95. Puzzle Setting, Not Goal Setting
In this episode we discuss: Puzzle setting, not goal setting. We are joined by Radhika Dutt, Author, Speaker, Consultant.
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We chat about the following with Radhika Dutt:
- What if traditional goal setting is actually limiting innovation rather than driving it?
- How might teams think differently if they framed challenges as “puzzles” instead of targets to hit?
- Are OKRs pushing organisations toward short-term optimisation instead of real problem-solving?
- How can leaders create space for curiosity and exploration in environments obsessed with metrics?
- What would change inside your company if teams focused on solving the right problem rather than just hitting the next KPI?
References
- https://www.linkedin.com/in/radhika-dutt/
- https://www.radicalproduct.com/
- https://www.radicalproduct.com/toolkit/#OHLToolkit
Biography
Radhika Dutt is the author of Radical Product Thinking: The New Mindset for Innovating Smarter which has been translated into Chinese and Japanese. The methodology she introduced in her first book is now used in over 40 countries. She is an entrepreneur, speaker, and product leader who has participated in five acquisitions, two of which were companies that she founded. She is currently Advisor on Product Thinking to the Monetary Authority of Singapore (Singapore’s central bank and financial regulator), and does consulting and training for organizations ranging from high-tech startups to multinationals on building radical products that create a fundamental change. Radhika has built products in a wide range of industries including broadcast, media and entertainment, telecom, advertising technology, government, consumer apps, robotics, and even wine. She graduated from MIT with an SB and M.Eng in Electrical Engineering, and speaks nine languages.
Radhika is now working on her second book – it’s about why goals and targets backfire and what actually works.
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Summary
14:25 — Introducing the concept of “puzzle setting”
24:06 — What puzzle setting actually means
26:46 — Why puzzles embrace uncertainty
27:49 — The Rubik’s Cube analogy
33:22 — The “Three O’s” of puzzle setting
35:17 — Turning growth goals into puzzles
38:08 — Breaking big puzzles into smaller ones
42:46 — The shift from proving to learning
47:25 — Building critical thinking into teams
54:44 — Real business impact of puzzle thinking
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Transcript
Hello and welcome to another episode
Speaker:of the Operations Room, a podcast
Speaker:for COOs.
Speaker:I am Brandon Mencinga, joined by
Speaker:Bethany Ayers. How are things going,
Speaker:Bethany?
Speaker:It's just relentless, I think.
Speaker:I don't know if that's how things
Speaker:are going, but that's things are
Speaker:feeling.
Speaker:I know, I'm hearing you on this loud
Speaker:and clear, the relentlessness of
Speaker:the job.
Speaker:Relentlessness of VC-backed
Speaker:businesses, which we signed up for
Speaker:it. We love it.
Speaker:We enjoy it a good 60%
Speaker:of the time, maybe 70% of time.
Speaker:Yes, yes.
Speaker:This week has been a terrible week
Speaker:for me in this sense, which is
Speaker:people issues related to people
Speaker:not understanding the fact
Speaker:that these are scale ups.
Speaker:It's venture backed.
Speaker:We need to move at pace and
Speaker:their personal situations or
Speaker:their workloads or whatever.
Speaker:I respect the fact the people need
Speaker:to like have their space, craft
Speaker:their worlds and so on.
Speaker:But there's also very much like a
Speaker:pacing element to this company and
Speaker:to venture-backed.
Speaker:Your point that is relentless and
Speaker:needs to happen so being in
Speaker:service about which we all are
Speaker:because we all signed on to this is
Speaker:the name of the game if you're not
Speaker:up to it you don't want to do it yet
Speaker:personal considerations don't allow
Speaker:you to do what you should not be
Speaker:signing up for this venture back
Speaker:journey i would say.
Speaker:100%.
Speaker:And also, on
Speaker:top of just the general
Speaker:rollercoaster that is venture-backed
Speaker:businesses, we have AI
Speaker:and the shifting sands
Speaker:below us and the market changing
Speaker:every day,
Speaker:and anthropic building our products
Speaker:every day or somebody else's
Speaker:product.
Speaker:I know, I know.
Speaker:The general gist of it is, yeah,
Speaker:we're behind, everyone's behind, I'm
Speaker:behind, you're behind.
Speaker:Who's not behind?
Speaker:I'm like, I got it.
Speaker:There's like another kind of CEO
Speaker:problem. We have like a thousand
Speaker:things to do. We need to move at
Speaker:pace.
Speaker:Sands are shifting.
Speaker:We need get behind that to make sure
Speaker:that we're transforming the
Speaker:business.
Speaker:And trying to do all of it at once
Speaker:is like, there's only one brand
Speaker:and there's not three brand ends or
Speaker:three versions of ourselves, there
Speaker:is only so much you can accomplish.
Speaker:But you can see I'm kind of riled up
Speaker:this morning as we speak.
Speaker:Yeah, and it's also something I've
Speaker:been thinking about and have talked
Speaker:to my team about, but I don't think
Speaker:it's just unique to
Speaker:us is
Speaker:not only is it like AI adoption
Speaker:internally, but it's this ability
Speaker:to shift to markets because
Speaker:the market's moving so quickly.
Speaker:It's kind of both moving quickly and
Speaker:not moving at all.
Speaker:Like there's definitely a
Speaker:bifurcation of the
Speaker:adopters and the movers.
Speaker:And I feel like after open claw.
Speaker:There are a lot more people who are
Speaker:throwing themselves into AI than
Speaker:there were a month ago.
Speaker:But then you still have companies
Speaker:that are moving at a snail's pace
Speaker:who can't
Speaker:figure it out.
Speaker:And kind of like straddling these
Speaker:two worlds.
Speaker:And it means like, there's been
Speaker:a lot of talk around the
Speaker:change of org structure and what
Speaker:roles are staying and what rules are
Speaker:going in this new world.
Speaker:But I don't think we've talked as
Speaker:much around Cadence.
Speaker:Operating models and
Speaker:speed.
Speaker:Some of it I thought was specific to
Speaker:my experience at Matomic in that
Speaker:we're 20 people, the
Speaker:goal is not to be 100 people, the
Speaker:goal was to be maximum 50
Speaker:people.
Speaker:But we've all come from bigger
Speaker:companies and we have a
Speaker:tendency to over
Speaker:process stuff and
Speaker:put in things that are unnecessary
Speaker:for the of people that we are.
Speaker:But I'm wondering if it's that or
Speaker:actually
Speaker:old way of building is
Speaker:let's put in the scaffolding, let's
Speaker:make things quite rigid so that they
Speaker:will hold the new
Speaker:bigger company.
Speaker:But right now, if you make things so
Speaker:rigid with the shifting sands,
Speaker:you're just going to fall and crack
Speaker:and break into the sand.
Speaker:And so what you actually need to do
Speaker:is figure out how to build much
Speaker:more flexible
Speaker:Processes systems ways
Speaker:of accessing information ways of
Speaker:communicating so that.
Speaker:You can bend and
Speaker:shift as the sands move rather
Speaker:than break.
Speaker:I don't have the answer to it, but
Speaker:it's something I'm starting to
Speaker:formulate is like, how do we
Speaker:make our businesses more flexible?
Speaker:And also like right now is probably
Speaker:not the time to build the processes
Speaker:that we're familiar with.
Speaker:Like it's really the time to think
Speaker:about what's the output
Speaker:we're looking for and have
Speaker:less of a formulation
Speaker:on time.
Speaker:I'm trying to articulate this versus
Speaker:like the ability to
Speaker:get what you need when you need it,
Speaker:share what you to share when you to
Speaker:it, rather than
Speaker:in a cadence that we've
Speaker:been used to where things were
Speaker:moving.
Speaker:Like, venture's always been fast,
Speaker:and we've always maybe moved on a
Speaker:weekly or monthly cycle, but I feel
Speaker:like today we almost need to work
Speaker:on a daily cycle.
Speaker:And so how do you build systems
Speaker:that mean that you can communicate,
Speaker:share ideas, move direction,
Speaker:change your home page.
Speaker:Create a thousand different landing
Speaker:pages today
Speaker:and not in two and a half weeks.
Speaker:From an individual, from team point
Speaker:of view, there should be like a
Speaker:much stronger capacity to move
Speaker:way faster, doing a lot more things.
Speaker:So if you think about classic
Speaker:customer discovery that a product
Speaker:manager would do or a UX researcher,
Speaker:you know, that process used to be
Speaker:quite tedious and quite slow in
Speaker:terms of the processes that they
Speaker:go through. I think today for
Speaker:customer discovery, you can do that
Speaker:way faster.
Speaker:And it's not just the product
Speaker:manager anymore, but it's the actual
Speaker:engineers themselves and the
Speaker:designers, everyone's involved in
Speaker:customer discovery in some form.
Speaker:And the speed by which you can,
Speaker:you know, the bottleneck is more of
Speaker:just like the customer interactions
Speaker:themselves than anything else
Speaker:required down flow from there
Speaker:because we can kind of AI agent
Speaker:orchestrate almost everything to
Speaker:actually get the realizations,
Speaker:the insights, the changes to the
Speaker:product roadmap, and then the actual
Speaker:production of those features or
Speaker:experiences, you now, from a
Speaker:kind of the coding perspective as
Speaker:well, I suppose.
Speaker:Yeah. And so maybe it's
Speaker:not around flexibility, it's around
Speaker:collapsing time.
Speaker:But I think if you collapse time,
Speaker:that also gives you flexibility.
Speaker:And one of the things that is
Speaker:definitely a mind shift change
Speaker:that I see some people
Speaker:needing to make is,
Speaker:this is a hypothetical, this isn't
Speaker:actually something that happened,
Speaker:but it's just come to my mind, is
Speaker:by example, if we need a
Speaker:thousand landing pages.
Speaker:I mean, we don't really need a
Speaker:thousand pages, but like...
Speaker:I feel like sometimes what we do is
Speaker:figure out how to build a thousand
Speaker:landing pages.
Speaker:But what we don't do is think,
Speaker:I'm going to need to be able to,
Speaker:like the operator brain, I'm
Speaker:not gonna only have to build 1000
Speaker:pages once, I'm gonna have to do it
Speaker:all the time.
Speaker:And I'm also going to have to like
Speaker:change the website overnight or
Speaker:do that. And so how do I actually
Speaker:build the whole system that then
Speaker:enables rapid change?
Speaker:In not just building a thousand
Speaker:landing pages, but like the entire
Speaker:marketing flow, for example.
Speaker:And I think it's as operators
Speaker:and COOs,
Speaker:it's the way our brains naturally
Speaker:work. And so I think maybe we need
Speaker:to start training people
Speaker:to see how our brains work, or
Speaker:how do we create
Speaker:clawed skills that are
Speaker:that, and everybody uses that
Speaker:clawed skill. That would be the
Speaker:better solution, brain working in a
Speaker:second. I used to talk about how we
Speaker:need to get leadership skills into
Speaker:the team. And I think now how do we
Speaker:get system thinking and operator
Speaker:thinking into the team?
Speaker:Yeah, I can definitely see more of
Speaker:an operator skew going forward for
Speaker:anyone that's in a company because,
Speaker:you know, this becomes much more
Speaker:about judgment, decisions,
Speaker:system level thinking, and much less
Speaker:about actual execution of whatever
Speaker:program.
Speaker:It's interesting, I was talking
Speaker:to one of our software developers
Speaker:the other day, and he was saying
Speaker:to me, his argument was that he
Speaker:feels like in a weird way, we've
Speaker:gone back 25 years into
Speaker:more sort of like weird waterfall
Speaker:in a way whereby if you're a product
Speaker:manager, You need to be doing much
Speaker:more descriptive,
Speaker:out-of-the-box,
Speaker:prompting specifications of what
Speaker:you're actually looking for with
Speaker:some level of clarity, going into
Speaker:Claude when you start moving from
Speaker:that point to actually create
Speaker:production code, and that the
Speaker:so-called PRD descriptions are kind
Speaker:of back with product managers.
Speaker:I also agree that there's stuff
Speaker:that's like back 20 years
Speaker:or 25 years.
Speaker:I just wasn't close to product
Speaker:development. So it's not the one
Speaker:that I'm thinking about.
Speaker:The one that.
Speaker:I do think about as a
Speaker:CEO and anybody who's in charge of
Speaker:infosec should be thinking about is
Speaker:how much
Speaker:is sitting on people's local drives
Speaker:in a way that hasn't happened since
Speaker:2003.
Speaker:Because we're sucking everything out
Speaker:of the cloud, downloading it,
Speaker:feeding it back up to Claude,
Speaker:or whatever you're using.
Speaker:Or you're moving things onto your
Speaker:local drives, like all of it to get
Speaker:data closer to Claud.
Speaker:If people lost their laptops now,
Speaker:it would be such a bigger deal
Speaker:than it has been for the last 15
Speaker:years.
Speaker:You know, it's interesting.
Speaker:We just had this conversation the
Speaker:other day, but this new reality
Speaker:where software development,
Speaker:in a way, the job is done,
Speaker:right?
Speaker:And the question of in your
Speaker:company or in any company, you're
Speaker:gonna have certain developers that
Speaker:are on AI agents
Speaker:and using them wholesale
Speaker:to create their code.
Speaker:And what they're doing else we
Speaker:simply doing code reviews before it
Speaker:goes into production you have
Speaker:another band of your developers that
Speaker:there's still this kind of gray area
Speaker:where they're starting to take a
Speaker:look at using agents properly and so
Speaker:on but they haven't really vector
Speaker:themselves hard into it where some
Speaker:people are going hard at right now
Speaker:they have another bended developer
Speaker:where they kind of like either
Speaker:not interested don't want to
Speaker:can't see the future what have you
Speaker:knows that band of individual and
Speaker:i guess for companies right now
Speaker:doing.
Speaker:Kind of what's sensible, I think,
Speaker:which is to migrate out the people
Speaker:that are not down with it, taking
Speaker:the gray zoners and trying to like
Speaker:enable them and push them hard into
Speaker:the kind of AGI-pilled
Speaker:environment.
Speaker:And then the ones that are already
Speaker:on it, obviously that's fantastic.
Speaker:But definitely there's like some
Speaker:level of organizational stewardship
Speaker:from a CEO perspective.
Speaker:I think that needs to occur to like
Speaker:just recognize this, which is
Speaker:software development is a
Speaker:dead end job.
Speaker:And if we recognize that endpoint,
Speaker:the question now in companies is
Speaker:what do you do with that?
Speaker:How do you best enable the
Speaker:gray zone people, how do you best
Speaker:enable people that are not down with
Speaker:it, and how do you best kind of
Speaker:discontinue to support the ones that
Speaker:are going hard at it?
Speaker:Yeah. I mean, that's why we're doing
Speaker:quarterly training and
Speaker:consistently combining
Speaker:quarterly training with time
Speaker:to then build stuff and
Speaker:build out, you know, play with the
Speaker:new skills, take the time to build
Speaker:the rest of the infrastructure.
Speaker:You know, cause every time, every
Speaker:quarter things have changed so
Speaker:much from the previous three months
Speaker:that there's a bunch of new
Speaker:things that you can take advantage
Speaker:of built in so that your job is
Speaker:better. I agree that coding...
Speaker:In and of itself is a dead end job,
Speaker:but I think technologists are
Speaker:not. So the understanding
Speaker:of how it fits together,
Speaker:the precision of it, how to
Speaker:formulate and work through and
Speaker:articulate the
Speaker:problems that need to be solved and
Speaker:also validate that it is going to
Speaker:solve the problem, that
Speaker:thinking isn't going away.
Speaker:Yeah, and this is where product
Speaker:managers, designers, engineers
Speaker:that have more of a customer-facing
Speaker:orientation, there's gonna be like a
Speaker:weird blending of people.
Speaker:The competencies are still there to
Speaker:your point, but you're gonna see
Speaker:much more, I suspect,
Speaker:engineers being asked,
Speaker:forced to deal much more directly
Speaker:with customers or customer
Speaker:discovery or more of that front end
Speaker:of like validating actual value
Speaker:themselves as opposed to like a
Speaker:PM doing it on their behalf.
Speaker:So I think people who identify
Speaker:as being builders or who really like
Speaker:building are the ones who
Speaker:are going to.
Speaker:So here's another thought for you.
Speaker:So this idea that if
Speaker:anyone's building code,
Speaker:whether it's a product manager,
Speaker:designer, engineer, or other people,
Speaker:you have a bunch of people,
Speaker:including the engineers themselves,
Speaker:that are committing code from
Speaker:Claude and nobody has looked at
Speaker:it. They're just like, yeah, this
Speaker:works, it's committed, and it's
Speaker:doing its job effectively.
Speaker:But no human being at that point
Speaker:really understands what they've just
Speaker:committed into code effectively.
Speaker:So it goes into the code base.
Speaker:And let's say two months down the
Speaker:road, you're having massive
Speaker:stability issues and everything goes
Speaker:down.
Speaker:So because nobody actually
Speaker:understands the code base anymore,
Speaker:you start using Claude again to try
Speaker:to debug what is happening.
Speaker:Claude leads you in a direction.
Speaker:That direction is based on
Speaker:Claude telling you where it thinks
Speaker:it's at. Claude is less good at
Speaker:doing this right now and
Speaker:oftentimes you go off in wrong
Speaker:directions effectively and what one
Speaker:of the senior...
Speaker:Developers was telling me was that
Speaker:he was looking at Claude's direction
Speaker:for the debugging process so that
Speaker:some of the developers were going to
Speaker:focus on. He looked at it and said,
Speaker:this is bullshit, that is totally
Speaker:wrong, it's actually over here
Speaker:somewhere.
Speaker:They redirected their efforts to
Speaker:that other spot that he'd identified
Speaker:and lo and behold that's where the
Speaker:bug was effectively.
Speaker:So what he was suggesting to me was
Speaker:this kind of like software
Speaker:architecture design code
Speaker:review on the input side, looking
Speaker:at what Claude is telling you from a
Speaker:debugging standpoint on the flip
Speaker:side and being critical of that.
Speaker:That critical thinking is still
Speaker:required.
Speaker:But inherently, as we all are,
Speaker:including myself, we're all
Speaker:inherently lazy, right?
Speaker:So we're kind of like, code reviews,
Speaker:that's boring, I don't want to do
Speaker:that, the debugging thing, Claude
Speaker:must be right, I'm just gonna not
Speaker:think so much and just allow it to
Speaker:tell me what to do.
Speaker:So what I'm wondering out
Speaker:loud is, like is there
Speaker:a space for,
Speaker:not just a technologist on the
Speaker:customer-facing side, but some
Speaker:technologists for like the software
Speaker:code base itself where there's
Speaker:a different set responsibilities for
Speaker:someone.
Speaker:To do some of the stuff that I think
Speaker:is going to be missing.
Speaker:100%. That's part of what I meant by
Speaker:the technologists.
Speaker:You can't just
Speaker:prompt Claude and walk away and
Speaker:not take responsibility for Claude's
Speaker:output in the same way that
Speaker:on the business side, I wouldn't say
Speaker:to Claude, here are
Speaker:all of our numbers for the last
Speaker:months. Look at my emails and
Speaker:write me a board summary that I
Speaker:can send to the board without
Speaker:editing.
Speaker:And walk away.
Speaker:Done.
Speaker:And walk away and just be like,
Speaker:after you've written it, just send
Speaker:it to the board, done.
Speaker:You wouldn't do that.
Speaker:And so why in the world do you
Speaker:think, even if you spend quite a
Speaker:long time prompting Claude, that you
Speaker:would just push it without checking?
Speaker:Like we're not at that level of
Speaker:intelligence unless you have really
Speaker:built in a
Speaker:huge amount of infrastructure to
Speaker:contain Claude.
Speaker:All right, so we've gone on like a
Speaker:wild tangent here and all sorts of
Speaker:things. We've got a great topic
Speaker:today, which is puzzle setting, not
Speaker:goal setting.
Speaker:We have an amazing guest for this,
Speaker:which is Radhika Dutt.
Speaker:She's the author of Radical Product
Speaker:Thinking, the New Mindset for
Speaker:Innovating Smarter, and a
Speaker:former chief product officer for
Speaker:MovePrice.
Speaker:So with Radhica,
Speaker:she was talking about, and
Speaker:this is a quote from her, goals
Speaker:and targets were designed to kill
Speaker:that internal drive.
Speaker:Where you're then focusing on
Speaker:external measures as if these
Speaker:external drivers are needed to
Speaker:motivate you.
Speaker:And I guess the question is,
Speaker:do you really need to have actual
Speaker:targets to kind of like focus
Speaker:people and to motivate people?
Speaker:And I think she was suggesting in
Speaker:her puzzle framework, there was
Speaker:less need for the actual KRs
Speaker:themselves as opposed to the
Speaker:objective.
Speaker:What do you make of that?
Speaker:My very first reflection is, did a
Speaker:leadership offsite last yesterday,
Speaker:and we had a whole conversation
Speaker:about OKRs, and I entirely forgot
Speaker:about this conversation, and now I'm
Speaker:just kicking myself.
Speaker:I'm like, why? Why didn't I
Speaker:bring this forward as an alternative
Speaker:of what we should be doing, because
Speaker:you know that I'm not a massive
Speaker:believer in OKR.
Speaker:And I think we ended up landing
Speaker:on not doing
Speaker:OKR, but the
Speaker:leaders of the largest Teams.
Speaker:Figuring out the model for their
Speaker:teams.
Speaker:So sales is in effect,
Speaker:you know, running the cadences that
Speaker:a sales team would run and
Speaker:engineering or running sprints, but,
Speaker:and having a roadmap. But I'm
Speaker:wondering, now I just want to
Speaker:bring it in. I know I'm supposed to
Speaker:answer the question, but it's just
Speaker:like kicking myself.
Speaker:Like I really wish we'd had this
Speaker:conversation like last week.
Speaker:Part of it I think depends on the
Speaker:size of the company, but.
Speaker:It feels to me a lot more true
Speaker:than OKRs.
Speaker:OKR's are just.
Speaker:They can be very rigid and people
Speaker:can end up gaming the
Speaker:system and caring more about getting
Speaker:the right key result than solving
Speaker:the underlying issues.
Speaker:And so whether it's a puzzle,
Speaker:whether it is a key result, I don't
Speaker:think matters as much as,
Speaker:and by calling it a puzzle I think
Speaker:you reset the
Speaker:vibe. I'm almost feeling like it's a
Speaker:masculine and a feminine approach to
Speaker:it. So like the masculine approach
Speaker:is very like, okay, R and let's
Speaker:go into fight and like very
Speaker:straight. And the
Speaker:puzzle is...
Speaker:Let's work together, let's
Speaker:collaborate, let's talk about this
Speaker:and look at it from every direction
Speaker:and is a bit kind of more
Speaker:rounded and not
Speaker:relaxed, but like we could
Speaker:put a little bit more fun in and
Speaker:like what we're gonna do is
Speaker:fundamentally solve the problem
Speaker:rather than drive and
Speaker:deliver.
Speaker:Yeah, so I agree with you
Speaker:completely. I think part of this is,
Speaker:I think people become a slave to the
Speaker:KR or they become a slave to like
Speaker:crafting the right KR or the become
Speaker:a slave to only caring about
Speaker:that singular number and
Speaker:pervert what the real intent is of
Speaker:the actual KR itself and don't
Speaker:recognize that throughout the
Speaker:discovery process that may
Speaker:change the entire game whereby that
Speaker:KR is entirely irrelevant or the
Speaker:number makes no sense for a variety
Speaker:of reasons and if they're not to
Speaker:that, open-minded enough to that.
Speaker:I.e. The puzzle orientation, they're
Speaker:going to end up doing the wrong
Speaker:thing.
Speaker:And the manager at some point will
Speaker:be satisfied because they've hit
Speaker:their KR, but then it'll become
Speaker:like, well, what was the point?
Speaker:Why do we bother to do this in the
Speaker:first place? Because it had no
Speaker:business impact whatsoever on
Speaker:the trajectory of the company, yet
Speaker:we hit our KR.
Speaker:It's the classic, I've delivered and
Speaker:I'm done and I am very happy as an
Speaker:individual or as a team, but
Speaker:ultimately from a business outcome
Speaker:standpoint, you've done jack shit
Speaker:and it's had no impact.
Speaker:That was the Cassie Young
Speaker:episode on first
Speaker:team, the top team, and
Speaker:you know, here marketing is saying,
Speaker:look, everything's green and the
Speaker:entire business is on fire.
Speaker:So the other element that Radhika
Speaker:had talked about was a puzzle means
Speaker:you have to stay within the
Speaker:discomfort, not knowing the answers
Speaker:and embracing the not knowingness
Speaker:in terms of your first step.
Speaker:What do you make of that in the
Speaker:context of OKRs?
Speaker:I don't know if it's in the context
Speaker:of OKRs or more broadly
Speaker:the context of life,
Speaker:like sitting, being comfortable with
Speaker:the discomfort is
Speaker:critical to survival,
Speaker:like generally in the
Speaker:world and particularly now.
Speaker:Like one of the things that I
Speaker:tell my kids, because it's one of
Speaker:the things I tell myself,
Speaker:is when there's a setback,
Speaker:this really feels horrible, this is
Speaker:really uncomfortable.
Speaker:I have survived other setbacks
Speaker:and what this will give me
Speaker:is a reliance to know that I can
Speaker:survive this one and the next one so
Speaker:I'm not afraid of discomfort because
Speaker:I know I can survive it.
Speaker:And I think if you can instill that
Speaker:in your teams right now, we
Speaker:can have a need to
Speaker:solve problems.
Speaker:It's really powerful.
Speaker:Although another thing just popped
Speaker:into my mind is We've been talking
Speaker:a lot about Myers-Briggs at
Speaker:work. I'm not a big believer of
Speaker:Myers- Briggs in terms of like when
Speaker:you put it all together that it's
Speaker:realistic, but I do find
Speaker:the individual four pieces helpful.
Speaker:And the final piece is like,
Speaker:I can't remember, it's P and J,
Speaker:judging and perceiving,
Speaker:which is such a bizarre, like I
Speaker:kind of feel like they're synonyms,
Speaker:but people who are judging
Speaker:are very, very time bound
Speaker:and feel comfortable when they've
Speaker:made a decision and people that are
Speaker:perceiving.
Speaker:Feel very comfortable before they've
Speaker:made a decision and before they're
Speaker:tied down. And I am a
Speaker:very natural J, and every
Speaker:CEO I've ever worked with is a very
Speaker:naturally and highly-preferenced P,
Speaker:and it's been such a clash.
Speaker:But now that I'm a CEO, I
Speaker:have to try and tamp down my
Speaker:J and leave space for
Speaker:the indecision and leave a space for
Speaker:doing the puzzle and actually
Speaker:remove some of my execution
Speaker:urge.
Speaker:And so I think it's a helpful
Speaker:structure.
Speaker:Yeah, no, I hear on this because I
Speaker:feel like I ride the lightning of
Speaker:this as well in some ways because
Speaker:just with the past week that I've
Speaker:had, I've had to make decisions at
Speaker:pace and I get
Speaker:pretty excited and jazzed up to
Speaker:make decisions like I'm a natural
Speaker:born decision maker.
Speaker:And sometimes it catches me out
Speaker:because I'm making calls either too
Speaker:fast with not enough information,
Speaker:lack of context, all sorts of
Speaker:things. So sometimes it can be an
Speaker:asset, but sometimes it's gonna hurt
Speaker:you. And we're just having a call
Speaker:with one of our external recruiters.
Speaker:And I was telling the recruiter
Speaker:alongside of our internal staff, I'm
Speaker:like, we're doing this, you're not
Speaker:doing that.
Speaker:And then at some point he piped up
Speaker:and said, hey, Brandon, like we
Speaker:actually have some skills in this
Speaker:particular area that they may not be
Speaker:aware of. And this is what the
Speaker:skills look like.
Speaker:I'm, like, oh, fine, love that.
Speaker:Let me pull back what I just
Speaker:decided. We're doing that now.
Speaker:I'm getting out of myself slightly
Speaker:from a decision standpoint, I would
Speaker:say.
Speaker:So I think having this conversation
Speaker:helps us be aware of
Speaker:when you do push for a decision and
Speaker:when you maybe push for micro
Speaker:decisions but leave the
Speaker:full solution to unfold.
Speaker:Yeah, yeah, being open to it.
Speaker:That makes complete sense.
Speaker:Last question, Radhika talked about
Speaker:the three O's from her point
Speaker:of view, which is the key bits are
Speaker:observation, the open questions,
Speaker:and the objective.
Speaker:So when you think about the 3 O's as
Speaker:kind of like her puzzle
Speaker:way of going forward as
Speaker:opposed to OKRs, how much do you
Speaker:love the observation, open questions
Speaker:and objective? And in particular, on
Speaker:the observation side, do you have
Speaker:any thoughts on that one?
Speaker:I think it just makes a lot of sense
Speaker:and I think you can tell that she's
Speaker:a product person who is now
Speaker:thinking through and standardizing
Speaker:the process that she has created and
Speaker:figuring out what it is that you do.
Speaker:So you observe what's
Speaker:happening, get really clear
Speaker:on that, ask the questions
Speaker:that aren't yes no questions.
Speaker:There's a bit of a debate as to
Speaker:whether or not open questions
Speaker:actually matter. I think it's more
Speaker:around, like, a philosophy of the
Speaker:mindset, because...
Speaker:You can ask a very open question to
Speaker:somebody who doesn't care and
Speaker:they'll still give you a closed
Speaker:answer and you can ask the closed
Speaker:question to someone who cares a lot
Speaker:and they're going to give you an
Speaker:open answer.
Speaker:So I think it's more inviting
Speaker:a little bit more of that P
Speaker:versus J.
Speaker:So, you know, like inviting the
Speaker:conversation, inviting not needing
Speaker:an answer and
Speaker:surfacing everything that you
Speaker:need to know in service
Speaker:of an objective.
Speaker:You're absolutely right.
Speaker:I think Radhika, as a former product
Speaker:person, she's taken effectively the
Speaker:idea of customer discovery and
Speaker:applying it to OKRs and
Speaker:re-vectoring it as puzzles.
Speaker:So she's very much taking her
Speaker:background, I think, in kind of this
Speaker:new thesis that she's presenting.
Speaker:It's not really new, is it?
Speaker:It's just kind of product
Speaker:management, customer discovery
Speaker:repackaged into the OKR
Speaker:world of running companies.
Speaker:And a discovery that it works, yeah.
Speaker:Yeah, no, exactly.
Speaker:The interesting bit is this word
Speaker:observation that she's stuck in
Speaker:here. I don't know if you recall our
Speaker:talk with Keith Wallington as to the
Speaker:CEO's job.
Speaker:He said one of the five
Speaker:jobs of the CEO is observation.
Speaker:So it's just interesting, word-wise
Speaker:at least, that Keith saw that from
Speaker:a CEO perspective to spend time on
Speaker:that. And she's kind of saying the
Speaker:same thing.
Speaker:So why don't we park it here and get
Speaker:into our conversation with Radhika.
Speaker:I am not the biggest fan of OKRs,
Speaker:but for me, it feels like the least
Speaker:worst option.
Speaker:And so when you approached us
Speaker:and said you had an alternative
Speaker:to OKR in a different approach,
Speaker:I just got so excited.
Speaker:And I think we ended up speaking for
Speaker:about an hour, and I was just going,
Speaker:what do we do? How do we do it?
Speaker:And the way that I summarized it is
Speaker:looking at everything as puzzles.
Speaker:And I love puzzles.
Speaker:So, I do the crossword puzzle,
Speaker:wordle, connections.
Speaker:All I only do three of
Speaker:the LinkedIn puzzles every single
Speaker:day.
Speaker:And so for me, the idea of looking
Speaker:at work as a puzzle and introducing
Speaker:more play, particularly when things
Speaker:are so stressful is
Speaker:a stroke of genius.
Speaker:So now I'm going to let you talk and
Speaker:I'm just going to say,
Speaker:why don't you introduce
Speaker:us to this puzzle concept
Speaker:and puzzle framework?
Speaker:You know, but I love your preamble
Speaker:to all of this.
Speaker:This is what I'd been seeing for a
Speaker:really long time in my career.
Speaker:And I couldn't articulate quite why
Speaker:goals and OKRs weren't working.
Speaker:What I was feeling was we
Speaker:just have so much passion
Speaker:and internal drive.
Speaker:And it's almost like goals
Speaker:and targets were designed to
Speaker:kill that internal drive where
Speaker:you're then focusing on
Speaker:external measures,
Speaker:but not just measures, external
Speaker:drivers as if you
Speaker:don't have this internal drive that
Speaker:these external drivers are needed
Speaker:to motivate you.
Speaker:It was fascinating for me for a
Speaker:long time to see the
Speaker:kind of twisted and perverse effects
Speaker:that goals and targets had.
Speaker:This puzzle concept came to
Speaker:me because I
Speaker:just instinctively started
Speaker:working with a team in this way.
Speaker:So let me share this example.
Speaker:I was working with this Greek
Speaker:company, I still am.
Speaker:The maritime industry.
Speaker:The way this started was because the
Speaker:CEO had brought me in.
Speaker:They used goals and OKRs
Speaker:and sales had stalled in 2023.
Speaker:When I came in, the team had
Speaker:been trying to go after this market
Speaker:and they were hitting some OKR's,
Speaker:not hitting others.
Speaker:But it was a brilliant
Speaker:group of people, super smart
Speaker:people. All were data scientists,
Speaker:mathematicians, applied
Speaker:mathematicians.
Speaker:Like really fascinating people.
Speaker:And clearly, there was passion when
Speaker:I was talking to them.
Speaker:And yet, when I actually was
Speaker:seeing the work, I wasn't seeing
Speaker:that passion translated into
Speaker:that work.
Speaker:This was when we started looking
Speaker:at it differently.
Speaker:Instead of focusing on goals,
Speaker:targets, and looking at, okay, is
Speaker:this feature going to move this okay
Speaker:or not, we just
Speaker:started with this blank slate
Speaker:saying, okay wait, let's just
Speaker:look at what is the problem
Speaker:we're solving? And we started
Speaker:thinking about it as a puzzle.
Speaker:You know, I just wanted to know, how
Speaker:are things going?
Speaker:What is it that customers are really
Speaker:experiencing?
Speaker:What is working? What is not?
Speaker:And so we started defining the
Speaker:puzzle. So this was a maritime
Speaker:platform, a data analytics platform.
Speaker:And the puzzle was, it's fascinating
Speaker:that only tech
Speaker:savvy brokers in the
Speaker:maritime industry are using this
Speaker:platform.
Speaker:So fascinating. Why only tech savvy
Speaker:people?
Speaker:Why only brokers?
Speaker:Why aren't people who own shipping
Speaker:vessels, or who own cargoes,
Speaker:why aren't they using this platform?
Speaker:Why just brokers?
Speaker:And so these are questions that we
Speaker:didn't have answers to, right?
Speaker:And when I started asking these
Speaker:questions, people are like, yeah,
Speaker:you're right. We don't know this.
Speaker:A puzzle mindset is
Speaker:different because goals and targets
Speaker:come at it from, we know the
Speaker:answer. Just achieve these numbers,
Speaker:that gets you what you need.
Speaker:That means progress.
Speaker:Whereas a puzzle means you
Speaker:have to stay with the discomfort
Speaker:that we don't know
Speaker:the answers.
Speaker:We're going to have to figure this
Speaker:out.
Speaker:That embracing the not knowing
Speaker:is the first step of a puzzle that
Speaker:completely shifted the mindset.
Speaker:So we started talking to people who
Speaker:are both customers, people who
Speaker:weren't customers, to figure out
Speaker:what's really going on.
Speaker:Why aren't these people using it?
Speaker:And it led us to questions like, how
Speaker:do people who are shipping vessel
Speaker:owners use, what do they do in
Speaker:their day? How do they work?
Speaker:You know, what is their mental
Speaker:model? How is it different from
Speaker:how brokers work?
Speaker:So we started asking all these
Speaker:questions and we learned so much.
Speaker:We were observing what was
Speaker:actually happening, not just looking
Speaker:at data and not looking at
Speaker:shortcuts.
Speaker:We were absorbing this puzzle.
Speaker:It's like looking at a Rubik's Cube
Speaker:and really moving things around and
Speaker:saying, how does this thing work?
Speaker:And now, now that we had this
Speaker:observation, we
Speaker:were looking at this puzzle, we had
Speaker:a clearer definition.
Speaker:Now we could attempt this puzzle.
Speaker:And so I'll pause there for a
Speaker:moment, but I think there's lots to
Speaker:unpack even there.
Speaker:And then I can talk about how we
Speaker:solve the puzzle.
Speaker:One of the things that struck me
Speaker:immediately was, and you said
Speaker:it very in passing, you were
Speaker:really observing things rather than
Speaker:just looking at the data and
Speaker:short-cutting, and I was like, oh
Speaker:yeah, I shortcut.
Speaker:I look at the date, I
Speaker:make a close enough guess,
Speaker:and then I say, now we need to build
Speaker:X amount of pipeline, or now
Speaker:we'll need to ship these three
Speaker:things and move immediately
Speaker:into the goal setting side
Speaker:and skip the discomfort.
Speaker:But there's also
Speaker:an element...
Speaker:Where I'm wondering,
Speaker:you knew the problem.
Speaker:And so like, the part that we're
Speaker:missing is the beginning of what
Speaker:were the OKRs, or what was the OK
Speaker:that didn't work versus figuring
Speaker:out the problem to solve, because
Speaker:presumably they were trying to solve
Speaker:the problem through the OK.
Speaker:Yeah, we were.
Speaker:We wanted better user engagement.
Speaker:That was one of the OKRs, better
Speaker:user engagement from all these
Speaker:different types of users, right?
Speaker:We wanted to have
Speaker:more customers who are not
Speaker:just brokers. We want to expand to
Speaker:this other user base.
Speaker:We wanted to expand beyond
Speaker:just a small group of
Speaker:brokers.
Speaker:And so this is when we started
Speaker:looking at the data to see, well,
Speaker:who is using this?
Speaker:That was when we could tell,
Speaker:okay, it's mostly tech-savvy brokers
Speaker:using this.
Speaker:And yeah, very few other people are
Speaker:using this, right?
Speaker:So yes, you're right that we did
Speaker:have OKRs saying we should do
Speaker:this, this, and this.
Speaker:OKR's don't tell you what is it
Speaker:that's not working, right.
Speaker:And so we were hitting some of these
Speaker:numbers. We were increasing some
Speaker:usage, but not
Speaker:enough. Like it wasn't truly
Speaker:a radical shift.
Speaker:And do you know what you were saying
Speaker:about...
Speaker:How we want to jump to the quick
Speaker:fixes, that was the temptation at
Speaker:this company too.
Speaker:When I first joined, they were
Speaker:looking at the data and they were
Speaker:saying, aha, we know what we
Speaker:need to do. All the customers are
Speaker:complaining that filtering
Speaker:on this platform to get to
Speaker:the data you want, filtering is
Speaker:really hard.
Speaker:And so we need to make
Speaker:filtering easier.
Speaker:Let's work on the UX to be able
Speaker:to change filtering.
Speaker:And even there, right, we wanted to
Speaker:jump to the quick fixes.
Speaker:Yes, let's work on filtering
Speaker:UX changes, but don't
Speaker:make radical shifts because that's
Speaker:going to take a long time for us to
Speaker:build.
Speaker:Let's do something that can
Speaker:increase our metrics and let's
Speaker:try something small first.
Speaker:So this is exactly what you're
Speaker:talking about. And that was the trap
Speaker:that we were falling into
Speaker:until we said, but hang on,
Speaker:let us first observe what is the
Speaker:puzzle.
Speaker:Is filtering truly why
Speaker:people who are in different roles,
Speaker:not brokers?
Speaker:Is filtering truly the reason
Speaker:that cargo owners or
Speaker:ship owners are not using this
Speaker:product?
Speaker:We didn't think, like I didn't,
Speaker:think so. It wasn't obvious
Speaker:to me that filtering was the main
Speaker:reason.
Speaker:The people who are using the product
Speaker:were complaining about filtering.
Speaker:The unknown unknowns were what
Speaker:we didn't know.
Speaker:The people were not using it,
Speaker:there was no data on them.
Speaker:The way them
Speaker:suddenly starting to think about it
Speaker:is maybe they work together
Speaker:or you know so you can use
Speaker:OKRs in terms of what are the things
Speaker:to identify what the not
Speaker:the solution but what the
Speaker:outcome is and like what
Speaker:you're trying to get to but
Speaker:so there was a
Speaker:very clear business problem which is
Speaker:you need to have more
Speaker:users and users across different
Speaker:bases and measuring the
Speaker:success of that is important.
Speaker:But what ends up happening I think a
Speaker:lot in businesses is you set out the
Speaker:OKRs, you set out the numbers, and
Speaker:then people immediately game the
Speaker:system or it's like it's a quarter.
Speaker:How do we do it as fast as possible?
Speaker:How do you do it efficiently?
Speaker:How do cut corners so it
Speaker:looks like we're doing it, but
Speaker:really all we're doing is measuring
Speaker:it slightly differently than we were
Speaker:before and we're not actually
Speaker:getting to the
Speaker:true unlock.
Speaker:And so it's the two together.
Speaker:You need to identify what what needs
Speaker:to change, but then not
Speaker:make reaching it
Speaker:the goal.
Speaker:What you need to make is unlocking
Speaker:it and truly understanding the
Speaker:problem, the goal?
Speaker:Exactly.
Speaker:So, when you set a goal or
Speaker:a target, the incentive you create
Speaker:for everyone is to show you,
Speaker:tada, look, I'm a high performer,
Speaker:I've hit whatever numbers you
Speaker:wanted.
Speaker:And so, the incentives you create by
Speaker:default is to get everyone
Speaker:to tell you things are going great
Speaker:and I have the numbers to
Speaker:prove it.
Speaker:And you know, in fact, Intel's
Speaker:legendary CEO, Andy Grove,
Speaker:he wrote in his book, Leaders are
Speaker:the last to know.
Speaker:And this is precisely why,
Speaker:because when you set a goal or a
Speaker:target, everyone is there to show
Speaker:you. And it's not even malicious,
Speaker:right? It's not that they're
Speaker:necessarily gaming numbers on
Speaker:purpose.
Speaker:Even subconsciously, what happens
Speaker:is you set a target and
Speaker:people want to look at the positive
Speaker:numbers and present
Speaker:to you those positive numbers to
Speaker:say, tada, look, things are going
Speaker:well. And what you really want
Speaker:people to do is to play detective,
Speaker:look at the bad numbers too.
Speaker:And say, huh, what just happened
Speaker:there? You know, is there an
Speaker:opportunity?
Speaker:Is that a puzzle?
Speaker:What went wrong?
Speaker:And what can we do differently based
Speaker:on that, right? And that's what we
Speaker:miss when we set targets.
Speaker:And so what you're alluding to
Speaker:is how do you use this
Speaker:in an OKR format?
Speaker:So what I do with puzzle setting
Speaker:is I call it the three
Speaker:O's of puzzle setting.
Speaker:So the first O is the observation.
Speaker:So the observation in this case,
Speaker:right, was.
Speaker:That only tech savvy brokers
Speaker:are using this product,
Speaker:none of the others are.
Speaker:We want to address the tech-averse
Speaker:people, we want to address ship
Speaker:owners, the cargo owners.
Speaker:The second O is
Speaker:the open questions.
Speaker:These are things that you genuinely
Speaker:don't have answers to.
Speaker:This is where we don't know how
Speaker:these other people think in this
Speaker:business.
Speaker:How do they think?
Speaker:How is their mental model different?
Speaker:And so that's the second O.
Speaker:And the third O
Speaker:The objective, and by the way, the
Speaker:objective is named very deliberately
Speaker:to be similar to OKR's
Speaker:objective, right?
Speaker:Because that objective is where you
Speaker:summarize this puzzle.
Speaker:And the summary of this particular
Speaker:puzzle was, how do we
Speaker:solve this puzzle to get back
Speaker:to the growth trajectory we were on
Speaker:by expanding to
Speaker:all of these different sorts of
Speaker:users who are not just the
Speaker:tech-savvy brokers?
Speaker:And so if you're using
Speaker:OKRs instead of just having
Speaker:arbitrary you know,
Speaker:objectives like grow sales or
Speaker:increase user engagement
Speaker:or whatever that is, right?
Speaker:Set the whole puzzle in this very
Speaker:clear way so your team knows
Speaker:exactly what they're going after
Speaker:in terms of puzzle solving next.
Speaker:And are those O's in order?
Speaker:Absolutely. So you observe,
Speaker:I can't remember the middle one, and
Speaker:then objective.
Speaker:The open questions.
Speaker:Open questions, so that's part, so
Speaker:you observe ask open questions,
Speaker:figure out what's going on, set
Speaker:your objectives, and then
Speaker:solve the problem.
Speaker:Exactly.
Speaker:Let's take a sales example, right?
Speaker:So the sales example might be,
Speaker:you know, instead of just setting
Speaker:the target as grow to
Speaker:X million at the end of this year,
Speaker:the puzzle I might set is,
Speaker:we do want to get to X Million, but
Speaker:here's the puzzle I see.
Speaker:We grew at a certain rate in the
Speaker:last three years and growth has
Speaker:stalled, right? That's the
Speaker:observation.
Speaker:The open questions are, I
Speaker:don't know what just happened.
Speaker:Is it that maybe?
Speaker:Something is fundamentally shifted
Speaker:because of AI that is not obvious,
Speaker:so even though our market isn't
Speaker:related, there's still something
Speaker:that's affecting our business.
Speaker:Maybe it's that we were targeting
Speaker:early adopters really well, but the
Speaker:mass market, this message
Speaker:is not resonating for them, right?
Speaker:There might be other such open
Speaker:questions that we genuinely don't
Speaker:know what's happening.
Speaker:And then the objective is the
Speaker:summary of this puzzle.
Speaker:How do we get back to that growth
Speaker:trajectory by figuring this
Speaker:out.
Speaker:The way that you're talking about
Speaker:it, it strikes me that these are the
Speaker:conversations that we have as a
Speaker:leadership team, and it's a lot
Speaker:of how to frame
Speaker:the strategy and understanding the
Speaker:full context, but
Speaker:we don't always then explain it to
Speaker:the rest of the team.
Speaker:So is part of this around a
Speaker:way of explaining and
Speaker:getting the conversations out of the
Speaker:leadership and into the rest to the
Speaker:organization?
Speaker:Very much so.
Speaker:And
Speaker:And it creates a level of alignment
Speaker:that is so different from
Speaker:how we traditionally communicate
Speaker:strategy.
Speaker:What I often see in companies is,
Speaker:there is discussion that happens at
Speaker:a leadership level, but what gets
Speaker:handed down to
Speaker:others across the organization
Speaker:is a very fluffy two-page strategy
Speaker:document that says, we're going to
Speaker:focus on our core, we
Speaker:are going to be customer-focused,
Speaker:and it doesn't mean all
Speaker:that much for people.
Speaker:Or it's a particular initiative that
Speaker:is listed, instead this
Speaker:defines sort of puzzles that
Speaker:we're setting out to solve.
Speaker:And each puzzle, there might be a
Speaker:sales component to it.
Speaker:The same sales puzzle might have a
Speaker:product component to, it because
Speaker:maybe the product was resonating
Speaker:for the early adopter, but it's
Speaker:not resonating for the mass market.
Speaker:Like there's a lot that might be
Speaker:even cross-functional that needs to
Speaker:be figured out.
Speaker:So that's very much around the
Speaker:puzzle setting piece.
Speaker:And I have some questions
Speaker:on how big are the teams,
Speaker:how many puzzles can you solve at
Speaker:one time, like those
Speaker:COO practical questions.
Speaker:And I'm not sure if that's part of
Speaker:the, if we're moving into the puzzle
Speaker:solving piece there or if that still
Speaker:in the setting.
Speaker:The puzzle setting part, right?
Speaker:I think it depends on the level that
Speaker:you're at. As CEO, the
Speaker:sales puzzle that I defined, where
Speaker:it has a sales component,
Speaker:where is our message resonating?
Speaker:Why aren't our deals closing?
Speaker:There might be a piece of that
Speaker:puzzle for the sales team to figure
Speaker:out. There might a product piece for
Speaker:the product team to go figure out,
Speaker:so at a CEO or COO
Speaker:level, you might be setting a bigger
Speaker:puzzle, right, and maybe
Speaker:as a head of product, there might
Speaker:be.
Speaker:A smaller version of that
Speaker:puzzle.
Speaker:And in this particular case, the
Speaker:puzzle was really at a product
Speaker:level, which was why aren't
Speaker:we growing beyond this group, right?
Speaker:And then once we delved into
Speaker:that, there were smaller puzzles.
Speaker:So as we get into puzzle solving,
Speaker:I'll share with you some examples of
Speaker:how solving one layer of the
Speaker:puzzle, kind of like the Rubik's
Speaker:cube, you solve one layer and the
Speaker:next layer becomes the next
Speaker:thing that you're solving and you
Speaker:keep going.
Speaker:And, you know, this question that
Speaker:you asked, what it reminds me of was
Speaker:Andy Grove's book.
Speaker:You know, he talks about only the
Speaker:paranoid survive.
Speaker:He talks about how you have to
Speaker:keep experimenting, learning,
Speaker:adapting all the time, right?
Speaker:He doesn't even talk about OKRs,
Speaker:even though he invented OKR,
Speaker:and it came from Peter Drucker's
Speaker:Management by Objectives, but he
Speaker:inventedOKRs.
Speaker:He never once mentioned OKR
Speaker:in only the paranoid survive,
Speaker:it was all about experimentation,
Speaker:learning, adaptation.
Speaker:And with each team
Speaker:and at different levels, you get
Speaker:into different pieces of the puzzle.
Speaker:So is this purely just a framing
Speaker:exercise from top to bottom, because
Speaker:it's kind of the same thing, right?
Speaker:Because whether you call them OKRs
Speaker:or you call the puzzles or you
Speaker:called them whatever, I recognize
Speaker:the framing matters quite a bit and
Speaker:also being bound by rules
Speaker:matters quite a bit in terms of
Speaker:giving freedom for experimentation
Speaker:and so on.
Speaker:But ultimately at the end of any
Speaker:OKR, if they're done well,
Speaker:which they're usually not, but the
Speaker:team, the cross-functional team will
Speaker:have a set of hypothesis or initial
Speaker:. Things they want to put in play to
Speaker:test out as hypothesis to
Speaker:see if it's going to move the needle
Speaker:related to their KR, I suppose.
Speaker:So inherently, those initiatives are
Speaker:puzzles because they have a
Speaker:hypothesis. They're like, yeah, we
Speaker:don't quite know, but we're going to
Speaker:like, this is our first thing we're
Speaker:gonna salvo-wise get out there to
Speaker:see if it actually moves the needle
Speaker:or not. So I guess my question in
Speaker:summary is the puzzle,
Speaker:part of it is part of generally what
Speaker:happens in OKRs at some level.
Speaker:So it's more just like a repackaging
Speaker:and reframing of like what we're
Speaker:doing here as opposed to something
Speaker:more fundamental.
Speaker:You know, what is funny for me is
Speaker:this is actually what I hear from so
Speaker:many OKR experts that,
Speaker:you know, if you just do OKRs
Speaker:right, then you don't run into any
Speaker:of these problems with OKR.
Speaker:The reason OKR aren't working for
Speaker:you is because you haven't done OKR
Speaker:right.
Speaker:This is sort of the refrain that you
Speaker:keep hearing.
Speaker:Here's my challenge to that refrain.
Speaker:It feels like the emperor has no
Speaker:clothes and someone has to call it
Speaker:out because It's
Speaker:not that if you do it right,
Speaker:and I'll give you examples even from
Speaker:John Doar's book, who is the one who
Speaker:evangelized OKRs.
Speaker:Even from his book, I can give you
Speaker:an example of OKR's that are
Speaker:supposedly done right and the
Speaker:ramifications that come from it.
Speaker:OKR create a different mindset.
Speaker:What research has shown about OKR
Speaker:and specifically about
Speaker:setting targets is
Speaker:targets and goals,
Speaker:they work well.
Speaker:When you're doing a repetitive task,
Speaker:when there is one obvious right
Speaker:answer.
Speaker:So research has shown that if you're
Speaker:doing something like stuffing
Speaker:envelopes, if you are doing crunches
Speaker:in a gym, great, set
Speaker:targets, it works brilliantly.
Speaker:If on the other hand, you're doing
Speaker:something that's more like a puzzle,
Speaker:that's akin to something complex
Speaker:where there's no single
Speaker:right answer, that
Speaker:is where goals and targets
Speaker:do not work.
Speaker:That the instruction, do your best,
Speaker:actually works better.
Speaker:Than setting a goal or a target.
Speaker:So why is that, right?
Speaker:And it begs the question, how did
Speaker:we even adopt goal
Speaker:setting as such a fundamental
Speaker:truth in business?
Speaker:And the answer to that, I did
Speaker:research on this because I found
Speaker:this fascinating.
Speaker:Why haven't we used puzzles?
Speaker:Because that seems more obvious.
Speaker:Where did we come up with goal
Speaker:setting? It came from 1940s
Speaker:from Peter Drucker.
Speaker:It was revolutionary at the time.
Speaker:And why did Peter Drucker then
Speaker:come up with this goal-based
Speaker:approach and management by
Speaker:objectives? What problem was he
Speaker:solving? The problem was that he was
Speaker:working with General Motors at the
Speaker:time where the
Speaker:problem they had was motivating
Speaker:people on an assembly line
Speaker:who are doing repetitive tasks.
Speaker:Now it all falls into place.
Speaker:Of course, on
Speaker:this assembly line in the 1940s,
Speaker:there was no automation.
Speaker:It's all repetitive tasks and so
Speaker:goals worked really well, exactly
Speaker:as research shows.
Speaker:And now we use the same approach,
Speaker:even in a manufacturing setting.
Speaker:Look at Boeing.
Speaker:You set production targets and you
Speaker:see the kind of quality issues you
Speaker:have. So it's not a
Speaker:matter of just setting the right
Speaker:OKRs.
Speaker:Sorry, I didn't mean to derail your
Speaker:next step here, but I'm now very
Speaker:curious about the second step.
Speaker:We've set our scene and now we're
Speaker:going into it.
Speaker:Give me the low down here.
Speaker:So puzzle solving is
Speaker:where, instead of proving
Speaker:that I've hit the target or the
Speaker:number, the incentive is different.
Speaker:We're asking three questions in
Speaker:puzzle solving.
Speaker:Until this point, we've looked at
Speaker:the Rubik's Cube and how it works,
Speaker:and puzzle solving is when we take
Speaker:our first attempt at it and we ask
Speaker:three questions, which is how
Speaker:well did this work?
Speaker:And notice the difference, right?
Speaker:How well did it work invites
Speaker:the good and the bad.
Speaker:It's not like a target.
Speaker:I'm not asking a binary question.
Speaker:Did you or didn't you hit the
Speaker:target? I want to know how well it
Speaker:worked. And so the answer,
Speaker:let's say in the sales question,
Speaker:was, okay, we
Speaker:tried this new messaging.
Speaker:How well did it work?
Speaker:The messaging worked well.
Speaker:We got all these meetings with
Speaker:decision makers, but we're not
Speaker:closing the deals.
Speaker:So that's how well that worked.
Speaker:The next question.
Speaker:What did we learn from it?
Speaker:So this is where I say to teams,
Speaker:don't just spit out statistics
Speaker:and data at me,
Speaker:right? Data and stats are super
Speaker:important, but I want you to take
Speaker:the time to figure out what is it
Speaker:telling you? What is actually
Speaker:happening?
Speaker:And so in the sales example, it
Speaker:would be that the
Speaker:message is resonating, we're getting
Speaker:meetings.
Speaker:The problem, the reason why we're
Speaker:not closing the deal is that in
Speaker:addition to this decision maker in
Speaker:the mass market, it turns out
Speaker:there's a new group.
Speaker:That we traditionally had never
Speaker:talked to, and this group is holding
Speaker:up the sale.
Speaker:So that's what have we learned.
Speaker:So now comes the third question,
Speaker:which is based on how well it worked
Speaker:and what you learned, what
Speaker:will you try next?
Speaker:And this is where I say to teams,
Speaker:you know, imagine I give you a magic
Speaker:wand, what would you ask for?
Speaker:So let's start from there where you
Speaker:really rethink things and then we'll
Speaker:pare it down to what we can do.
Speaker:What would you asked for?
Speaker:And in this piece, right, to
Speaker:solve the sales puzzle and what we
Speaker:tried next, One example would be.
Speaker:We're going to try creating material
Speaker:that the decision maker can easily
Speaker:forward to this new group.
Speaker:We're also going to reach out to
Speaker:them directly. We traditionally have
Speaker:never spoken to them.
Speaker:Here's how we might reach out
Speaker:directly. We're gonna do webinars.
Speaker:And now that opens up the next
Speaker:layer of the puzzle.
Speaker:We're trying these things and see
Speaker:how well did it work.
Speaker:What have we learned?
Speaker:What will we try next?
Speaker:It feels like this is how I operate,
Speaker:but I just have never put into a
Speaker:framework. I don't know about you,
Speaker:Brandon. Like it seems like I have
Speaker:these kinds of conversations on a
Speaker:fairly regular basis.
Speaker:Yeah, for sure.
Speaker:Yeah. And I guess I'm just wondering,
Speaker:like, what is the process then?
Speaker:Yeah, and so isn't that fascinating?
Speaker:Like, I agree with you.
Speaker:Intuitively, this is how we work.
Speaker:This is how you solve puzzles.
Speaker:And yet, right, this not how
Speaker:I actually see teams operate.
Speaker:What this gives you is a scaffolding
Speaker:so that what you find is
Speaker:people at different levels, they
Speaker:have different levels of knowledge,
Speaker:skills, and experience.
Speaker:And this scaffolding helps you
Speaker:figure out where is someone at?
Speaker:There have been times where I was
Speaker:working with someone who was a
Speaker:product manager, someone who came
Speaker:from Amazon.
Speaker:She was fantastic at
Speaker:optimizing for numbers and
Speaker:she would often present numbers that
Speaker:looked fantastic.
Speaker:And we started using this framework
Speaker:and I was asking
Speaker:these deeper questions.
Speaker:How well did it work?
Speaker:What have you learned?
Speaker:And I would start to question some
Speaker:of the numbers in the,
Speaker:what have we learned? Like, I don't
Speaker:just want to know that 48% of
Speaker:people are using this.
Speaker:Tell me the details around it.
Speaker:How did you get to the 48%?
Speaker:Is it that they're landing on it or
Speaker:is it that they're going back to it?
Speaker:Like, what is actually happening?
Speaker:I want the details.
Speaker:When I started asking these
Speaker:questions, I would realize how well
Speaker:does someone actually
Speaker:understand what is happening.
Speaker:It's a different level of
Speaker:puzzle solving, right?
Speaker:They're not just telling me numbers
Speaker:to make things look good.
Speaker:We're actually solving the puzzle.
Speaker:And then I want to know, what are
Speaker:you going to try next?
Speaker:All of this tells me exactly where
Speaker:someone is in terms of knowledge,
Speaker:skills, and experience.
Speaker:And it helps me scale leadership,
Speaker:or rather, it helps me scale my
Speaker:own team's efforts.
Speaker:Like, based on who is good at
Speaker:solving what level of puzzles, I
Speaker:know how much to delegate.
Speaker:So that
Speaker:Reminds me of another guest that
Speaker:we had on Jennifer
Speaker:Sonderberg
Speaker:from Board
Speaker:Intelligence, the episode on how to
Speaker:build a company that's smarter than
Speaker:you are.
Speaker:Board Intelligence are a company to
Speaker:build good board reports,
Speaker:like for multinational companies for
Speaker:the most part, where board reports
Speaker:are big and dense
Speaker:and don't share the information that
Speaker:people need to know to actually
Speaker:govern businesses.
Speaker:What they came up with was a
Speaker:questioning framework.
Speaker:And the power of the question,
Speaker:and using that as a way
Speaker:of embedding critical thinking in
Speaker:an organization.
Speaker:And it seems like what you're doing
Speaker:is also solving
Speaker:the puzzle of how do you embed
Speaker:critical thinking in an
Speaker:organization?
Speaker:And the thing that has definitely
Speaker:been my experience with OKRs
Speaker:and goal setting is that
Speaker:it encourages superficial
Speaker:thinking and it encourages
Speaker:moving fast for a result.
Speaker:Rather than the critical
Speaker:thinking. And so you end up with a
Speaker:leadership team that might be
Speaker:thinking critically and everybody
Speaker:else is just executing and
Speaker:cutting corners and moving fast
Speaker:in order to hit numbers or
Speaker:not believing in those numbers and
Speaker:those objectives.
Speaker:And so then just like not doing it
Speaker:anyhow or looking like they are, but
Speaker:knowing that it's unachievable.
Speaker:So I can really see that you
Speaker:need a business plan,
Speaker:you need KPIs, you
Speaker:need.
Speaker:North Star, you need to know where
Speaker:you're going to and some
Speaker:measurements.
Speaker:But OKRs might encourage
Speaker:a lack of
Speaker:critical thinking.
Speaker:Or you can have a lot of critical
Speaker:thinking and use OKR as a tool,
Speaker:but you'd have to be embedding
Speaker:your critical thinking somehow.
Speaker:And if that's solving puzzles or
Speaker:asking questions, that's
Speaker:really what you're trying to
Speaker:achieve.
Speaker:Exactly.
Speaker:So what you often hear in the
Speaker:corporate world are all these trite
Speaker:phrases, right?
Speaker:Like, we have to embrace failure,
Speaker:we've to encourage people to
Speaker:experiment and we have to make it
Speaker:okay to fail.
Speaker:And, you know, when you think about
Speaker:it, it just seems so contrived,
Speaker:right, because you said you
Speaker:love to solve Wordle and
Speaker:all these different puzzles.
Speaker:Let's think about, you know, when
Speaker:you last solved Wordle probably
Speaker:earlier today, when you tried your
Speaker:second attempt, if you didn't get it
Speaker:on your second attempt, did you
Speaker:artificially go through this thought
Speaker:process of, I'm going to embrace
Speaker:failure and it is okay
Speaker:to fail and I'm gonna try this next
Speaker:experiment?
Speaker:No, right?
Speaker:We just sort of instinctively
Speaker:look at something that didn't
Speaker:work and we go, oh, here's what I
Speaker:learned from it, here is what I'm to
Speaker:do and adapt next, right?
Speaker:And I think you're puzzle solving.
Speaker:Strength is why this feels
Speaker:so intuitive to you and you bring it
Speaker:into business.
Speaker:What we want to do is really
Speaker:to spread this passion,
Speaker:but also this drive, this
Speaker:internal drive that people have.
Speaker:We just want to enhance it so that
Speaker:they can use the scaffolding
Speaker:to solve puzzles in an
Speaker:effective way so that we're all
Speaker:moving forward in the same
Speaker:direction.
Speaker:That I also like about it being
Speaker:called a puzzle is that it
Speaker:turns it into play and it
Speaker:removes some of the stress and
Speaker:I feel like right now
Speaker:there is just so much
Speaker:stress in the world.
Speaker:We have macro stress
Speaker:like is there going to be war in
Speaker:Europe?
Speaker:Is there going to be a war in
Speaker:Canada?
Speaker:The planet's still burning up but
Speaker:nobody cares about it right now
Speaker:because we have more pressing issues
Speaker:and so there's just this like of
Speaker:control sense of dread.
Speaker:And then you add AI.
Speaker:Which is a runaway technology.
Speaker:Nobody knows what's gonna happen to
Speaker:their jobs.
Speaker:We did the internet, and I think
Speaker:everybody's much more positive
Speaker:because we didn't realize what was
Speaker:gonna happen.
Speaker:And then social media, and now
Speaker:there's like more fear of AI,
Speaker:partially because of our previous
Speaker:experiences, partially because
Speaker:Terminator.
Speaker:With a backdrop of just everything
Speaker:is scary.
Speaker:And then what is not going to
Speaker:work in organizations right now.
Speaker:Is people are so afraid.
Speaker:It's very hard to then get
Speaker:inspired, find flow,
Speaker:play, open up your
Speaker:mind for creativity.
Speaker:And yet now is the time where we
Speaker:need to do it more than ever.
Speaker:And so how do we as leaders
Speaker:introduce and
Speaker:lighten things to
Speaker:actually get better results out of
Speaker:our people?
Speaker:And I feel like doing something like
Speaker:this and calling, and that's
Speaker:I think why I love it as a puzzle so
Speaker:much, is it just removes a
Speaker:layer of stress.
Speaker:And I know sometimes they're like,
Speaker:no, no, we need the stress to
Speaker:perform, but we have so much stress
Speaker:right now that we don't.
Speaker:We need play to perform.
Speaker:I so agree.
Speaker:With you. And I've tested this in
Speaker:workshops, in talks.
Speaker:I've tested with live audiences
Speaker:where I say, just think
Speaker:about the following two questions
Speaker:I'm going to ask you and tell me
Speaker:how you feel at the end of the two
Speaker:questions, at the end of each
Speaker:question.
Speaker:So just think about how you feel and
Speaker:the contrast. And I'm gonna ask you
Speaker:those two questions.
Speaker:What goals do you want
Speaker:to achieve for your company this
Speaker:year? And the second question is
Speaker:what puzzles do you want to solve
Speaker:for company this year.
Speaker:And the answers I get are vastly
Speaker:different.
Speaker:And I'd love your take on it.
Speaker:So I wasn't thinking about the
Speaker:actual goals, but
Speaker:when you said, what goals do you
Speaker:want to achieve? I get a bit of
Speaker:a hardness in my stomach,
Speaker:a deflating of my soul, and
Speaker:I'm like, oh, and it
Speaker:feels like really hard work.
Speaker:And then when you say, what puzzles
Speaker:do you wanna solve?
Speaker:Because I love puzzles so much, I'm,
Speaker:like, ooh, I physically lean
Speaker:forward, I have a lightness and
Speaker:a surge of energy.
Speaker:And it's like, yes, let me go and
Speaker:have some fun.
Speaker:And I really could feel those
Speaker:physical reactions to
Speaker:those words.
Speaker:There's one.
Speaker:I wanted to mention about AI because
Speaker:you brought that up.
Speaker:One of the big things that
Speaker:I see as dangerous, this combination
Speaker:of using AI and
Speaker:being so OKR driven,
Speaker:it's a super dangerous combination.
Speaker:Why do I say that?
Speaker:Because AI is going to be fantastic
Speaker:at optimizing for metrics, right?
Speaker:The better it gets at whether it's
Speaker:content creation, UX, coding,
Speaker:etc. It's going to be fantastic and
Speaker:optimizing for numbers, but it's
Speaker:not necessarily good for long-term
Speaker:business results.
Speaker:And one example that I want to give
Speaker:you is even without the use of AI,
Speaker:but now imagine AI
Speaker:used for this purpose.
Speaker:Let's think about dating apps.
Speaker:The entire dating industry
Speaker:has been in a slump.
Speaker:Why?
Speaker:Because dating apps optimize
Speaker:for user engagement.
Speaker:Tinder came out with swipe left,
Speaker:swipe right.
Speaker:Everyone copied it because user
Speaker:engagement was through the roof.
Speaker:And what that led to,
Speaker:It gamified intimacy,
Speaker:and it made human interactions more
Speaker:toxic. And the end result was
Speaker:people feeling dating fatigue,
Speaker:burnout, FOMO, deleting
Speaker:dating apps.
Speaker:And so...
Speaker:Optimizing for metrics didn't
Speaker:lead to long-term good results
Speaker:for the dating industry.
Speaker:Bumble last year laid off
Speaker:30% of all of its staff.
Speaker:And now imagine with AI, we can
Speaker:accelerate all of that
Speaker:hugely, optimize for all sorts
Speaker:of metrics, but we're not going to
Speaker:create neither better products nor
Speaker:better things for society.
Speaker:Want to ponder?
Speaker:I like it, then I
Speaker:guess it all boils down to watch
Speaker:out what you wish for because you
Speaker:might just get it.
Speaker:And so you get all, you focus on
Speaker:these metrics and they end up sowing
Speaker:the seeds of destruction.
Speaker:And which is why we need to think of
Speaker:puzzles instead, so that you're
Speaker:not just optimizing for metrics.
Speaker:Like the puzzle should have been,
Speaker:how do we make dating a
Speaker:really good experience for people
Speaker:while also monetizing?
Speaker:If our listeners can only take
Speaker:one thing away from
Speaker:today, what is it?
Speaker:As much as people say
Speaker:OKRs will work
Speaker:for you if you just do it right,
Speaker:that has never been my experience.
Speaker:There are fundamental issues with
Speaker:it.
Speaker:And what we need is a mindset shift
Speaker:from goal setting to
Speaker:one of puzzle setting and puzzle
Speaker:solving.
Speaker:And this example that I gave you of
Speaker:this maritime company I've been
Speaker:working with, sales had stalled
Speaker:in 2023.
Speaker:We used puzzle setting in puzzle
Speaker:solving, we doubled sales in 2024.
Speaker:Again in 2025.
Speaker:And we've reduced customer churn
Speaker:from 26% to 4%.
Speaker:You can drive real business
Speaker:results with puzzle setting,
Speaker:puzzle solving. You don't need goals
Speaker:for that.
Speaker:Radhika, thank you for joining us in
Speaker:the operations room.
Speaker:I love puzzles.
Speaker:I will rebrand my OKRs as a puzzle.
Speaker:I read your book. You have a book,
Speaker:don't you?
Speaker:Well, I'm working on my second book,
Speaker:actually, so it's going to be about
Speaker:why goals and OKRs don't work.
Speaker:But in the meanwhile, people can
Speaker:download the free toolkit and
Speaker:they can tell me about their
Speaker:experiences using this framework.
Speaker:And so feel free to reach out to me
Speaker:on LinkedIn to share those
Speaker:experiences.
Speaker:And it might just make it into the
Speaker:book as a case study.
Speaker:Love it. Radhika, thank you so much.
Speaker:If you like what you hear, please
Speaker:subscribe or leave us a message and
Speaker:we will see you next week.
