Episode 14 – Caging confidence gremlins with UK Marketing Director Helen Tupper

Episode 14 – Caging confidence gremlins with UK Marketing Director Helen Tupper


VOICEOVER: I think if careers as being quite
“squiggly.” I think, you know, careers of yesteryear used
to be like staircases, not quite linear, you knew where you were going. And I think now, careers can be very squiggly. You’re not kind of sure what your next role
is. Your next role might not even exist yet. (Break for HIMSS 18 Advertisement.) VOICEOVER: You are listening to the Women
in Business and Technology podcast from Microsoft. In each episode, you’ll hear from women in
amazing technology and business roles, as well as male allies who are helping to make
the industries more inclusive. We’re diving into programs that promote greater
diversity in the pipeline, and bringing you tips on how to build a successful career and
a supportive community. Welcome to Women in Business and Technology. (Music.) SONIA DARA: Welcome to Episode 14 of Women
in Business and Technology. I’m Sonia Dara. COLLEEN O’BRIEN: And I’m Colleen O’Brien. SONIA DARA: We’re starting the show in our
Communicate Connect segment with a conversation that I had with Sage Kealohilani Quiamno,
the community manager and digital media strategies for Ladies Get Paid, a startup focused on
closing the gender wage gap. COLLEEN O’BRIEN: And then we’ll jump into
an interview I had with Helen Tupper, a commercial marketing director here at Microsoft, and
the co-founder of Amazing If, a career development and training business. SONIA DARA: Finally, we’ll wrap things up
in our Cutting Edge segment with a discussion about Google’s new 3D art installation at
the National Museum of African American History and Culture, which was unveiled on February
1st in honor of Black History Month. COLLEEN O’BRIEN: Before we dive in, we want
to encourage you to listen all the way through to the end of the show. In Episode 8, we started closing each show
with bite-sized challenges that you can tackle to better invest in your career and promote
workplace inclusion. So stay tuned all the way through for those
missions. (Music.) COLLEEN O’BRIEN: It’s great to be back in
the studio with you, Sonia. What’s new with you? SONIA DARA: To be honest, I’m still on a high
from attending the Female Founders Alliance Champion Awards earlier this month. The Female Founders Alliance is, of course,
a network of women founders and leaders of venture-scale startups, as well as the community
that supports them — I put myself in that bucket. COLLEEN O’BRIEN: Yeah, absolutely. SONIA DARA: And on February 1st; the organization
hosted an awards ceremony to recognize people and organizations that champion women. COLLEEN O’BRIEN: Yeah, that was such a cool
event. And it was amazing to see so many of our past
guests we’ve hosted on this show nominated for those awards — Megan McNally won the
Advocate Award for her work with the F-Bomb Breakfast Club, which Sonia, you talked about
in the interview. SONIA DARA: Yes. COLLEEN O’BRIEN: And Kal Viswanathan, who
was one of my recent guests, was honored as an unsung hero for her work with Kal Academy. So congrats to both of you, Megan and Kal. SONIA DARA: Woo! Even the details of the event were rooted
in this notion of supporting women. All of the in-kind sponsors were female founded
or female led, so we had amazing drinks from Stoup Brewing, and delicious food from Nuflours
Bakery and Choukette. COLLEEN O’BRIEN: Yeah, all around, it was
such a great night, and I highly recommend staying posted on all Female Founders Alliance
news. For our listeners, you can learn more about
the organization at femalefounders.org, where they have a newsletter signup, or you can
follow them on Twitter. Their handle is @2point19. That, of course, is a reference to the fact
that in 2016, women got just 2.19 percent of all venture capital funding. But with organizations like Female Founders
Alliance providing the resources and community to women entrepreneurs, we’re positive that
that number will soon be history. (Music.) VOICEOVER: Community Connect, get involved
and stay connected. SONIA DARA: Ladies Get Paid is a female-owned
career development startup with a mission of closing the gender wage gap one raise at
a time. They seem to give women the resources and
tools that they need to advocate for themselves at work. Many of these resources are shared at events
in the 20 cities where Ladies Get Paid has a presence. Colleen and I wanted to learn more about the
organization, and headed to a salary negotiation 101 workshop in downtown Seattle. After an amazing and informative session,
we sat down with Ladies Get Paid Communication Manager, Digital Media Strategist, and the
workshop presenter Sage Kealohilani Quiamno. Sage explained why this cause of closing the
gender pay gap is so important to her. SAGE QUIAMNO: I’m passionate about this because
I’ve been through this. I worked in male-dominated industries — tech,
real estate, startup — and never fit in. I never fit in, and there was no one there
to advocate for myself, and I just sat down and researched and did my own grind, and I
have all this knowledge that I want to share with other women. And I found Ladies Get Paid in New York, and
they understood me. And I was, like, “This is phenomenal.” This is what I want other women to have, especially
younger women, women coming out of college, women getting their first job, or negotiating
for a senior-level position. We need more females in leadership roles. SONIA DARA: Asking for more at work can sometimes
feel like a scary or overwhelming experience. Sage’s advice is to lean on your community
for support and collective knowledge. SAGE QUIAMNO: Everybody wants a promotion. Everybody wants to be felt respected, as we
should be. But, obviously, in this society, we’re not,
you know. And this is why we come together to share
resources, to share stories, feel validated in how we feel, and also confront our fears. SONIA DARA: The workshop offered a great mindset
shift for me in thinking about compensation beyond dollars and cents. SAGE QUIAMNO: We call it “full compensation.” So you can negotiate flexibility. So if you’re more productive by working at
home on Fridays, you can negotiate that. You can negotiate for transportation costs,
your phone bill if you’re using your personal phone and your data plan for your job, negotiate
that. I’ve successfully negotiated my outfits and
now every speaking event that I have, I am “Nordstrom’d out” and I have a stylist, his
name is Chris, he’s fabulous. Meet him there in Nordstrom, Seattle. But I’m letting you know that I was taught
when I was younger from my father that if you don’t ask, you won’t get. So if you are really wanting something and
you’re passionate about something and you want to get paid for, negotiate and put that
on the table and say, “This is why I need this to be taken care of.” SONIA DARA: One of my biggest takeaways from
the workshop is that pay equity is about respect. Asking for more is not just about us as individuals,
but for the women entering the workforce in our wake. SAGE QUIAMNO: This is a movement that can’t
happen from one woman. Right? Like, this is something that everyone needs
to get on board. It is valuable that if you see another woman
living her life and getting paid what she deserves, then you feel more empowered to
do so, and that’s the effect that we want to have. SONIA DARA: For more information about Ladies
Get Paid, including details about their online network and upcoming workshops, webinars,
and meetups, head to ladiesgetpaid.com. Membership is free; just click “join” to start
receiving their weekly newsletter so you’re always up to date on the latest. You can also follow them on Twitter and Instagram
@ladiesgetpaid. And now, let’s get on with the interview. (Music.) COLLEEN O’BRIEN: I’m excited to welcome to
the show today Microsoft Commercial Marketing Director Helen Tupper. Helen, welcome to the show. HELEN TUPPER: Very much, thanks for having
me. COLLEEN O’BRIEN: Can you tell our listeners
a little bit about yourself and what your role in marketing entails? HELEN TUPPER: I’m the commercial marketing
director, as you said, in Microsoft U.K. And that means me and my team — I’ve got
a team of about 20-plus people — we effectively translate the marketing strategy and the product
strategy that we get from corp, and then we activate that in the field. And then I think it’s probably a bit of a
cliché, but for me, that’s all about making sure we have the right message for the right
audience and we get it to them in the right place at the right time. Which it really is a bit of a cliché to say
that, but that’s exactly what we do. So we do lots of audience mapping, we look
at message resonance, we look at the channels and the industries we should be talking to,
we look at their customer journey and when we’re going to have the most impact. So a lot of the work that my team do is about
marketing plans that are based around those principles. And then I also have parts of my team that
work in partnership with sales, and we do lots of work around sales enablement and account-based
engagement to help the sales teams meet their targets. So it’s sort of this hybrid team that work
both with the business groups and create marketing plans to help them drive their business, and
then work in partnerships with the sales team to help grow their existing accounts. COLLEEN O’BRIEN: You mentioned that the strategy
plans are getting handed over from corp. Of course, Microsoft is headquartered here
in Redmond, but you’re calling today from the U.K. What is it like to work in a subsidiary organization? HELEN TUPPER: It’s all I’ve known, actually. So far at Microsoft, I’ve been at Microsoft
for about a year. And whilst I’ve worked in other organizations,
I don’t really know the difference in Microsoft corp versus a subsidiary. So my context of working in a subsidiary,
probably relevant to other places I’ve worked, is that it’s a very dynamic place, there’s
always a lot going on. I find it particularly collaborative, which
I think is part of the Microsoft culture that I’ve found since I’ve been here. So even though there are lots of distinct
functions, there’s lots of work that we do in the field that cuts across those functions. So I will work with, as I said, the sales
teams and I’ll work with the account teams and we’ll work with the business groups to
try and deliver products and services and activities that all ladder up to the U.K.
strategy. And what I would say as well — even though
there’s this dynamism and kind of a lot of business going on in the field, it is all
very connected. We have a very visible U.K. leadership team. So it’s headed up by Cindy Rose, and then
under her she has just a very visible leadership team. So I feel that I can go and speak to any of
those leadership teams. We get a lot of clarity through regular town
halls and lots of communications, and I think if you didn’t have that clarity, all this
business and dynamism could feel a bit disconnected. But because we have that clarity in the field,
it sort of stitches everything together, and you can see what all the work that you’re
doing is laddering up to and what it’s in service of. So I find it a brilliant place to work. Really high energy, lots to do. COLLEEN O’BRIEN: We’ve had a couple of conversations
on this show about the globalization of products and the necessity of translating to local
markets. Does your team play a role in making sure
that the strategy that’s handed over from corp really translates to your local audience
in an inclusive way? HELEN TUPPER: Absolutely, so earlier today,
I was talking about the education market, for example. And the education market in the U.K. is very
different to, for example, the U.S. education market. And so we have to take account the different
learning stages that people go through, the different environments they learn in, and
make sure that we, overall, take the overarching objectives and strategy that we get down,
but that we then — it’s this translation exercise, and it takes a lot of local market
knowledge, and we do have to do a lot of research and insight in order for that translation
process to work, but if we didn’t do that, what we would land in the field would not
be as relevant and wouldn’t be as credible, and our competitors would kind of take our
share in the local market. So it’s a really important exercise, and it’s
why my team have to be experts locally, but they also have to be able to do this translation
exercise as well, so they’ve kind of got half a head on strategy, but then half a head on
the detail of the industries that they’re working with. COLLEEN O’BRIEN: Yeah, I think that education
is such a great example, something that you can’t take a one-size-fits-all approach to
when you’re marketing globally. That’s great. HELEN TUPPER: Absolutely. COLLEEN O’BRIEN: So speaking of education,
personal developmental, Microsoft recently hosted Future Decoded in London, a conference
on disruptive technology and how it will impact people and businesses. I know that you were an attendee at this event. What were your big take-aways? HELEN TUPPER: Yeah, so I was an attendee,
and I was also part of the team organizing it, so I was very close to the detail of running
up to it and kind of behind the scenes, making everything happen across the two days. The overall event was all focused on cloud
data and AI, and we had some amazing Microsoft speakers come over to talk to some of those
points. I think there are probably two main take-aways
for me, and I think, you know, they’re very personal things from where I’m coming from. The first was about quantum computing. So we had that on the agenda, and we had a
whole track running on the first day of Future Decoded on quantum, as well as part of our
keynote session. And we did have some debate about was this
going to appeal to our business as well as our technical audience? And, you know, were people to have a quantum
keynote at Future Decoded? And there was such a high level of engagement
in quantum computing and such a buzz on social about it, and for me, it just made me think,
“Oh, Microsoft are doing the right thing, not just in terms of our investment in that
technology, but in sharing what we’re doing with people, and involving them in the conversation
early on.” I think it gets a lot of engagement and support
for where Microsoft is going. So for me, that was something quite exciting
to see. And then the second thing was something that
we did in the U.K. We launched a report this year about the cultural
transformation that you need to have in an organization to underpin the digital transformation. You know, we’ve seen an awful lot, and we’ve
written an awful lot ourselves around why organizations need to digitally transform
and where they start and how they get support for it, all those sorts of things. But I haven’t seen so much work being done
on actually, you’ve got to get the cultural transformation right in order for the digital
transformation to land. And we launched a report, which we talked
about it in the keynotes, that for me, I was just really excited and really proud that
we were not just looking at the technical elements of digital transformation, but that
we were also helping our partners and our customers to think about the underlying issues,
which you might think, “Oh, that’s not core to what Microsoft should be talking about.” I was really happy that we have kind of placed
a bet there and said, “This is also what you need to be looking at from a cultural perspective
as well.” And that’s something, I think as an individual
and how I lead, that is important to me as well, so that’s why it resonated with me. COLLEEN O’BRIEN: I think that’s such a great
callout, you know, trying to roll out digital transformation without first establishing
a foundation of growth mindset, perhaps, might feel like force-fitting the future onto your
employee base. So I think that’s a really strong strategy. It’s funny that you mentioned that quantum
computing was, again, a key theme of Future Decoded. I first saw Satya talk about this at Ignite
this past fall, and sort of immediately jumped into working on Wikipedia and learning as
much about quantum computing as I could. So I really do think about these conferences
as core to my personal and professional development. How do you think about conferences as a way
you’re charting your career path and as a component to your development plan? HELEN TUPPER: I think, for me, it depends
whether they’re internal or external conferences. Something like a Microsoft Future Decoded
or a Microsoft Ready or something like that, for me, that is both me learning about what’s
going on in Microsoft, and also connecting with Microsoft people. So it serves a really strong purpose for me
in my professional development, knowledge and relationships. Conferences outside of Microsoft, I think
now in my career, I’m very selective with because there are so many. I get invited to so many marketing conferences
and technology conferences and just lots — innovation conferences, so I’m quite selective about
what I go to. I’m also quite aware of how I learn best. So I actually don’t learn best in big, big
auditoriums, I am the sort of person who learns more from interaction with people. So I would rather go to a conference where
it has an element of sort of roundtables or discussion or just go to a couple of smaller
roundtables. So for me, I’m selective both about being
specific about the thing I need to learn, but also the environment that I think I learn
best in or otherwise I just find myself sitting in a big conference and maybe getting distracted
and half doing a bit of work and half listening and thinking I’m not doing either very well. COLLEEN O’BRIEN: Yes, we’ve all been there. (Laughter.) HELEN TUPPER: I’m quite aware of that now. I’d rather spend the time wisely and get the
value out of it than sort of being some hybrid person multitasking in a room. COLLEEN O’BRIEN: Sure, and it does seem like
you’ve been very thoughtful with your development plan. You know, you have this very extensive academic
background for a bachelor’s in business management to an MBA from Henley Business School, which
I believe you’re pursuing right now. And, of course, you have a few diplomas on
innovation, creativity and leadership, and marketing in between those degrees. So can you describe your philosophy around
education and what these academic checkpoints have meant to you? HELEN TUPPER: To me, it’s not about collecting
badges. And I’m always very aware, you know, MBAs
can be badges and different degrees and masters, for me, it’s not about that. I genuinely love learning, and I think that
for careers that we’re in now and that we will continue to sort of grow in, I think
it’s all about being a work in progress, so I don’t think that the knowledge you have
now should be fixed. To kind of talk about the growth mindset stuff,
I think you need to invest in being a work in progress and continually learning and sort
of stimulating yourself. So, for me, all the things that I have learned
so far and will continue to invest time in are just about me adding to my skill set and
being stimulated by learning, being connected with other people who like learning. A big part of the MBA that I chose, I had
to do with quite a small cohort of people. It’s about 40 people. And we came together about every three months
for a couple of days and I got to learn from my peers, who worked in different industries
and had just different experience to me. So that was — my MBA was also like a side
— an outcome of that, really, what I valued was the learning environment and the dialogue
and the connection. And I think also the more interested you are
in things, I think the more interesting you are to other people. So it’s just sort of like a muscle that I
like to kind of keep strengthening and investing in what I’m learning. And as soon as I finish my MBA, I’ll start
something else. For me, it gives me a bit of perspective. I think it’s very easy to be consumed by work,
particularly you know, I have a value of achievement, I’m very driven by work, I love the jobs that
I do, and I think it’s very easy to be consumed by that. And for me, having sort of a vehicle to step
away from that and get a bit of perspective and almost slow your brain down a little bit
in terms of how you’re thinking, I find that when I come back in my job, I just have a
bit more clarity and I may be a bit more strategic and I think slightly differently than I would
if I just stayed in it day after day. COLLEEN O’BRIEN: I agree with that 100 percent. I recently completely an executive MBA program
and found that — HELEN TUPPER: Well done! COLLEEN O’BRIEN: Yeah, thank you very much. I found that it made me more productive during
the day in my work environment so that I could have that time in the evening to be more focused
in class. And we, too, had this very small group work
component to the cohort program and that’s where I also derived most of the value was
getting to really connect and build relationships with people who were in different roles at
the time, and learn from them in addition to the professors in the program. Helen, prior to working in your audience marketing
role, I know that you were an evangelist of Microsoft technologies in our Developer Experience
Division. And while your academic record is incredibly
impressive, I couldn’t help but notice that you didn’t study computer science or have
any formal technical training. So were there any gaps that you needed to
address to better connect with that developer audience? HELEN TUPPER: Yes, there were definitely gaps. So I was brought into Microsoft by a gentleman
called Liam Kelly (ph.), who was at the time the head of DX. And we sat down and we talked about the role,
I was at Virgin at the time, and I was very specific to say it sounds amazing for this
team that are working with emerging technologies and early adopters and, you know, supporting
them with testing this new technology and driving evangelism in the market. Sounded so interesting and exciting. But I very specifically called out that I
did not have the deep technical experience that other people in that team would have. And Liam wasn’t looking for that, so I felt
I was very honest in the outset about that, but you know, I also communicated that I have
this desire to learn, and I’m a relatively quick learner. And from Liam’s perspective, he actually didn’t
need another person who was deeply technical. He had a team of technical evangelists, and
the team that I manage were the audience evangelists. What he needed was the ability to take all
of that great technical work and create compelling stories and to be able to seed those stories
both within the business so the sales team can use them, and also externally so that
we could drive awareness and interest of Microsoft’s products and services. And so my role was less about doing the coding
or doing, you know, the technical evangelism, and it was more about taking that work, absolutely
having a level of understanding about it, but enough so that I could turn it into stories
that, perhaps, engaged someone who wasn’t as technical as the people doing the work,
and that was the sort of value he was getting from me and why he brought me into the role. COLLEEN O’BRIEN: And it seems like you had
a really strong foundation for that type of work given your previous experiences at Virgin
you mentioned, but also at BP, Capital One, and Proctor & Gamble. Was your career planning and your roadmap
through those companies very proactive? How did you go about identifying the experiences
that you wanted to have? HELEN TUPPER: I think of careers as being
quite “squiggly.” I think, you know, careers of yesteryear used
to be like staircases, they’re all quite linear, and you knew where you were going. And I think now careers can be very squiggly. You’re not kind of sure what your next role
is. Your next role might not even exist yet, and
I’d say in the early stages of my career, so I went from sort of FMCG into financial
services, I don’t think I was really in control of that (inaudible) if I’m honest, so that
was, you know, early 20s, didn’t really have clarity on what I was really good at, probably
didn’t really have a lot of clarity on what I wanted to do. And so I think my early career, that FMCG
to financial services kind of move, I was really sort of feeling about for what am I
good at? Where is my passion? Where do I add value? I think from that point, I’ve become much
more conscious about the choices that I’ve made. And so, you know, moving from BP to Virgin
and Microsoft, that has all been very conscious, and I have, if you like, navigated my squiggle
based on understanding about where my strengths are and how that creates value for organizations,
and also what my values are, so what really makes me happy. So it meant that, you know, go back to Liam,
when I sat down with Liam, I would talk to him about, you know, these are my values,
how do you think these would fit Microsoft? You know, I have a value around freedom and
achievement and growth and I could talk to him and say, “Are these going to be met here? What do you think?” And so as a result of the conversations that
I could have with people in those organizations, I could make those decisions about where I
wanted to go much more consciously, and it meant that, actually, I could move companies
and I could move industries, providing that my strengths were getting used to their best
effect for the organization I was going in, and providing that my values were fulfilled. So that almost became my constant, and then
I could actually have quite a lot of variety around those about where I worked. COLLEEN O’BRIEN: Got it, yeah. And I had a very similar experience. Very early in my career, I felt like I was
sort of riding a wave, but year over year, as I figure out what I don’t like and what
I do like, I’m able to get a little bit more specific about what I’m looking for next. HELEN TUPPER: And I think the skill is to
do that as quickly as possible because I think, again, to go back to the squiggle, if you
know what you’re great at and you know who can help you and you know what makes you happy,
you know, your values. You can actually — you’ve got to navigate
that squiggle. You can take an element of control over it,
but if you don’t know those things, there’s a danger, I think, you kind of bounce around
from job to job sort of looking for the answer, and I think that can feel quite demotivating. If you can take some time to sort of look
back at your jobs and say, “What did I really enjoy? Where did I have the biggest impact? What didn’t I enjoy?” And almost come up with, okay, these are my
career “must-haves,” and these are my career sort of “must-nots.” I think you can make more conscious choices
quicker. And so if anyone’s listening and thinking,
“I’m in that situation, I feel like I’m moving around trying to find the answer.” I would just say stop a minute, reflect on
the highs, the lows, when you’ve added value, and try to create that list of career “must-haves”
and “must-nots” and be a bit more conscious about the opportunities that you’re looking
at with that in mind. COLLEEN O’BRIEN: And you have a lot of experience
maintaining squiggles, career squiggles. HELEN TUPPER: Yeah. (Laughter.) COLLEEN O’BRIEN: Not only your own, but you’re
managing a team of over 20 people in the broader marketing organization. How do you go about maintaining an inclusive
environment that allows for so many people to thrive in their roles? HELEN TUPPER: For me, I think I start from
a position where I see management as a responsibility. So I’ve had great managers, and I’ve had some
more challenging managers, and I’m aware that when you don’t have a great relationship with
your manager, that is pervasive. You know, it means you don’t do as well in
your job, I think it means you go home at the end of the day and you’re talking to your
partner, your family, and it kind of affects them. So I take a real responsibility in being a
manager and I try to create teams where they are aware of each other’s strengths. So, for example, in my team meeting this week,
we all gave each other strengths-based feedback so that we could hear how other people perceived
what we were great at. I tried to create clarity and I also tried
to spend time one on one with people going through their development. So, again, not a one-size-fits-all approach,
and I will try and connect people with my connections or learning that I’ve done or,
you know, I’m trained as a coach, so I’ll try and coach them. So, for me, I think it starts from management
is a responsibility. I then kind of go down to how do I build a
cohesive team that are clear on what each of them are great at and all feel like their
work is aligned with each other. And then at an individual level, I try to
spend time with them and just relate to them personally and what they’re personally trying
to achieve, and not assume everyone’s at the same stage, or that everyone’s trying to progress
up the ladder, and just to try to sort of tailor my advice and support to them based
on what they need at that time. COLLEEN O’BRIEN: It sounds like you’re not
just checking the box on people management. You know, curating a conversation about strengths
in a team meeting requires some thought, and I think that’s really impressive. I think that’s such a great way to demonstrate
inclusion on your team. HELEN TUPPER: Thank you. It’s really important to me. COLLEEN O’BRIEN: And speaking of strengths,
we were referred to you by friend and colleague Danielle Creighton (ph.) Danielle, thank you
for the referral. She’s also working on the U.K. marketing team,
but isn’t one of your direct reports. So, personally, I thought that this spoke
volumes about how you’re communicating your brand at work to the broader organization. Do you have any strategies for building and
maintaining personal brand in the workplace? HELEN TUPPER: Yes, thank you, Danielle. (Laughter.) I don’t know if I have a really clear strategy. I think it’s kind of back to that — be really
clear about the value that you add. So I did think, when I came from Virgin to
Microsoft, at Virgin people knew — they kind of knew what Helen was, and they knew that
Helen developed people and they knew that I kind of did my job as a — you know, I used
to be head of marketing for a loyalty business for Virgin as well as kind of helping people
develop. And they knew that about me and I was kind
of aware that I was going to this new large organization where no one knew me. And I did think, “How do I get that across
to people?” And I think it’s just raising awareness of
lots of the things that I do. I have a lot of consistency about the things
that I do based on what I’m good at. So, for example, I write for a U.K. magazine
on careers and how you have happy careers. I have my venture outside of work, which is
on that. I lead teams with that, so then my teams become
aware of that. So for me, as well as being really passionate
about delivering business value, I’m really passionate about helping people have happy
careers, and I think those are the two things that I want people to know about me. I will deliver business value, and I’ll help
you to grow your business, and I will help you to grow and develop your people. And I am very consistent about the things
that I do around that. So people just become more aware of it, my
teams talk about it, there are lots of places that you can see that I do those things consistently,
and to me, it’s just about the clarity and then the consistency about what you do that
supports that. COLLEEN O’BRIEN: It sounds like you’ve been
very intentional about choosing your brand values, and then establishing this strategy
for continuing to hit on those key messages. And I’d love to dive into that. You know, you’ve referenced your coaching
here, your writing for the U.K. publication, and I know that in November of 2013, you cofounded
Amazing If, a career development and training business that helps people have happy careers. What was the driver behind your decision to
start the venture? HELEN TUPPER: You know, it’s definitely become
a venture. But at that moment, when I formed it with
my co-founder in 2013, we didn’t really have these long-term aspirations. It came from this insight that more people
were coming to us for mentoring than we had the time to mentor. And so we were having to say, “I’m sorry,”
to people, “We can’t mentor you at the moment.” And we didn’t have a solution for them to
say, you know, “I’m sorry, but go here for this advice.” And so we were talking about it, we have each
other. And what we noticed was that everybody that
was coming to us had very similar challenges. It was questions like, “I don’t know what
I’m good at. I don’t know what job I want to do next. I don’t really know what I’m great at. I don’t know who can help me. I don’t know how to plan my career.” Very similar themes that we were getting from
people. And so we decided that we’d sort of try and
do some mentoring-at-scale approach that we’d sort of take those five things that were consistently
— people were coming to us for advice about, and we’d create a 90-minute program that we
would — almost what we would speak to people individually about when we were mentoring
them. And so we went through every course we’ve
ever been on and every book we’d read, and where we thought there were gaps in things,
we created our own models. And then we just put on some courses in the
evening for people. And those courses started selling out, and
then people started trying to get us into their businesses, and then it became sort
of a podcast and it’s a book and it did scale of its own accord, and we’ve had to, at times,
kind of rein it back a little bit. Because, you know, I want to do that — for
me, it’s a side project, I want to do it alongside my job, but it’s important that I maintain
that because it’s kind of part of my motivation, also part of my personal fulfillment as well. But, yeah, it never started out as a big venture. It just started out as a way of helping more
people than we could in this one-to-one fashion have a happy career. COLLEEN O’BRIEN: Yes, it sounds like you had
this problem of scale, you couldn’t be in so many conversations at once, so had to figure
out a way to mentor multiple people in a one-to-many setting. HELEN TUPPER: Exactly that. COLLEEN O’BRIEN: And you mention that you
want to keep this as your side passion project. There’s this growing trend in the pursuit
of after-hours work or passion projects, at least here in the U.S., and I’d love to hear
if you see a similar trend in the U.K. HELEN TUPPER: Absolutely. I really do. It’s definitely a trend here as well. COLLEEN O’BRIEN: Yeah, there was this study
from Bankrate that was released this summer and it showed that 44 million people have
a “side hustle,” including one in four millennials — 25 percent of millennials are side-hustling
today. Do you consider Amazing If a side hustle? Do you prefer to call it a passion project? And how do you think that work complements
what you’re doing at Microsoft? HELEN TUPPER: So, I mean, I’d probably call
it a side project, but I don’t mind whether it’s a passion project or a side hustle. I think if you have a side hustle, I think
it needs to be a passion project because you’re doing this on the side and you’ll be using
your own time to do it. So I think you do need to have a level of
passion to make — I don’t know, that sacrifice and whatever else you’d be doing, whether
you’d be watching TV or doing sports or anything else. And I think it’s really important to do, and
I’m really excited that 25 percent of millennials are doing this because I think it’s a little
bit unrealistic to think that people are going to get all their fulfillment from their role,
and I think it is far more realistic to think, actually, people have other interests outside
of work, and actually if we can create flexible environments where people can feel that they’ve
got some time to go and explore those side projects, I think what you have as a result
is more creative employees, I think you get more loyal employees because they value the
creativity and the flexibility that you give them, and I think you — I think it’s just
a more exciting workplace because people are doing more interesting and diverse things
and they’re bringing those ideas back into the workplace, and there’s been — I’ve actually
written an article on this for marketing week in the U.K. I looked at some research that said that people
are more creative and loyal as a result of an organization letting them have a side project. For me, my particular side project is very
consistent with my job. So I think when I’m helping people, when I’m
mentoring people at scale have happy careers, it helps me come back into Microsoft and do
that with my team, and also outside of my team as well. I’ve run sessions in Microsoft on helping
people know what their values are, and that’s been outside of my direct team. So I think it helps me to become a better
leader, it keeps these things that are important to me outside of work foremost in my mind
at work, and so it makes me a more authentic leader. I’m not sort of hiding that side of myself,
I’m bringing it to work, and I’m, I think, adding value to Microsoft in a way that I
wouldn’t if I just say, “My job is a marketing director, I’ve just got to translate corp
strategy into local activation.” You know, on top of that, I’m also bringing
this thing which makes me, hopefully, more unique and add more value to Microsoft. COLLEEN O’BRIEN: You mentioned previously
your perspective on management as a responsibility to the people that you’re managing. And it just seems so thematic to me that you’re
practicing these skills of interpersonal communication in your passion project as well, that coaching
can bring so much more to your role as a people manager, and so much more experience. I think that’s really admirable. HELEN TUPPER: Well, and for me, that’s because
it’s authentic. But, actually, do you know if it was disconnected,
let’s say I was an artist, my side project was being an artist and that was potentially
disconnected, I still think there’s a lot of value in that because if that person’s
feeling they’ve got some freedom to be able to sort of unleash that creative side of themselves,
I think that then — I think that just plays back into their happiness at work with their
employees, giving them some flexibility to go and explore that. So mine is very connected, and I’ve done a
lot of work on making sure I spend my time in this consistent way, and not going to do
lots of different things. But, you know, even if it was slightly different
to my job, I still there’s value in people exploring those side projects as well. COLLEEN O’BRIEN: I agree. This podcast is very much my passion project. It’s not very related to my work as a business
manager on the Azure engineering team, but spending time working on this project gives
me a lot of fulfillment and a lot of opportunity to express myself creatively that I don’t
necessarily get on the job. So I’m showing up at work knowing that I have
that outlet instead of feeling dissatisfied because I can’t find it in that one place. HELEN TUPPER: Absolutely. I’m so passionate about side projects. I kind of want to encourage, you know, the
other 75 percent of millennials to kind of explore it even more. COLLEEN O’BRIEN: Yeah. Can you tell us about the article that you
wrote? You mentioned the U.K. publication that you’re
contributing to. HELEN TUPPER: Yes. COLLEEN O’BRIEN: Are there any other side
project trends that are of note here? HELEN TUPPER: No, I think in the article,
what I help people to do — I talked about, actually, the value of having side projects
in terms of that research that I mentioned. So I think employers sometimes can be a bit
scared of this. What does it mean? Does it mean they’re not focused on my business
enough? So I tried to present some research that said,
“Actually, embrace this, this is a really good thing, and this makes your employees
more creative, collaborative, and loyal.” So definitely embrace this. So I talked about the research. And then I talked about how people can manage
side projects. And I think it’s really important to keep
some kind of boundary around a side project. So I think if a side project does start to
become too consuming, then I think you do need to take a step back and say, “Well, I
have a job. I’m not trying to have another job.” This is something for me, this is an outlet
for me. And so in the article, I basically just talk
through how to identify what your side project could be, how to manage it. I think you should communicate your side project
to your employer. So I think if you’re having sort of like this
secret thing, it’s not really serving you very well, I don’t think it serves your employer
as well as it could be as well, and I talk about that a little bit. It will be out next month, it will be out
in December in Marketing Week. COLLEEN O’BRIEN: Excellent. And, Helen, would you mind talking to us about
some of the themes that you see in your coaching conversations? What are the conversations that you had that
prompted you and your partner to create this 90-minute program to scale those conversations? HELEN TUPPER: Yeah, it was actually very much
the ones I mentioned. So a lot of people don’t know what they want
to do. (Laughter.) I feel like they need this one single answer,
and I don’t think there is a single answer. So I think, for example, career plans are
really outdated. So if you think about a staircase, that role
that you know — sometimes at the start of our careers, they look a bit like this as
well. You spend a couple of years in one job and
then a couple of years in another and you might need to get a new qualification. In that kind of world, a career plan is potentially
quite valid. But, actually, in this squiggly world where
jobs are changing all the time and organizations are changing, and if you look at particularly
technology, there’s new technologies coming in all the time we don’t know about. You know, ten years ago you might not have
thought you’d be a manager on quantum computing. So career plans in this squiggly world, they’re
almost out of date as soon as you write them. So I talk a lot more about career possibilities,
and that was in direct response to people coming to me and saying, “I don’t know what
I want to do, there must be one single answer.” And I sort of said, “Well, unfortunately,
there’s not, but what you need to do is explore, you know, three or four career possibilities
that you might be interested in, and find out more about those, and position yourselves
for those roles in the future, rather than, you know, fixating on this one specific job
that you want.” Lots of people also came and talked about,
“Oh, I don’t know who can help me, I need to be better at networking.” A lot of people had this really strange reaction
to networking because they thought it was just about going to events and, you know,
handing out business cards, or the number of LinkedIn connections that you’ve got. But, actually, we talk about networking as
thinking more about people helping people, and that being a much more authentic way of
building your network and thinking what you have of value to give to somebody else. So maybe if your side project is, you know,
being an artist, maybe you could offer that skill to somebody else in work or out of work
or, you know, my side project’s about helping people have happy careers, maybe I can go
and help people coach, and that’s how I can help somebody. And in doing that, I build my network. You know, in doing this podcast with you now,
I’ve kind of added somebody to my network, and so that was another thing we talked about. And the third thing I think was confidence. So a lot of people that were coming to us
were really struggling with confidence — women in particular, actually. And sort of there were some very similar confidence
challenges that people were having. You know, they thought they were too young
for a job, or they thought they didn’t know enough, or they were scared of being found
out at work. And so a lot of it was helping people address
what I call “confidence gremlins.” These thoughts in your head that hold you
back at work. So they were some of the consistent themes
that we saw from people, and the program of kind of coaching that we do at scale is all
around answering those common problems. COLLEEN O’BRIEN: I do want to talk more about
the confidence gremlins and the Imposter Syndrome that you’re noting here. HELEN TUPPER: Yes. COLLEEN O’BRIEN: But just to double back to
a couple of things that you stated. I really appreciate your commentary on authentic
networking. One of the first episodes that we did on this
show was with Dona Sarkar, and she also talked about networking not as this transactional
moment, but as getting to know what the person you’re connecting with is interested in, and
supporting them on that mission. So whether it’s sending them an article about
a conversation that you had at a networking event, figuring out a way that you can create
some value in that relationship versus just that exchange of business cards. And another thing that you mentioned that
really resonated with me was the importance of accounting for technological innovation
and your career planning, however outdated that word is. That is something that really struck me when
I graduated from college and came here to Microsoft. I wanted to be very intentional about charting
my career path and reached out to a woman at LinkedIn to help me figure this out. And she said, “15-year plans don’t really
exist in this world, because 15 years ago, LinkedIn didn’t exist. So this job that I’m doing today couldn’t
be on my career roadmap.” So I just wanted to echo a few of the notes
you made here. But back to confidence gremlins, you know,
just last year, you released this book entitled How to Overcome Your Confidence Gremlins. Can you tell our listeners a little bit more
about the content of that book and, perhaps more importantly, can you flesh out this idea
of what a confidence gremlin is? HELEN TUPPER: Of course. Of course I can. So the psychology behind confidence gremlins
is actually something called “limiting beliefs,” but I think I find when I’m coaching people,
particularly millennials, you start talking about limiting beliefs in psychology, they
kind of turn off a little bit. So the concept of confidence gremlins sort
of makes it a little bit more approachable. But the principle behind it is limiting beliefs
are thoughts that we individually carry and everybody carries them, doesn’t matter how
senior you are, everyone has some kind of confidence gremlin. And it is a limiting belief that is holding
you back in some way. So it’s stopping you doing something. So let’s say that I have a confidence gremlin
around, you know, actually, let’s talk about a real one that I have. So a confidence gremlin around not knowing
enough. So I’m relatively new in my role as commercial
marketing director in Microsoft U.K., I would say as a result actually of coming into this
role new and having lots of people who know what they’re doing, I have a confidence gremlin
around not knowing enough. So that’s a limiting belief that I’m specifically
carrying around with me. That drives a certain experience for me. So the experience is that if I’m in a meeting,
for example, with some more senior members in marketing operations in the U.K., and they’re
all having a conversation, maybe as a result of my confidence gremlin of not knowing enough,
I might not speak up as much as I think I should in that meeting. So I might actually have some questions that
could be quite relevant or additive to the conversation. But in my mind, I’m thinking, “Oh, I don’t
know enough. And if I say this question, they’re going
to think I don’t know enough. And so I’m better just not saying anything
at all.” And I’ve got this internal sort of monologue
going around that, ultimately, results in the experience of me not saying anything. COLLEEN O’BRIEN: Sure. HELEN TUPPER: And that has a certain result,
and the result of that is they might think, “Oh, Helen’s onboarding quite slowly,” or,
“Helen’s not picking this up,” or “Helen’s just a bit reflective.” Whatever that is, it’s probably not the result
I want. I want them to think that I’m engaged in the
business and knowledgeable and I have ideas about how to grow it. But this, then, becomes sort of a self-fulfilling
cycle which then kind of just supports my limiting belief that I don’t know enough,
because nobody’s coming back to me and saying, “Great point, Helen, I’m really glad we had
you in that meeting.” Because I’m not saying anything. So my limiting belief of “I don’t know enough,”
it just gets reinforced and you get trapped in this negative cycle where your confidence
gremlin drives your experience, which then determines the result, and that result, then,
reinforces your belief. And it’s quite a negative thing. And within Amazing If, we saw some very common
confidence gremlins that people had, and what we try to do is just help people to — you
can’t really kill a confidence gremlin, you’ll always carry it, but what you need to do is
cage it so that it doesn’t hold you back, and then you start to — you’re more aware
of it, and you start to test it a little bit so you have slightly different experiences. COLLEEN O’BRIEN: I can see how confidence
gremlins can undermine this notion of inclusion in the workplace. Even if you’re bringing in people with different
experiences and different thought processes and different points of view, if some of them
are sort of trapped by this confidence gremlin, that undermines any work that you’ve done
to make your working group more diverse and inclusive. HELEN TUPPER: Absolutely. Actually, I think having an awareness of it
can really help. So it’s quite a big thing to be confident
in talking about it. So, you know, I’m happy to share mine because
I think, “Well, people will help me to get better.” But not everyone’s in that place, and some
people almost don’t want me to admit that thing that they fear. But the important thing about it is a lot
of this is assumptions. So a lot of people have a fear about, “I’m
too young.” For example, “I’m too young to go for that
job.” Or a lot of people have that, “I’m going to
get found out,” which is kind of the Imposter Syndrome one. And a lot of the time, that is an assumption. So you’re letting this internally held assumption
affect your experiences and affect your result without ever actually testing whether people
think, actually, are you too young? Or whether people think you are good enough. It’s just this negative thing that you’re
just kind of keeping in your mind, so I think having an awareness of it and talking to people
about it is such a powerful way of overcoming it or, you know, caging it at the least. COLLEEN O’BRIEN: You speak about a lot of
these confidence gremlins on the Amazing If podcast that you released in February. It’s a five-star show on iTunes that I really
enjoy. HELEN TUPPER: Oh, good. COLLEEN O’BRIEN: And some of the Gremlins
that you call out are fears of being found out, that Imposter Syndrome that you referenced,
to being too young, or a fear of numbers. HELEN TUPPER: Yeah. COLLEEN O’BRIEN: Why did you decide to branch
into podcasting and to take Amazing If to that medium as well? HELEN TUPPER: So Amazing If’s mission is about
helping people have happy careers and it stems from that exact same insight that we had right
back in 2013 when we started it about how do we mentor more people at scale? And our solution at the time was evening courses,
and then those evening courses started selling out. And we thought, “Well, we can’t do more evening
courses.” And so we occasionally used our holiday to
go in and help larger groups of people, but there’s only so much holiday that you can
use. And I’ve got two young children, and I want
to spend my holiday time with them as well. And so we were looking for ways to — we know
that our tools help people, we have really good feedback about that, and so we looked
at podcasts as a way of scaling again, scaling what we were doing, getting this mission to
help people have happy careers, just another way to reach a broader audience with that,
and also an international audience with it. So that’s really where that idea came from. Also, part of the reason that I do Amazing
If is because I just like creating things. And I’ve never done podcasts before, and it
was just interesting to sit in a studio and see how that whole thing happens. So, for me, it was also just something new
and interesting to do with my cofounder. COLLEEN O’BRIEN: For our listeners who might
be feeling inspired by your passion project story here, and maybe are seeking the same
fulfillment around creativity and discovery, do you have any advice for people who are
maybe looking to start their side hustle? What is the way to get started? HELEN TUPPER: I think probably two things
would be, for me, and again, based on my learning, the first is do it with somebody. And I think that is because it keeps you motivated,
and there are times when work will become so demanding that you can’t do your side hustle
that week or even that month, or you know, I’ve had two children since I started my side
hustle, so there have been quite kind of big things that have happened. And doing it with somebody else keeps your
motivation up, and it means when you’re maybe unable to contribute to it, that person can
take the reins a little bit more with it. So I found that brilliant. Also, it’s been really additive to my creativity
because I’ve been able to bounce ideas off with someone, and I’ve not felt isolated,
so I’ve always done that with that person. And we’re very aligned, you know, actually,
the person I do Amazing If with, I’ve known since university, and so we’re very close
and we have the same — kind of similar values and very similar passions. So I think if you can do it with somebody
who seems — shares the same passion for that subject that you want to do your side project
on, I think it can be really helpful to you because it is hard. You know, you do have to think about how you’re
going to fit this in. My second thing would be don’t start out with,
“It’s going to have to be perfect, and I’ve got to know exactly where I’m going to go.” I mean, I remember the first session that
we did, we didn’t know if people were going to turn up, we’d only got one session planned. We just knew we really wanted to do this and
we really wanted to do it together, and we really wanted to help people have happy careers. And so we just tested it. And we put a couple hundred pounds of our
own money behind it, and we just sort of put it out there into the world. And then we kept building it and evolving
it and we get detailed feedback after every one that we do, and we keep changing it and
we keep bringing new things into it. And I don’t have a long-term roadmap for what
Amazing If will do and where it will go. I just know that I have a very clear mission. I have someone that I love doing it with,
and I see how it helps me be better in my job, and I just want to keep that going. And so I think with your side projects, don’t
turn them into some big, strategic hurdle that you’ve got to plan every detail for,
because that’s not what they’re about. They’re about giving you energy and creativity
and helping you to apply some of your strengths in a different context, and I think if you
over-plan it or you make it too seriously, it starts taking some of the fun away from
it. You know, it’s a really big part of why you
would want to do this thing on top of other things that you’re doing in your life. COLLEEN O’BRIEN: I’ve, oftentimes, heard that
concept referred to as “imperfect action.” Taking the first step so that people can respond
to it and help you make progress. And that’s something that we really subscribe
to on this show. If you’ve listened to our first episode, it
sounds very different from where we’re at today. And that’s because creativity is a really
iterative process. So I completely agree. And, you know this notion of getting into
a side project or a passion project with someone else is something that I also — I really
recommend. Not just for someone else to pick up the slack
on the times when you’re very busy, but also to have an accountability partner. For me, that’s been very important to have
to show up for someone else and keep my commitments to something that’s not my day job. That’s been really critical. HELEN TUPPER: Myself and my cofounder, we
kind of say, “We’re more than one plus one.” There’s not just two people going at it, we
genuinely feel that our output is better when we’re together. So I add to her ideas, she adds to mine, we
create something more unique when we do it together, so I agree with you, it is more
than just the picking up the slack thing. COLLEEN O’BRIEN: Yes. And I really appreciate the content that you’re
putting out into the world, especially on that Amazing If podcast. So I highly recommend that. HELEN TUPPER: Thank you. We’re about to restart our weekly one in the
next couple of weeks. COLLEEN O’BRIEN: That’s great to hear. I’m looking forward to that. Aside from Apple Podcasts on iTunes, where
can our listeners find you on the Internet? HELEN TUPPER: Oh, they can find me — I’m
all over the place, but probably Twitter is a really easy place. So it’s just [email protected] and obviously
LinkedIn, so I share all my articles that I write for Marketing Week across Twitter
and LinkedIn. They’re probably the easiest places to find
me and kind of keep up to date with what I’m sharing. I think if you’re interested in things that
I’ve been talking about, that’s pretty much all I share on those channels is articles
that I’m reading or things that I’m writing or people I’m learning from. And so it might be a bit of a shortcut to
people also connecting with some of those ideas as well. COLLEEN O’BRIEN: Yes. I just connected with you earlier this week. I’m already getting a lot of value out of
the connection. So thank you for that. HELEN TUPPER: Absolutely a pleasure. COLLEEN O’BRIEN: Helen, thanks so much for
being on the show today, for sharing your advice, and a little bit about your career
path. Our listeners and I really appreciate it. HELEN TUPPER: My absolute pleasure. Thank you for giving me the time. (Music.) VOICEOVER: Cutting Edge, our take on stories
in the business and technology world. COLLEEN O’BRIEN: In this Cutting Edge segment,
we wanted to honor that February is Black History Month. And we decided to take a look at some recent
news at the intersection of race and technology. On February 2nd, Time reported on the new
futuristic 3D art exhibit that Google made for the National Museum of African-American
History and Culture. SONIA DARA: The exhibit showcases culturally
significant historical items, including 3D renderings of Carl Hall’s boots from The Wiz,
and a cast of composer and pianist Eubie Blake’s hand. Visitors can interact with the items and take
quizzes about them. And while the exhibit, in and of itself, is
very cool, the way it came to life is also worth noting. The installation was built by a multi-racial
team of volunteers, including members of Google’s Black Googler Network, in partnership with
other internal organizations. COLLEEN O’BRIEN: The exhibit unveiling was
preceded by the company’s new Google Doodle, which showcased the “Father of Black History,”
Carter Woodson. According to blog post written by Google Software
Engineer and Team Lead Travis McPhail, it kicked off a broader initiative at the company
to curate black cultural content across its products and services in honor of Black History
Month. SONIA DARA: I think that this infusion of
tech into a gallery space is really cool. I do appreciate the old-school museum experience
of looking and reading just as much, but being able to interact with a rendering of artifacts
that would otherwise be too fragile or maybe too priceless is such an interesting way to
bring history to life. COLLEEN O’BRIEN: Totally. And I really like that Google approached this
exhibit by looking to its internal communities, most notably the Black Googler Network. You know, as tech companies seek to build
more representative workforces and create products with truly broad appeal, it’s really
nice to see this super tactical example of the value that inclusion can provide. Google was able to curate artifacts that are
really meaningful to a shared identity group, by including more members of their internal
black community in the conversation. (Music.) COLLEEN O’BRIEN: And that’s a wrap! It was really great to catch up on the Female
Founders Alliance Champion Awards, and to learn so much from Sage about salary negotiation
and, of course, Ladies Get Paid. SONIA DARA: Ladies Get Paid. I agree. Thanks for the tip, Sage. I also really loved hearing your conversation
with Helen and hearing more about her pursuit of passion projects and her quest to cage
confidence gremlins. (Laughter.) And, of course, it was great to take some
time to catch up on the news and see how Google is honoring Black History Month in a very
tech-centric way. COLLEEN O’BRIEN: Yes. Listeners, as always, please remember to rate,
review, and subscribe to the show. All of those actions help more people find
us. And be sure to share the show, perhaps with
a manager who you think might enjoy it. As always, you can find us on Apple Podcasts,
Google Play, Spotify, YouTube, SoundCloud, or honestly, wherever you listen to podcasts. Our website is wibt.com, and if you have any
feedback or questions, please e-mail us. We’re at [email protected], or you can tweet
us @MicrosoftWomen. SONIA DARA: Your mission for this episode,
if you choose to accept it, is to write a LinkedIn recommendation for a colleague. To start, navigate to the profile of the person
you’d like to recommend. Assuming that you’re already connected to
that person, you’ll see a couple of buttons at the top of the profile. It will say “message” and “more.” You’re going to select the “more” button,
and then select “recommend.” Go through the prompts, and send the recommendation
through. Your colleague will review it before making
it visible to the public, so I oftentimes send a note offering to make any changes that
better highlight certain skills. And after that, consider asking your colleague
to return the favor and write you a recommendation. (Music.) SONIA DARA: That chocolate rush just like
— COLLEEN O’BRIEN: I know, it’s nice — (Laughter.) SONIA DARA: All right —

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