January 27, 2025 • 35 mins
In this episode of Curiosity at Work, Dr. Julie Pham interviews Cynthia Tee, SVP of Engineering at Smartsheet, to explore how curiosity drives leadership and innovation. Cynthia shares her journey from Microsoft to Smartsheet, leading a global, remote-first engineering team of over 530 people. She discusses fostering alignment, navigating mergers, and cultivating curiosity to tackle challenges and build cohesive teams. Tune in to learn how curiosity shapes decision-making, teamwork, and growth in the tech industry.
Connect with Dr. Julie Pham:
- LinkedIn:https://www.linkedin.com/in/juliepham2/
- Website:https://curiositybased.com/
- Instagram:https://www.instagram.com/juliephamphd/
Connect with Cynthia Tee:
- LinkedIn: https://www.linkedin.com/in/cynthiatee
#CynthiaTee #Smartsheet #CuriosityAtWork #EngineeringLeadership #RemoteWork #Innovation #TeamCollaboration #Leadership #ContinuousLearning
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Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
(00:04):
I'm Dr. Julie Pham, founder of Curiosity Based.
We help people practice curiosity in the world, starting in the workplace, because that is where we spend most of our waking hours.
Curiosity as a practice boils down to self-awareness, relationship building, and clear communication.
So join us as we interview leaders to see how they use curiosity at work.
Hi, welcome to the Curiosity at Work podcast.
(00:27):
I'm Julie Pham, and today I get to be having a conversation with Cynthia Tee, who is the SVP of engineering at Smartsheet.
And Cynthia's had a long career in the tech industry, heading engineering at Nordstrom, Microsoft.
When I met her, Cynthia was actually the head of Ada Developers Academy, so helping people get into engineering, software engineering, so also has non-profit experience as well.
(00:56):
Cynthia, I'm looking forward to this conversation.
Welcome.
Thank you for having me here, Julie.
I'm also really looking forward to this conversation.
So Cynthia, you have been an engineering leader for years.
Can you just share right now what your current role is?
How many people are in your department?
(01:17):
How they work remotely or in person?
Are they in one office or around the world, if you could share?
Yes, yes.
So I'm head of engineering at Smartsheet.
I support all 530 or so engineers that we have at Smartsheet today, and we are a remote-first company.
(01:40):
So that means that I have engineers all over the world, actually, but in the continental United States alone, that's where the company started.
So we have hired all across the country, and we also have engineers in the UK as well as Australia, and those are part of acquisitions that the company has done over time.
(02:06):
And I will say that being a remote-first company, we have really thrived, you know, leveraging the fact that we are around the world, leveraging our product, actually, which is a work management, collaborative work management product that we constantly use in order to get things done asynchronously.
(02:27):
So we have definitely, as an engineering org, walked away from needing a space.
We do still have spaces, and so, you know, where I think in a pre-COVID world, we would call them off-sites, we now say on-sites, you know, so we do meet and work in person occasionally.
(02:49):
And so we are actually a curiosity base.
We use Smartsheet too to help us with our management.
So how many offices do you have around the world then?
Yeah, so we have a base office in Bellevue.
We also have an office in Costa Rica, although we don't have engineers in Costa Rica, but other disciplines at Smartsheet also have offices in Costa Rica.
(03:17):
We have a base office in Sydney, Australia, although my engineers are actually based mostly out of Brisbane, a couple of them.
Well, they basically work all over the continent because we hire all over the continent now.
And then also an office in Sydney, as well as also Boston.
In the United States, we have Bellevue and Boston and London.
(03:39):
So do you also have regional engineering managers or is it just more by function?
We do.
We do have, well, we have, I would say some of the sites do have site leaders, especially I think when you're growing the site from the ground up, you do tend to have somebody who's a site leader.
And more often than not, they basically are from a certain particular function, right?
(04:04):
And so as the site gets bigger and as the various teams build, they basically gravitate more to running that particular function.
So we acquired a company out of Edinburgh.
Our leader there is, you know, basically lives in Scotland and works out of Scotland and manages all the engineers that are in the UK.
(04:27):
And so you actually said a lot of the engineers you were able to get through acquisitions with companies.
The ones that are outside the United States.
And we actually did also acquisitions within the United States.
We acquired a company called 10,000 Feet that was actually based in Seattle.
(04:48):
Another one called Brandfolder that used to be based in Denver.
But after we've acquired them, they've also, you know, we've intermingled and cross-pollinated our folks and they've also started to hire across country.
So yeah, we're pretty spread out now.
It would actually be interesting to understand what happens when you're merging or bringing in from different work cultures and how does that, how do you work with that, especially around fostering curiosity?
(05:20):
Because then there's the curiosity of one another too.
And there's always that hesitation.
And so I'd love for you, as we talk about how you help people practice curiosity in the workplace, if you could bring that up, that acquisition part.
So yeah.
Yeah, for sure.
I will.
Cynthia, we think of curiosity as a practice and sometimes we do it, sometimes we don't do it sometimes because it's really, really hard.
(05:44):
Could you talk about when it has been difficult for you to practice curiosity at work?
I think the hardest moments for me to practice curiosity are when I feel hurt or angry by what somebody has said or offended in some manner, right?
Either because it's something I feel I should know a lot about or, you know, wasn't my intention to begin with or I feel attacked or taken aback or anything like that.
(06:18):
And I think in those moments you feel like reacting very, very strongly and those are, or responding, right?
You feel your integrity is questioned or your team's integrity is questioned.
So you feel like responding right away.
And those are, for me, the toughest times to actually practice curiosity.
And does that come up when you are seeing functional differences where it's just, hey, maybe the person who is hurting you, it's just there's a functional misunderstanding or is it a personality misunderstanding or when does that usually come up?
(06:54):
Oh, it's all of the above, right?
I will say that most of the time people don't mean to say hurtful things or offensive things.
It's just, you know, sometimes it's a result of misalignment of expectations or a situation where you're communicating bad news or news that they didn't expect, right?
(07:14):
Or just commentary and opinion or a difference of opinion that you didn't expect.
I don't think it's common for people to offend on purpose, but sometimes it actually comes out offensive, you know?
So I think those are the times where it's really, really hard to kind of just step back.
(07:39):
But I've found it is extremely important, not only for you as a leader to bring your temperature down some, but also for your own interpretation to be curious.
Why does the person feel this way?
Why are they surprised when you didn't expect them to surprise?
(08:01):
Why do they disagree with you?
And why do they feel the way they do?
And maybe you interpreted something that they didn't actually quite intend.
And so, you know, I actually think it is extremely helpful in those, especially in those times, to be curious, to ask questions, right?
Not only to buy time, but to also, I can't tell you how many times I actually misunderstood somebody and was so thankful that instead of reacting right away, that I actually took the time to realize that I misunderstood something and to steer the conversation in a different direction.
(08:39):
Mm-hmm.
I'm thinking about when you were at, I'm going to assume, you can tell me if I'm wrong, when you were at Nordstrom, I'm assuming that the engineers were probably not through that acquisition of these different global offices.
And now you're at Smartsheet where so much of that engineer, the engineers come together from these different workplaces and they're coming together and also different regions, even just Pacific Northwest versus Boston, Australia versus England.
(09:06):
And so how much of that, if you could compare, I guess, that misunderstanding, how much of that is coming from the changes?
Yeah.
You know, a lot of it for me when, and I'm on the side of the fence where I'm part of the company that it's acquiring another company, right?
(09:27):
And I think that, and I've been on the other side too in past lives.
I think it's very difficult for people to understand all of the cultural things and all the protocol of their acquiring company, right?
It's very difficult for them to understand sometimes what's expected.
And it's very natural for them to form a narrative around how things are working, right?
(09:52):
And so I think it's super important to really give a lot of space to learn more about the companies that are coming in and make it feel more like you're learning from each other as opposed to one taking over the other, right?
So for me, it's a practice of, I always start by saying Smartsheet is a culture of alignment where we use our product to align people, right?
(10:19):
And that is something, a baseline that I always start with.
So I like to be curious about the people who have just joined the company to learn more about them and to learn more about what they've accomplished and how, what they think has worked well.
And then also what they're concerned about, right?
(10:39):
What were their fears but also what they feel really proud of.
And I think when you role model that, they also naturally, you know, hopefully get curious about the company so that they can also find out what they've assumed maybe incorrectly and, you know, what they should know also, so.
(11:00):
So you mentioned, you just mentioned that you have been on that other end where you're part of the company that was getting acquired.
I assume that was when you were at PlayFab and then that was acquired by Microsoft.
So did that experience inform how you now as Smartsheet being the acquiring company affect how you want to do that transition?
(11:22):
Yeah, absolutely.
Absolutely.
And even when I was at Microsoft, I have seen acquisitions that have gone very poorly.
I think it was extremely valuable for me to have the experience that I did where I've worked in a big corporation and I've worked in a really tiny one and I've worked in a nonprofit.
And then now I work in sort of, I would say sort of a midsize company, right?
(11:43):
So I think it's super valuable to put yourself in different situations as a leader, not only to build empathy, but to also just build your knowledge about what are some of the things that people might at first be concerned about or where you would apply your leadership first.
(12:06):
Could you give some very tactical tips on if someone said, hey, we're about to merge these two companies and how much time should we set aside for transition?
Because I think oftentimes people want it to happen very fast.
And so realistically, how much time should you set aside for that transition period?
(12:27):
And what are some things that you've learned that are, hey, we should do these things or we should have these conversations to make sure that the transition goes as smoothly as possible with the understanding that all transitions are bumpy?
Yeah, you know, before an acquisition actually happens, you have a period of time where you do a lot of due diligence, right?
(12:49):
On all angles for the company.
So if you are the one acquiring a company, you basically have like all these questions and documents that you need to find out more that often requires meeting face-to-face with certain individuals in the company.
In my situation, where it's very focused on engineering, you basically ask a lot about their architecture, their capabilities, how they scale, what they do about security, privacy, all that sort of thing.
(13:17):
And you also ask about the team.
I think it's really important to ask about and learn about people, the people that are actually there.
So I think that is a very important part of it, was when you are on the side of the equation, understanding more about who you're going to acquire, that you do a really great job trying to understand everything about them, right?
(13:42):
And then once you go through that transition, I think you enter that with a really strong knowledge base about the leaders in the company and who are the people that you really want to count on and bet on to help lead this transition and really spend the time to get to know them better and to get to know the people better.
(14:06):
And then I also think you have to ask yourself, what are the goals that we currently want to accomplish?
And given that, what's the right organizational structure that we need to blend this organization into?
What are the right seats at the table that we need to have with the folks that we're bringing in?
(14:26):
And how can we have them operate with the same responsibilities that their equivalent would have over here, right?
You have to be very realistic.
I think people want to, you know, it's very common, I think, for when you acquire a company, you don't want to immediately integrate everything, and you're just like, it's not realistic to do that.
(14:49):
Things take time.
So it's a question of being very intentional about recognizing your priorities, their priorities, and how you want to basically unify those over time, right?
I think a very strong relationship with the leaders at different levels, peer relationships, is super important.
(15:10):
I also think that I've learned that it's super powerful to cross-pollinate people and make them really part of the organization.
So I've had approaches where we treat an organization completely separate, and we think that's the best way to start, but that just reinforces different ways of doing everything, right?
(15:32):
Decision making, the way you sell the product, the way you position the product, your engineering priorities, your approach to good design.
Whereas if you find the right starting point for a blend, I think it is actually more successful.
And I think when you start to cross-pollinate people, it actually really, really helps.
(15:53):
So, you know, with all the variations that I've learned, those are probably the more respectful thing.
It actually does encourage curiosity, right?
If I were to go lead an organization that's entirely different from what I'm used to, then I, as a leader, you know, I would send somebody in with a high amount of curiosity that wants to learn more about what the team needs from them, right?
(16:19):
So.
Yeah.
So I hadn't thought about what you said before the acquisition.
There's actually this long period of discovery and understanding.
And so aside from the technical questions, what's one or two favorite questions that you like to ask?
Because you said that you like to ask of the people.
And I'm assuming that you're asking the other engineering leaders to represent, to talk about their engineering team.
(16:45):
So what are just some favorite questions you like to get at to understand?
Yeah, I like to find out more about the person themselves, their own journey, where they came from, what they value as a leader, what are they proud of doing as part of the organization, and what's important to them, what they think is important to the team.
(17:08):
And then, you know, I like to also be open with the team, get to know the team and spend time with the team.
And so when we did our acquisitions, we actually, you know, actually spent time, like we actually flew over to those sites and, and spent a good amount of time with them, in addition to having some of those folks come over here and get to know us.
(17:30):
So I think the two-way curiosity is really important.
I think being open to questions is important.
And I think getting to know people at an individual level, as well as from a leadership point of view, what they think is important for their teams and themselves is also super important.
(17:52):
So just from a, I'm an outsider, I'm just part of the public, I hear about these mergers that come together.
How much time do you, how much time does the average employee actually get to know about that there might be a merger before the merger happens?
Because I always assumed it just happened, and then you're informed, oh, we have been acquired by this company, and now we're coming together.
(18:12):
But it's, it sounds like there's actually a period where they do get to know each other.
Of the acquisition, right?
I mean, if it's a smaller company, then it doesn't, it doesn't have to take that long.
And sometimes if it's bigger, it just the financial transactions behind that take a long time, or have to be approved by somebody else or whatever.
(18:35):
But I think it just depends on the size and the nature of an acquisition.
But there is a period before the acquisition where they can actually come together, not at the leadership level, but just your rank and file.
Usually it gets before the actual acquisition.
(18:56):
I mean, if you're talking about a startup of 10 people, like, really, you're probably interacting with most of them.
And you have to find out the information that you do.
Like, you're interacting with most of them.
But if, but if it's a, if it's a company of about 100 people, like there's, there's a certain set of people that you tend to concentrate on interacting with.
(19:16):
Okay, great.
And, and then I appreciate what you said about one of the things you, where it's hard is if you keep that new company, the acquired company separate, and so that cross-pollination as soon as possible to create that integration.
What's the, I mean, in your experience, what have you seen as, oh, this is, we, how long did it take to feel, okay, we are truly integrated?
(19:47):
Was it three months, six months, a year, two years for it to feel like, wow, we're, we're integrated?
I think it's probably, I mean, again, it's very situational.
I think it depends on the size of the company, but I think it, you can expect it to happen any less than six months, at least, right?
And sometimes it could take to a year.
(20:09):
I think you also have to realize that the, that the reason that you acquired a company, right, is not just, I mean, there's certain goals that you had, right, to acquire that company that made financial sense for a decision to be made.
And I think that you, it takes some time.
(20:30):
And for some people in that company that you're acquiring, it, they also have to think about their own future and whether they buy in or are, or value the, the, the values that you have, right?
And so I think it is inevitable sometimes that some people will discover after a couple of months that, hey, you know, I want to go personally in a different direction, right?
(20:56):
And that's, that's perfectly fine also.
And then some people who are like, oh my gosh, this is great.
You know, I, this is totally for me.
So I think individuals take their own time and you have to recognize who those are and give them that time and space, but also make expectations clear.
I don't think there's any formula for this.
(21:19):
I, I really, like, I will tell you that I prefer some sort of cross-pollination right away, but I really, really think it's very situational, right?
So I'm not going to say that what, what we're doing with the smaller acquisitions we've made is the same formula you should use, like whatever Microsoft decided to do with LinkedIn.
(21:40):
It's just very situational.
Well, thank you for sharing your experience then.
Now moving on to the next question is what do you, what do you do for engineers in particular to help cultivate curiosity on your engineering teams?
(22:00):
Most of the time, I find, I will say the general people in tech, when they don't exercise curiosity, it's for two reasons.
One, pride, because they think that they know a whole lot of stuff, not from a unintentional place, but they're paid to be experts somewhat.
They're paid to know what they're doing.
So I think it comes from a place of, oh, I think I know everything because I've actually put in the hard work to know everything and I keep up with everything.
(22:29):
And so this is where I'm at.
And two, determination and impatience, right?
And so I need to get this done.
I got to go get it done.
So I'm just going to go, like I'm going to go and I'm not going to look back.
And, and again, I think that they always say like your strengths are sometimes your weaknesses.
(22:49):
So I often see, think that when I see this behavior, sometimes it's actually doesn't come from a bad place.
It's just a lot of combination of determination and grit.
And like, I think I know this because I've spent a heck of a lot of time figuring it out.
So my, my take is, is always that when you are trying to make a decision of some kind, you need to understand like who owns that decision in the end and who are the key stakeholders of that decision.
(23:21):
And once you decide that very intentionally, you do have to be curious with those key stakeholders.
And hopefully those key stakeholders will be curious about you, right?
So I, I can't tell you how many times I've been very convinced that what I'm about to do is the right thing.
And then when I actually talk to somebody, I'm like, oh, I should factor that in.
(23:43):
I didn't realize it.
And it has nothing to do with how brilliant I am or not brilliant I am.
And this has everything to do with how you, how you steer an organization and how you eventually do the right thing, I think is a, is a combination of how you make sure you compensate for your own blind spots as a leader.
(24:07):
Because we all have them.
Yeah.
It reminds me of what you were just saying about the bringing together different cultures.
It depends on the situation.
And so one way to slow that down, because I know with engineers, it's solve the problem, solve the problem, solve the problem and outcomes, outcomes, outcomes.
And yet to slow it down, it's good.
Wait, who are the stakeholders in this situation?
(24:29):
Okay.
If we look at that, then I mean.
I feel like we have this culture of you try it, you fail, you learn, you, you kind of try it.
Right.
And so sometimes curiosity gets reenacted that way.
And sometimes the situation is, is very appropriate to be done that way.
Too much questioning also gets you to a place where you wait for too long to make any decision.
(24:49):
Right.
So I think it's a, it's a healthy balance.
Either curiosity, because you are very, I think the important common thing is you are very extremely self-aware.
You understand the risks you're taking.
You understand your blind spots.
You understand the strengths of a technology, the weaknesses of a technology.
Right.
And so you have to remain curious about where you could have possibly gone wrong.
(25:14):
What could you possibly do better the next time?
Maybe somebody has a better idea.
You can do that even while you're doing things, even while you're building software.
Right.
You don't have to like wait and stop the presses.
So, and just depending on some of the decision, sometimes you do have to wait.
Sometimes you do have to process a lot of different levers and inputs because the investment is so large.
(25:40):
Right.
So I, I think it, it's again, very situational, but I think it starts from a place of self-awareness, full awareness of the people in the situation.
And also like really intentional, who makes this decision, who are the key stakeholders who need to align.
(26:00):
Cynthia, since you've been at companies of different stages, different sizes, different stages, do you see a difference in the analysis paralysis?
We're just going to keep asking questions versus, Hey, let's just try it, break it, keep moving on.
Do you, or is it more of just the particular company leadership?
Does the stage have anything to do with how much willingness to just try and break versus asking a lot of questions to make sure it's right?
(26:29):
Yeah.
I think the more customers you have on the line, the scarier it inevitably is.
Right.
You do, you do need to just take a look at it and make sure that you're doing the right thing.
It will move faster as long as you are more self-aware and have the right people involved.
Right.
So again, that you are examining your risks and you are very intentionally looking at pros and cons and very aware of yourself as a leader, your blind spots and compensating for that with who you bring into the fold in terms of making any decision.
(27:07):
Often I find that when you have less customers or when you're still experimenting, yeah, you can move a lot faster and learn by failing.
When you have larger customers at stake, it's a little tougher to do that.
Thank you.
I hadn't thought about that before, but that makes a lot of sense.
How many customers you have and probably also how many, how much support those customers have because a lot of Smartsheet's customers are small businesses who might not have these robust IT teams versus if you're serving a lot of institutional clients who, I mean, there's even just the, the needs of your particular clients too, I can imagine plays into that.
(27:46):
Yeah.
You know, I think there's a difference between having software that's used by a small set of people and one that's used by large enterprises.
Right.
And, and you, you inevitably have to be careful when you are used by large customers and your software happens to be really at the center of what they do.
(28:09):
Cynthia, with all of this, with all of these different remote first, the different engineers, what is your favorite question or way to recruit for curiosity for engineers?
Um, I always liked to ask the question of, can you tell me about a time where you made a mistake and tell me what the process was, what was your decision-making process, what got you there?
(28:42):
And then when did you realize you made a mistake?
What did that teach you?
And then what did you do about it?
Um, and I think the people that I really, it's okay for people to think really hard before they answer that question, but usually the people that do do, they've thought about it so much that it's actually not hard for them to give me a very meaningful example, very, very meaningful example.
(29:12):
And for me, I value that because I feel like they are always questioning whether they've covered their bases, whether they've considered everything and yet still are making progress.
Right.
So they know how to balance that.
And so, um, I think curiosity is really the same as that.
You know, that's how you learn.
(29:33):
That's how you grow yourself.
Right.
Um, I think that in this world of AI, I will say that curiosity is especially important because we read a lot about it.
Right.
But I'm, I'm just like, have you used it?
Have you used it?
Right.
And what is it?
(29:53):
The more you use it, you realize here's where it actually is for whatever your job function is.
Here's what it does well.
Here's where I can still add value.
And here's what it doesn't do so well.
And by the way, that may change next month.
Right.
Um, but here's how I can actually use it to be faster and more effective at my job.
Hmm.
(30:13):
This is going to replace my job because I know a lot of people just rather than the fear, like, I think there is a healthy amount of fear, which I think is, is good.
But I, I think you should also ask yourself what you're going to do about it and what you can do with it.
So, yes.
And I, I like asking that question too, of talk about a mistake, because I'm always, I'm always weary of people who are just, Oh, I've made lots of mistakes, but I can't think of one right now.
(30:42):
Yeah, exactly.
At that point I'm like, well, you were probably not curious enough about yourself and your own and your own learning.
Right.
Um, so how can I expect you to be curious about other people?
So Cynthia, what is inspiring curiosity for you in your own life right now?
(31:03):
So many things.
I think, I think the best part about being an engineer is that things are constantly changing new technologies disrupt our lives.
Um, you know, as a leader of a large organization, I am always curious about leadership itself, right?
(31:24):
How you make decisions, how you can make them better.
Who do you surround yourself with?
Um, am I constantly still learning as a leader?
Am I learning from the people around me?
I like to surround myself with people that I am constantly learning from.
Um, so I, that's why, you know, for me, I have a really strong preference for the size of the company Smartsheet is because it's not too small, but it's not so big that I don't feel like I have an impact on where the company's direction is.
(31:58):
But, um, I feel Smartsheet basically perfect in terms of the size that it is the role that I have.
Um, and the people that I work with, uh, you know, um, so I, I, um, I, I get curious a lot and I get pushed to be curious a lot by my peers.
That's probably one reason I love it.
(32:20):
Because I have a lot of peers.
I have people who will question me, not hesitate to question me.
And that's, that's frankly how I grow.
That's frankly, how I get pushed to also continue being even more curious than, than maybe I was.
So.
And are you referring to the peers that you have in outside of your department, then outside of engineering?
(32:42):
All of it.
Like my, my peers across the company, but also my direct reports and my people managers, I learn a lot from them.
Right.
And I think in part, um, um, I am always, I always strive to have them challenge me or have them ask me questions.
(33:03):
Um, and if I can't answer it, I'm like, I've gone well beyond this point where I have to answer every single thing.
So I'm just not, I'm just not going to do that.
Right.
So I always like to say, here's my hypothesis.
Here's where I stand, but, you know, let me know if you strongly disagree, or if you think I should move in a different direction, um, give me your input.
(33:28):
Um, and I, I'm very clear when it is actually my decision in the end, but I will listen to people and I will explain where my head is at.
So being inspired by your colleagues, that's great.
Yeah.
Cynthia, thank you so much for sharing your insights on how you foster curiosity at work with software engineers at a tech company.
(33:50):
Really appreciate what you shared today.
And I know that our listeners are going to be able to apply it to whatever field that they're working in.
Yeah.
Yeah.
Thank you.
Thank you for having me here.
Um, I have a book recommendation.
Oh yes.
There's a very lovely book that I think really is fundamentally all about why you should be curious.
(34:13):
And it's called Think Again.
And I think that it is a perfect, like, if you read everything in there, it really is about how people should be curious because sometimes that actually saves their lives, saves a company, or leads you to a better outcome in the most unexpected places and times.
(34:36):
So, um, I have really internalized a lot of what that book has been talking about, and I really encourage people to read it because that for me is classic, like, why you should be curious.
That's the book by Adam Grant, I believe.
Yes.
Okay, great.
Yeah.
I enjoyed that book too.
Yeah.
Cynthia, thank you so much for being on the Curiosity at Work podcast.
(35:00):
Thank you so much, Julie, for having me here.
I'm Dr. Julie Pham, founder of Curiosity Based.
We help people practice curiosity in the world, starting in the workplace, because that is where we spend most of our waking hours.
Curiosity as a practice boils down to self-awareness, relationship building, and clear communication.
So join us as we interview leaders to see how they use curiosity at work.
Hi, welcome to the Curiosity at Work podcast.
(00:27):
I'm Julie Pham, and today I get to be having a conversation with Cynthia Tee, who is the SVP of engineering at Smartsheet.
And Cynthia's had a long career in the tech industry, heading engineering at Nordstrom, Microsoft.
When I met her, Cynthia was actually the head of Ada Developers Academy, so helping people get into engineering, software engineering, so also has non-profit experience as well.
(00:56):
Cynthia, I'm looking forward to this conversation.
Welcome.
Thank you for having me here, Julie.
I'm also really looking forward to this conversation.
So Cynthia, you have been an engineering leader for years.
Can you just share right now what your current role is?
How many people are in your department?
(01:17):
How they work remotely or in person?
Are they in one office or around the world, if you could share?
Yes, yes.
So I'm head of engineering at Smartsheet.
I support all 530 or so engineers that we have at Smartsheet today, and we are a remote-first company.
(01:40):
So that means that I have engineers all over the world, actually, but in the continental United States alone, that's where the company started.
So we have hired all across the country, and we also have engineers in the UK as well as Australia, and those are part of acquisitions that the company has done over time.
(02:06):
And I will say that being a remote-first company, we have really thrived, you know, leveraging the fact that we are around the world, leveraging our product, actually, which is a work management, collaborative work management product that we constantly use in order to get things done asynchronously.
(02:27):
So we have definitely, as an engineering org, walked away from needing a space.
We do still have spaces, and so, you know, where I think in a pre-COVID world, we would call them off-sites, we now say on-sites, you know, so we do meet and work in person occasionally.
(02:49):
And so we are actually a curiosity base.
We use Smartsheet too to help us with our management.
So how many offices do you have around the world then?
Yeah, so we have a base office in Bellevue.
We also have an office in Costa Rica, although we don't have engineers in Costa Rica, but other disciplines at Smartsheet also have offices in Costa Rica.
(03:17):
We have a base office in Sydney, Australia, although my engineers are actually based mostly out of Brisbane, a couple of them.
Well, they basically work all over the continent because we hire all over the continent now.
And then also an office in Sydney, as well as also Boston.
In the United States, we have Bellevue and Boston and London.
(03:39):
So do you also have regional engineering managers or is it just more by function?
We do.
We do have, well, we have, I would say some of the sites do have site leaders, especially I think when you're growing the site from the ground up, you do tend to have somebody who's a site leader.
And more often than not, they basically are from a certain particular function, right?
(04:04):
And so as the site gets bigger and as the various teams build, they basically gravitate more to running that particular function.
So we acquired a company out of Edinburgh.
Our leader there is, you know, basically lives in Scotland and works out of Scotland and manages all the engineers that are in the UK.
(04:27):
And so you actually said a lot of the engineers you were able to get through acquisitions with companies.
The ones that are outside the United States.
And we actually did also acquisitions within the United States.
We acquired a company called 10,000 Feet that was actually based in Seattle.
(04:48):
Another one called Brandfolder that used to be based in Denver.
But after we've acquired them, they've also, you know, we've intermingled and cross-pollinated our folks and they've also started to hire across country.
So yeah, we're pretty spread out now.
It would actually be interesting to understand what happens when you're merging or bringing in from different work cultures and how does that, how do you work with that, especially around fostering curiosity?
(05:20):
Because then there's the curiosity of one another too.
And there's always that hesitation.
And so I'd love for you, as we talk about how you help people practice curiosity in the workplace, if you could bring that up, that acquisition part.
So yeah.
Yeah, for sure.
I will.
Cynthia, we think of curiosity as a practice and sometimes we do it, sometimes we don't do it sometimes because it's really, really hard.
(05:44):
Could you talk about when it has been difficult for you to practice curiosity at work?
I think the hardest moments for me to practice curiosity are when I feel hurt or angry by what somebody has said or offended in some manner, right?
Either because it's something I feel I should know a lot about or, you know, wasn't my intention to begin with or I feel attacked or taken aback or anything like that.
(06:18):
And I think in those moments you feel like reacting very, very strongly and those are, or responding, right?
You feel your integrity is questioned or your team's integrity is questioned.
So you feel like responding right away.
And those are, for me, the toughest times to actually practice curiosity.
And does that come up when you are seeing functional differences where it's just, hey, maybe the person who is hurting you, it's just there's a functional misunderstanding or is it a personality misunderstanding or when does that usually come up?
(06:54):
Oh, it's all of the above, right?
I will say that most of the time people don't mean to say hurtful things or offensive things.
It's just, you know, sometimes it's a result of misalignment of expectations or a situation where you're communicating bad news or news that they didn't expect, right?
(07:14):
Or just commentary and opinion or a difference of opinion that you didn't expect.
I don't think it's common for people to offend on purpose, but sometimes it actually comes out offensive, you know?
So I think those are the times where it's really, really hard to kind of just step back.
(07:39):
But I've found it is extremely important, not only for you as a leader to bring your temperature down some, but also for your own interpretation to be curious.
Why does the person feel this way?
Why are they surprised when you didn't expect them to surprise?
(08:01):
Why do they disagree with you?
And why do they feel the way they do?
And maybe you interpreted something that they didn't actually quite intend.
And so, you know, I actually think it is extremely helpful in those, especially in those times, to be curious, to ask questions, right?
Not only to buy time, but to also, I can't tell you how many times I actually misunderstood somebody and was so thankful that instead of reacting right away, that I actually took the time to realize that I misunderstood something and to steer the conversation in a different direction.
(08:39):
Mm-hmm.
I'm thinking about when you were at, I'm going to assume, you can tell me if I'm wrong, when you were at Nordstrom, I'm assuming that the engineers were probably not through that acquisition of these different global offices.
And now you're at Smartsheet where so much of that engineer, the engineers come together from these different workplaces and they're coming together and also different regions, even just Pacific Northwest versus Boston, Australia versus England.
(09:06):
And so how much of that, if you could compare, I guess, that misunderstanding, how much of that is coming from the changes?
Yeah.
You know, a lot of it for me when, and I'm on the side of the fence where I'm part of the company that it's acquiring another company, right?
(09:27):
And I think that, and I've been on the other side too in past lives.
I think it's very difficult for people to understand all of the cultural things and all the protocol of their acquiring company, right?
It's very difficult for them to understand sometimes what's expected.
And it's very natural for them to form a narrative around how things are working, right?
(09:52):
And so I think it's super important to really give a lot of space to learn more about the companies that are coming in and make it feel more like you're learning from each other as opposed to one taking over the other, right?
So for me, it's a practice of, I always start by saying Smartsheet is a culture of alignment where we use our product to align people, right?
(10:19):
And that is something, a baseline that I always start with.
So I like to be curious about the people who have just joined the company to learn more about them and to learn more about what they've accomplished and how, what they think has worked well.
And then also what they're concerned about, right?
(10:39):
What were their fears but also what they feel really proud of.
And I think when you role model that, they also naturally, you know, hopefully get curious about the company so that they can also find out what they've assumed maybe incorrectly and, you know, what they should know also, so.
(11:00):
So you mentioned, you just mentioned that you have been on that other end where you're part of the company that was getting acquired.
I assume that was when you were at PlayFab and then that was acquired by Microsoft.
So did that experience inform how you now as Smartsheet being the acquiring company affect how you want to do that transition?
(11:22):
Yeah, absolutely.
Absolutely.
And even when I was at Microsoft, I have seen acquisitions that have gone very poorly.
I think it was extremely valuable for me to have the experience that I did where I've worked in a big corporation and I've worked in a really tiny one and I've worked in a nonprofit.
And then now I work in sort of, I would say sort of a midsize company, right?
(11:43):
So I think it's super valuable to put yourself in different situations as a leader, not only to build empathy, but to also just build your knowledge about what are some of the things that people might at first be concerned about or where you would apply your leadership first.
(12:06):
Could you give some very tactical tips on if someone said, hey, we're about to merge these two companies and how much time should we set aside for transition?
Because I think oftentimes people want it to happen very fast.
And so realistically, how much time should you set aside for that transition period?
(12:27):
And what are some things that you've learned that are, hey, we should do these things or we should have these conversations to make sure that the transition goes as smoothly as possible with the understanding that all transitions are bumpy?
Yeah, you know, before an acquisition actually happens, you have a period of time where you do a lot of due diligence, right?
(12:49):
On all angles for the company.
So if you are the one acquiring a company, you basically have like all these questions and documents that you need to find out more that often requires meeting face-to-face with certain individuals in the company.
In my situation, where it's very focused on engineering, you basically ask a lot about their architecture, their capabilities, how they scale, what they do about security, privacy, all that sort of thing.
(13:17):
And you also ask about the team.
I think it's really important to ask about and learn about people, the people that are actually there.
So I think that is a very important part of it, was when you are on the side of the equation, understanding more about who you're going to acquire, that you do a really great job trying to understand everything about them, right?
(13:42):
And then once you go through that transition, I think you enter that with a really strong knowledge base about the leaders in the company and who are the people that you really want to count on and bet on to help lead this transition and really spend the time to get to know them better and to get to know the people better.
(14:06):
And then I also think you have to ask yourself, what are the goals that we currently want to accomplish?
And given that, what's the right organizational structure that we need to blend this organization into?
What are the right seats at the table that we need to have with the folks that we're bringing in?
(14:26):
And how can we have them operate with the same responsibilities that their equivalent would have over here, right?
You have to be very realistic.
I think people want to, you know, it's very common, I think, for when you acquire a company, you don't want to immediately integrate everything, and you're just like, it's not realistic to do that.
(14:49):
Things take time.
So it's a question of being very intentional about recognizing your priorities, their priorities, and how you want to basically unify those over time, right?
I think a very strong relationship with the leaders at different levels, peer relationships, is super important.
(15:10):
I also think that I've learned that it's super powerful to cross-pollinate people and make them really part of the organization.
So I've had approaches where we treat an organization completely separate, and we think that's the best way to start, but that just reinforces different ways of doing everything, right?
(15:32):
Decision making, the way you sell the product, the way you position the product, your engineering priorities, your approach to good design.
Whereas if you find the right starting point for a blend, I think it is actually more successful.
And I think when you start to cross-pollinate people, it actually really, really helps.
(15:53):
So, you know, with all the variations that I've learned, those are probably the more respectful thing.
It actually does encourage curiosity, right?
If I were to go lead an organization that's entirely different from what I'm used to, then I, as a leader, you know, I would send somebody in with a high amount of curiosity that wants to learn more about what the team needs from them, right?
(16:19):
So.
Yeah.
So I hadn't thought about what you said before the acquisition.
There's actually this long period of discovery and understanding.
And so aside from the technical questions, what's one or two favorite questions that you like to ask?
Because you said that you like to ask of the people.
And I'm assuming that you're asking the other engineering leaders to represent, to talk about their engineering team.
(16:45):
So what are just some favorite questions you like to get at to understand?
Yeah, I like to find out more about the person themselves, their own journey, where they came from, what they value as a leader, what are they proud of doing as part of the organization, and what's important to them, what they think is important to the team.
(17:08):
And then, you know, I like to also be open with the team, get to know the team and spend time with the team.
And so when we did our acquisitions, we actually, you know, actually spent time, like we actually flew over to those sites and, and spent a good amount of time with them, in addition to having some of those folks come over here and get to know us.
(17:30):
So I think the two-way curiosity is really important.
I think being open to questions is important.
And I think getting to know people at an individual level, as well as from a leadership point of view, what they think is important for their teams and themselves is also super important.
(17:52):
So just from a, I'm an outsider, I'm just part of the public, I hear about these mergers that come together.
How much time do you, how much time does the average employee actually get to know about that there might be a merger before the merger happens?
Because I always assumed it just happened, and then you're informed, oh, we have been acquired by this company, and now we're coming together.
(18:12):
But it's, it sounds like there's actually a period where they do get to know each other.
Of the acquisition, right?
I mean, if it's a smaller company, then it doesn't, it doesn't have to take that long.
And sometimes if it's bigger, it just the financial transactions behind that take a long time, or have to be approved by somebody else or whatever.
(18:35):
But I think it just depends on the size and the nature of an acquisition.
But there is a period before the acquisition where they can actually come together, not at the leadership level, but just your rank and file.
Usually it gets before the actual acquisition.
(18:56):
I mean, if you're talking about a startup of 10 people, like, really, you're probably interacting with most of them.
And you have to find out the information that you do.
Like, you're interacting with most of them.
But if, but if it's a, if it's a company of about 100 people, like there's, there's a certain set of people that you tend to concentrate on interacting with.
(19:16):
Okay, great.
And, and then I appreciate what you said about one of the things you, where it's hard is if you keep that new company, the acquired company separate, and so that cross-pollination as soon as possible to create that integration.
What's the, I mean, in your experience, what have you seen as, oh, this is, we, how long did it take to feel, okay, we are truly integrated?
(19:47):
Was it three months, six months, a year, two years for it to feel like, wow, we're, we're integrated?
I think it's probably, I mean, again, it's very situational.
I think it depends on the size of the company, but I think it, you can expect it to happen any less than six months, at least, right?
And sometimes it could take to a year.
(20:09):
I think you also have to realize that the, that the reason that you acquired a company, right, is not just, I mean, there's certain goals that you had, right, to acquire that company that made financial sense for a decision to be made.
And I think that you, it takes some time.
(20:30):
And for some people in that company that you're acquiring, it, they also have to think about their own future and whether they buy in or are, or value the, the, the values that you have, right?
And so I think it is inevitable sometimes that some people will discover after a couple of months that, hey, you know, I want to go personally in a different direction, right?
(20:56):
And that's, that's perfectly fine also.
And then some people who are like, oh my gosh, this is great.
You know, I, this is totally for me.
So I think individuals take their own time and you have to recognize who those are and give them that time and space, but also make expectations clear.
I don't think there's any formula for this.
(21:19):
I, I really, like, I will tell you that I prefer some sort of cross-pollination right away, but I really, really think it's very situational, right?
So I'm not going to say that what, what we're doing with the smaller acquisitions we've made is the same formula you should use, like whatever Microsoft decided to do with LinkedIn.
(21:40):
It's just very situational.
Well, thank you for sharing your experience then.
Now moving on to the next question is what do you, what do you do for engineers in particular to help cultivate curiosity on your engineering teams?
(22:00):
Most of the time, I find, I will say the general people in tech, when they don't exercise curiosity, it's for two reasons.
One, pride, because they think that they know a whole lot of stuff, not from a unintentional place, but they're paid to be experts somewhat.
They're paid to know what they're doing.
So I think it comes from a place of, oh, I think I know everything because I've actually put in the hard work to know everything and I keep up with everything.
(22:29):
And so this is where I'm at.
And two, determination and impatience, right?
And so I need to get this done.
I got to go get it done.
So I'm just going to go, like I'm going to go and I'm not going to look back.
And, and again, I think that they always say like your strengths are sometimes your weaknesses.
(22:49):
So I often see, think that when I see this behavior, sometimes it's actually doesn't come from a bad place.
It's just a lot of combination of determination and grit.
And like, I think I know this because I've spent a heck of a lot of time figuring it out.
So my, my take is, is always that when you are trying to make a decision of some kind, you need to understand like who owns that decision in the end and who are the key stakeholders of that decision.
(23:21):
And once you decide that very intentionally, you do have to be curious with those key stakeholders.
And hopefully those key stakeholders will be curious about you, right?
So I, I can't tell you how many times I've been very convinced that what I'm about to do is the right thing.
And then when I actually talk to somebody, I'm like, oh, I should factor that in.
(23:43):
I didn't realize it.
And it has nothing to do with how brilliant I am or not brilliant I am.
And this has everything to do with how you, how you steer an organization and how you eventually do the right thing, I think is a, is a combination of how you make sure you compensate for your own blind spots as a leader.
(24:07):
Because we all have them.
Yeah.
It reminds me of what you were just saying about the bringing together different cultures.
It depends on the situation.
And so one way to slow that down, because I know with engineers, it's solve the problem, solve the problem, solve the problem and outcomes, outcomes, outcomes.
And yet to slow it down, it's good.
Wait, who are the stakeholders in this situation?
(24:29):
Okay.
If we look at that, then I mean.
I feel like we have this culture of you try it, you fail, you learn, you, you kind of try it.
Right.
And so sometimes curiosity gets reenacted that way.
And sometimes the situation is, is very appropriate to be done that way.
Too much questioning also gets you to a place where you wait for too long to make any decision.
(24:49):
Right.
So I think it's a, it's a healthy balance.
Either curiosity, because you are very, I think the important common thing is you are very extremely self-aware.
You understand the risks you're taking.
You understand your blind spots.
You understand the strengths of a technology, the weaknesses of a technology.
Right.
And so you have to remain curious about where you could have possibly gone wrong.
(25:14):
What could you possibly do better the next time?
Maybe somebody has a better idea.
You can do that even while you're doing things, even while you're building software.
Right.
You don't have to like wait and stop the presses.
So, and just depending on some of the decision, sometimes you do have to wait.
Sometimes you do have to process a lot of different levers and inputs because the investment is so large.
(25:40):
Right.
So I, I think it, it's again, very situational, but I think it starts from a place of self-awareness, full awareness of the people in the situation.
And also like really intentional, who makes this decision, who are the key stakeholders who need to align.
(26:00):
Cynthia, since you've been at companies of different stages, different sizes, different stages, do you see a difference in the analysis paralysis?
We're just going to keep asking questions versus, Hey, let's just try it, break it, keep moving on.
Do you, or is it more of just the particular company leadership?
Does the stage have anything to do with how much willingness to just try and break versus asking a lot of questions to make sure it's right?
(26:29):
Yeah.
I think the more customers you have on the line, the scarier it inevitably is.
Right.
You do, you do need to just take a look at it and make sure that you're doing the right thing.
It will move faster as long as you are more self-aware and have the right people involved.
Right.
So again, that you are examining your risks and you are very intentionally looking at pros and cons and very aware of yourself as a leader, your blind spots and compensating for that with who you bring into the fold in terms of making any decision.
(27:07):
Often I find that when you have less customers or when you're still experimenting, yeah, you can move a lot faster and learn by failing.
When you have larger customers at stake, it's a little tougher to do that.
Thank you.
I hadn't thought about that before, but that makes a lot of sense.
How many customers you have and probably also how many, how much support those customers have because a lot of Smartsheet's customers are small businesses who might not have these robust IT teams versus if you're serving a lot of institutional clients who, I mean, there's even just the, the needs of your particular clients too, I can imagine plays into that.
(27:46):
Yeah.
You know, I think there's a difference between having software that's used by a small set of people and one that's used by large enterprises.
Right.
And, and you, you inevitably have to be careful when you are used by large customers and your software happens to be really at the center of what they do.
(28:09):
Cynthia, with all of this, with all of these different remote first, the different engineers, what is your favorite question or way to recruit for curiosity for engineers?
Um, I always liked to ask the question of, can you tell me about a time where you made a mistake and tell me what the process was, what was your decision-making process, what got you there?
(28:42):
And then when did you realize you made a mistake?
What did that teach you?
And then what did you do about it?
Um, and I think the people that I really, it's okay for people to think really hard before they answer that question, but usually the people that do do, they've thought about it so much that it's actually not hard for them to give me a very meaningful example, very, very meaningful example.
(29:12):
And for me, I value that because I feel like they are always questioning whether they've covered their bases, whether they've considered everything and yet still are making progress.
Right.
So they know how to balance that.
And so, um, I think curiosity is really the same as that.
You know, that's how you learn.
(29:33):
That's how you grow yourself.
Right.
Um, I think that in this world of AI, I will say that curiosity is especially important because we read a lot about it.
Right.
But I'm, I'm just like, have you used it?
Have you used it?
Right.
And what is it?
(29:53):
The more you use it, you realize here's where it actually is for whatever your job function is.
Here's what it does well.
Here's where I can still add value.
And here's what it doesn't do so well.
And by the way, that may change next month.
Right.
Um, but here's how I can actually use it to be faster and more effective at my job.
Hmm.
(30:13):
This is going to replace my job because I know a lot of people just rather than the fear, like, I think there is a healthy amount of fear, which I think is, is good.
But I, I think you should also ask yourself what you're going to do about it and what you can do with it.
So, yes.
And I, I like asking that question too, of talk about a mistake, because I'm always, I'm always weary of people who are just, Oh, I've made lots of mistakes, but I can't think of one right now.
(30:42):
Yeah, exactly.
At that point I'm like, well, you were probably not curious enough about yourself and your own and your own learning.
Right.
Um, so how can I expect you to be curious about other people?
So Cynthia, what is inspiring curiosity for you in your own life right now?
(31:03):
So many things.
I think, I think the best part about being an engineer is that things are constantly changing new technologies disrupt our lives.
Um, you know, as a leader of a large organization, I am always curious about leadership itself, right?
(31:24):
How you make decisions, how you can make them better.
Who do you surround yourself with?
Um, am I constantly still learning as a leader?
Am I learning from the people around me?
I like to surround myself with people that I am constantly learning from.
Um, so I, that's why, you know, for me, I have a really strong preference for the size of the company Smartsheet is because it's not too small, but it's not so big that I don't feel like I have an impact on where the company's direction is.
(31:58):
But, um, I feel Smartsheet basically perfect in terms of the size that it is the role that I have.
Um, and the people that I work with, uh, you know, um, so I, I, um, I, I get curious a lot and I get pushed to be curious a lot by my peers.
That's probably one reason I love it.
(32:20):
Because I have a lot of peers.
I have people who will question me, not hesitate to question me.
And that's, that's frankly how I grow.
That's frankly, how I get pushed to also continue being even more curious than, than maybe I was.
So.
And are you referring to the peers that you have in outside of your department, then outside of engineering?
(32:42):
All of it.
Like my, my peers across the company, but also my direct reports and my people managers, I learn a lot from them.
Right.
And I think in part, um, um, I am always, I always strive to have them challenge me or have them ask me questions.
(33:03):
Um, and if I can't answer it, I'm like, I've gone well beyond this point where I have to answer every single thing.
So I'm just not, I'm just not going to do that.
Right.
So I always like to say, here's my hypothesis.
Here's where I stand, but, you know, let me know if you strongly disagree, or if you think I should move in a different direction, um, give me your input.
(33:28):
Um, and I, I'm very clear when it is actually my decision in the end, but I will listen to people and I will explain where my head is at.
So being inspired by your colleagues, that's great.
Yeah.
Cynthia, thank you so much for sharing your insights on how you foster curiosity at work with software engineers at a tech company.
(33:50):
Really appreciate what you shared today.
And I know that our listeners are going to be able to apply it to whatever field that they're working in.
Yeah.
Yeah.
Thank you.
Thank you for having me here.
Um, I have a book recommendation.
Oh yes.
There's a very lovely book that I think really is fundamentally all about why you should be curious.
(34:13):
And it's called Think Again.
And I think that it is a perfect, like, if you read everything in there, it really is about how people should be curious because sometimes that actually saves their lives, saves a company, or leads you to a better outcome in the most unexpected places and times.
(34:36):
So, um, I have really internalized a lot of what that book has been talking about, and I really encourage people to read it because that for me is classic, like, why you should be curious.
That's the book by Adam Grant, I believe.
Yes.
Okay, great.
Yeah.
I enjoyed that book too.
Yeah.
Cynthia, thank you so much for being on the Curiosity at Work podcast.
(35:00):
Thank you so much, Julie, for having me here.
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