The Power of Communication: A Conversation with Jaimee Newberry


Jaimee Newberry, co-founder and CEO at Picture This Clothing, chats with TechWell community manager Owen Gotimer about the power of communication, the HIPPO in the room, and how to create psychological safety in brainstorming sessions.

Jaimee Newberry 0:00

My first job was a dishwasher. I was a dishwasher, but you learn all through your career, whatever it is you do whatever you've done, the importance of communication. And I think what taught me the most about communication was sucking at it. I was terrible. I was raised by like a very tactfulless former Marine. My dad was a ex-Marine, and he was not tactful. He was like one of those tell-it-like-it-is kind of a guy, and so that's how I was raised. I was blunt, and I didn't have a lot of tact, and he got me into trouble in the corporate world. You know, my dad also ran a sand and gravel operation where maybe that that kind of approach to things might have worked a lot better, but in the corporate world, it did not fly. So I had to learn. I fell on my face so many times and did it wrong so many times. I hurt people from time to time with my business. And I hate that but I learned from it, and I think that's an important element.

Owen Gotimer 1:00

I think absolutely learning from your experiences is so key. And with communication, I think it's all about practice. I was having a conversation with someone the other day and they said, I don't really feel comfortable talking to this group of people, because I don't feel like I speak their language. You're never going to speak their language unless you talk to them. It'll never happen. Because reading about it, first of all, you have to make the time to read about it. Which are you going to do that?

Jaimee Newberry 1:24

You said "make!"

Owen Gotimer 1:27

I was paying attention.

Jaimee Newberry 1:30

Word choices. So important. You have to make time to do it. I'm sorry, I interrupted you right in the middle of it, but it's true. You have to practice it. And that was even one of the points from the talk today was the "don't be judgy." But that's one of those things that we do judge people from visual perspective, like, every second of the day that we see somebody. I know I'm judged by the hair color or what I'm wearing or whatever. I know that judge happens. But the more aware I am of it, and the more that I practice, like a positive routine of judgment, rather than saying, "oh, that lady must be this" or "that guy must be that," maybe I try to extract a positive scenario from what my judgment is. The more I practice it, the easier it becomes. Then the negative stuff just starts to move to the background, and then the foreground becomes a more positive interaction. And that's a communication skill that is greatly overlooked.

Owen Gotimer 2:34

Yeah, absolutely. And I think it's so important to specifically in the workspaces, what you were talking about today were some steps that you can use to become a teammate that you would want to work with, which I think is so cool, because a lot of times, I think, in the corporate world or even not in the corporate world, you have teammates that you're working with, and you're like, "man, why couldn't so and so do this or that say," well, have you taken a look at yourself and said, "What can I do differently?" And understanding that they also have experiences. I'll catch myself sometimes, someone will cut me off on the highway, being like, "what is this jerk doing?" And I was like, yeah, but I don't know maybe his wife called and said, "Hey, the kids are sick, I really need you to get home." I don't know his experience.

Jaimee Newberry 3:12

Maybe he's driving to an emergency room, right? We never know what the context of somebody's moment is. And I think that's such an important element of it too is we don't have the context of another person's life or life circumstance or situation at any given moment. And that's where, with interpersonal skills, and just kind of like human interaction in the office, often if you find yourself frustrated with somebody, often I do these coaching engagements, right, where I just kind of observe things and then I can offer feedback on how we can improve. Leaders, for example, people who are new into leadership, those are some of my favorite, because I could kind of just shadow them. Take little notes, okay, like "when we were in this instance, you did this action, right? And maybe a way to improve that would be to take a step back and actually look at what you can control about the situation, which is you and your behavior and your mindset, and try to be a little more empathetic in the situation." I approach it a little differently.

Owen Gotimer 3:19

I think it's great and actually brought up something else I just saw on Twitter the other day, was this idea of the HIPPOs voice in a room. I don't know if you're familiar with this idea.

Jaimee Newberry 4:32

No! So there's the elephant in the room? But this is a hippo.

Owen Gotimer 4:34

The HIPPO in the room. It's an acronym that translates down to highest paid person's opinion.

Jaimee Newberry 4:41

Oh, interesting.

Once the HIPPO is brought to attention, teams often climb on to that opinion.

That's so fantastic.

Owen Gotimer 4:52

If the HIPPO comes out early in a meeting or early in a brainstorm people stop coming up with new ideas. Basically this guy tweeted, so I just wanted to get your perspective. This guy tweeted basically, the HIPPO should wait for as long as possible, before they make their case because new ideas won't come about. I tend to think that that's a scenario that probably happens more often than not when the boss talks that people are listening and saying "okay, we have to do with the boss said."

Jaimee Newberry 5:20

So often. So often the case. Oh my gosh. But then there's the interesting interpretation of what the boss said, which goes through like these weird filters sometimes. I could go on about that. But yeah, that's an interesting I like that HIPPO term.

Owen Gotimer 5:50

I just thought it was a really cool concept because I've worked with some teams that sometimes get frustrated when the person that is supposed to be I guess leading the meeting doesn't speak up. And my response to some of those people some of the teams I've worked with is I know that if I talk early that people are going to stop, and actually it's funny because I was in a meeting—I'll get my hand slapped for talking about something internal but anyway—so I was in a meeting an hour long brainstorm and about 45 minutes in I gave my opinion. As the team lead I gave my opinion and right away eight people said "that's it, that's the answer." So I messaged my team, this was four months ago, and just last night, they brought it up again, like remember that time you wasted 45 minutes of my life before you told us your idea. And I thought it was a good idea, too, but because I was taking notes—I have 45 minutes of notes that now we can use the next time we need to brainstorm all the ideas you all came up with.

Jaimee Newberry 6:58

Brainstorming is great because I think It's interesting, like removing that element of pressure. I have so many facets of thought going on at once here, but like, one facet of thought is that how when one person does like the influence person or whatever makes an opinion or casts a statement. This is funny because, okay, so how people will conform to that, right? And this is a funny thing, because my entire career, I was always sort of the rebel against that. And I don't know if that's a good thing or a bad thing, but I would always kind of take the other road. If we're going to do this, are we asking the right questions? And asking questions is super important. Oh, man, I used to coach brainstorming sessions, too. So this is so like, yeah, my brain is just spinning 1000 miles a minute right now. So there's that element, right? Once you have an environment of brainstorming, if you bring in the HIPPO, people will adopt that thinking. To prevent adopting that thinking, how do you encourage that? So like, okay, let's just set up a scenario. I'm going to jump into this, this aspect of it. Setting up a scenario, say you bring the HIPPO into the group, he or she casts an opinion, and the group starts to adopt it. If you're the moderator of the group, how do you shift that? How do you break that up?

Owen Gotimer 8:27

That's an interesting idea. I personally have not run into that. But I think maybe one strategy could be tabling the idea, trying to get new ideas and then circling back to ideas.

Jaimee Newberry 8:41

Here's an interesting thing. When I used to do "how to have successful brainstorming" sessions, I used to always say having an observer in the room so you have a moderator and an observer, right and the observer is almost like sometimes you're going to need a tiebreaker or whatever. But the moderator is supposed to be handling the situation and supposed to remain objective. And maybe if there's a way to avoid having the HIPPO in the room all together, that would be useful. But if that person is introduced in and you have to tie break it, or whatever, get people shifting outside. I guess it's like it is tabling it. I guess that's the best thing the observer can sometimes be the person that calls it out. Can you call out the HIPPO in the room?

Owen Gotimer 9:33

Yeah. Why not? I mean, I think if your team culture is good enough. So I think in certain team cultures, absolutely. If the team culture is there, you can say like, "hey, Sally, we get it. That's a good idea, but let's talk about some other things, and we can circle back to that." Maybe not say it in that tone, because I sounded kind of annoying there, which was not my intent at all.

Jaimee Newberry 9:58

It is funny. One of the the other facets of my brain while I was going on is often people feel uncomfortable saying no or deviating from what a higher up will have to say. So that was something that somehow I was a little bit good at sort of rebelling against. There was the rebellious nature that I have just innately for whatever reason, worked to my advantage. While it works to my disadvantage many times in my terseness and learning that way, it worked to my advantage in that I was able to step back from those scenarios right and really ask the question, like, "what problem is it we're really trying to solve?" because often a higher up will come in with a solution that they have in mind. Let's say you have two islands, and we have to figure out how to get from island A to island B and you were going to brainstorm, what are the possible ways to get from island A to island B? We'll have all these, and we could tunnel, we could build an underground tunnel, we could build a zip line system, and then the higher up will come in and be like "we should build a bridge." And then everybody's like, "Oh my god, that seems so logical. How did we not think of it? The bridge is perfect." But then you have to look at what the real prize is. Is it just getting from A to B, is that really what we're trying to solve? Or is there something else? And so learning to ask questions, I find is a great way to open up ommunication and keep the ideas flowing. So like it may be an underground system that we need to come up with. Maybe a bridge isn't the best method and really learning to ask better questions is what will get you to keep the ideas going and keep the ideas fresh and not shut down the bridge idea but like you said, add it to the list of ideas, but to try to keep it equal, because it's important that people understand, yes, this is one idea. This is the way it's always been done or whatever, but there may be a new way to approach this that actually meets our needs better.

Owen Gotimer 12:13

I think that the asking the questions portion, like I'm thinking while you're talking about this scenario is why do we need to get from A to B? Is it because there's produce on A, and the people are on B, so we need to get the produce to them. Well, maybe a bridge doesn't make sense. Maybe we need to widen the bridge, because we need to get trucks back and forth or something along those lines. Getting to the root of why and being specific.

Jaimee Newberry 12:38

The "why" is everything because it's like, are we just transporting fruit or humans or cars or teddy bears or whatever that really is? Why are we doing this? What problem are we trying to solve? That's it. If you can remember to keep those questions. But it's so easy to get in the weeds when you're in a brainstorming session and somebody like a HIPPO comes into the room. It's so easy to get into the weeds and just be like, okay, we have a solution. Now we have to think about the tactical implementation of this solution. And we get lost and we get off track. And then it's chaos.

Owen Gotimer 13:11

I think a lot of it comes down to when you're in one of those brainstorm, someone comes up with an idea whether it's the HIPPO or someone else on the team, and people start to cling to it, and then their creative juices start flowing. Like that's a great idea. Let's do this, this, and this. And you have to always remember to circle back to what were we tying to accomplish here? Maybe at the end of the brainstorming coming back to the problem, and just addressing like, alright, let's get back to square one. What was the problem, and do these solutions we discussed actually help us solve that problem? Or did we just get off on a tangent because we thought this was a cool. We thought the underground tunnel was the coolest thing we've ever come up with.

Jaimee Newberry 13:55

I love it. I'm gonna ask you a question. So here's the funny thing when you do brainstorming sessions, and I've often done these when I was coaching them, I would go into environments that I'm less familiar with, right, like a company that I don't work at. And I'm brought in to do a brainstorm session or workshop or whatever. And you always end up with that one person in the room who continually derails the conversation. So not as though you are familiar with this situation and have to ask you, how do you solve that problem or that challenge? I don't even know if that's a problem. It's an obstacle though.

Owen Gotimer 14:37

I think maybe from like a manager's perspective, I don't know if in the moment, there are ways you can coach that person. I'm sure there are but maybe taking that person outside of the meeting and having a conversation with them like do you see when this is happening? Maybe not using you right there with you but getting into the situation and helping the group understand that we need to create a safe space because without a safe space, we can't allow creative thinking. We're not going to promote experimentation if there's not a safe space. In the moment if that was happening, though, I don't know if I have an answer for that.

Jaimee Newberry 15:19

Yes, it's the funniest thing. So for a while, I was doing brainstorming workshops on how to have successful workshops. And it's funny because even at those sessions, you would have a participant who was an expert already at brainstorming and how to solve every problem and bless their hearts like the sweetest people always. But it is like as a moderator or person leading the group and trying to get people to get them to keep going, they're constantly getting derailed by one strong personality. It was an interesting challenge. You do have to take control of the situation, but you also want them to know that their opinion is valuable. While at the same time, it's like, you got to shift the topic back on topic, like you were saying earlier, it's like we got to keep revisiting what the point is, and somehow backlog what they're saying, like, "you know what, that is great feedback. I'm going to write that down. But right now we need the group to stay focused on what the task at hand is." putting it optimistically can be very uncomfortable sometimes, but yeah, I love those sorts of personality challenges, though, like I I don't know what it is about those situations that I kind of live for those moments.

Owen Gotimer 16:48

Another challenge that I think definitely comes up more frequently now than it did 5, 10, 15 years ago, when you're doing those brainstorming sessions, and you're not co-located.

Jaimee Newberry 17:01

Oh, those are fun. Those are challenging in a whole new way. And, you know, I was a CEO for an entirely remote company at one point and there were 36 employees. So I can absolutely relate to that situation where you have people dialing in basically from wherever they are. Sometimes they're participating. Sometimes they're dealing with family situations going on in the background. I used to have a cat that I still have this cat but during these calls, his meow sounded like a small child saying mom, and people will be like, do you need to go help your kid? They just thought it was a terrible parent, but it was a cat. He was fine. He was just hungry. Always. But anyway, it's just posing like a whole new situation. Are you doing those sorts of brainstorm sessions and what are you doing?

Owen Gotimer 17:55

So we definitely have brainstorm sessions remotely. Our entire team is distributed. We work with other teams that are kind of in the same boat. Something that we've started doing is making use of the tools we have at hand. So we love using video, because it helps. For me personally, a lot of feedback I get is I don't pay attention, which I appreciate it, and I'll own up to it. I know that that's something that I'm working on right now. So over the last six months, I've been turning on my video camera, because I feel like it holds myself more accountable. If I'm distracted looking at another monitor over here, then these people are like, "hey, Owen," and they'll kind of call me out. So that's one of the strategies. I think that I've heard other people talk about the strategy of using video. Also, maybe changing up how the brainstorm happens. So we sometimes brainstorm just talking to each other. We sometimes brainstorm using Google Sheets or a sticky note website or something along those lines to try to make it interesting so that people don't get into this monthly mundane repetitive task of thinking, "oh, we're just here because Owen said we had to be here." They can get excited about it like, "oh, we're trying this new thing, and I have these new ideas." And really just empower. I think empowering the team to letting them know like, here's a space for you to throw whatever ideas you have. Let's just write them down, and then let's figure out what these really mean, and what they're going to take to take us to the next step, and if they can help us solve the problems that we're currently experiencing.

Jaimee Newberry 19:29

This applies to whether it's in person or remote distributed sorts of brainstorming sessions, but the preparation that you do before the session pays off immensely in those sorts of situations. So there's a lot of prep in how you time structure brainstorms, and then that time structuring plays out continually throughout a brainstorm session. So like, "okay, we're going to brainstroom problem x for exactly five minutes, and in exactly five minutes, I want you to write down as many ideas as you can." Those time structures tend to help keep people more engaged in my experience, and I love that. I remember learning that at some point early in my career, and I was like, this is amazing, because I get excited, and the pressure of the time and trying to do things as quickly as you can within a tight timeline definitely helped keep me more engaged. Now I find it tends to work pretty universally as well.

Owen Gotimer 20:35

So when you're working with teams, something that I'm thinking about now is, and we touched on it a bit, was creating a culture where people feel comfortable doing that. So you have a team of eight people, and you say you have five minutes to brainstorm, there are going to be the people with opinions. There are going to be some people that are always kind of quiet in the back, but you want their opinion. What are some strategies that maybe you've experienced to try to encourage and create a safe space for people who maybe are less prone to share their ideas openly?

Jaimee Newberry 21:08

Okay, so there are a couple different ones. So I'll adjust first, the sort of the naysayers who will be present. So when I'm doing a brainstorming session with a very particular mission, I have no tolerance for the negative. I love the devil's advocate perspective, and I think it's a necessary part of developing an idea out, but I think there's a time and a place for it, and brainstorming is not it. So what we used to do in, like in the corporate setting, is you have a brainstorm session. You follow up with something—we call it the black hat session. The black hat session—like historically a person with the black hat is the villain, right?—so the black hat session is where we narrow after our brainstorm, we've narrowed it down to three top ideas, and we're trying to figure out let's have a black hat session and poke holes in these ideas, and then we'll figure out which one is the right one. So you have a separate sort of session where everybody is able to bring their reasons why it won't work, or whatever negative nonsense. I will call it nonsense but nonsense is actually not the right word for it, because sometimes the negative stuff that surfaces is very valid, and it's very valuable in helping determine if this is the right path forward. But I think what the black hat session does is it allows those folks who are feeling a little shut down or a little like they've been heard, or that they have valuable reasons why this x, y, z is not going to work. It gives them an opportunity to speak up, and it is one of those things that you have to frame. It's like you speak now or forever hold your peace and you don't get to complain and vent all over town about what sucks about this. I found that those sorts of sessions really helped relieve a lot of tension on certain teams, where that kind of stuff was present.

Then you have the quiet person. You know this person is super smart, but they're super quiet. Okay, so my significant other is that person, and we used to work together before we became a couple, and he was always that guy who did not want to speak up in a group, didn't even want to be in the group, but always had really valuable perspective to bring to the table. And I knew he was not comfortable being singled out or called out in a meeting. But what I would do is make time to meet with that person, because I tend to be fairly introverted. I hated being called on English class to read a paragraph or two, you know, it's that sort of thing. I think respecting the boundaries and the comfort zones of different people while still asking for their contribution. You just know sometimes as a moderator when somebody has something valuable to add, if you observe, when you're leading a group like this, you'll see when thoughts are happening. So if you can make a note to yourself and approach that person afterward and say, "You were very quiet today. I respect that. But I would love to know what you thought. Would you mind putting together an email of your thoughts or talking to me?"

Now, coming up with the time to talk through it, because I know you're uncomfortable in these situations, you don't even have to call that out. But when it's a person who's just introverted—and I respect the boundaries of an introvert, I really do—they don't like being called on often, but you can still get really, really, really sometimes the most valuable information from those folks. They're so smart.

Owen Gotimer 25:40

Do you think in that scenario, where you recognize that there's a thought happening and maybe that person is comfortable sharing and you take them outside a one-on-one and you have that conversation with them, and it works this time, and you do it again, and it works. Do you think that there's a level of comfort growing in that individual?

Jaimee Newberry 26:02

I do think that it can happen, and it will always be on an individual level right, but I do think with certain individuals over time it can build enough confidence where they start speaking their mind within those settings. It becomes a safe space for them, and I think that it's about building a culture. What is it when you're building a fire? You start with a little twigs? You gotta start really small and then get a little flame going and then you build it up bigger and that's really it the kindling, that's the word.You do that with people to build culture. Once you've established that, and they trust you, I guess it's earning your trust. Once you've earned the trust of that person, they will start to open up more in different circumstances. And if they're not comfortable, they will feel comfortable enough with you that they trust you to know that and to be forward with you about it. So you can ask periodically, "would you feel comfortable talking about this idea to the group or to the committee? I would like you to present your idea and take credit for it." I think that that's an important element of it, too, you know?

Owen Gotimer 27:29

Yeah, for sure. And I think that something that's so important, and you talking about building the culture in creating this space where even the quiet people in the room are willing to share. Maybe one-on-one is so important in all fields, but in software, specifically, and in tech specifically. I often hear at some of these conferences I go to "Yeah, you have the culture that's good, and then you..." Like wait a second. Why did we skip over 95%? Like the tool implementation? I'm not a tools guy. I'm not a hands-on software guy, but what I've heard from a lot of different people is that the tools are the easy part. I don't want to say that coding is easy.

Jaimee Newberry 28:16

There's a technical skill to it, we acknowledge.

Owen Gotimer 28:19

But the human skills are so hard. I wrote a blog post— a self plug shamelessly for a blog post I wrote—called, "we should stop calling them soft skills," which is why when we sat down I suggested we talk abouot interpersonal skills. I'm very specific about using interpersonal or human.

Jaimee Newberry 28:44

I talked about a product is the connective tissue between human beings, right? And if we are sensitive to that, like if we are developing healthier teams, like we hire people, usually based on their technical skills. They bring a resume to the table, we are always looking at a culture fit as well to a certain level, right? But yeah, the soft skills. If you are hired for a team, because you're really good programmer and you met like the entry requirements to fit our culture, that's great. But there's more to it than that. The soft skills element of it is a continual practice. I'm a person who I've coached soft skills and human skills. I worked in user experience as a mindset for two decades, like I've been doing this a while, and I still have so much to learn myself. I don't feel like I can practice enough and get good enough at this that I feel like I am an expert in some regards, yet I still have so much to learn and there's a constant practice. Do you do yoga at all?

Owen Gotimer 30:01

I had tried it at one point. A past significant other of mine tried to get me to do that. Yeah, it didn't work.

Jaimee Newberry 30:10

I don't do yoga now. But there was like a ten year period of time where I did. But what was great what I loved about the practice of yoga, it was about being in practice, right? And no matter how good you were at something, there was always a next level, there was always a way to combo up the downward dog pose, right? So see like a simple downward dog pose. And I say simple. It's not simple for everyone. But say you get to the point where I can do a respectable downward dog and then move into my next Asana and roll forward. But if your downward dog feels easy, try holding it for 60 seconds. If that's easy, try 120 seconds, try for three minutes, five minutes. There are always checkpoints and ways to make something, a greater challenge to improve your skill at that thing. And communication skills or soft skills is exactly that. This is when we talk about check-yourself checkpoints. We can't always control what's going on around us, but you can control you, you can control your mindset, you can control the words that come out of your mouth. If you practice those things, they get better, and the world around you somehow gets better.

Owen Gotimer 31:39

One thing I love that you said and I've talked with people about this before is you said I consider myself an expert in these things, but I have so much to learn. And there's a quote somewhere and I'm going to botch the quote terribly. But the basic idea comes back to you're not an expert until you admit that you're not an expert.

Jaimee Newberry 31:58

It's true. It's funny because I think as we age, like in our 20s, we're often so confident and a lot of us doubt ourselves or whatever. But like we're so confident in what we know, that we forget to question things, I think and with age and time—I'm 44 years old now—like the older that I get, and I have dear friends in their 50s and 60s, who you know, they kind of like look at me and go, "Oh, haha, youngster, you still have so much to learn grasshopper." And it's true, and I appreciate and respect that perspective, because I do know that I try to appreciate when I see somebody in their 20s full of confidence and drive and all that. I appreciate it, and I respect it, and I can't change it, even if I see it as flawed. But I could smile at it and remember that I was probably there. I was that person in a lot of ways, and over time, I guess we become more open minded and hopefully more accepting and more balanced on what's important and what is worth letting go of and not getting all bent out of shape over. For me, I feel like that along with practicing, sort of putting my energy in positive places—I sound so like earthy and I'm so not really an earthy person—but I do believe that the energy you put out, you get back. I do believe that fully just because from my own experiences, it has been everything I've experienced, and the more good stuff I put out into the world, the more good stuff I get back, and it just feels good. I like that life way better than being really heavy with frustration or judging or any of that. So, that's what I choose. It takes practice. It's not something that comes easily, but it takes practice and the more I practice, the better it gets.

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