It’s always good for startups of all stages to have goals and be working every
day in pursuit of those goals. However, too many startups lose sight of those
goals and the practices that can help get them there. That’s the precise problem
that founder and CEO Matt Tucker is looking to address with his startup Koan, an
alignment platform that’s heavily inspired by OKRs.
In the latest edition of the Silicon Valley Momentum Podcast, Roland Siebelink
spoke with Matt. The two discussed a wide array of topics related to Koan and
the qualities that put startups in a position to be successful:
- How Koan is solving a “structured collaboration problem” by helping teams work together and work
transparently to create a common purpose across the entire company.
- Why several small but positive behaviors can end up making a significant difference in the end.
- The importance of startup leaders “doing the basics,” even when a business is in its infancy.
- How a combination of coaching and software can be the right combination for creating lasting change
within a startup.
- Why leaders need to take into account the problem they’re solving and how quickly they need to scale
when it comes to fundraising.
Roland Siebelink: Hello and welcome to the Silicon Valley Momentum Podcast.
My name is Roland Siebelink, and I'm a Scaleup-ally for tech founders. And I'm
so excited today because with us is Matt Tucker of Koan.
Matt Tucker: Thanks so much Roland for having me.
Roland Siebelink: Absolutely. I'm so delighted to have you on because Koan
is a performance platform, really focused, as I understand it on OKRs. There's
so much to talk about OKRs in the startup world. Did I have that, right?
Matt Tucker: Yeah, you did. I'm looking forward to the chat. We think about
the problem that we're solving more broadly, as this problem of alignment. Down
to the individual team, how do we work more transparently together? How do we
know what's happening? How do we define the outcomes that we want to achieve?
Whether that's through OKR or another methodology. And then how do you scale
that up? How do you get teams to work together? How do you create common purpose
across the entire company? And this is a set of things that have been stuck in
very manual processes for a long time. And we're trying to finally bring the
advantage that software can to helping every team do these behaviors better.
Roland Siebelink: I'll definitely want to delve into that quite deeply
because the startups I work with, implementing OKRs and/or other performance
systems is often a core part of what we do and a source of a lot of insecurity
with startup leaders, I would say. But before we delve into that, Matt, can you
tell me a little bit about your history? You have a good history in the startup
world already, you were saying, right?
Matt Tucker: I graduated with a computer science degree way back in 2000.
And almost immediately, in the middle of the dot-com boom, I did first start up,
which was Jive software. We bootstrapped Jive for actually six years before
doing our Series A fundraising. And Jive, if you're not familiar, was an early
pioneer in collaboration software and in the right place at the right time.
Facebook was happening, and Twitter, and MySpace.
And our mission at Jive became, let's take all that innovation that is changing
our consumer lives and apply it to some really interesting business use cases.
You had the crazy up and to the right for many years. Series A and B and C. We
IPOed in 2011. And we'll get into it. There were some harder years for Jive as
well. But then finally decided it was time to do the next startup. And I got
really fired up about the problem that we're tackling at Koan, which I consider
a structured collaboration problem. And so we've been at it at Koan for the past
Roland Siebelink: That's awesome. Before we go into Koan, many people who've
had that huge startup success who made it, if you will, who've established
themselves in Silicon Valley would rather become an investor or become their own
VC or join a VC firm. Is that something that you can shed some light on? What
was your decision process in this evolution in moving out of Jive and looking
for your next thing?
Matt Tucker: A great question. I think in all of our own careers, we have to
look for what are our own dopamine triggers and what makes us happy, what gets
us fired up and excited to wake up in the morning and work on new things. And
there's probably many moments in each of our careers where we have a little bit
of an existential crisis, like, "What do I wanna do?" Especially if I have a lot
of options about what that can be and we're lucky enough to be in that position.
And it just became very clear to me. I love building stuff. And there are great
things about the early stage of a company and in the middle and later stage. But
just got excited about the idea of going and doing it all again. Building
something from the ground up, and that aligns much better with my own dopamine
triggers versus what was also an amazing thing, helping other startups,
investing. I can understand the allure there, but building things is what I love
Roland Siebelink: Let's go into the details of Koan a little bit more. You
just called it a structured collaboration more so I think than in your
experience with Jive, right? Can you delve into that a little bit? What is the
evolution from just general enterprise communication toward a more structured
collaboration working toward alignment, as you said.
Matt Tucker: Yeah. Taking this problem of alignment. Generally speaking, as
a strategic and operational cadence that you want to get set up in every
company, whether you're a tiny startup or you're trying to scale really quickly,
or you're a large enterprise. And that cadence has some aspects that are
multi-year. How do we write down our mission and our vision and be clear about
our values and define the strategy? And ideally, at least a year, if not a
multi-year strategy. And then that cadence starts working down into "All right,
how do we set goals every quarter?" We define the outcomes that we want to
Even more than that: "How do we put together the plan?" What are we going to
achieve this month toward our goals? And then even down to the, "Well, what
happened this week?" Let's reflect on it. What did we achieve? Did we do as much
as we wanted to? What should our priorities be? And then even down to every day.
What am I working on? Where am I blocked? And where do I need help?
And I think it turns out if you think about that cadence and you build some
great behaviors around how to do all of those things and don't just leave it up
to chance, you have a much better chance at success as a team and as a company.
And I call it a structured collaboration problem in the sense of there's an
actual rhythm around it. And there's some real processes you need to be
thoughtful about how you do each of it.
Whether you use a software tool like Koan or you're trying to do it totally
manually. And it's not just, "Hey, we're chatting in Slack and I posted a
message.” It's, "Oh, we've decided how to synchronize as a team of humans."
There's a drum beat and the drum beat is how we're running our team or our
company. And that is an incredibly important problem to think about all the way
down to the daily cadence. And then up through the "Why are we even here?" And
how are we thinking about the problems we're trying to solve on a multi-year
Roland Siebelink: I love that you really positioned this as ultimately a
methodology of practice. You even said, whether you use software such as Koan or
you do everything manually is almost a secondary question. It's a contrast with
how I see startups try to decide the tool first and then almost think of the
processes and the habits as an afterthought. Is that a problem that really
plagues this space, would you say?
Matt Tucker: I think you're right to point that out. If you are lucky enough
to start with the tool and then accidentally figure out that the cadence and the
practices, maybe you can get lucky. But you're right. The thing that actually
matters is having those positive habits. One of the foundational philosophies of
Koan as a company is our belief that small, positive behaviors, if done
repeatedly, lead to massive results.
And this is something that great athletes know well. If you chat with an
Olympian, for example, and they're generally not really focused on, "I have to
think so much and so hard about what I'm going to do when I'm trying to win the
gold medal on the race day." And what they're really focused on is, "What's the
practice that I know that I need to put in every single day." And if I do those
behaviors, if I put in the time, if I'm thoughtful about that cadence and those
behaviors, then everything's going to happen and it's going to add up to the big
impact that I want.
I think you're completely right. It should be about the behaviors. It should be
about those rituals, not about the tool. On the other hand, our hope and our
belief is that if you have the right tool, it can make the behaviors much
And there is this important moment, and typically quarterly for a lot of
companies, where you come together, you do this planning exercise, you agree on
what the big strategic things you want to achieve are. But that's not it. There
was this really bad problem, which is you set the goals and then nobody talks
about them again until the next quarter.
Roland Siebelink: It's too painful to do so, right?
Matt Tucker: Yeah. You just don't achieve them. It may sound, I don't know
if it sounds crazy, I hope it doesn't, but you should be chatting about your
goals every single week. And they're not that many weeks in a quarter. Twelve,
typically, somewhere around there. You should be making close to 8%-ish progress
every week. If you think about how short of a period of time. This is not like,
"Oh, we think about our goals once per month or even twice per quarter." There
should actually be some tangible progress and conversation around what we're
doing and what we can knock down over the next week as a team, every single
Roland Siebelink: We said already we want to delve a little bit into the
best practices for OKRs and alignment in the company. But I'd like to start this
discussion by pointing to your use of agile as an analogy. And I feel that
sometimes both agile and OKR have taken on some aspects of what you might almost
call a religion where people want to be the true believers and if they do it
exactly right then salvation will come to them. Is that how you look at OKRs as
well? Or is this more of a saying that people who haven't really gotten the
experience with OKR so much?
Matt Tucker: You might call that a leading question. But as you might guess,
my answer is no. We're not particularly religious about this. And maybe there's
a danger with anything that you turn into an acronym. It just automatically
turns into this heavy thing where people assume there's one and only one way to
do the process.
And ironically, you go read "Measure What Matters" by John Doerr or many of the
other great resources out there about OKRs. And the real emphasis is this is
meant to be lightweight. This is meant to create focus. And yet somehow, for
every organization and team that's had an amazing experience with objectives and
key results and where it's actually created more autonomy because we can focus
not on micromanagement but on defining the impact we want to have and then
letting people be creative about how they achieve it.
For all the good stories, there's just as many bad stories like, "Oh my God, we
came in, we did OKRs, we set all these goals. It just was this huge waste of
time." And I think there's always that danger of any business process. I think
you're right to point it out on agile. But one of the reasons we do love OKRs
much like agile is at their core, in a part of the philosophy of this process is
that it's meant to be lightweight. It's meant to be flexible. It's supposed to
adapt to the culture of your team. And it's obvious, in a sense of, "Yeah, there
are a set of principles that make sense for how you would set goals as a team."
It's what OKRs is about. This isn't like some weird, extra fancy stuff.
And same with agile. It's like, "Oh, that's kind of obvious." And once I read
about this, we should be able to do these practices in a way that's better than
the old waterfall way we're doing it. And so that's where we're always trying to
find with OKRs. Keep it lightweight.
Roland Siebelink: Go back to the first principles rather than try to follow
all the books and almost the Bibles these days to the letter. Listen more to the
origins than to the priests, perhaps.
Matt Tucker: Yeah. And I think this is that this is a challenge. One of the
things that we find with OKRs, in particular, is there has to be this journey
where maybe we weren't writing down our goals at all before. And there was
always some way that you're prioritizing the work that you're trying to achieve.
You get really excited about the idea. You'd be going to implement it, you may
have this assumption like, "Oh, we have to do almost a binary switch from the
old way to the new way." And everything must be this new way of how we're
Roland Siebelink: And then everything will be perfect, right?
Matt Tucker: Exactly. It's going to be perfect. All the messiness of our
startup will go away and everyone will know exactly what to work on at every
moment. And none of that's really true. And even as some of these ideas of how
you find mastery eventually in a martial art, right? You learn all the movements
and you do the disciplines. Practice again and again. And then eventually, when
you build actual mastery, you get more creative with it and you figure out how
to improvise. That's always what we help folks get to. And not to take it too
seriously in the interim. Making sure that it's actually providing value.
Roland Siebelink: In the pre-conversation, you also mentioned that you've
collected some, could I call them bad practices around OKRs that you're working
on? Is that something that you want us to start sharing with our audience
Matt Tucker: : We have, unfortunately, we've seen it all. And in fact, we
are in the midst of publishing what we call the anti-OKR pledge.
Roland Siebelink: That sounds fascinating. Tell me more.
Matt Tucker: I'll put "anti" in quotes. But there are a set of things that
people tend to do again and again around OKRs that make it not the lightweight,
focusing business practice but the heavy, really painful, "I'm doing way more
work than the value I'm getting out."
And so, we've collected it into a set of principles and we're launching it at
okrpledge.com. Please go take the pledge and maybe share it inside of your team
and your company if you're, unfortunately, working at an organization that is
maybe not doing their goals process in the best of ways. And the idea is that
it's a set of principles around, what does this look like when it's being done
well? This is not just for executives and this is gotta be something that
provides value all the way down to every individual.
Set less, focus more. And there's this really bad practice of companies setting
way too many goals. Plus, assuming that every part of the business needs goals.
And that's just not the case. And I really liked the analogy of OKRs acting as a
spotlight in your organization. In a sense of, "All right, we should set goals
around the smallest number of things that we want to dramatically change."
Everything else probably does not need OKRs. Manage that through business as
usual health metrics, KPIs. Not everybody needs to be working on OKRs every
quarter, for example. The less things you're focusing on, the more things you'll
There's a few other principles in there. This idea of resisting cascading goals.
Cascading is almost a bad word inside of Koan. We much prefer the idea of
bottom-up alignment. And we're also huge fans of not doing individual OKRs. We
encourage you to "just say no" to individual OKRs.
Roland Siebelink: Okay. Just team OKRs. But in every battle, right?
Matt Tucker: Exactly. Keep it a team sport. As soon as you're doing
individual OKRs, that almost by its nature acts against the interest of, "Hey,
this is actually just a small set of things we're focusing on." It almost always
means you have way too heavy of a process and get away from the spirit of
stretch goals and put people into fear-brain around, "This is how I'm getting
evaluated," or getting my promotion or getting my bonus and all those things act
against the better outcomes you can achieve out of a OKRs process.
Roland Siebelink: What I've noticed in the performance management slash
alignment slash OKR space is that we do have a lot of software companies. And
then very often you'll see them build a sizable professional services operation
to help companies implement the software to provide coaches, to provide customer
success in a broad way.
What's your philosophy about that in a relatively complicated space for
startups, such as performance management? Is the application/software of the
advice/coaching that provides the value? Do you need to have both or can you
outsource some of it? What's your feel about that?
Matt Tucker: Great question. By the way, I'm a huge fan of executive coaches
for every executive, especially if you're a CEO. If you don't have an executive
coach, you should go find one. It's going to lead to a much better result for
both you and your career, as well as for your company, whether you're a startup
or later stage. And our perspective is this is not a problem that can be purely
solved by software. This is also a problem that can not purely be solved through
consulting. This is, I think, part of where things have gone wrong. And there's
been many, many years of management consulting, it has led to a big impact. It's
necessary. People need help figuring out how to do this stuff. But the part
that's been missing is lasting behavioral change.
I've been through enough of these in various past iterations. We'd have a
consultant come in; they'd be extremely helpful. Felt like I learned a whole
bunch of stuff. And then we'd go back to the day job and forget it all almost
immediately. This is where we think software plus expertise can actually lead to
the most profound impact, which is the expertise, the coaching, the consulting,
that provides the context, it provides the overall methodology and, some
awareness of what we're doing.
And then the software is there to help you do that, the practice and the
positive behavior, the habits. Our philosophy at Koan is, we're trying to be the
software piece. We care a lot about these topics. We do lots of blogging and try
to participate in podcasts like this. But our whole model is we're going to go
partner with all the experts out there like yourself. That's what we're trying
to do. And so we don't have a professional services arm at Koan. It's not that
that's a terrible model. It's just, we think we can have a better impact by
focusing on the part that we really want to be the best in the world at, which
is the software part of this.
Roland Siebelink: Can you tell us a little bit where are you at with Koan at
the moment? How big is your team? How fast are you growing? And what's next?
Matt Tucker: Yeah. We're a seed-stage company. We've been at this a couple
of years. I have some amazing investors. One of the reasons, frankly, that OKRs
are important to us, and even though we're not religious about them, there are
other great goals, frameworks. One of the really interesting things happening
out there is there is a big movement to embrace this methodology as part of how
you run a company well. That's part of what's been leading to a pretty huge
amount of growth for Koan and what we think is becoming a bit of eventually a
category around alignment.
It's not going to be all about OKRs. That is not a thing all by itself. But it's
part of the story about how you create a great operational and strategic
cadence. We think that there should be purpose-built software for this. It's
different from task management. It's very different than HR performance
management. There has to be something that connects different work streams
together so that inside of a team you work better together. And then how do
teams of teams know what one another are working on and become more outcome
It's our belief that over time, this is going to become a lasting software
category. That's what we're trying to build towards. OKRs are a big component of
that, especially right now. And for all the organizations out there trying to
figure out, "All right, well, how do we do goals better?" Now that we're remote,
we need to be more outcome-focused and not try to micromanage people but figure
out how to do these positive behaviors.
For all those organizations out there trying to figure out how to adopt some of
these methodologies in a lightweight way, in an employee-friendly way, we hope
you will check out Koan. Plus, go and sign up for the OKR pledge at
Roland Siebelink: Okay. For everyone who is interested in adopting or
improving their OKR methodology, their alignment methods, and wants to stick to
this lightweight principle, it sounds like Koan is the way to go. And please
sign the OKR pledge at okrpledge.com. Matthew, last raised funding I think
around a year ago, is that right? Is this a big journey that you're on to keep
going the series A-B-C routes like you did at Jive? Or is this still open for
Matt Tucker: We're definitely doing the more traditional approach of raising
venture rounds in order to scale quickly. And part of what you have to ask
yourself as an entrepreneur is, what is the nature of the problem that I'm
solving? Is this one where you need to scale quickly and where the category is
going to evolve quickly. And if so, that makes it a good and ventured scale type
I'm pretty sure that's the problem, the type of problem that we're tackling. And
the reason that we've done funding rounds to grow more quickly. We'll next do a
Series A. And then there are a lot of other problems that maybe earlier on and
where maybe at some point they will be a venture scale where you need to
accelerate the growth. I'm sure we could have a whole other conversation like
raising money is not its own goal in and of itself. Not every company needs to.
There are many different paths. But that is the path we're on at Koan.
Roland Siebelink: Yeah. And any investors that want to be in contact with
Matt, of course, you have a very solid network of your own. But if you need an
introduction, you can always ask me and I'm happy to provide.
Any last thing you want to leave people with other than signing the OKR pledge
and checking out Koan, Matt, as something for them to help you with or something
Matt Tucker: Maybe just a final thought back to that idea of don't forget
the basics. Even if you're a startup, I think this is often a question of "I'm a
startup, things like OKRs, things like writing down our mission and vision, it
sounds so big company." We'll think about that stuff later. We're just trying to
build our MVP and ship something and get it out there.
And I am a huge proponent of not doing that. You got to scale it down. You have
to make it appropriate, even for an early stage startup. But it turns out if
you, from the very earliest moments, start building that positive practice and
intention, and the muscle strength around that great strategic and operational
cadence, you're going to have better results.
Even if you're at the beginning, don't assume this stuff isn't for you. Don't go
make it complicated. Keep it simple. But do those basics and you will win that
gold medal at some point.
Roland Siebelink: Excellent. Well, it was great to have you on,
Matt Tucker: , co founder and CEO of Koan, an alignments platform inspired
around OKR methodology and others.
Please go check it out on Koan.co and also sign Matt's OKRpledge.com. Thank you,
Matt, so much for joining. This was amazing. And yes, we are looking forward to
seeing the results come in at Koan as well.
Matt Tucker: : Thanks so much, Roland, for having me.
Roland Siebelink: Thank you.
Roland Siebelink talks all things tech startup and bring you interviews with tech cofounders
across the world.