to solve this problem, or way to strategize what to do. And now you’re both doing the little happy dance in your respective offices today.

Rob Walling: Oh my gosh. You should see all these texts we’ve sent back and forth with the emojis and the … and then we keep sending more and more ideas of how even this approach can be used in other areas of the app. Like I feel like we tapped something that is really big. It’s a big deal. That’s all I can keep saying, like this is a once-a-year, maybe twice-a-year kind of breakthrough that you have, where it just changes the game.

Sherry Walling: That’s pretty awesome. Congratulations, by the way. To both you and Derrick.

Rob Walling: Thank you. It reminds me again of why I like working on products and working on technical stuff because when you do solve a problem like this and it’s an elegant solution and it works, it just feels great. You know, it feels fantastic. But it was so painful to get here. Like I wish … It could have been interesting if we had thought of it 18 months ago or something.

Sherry Walling: I think one of the take-home big ah-ha’s about this situation is that you really needed the two of you, your combined brainpower to be able to solve this problem. Like you’ve been thinking about it, he’s been thinking about it, obviously you’ve talked about it before. But it was the extended time of just the two of you in a room really using your brains together that seems like it was sort of the tipping point of helping this problem to get solved.

And it’s a really lovely argument for having a co-founder, or having someone who is as mentally invested in solving whatever problem you’re working on, as you are.

Rob Walling: It is. And I’m not sure what to say about that. I’ve been a single founder a bunch of times and I know there’s a lot of folks who listen to this who are single founders. And it’s not a bad thing. There are pros and cons. But in this case, for these really hard problems, I have found that having Derrick to collaborate with has made us like … We make way better decisions and we come up with way better solutions than I think either of us could come up with individually.

And the interesting thing is we operate a little differently. Like I threw out the ridiculous ideas, and I do the big what-ifs, and I’m just trying to think super creatively in a way that some things I say Derrick rolls his eyes and he’s like, come on we can’t do that. You know, we can’t just remove the entire page from the app, or we can’t load everything a-synchronously. That would never work. And he’s right, but I throw it out anyway and then we follow a path that eventually gets us to some, at least in this case, a crazy good solution. And so, I can’t imagine trying to get to the solution that we did on my own, and I can’t imagine Derrick doing that either.

I was throwing out the ideas and he would basically take them and apply them in an engineering mindset and he … It was totally a collaboration, I can talk about what parts each of us contributed, but it didn’t matter because it wouldn’t have happened without both of us there.

Sherry Walling: And it’s not unlike some of the ways that we’ve tackled problems in our family, where we have a big problem or a big concern and we sort of sit and bat it around until we come to some new understanding or new arrangement. And I think maybe the conversation to sort of flesh out today in the next few minutes is, how to solve problems well with other people. Whether it’s the technical problem, like you and Derrick experienced, or whether it’s deciding whether to move to Minnesota or not, or you know it’s a family problem or a family question that you’re trying to work through … It seems like there’s some common ingredients that make those conversations either go well, or not be as effective as they maybe could be.

Rob Walling: Yup, I agree. And we’ve listed out six here, kind of six tactics or six strategies for solving big complex problems. And the first one is to have a co-founder or a collaborator on that. And I think that you can solve big problems on your own, but I think it’s going to be so much easier and you get that better end result if you have that person that you’re collaborating with.

Sherry Walling: Yeah, I mean, it depends I think to some extent. Like, some people do do better solving problems by thinking about them on their own, or maybe some problems are better solved in that manner, but at some point you have to bring that potential solution back around for some sort of testing or some Q&A to make sure that the assumptions that you have used in your solution to the problem really hold up against the perspective of another person.

But I think one of the things that is really important in having these key conversations, or these problem solving conversations, is to really make sure that there is dedicated, set aside time, that’s not distracted, where you can really focus on this problem as long as you need to.

I remember us having conversations where we sort of set it on the calendar and said, okay this is the day that we’re really going to talk about whether or not we’re going to put moving on the table in the [inaudible 00:10:39], or whether or not we’re going to homeschool or send our kids to school this year. And those kinds of conversations require potentially extended amounts of time that get derailed by any kind of interruptions. So it’s like, phones off, door closed, kids are asleep or out of the house or busy or doing something. And it’s this set-aside time where that is what we’re doing, there’s no tangents or disruptions allowed.

Rob Walling: Yeah, and that’s important because you have to get into a flow, right? You need to get into the zone, to where the problem is just so, it’s in your head where you’re holding the whole thing in memory. And both of you need to do this, if you’re working with someone else on it, and so it might take some time. It’s not something you’ll be thinking about for 10 or 15 minutes and likely come up with a solution, and if you get interrupted you lose that, it goes away. And who knows, that focus time may be, maybe it’s an hour, and maybe it’s 2 or 3 hours, but having that time to really chew on it … And then there’s one other piece, it’s like being okay, if you really are trying to think about some stuff, being okay with some silence in the room.

And I realize that a lot of times, can you imagine like going into a meeting, calling a meeting to solve a problem and it’s 3 or 4 coworkers and you’re sitting around there, and as you guys are all thinking of solutions, there’s just silence for two minutes or three minutes? Like it would be super awkward. Unless everyone knows that that’s okay, and everyone’s like thinking about the problem equally as hard. And that’s what I’ve found about folks I’ve been able to collaborate with, like yourself, and Derrick, is that there’s a comfort level where, if we just sit there in silence, it’s not awkward because we’ve done it before and we know that that silence means that I’m thinking hard and so are you. And you can often tell by that person’s … you learn their thinking body language. You learn their thinking expressions, you learn that some folks like to walk around, and or lie down while they’re thinking … It’s just funny to kind of see that.

So I think having focus time and then also being comfortable enough that you can sit in silence and think through … Give yourself time to both talk through but also think through the ideas.

Sherry Walling: Which is also especially important for introverts. We talked a couple weeks ago about extroversion and introversion and I think silence and having the space within a conversation to let the internal juices sort of marinate is super important for those of us who are a little more oriented toward introversion.

So one of the other things that we jotted down earlier when we were reflecting on your breakthrough with Derrick, and in some of the problem-solving conversations that you and I have had, is this idea of persistence, of deciding not to get frustrated by all of the rabbit holes, and like just letting it be okay to keep hacking away at it. And knowing that it’s going to take a while. So I guess realizing that if you’re 45 minutes into a conversation and you still feel like you don’t have much traction or a well-formulated possible solution, letting that be fine. And letting it sort of be known, that big problems take a long time to solve. So really creating the space and that set aside time and the patience within yourself to be persistent and to just keep at it and keep at the conversation until such a time as you either need to take a break and return to it at a different time or until that really juicy solution presents itself.

Rob Walling: Yeah and I think the reason you need persistence is that A, it’s a hard problem so it’s probably not going to come easy, but B, I find that just the sheer number of ideas you can throw at a problem allows you to view that problem from different angles, and completely different approaches. And so, the problem we were trying to solve, first we looked at it from the user-interface … Can we limit something there. Second, we looked at it from the database, can we improve the database performance or de-structure, de-normalize? Can we look at the code and do it … But those were all coming through just by crazy ideas that we were throwing out about ways to change things. And we weren’t necessarily thinking logically about the brainstorming of the ideas, but we were then taking each idea and applying it like in a technical sense, like does this work. Cause it has to work eventually.

But there was a level of trust, and I think this is the next item on our list, there was trust in the room that I could throw out an idea that was completely preposterous and I knew that I would not be judged, Derrick was not going to judge me for ridiculous ideas. He might roll his eyes, but then I would laugh and then we’d say, oh we totally can’t do that. But then that would lead us down this path towards an extension of that idea, or a variation of it, and having that trust in the room and being able to just throw out whatever I thought could feasibly work … I would often preface it with, well I know we would never do this but hear me out, and then I would throw out the idea.

Sherry Walling: I think that’s really important to highlight because when we talk about solving problems, particularly in a work or entrepreneurial context, I think we’re thinking about the smart strategies, and there’s a lot of focus on the cognitive process and the intellect. And it’s easy to forget the emotional ingredients that go into making problem solving successful. And so this idea of trust and this focus on trust really allows space for creativity, and without trust in this conversation, I think people hold back, I think people aren’t brave enough to throw out that really outlandish, we would never do this, kind of idea, because they don’t feel safe or they realize that there’s this potential that they’re going to be seen as stupid or even mocked in someone’s head for the idea that they brought forth.

So the emotional quality of this kind of conversation is as important as the smart brains that are involved. Without trust and this solid sense of connection, it’s really hard to do this kind of problem solving work.

Rob Walling: I agree, because I think if you feel like you’re going to be judged, you will mentally shut ideas down before they come out of your mouth, and those ideas could turn into the ultimate solution, which is typically what winds up happening, right. A semi-outlandish thing gets refined and refined again until suddenly you stumble upon something that’s not so outlandish and that actually may be the right answer.

Sherry Walling: I think one of the things that was really helpful in this problem solving experience you had with Derrick was the lack of ego that both of you brought to the conversation. There was no shame in not knowing, in not being able to solve this problem. You were working on it together, but nobody was upset or flustered or all bent out of shape about this problem besting you to this point. And I think that lack of ego also facilitates trust. It says, hey I’m humble enough to realize I don’t know how to do this and I can’t do it by myself, so I need you, this other person, to work together with me so we can come to this place of greater understanding than we could do by ourselves.

Rob Walling: That’s a really good point. I think that if there’s one thing we did well in building the drip team, especially the folks who we were collaborating with often like in Fresno, is that since Derrick and I tend to want to find the best solution to stuff, and we don’t tend to tie our ego to being the one that came up with that solution, we hired a bunch of people who felt the same way. We probably did it pretty intentionally, we looked at a lot of personality and such, but we would be in a room, and there’d be four of us or five of us and it’d be kind of a hard problem and everyone would stand up and throw ideas, and we would take the best ideas.

It was never, who thought of that, your idea has more merit, often my ideas were originally the most preposterous ones and ended up being the ones we’d throw out, but others in the room would then build on those, and … I think having a lack of ego and not caring, like who cares who solved this problem as long as we solve it together. And that’s a big thing I’ve seen at previous jobs when I’m working on teams, is that often let’s say the manager’s idea will be given more credence or the manager has the ego, or someone on the team may have the ego, and they really want their solution, not because it’s the best one, but because it’s theirs. And they will sit and argue for that one. And I think that can be really catastrophic or toxic, however you want to say, towards this process of finding the best solution to a problem.

Sherry Walling: Well, it’s the opposite of collaboration. I mean, when you’re collaborating on a problem, the we solves it. The plural entity solves it. And when you try to parse out who did what and when and who gets what credit, it’s totally antithetical to what it means to be collaborative, sort of knit together your abilities and your intellect and your creativity to try to produce something different. So, if there’s any type of competition or elbowing each other to see who’s best or who contributed most to solving the problem, that totally goes against any of the value that you get from a real collaborative process.

Rob Walling: I think the next thing that we did pretty well was to take a step by step evaluation of each potential solution as we threw it out there. And so, you’re often throwing darts, and maybe you’re deciding whether to homeschool or not, maybe if you’re deciding where to live next, what city, and maybe you’re solving a technical problem or an inter-personal problem. But, throwing out ideas and being able to then look at them without judgment, and figuring out why they will or will not work, and then figuring out, well if it won’t work, what can we do to fix that about this idea … And really just run through, evaluation I think is the best phrase for that, that was a big part of what we were doing. We didn’t just throw out a bunch of ideas, and have them be up on a whiteboard or on a text file or something and never, not follow each of them to its logical extent … Because that was important.

It took us going down maybe 20 different ideas, and one of them made a turn at a certain point, when we said it won’t work because of this, and then I think Derrick said, if we did that it sounds very similar to this other solution that I’ve heard about, but that would never work in this instance, and he totally like, we locked eyes, and we were like oh that was it. And so, if we’d just thrown out the ideas and been like, no no no they seem like they’d work, that wouldn’t have been enough. We really dug into each one, and dug into why don’t they work, and talked them through, and then tried to counter why each of them didn’t work and really tried to make each of them work, continuing to throw out creative solutions as we went.

Sherry Walling: Yeah that’s the difference between what you did and like brainstorming as it’s popularly thought of, you didn’t just throw out a bunch of ideas, or maybe you did and then you wrote them down, but each one you came back to and weighed carefully with this step-by-step evaluation of why won’t this work, how could we tweak it to make it work, what components need to be in place for it to work. That seems like a really important thing. I think the last reflection on this experience that I jotted down as I heard you talk about it is this determination to see it through.

And I guess we already spoke about persistence and they’re certainly analogous, but I think just not giving up on a hard problem and … You sort of had one solution on the table, this rewriting solution that you knew was going to be tons of hours and development time, and you weren’t excited about it but you could have done it that way. But having the time and space and taking the time, even over the weekend to really tinker with the idea, refine the solution and really see it through, and it’s being built right now, as we speak.

Rob Walling: Yeah, yeah that was a big part of it. It was just the refusal, really not wanting to do the long hard months of making the app more complex, and kind of just the refusal to accept that as a reality, I think was a big part of it and even once we arrived at the solution that we are going to use, we were just a few minutes in and Derrick said, ah but you know this won’t work because of this certain type of rule people can create. And then it was like, that was just a … As far as I’m concerned, just a reason to figure out how to make that work. And so then, outlandishly, let’s just create another table then and put a bunch of stuff in there, and then run a [inaudible 00:22:09] and it was just like, no we’d never do that, but then again that was the solution to a small piece of why the broader solution wouldn’t work. And we just kept taking it from there, and by that point, it was like, man this thing really might have legs.

Sherry Walling: I think there’s this unique satisfaction in this kind of collaborative problem solving. It’s like a win for the team. It’s really satisfying for both of you, or for you and I when we’re chewing on a problem, to go through this process and begin a conversation at a point of not knowing, and ideally it doesn’t always work [inaudible 00:22:42] but like after a couple hours, end a conversation with a game plan. And again this importance of setting aside focus time, of allowing silence, of deciding to be persistent, of having a conversation with the framework of trust, and not having egos in the room. And then this sense of step by step evaluating each potential, without too much emotion, without too much entanglement, but really thinking it through logically. Those seem to be the strategies that have helped collaborative problem solving be successful up until this point.

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