In many workplaces, traditional dresscodes and other trappings of professional presentation are considered outdated. But we sat down with The Swaddle’s founder Karla Bookman, and investor/strategist Rupa Pandit, to find out whether — and why — we still need to think about how we present ourselves in a professional setting.

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Saumya: To start off, what are the things that leave an impression on you in a professional setting? From attire to the conversation, what works for you, what doesn’t?

Rupa: It’s important to note that when someone’s performing in their role, they don’t just have deliverables to do but they also have to inspire confidence. It’s the confidence around reliability, on the fact they have the right judgment to make certain calls, that they have the ability to kind of anticipate what comes after the deliverable, all of these things really come in the form of confidence. Are you inspiring the confidence for your manager that you know what to bring to their attention, you know when to make a decision without them, and that you’ve put all the thought that needs to go into that deliverable? It’s not just checking a box and saying, I finished this and I put the ball back in your court; but I’ve put all that decision into it. For those reasons, presentation really matters. You’re doing much more than just sending a document responding to an email, you’re giving people that comfort that you know what you’re doing.

Karla: In a hiring context, one thing that really matters to a manager is knowing the person they’re meeting is going to take this job seriously, that it matters to them, they’re going to put time and effort and thought into it, and they’re going to care about it. There are very small, first impression things that can immediately, instinctively give the impression that you don’t take it seriously. For example, punctuality — somebody who shows up 15-20 minutes late to a first interview — sure, I suppose there could be a reasonable, viable excuse for it. But the impression the manager walks away with is that this person actually doesn’t really care, that they’re not going to put in the time and effort to make sure they show up for this job. Even something as simple as the way people dress for a job interview: we’ve moved away from the times when people have to show up in a business suit to every interview, but being pulled together, wearing clean clothes that don’t have stains or rips in them, showing up in a way that shows you care and took the time to present yourself in a professionally-appropriate way, it gives the impression that you’re going to take the whole job seriously.

Saumya: Has your first impression of someone ever been wrong?

Karla: I’m just going to come out and say it: never, in a professional setting. The rules are very different in a personal setting, but in a professional setting, never.

Rupa: I think it’s really how people define presentation. Presentation is not, like Karla was alluding to before, about wearing the suit or dressing a certain way. There’s a way of just appearing together: it means having read the stuff you’re supposed to read before the interview, before meeting kind of knowing what you’re supposed to know going into it, dressing appropriately in a way that’s professional. I also feel like I’ve never been wrong, that first impressions have never been different from reality. But it’s a lot of cues that are not just a look, but the kinds of questions that the person brings. It’s really the preparedness, whether it’s an interview or a meeting. It’s the fact that they’ve done the homework before, and it’s not a minimum so that they don’t get called out; it’s enough to be able to ask the right questions, to be able to have analysis and thought where they’re part of a conversation and they’re not just demonstrating that they’ve done the work.

To me, the worst thing is always demonstrated effort where people do just enough work to demonstrate that they’ve made an effort because they feel like that’s the bar. But the bar is to go beyond that and say, I want to contribute to this meeting, I want to contribute to this organization if it’s the first meeting or the interview, and to actually have something to say. I’ve definitely never been wrong about those impressions.

Saumya: There are plenty of tips on body languages, power poses, how to shake hands, or just nod and smile available everywhere. Are we basically saying don’t be yourself and instead be this carefully-curated ‘best version’ of yourself?

Rupa: To be the best version of yourself and be yourself are the same things — they’re not any different. In these settings, people have different cues that work for them: they have power poses, things they want to tell themselves, or remind themselves to have enough confidence to be there. But being yourself is absolutely critical. This doesn’t mean being 100% perfect, or hiding flaws or your humanness — in fact, that’s often what makes people better in interview settings, when they can demonstrate their vulnerability because to me, that’s more authentic. I want to see the authentic self, I don’t want to see what people are considering to be the best version to actually be this made-up perfect, plastic version that they’ve put together. I want to see the reality in a way that they feel confident and happy with what they’re presenting.

Karla: That’s perhaps a really important misconception to bust right off the bat: that employers and managers are somehow looking for a bunch of automatons that are these perfect corporate drones you line up, who all speak the same way and pose the same way, and speak in the same jargon. Rupa and I’ve had many conversations about hiring where we’re actually super turned off by people who seem to drop all the right jargon, because there’s something almost inauthentic about it, and it doesn’t show us some somebody who knows how to think on their feet. It doesn’t show us somebody who’s agile and creative in their thinking. I don’t think managers are looking for that at all, I think people should walk into an interview being exactly themselves.

Saumya: When it comes to workwear in the office, everyone has an opinion, from the organization to people you work with. How much of that do you think is justified?

Rupa: I think people should be, no matter what their role is, no matter what their level of seniority is, be conscious of the role that they’re playing in the room that day: whether it’s a meeting, whether it’s an internal discussion, whether it’s representing the firm they’re a part of to an outside party; people should be conscious of that and need to balance that with the individuality they want to show. There are certain things that are universal: being clean, neat, tidy, on time, being able to demonstrate that you’re professional, doing something where the professional you and your role for that day are louder than the personal expression or the personal statement that you want to make. Beyond that, I think it’s important that people be themselves — like Karla said, I’m anti-automaton and all for personality. But I think that people need to do that by being conscious of what’s around them and what their purpose is. The purpose is not dressing however you want, but to build whatever you’re building that day.

Karla: You would also hope that everyone would have the maturity to know the difference. Let’s say in a workplace like ours, where there’s there are no rules about what people wear at the office: basic cleanliness is sort of the bar, and neatness and tidiness. But I would expect that as a manager, people recognize, for example, if we were going to have a corporate client come visit us in the office, that you would dress differently that day, perhaps. And that should be something that’s sort of unsaid, that you don’t need to underscore. But I’ll also tell you I’ve had the experience of a fairly senior-level person showing up to a job interview for a fairly senior position in torn pyjamas. And I hate to say it, it was an immediate no. Because it almost portrays a level of disrespect for the role and for the organization, and for me, who they’re meeting with. I don’t have any particular expectations about what someone does wear to an interview, but I do expect them to not come in torn pyjamas.

Saumya: Coming to the lockdown, now that we barely leave our houses anymore, how has your relationship with clothes or makeup, or just the ritual of dressing-up for professional meetings, changed?

Rupa: The world over, there’s just less effort required given that we’re all in the comfort of our homes, that people are seeing what’s around us when we’re doing these Zoom meetings, I think there’s a little bit more of comfort with just the imperfect, which is great. For me, during the pandemic, I had moments of just being tired of my comfort clothes. And I started to wear dresses every single day for every single thing. This was a personal victory for me, because we’re stuck at home for much longer than we anticipated, so [I thought] this is a way I’m going to make it special.

There is a New Yorker cartoon where they show this woman sitting at her desk with the perfect background right behind her, and then you see below the desk, behind the screen everywhere else around there is real life — I think that that’s everyone’s life in this situation. There’s a certain amount we try to do for everyone else on the call to make things feel like we’re in a work setting, and it’s a meeting. But if anything, it’s less effort than it was in person.

Karla: And I never really believed in the makeup to work thing. I do it when I have meetings with external people, but even when we were in-person in the office, I never would have expected anybody to wear makeup, so I don’t think those expectations have changed. What’s happened on Zoom is that I guess we’ve all gotten a little bit more casual — [points to her shirt] present Hawaiian shirt, case in point. I think that people care less, but the moment we go back into the office, I do think it will shift back to what was before.

Saumya: How do you try to present the best version on a screen? And how can people try to up their Zoom game when it comes to interviews or meetings?

Rupa: A big part of presentation is those things that matter go beyond how you’re dressed, and how you present your background for that particular meeting. It’s the preparedness for that day: for example, when you have a big Zoom call that day but you haven’t checked to see if you have the link or if your technology works beforehand, and there’s a flurry which makes everybody nervous and really impacts the start of the meeting when it happens at the time of the meeting instead of before. Things like not having read the materials and digested them to the point that you have questions or something to say, where you can tell very easily that the person is scrolling through it quickly thinking. A lot of these things people think are easier to do at home, we’re like I’ll just fake how prepared I am for this. Those things are part of the presentation. They’re part of how much of a contributor do you appear to be, that’s much beyond whether or not you’re wearing lipstick, or your hair’s done, or if you’re wearing a Hawaiian shirt. But it matters so much in how I’m going to respond to what you’re presenting and telling me and how much value I’m going to give it — whether that’s conscious or not — will be how much respect do I think I’m getting as the counterparty and how ready are you for this setting, how important was this meeting to you that you did all these things ahead of time.

My advice to someone, especially in this setting, is that we have so much control over how prepared we are, how ready we are, what kind of work we can do ahead of time. It’s even easier when you’re doing this to have notes with you, that maybe in person you’d have to hide from the person who’s there. Have the ability to show that you have done your work and you know what you’re talking about: to me, that’s the most important thing, this setting or in person. But I think especially now when we only get these like four inch squares to evaluate each other.

Karla: And being present is all the more important because when you’re in person, it’s kind of hard to fake: you can’t pretend to try to be present while you do something else. I’ve noticed on Zoom, people have a really, really bad habit of trying to think that they can fool people into being present while they are multitasking. And it’s amazing because you can tell when somebody has muted themselves and is furiously typing emails, or you can tell when they’ve glazed over and they’re watching a different window. You can basically tell what people are doing on Zoom, even if they’re on mute. Things like that are immediate tells that somebody is not present and engaged in the conversation. I think the bare minimum we can do, in this situation where this is the only medium where we meet each other, is to be present and to be very aware of how you present yourself and how you engage across this medium, because it’s all we’ve got right now.

Saumya: The way we speak or sit, or how we look, everything matters. Is perception everything, then, irrespective of who you are, and what you might end up doing?

Rupa: It’s not irrespective, but it’s definitely important. So, having something that’s substance-only, and expecting that your audience is going to be able to read it with the right context and understand all the work that went behind it and have the confidence that this is what they [the audience] are supposed to see, is not realistic. As a manager, the most important thing is being able to understand that what’s been presented to me is somebody taking a full holistic view of what needed to be done, not just taking an assignment and completing it but in that situation, if there’s something else that should have been done that was better, if there was other inputs that I wasn’t privy to that I should know that it’s in there. Those types of decisions, the fact that that person will have the judgment and the wherewithal to figure that out and bring it to my attention, perception is so much of that and builds so much of that.

This is not something where the looks matter or how something is presented matters on its own, but it’s really important for people, especially young people building careers, to understand that this is a necessary part of the role. It’s necessary that if you’ve done the best research, that it’s presented in a way that’s digestible to your audience, that doesn’t mean that it’s got the right look or that it’s flashy. It means that you’re doing it in a way that takes some thought, where the presentation absolutely matters, asking if am I pulling out the nuggets or the takeaways that are easy for this person to understand. If you’re trying to close a deal, but you give somebody all the right things to say but it’s too much in the wrong format, you’re never going to get the eyeballs that you need to. Balancing those two things and balancing form with substance is always going to be necessary, regardless of the role.

Karla: It’s also important for people to internalize that it’s just the reality of human psychology, right? First impressions matter. When you are sending something to a prospective client or you’re meeting somebody for the first time: all of these things matter, and all of them make an impression. And while our personal politics may tell us that they shouldn’t matter, the fact is that they do somewhere subconsciously make an impression. The question then is how do you adapt while still living your values in whatever professional setting, but being able to adapt to new situations and your thinking to say, okay, in these certain scenarios, maybe I do have to dress more traditionally professionally.

But something as simple as not showing up to things on time and being punctual, something that small can completely throw off someone’s first impression of you and make it very, very difficult for them to get over that negative first impression to even be able to appreciate the substantive work that you may do. In a way, some of these trappings of presentation are the gateway to allowing people to actually get to the value of your substantive work. And if you put up all those barriers, give them all the psychological barriers to actually being able to evaluate your real work, they’re never gonna get there. It’s a way to facilitate and give people access to the substance that you can bring, and not turning them off from the get-go.