Onboarding Therapy

In this episode of Onboarding Therapy, Kim and Shareil welcome their first guest, onboarding expert and author Ramli John. Together, they dive into the nuances of friction in onboarding and how internal misalignment often becomes the root cause of a disjointed customer experience.

Highlights include:

Why internal misalignment on onboarding goals and ownership creates friction for customers.
Common gaps in onboarding programs, including selfish tasks and fragmented responsibilities.
How to identify and address points of friction in your onboarding process using data and customer feedback.
The importance of providing multiple learning pathways to cater to diverse customer needs.
Actionable strategies for building internal collaboration and creating a seamless onboarding experience.

Ramli, Kim, and Shareil share real-world examples and practical advice for reducing friction—starting with your internal processes—to create better outcomes for your customers and teams alike.

👉 Subscribe to hear more insights on customer onboarding and practical strategies to improve your onboarding programs.

What is Onboarding Therapy?

Customer onboarding in B2B SaaS is changing fast, but the resources for onboarding teams? Not so much. That's why we're kicking off Onboarding Therapy, a podcast that tackles the real challenges onboarding teams face every day.

Ramli: I was like, oh, Ram,
you wrote the book on product

and onboarding, but I actually.

Don't suggest people start there
because you can actually learn a lot

from how and where you're losing them.

You can see their eyes glazing
over and they're like looking back.

It's whoa, this is a lot

Welcome to onboarding therapy.

And this episode, Cheryl and I are joined
by an amazing guest Randy, John . Rarely

literally wrote the book on onboarding.

So we are excited to dive into the
topic of reducing onboarding friction.

And the aspect of friction, we ended
up focused on, surprised us all.

Let's get into it.

Kim: This is the first time that we have
a guest, not from arrows on the show.

So we're really excited.

We've known Ramly for a
long time, many years.

And I think Cheryl has known
Ramly from the onboarding

world even longer than that.

So super excited to get your insights and
would love if you want to start with a

quick kind of intro and your background.

Ramli: Yeah, I, my name is Renly John.

some people also call mE
RJ, founder of DelightPath.

I was formerly working at AppCuse
and wrote the best selling book,

Product Led Onboarding, been working
on onboarding for many years now.

And really it's my jam.

I love talking about it.

So thank you for the
invite to join your show.

Kim: Yeah, of course.

Before we jump into kind of the main topic
I would be curious to hear how you got

started in onboarding, especially because
I feel like it's such a new thing still.

So I think it's always interesting when
people have been in it for a while.

Ramli: Yeah, I got into
it as a growth consultant.

I was working with some SaaS companies.

This is like seven, eight years ago.

And I was tasked to bring on signups.

And through my curiosity, I wondered
if the signups I was bringing

in was actually sticking around
and I found out they weren't.

And that lit a fire in me.

This feels wrong.

It feels absolutely wrong
that, Hey, they're happy.

I'm bringing signups, but they're
actually not sticking around.

I got into the whole searching
and finding content around it.

I, that's how I came across Westbush.

That's something with product led growth.

But before that, he was talking a lot
about onboarding because he found that's

the entry point to product led growth
or the beachhead is like people talking

about Oh, how do I improve my experience?

Onboarding got through that.

So I ended up working together on multiple
companies mixed panel and, a product

with Microsoft and different companies.

And I, we, I ended up codifying our
process into product led onboarding.

It's been my onboarding journey.

Awesome.

Kim: Cool.

Let's kick it off.

Today we're going to talk about kind
of friction in the onboarding process.

I think specifically from the customer
or users perspective and things that

they're typically running up against.

And then hopefully we can get into kind
of ways that teams solve for that too.

Shareil: Happy to jump in on that one.

So frictions are all over the place, and
I think there's in my mind, two severe

impacts when there is a lot of friction.

The first one is bad internal process,
just generally butting heads, running

into challenges internally, running
into disagreements internally,

which that stuff is solvable.

But if that hangs out too
long, now it's the customer

experience that really suffers.

And that's why we hear things like we
have a churn problem at day 30 and we

have a retention problem at month six.

It's oftentimes that internal friction
of understanding what even is onboarding.

What should the metrics be?

What should we be working towards
that if not resolved turns

into some of that friction.

And then, yeah the impact is unfortunately
churn and a bad customer experience.

Ramli: Yeah, I think that you
really hit the nail there.

I've never thought about it.

There's that internal friction
to onboarding where it's not

the friction in the experience
itself, but it's like not aligned.

They're not aligned on Hey what is
onboarding like you mentioned, but what

is success for our customers and users,
and, funny enough, I've talked to quite

a few teams recently, the past few weeks,
And they're often like, who owns it?

First of all, who owns it?

Like who owns, it's so
many different places.

But the other thing is I'm finding one
pieces of it's owned by certain functions

and they don't talk to each other.

Like marketing owns, onboarding
emails and then customer success, a

customer onboarding owns the one to
one and the product owns in product

and they don't talk to each other.

That's such a big.

Challenge that results
in fractured experience.

The worst one is when there
actually is nobody owning anything.

And when that happens, like
that is even worse experience.

And I think that's often to your
point, Cheryl, like that's a root

cause of friction, bad friction is.

Misalignment and the team's not working
together to create that really smooth,

seamless experience rather than, Hey
let's actually work together this rather

than they, you do your thing and I do
my thing and we'll figure it out after.

Shareil: Yeah, one one other negative
output of that kind of environment too,

is often what happened, Kim and I were.

Talking about this recently, often
what happens is then those teams,

let's start with the onboarding team.

They themselves don't really
understand their metrics or

what they're working towards.

So now you're just heads down
doing your day job, doing calls,

trying to get customers onboarded.

And.

A few months go by or a few years go
by and you look up and now it's like

this thing has been labeled as a cost
center and we don't know what the value

is and now there's even less desire
to collaborate internally because we

haven't proven value we haven't proven
what we're working on or what we're

working towards so now you're also
burning out team members potentially and

causing more of that internal Friction
because there is no collaboration.

And then again, all of this just
keeps trickling back to a worse and

worse customer experience because.

Customers don't care, nor
should they care, what you

are doing behind the scenes.

It's not their problem to figure out
you have bad handoffs, or you have CRM

fields that are missing properties.

I don't care about that when
I'm talking to my vendors.

I just want to know what to do and how
to go do it and when I need to do it by.

And if you can't convey that to me, That's
the first point of friction externally.

And then again, if internally, you
don't know how to solve for that.

If I came to you and
said, Hey, what's next?

And you're like, I don't know.

My checklist says to talk to
you about these two things.

And that's my job because you're not
getting guidance or you're not getting

support or you're not getting alignment
on the bigger business metrics.

It can spiral pretty
quickly into a bad recipe.

Ramli: That's a really good point.

Like the misalignment in
metrics, misalignment in success.

And even in that checklist, misalignment
in steps, like this is something that,

what should be in the minimum steps
that you, your customer should do.

I find that often the, what's shown we
don't this is something that happened at

AppCuse as well, where, marketing on this
product on that, and I got a chance to

get those different teams together and
Hey, What is our ideal journey look like?

And if that's the case, what are the
ideal steps so that when you have

a checklist, what's shown on the
screen in the end product and what's

written in the email and what customer
onboarding team is saying one on one.

It all aligns and that's so much better
when like the whole boat is rowing in

the right same direction or the ideal
success state for your new customer,

the ideal metrics you're actually
working towards the same metric.

And also you're all you're all
aligned on what is the steps our

customers need to do to get there?

Because if you don't have that
alignment, then you're, you might be

like rowing all in different directions
and end up in different places.

Kim: I feel like a big thing too, is that
the, I think it's really interesting.

I didn't expect it to take this turn
about the friction actually being all

internal, but I think it's so true.

And I think a big piece of it too, is even
if you do have alignment, I think a lot of

teams design their process based on what
their internal teams need to have done.

So they're creating steps
in their processing.

We need the customer to activate on these.

Three things or whatever it is,
because that's what we've determined

to be success, but that's not what the
customer is determining to be success.

That's not what the customer values.

And so I think that's a huge issue
too, is people have a well designed,

thought out plan that maybe has
some kind of internal alignment.

But if you're not thinking of what.

Is actually valuable to the customer.

What is actually going to have our
customer not just activate on the

product, but actually see success
and be better at their jobs because

they're activating on our product.

I think that's, what's missing
from even the teams with the best

communication and collaboration.

Shareil: I could give you a hug right now.

I've been preaching.

I've been preaching this for
a while with new customers.

I obviously at arrows, we get to
talk to customers working on their

onboarding plans and onboarding
products and onboarding processes.

So I get to selfishly see a lot of that.

And I've been jokingly, but not
really jokingly calling people out

on what I call selfish tasks, which
is exactly what you just described.

And we all have them.

I have a bunch of selfish tasks.

I want people to send
arrows onboarding plans out.

That's my main goal, right?

But when and where you present those
selfish tasks can also then be a gap in

the process or where people get hung up.

And to Kim's point, if, and most commonly
those selfish tasks don't tend to align to

the customer's goals or customer's pains.

That's another point of friction now.

And so all of these little things
can really compound quickly.

And now customers are stuck.

That's what the end result looks like.

They're stuck in the process.

If you don't have that internal alignment
or internal collaboration, it's often

hard to get them unstuck in that process.

And then if you're not involved
in some way or fashion.

You also don't really know how
to optimize that going forward.

So now you have created this expensive
function inside of your business that

is not actually driving revenue or
even retaining revenue for that matter.

And of course, it's going to be
labeled a cost center and you're not

going to get resources and support.

But it's that, if you remember Ramli when
I was back at Sprout social and you were

at PLG, we talked about onboarding guilds
and that's what we had set up at Sprout.

Yeah, I

Ramli: like that.

Shareil: Where it's sole purpose was
to build collaboration internally.

And it didn't start on day one.

We had a one to one on.

We then developed it a little bit
more into strategic webinars that

could reach more folks than we were
like, oh, there's something here.

Let's build upon this in the
product and get activation.

But one thing you also said earlier is
incredibly important is that all those

pathways have to lead to the same.

End result.

And they're not all going to
get there in the same way.

There's no world where a quick
in app tour is going to replicate

5 1 to 1 human phone calls.

That's not the intent, but the end state
should reflect a similar thing that

type that takes that customer from start
point to that 1st value realization

moment of the 2nd 1 and beyond.

And if you can align all those
pathways, Then you have a shot at,

and if you remember, we used to
talk about like a hundred percent

Ramli: onboarding.

Shareil: That's a vanity metric.

There's no such thing.

There is no world where every
one of your customers is going

to be onboarded the same way.

Yeah.

We're talking about adults.

We're talking about human learning.

We're talking about psychology.

Everyone operates a
little bit differently.

So if your goal is to onboard 100 percent
of your customers, I'll be the first to

tell you it's not going to happen, but
if you can provide pathways and options

for 100 percent of your customers to
have a chance at being onboarded and

lean into where people learn differently,
and some folks will want to do one call

and then do a few self guided recorded
webinars and maybe jump into the

product and click around and see a few.

Modules pop up that guide them, those
pathways all leading customers to that

general end state is how you build
a holistic onboarding program that

does get buy in and drive results.

Ramli: Yeah.

And it's really about that.

I want to double click on what
you said there that is about that

really catering to how people learn.

Like people learn in different ways.

I like to ask this question to
folks where Ikea is this big store

where it's a furniture store,
but like they have, it's a maze.

You can get lost in there.

And I like to ask people like, Hey,
do you shop by following the pathway?

There's like a certain route
that's arrows on the ground.

Or do you shop?

Or I do you know what you want?

I need a desk.

I go there directly.

I get out like within five minutes, right?

Which is almost, they try
to make it impossible.

Or do you, just jump around and people
have different answers to that when I

asked him that question and it's imagine
if Ikea like forced you that you must

follow this path or else you cannot shop.

But people would be upset and I think
it's the same way here where you're

giving people the option based on how they
prefer to learn, and if they want to learn

through one on one, give them that option.

And if they want to learn through a
webinar or through a workshop with

your team, give them that option.

And if you want, if they want to
learn through just getting in there

and just getting going, give them
that option and making it easy.

And that's really the whole, we're talking
about friction, but like the friction of

just giving them just this one path of
learning this pathway, like you mentioned,

often limits how many people you can
onboard, because there is value in one to

one and one to many and also in product.

If they all work together, that's great.

And giving the people the different
options based on their learning

style is like super, super powerful.

Most advanced b2b companies like
what you guys were doing on board and

gill that sprouts social and learning
pathways That's what like the best

in class product like companies are
doing like slack and HubSpot They're

giving people the option on how they
want to learn rather than one way

Shareil: Yeah.

And in your analogy that you just
used there, I love that IKEA analogy.

The most important piece you said
was my goal was to get a desk.

So if your goal is only to go
in there and get a desk, I don't

need the 1500 yellow arrows on the
ground, taking me all over the store.

But if my goal is in there and I've
done this as a team event, actually in

the past to do the scavenger hunt at
IKEA, then cool, let's go zip through

all the aisles and go through all the
arrows and explore the whole thing.

But the point is both options are there.

And IKEA.

Somewhat does this too.

You can weave your way through
certain aisles and end up in

other areas or other departments.

But it's about those
options to that end state.

The most important is the goal, right?

What is the customer
actually trying to get to?

That's how you can avoid
some of those selfish tasks.

And I don't get me wrong.

I have plenty of selfish
tasks in every process I have.

We all have needs.

We all have our own goals.

We all have metrics.

That shouldn't be the first thing
you put in front of a customer.

Give them some value first.

Let them solve one of
their problems first.

Let them feel like, ah, this pain's
gonna be a tiny bit easier if I do this.

That momentum builds, then sure, let's
sprinkle on some of our own selfish

tasks and upgrades and all that.

Because I also do think that's important.

That's how you turn
onboarding into a revenue.

Generating center as well by
presenting opportunities by helping

customers see the value of cells
and upgrades and premium features.

You have, that's all great.

We shouldn't be focused on that.

They just shouldn't be
the things we lead with.

If they're not helping customers
with their problems and goals.

Kim: So I'm imagining most people
that are watching are in some

way involved in onboarding.

That probably has a lot of friction.

Even Rambly, you were saying Cheryl was
running best in class onboarding program

previously, but there's still friction.

Your customers are still feeling
friction and your internal teams are

still feeling friction, even in a
super, super well designed environment.

Really well thought out.

Lots of resources kind of program.

What are the steps that you would
recommend taking to start evaluating?

Where are those friction points?

You're not going to solve every
single friction point, but where are

the places that you would start or
recommend a team starting to look and.

Try to figure out how they can
reduce some of that friction.

Ramli: think a best place to start is
just, first of all, I think hearing

this is the reason why I love, like if
I had to do a startup from scratch, I

would actually onboard them one on one
because you can hear the pain I was

like, oh, Ram, you wrote the book on
product and onboarding, but I actually.

Don't suggest people start there because
you can actually learn a lot from how and

where they're losing, you're losing them.

They're, you can see their eyes glazing
over and they're like looking back.

It's whoa, this is a lot like
that's great qualitative feedback.

That's saying that, hey, this person.

Point here is overwhelming and
confusing and they're getting

lost and they're not understanding
the to Cheryl's point earlier.

They're not understanding the
value and the why and what's

in it for me in that point.

And if it needs to be said one on
one, then Oh, that's an interesting

place to start as it scales.

Like definitely there's some
tools, like a more internal tools

specifically for self serve full
story that can, you can watch people.

They call it reach clicking, like they're
clicking the thing over and over again.

They have some analysis around that.

And there's, you can also take a look
at like drop off points in the journey.

When you have.

A data, like all the steps are laid out
and a lot of your users are not doing

this, or a lot of the customers are not
doing specifically a certain step of it.

Then that's an interesting place
where, why are they not doing that?

Is there a struggle or is there a pain
that, that they're not understanding

in that specific area there?

Shareil: Yeah.

And to add to that, I
would I love all that.

Especially the bit about not
starting with product lead.

And I'm not saying don't
start with product led.

I'm saying it's easier to do product
led if you have a little bit of

intel from one to one onboarding.

And that doesn't also mean you have
to have a dedicated team where you're

spending money hiring a bunch of people.

That could be the founder talking
to customers and just jotting down

bits and, building off of that.

But a couple things to add.

I think one approach it, especially at
first as a one size fits most model, no

matter what pathway you're going down,
because you're never going to solve

for everyone's needs and everyone's
pains in any one pathway at any one

time, inevitably people will get stuck.

And I think that's where data becomes
really important and collaboration again.

So knowing where customers are stuck
is the first key to unlocking them

and helping them and growing them.

So at arrows, Kim and I always talk
about onboarding never ends and always

be optimizing your onboarding programs.

And fundamentally we mean those things,
but we also don't mean sit and spend

months at a time trying to craft this
perfect template or perfect process.

Because.

You're guaranteed to waste
time and money doing that.

And then you're still not going
to actually make progress or

learn what is or isn't working.

And instead start using plans,
spreadsheets, emails, whatever it

is you're putting out into the world
and learn from that, if 95 percent

of your customers get stuck on
the same task, that is a bad task.

Let's figure out what is
going on in that task.

And oftentimes that.

Actually is tied back to
some of that selfishness.

We tend to jam a lot of selfish
things inside of these tasks and then

they become really big and really
complex and really hard to achieve.

And now you have two problems.

Customers are stuck in that
almost certainly, and you don't

know what part you're stuck on.

So now you're doing the generic.

Hey Ramli, it's been three weeks, man.

Haven't heard from you.

What are you up to over there?

Whereas if I knew exactly where
you were stuck, I could reach

out and say, Hey, are you having
trouble scheduling time with me?

Cause you're in a different time zone.

Here's a different calendar.

Let's keep this process moving.

So the more of those moments of, and
this is where I think it is external

friction, where customers get stuck,
that is tied to you solving for that.

Having honest conversations
internally of, is this a sales

problem or sales expectations misset?

Is this a product problem?

Is the design not as intuitive
as we thought it was?

Is this an onboarding
and a success problem?

Because we're not delivering the
right value or the right training

at the right time in that process.

And enough of those moments.

And that is where that internal
collaboration becomes important.

Actually help solve for that, because
then you can proactively address

if the customers are getting stuck
on the same missed that expectation

every time it's a sales challenge.

Let's figure out what's happening there.

What's being communicated if those
sales reps are saying the right things.

It's a marketing challenge.

What are we marketing on our websites
and on our marketing pages that are

leading customers to think that onboarding
process or call or whatever it is.

They're thinking, ah, this is
very different than what I was

just marketed to or sold on.

And then the other kind of big challenge
I see often is, and we're all somewhat

guilty of this, especially in SAS, is
that we highlight that this thing is

going to be easy to set up and fast
to get going on and quick to deploy,

and it's going to change your life
and revolutionize your business.

Then you get to onboarding and
it's a three month process and 150

tasks and 20 calls set up for you
and all sorts of back and forth.

So that is again, internal misalignment.

So it is better to start with something
to Kim's main question, start on a

process, figure out where customers
are getting stuck, unpack that,

and then keep going and keep going.

And enough of that then lets you
confidently sit and say, Hey, I'm

Hey, design team, we need this.

Hey, CS leader, we need you to
stop saying this and onboarding.

Cause it's not true.

Hey, sales, stop talking about this
feature this way, because it actually

is causing friction in the process.

And enough of that really does
keep customers moving forward.

I love that

Ramli: flow chart.

I was like, I can't, I'm already
imagining it's if this is the problem,

then this is sales that say, if this
is the problem, then it's marketing.

It's I can totally see that as a piece
of content that is like flowy chart.

It can be shared.

Shareil: And point internally to don't
just sit and blame your sales colleagues.

And it's easy to say the
sales it's very, I trust me.

I know it is very easy to say it was
the sales reps problem, or it was a

marketing problem or that's a product
problem, but there's a lot of internal

reflection that I think onboarding
teams and onboarding leaders don't do.

And it's easy to just point
fingers everywhere else.

And I think that.

That is as important as the rest
of that collaboration and feedback.

Kim: I was just going to add on
the onboarding never ends piece.

Actually, sure.

I haven't told you this yet, but I had
a call with one of our customers and

they were telling me about getting ready
and sending their first arrows plan.

So they sent one arrows plan.

They had a call with you,
Cheryl, and you advise them.

They were, you were like, where is
that customer stuck, move that task

to a different place in your process.

And then he just sent out his second plan.

He had made that change and
he's it was like magic, like

just that one small change.

Our next customer went through so quickly.

And I think that's like exactly
what we talk about all the time.

It's like you set up a
process, test the process.

Like you're not going to have
a perfect onboarding process.

Ever, but especially not initially.

So don't spend way too much time over
optimizing for the perfect process,

get something out and then analyze
and see everyone's getting stuck here.

This is a problem in our process.

And that is maybe something that you
can solve on the onboarding side by

breaking it up into different steps.

Or it's something like you said,
where marketing or product or someone

has to get involved, but start
small and look at a granular level.

Where are people getting stuck and
then just optimize that over time.

But don't wait for a big overhaul in
your process to make it perfect or.

Or also don't not optimize
your process because you're

worried about a huge rollout.

That's going to make a
game changing difference.

It's small changes over time
is what really adds up to a

better onboarding experience.

Shareil: Yeah, totally.

And a little bit more of a,
um, advanced or future kind of

approach to that too, is it.

You will inevitably have
hard and complex tasks.

It is also, I think, important to
acknowledge that they are going to

be hard and complex and not try to
oversimplify them at certain times.

And I think knowing that is also helpful
because inevitably when people do stall

there a little bit, at least you are
aware or expect that to be the case.

And so if there is, if there's nothing
else you can do there, that's okay.

There's other things you can optimize
within that, or there's other ways

to approach other parts of that
to keep things streamlined, but I

think it's important to know where
those kinds of milestones are that,

that help customers realize value.

And it's also important to know
where those points of friction are.

And I think if you are proactive
with those points of friction,

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