"Navigating Executive Communication & Securing Support" (Video & Transcript)

"Be brief, be brilliant, be gone. When communicating with executives, present crystal clear data with relevant metrics and be clear with your ask." - Shama Keskar

"Know your audience. The more you speak up, the more visibility you get, the more people know you, that is what will get you to that next level." - Shareen Islam

"When you go into a meeting prepared, even if you don't know what it's about, if you have something you're asking of them and you know exactly what you want, you can get something out of it." - Shareen Islam

Emily Leathers is an executive and leadership coach and has managed teams from two people up through being a VP of Engineering at a startup and leading Trust and Safety Engineering for Pinterest. She’s the founder of Exceptional Leadership, where she helps ambitious leaders build impactful careers they love without sacrificing their authenticity, their values, or their life outside of work.

Shama Keskar is a CTO, Founder, and mentor with experience leading engineering teams at Amazon, Google, and LinkedIn.

Shareen Islam is an Engineering executive with 20+ years of experience scaling high-performance teams and delivering complex digital transformation programs across enterprise platforms. She is an industry leader in diversity, equity, inclusion, and allyship, serving as the GM Women+ Technology Ally Lead and mentoring young women and girls in STEM fields.

Transcript has been edited for clarity.

Emily Leathers: Thank you so much, Karen, and thank you so much to our audience. We are so excited to have you all here today. Shama, Shareen, and I are going to be having a fireside chat about navigating executive communication and securing support. This is, of course, a huge topic. We're going to hit on five key areas: what an executive is, plus four other keys to communication that we've thought of ahead of time for y'all, and then as many more areas as we can come up with time for in the Q and A, and you guys can come up with questions about. Please, please share your questions and thoughts, and chat throughout our discussion. We love hearing your feedback. We love hearing your questions. I may wait until the end to read out some of the questions, but we're seeing them and loving them as they come in.

And then we're going to start by introducing our lovely selves. I'll share a quick what you should take away from this session, and then we'll dive into the conversation with Shireen and Shama. I'll warn you ahead of time, I speak quickly when I'm excited and when I'm feeling under time pressure, so I may zoom through some of these interstitial in question sections. You can always flood the chat with "Slow down!" if you need me to. Alright, I'm already talking, so I'll start off. Hi, I'm Emily Leathers. I'm an executive and leadership coach and managed teams from two people up through being a VP of Engineering at a startup and leading trust and safety engineering for Pinterest. I'm the founder of Exceptional Leadership, where I help ambitious leaders build impactful careers they love without sacrificing their authenticity, their values, or their life outside of work. Some things I found very challenging for a long time, and I'm now finding really rewarding to take my growth on and help as many other people as I can. Why don't I pass the mic to Shama?

Shama Keskar: Hi everyone, I'm Shama Kesker. Pleasure to meet each of you and it's an honor to be part of WEST,. I started my career as an engineer and worked my way to a technology executive role. Currently I'm working as an advisor, CTO for one of the venture studios. Then I'm also working as a head of engineering, which is my full-time role with AI healthtech startup, and I'm mentoring some of the upcoming founders, like next-generation founders at Oneday. And I've co-founded my own company called VoxAI, so that's about me. Shareen. Please go ahead.

Shareen Islam: Yeah, so I'm Shareem Islam. I also started off as a software engineer. I did that for many years and then transitioned to a software development manager. I was a software development manager at General Motors, worked my way to senior manager there. Moved over to Choice Hotels, where I am a software development manager here as well. I also am very involved with women in IT organizations, mentoring middle school girls and just women in IT in general. And I'm also on the IT leadership board of advisors for Paragon, so that's me.

Emily Leathers: So Shereen, Shama,, and I had a chance to talk ahead of time about this fireside chat, and when we talked about communicating successfully with executives, four key areas emerged in that conversation. The first is understanding the purpose of the meeting. There are lots of different contexts you could be in when you're having a discussion with somebody who's outside of your normal day-to-day team, right? They could be checking in on a project, they could be seeking some ideas for something the company might want to work on in the future. They could be checking in with you personally. You want to make sure you always understand the purpose. You want to do your homework on your audience. This is always great advice for communication, but it's especially important when you're having a conversation with someone whose role and job is very different day to day from yours, and there's somebody who's not as familiar with you, your team, or your work.

You always want to walk in with clearly identified requests, even if the meeting isn't about you requesting support. The number of times I've had somebody ask me, "This sounds amazing, what can I do to help?" and me or the team I was with were flatfooted is not great. So you always want to have that. And then you want to prepare the before, during, and after. And this is really just good meeting hygiene, pre-reads, visuals to keep the conversation clear, action items, written collateral you can give afterwards with more detail, all that good stuff. We're going to structure our conversation around those four keys, and then I'm going to share a Google doc with you in a couple of minutes that has them written. You do not need to write them down, you do not need to remember them off the top of your head. You should remember them in your work.

And before we dive in, we also wanted to take a moment to define what executive means and how their job is different from yours or your managers'. Before I give this discussion, I want to mention that there are two types of executives you might encounter. One of them is the executive suite of your company. This is a subset of the people who have C-something-something in front of their title, and it's usually the people who report directly to the CEO. There's a second set that's often referred to as executives within your team or company, and these are people who are that senior leadership group for the group that you are part of. So, for example, if you work at Google, there are the executives at Alphabet, there are the executives at Google, and then there's also maybe the search executives for your team. You might interact with any of them. You can also imagine that anybody who's your manager's manager's manager or above is probably someone you should interact with this way regardless of what their title is.

Okay, so I see an executive as having three main jobs, being part of the small circle of senior folks who think holistically about the company or the entire section. They represent their domain to the rest of the company's executive leadership, to the board, and to investors, and then they represent all those people back to you and your org. They're a translator. They're a lot more about communication than about being the person who sets the plan or executes it, which sounds ridiculous. I know we all think the CTO is in charge of the technology. They're actually in charge of talking about the technology to everyone else and talking about all the non-technology to the technology people, and then what sounds like a direct conflict to what I just said. They're the one person who's most accountable for the domain orgs they lead hitting all the goals. So not only do they do very little technology, they're accountable for all of it. Congratulations.

Shama, you've actually been in these roles for a while now. Can you add some color and flavor to those ideas?

Shama Keskar: Yeah, when I think about an executive, there are four segments to aid. One of the segments is leadership and collaboration. So executives are the people that you want to follow. They usually model the behavior they want to see in their leaders. So definitely leadership, mentoring, coaching, all those aspects are part of the key factors for an executive. Collaboration. Executives are the ones who will bring the organizations together. They foster collaboration. They are the ones who manage a relationship with investors, board members, advisors, partners, customers. So definitely that's one segment. Second segment I can think of is strategic thinking. Executives are the ones who end up making some of the tough decisions based on economic conditions, market conditions. They are the ones who would decide whether to pivot the strategy or continue with the strategy that we have. So that's another angle to it. Decision-making, which is very critical.

Executives will usually be adaptable and resilient to make those tough decisions. One of the good examples going on right now is layoffs, which is ongoing across the board. Some of these tough decisions are coming from executives based on economic market, investor, whatever different conditions are, and communication is really important. Having the consistent communication because executives think about it like they have to manage investors, board members, advisors, as at the same time they have to manage the overall employees of an organization. They are the ones who might be managing the key relationship with partners or third-party stakeholders. So having a consistent communication mechanism is critical, able to articulate reasons, the strategy even to non-technical stakeholders or technical stakeholders, investor is important. So in my mind, that's executive.

Emily Leathers: Thanks, Shama. Yeah, I think keeping in mind that executives have such a huge variety of areas they're focusing on at every time and how they're thinking about so many more things beyond the conversation you're having right now and they're fitting it into such a wide variety of contexts as you mentioned, is really going to help folks get off to a strong start and it's going to explain a lot of the advice that we have. So now let's jump into each of those keys of success. The first was being sure you always understand the purpose of the meeting before you do your prep and definitely before you get into the room. I know for me, there's a set of three questions I ask myself before I start writing any slides, pre-reads, or anything else, it's what is the executive's purpose for this meeting, what is my purpose, and are there ways in which those two purposes are different?

So sometimes I will have an executive call us. I will have somebody say, "Hey, we'd love an update on this big project that you asked for support from across the company." Let's say we were doing an upgrade to Python 3 at Pinterest a couple of months before Python two-seven was end-of-lifed. This was like an existential necessity for the company from a security perspective. It also required cooperation across a gigantic set of people and had been put off a whole bunch of times, and we got called into a bunch of rooms to explain how is this going, and was the company going to be okay? The goal for the people in that meeting was basically always, are we on time? Can we trust you? How do we make sure the company doesn't have security flaws? My purpose was to reassure them that we're fine, but to show my tech leads in a really, really positive light and to make it obvious that my team needed more staffing because we had about half the size that we needed in order to be functional, and it was exhausting all of us. So you can see how those are compatible, but they're actually very different, and then we talk later about the asks. The asks I might walk in with would give me more staff, which is completely different from what the meeting was about, but hopefully a case I could make. I'm curious, Shama, I know you had some great stories about when you misunderstood the purpose of a meeting and it went kind of hilariously wrong. Can we convince you to share some of that with us?

Shama Keskar: Yeah, absolutely. One of the examples I would take is, there was a startup I was working for, and that startup had a tradition of daily meetings where executives and some of the key leaders from the company would get together and talk about some of the aspects. Anything that's critical, important. Great tradition, having an open dialogue is always great. However, one time, since these daily meetings didn't really have an agenda or a specific measurable outcome expectation. One time, one of the distinguished engineers presented something with charts, graphs, a lot of areas that they focused on, what they have worked on, what are opportunities, how it's going to help impact customer, all of those great things. At the end of the presentation, one of the executives mentioned that this is great, however, this is not aligned or this is not the thing that is being prioritized by the company.

So it's hilarious. Yes, because you're presenting something that is not aligned with the company's prioritization. It was definitely hilarious when every executive made that comment. However, think about the gravity of that situation that, hey, you are working on something that's not aligned with the company's mission values, or you are presenting, you've done some work, and you work pretty hard on something that is not as per the overall north star region of the company. Naturally, the key learnings from that meeting are making sure that you have a clear agenda, or making sure that hey, what you're presenting is as per the company's business goals or the overall niche, the vision or your customer, your revenue. So keeping all those things in mind are critical. So I would say that definitely knowing before what you are presenting, helping executives learn ahead of the time that you're going to present something, so you can avoid all those jargons, unnecessary frictions. So that's my story.

Emily Leathers: Yeah, Tina, I love your question. We are going to answer a portion of it in just a second, and then we're going to get to some of the details of it at the end when we get to the Q and A. So Tina's question is, what would you do if the exec is unclear when sharing their purpose? My next question is how do we figure out the purpose of the meeting? Shareen, can you share some of your tips?

Shareen Islam: Yeah, so first off, take a look at the agenda, and if there is no agenda, ask around. So I always ask my peers, "So hey, I'm going into this meeting with this executive, have you ever met with them before? What are they like?" I'll ask my leader, I'll ask my boss, I'll ask my boss's boss. If you have peers or friends within the organization, ask around and take some time to prepare for the meeting. After you prepare, run it by your leader. "Hey, this is the deck I prepared. What do you think?" I have mentors. If you have mentors, run it by them. Ask for feedback, and you'll find that that will kind of help you get a little bit more prepared. And I've had that feedback before where one time I prepared a deck for something I was going to present to an executive and my leader said, "Hey, this is great, but who you're presenting it to, they used to be an architect and this is going to take you down a rabbit hole you do not want to go down, so be careful." And that was great, that was wonderful feedback for me. So I was more prepared when I went into the meeting, and I made sure to, one, be a little bit more concise and very clear about what I wanted to present when I was presenting. And then when I was in that meeting and I started seeing them go down this architectural rabbit hole of something I didn't want it to go down, I could redirect them. So ask questions.

Emily Leathers: Shama?

Shama Keskar: I would say know your audience and have the relevant audience. I have been in meetings where the audience was 20 people. Some of them were relevant to the meeting, could contribute, some of them were not relevant. A successful meeting has not more than seven, five to seven people. Then you can have productive meeting. So definitely I would say audience is another important factor. Who are you inviting? Who's participating? What's their background? Knowing that is critical, and I have been part of Amazon, some of meetings at Amazon where we had had prepared documents and meetings literally started silent, with silence. Everybody reading the talk, adding their comments to the doc and then coming out of alignment or a follow-up, some sort of action-driven meeting. I have experienced that [inaudible].

Emily Leathers: By the way, I love Michelle's comment in the chat that as a leader, they really appreciate it when people prepare the agenda before they meet. I've definitely had folks reach out to me and say, "Hey, you invited me to a check-in on this. These are the three topics I was thinking of covering. Does that sound good to you?" That is one way. If you've done what Shereen and Shaman have suggested, you've asked around and nobody really knows why this is on everyone's calendar, you can absolutely say, "Hey, these are the topics I was considering hitting. Does this answer it for you?" My questions are very similar. If you really aren't sure, you can ask three questions of your manager, your colleagues, or yourself. What's this person's perception of my project? So if this person's perception of our project is that we're off track, they're probably looking for a status update and reassurance, and for you to build trust. How does this person's job relate to my project?

So if you think that this is a top three area for the domain this person is in charge of, or it's something that their team might need to rely on in a couple of months or a year, they're probably coming from a fear-based perspective. You'll hear me talk a lot about safety and fear in the work that I do, but it's very common for someone to be like, "Oh no, will my performance review look bad because my org didn't deliver? I'd better check in." And then what does this person usually worry about? Do they get worried that projects are over budget? Do they get worried that a team isn't focusing on the right area? And what can you do going in ahead of time? We're also really starting to hit on that next key, which is do your homework and know your audience and, in particular, know where you can.... What is the power structure of the people in the room? How do they relate to each other reporting-wise, formally and informally? And then who is the person in the room who can veto things, right? Who's that person who everyone else is going to look to? It may not be the person highest on the org chart. It may not be the person who called the meeting who's going to be the one who can jump in on everybody else and ask questions and actually move the room forward.

I'd love to hear some experiences. I think we all would, of some success stories. So, Shareen, maybe you can start us off with what's a way you've tailored your messaging to the person and it worked.

Shareen Islam:

Again, know your audience. And so I always ask, "I'm going into this meeting, who am I meeting with?" I had another executive, ex-military, and he was very to the point, and I noticed really quickly previous executives when their meetings would be held, they'd be two hours, hour and a half. His were always half an hour and they were very short, concise, to the point. So when I would meet with him, and before my first meeting with him, I did, I asked my boss, what should I expect? And that's what he told me, he's ex-military, to the point, don't go over time, don't waste his time, and just make sure you have your data and you have your answers ready to go. So when I would go and meet with them, I had my bullet points, I had my data, I had everything ready. My deck was very concise, to the point, and I had all my answers ready for him, and that's what I would have prepared for him is very short, concise to the point. Half an hour we're in and out.

I had another executive, loved telling stories, and my meetings with them, they would be an hour and a half, but they would always go to two hours. So I knew, don't have a meeting scheduled after him. Always have a little bit of a break, a buffer time because they would always run over and have stories, anecdotes, ask him about his day, how was your vacation, and get to know him a little bit and chat with him, and also talk about what I needed to talk about, have my deck prepared. But it was a little bit of a different communication style. So know your audience, know how to communicate with them, know how to get that point across, and that, definitely, I think, is what works.

Emily Leathers: Shama, I think you had some thoughts here, too.

Shama Keskar: Yeah, absolutely. I'm happy to share one of the most recent experiences for my own startup. I'm working on VoxAI, co-founding a social behavior analysis startup. I had recently pitched my startup to two potential investors. The approach I took that Shareen just mentioned, storytelling, it works really great. So the way I approached those investors is literally talking about my experience, and then what are the key aspects of my leadership experience. Then what is basically what problem I had encountered or challenges I had encountered, and then what actions, what was the impact on the customer, and what actions I took to resolve those challenges. And then I started digging and researching, is that problem statement universal, do people come across this, and nowadays ChatGPT helps you with bringing all the global information into a single browser. So I asked ChatGPT the same thing, started doing my own research, and I realized that this is a larger, a global problem, and then started thinking about the solutions, and then when presenting in front of the investors, I presented with the global market data opportunity.

However solution is going to resolve this, how it's going to have positive customer impact projection, and all that good stuff. I didn't really have time to prepare a fancy pitch deck or presentation when I was meeting this investor. It was just last-minute meetings that were set. But my storytelling approach helped investors understand the problem; they could relate to that, as well as they could understand the solution, and the questions that they asked were very relevant, and I didn't have to repeat any information since they got the problem and the solution. The rest of the discussion that we had was very productive and to the point, and it was overall a productive session. So storytelling helps.

Emily Leathers: And we've been hearing a bunch of this in the chat, but I love knowing what distracts someone or pulls them into sidetracks. I worked for a manager at one point who was so focused on execution that if they were worried that you didn't have a rock-solid execution plan, as good as they could come up with, it was all they could think about in the meeting. So I would have to start meetings with them with, "We have this plan, we have these three milestones. I'm happy to walk into details with you later, but today we're actually going to talk about just this thing," and every time they'd go into that, "It'd be awesome. I would actually love to catch up with you on that in our one-on-one and send you our doc and today we're just going to focus on...." sometimes that would have to happen like five or six times in a 30-minute meeting.

It takes some guts to tell your manager's manager no, especially if you can see they really want to go somewhere. Notice the trick is, if they're getting anxious or distracted and they can't focus on you because of that, "Hey, let's jump into two or three things because it's come up a couple times, but I know that means we might need to reschedule some of this conversation for later." I'm like just recognize all our smart folks who have some emotional intelligence. Recognize that the person you're talking to is human, and if they can't focus, you are going to have to help them. But as much as you can understand ahead of time what sidetracks them, and either do not put it in your presentation, someone already said this, just avoid that section entirely or head it off upfront. And, of course, things do not always work out the way we expect them to. So we've talked about making sure you know the purpose of the meeting, about doing your homework. Now we're going to talk about, oh wait, things don't always work out the way we expect them to. My intention was to have someone tell a story there. I just did not put the break in my notes for it. Which means I also don't have the note of who was going to tell that story. Who wants to jump in and do it?

Shareen Islam: I can tell one really quick about just something recently, I don't know, Shama, if you had something too. Not a great, this is a hilarious thing that happened just recently, and it talks about exactly what you talked about, about not knowing when somebody gets distracted. And so we were just in a meeting this week with some executives, pitching an idea, more for their blessing. We're going to do it anyway, but we just wanted their blessing so everyone's happy and sometimes you need to do that and this executive fixated on something and we didn't really realize that they were going to fixate on it and we should have known, we should have known and they fixated and the entire meeting was just derailed by what they were fixating on and if we had just caught it sooner, the meeting would've just gone differently and now.... It got a little heated, we smoothed things over. I think we need to have a few more meetings to pitch it a little bit differently. So lesson learned.

Emily Leathers: And now every time someone on your team meets with that person, you're going to prep them with, this person can get fixated on X, here's what to check, and here's what to avoid.

Shareen Islam: Absolutely.

Emily Leathers: Okay, so we've talked about making sure you know the purpose of the meeting, about doing your homework on the person or people you're meeting with. Now we're going to talk about walking into the meeting having already identified one to three things you could ask this key executive for help with. Even if they've set up the conversation, even if it's a progress check-in, and it isn't supposed to be a request meeting. Shareen, could you share a little bit about why it's so important to always have something you could ask this executive for help with, to have always thought about those requests ahead of time, and to make them super, super specific?

Shareen Islam: Absolutely, and the reason is that you're there for a reason. You're not there to just hang out with this person, right? You're there for a reason. So be it to give them a status update or pitch a new idea. You want to walk into that meeting prepared with what it is that you have to offer and what it is that you want to get from them. So is it that you want more resources? If it is, how many resources that you want and have that data ready, how many resources do you want and why do you want those resources? What is it that that executive is going to get out of it, and what is it that you need those resources for, I think is really important... and exactly what resources is it do you need? Do you need another senior engineer? Do you need A DBA?

Can you make due with two junior engineers if they can't give you the senior engineer? Have all of those different strategies in place before you go in. Do you need more funding? How much funding? Why do you need that funding? Was it poor planning? Be prepared because they're going to ask you those questions. And so I think when you go into that situation with that in mind, it helps. I recently...I'm new to Choice Hotels, and I recognized, I mentioned earlier on, that I'm very, very involved with women in IT, and I recognize that our women in IT group here isn't as active as I'd love it to be. So when one of our executives was in town, I introduced myself to her and I said I'd love to do more. And she set up a one-on-one with me. And so when I met with her, I really didn't know what to expect.

So I actually prepared a deck for myself that I just, with some points, with some data points on just women in IT, statistics, things that I would love to see happen here. I didn't even present it to her, but when I was meeting with her, I was kind of going off of these points and talking to these data points and talking to the ideas that I have and the idea that I'd love to pitch and start doing here at Choice Hotels. And it was wonderful because at the end of the conversation, it was almost like she was taking notes off of what I was telling her, and she asked me to send her some ideas that I have, and I was able to just take that deck and send it to her. She then sent that to some other executives that report to her and asked them to follow up with me, and they've now asked me to pitch these ideas to them, so I can start. They're like, you have a lot, so pick two. But that's what happens, right? So when you go into a meeting prepared, even if you don't know what that's about, if you have something you're asking of them, and if you know exactly what you want, you can get something out of it.

Emily Leathers: Yes. And I just want to highlight something Shareen said at the end. Always have something the person you're sharing with can forward. I loved that they just said, can you just send it to me, and I'll share it? If you send it in a format that they can just reshare, it's so much easier for them to reshare. You're asking them to do less work. I love that you put that in there. I think that fits in our next key but was too good not to highlight here. Alright. Okay, Shama, I think our audience would love to hear from your side what makes a request easy for you to say yes to.

Shama Keskar: Yeah, it's simple: being brief, being brilliant, and being gone. So those are the three aspects that I usually consider. You definitely want to avoid surprising your executives, keeping them in the loop, keeping them informed of your actions. Any goal that you're pursuing will help. And you could totally do this by sharing some of the regular updates, dashboards, reports, any mechanism can be helpful. It basically helps facilitate trust and overall decision-making. So when you are approaching them, they are already aware, and they can help navigate or make the decision for you. If there is a situation that we have to present some risk, definitely present it with mitigation, come up with some of the recommendations. So I'll take one of the examples from one of the startup I worked for, especially after the pandemic era. I felt that the company had a need for driving a DEI initiative: diversity, inclusivity, and equality.

Now I wanted to make...being startups, small company DEI initiative could be jarring or daunting. So the approach I took is I literally highlighted what is that one thing that's missing today? And then created a goal like hey, here is goal and here is the overall measurable outcome or metrics, and how it's going to help bring either teams together or the best of engineering, non-engineering together. Overall how it's going to present the company as a brand in whatever technology or sector they're working in. With that sort of approach, having a crystal clear goal and then specific actions, and then overall impact not just on employees but even your customers, overall company brand. When I went with that approach, it got approved, I got funding to drive that, and we actually started the overall DEI initiative within that company, which helped us attract some of the more diverse population to join our company. It created an environment of a sense of belongingness. So that's what I would say: be crystal clear, go with maybe a goal and then some of the objectives or some recommendations with pros and cons. Do your study when you are presenting, especially in front of executives, they would be willing to say yes if you present with right data and articulate it clearly.

Emily Leathers: Thanks. So okay, we've talked now about three things you should do ahead of time to prepare for a successful conversation, whether you already know this person well or it's the first time you're meeting with them. Now it's time for our fourth key to success: the meeting itself. For me, this whole key is just about good meeting hygiene. So these are a lot of reminders, but hopefully this is stuff you're already doing in a lot of your meetings. Shama, could you jump back in just one or two ways you've seen a conversation with an executive go off-track?

Shama Keskar: Yeah, I'm happy to. I would say that one of the key things, we kind of talked about it, is having crystal-clear data and all that. So I'm definitely going to reiterate on that, is if you present too much information clutter, definitely that could put your executive off, as they don't know which is critical and important. So having crystal-clear data and relevant metrics is critical. Another aspect would be if you're talking too much, talking too fast could put your executive off. They tend to lose focus because they don't know what's overall going on. Then another aspect I would say that if you are not clear with your ask, executives don't know what to guide you on. So these are some of the things that I would highlight here.

Shareen Islam: And I can add to that. Just keep it short, polished, concise. Just like Shama said, clear, high-level, because some executives you don't need to go into the weeds with them, and I think that's what it is, is when you're speaking to an executive, you want to keep it high-level.

Emily Leathers: Yeah, I love the data--information, not data--way of phrasing it, and I know then we then use information as part of how we think about, but ignore that part. It's like, tell people your conclusions and then be prepared to back them up, but don't walk through it and ask them to form their own. Michelle's comment in the chat is such a great way of saying a very similar thing, come already prepared with, this is how much it would cost. This person already says this is where you could pull the budget from. One of the things you're trying to do is build trust, and when you come prepared and having already thought through things, it's easier for them to trust you, which means it's more likely to get a yes because you're just turning off the fear and worry parts. And at the same time, you're asking them to make a decision they are actually capable of making, which is, "Can I move this budget from here to here?" rather than having to go out and do the research and figure out what it will take.

Michelle, I paraphrased a lot of what you said. Folks should go read it. So that wraps up our fourth key to success. Those keys were making sure you know the purpose of the conversation and what you want out of it, making sure you do your research on how the exec you're talking to likes to be communicated with and maybe any distractions or pitfalls, getting really explicit and precise ahead of time on the help you'd like from them if they're willing, and keeping great meeting hygiene.

We're now going to move over to all your questions. We've got a couple in the Q and A. Before we do, I just want to mention, as I said, we're going to send a Google doc out afterwards. There have been some awesome tips in the chat here. I'd love to go ahead and copy them into the doc. If you've put something in and you don't want me to share it, just comment in the chat by the end of this meeting and say, "Hey, please don't include my stuff." I'm not going to put names next to it unless--actually, I'll ask Karen if we should put names next to it or not. We should probably give people credit for their work. We'll sort that out later. Alright, I'm going to dive into the questions. Tina's was first. So what would we do if an executive was unclear if their meeting topic was "whatever's on your mind" or a "group one-on-one".

Those are hard. I can tell you how I think about those. Having been a participant and someone who's scheduled them, those are pulse checks on the org. So there are two things someone's generally trying to do there. They're trying to make sure you are healthy and happy and get an early indication of things that are going wrong. So think of those meetings like the error log that you read while you're looking at an online system, right? They're trying to figure out do the same topics come up over and over again, and are there just signals that tell them something's off they need to look into more deeply. And the second thing they want to know is how can they accelerate their org and make people happy? And I say those as the same thing. They really are the same thing. How can they help retain great people?

How can they help grow people, and how can they accelerate their project work? Your job in that meeting is to come in with three things. One, how do you want to present yourself? So you want one sentence with a couple of keywords that says who you are and what you're working on, and it should be your brand, basically. What are the three words you want them to remember when they think of you? The next is, is there anything that they should know, about anything that's concerning to you or worrying to you? And the third is a request. It's a meeting with an executive. Come in with your asks. When you tell them about the project and they say, how can I help? Have a really pithy exactly how you can help, and it should not be attending a 90-minute meeting later. It should be, can you forward this email? Can you get me in touch with this person? Can you reinforce this thing? Whatever. Don't make them think. Just make it easy for them to say yes. Shareen, Shama, other things you want to add to that one?

Shama Keskar: I would just add one more thing that, before the meeting, it's good if you could share something that will, if you're looking for a tangible outcome, share something that's going to help your executive navigate you better during one-on-one or in a meeting, and it could be any form of mechanism. You can use a quick update or quick introduction about yourself. So you use most of that time to discuss something that's on your mind with that executive. So I would say that share something ahead of time for sure.

Emily Leathers: Yeah, and have the thing you would send afterwards about your project already ready so you can send it 10 minutes after the meeting, after you've tailored it to the questions they ask, rather than at the end of the week. It just makes you look so good that you already had it. Shareen, it looks like you were going to jump in, too.

Shareen Islam: No, I think what you both said was great.

Emily Leathers: Perfect. And then from Nancy, how do you contribute to a conversation when people in leadership sometimes love to talk and there's no pause for you to talk, especially hard on video when someone doesn't always see the visual cues. I love this one.

Shama Keskar: Happy to take first stab at it. I've been in this situation as an engineering leader. I've also been in a situation where I was the only female leader. So I'm going to say that you just have to jump in. Definitely deep dive before you get into such a meeting. Dive deep, prepare yourself, think about pros and cons, and then jump in and wave or just say, "Hey, I have something," or something. Or knock on the table, do some gesture moment that will help people understand that you have something, or it's a video call, then you can put it in chat. You are doing like, hey everyone, or at everyone so everybody gets attention and you can make your point. So I would definitely say that these are some of the things have helped me and I always had good points to bring, and eventually what happened is people started respecting that she definitely is going to bring something tangible, something relevant to the table and I got opportunity to speak up without having to do any gesture or any funny moments.

Shareen Islam: [cross-talk] Sorry.

Emily Leathers: Yeah, Shireen.

Shareen Islam: No, I was going to say that sometimes you do have to kind of...exactly...make space for yourself, and so that's what it is. So if you're on a Zoom call, use the hands gesture and say, "Hey, my hands up," so your face is lit up. Make sure you're on camera so you're visible. Your presence is very important. Say something in chat. "Hey, I had a comment to say about that. That's a great point. I have something to say about it as well." If you're in the room, say, "Before you move on, I wanted to add on something." So make sure you insert yourself in the conversation. That takes confidence, and then this conference is about getting to that next level, and that's exactly what will get you to that next level. The more you speak up, the more visibility you get, the more people know you, that is what will get you to that next level.

And that is exactly what worked for me to get me to that next level. So all of the things that Shama said, those are the things that will get you there. So continue to speak up when you have something to say. You will be in rooms where these, and a lot of these execs, sometimes they're chummy with each other, and it's like the good old boys club, and you're there and you're trying to get in. It's hard, but have that confidence in yourself. Sometimes it does take stepping outside of your comfort zone to do that, but make sure you do do that.

Emily Leathers: Yeah, you're reminding me of the rooms I've been in where a bunch of folks, two levels above me went off on a side conversation about how this related to some other project they were on that I wasn't aware of and I was trying to figure out if that was an important thing for them to work through. And if the people who were talking about it were supporting my cause or if they were all just distracted and had forgotten about me. I promise you, the first one made me feel more confident than the second interpretation, regardless of which was true.

Yes, use the hand raise. One of the best things we ever did on my last team culture was everybody used it all the time. I used it when I wanted to speak up as the manager of the team. It showed a list, it made it much easier. We just got used to having the facilitator call folks in. Wielding notetaking. Now, if you're in Shama's position and you're with a bunch of your peers and you feel like there's a gender imbalance, you may not want to. But notetaking is an exceptionally powerful thing. If you are the person who's the project lead or the project owner in a meeting with a bunch of other folks, have visible notes you're taking, one. They want you to take notes on what they're saying. That's why you're there. That's why they're there. You can say, "Hey, I didn't quite catch that. Can you say it again?"

You can always jump in for that and it's super helpful. Perfect. Thanks, Karen. I was just about to ask you that. We have the okay to take another question after this one. And another element is just DM your manager. If there's someone else in that meeting who's in your management chain, you can say, "Hey, there's something I really want to say about this. Could you help me make some space?" Your manager in, basically every setting, is there to support you. You should feel free to delegate to them when you need them to be there, especially as that kind of emotional or traffic management support.

Okay, so we had one other great question in the chat from Lizzie. Do you have any advice for what to do if an exec takes a meeting in a very different direction than you thought it would go, and you don't actually have answers prepared, or you're not the right person to answer. So I love that those are actually three different scenarios. Let's say, who wants to jump in on those? Yeah, Shama, go for it.

Shama Keskar: Okay, great question. If it's going in a different direction, feel free to speak up and bring it back to the original agenda. If you believe that, if it's going in a different direction, but the discussion is definitely more relevant and productive, you can always chime in, interrupt, and say, "Hey, we are going in a different direction, but I believe this is equally important. I'm good with whatever the direction it's heading to. I'm not prepared for this direction. I need time to get back to you." One thing I've learned in my career is if you don't know something, just say it. I don't know, but I can. Or however I can dive into this research, or I know I'm aware of this, I can bring it to the table. So definitely be radically honest. Don't try to pretend because that's going to make you fall on your face. So I don't know is okay to say, and I forgot the last part of the question. Sorry, could you please help remind?

Emily Leathers: Yeah, absolutely. So when you don't have the answer, when it's something you do know the answer to, but it wasn't what you'd prepared your slides on or your collateral, was it that part?

Shama Keskar: Yeah, so basically I would say that if you know the answer and you are just not confident about it, it's okay to say that, "Hey, I believe I have the solution for this. I just need additional time to do whatever X, Y, Z, and then get back to you." I'm going to use Slack, email, or another follow-up meeting to do a follow-up on this. So those were my tips. Shareen?

Shareen Islam: Yeah, I would just say, "Hey, I don't have the answer for you right now, but I'll get back to you." Don't ever say no, but just say, I don't know right now, but I'll get back to you. Or the person that has this answer for you is not here, but I will follow up with them, and I'll get back to you. That's always okay to say, and if they're taking the meeting in a different direction, you can redirect them, and I think we talked about that earlier is you can say, that's not what this is about. I have that information for you. We'll talk about that in, I can have a one-on-one with you, or we can take that offline. I'd love to talk about that with you later. Let's talk about this right now. We can discuss that afterwards. We can kind of gently redirect them back, and it does. It's hard to do that with an executive, but it is doable.

Emily Leathers: In the spirit of Michelle's answer earlier about not putting more work onto that exec you're talking with, I loved what Shareen said a moment ago about, I'm not sure I'm the right person, but let me get you in touch with who is rather than you try to hear this name you've never heard out loud before. Spell it correctly and find them in Slack, and then figure out who they are and what to talk to them about. Sure, you can make that person do that, or you can do that tiny bit of extra work. Make a really good impression and make sure it's worth both of their time because you can give the intro on what the question is. Remember how we talked at the beginning about executives are often the person who's translating between the technical and non-technical or the marketing and non-marketing. You can be the person who creates those introductions and those translations. It's great skill practice for you. It creates a really good impression.

One other element you can do.... I guess not element you can do, but one other thing I would say is if you say, "Hey, I don't know. Let me go find the answer and come back to you," and you're in an organization where saying, I don't know, doesn't feel safe, please take that as a signal that this is a cultural problem in your org. Honestly, what I want to tell you is run screaming. If you ever don't feel psychologically safe saying, "I'm not sure, let me go away and come back with that in a timely manner," this is not an okay place to work for. Have that conversation with your manager. Have that conversation with a mentor. Sometimes we just need to increase our own sense of safety, but take the sense that there may be cultural things that are outside of yourself as well. There can be some serious industrial-strength gaslighting that makes us think that stuff's just about us when it's really about our org.

Alright, I think that's where our time wraps up. We want everybody to have a moment for a quick break in between sessions.