December 8, 2025 • 45 mins
If your retail transformation feels like a tool parade with little traction, this conversation will change your roadmap. We sit down with Barbara Wittmann, founder and CEO of the Digital Wisdom Collective, to unpack why technology isn’t the bottleneck—culture, clarity, and middle management are. Barbara has rescued “dead patient” projects across retail for 25 years, and she explains how empowering the right people, not buying the next platform, creates compounding impact.
We dig into the anatomy of human infrastructure: the trusted, often quiet, mid-level leaders who connect silos, translate strategy into action, and spot risks early. Barbara shares how to find them, how to give them a safe sandbox to practice new behaviors, and how small cross-functional cohorts can turn timid experts into confident catalysts. You’ll hear practical tactics like building shared mental models, setting clear guardrails, and starting every meeting with the same purpose and end-state visuals to keep distributed teams aligned across time zones.
Instead of drowning in dashboards, we explore how static high-level maps of systems and data restore orientation, why problem definition beats solution chasing, and how most retailers can unlock more value by optimizing existing stacks. Barbara’s “Mindset Before Machines” mantra reframes executive decisions: invest in people, language, and navigation before adding another tool. She paints a picture of the digitally wise organization where human architecture, technical architecture, and decision artifacts converge to strengthen the whole.
If you’re ready to reduce initiative overload, surface hidden change makers, and turn AI, data, and platforms into real results, press play. Subscribe, share this episode with a colleague who shapes transformation, and leave a review telling us which tactic you’ll adopt first.
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Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
SPEAKER_00 (00:08):
Well, hello everyone, and welcome to the
Digital Front Door.
I'm Scott That Addict.
Today's conversation reallytackles a topic that has become,
in my view, mission critical fora number of different types of
organizations, not justretailers, and that is digital
transformation.
There is the truth, in my view,and that is while most companies
(00:31):
are focused on the technology,the real challenge lies in
people and in culture that powerand take advantage and leverage
these new technologies.
In retail specifically, thiscouldn't be more true, whether
it's AI-driven merchandising orconnected stores or retail media
(00:55):
networks.
Technology is acceleratingchange faster than, in some
cases, teams that are taskedwith running that part of the
business can really adapt.
What retailers and brands todayneed is not just digital
expertise, but in my view,digital wisdom.
(01:16):
Joining me today is BarbaraWhitman.
She's the founder and the CEO ofthe Digital Wisdom Collective.
They are a consultancy thathelps organizations reimagine
transformation through the lensof human capability, leadership,
and culture.
Barbara has spent more than 25years looking through the lens
(01:38):
of human capability, leadership,and culture.
She has led a number of complexIT and business transformations,
and she is here to share herwisdom on how organizations that
build digital infrastructurethat turns digital strategy into
(01:59):
real-world success andreal-world results.
And Barbara, welcome to theDigital Front Door.
SPEAKER_01 (02:04):
Thanks for having me.
I've been looking forward tothis conversation all day.
SPEAKER_00 (02:09):
As have I.
As have I.
One of the things I've learnedabout you and your organization
is that you are really doingwhat I think is some fascinating
work helping leaders aimtechnology and align it to
innovation and purpose andpeople, quite frankly.
(02:30):
And I'm kind of wanted to startwith your perspective on how you
think some of the barriersunfold in terms of how
organizations, particularlywithin retailing, transform
their business in many ways.
And I think a lot of companiestalk about transformation as
(02:54):
it's just about a new platform,AI tools, data integration,
things like that.
But some of the things I'veheard you say is that really the
problem isn't technology, it'sour orientation towards it.
I'm just kind of curious, forthe benefit of the audience,
what do you what do you meanwhen you say that?
(03:14):
And how can retailers and brandsstart reframing digital
transformation as a peoplefirst, not a tech first journey
in your view?
SPEAKER_01 (03:25):
Man, that in itself would be a half-day conversation
here.
So I'm I'm trying to uh rollbackwards a little bit and uh
kind of start from uh the wherewhere I came into the
conversation.
Um so for 25 years I have workedmainly with retailers, so I'm
(03:46):
excited that we're talkingbecause that's my home base.
Um and uh I basically came inwhen digital transformation or
projects were uh broken.
So when a project is basicallythe dead patient on life
support, that that's when Iwould rush in, right?
(04:10):
Uh all the big consultancies,they run off and they're like,
hey, we got it, you know.
Um and uh I would uh come in anduh and fix things.
And you know, it I I mean, hey,at the start it was the big
adrenaline rush.
I'm like, okay, this is cool.
But then I found a repeatingpattern that um it's it never
(04:32):
fails because of technology.
It really fails because of umthe people are in the wrong
place, um, have the wrongskills, or are simply um not
empowered to speak up what theysee.
So basically in every projectI've encountered really, really
capable people in organizations,and once you give them a little
(04:54):
bit of support and a little bitof pick-me-up, they are
excelling.
And they're actually uh fixingthe problem on their own.
So my job became easy, and I waslike, so how do I do this?
And and um, you know, instead ofalways rushing in and doing the
same thing over and over again,how can we pre prevent this from
(05:16):
the get-go?
Um so that's how I poured what Iknow from 25 years into what I
do now.
And um so what what I have uhobserved and and what my you
know fixes to to get around isand obviously there is no easy
(05:37):
answer because it is a systemicproblem um is that you have to
define a couple of people withinyour organization, and that is
specifically the middle layerbecause that's the layer where
you cannot delegate complexity.
Everything upstairs complexitygets delegated.
(06:00):
But in the middle layer, theyare like they are the executors.
So um you want to find thepeople who really are hungry for
making things better and uh youwant to um start empowering
them.
Um and if you have a certainnumber of people in your middle
layer, and I always say yougotta start with four, um they
(06:25):
are starting to become aself-reinforcing um ecosystem
within the organization.
Um so that is one part of yourquestion, right?
Um how how do you get going inthis?
Um generally I think when youare picking out new technol
technology and adding newtechnology to the stack, um,
(06:48):
there needs to be a much broaderperspective on what the
implications are.
Um so I think the the problemthat we are seeing with um
transformation failing alsostarts with um how do we align
strategy and how do we defineinitiatives from there?
(07:08):
Because with every client that Isee, they have too many of
those.
It's almost like the fear ofmissing out, right?
And with AI, things don't becomebetter.
So we need to start looking frommany different angles and also
look from the people perspectiveand say, are we stressing out
our core resources?
You know, what do we do?
(07:29):
Consultants alone are never thefix.
And that seems to always be thevery simple solution for
organizations.
Um and I mean I know I'mshooting myself in the foot,
right?
I I've um put myself out of ajob, but I think I am uh more of
an enabler than anything.
And uh in these days, especiallywith AI, every organization,
(07:51):
especially retail, because it'sso much of the same.
So you need a differentiator.
You need to start cultivatingin-house innovation drivers.
SPEAKER_00 (08:01):
Yeah, I think that makes a lot of sense.
And it's it's so interestingbecause through my own
e-commerce experience, I learneda lot about concepts like user
acceptance testing, which is uhreally not so much in the
deployment phase as it is evenin the design phase of a
technology solution where thethe people who are tasked with
(08:23):
actually using whatever it isthat's going to get built are
this wonderful resource of whatis the business problem, to your
point, that you're trying tosolve.
And as you think about ways tosolve it, are the individuals at
multiple levels of theorganization who are actually
going to have to use thatsolution, did they help design
(08:44):
it?
Are they on board with it?
And are they effectivelychampions of it as it gets
implemented across anorganization?
It's interesting.
I was taught that by people froma software background, but I
don't always see it implementedin other retail organizations or
even places that I go to as aconsumer today, where literally
(09:04):
a technology solution is droppedon individuals and hope that
works out.
Here's the text port phonenumber if you have a call.
That's not really the way to doit, I think, is the way that
you're you're talking about thefact that you have to think
about the humans that are gonnause that solution, they're gonna
use that technology while you'redesigning it and as you're
(09:25):
implementing it and evenafterwards, rather than just
dropping uh a solution andtelling them to have a nice day,
right?
SPEAKER_01 (09:33):
Right.
And it's the humans that aregoing to use it, but also the
humans that are gonna execute onuh making it happen.
Um and uh you're you'redescribing the textbook example
on how it's it ought to be.
Um, but because in times wherewe are switching directions
(09:55):
because of external factors, umso often we are trying to cut
corners, and that's the um thedifficult thing, right?
So in in many projects that Istep in to try and write things
again, um the problem was neverreally defined that they're
trying to fix.
(10:16):
Um everyone is thinking insolution mode right away.
And um I mean it seems a littlebit uh it seems so natural,
right?
That we define the problem andthen we go forward.
Um, but we're trying to savetime and we're trying to jump
into a solution right away.
And then because we are in thesolution without knowing the
(10:38):
problem, it gets it gets evenworse, right?
And then uh something comes outat the end that needs an entire
rework.
So and that comes from pressurefrom the top for the most part.
It's like, hey, we're short ontime, we're short on on money,
so make it happen, make ithappen.
Um So sometimes it really uhpays off to take a breath, and
(11:01):
it doesn't mean that you have toentirely slow down, but it's
about asking the rightquestions, and it really is an
organizational muscle that youcan train.
SPEAKER_00 (11:12):
Indeed.
And kind of this humaninfrastructure is one of the
things that in in reading someof the materials that I've seen
you share really resonates withme.
And I'm curious in retailing uhin a number of different
functions, whether it's in salesor merchandising or operations.
It feels like technologyadoption is often it outpaces
(11:36):
the cultural readiness of the ofthe organization.
How do you define humaninfrastructure and what does it
look like inside a retailer orin inside a consumer brand
that's tried to modernize withit with with new tools, with new
data, with new businesschannels?
(11:56):
What does that look like in yourview?
SPEAKER_01 (12:01):
That's an interesting one.
Um so the human infrastructuremeans that you have uh core
people in your organization thatare functioning around a mindset
for innovation.
Um a core group of people thathave a clear uh direction of
(12:22):
values, you know, the valuesthat you function around, the
values that you are saying yesor no to certain things.
Um so that is the the main twothings.
And also it consists of peoplethat can connect the dots.
Um and connecting the dots meansacross silos, across systems, uh
(12:42):
from an end-to-end processperspective.
Um and uh that is really thecore traits of what we call the
human infrastructure.
And um the key is if you have acouple of people strategically
positioned in your organization,again, middle layer, they are
(13:03):
starting to become infectious.
They are starting to um to getothers inspired to really step
it up and question things.
And um this whole equation ofmindset to me is so critically
important because it reallyswitches from oh my god, that
(13:25):
was a top-level decision, youknow, I I cannot influence
anything, it's the victim mode,right?
To switching it over and sayingI'm seeing something that I can
maybe address with my boss.
And uh so they are becoming thedoers.
They are becoming the canariesin a way in the coal mine that
(13:47):
see things that are not good andthey would have the backbone to
address it.
So it is a lot about how you arecarrying yourself as a leader in
a middle layer of anorganization that really ties
together human infrastructure.
But that being said, it meansthat the people who are um, you
(14:10):
know, pointed out as they can bethe champions, they need to do a
little bit of self-developmentwork.
That means they need to look atwhat are their own limiting
beliefs, you know?
What are their own uh what istheir own attitude that's not
helping things.
SPEAKER_00 (14:34):
And I want to explore that a little bit more
if that's okay.
One of the things that reallystruck me in not only your
comments today, but what some ofthe things I've been reading
about what you do is this thisconcept of hidden change makers
in an organization, not just atthe top, but really uh, as you
mentioned, uh throughout themiddle of the organization.
(14:58):
And it strikes me that inretailing, that could be
category managers, it could beaccount executives at a consumer
brand, it could be leaders ofstore operations uh in a field
organization.
And I'm curious, as you adviseclients, how do some of those
mid-level managers become thecatalysts for transformation
(15:21):
rather just than justinterpreters?
And you kind of touched on thata little bit as they have to
have a certain level ofself-confidence and and be a
little bit a little bitfearless, but maybe dive a
little deeper about what aresome of the characteristics of
those uh middle out change uhleaders that that you see are
are the most successful in thework that you've done.
SPEAKER_01 (15:44):
Yeah.
So in in essence, they arereally easy to spot because
every organization has peoplethat are always consulted, not
openly, but people peoplegravitate to them and ask for
advice.
And I'm sure as I'm saying this,everyone has at least one or two
people in their head.
unknown (16:04):
Yes.
SPEAKER_01 (16:05):
And they are not usually the ones that are in a
specific department.
They are just the ones thatcarry either a lot of
institutional knowledge or thatsimply have a very different
angle to um to problems, right?
Um maybe some people that haveuh a lot of customer touch
(16:28):
points, or you know, the peoplethat are in in the customer
hotline seat and whatnot.
Um so it it usually uh is theones that uh people gravitate
to, that people trust, um, butuh they are also uh usually very
quiet.
They don't want to be visible.
(16:49):
Um yeah, and and that's youknow, that's fine, that's okay.
But if you strengthen thesepeople um and they actually get
a voice, they claim their theirseat at the change table.
And that's that's the type ofpeople you need in your
organization to really excel.
(17:09):
So how do you do this?
Because you cannot train thesepeople in your organization
because that is an echo chamber,sorry to say that, right?
Um even if you do individualtrainings and whatnot, no one
will ever openly speak aboutwhat's going on, or because it's
over you know, you put on agreat face.
(17:30):
Right?
And the other thing is, um it'sit's uh again a paradox in
itself.
When we have new softwareimplemented, we have several
test cycles before we set itlive.
Or we don't do that with peoplebecause if we upgrade what we
know, we don't have a testenvironment.
(17:53):
So I offer them a testenvironment and I put together
um small and curated cohorts umand that is cross-industry and
cross-hierarchy.
Um it's a safe space.
We meet um two times a month, sothe invested time is very low.
(18:19):
There is a self-study portionfor the mindset piece um that we
are uh teaching.
So it's a three to five hour uhtime invested per month.
So what that does is severalthings.
It gives them uh a testingsandbox, right?
(18:39):
They can show up as they are,they can try out things that
they have learned in um theworkbooks and they can show up
with a different side of themthat they may not feel
comfortable showing yet.
So we have a space where theycan gain confidence, where they
(19:01):
can really build that muscle.
And we throw together peoplefrom different angles.
I was just running a group thismorning, and uh there's for
example for-profit andnon-profit in there.
At first glance they would say,I have nothing to tell you.
(19:23):
But then but then at the end ofthe day, you know, it all comes
down to the same basics, youknow, it all comes down to what
are you focusing on, you know,what is your attitude towards
things.
And it's also asking people andhearing that people can give you
advice that are so out of yourwheelhouse.
(19:43):
So what they are trying out inour close groups, they can
directly transform and bringback into the organization
because what they will do isthey will ask different people
and they usually ask.
SPEAKER_00 (19:56):
Yeah, it's interesting because as you were
as you were talking about that,it occurs to me in my own
experience that I've seenexamples of people who go
through processes like this, andthey were already perhaps the
the loud and boisterous and thewhatabout askers, if you will,
in in meetings.
And then there are others whoare the exact opposite that were
(20:19):
maybe inclined to be rathertimid and weren't used to having
someone ask them what theythought, and just the simple act
of having a group like what youjust described in a setting and
an environment where they'reencouraged to share their
expertise.
Not only does the project andthe transformation benefit,
(20:43):
perhaps it also helps developthem as potential leaders
because they get a little bit ofconfidence that maybe they
weren't getting in in theeveryday of their job, but being
through this project, maybe uhand getting asked for their
expertise and their perspectiveand their expertise builds
potentially future leaders overan organization that the the
(21:06):
company might not have foundwere it not for this process
that you've you've kind of ledthem through.
Is that is that accurate in yourview?
SPEAKER_01 (21:14):
That's absolutely accurate because they would
always fall through the cracksof any high potential program,
right?
They would never be regardedbecause only the loud voices um
are heard.
And frankly, in today's time tomake the loud voices louder is
not really helping us as a as anorganization, right?
Um and also, you know, to stoketheir ego is not really helping
(21:38):
us.
So, you know, we're much betteroff at really empowering the the
timid people um in theorganization that actually have
something to say um and have aninterest of holding the strings
together and actually being atranslator.
So what I've seen in I've I'veuh ran these groups for a year
(21:59):
and a half.
So on average, about 70% ofpeople get promoted within the
first year.
unknown (22:06):
Wow.
SPEAKER_01 (22:07):
Because they are stepping it up, they are
becoming proactive.
Um they are saying, hey, youknow, if we want to make
projects faster, I have a coupleof ideas.
Would you be open to listen tothis?
So they actually have um, youknow, the courage to step it up
and say, hey, you know, I'm Ican be vulnerable, I can uh I
can bring in my ideas becausethey have had positive
(22:30):
experiences in our closed group.
The other the other thing that Ijust want to throw in as another
statistic is that uh almost 80%of the participants are
millennials.
And they would never get anytype of sophisticated training
within the organization becausethey are not the top-notch tier
(22:52):
and they are not the hot youngguns that are being brought in.
So you're basically you'releaving a ton of potential that
is unattended right now.
SPEAKER_00 (23:03):
No, I that makes so much sense.
And I and I've had theopportunity to witness exactly
what you're describing in someof the organizations, and it was
wonderful to see through atransformation process some of
these people become uh leadersof their full potential, but it
really started with pulling outtheir their expertise into an
(23:28):
environment that they feltconfident in sharing and then
them gaining that confidence.
And I've witnessed what you'redescribing so many times, and
it's so wonderful to see as aleader, but I fear that so many
organizations miss thatopportunity in the spirit of
moving fast and trying to get toa deadline and not taking the
(23:49):
opportunity to get the fullbenefit of the knowledge and
expertise uh uh of members oftheir team, right?
SPEAKER_01 (23:58):
Yeah.
And uh I mean, the the otherparadox that I see is that we
are spending a set amount ofmoney every year to upgrade our
servers, to see that ourcybersecurity is all tucked up,
all important things, right?
But then on the other hand, weare not tending to a human
(24:18):
infrastructure in exactly thesame way.
Um and we think that it's aone-time upgrade.
And instead, we are lagging waybehind.
You know, if you look at AImodels, it's getting updated at
the speed of light.
Um, so we are also needing totend to human infrastructure,
collective intelligence.
So what I offer to companies isnot a one-off training.
(24:40):
Um, these alumni people remainpart of the external ecosystem
that I offer, and they can gothrough continuous upgrades, dip
into that community while theyare starting to build their
in-house ecosystem.
And that to me is uh a huge umsuccess factor because they
still have the backup.
(25:01):
Um at the start of things, theywill still be the odd ones out
that bring a new type ofthinking.
So you need to give them somebacking where they can go and
say, hey, you know, just youknow, give me a little bit of a
pick-me-up.
SPEAKER_00 (25:16):
That makes a lot of sense.
You know, in my role as a as aconsultant, I talk to retailers
all the time that feel like theyare drounting in tools, whether
that is uh, I should say toolsand dashboards.
It could be things like retailmedia dashboards or digital
shells analytics or supply chainuh uh visibility.
(25:40):
And I'm I'm curious as youadvise clients um how to cut
through the noise and find theactual the wisdom, if you will,
clarity on what really mattersto the future of their business
and how do how do they make allthese technologies work?
Are there any kind of recurringthings uh that you see in terms
(26:00):
of how they take this increasedflow of data and metrics that
perhaps they didn't have 10years earlier and turn it into
action or actionable insights?
Well, what do you think of that?
SPEAKER_01 (26:17):
Oh, that is such a loaded topic, man.
SPEAKER_00 (26:21):
Um forgive me.
SPEAKER_01 (26:23):
No, it's it's good.
So um last year I stepped intobeing uh interim CIO for a
couple of months for uh one ofmy retail clients.
So and I can tell you that theother side of the fence is ugly.
Um so um I would cautioneveryone um at this point to add
(26:45):
more tools.
I think the best investment thatyou can make is to look at your
data.
Um right after your people,obviously.
But um I always compare what wehave, and it's so valid for
retail because there's so manydifferent things, as you say.
(27:07):
It's like an untended forest.
You just have um you have thenext software thing sprouting
up, and uh it's even worse withum agentic AI and such.
So, how do you weed your waythrough the forest?
You know, seriously, uh there islike and at some point you need
to bring your machete, and it'snot happy, right?
(27:30):
Because you need to startbreaking things, and that's what
happens.
Um so what I do a lot withclients is I uh I create a
navigation infrastructure forthem, and this is um something
that is the most profound andyet the most simple thing, but
companies don't have it.
And I may totally date myselfnow as starting to get really
(27:52):
old, but in my day when when westarted driving cars, we had
maps, physical maps, right?
Went on a road trip, put it onthe hood of the car and said,
Oh, look, we're here, you know,and this is where we want to go.
And this is essentially whatcompanies are lacking.
If I look at some of my clients,they have massive amounts of
(28:16):
documentation, of tools andeverything.
They have over 2,000 processesminutely detailed, but no one
sees the forest for the trees.
So what I do is maps that arehigh level and static.
(28:37):
Because if you go to a certainlevel, it never changes.
Except you are adding yetanother system.
Same goes for um for data maps,by the way.
Um and I don't stick to thecommon rules, so whoever is uh
into any modeling uh strategyhates me from the get-go, right?
(29:01):
Um but I am in the business ofmaking things visible and
understandable.
And uh then I hang these mapmaps as big printouts in in the
meeting rooms, and that really,really helps.
And you need to sing for yoursystems, also for your data, how
that's connected.
(29:22):
It really answers so manyquestions.
So you need to um start creatingtransparency.
Transparency sometimes is notreally wanted by some
departments.
Um but that's why I do that asan external source.
So you know I can cut throughthe noise, and then once they
have it, the people that areempowered through my training
(29:44):
can use that as a resource.
SPEAKER_00 (29:47):
You know, that makes a lot of sense, and it leads to
the to the next question I wasgoing to ask you.
You know, we're we're obviouslyseeing a tremendous amount of
change in the retail workforceitself.
Hybrid working models where noteverybody's working in the same
office, the same location.
Obviously, the use of AI thatautomates a number of tasks, and
(30:09):
a lot of rising expectationsaround teams that aren't
necessarily all in the sameplace, collaborating and driving
towards an ultimate outcome.
And I'm just curious what yourperspective is on how retail
leaders should be thinking aboutreskilling or upskilling their
(30:30):
teams, how communication ofdistributed teams maybe needs to
be done better.
And how do you prepare teams,not just for the project they're
working on today, but maybe tobe an organization that
transforms and evolves on anongoing basis going forward?
(30:51):
Do you have any advice that yougive maybe senior leaders on
what they should be thinkingabout over the long term, not
just today or this thisquarter's project or initiative?
SPEAKER_01 (31:04):
So the um the biggest and best tool I have
found is what uh what is calledshared mental model.
So do we all understand the samething when we talk about the
same thing, right?
Um so instead of throwing morecommunication tools or the next
best practice at it, um what Iwould advise people is to um
(31:27):
create artifacts that help youto understand the same things.
Um so that can be a very simpleglossary.
You know, things that arerepeatedly used over and over.
For example, for an initiative,what is the scope?
So when I go into meetings and Ihear about ten times in the
(31:50):
meeting the scope is clear, itraises red flags for me, right?
Um so you know, to to just haveuh the the outline, you know,
what are what are ourguardrails?
And I what I keep doing with mygroups, and at first they are so
irritated, but they keep gettingit because it is uh we are
(32:12):
creatures of habit.
We we learn by repeating.
So every meeting and it's almostreligious, you know, it's like
the prayer.
You pull up the same slides, yousay, Hey, you know, we set out
to do this.
And then you bring a visual andyou say, This is what we want to
have at the end of the game.
It really is aligning peoplearound the same thing, right?
unknown (32:34):
Right.
SPEAKER_00 (32:36):
No, and that that makes a lot of sense.
And I I think that there arethere are tools that enable it,
enable that, even if the team isnot all together.
But it perhaps, if anything, adistributed team in multiple
time zones, that communicationthat refocus on this is our
purpose, this is where ourheaded, perhaps even gets more
(33:00):
important in those scenariosthan if it's a team leading an
initiative that all works out ofthe same room in the same same
office, right?
SPEAKER_01 (33:09):
Absolutely.
And you know, if you talkdistributed teams, uh maybe also
across continents, also visualsbecome so important because
language um can bemisunderstood.
So having a crisp visual ofwhere you're going and why
you're doing it, um, superimportant.
Um also would what people keepunderestimating is the ground
(33:34):
rules uh when you start aproject.
And um usually from myconsulting background, you know,
working for large consultancies,it was more of a static thing,
you know.
Oh, we don't do this and wedon't do that.
Um and then it's more, you know,it's kind of pushed on to people
and it's never good because, youknow, hey, I was one of those
(33:57):
children, maybe you were too,but whenever somebody told me
not to do something, I became Ibecame rebellious, right?
Um so it's all it's also aboutsetting these boundaries
jointly.
Um and uh that's why at the coreof our model is values and we
define three values that areimportant uh for a team or for
(34:19):
an initiative.
And um you say how these showup, you know.
If we say trust is important,you know, how do we how do we
come together um and and showeach other trust?
Um so if it's a co-creationprocess, everyone is bought in.
And then when you bring thesethings up at the start of each
(34:40):
meeting and say, hey, rememberour three core values, it you
know, it rings true for people.
You can also cycle around andsay, hey, for the start of it,
give me one example how uh oneof those values showed up in a
positive way.
So it it uh it is starting tobecome a self-reinforcing cycle,
right?
SPEAKER_00 (35:00):
No, and it's interesting because what I think
you're describing uh kind of uhis the the very antithesis of
retail as a learningorganization.
In other words, the retailersthat I I think do best think
like startups, even if theyaren't still a startup in the
context of size or the theamount of time that they've been
(35:23):
in business.
And I'm curious, your yourconcept of digital wisdom, how
does it connect to that?
How how can retail leaders uhbuild a culture of curiosity, of
it's okay to experiment andpotentially fail at something,
but learn from it and makelearning and and and iterating
(35:45):
kind of part of the the DNA ofan organization as it as it
moves forward in the future.
SPEAKER_01 (35:53):
Um so essentially it it falls back to mindset, right?
You want to you want to createuh and that's an intrinsic thing
for uh for core people, you wantto empower them to um go beyond
their known fence line, right?
(36:13):
Um and you want to empower themto bring people together uh into
smaller groups to discussthings, and that's when
naturally innovation happens.
Um so if you give thempermission, they would usually
come up with very creative waysto to um come up with new things
(36:33):
to do or find improvements andso on.
Um so I think we've we've allovercomplicated things that it's
like, oh my god, we need aninnovation culture, you know,
and maybe we just need to needto pull the stops out for some
of the people, and and they aregetting everyone else uh
excited.
Um so that's one piece.
(36:55):
The other core principle that Ithink, and that's also a mindset
thing, we talk about ecosystems,and ecosystems are um generally
cyclical, you know, they run incycles, um but we all function
linear.
So, you know, we we cannotpreach one thing and do the
(37:17):
other thing.
So yeah, I mean it's like it'sit's uh right now we are killing
our own ideas through that.
So that means if you give peoplethe freedom to to play around
with things or if you ask theiropinion, you need to give them a
little bit of breathing space toplay.
(37:38):
And that doesn't mean that theyneed, you know, ten days out of
the year or something.
It's just it it's maybe uh it'snot like asking them every five
minutes, got it yet?
Huh huh?
What what?
You know?
Um and also not rushing from oneinitiative to the next because
they don't you know, there's somany ideas in the organization,
(38:01):
but they don't have anybreathing space in terms of just
mind capacity, right?
Because we are what we havegotten so good at starting
things.
You know, it's like it's alwaysten projects going in parallel.
Well, you know, maybe we canjust slim that down a little bit
and then we fix our innovationproblem.
(38:21):
So but that also starts at thevery top, you know.
Um and I run a workshop that'scalled Mindset Before Machines.
And I and I do that withleadership teams, it's it's
quite fun.
Because they come in with with atechnology that they think they
(38:42):
need, right?
And by the time you kind of yougo through the process with
them, they're like, well, wait,but now we talked for two hours
and we didn't talk technology.
It's like, oh right, yeah, it'san organizational problem.
SPEAKER_00 (38:56):
Yeah.
No, and that's the interestingthing, is that uh in in some
cases, it's not how how are wegoing to implement this
technology, is is do we need itand and why do we need it, and
how will ultimately the customerbenefit their internal uh
resources.
Store associates, uh, forexample, how will they benefit
(39:17):
from it?
How will they make their jobeasier?
And it's so interesting thatthat that dialogue, that
communication that youreferenced doesn't always
happen.
And I think it's going to evolvethe way senior leaders need to
lead initiatives, which is to doas much asking why as they do
(39:38):
asking how uh about things,because that that's that's part
of where innovation I thinkcomes from, and and just uh
being task focused instead ofoutcome focused uh is perhaps uh
at the core of some of thethings that that you really
(40:00):
guide some of your your clientsthrough, right?
SPEAKER_01 (40:03):
Yeah, yeah, exactly.
And I would also argue that mostretailers, what they have in
technology stack right now, theyonly use to 50%, and that's a
high assumption.
SPEAKER_00 (40:16):
Yes.
Yeah.
Um I've witnessed just that verything, so yes.
SPEAKER_01 (40:22):
Right.
So it's it's rather the questionof how can we optimize what we
already have without adding yetanother thing.
And I know that's a little bitcontrary because boy, I mean,
these software companies, theyare good at selling stuff,
right?
Um and uh we also need to uh cutback a little bit on seriously,
(40:42):
I think it's fear of missingout.
It's like, oh my god, oh my god.
But there's so much of value inthe organization, be it data, be
it uh systems that just need alittle tweaking, um, that you
can do a lot with very little.
SPEAKER_00 (41:01):
Interesting.
You know, the the last thing Iwanted to ask you is maybe to
look forward into the to thefuture a little bit.
And and I'm curious where yousee uh the next wave of
transformation going and whatdoes maybe the digitally wise
organization look like three,four, five years down the road?
(41:23):
And do you have any advice thatyou would give retail executives
that want to, to the degreepossible, future-proof their
teams and build a culture thatis effective at innovating and
using technology as a tool todrive their business forward?
Any thoughts on that?
SPEAKER_01 (41:43):
So a digitally wise organization um expands their
architecture team, and it islooking at different layers of
architecture, it is looking atthe human architecture, it is
looking at um the technicalarchitecture, and also what I
call uh orientation, you know,the uh what artifacts do we have
(42:06):
to actually make informeddecisions?
Um and uh obviously also lookingat data in an entirely different
way.
So wisdom is where all thesethings converge and where you
are making decisions thatdoesn't topple one or the other,
that actually strengthens andcomplements um everything you
(42:30):
already have.
That is the wise organization.
And that would mean that uhmaybe there's a little bit the
foot taken off the gas for justupping the technology budget we
have every year.
Um, and you would also look atyou know investments uh in a
much broader way.
SPEAKER_00 (42:52):
That makes a lot of sense.
Barbara, this has been such uhyou know an enlightening
conversation, and you'vereminded us a lot that
transformation isn't just atechnology project, it's a
people project uh every bit asmuch.
It occurs to me that retailersand brands can invest in all the
AI, automation, data analyticsin the world, but if they don't
(43:16):
invest in people and in culturethat bring these tools to life,
they will never realize the fullvalue of that initiative.
And you you just uh kind offirmed up uh that perspective, I
think in my mind, and hopefullyin our listeners as well.
I know that the work that you doat the Digital Wisdom Collective
(43:37):
shows that digital maturitybegins with human maturity, with
leadership, with trust, as youspoke to, and collaboration as
the foundation of everyinnovation that follows.
And so I just want to thank youfor sharing your thoughts and
giving, I think certainly me andI think our audience something
uh to think about.
(43:57):
So thank you for joining us.
SPEAKER_01 (44:00):
Wonderful.
Thanks for having me.
SPEAKER_00 (44:02):
You bet.
And for our listeners, if yourorganization is navigating
through digital transformation,I haven't met an organization in
retailing that isn't right now,and wants to understand how to
align technology with purposeand people, I'd invite you uh to
visit Barbara's website, thedigitalwisdomcollective.com, to
(44:24):
learn more about her work andways in which you can think
differently about innovation andtechnology and how it's used to
drive your business forward.
And so with that, I want tothank everybody for watching.
I'm Scott Benedict, and for theDigital Front Door, thanks for
listening.
Well, hello everyone, and welcome to the
Digital Front Door.
I'm Scott That Addict.
Today's conversation reallytackles a topic that has become,
in my view, mission critical fora number of different types of
organizations, not justretailers, and that is digital
transformation.
There is the truth, in my view,and that is while most companies
(00:31):
are focused on the technology,the real challenge lies in
people and in culture that powerand take advantage and leverage
these new technologies.
In retail specifically, thiscouldn't be more true, whether
it's AI-driven merchandising orconnected stores or retail media
(00:55):
networks.
Technology is acceleratingchange faster than, in some
cases, teams that are taskedwith running that part of the
business can really adapt.
What retailers and brands todayneed is not just digital
expertise, but in my view,digital wisdom.
(01:16):
Joining me today is BarbaraWhitman.
She's the founder and the CEO ofthe Digital Wisdom Collective.
They are a consultancy thathelps organizations reimagine
transformation through the lensof human capability, leadership,
and culture.
Barbara has spent more than 25years looking through the lens
(01:38):
of human capability, leadership,and culture.
She has led a number of complexIT and business transformations,
and she is here to share herwisdom on how organizations that
build digital infrastructurethat turns digital strategy into
(01:59):
real-world success andreal-world results.
And Barbara, welcome to theDigital Front Door.
SPEAKER_01 (02:04):
Thanks for having me.
I've been looking forward tothis conversation all day.
SPEAKER_00 (02:09):
As have I.
As have I.
One of the things I've learnedabout you and your organization
is that you are really doingwhat I think is some fascinating
work helping leaders aimtechnology and align it to
innovation and purpose andpeople, quite frankly.
(02:30):
And I'm kind of wanted to startwith your perspective on how you
think some of the barriersunfold in terms of how
organizations, particularlywithin retailing, transform
their business in many ways.
And I think a lot of companiestalk about transformation as
(02:54):
it's just about a new platform,AI tools, data integration,
things like that.
But some of the things I'veheard you say is that really the
problem isn't technology, it'sour orientation towards it.
I'm just kind of curious, forthe benefit of the audience,
what do you what do you meanwhen you say that?
(03:14):
And how can retailers and brandsstart reframing digital
transformation as a peoplefirst, not a tech first journey
in your view?
SPEAKER_01 (03:25):
Man, that in itself would be a half-day conversation
here.
So I'm I'm trying to uh rollbackwards a little bit and uh
kind of start from uh the wherewhere I came into the
conversation.
Um so for 25 years I have workedmainly with retailers, so I'm
(03:46):
excited that we're talkingbecause that's my home base.
Um and uh I basically came inwhen digital transformation or
projects were uh broken.
So when a project is basicallythe dead patient on life
support, that that's when Iwould rush in, right?
(04:10):
Uh all the big consultancies,they run off and they're like,
hey, we got it, you know.
Um and uh I would uh come in anduh and fix things.
And you know, it I I mean, hey,at the start it was the big
adrenaline rush.
I'm like, okay, this is cool.
But then I found a repeatingpattern that um it's it never
(04:32):
fails because of technology.
It really fails because of umthe people are in the wrong
place, um, have the wrongskills, or are simply um not
empowered to speak up what theysee.
So basically in every projectI've encountered really, really
capable people in organizations,and once you give them a little
(04:54):
bit of support and a little bitof pick-me-up, they are
excelling.
And they're actually uh fixingthe problem on their own.
So my job became easy, and I waslike, so how do I do this?
And and um, you know, instead ofalways rushing in and doing the
same thing over and over again,how can we pre prevent this from
(05:16):
the get-go?
Um so that's how I poured what Iknow from 25 years into what I
do now.
And um so what what I have uhobserved and and what my you
know fixes to to get around isand obviously there is no easy
(05:37):
answer because it is a systemicproblem um is that you have to
define a couple of people withinyour organization, and that is
specifically the middle layerbecause that's the layer where
you cannot delegate complexity.
Everything upstairs complexitygets delegated.
(06:00):
But in the middle layer, theyare like they are the executors.
So um you want to find thepeople who really are hungry for
making things better and uh youwant to um start empowering
them.
Um and if you have a certainnumber of people in your middle
layer, and I always say yougotta start with four, um they
(06:25):
are starting to become aself-reinforcing um ecosystem
within the organization.
Um so that is one part of yourquestion, right?
Um how how do you get going inthis?
Um generally I think when youare picking out new technol
technology and adding newtechnology to the stack, um,
(06:48):
there needs to be a much broaderperspective on what the
implications are.
Um so I think the the problemthat we are seeing with um
transformation failing alsostarts with um how do we align
strategy and how do we defineinitiatives from there?
(07:08):
Because with every client that Isee, they have too many of
those.
It's almost like the fear ofmissing out, right?
And with AI, things don't becomebetter.
So we need to start looking frommany different angles and also
look from the people perspectiveand say, are we stressing out
our core resources?
You know, what do we do?
(07:29):
Consultants alone are never thefix.
And that seems to always be thevery simple solution for
organizations.
Um and I mean I know I'mshooting myself in the foot,
right?
I I've um put myself out of ajob, but I think I am uh more of
an enabler than anything.
And uh in these days, especiallywith AI, every organization,
(07:51):
especially retail, because it'sso much of the same.
So you need a differentiator.
You need to start cultivatingin-house innovation drivers.
SPEAKER_00 (08:01):
Yeah, I think that makes a lot of sense.
And it's it's so interestingbecause through my own
e-commerce experience, I learneda lot about concepts like user
acceptance testing, which is uhreally not so much in the
deployment phase as it is evenin the design phase of a
technology solution where thethe people who are tasked with
(08:23):
actually using whatever it isthat's going to get built are
this wonderful resource of whatis the business problem, to your
point, that you're trying tosolve.
And as you think about ways tosolve it, are the individuals at
multiple levels of theorganization who are actually
going to have to use thatsolution, did they help design
(08:44):
it?
Are they on board with it?
And are they effectivelychampions of it as it gets
implemented across anorganization?
It's interesting.
I was taught that by people froma software background, but I
don't always see it implementedin other retail organizations or
even places that I go to as aconsumer today, where literally
(09:04):
a technology solution is droppedon individuals and hope that
works out.
Here's the text port phonenumber if you have a call.
That's not really the way to doit, I think, is the way that
you're you're talking about thefact that you have to think
about the humans that are gonnause that solution, they're gonna
use that technology while you'redesigning it and as you're
(09:25):
implementing it and evenafterwards, rather than just
dropping uh a solution andtelling them to have a nice day,
right?
SPEAKER_01 (09:33):
Right.
And it's the humans that aregoing to use it, but also the
humans that are gonna execute onuh making it happen.
Um and uh you're you'redescribing the textbook example
on how it's it ought to be.
Um, but because in times wherewe are switching directions
(09:55):
because of external factors, umso often we are trying to cut
corners, and that's the um thedifficult thing, right?
So in in many projects that Istep in to try and write things
again, um the problem was neverreally defined that they're
trying to fix.
(10:16):
Um everyone is thinking insolution mode right away.
And um I mean it seems a littlebit uh it seems so natural,
right?
That we define the problem andthen we go forward.
Um, but we're trying to savetime and we're trying to jump
into a solution right away.
And then because we are in thesolution without knowing the
(10:38):
problem, it gets it gets evenworse, right?
And then uh something comes outat the end that needs an entire
rework.
So and that comes from pressurefrom the top for the most part.
It's like, hey, we're short ontime, we're short on on money,
so make it happen, make ithappen.
Um So sometimes it really uhpays off to take a breath, and
(11:01):
it doesn't mean that you have toentirely slow down, but it's
about asking the rightquestions, and it really is an
organizational muscle that youcan train.
SPEAKER_00 (11:12):
Indeed.
And kind of this humaninfrastructure is one of the
things that in in reading someof the materials that I've seen
you share really resonates withme.
And I'm curious in retailing uhin a number of different
functions, whether it's in salesor merchandising or operations.
It feels like technologyadoption is often it outpaces
(11:36):
the cultural readiness of the ofthe organization.
How do you define humaninfrastructure and what does it
look like inside a retailer orin inside a consumer brand
that's tried to modernize withit with with new tools, with new
data, with new businesschannels?
(11:56):
What does that look like in yourview?
SPEAKER_01 (12:01):
That's an interesting one.
Um so the human infrastructuremeans that you have uh core
people in your organization thatare functioning around a mindset
for innovation.
Um a core group of people thathave a clear uh direction of
(12:22):
values, you know, the valuesthat you function around, the
values that you are saying yesor no to certain things.
Um so that is the the main twothings.
And also it consists of peoplethat can connect the dots.
Um and connecting the dots meansacross silos, across systems, uh
(12:42):
from an end-to-end processperspective.
Um and uh that is really thecore traits of what we call the
human infrastructure.
And um the key is if you have acouple of people strategically
positioned in your organization,again, middle layer, they are
(13:03):
starting to become infectious.
They are starting to um to getothers inspired to really step
it up and question things.
And um this whole equation ofmindset to me is so critically
important because it reallyswitches from oh my god, that
(13:25):
was a top-level decision, youknow, I I cannot influence
anything, it's the victim mode,right?
To switching it over and sayingI'm seeing something that I can
maybe address with my boss.
And uh so they are becoming thedoers.
They are becoming the canariesin a way in the coal mine that
(13:47):
see things that are not good andthey would have the backbone to
address it.
So it is a lot about how you arecarrying yourself as a leader in
a middle layer of anorganization that really ties
together human infrastructure.
But that being said, it meansthat the people who are um, you
(14:10):
know, pointed out as they can bethe champions, they need to do a
little bit of self-developmentwork.
That means they need to look atwhat are their own limiting
beliefs, you know?
What are their own uh what istheir own attitude that's not
helping things.
SPEAKER_00 (14:34):
And I want to explore that a little bit more
if that's okay.
One of the things that reallystruck me in not only your
comments today, but what some ofthe things I've been reading
about what you do is this thisconcept of hidden change makers
in an organization, not just atthe top, but really uh, as you
mentioned, uh throughout themiddle of the organization.
(14:58):
And it strikes me that inretailing, that could be
category managers, it could beaccount executives at a consumer
brand, it could be leaders ofstore operations uh in a field
organization.
And I'm curious, as you adviseclients, how do some of those
mid-level managers become thecatalysts for transformation
(15:21):
rather just than justinterpreters?
And you kind of touched on thata little bit as they have to
have a certain level ofself-confidence and and be a
little bit a little bitfearless, but maybe dive a
little deeper about what aresome of the characteristics of
those uh middle out change uhleaders that that you see are
are the most successful in thework that you've done.
SPEAKER_01 (15:44):
Yeah.
So in in essence, they arereally easy to spot because
every organization has peoplethat are always consulted, not
openly, but people peoplegravitate to them and ask for
advice.
And I'm sure as I'm saying this,everyone has at least one or two
people in their head.
unknown (16:04):
Yes.
SPEAKER_01 (16:05):
And they are not usually the ones that are in a
specific department.
They are just the ones thatcarry either a lot of
institutional knowledge or thatsimply have a very different
angle to um to problems, right?
Um maybe some people that haveuh a lot of customer touch
(16:28):
points, or you know, the peoplethat are in in the customer
hotline seat and whatnot.
Um so it it usually uh is theones that uh people gravitate
to, that people trust, um, butuh they are also uh usually very
quiet.
They don't want to be visible.
(16:49):
Um yeah, and and that's youknow, that's fine, that's okay.
But if you strengthen thesepeople um and they actually get
a voice, they claim their theirseat at the change table.
And that's that's the type ofpeople you need in your
organization to really excel.
(17:09):
So how do you do this?
Because you cannot train thesepeople in your organization
because that is an echo chamber,sorry to say that, right?
Um even if you do individualtrainings and whatnot, no one
will ever openly speak aboutwhat's going on, or because it's
over you know, you put on agreat face.
(17:30):
Right?
And the other thing is, um it'sit's uh again a paradox in
itself.
When we have new softwareimplemented, we have several
test cycles before we set itlive.
Or we don't do that with peoplebecause if we upgrade what we
know, we don't have a testenvironment.
(17:53):
So I offer them a testenvironment and I put together
um small and curated cohorts umand that is cross-industry and
cross-hierarchy.
Um it's a safe space.
We meet um two times a month, sothe invested time is very low.
(18:19):
There is a self-study portionfor the mindset piece um that we
are uh teaching.
So it's a three to five hour uhtime invested per month.
So what that does is severalthings.
It gives them uh a testingsandbox, right?
(18:39):
They can show up as they are,they can try out things that
they have learned in um theworkbooks and they can show up
with a different side of themthat they may not feel
comfortable showing yet.
So we have a space where theycan gain confidence, where they
(19:01):
can really build that muscle.
And we throw together peoplefrom different angles.
I was just running a group thismorning, and uh there's for
example for-profit andnon-profit in there.
At first glance they would say,I have nothing to tell you.
(19:23):
But then but then at the end ofthe day, you know, it all comes
down to the same basics, youknow, it all comes down to what
are you focusing on, you know,what is your attitude towards
things.
And it's also asking people andhearing that people can give you
advice that are so out of yourwheelhouse.
(19:43):
So what they are trying out inour close groups, they can
directly transform and bringback into the organization
because what they will do isthey will ask different people
and they usually ask.
SPEAKER_00 (19:56):
Yeah, it's interesting because as you were
as you were talking about that,it occurs to me in my own
experience that I've seenexamples of people who go
through processes like this, andthey were already perhaps the
the loud and boisterous and thewhatabout askers, if you will,
in in meetings.
And then there are others whoare the exact opposite that were
(20:19):
maybe inclined to be rathertimid and weren't used to having
someone ask them what theythought, and just the simple act
of having a group like what youjust described in a setting and
an environment where they'reencouraged to share their
expertise.
Not only does the project andthe transformation benefit,
(20:43):
perhaps it also helps developthem as potential leaders
because they get a little bit ofconfidence that maybe they
weren't getting in in theeveryday of their job, but being
through this project, maybe uhand getting asked for their
expertise and their perspectiveand their expertise builds
potentially future leaders overan organization that the the
(21:06):
company might not have foundwere it not for this process
that you've you've kind of ledthem through.
Is that is that accurate in yourview?
SPEAKER_01 (21:14):
That's absolutely accurate because they would
always fall through the cracksof any high potential program,
right?
They would never be regardedbecause only the loud voices um
are heard.
And frankly, in today's time tomake the loud voices louder is
not really helping us as a as anorganization, right?
Um and also, you know, to stoketheir ego is not really helping
(21:38):
us.
So, you know, we're much betteroff at really empowering the the
timid people um in theorganization that actually have
something to say um and have aninterest of holding the strings
together and actually being atranslator.
So what I've seen in I've I'veuh ran these groups for a year
(21:59):
and a half.
So on average, about 70% ofpeople get promoted within the
first year.
unknown (22:06):
Wow.
SPEAKER_01 (22:07):
Because they are stepping it up, they are
becoming proactive.
Um they are saying, hey, youknow, if we want to make
projects faster, I have a coupleof ideas.
Would you be open to listen tothis?
So they actually have um, youknow, the courage to step it up
and say, hey, you know, I'm Ican be vulnerable, I can uh I
can bring in my ideas becausethey have had positive
(22:30):
experiences in our closed group.
The other the other thing that Ijust want to throw in as another
statistic is that uh almost 80%of the participants are
millennials.
And they would never get anytype of sophisticated training
within the organization becausethey are not the top-notch tier
(22:52):
and they are not the hot youngguns that are being brought in.
So you're basically you'releaving a ton of potential that
is unattended right now.
SPEAKER_00 (23:03):
No, I that makes so much sense.
And I and I've had theopportunity to witness exactly
what you're describing in someof the organizations, and it was
wonderful to see through atransformation process some of
these people become uh leadersof their full potential, but it
really started with pulling outtheir their expertise into an
(23:28):
environment that they feltconfident in sharing and then
them gaining that confidence.
And I've witnessed what you'redescribing so many times, and
it's so wonderful to see as aleader, but I fear that so many
organizations miss thatopportunity in the spirit of
moving fast and trying to get toa deadline and not taking the
(23:49):
opportunity to get the fullbenefit of the knowledge and
expertise uh uh of members oftheir team, right?
SPEAKER_01 (23:58):
Yeah.
And uh I mean, the the otherparadox that I see is that we
are spending a set amount ofmoney every year to upgrade our
servers, to see that ourcybersecurity is all tucked up,
all important things, right?
But then on the other hand, weare not tending to a human
(24:18):
infrastructure in exactly thesame way.
Um and we think that it's aone-time upgrade.
And instead, we are lagging waybehind.
You know, if you look at AImodels, it's getting updated at
the speed of light.
Um, so we are also needing totend to human infrastructure,
collective intelligence.
So what I offer to companies isnot a one-off training.
(24:40):
Um, these alumni people remainpart of the external ecosystem
that I offer, and they can gothrough continuous upgrades, dip
into that community while theyare starting to build their
in-house ecosystem.
And that to me is uh a huge umsuccess factor because they
still have the backup.
(25:01):
Um at the start of things, theywill still be the odd ones out
that bring a new type ofthinking.
So you need to give them somebacking where they can go and
say, hey, you know, just youknow, give me a little bit of a
pick-me-up.
SPEAKER_00 (25:16):
That makes a lot of sense.
You know, in my role as a as aconsultant, I talk to retailers
all the time that feel like theyare drounting in tools, whether
that is uh, I should say toolsand dashboards.
It could be things like retailmedia dashboards or digital
shells analytics or supply chainuh uh visibility.
(25:40):
And I'm I'm curious as youadvise clients um how to cut
through the noise and find theactual the wisdom, if you will,
clarity on what really mattersto the future of their business
and how do how do they make allthese technologies work?
Are there any kind of recurringthings uh that you see in terms
(26:00):
of how they take this increasedflow of data and metrics that
perhaps they didn't have 10years earlier and turn it into
action or actionable insights?
Well, what do you think of that?
SPEAKER_01 (26:17):
Oh, that is such a loaded topic, man.
SPEAKER_00 (26:21):
Um forgive me.
SPEAKER_01 (26:23):
No, it's it's good.
So um last year I stepped intobeing uh interim CIO for a
couple of months for uh one ofmy retail clients.
So and I can tell you that theother side of the fence is ugly.
Um so um I would cautioneveryone um at this point to add
(26:45):
more tools.
I think the best investment thatyou can make is to look at your
data.
Um right after your people,obviously.
But um I always compare what wehave, and it's so valid for
retail because there's so manydifferent things, as you say.
(27:07):
It's like an untended forest.
You just have um you have thenext software thing sprouting
up, and uh it's even worse withum agentic AI and such.
So, how do you weed your waythrough the forest?
You know, seriously, uh there islike and at some point you need
to bring your machete, and it'snot happy, right?
(27:30):
Because you need to startbreaking things, and that's what
happens.
Um so what I do a lot withclients is I uh I create a
navigation infrastructure forthem, and this is um something
that is the most profound andyet the most simple thing, but
companies don't have it.
And I may totally date myselfnow as starting to get really
(27:52):
old, but in my day when when westarted driving cars, we had
maps, physical maps, right?
Went on a road trip, put it onthe hood of the car and said,
Oh, look, we're here, you know,and this is where we want to go.
And this is essentially whatcompanies are lacking.
If I look at some of my clients,they have massive amounts of
(28:16):
documentation, of tools andeverything.
They have over 2,000 processesminutely detailed, but no one
sees the forest for the trees.
So what I do is maps that arehigh level and static.
(28:37):
Because if you go to a certainlevel, it never changes.
Except you are adding yetanother system.
Same goes for um for data maps,by the way.
Um and I don't stick to thecommon rules, so whoever is uh
into any modeling uh strategyhates me from the get-go, right?
(29:01):
Um but I am in the business ofmaking things visible and
understandable.
And uh then I hang these mapmaps as big printouts in in the
meeting rooms, and that really,really helps.
And you need to sing for yoursystems, also for your data, how
that's connected.
(29:22):
It really answers so manyquestions.
So you need to um start creatingtransparency.
Transparency sometimes is notreally wanted by some
departments.
Um but that's why I do that asan external source.
So you know I can cut throughthe noise, and then once they
have it, the people that areempowered through my training
(29:44):
can use that as a resource.
SPEAKER_00 (29:47):
You know, that makes a lot of sense, and it leads to
the to the next question I wasgoing to ask you.
You know, we're we're obviouslyseeing a tremendous amount of
change in the retail workforceitself.
Hybrid working models where noteverybody's working in the same
office, the same location.
Obviously, the use of AI thatautomates a number of tasks, and
(30:09):
a lot of rising expectationsaround teams that aren't
necessarily all in the sameplace, collaborating and driving
towards an ultimate outcome.
And I'm just curious what yourperspective is on how retail
leaders should be thinking aboutreskilling or upskilling their
(30:30):
teams, how communication ofdistributed teams maybe needs to
be done better.
And how do you prepare teams,not just for the project they're
working on today, but maybe tobe an organization that
transforms and evolves on anongoing basis going forward?
(30:51):
Do you have any advice that yougive maybe senior leaders on
what they should be thinkingabout over the long term, not
just today or this thisquarter's project or initiative?
SPEAKER_01 (31:04):
So the um the biggest and best tool I have
found is what uh what is calledshared mental model.
So do we all understand the samething when we talk about the
same thing, right?
Um so instead of throwing morecommunication tools or the next
best practice at it, um what Iwould advise people is to um
(31:27):
create artifacts that help youto understand the same things.
Um so that can be a very simpleglossary.
You know, things that arerepeatedly used over and over.
For example, for an initiative,what is the scope?
So when I go into meetings and Ihear about ten times in the
(31:50):
meeting the scope is clear, itraises red flags for me, right?
Um so you know, to to just haveuh the the outline, you know,
what are what are ourguardrails?
And I what I keep doing with mygroups, and at first they are so
irritated, but they keep gettingit because it is uh we are
(32:12):
creatures of habit.
We we learn by repeating.
So every meeting and it's almostreligious, you know, it's like
the prayer.
You pull up the same slides, yousay, Hey, you know, we set out
to do this.
And then you bring a visual andyou say, This is what we want to
have at the end of the game.
It really is aligning peoplearound the same thing, right?
unknown (32:34):
Right.
SPEAKER_00 (32:36):
No, and that that makes a lot of sense.
And I I think that there arethere are tools that enable it,
enable that, even if the team isnot all together.
But it perhaps, if anything, adistributed team in multiple
time zones, that communicationthat refocus on this is our
purpose, this is where ourheaded, perhaps even gets more
(33:00):
important in those scenariosthan if it's a team leading an
initiative that all works out ofthe same room in the same same
office, right?
SPEAKER_01 (33:09):
Absolutely.
And you know, if you talkdistributed teams, uh maybe also
across continents, also visualsbecome so important because
language um can bemisunderstood.
So having a crisp visual ofwhere you're going and why
you're doing it, um, superimportant.
Um also would what people keepunderestimating is the ground
(33:34):
rules uh when you start aproject.
And um usually from myconsulting background, you know,
working for large consultancies,it was more of a static thing,
you know.
Oh, we don't do this and wedon't do that.
Um and then it's more, you know,it's kind of pushed on to people
and it's never good because, youknow, hey, I was one of those
(33:57):
children, maybe you were too,but whenever somebody told me
not to do something, I became Ibecame rebellious, right?
Um so it's all it's also aboutsetting these boundaries
jointly.
Um and uh that's why at the coreof our model is values and we
define three values that areimportant uh for a team or for
(34:19):
an initiative.
And um you say how these showup, you know.
If we say trust is important,you know, how do we how do we
come together um and and showeach other trust?
Um so if it's a co-creationprocess, everyone is bought in.
And then when you bring thesethings up at the start of each
(34:40):
meeting and say, hey, rememberour three core values, it you
know, it rings true for people.
You can also cycle around andsay, hey, for the start of it,
give me one example how uh oneof those values showed up in a
positive way.
So it it uh it is starting tobecome a self-reinforcing cycle,
right?
SPEAKER_00 (35:00):
No, and it's interesting because what I think
you're describing uh kind of uhis the the very antithesis of
retail as a learningorganization.
In other words, the retailersthat I I think do best think
like startups, even if theyaren't still a startup in the
context of size or the theamount of time that they've been
(35:23):
in business.
And I'm curious, your yourconcept of digital wisdom, how
does it connect to that?
How how can retail leaders uhbuild a culture of curiosity, of
it's okay to experiment andpotentially fail at something,
but learn from it and makelearning and and and iterating
(35:45):
kind of part of the the DNA ofan organization as it as it
moves forward in the future.
SPEAKER_01 (35:53):
Um so essentially it it falls back to mindset, right?
You want to you want to createuh and that's an intrinsic thing
for uh for core people, you wantto empower them to um go beyond
their known fence line, right?
(36:13):
Um and you want to empower themto bring people together uh into
smaller groups to discussthings, and that's when
naturally innovation happens.
Um so if you give thempermission, they would usually
come up with very creative waysto to um come up with new things
(36:33):
to do or find improvements andso on.
Um so I think we've we've allovercomplicated things that it's
like, oh my god, we need aninnovation culture, you know,
and maybe we just need to needto pull the stops out for some
of the people, and and they aregetting everyone else uh
excited.
Um so that's one piece.
(36:55):
The other core principle that Ithink, and that's also a mindset
thing, we talk about ecosystems,and ecosystems are um generally
cyclical, you know, they run incycles, um but we all function
linear.
So, you know, we we cannotpreach one thing and do the
(37:17):
other thing.
So yeah, I mean it's like it'sit's uh right now we are killing
our own ideas through that.
So that means if you give peoplethe freedom to to play around
with things or if you ask theiropinion, you need to give them a
little bit of breathing space toplay.
(37:38):
And that doesn't mean that theyneed, you know, ten days out of
the year or something.
It's just it it's maybe uh it'snot like asking them every five
minutes, got it yet?
Huh huh?
What what?
You know?
Um and also not rushing from oneinitiative to the next because
they don't you know, there's somany ideas in the organization,
(38:01):
but they don't have anybreathing space in terms of just
mind capacity, right?
Because we are what we havegotten so good at starting
things.
You know, it's like it's alwaysten projects going in parallel.
Well, you know, maybe we canjust slim that down a little bit
and then we fix our innovationproblem.
(38:21):
So but that also starts at thevery top, you know.
Um and I run a workshop that'scalled Mindset Before Machines.
And I and I do that withleadership teams, it's it's
quite fun.
Because they come in with with atechnology that they think they
(38:42):
need, right?
And by the time you kind of yougo through the process with
them, they're like, well, wait,but now we talked for two hours
and we didn't talk technology.
It's like, oh right, yeah, it'san organizational problem.
SPEAKER_00 (38:56):
Yeah.
No, and that's the interestingthing, is that uh in in some
cases, it's not how how are wegoing to implement this
technology, is is do we need itand and why do we need it, and
how will ultimately the customerbenefit their internal uh
resources.
Store associates, uh, forexample, how will they benefit
(39:17):
from it?
How will they make their jobeasier?
And it's so interesting thatthat that dialogue, that
communication that youreferenced doesn't always
happen.
And I think it's going to evolvethe way senior leaders need to
lead initiatives, which is to doas much asking why as they do
(39:38):
asking how uh about things,because that that's that's part
of where innovation I thinkcomes from, and and just uh
being task focused instead ofoutcome focused uh is perhaps uh
at the core of some of thethings that that you really
(40:00):
guide some of your your clientsthrough, right?
SPEAKER_01 (40:03):
Yeah, yeah, exactly.
And I would also argue that mostretailers, what they have in
technology stack right now, theyonly use to 50%, and that's a
high assumption.
SPEAKER_00 (40:16):
Yes.
Yeah.
Um I've witnessed just that verything, so yes.
SPEAKER_01 (40:22):
Right.
So it's it's rather the questionof how can we optimize what we
already have without adding yetanother thing.
And I know that's a little bitcontrary because boy, I mean,
these software companies, theyare good at selling stuff,
right?
Um and uh we also need to uh cutback a little bit on seriously,
(40:42):
I think it's fear of missingout.
It's like, oh my god, oh my god.
But there's so much of value inthe organization, be it data, be
it uh systems that just need alittle tweaking, um, that you
can do a lot with very little.
SPEAKER_00 (41:01):
Interesting.
You know, the the last thing Iwanted to ask you is maybe to
look forward into the to thefuture a little bit.
And and I'm curious where yousee uh the next wave of
transformation going and whatdoes maybe the digitally wise
organization look like three,four, five years down the road?
(41:23):
And do you have any advice thatyou would give retail executives
that want to, to the degreepossible, future-proof their
teams and build a culture thatis effective at innovating and
using technology as a tool todrive their business forward?
Any thoughts on that?
SPEAKER_01 (41:43):
So a digitally wise organization um expands their
architecture team, and it islooking at different layers of
architecture, it is looking atthe human architecture, it is
looking at um the technicalarchitecture, and also what I
call uh orientation, you know,the uh what artifacts do we have
(42:06):
to actually make informeddecisions?
Um and uh obviously also lookingat data in an entirely different
way.
So wisdom is where all thesethings converge and where you
are making decisions thatdoesn't topple one or the other,
that actually strengthens andcomplements um everything you
(42:30):
already have.
That is the wise organization.
And that would mean that uhmaybe there's a little bit the
foot taken off the gas for justupping the technology budget we
have every year.
Um, and you would also look atyou know investments uh in a
much broader way.
SPEAKER_00 (42:52):
That makes a lot of sense.
Barbara, this has been such uhyou know an enlightening
conversation, and you'vereminded us a lot that
transformation isn't just atechnology project, it's a
people project uh every bit asmuch.
It occurs to me that retailersand brands can invest in all the
AI, automation, data analyticsin the world, but if they don't
(43:16):
invest in people and in culturethat bring these tools to life,
they will never realize the fullvalue of that initiative.
And you you just uh kind offirmed up uh that perspective, I
think in my mind, and hopefullyin our listeners as well.
I know that the work that you doat the Digital Wisdom Collective
(43:37):
shows that digital maturitybegins with human maturity, with
leadership, with trust, as youspoke to, and collaboration as
the foundation of everyinnovation that follows.
And so I just want to thank youfor sharing your thoughts and
giving, I think certainly me andI think our audience something
uh to think about.
(43:57):
So thank you for joining us.
SPEAKER_01 (44:00):
Wonderful.
Thanks for having me.
SPEAKER_00 (44:02):
You bet.
And for our listeners, if yourorganization is navigating
through digital transformation,I haven't met an organization in
retailing that isn't right now,and wants to understand how to
align technology with purposeand people, I'd invite you uh to
visit Barbara's website, thedigitalwisdomcollective.com, to
(44:24):
learn more about her work andways in which you can think
differently about innovation andtechnology and how it's used to
drive your business forward.
And so with that, I want tothank everybody for watching.
I'm Scott Benedict, and for theDigital Front Door, thanks for
listening.
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