In this episode of Executive Connect, host Melissa Aarskaug sits down with Andrea Wasserman, Fortune 500 executive, advisor, and founder of The Executive Express, to talk about how leaders can give feedback to their boss, build trust with senior stakeholders, and grow their executive presence. Andrea breaks down what managing up really means, why timing matters, and how rising leaders can become strategic thought partners instead of just task executors. This conversation is for professionals who want to build influence at work, communicate with more confidence, and move from mid-level management into executive leadership. Andrea also shares how to handle a blocking boss, improve emotional intelligence, and create more visibility without overstepping.

Chapters:

(0:32) Why giving feedback to your boss feels risky

(2:55) What managing up really means

(4:05) Why timing matters in upward feedback

(6:13) How strategic thought partners think

(7:49) Building influence without stepping on toes

(9:42) What to do when your boss blocks access

(13:50) Three career accelerators for rising leaders

(17:04) Common blind spots that slow advancement

(18:46) A real executive success story

(22:14) Style flexing and executive presence

(25:12) Emotional intelligence tools for leaders

(27:28) Final advice on managing up

(28:00) What Andrea would tell her younger self

Andrea

(0:00) Part of being a strategic thought partner is asking the right questions and having the right information because if the first answer you have to anything anybody says is yes and you try to run off to do it without really thinking through the why and the context and the objectives and the parties involved, you’re not going to do a great job at it. (0:26) You’ll be checking things off but you won’t actually be moving the ball forward.

Melissa

(0:32) Ever feel like giving feedback to your boss is like offering a Yelp review to a volcano? (0:38) Yeah, dangerous territory. (0:40) But what if I told you there’s an actual science to it, a little art to influencing the org chart without actually blowing it up?

(0:49) On today’s Executive Connect podcast, we’re joined by Andrea Wasserman, Fortune 500 exec, thought partner and career whisperer to rising leaders. (1:01) She’s here to help us master the magic of managing up gracefully, effectively and without breaking a sweat. (1:10) Welcome, Andrea.

Andrea

(1:12) Thanks for having me, Melissa. (1:14) Happy to be here chatting about my favorite topics.

Melissa

(1:17) Now your career spans leadership roles across iconic brands and now you’re helping other leaders climb the ladder with intention. (1:29) What moment shaped your perspective on leadership and what inspired you to coach rising leaders towards executive level impact?

Andrea

(1:39) When I look back on the past 20 years of my career working across the types of brands and companies that you mentioned, spanning industries, the common denominator that I’ve noticed is that every organization, especially larger ones, has what feels like a secret combination lock that you really need to figure out to get ahead. (2:02) And oftentimes this lock has 18 digits on it and you turn one and the other one changes. (2:08) And so it really does require some amount of pattern recognition in knowing what to look for when you get into a company and want to succeed there.

(2:18) And once I realized that myself and enjoyed solving those challenges for myself and for people I was leading, I wanted to be able to do it at even greater scale through the work I’m doing now.

Melissa

(2:33) I love it. (2:34) And let’s just bust the myth. (2:37) Managing up isn’t about kissing up.

(2:41) It’s actually about strategic influence and communication within an organization. (2:47) How have you helped define managing up and why is it so crucial for leaders that want to advance their careers today?

Andrea

(2:55) Well, first, Melissa, you’re perfectly correct that managing up is about strategic influence and about communication. (3:03) It is also about timing. (3:06) And one key fact people need to understand is that managing up is not just about managing up directly to the person who is officially your boss on an organizational chart.

(3:17) It’s really about thinking through who are all of the senior stakeholders in an organization and how do I build relationships with them, influence them, make sure that I’m communicating my agenda and advocating for my team and the business and in a customer facing industry, the customer, and making sure that those conversations are happening in all directions.

Melissa

(3:42) Yeah, I know personally for me, giving feedback upward, it can feel very intimidating, you know, maybe like skydiving with a paper parachute, but what does your playbook look like when you’re offering this type of feedback and teaching senior leaders in a way that builds trust and doesn’t actually backfire in their face?

Andrea

(4:05) Sure. (4:06) There are a few key things that people need to understand. (4:09) One, as I mentioned, timing is very, very important.

(4:14) You really need to be thinking about when is the right moment to raise an issue. (4:20) It may be something that is a pressing item for you, but if it’s not top of mind or doesn’t need to be top of mind for your boss or somebody else more senior right now, then not only are they not going to really hear you, but they may actually be frustrated that you’re taking their time to raise something. (4:40) And so really assessing the situation and deciding, is this something that I want to communicate as a priority right now, or is there a better time to do it, or is there a better medium through which to do it?

(4:54) Maybe it is something that you need to get across through influence, but it’s not something that requires a meeting or that requires you are using precious airtime in an existing meeting for. (5:05) Maybe it’s an email, maybe it’s a drive-by in the hallway now that so many of us are back in office, but really thinking through not just what is a priority for you, but for others and for the business is going to be critical in demonstrating to people that you understand what they’re thinking about.

Melissa

(5:26) Ready to lead smarter and invest wiser? (5:29) On the Executive Connect podcast, we unpack executive strategies for wealth and influence. (5:37) Hit the subscribe button now.

(5:39) Don’t just watch, act. (5:41) Yeah. (5:41) And it popped into my head is the whole analogy, pick your battles.

(5:46) But I also find that I look at, in my career, I think of myself like a strategic thought partner across the organization in a lot of cases. (5:55) And I know from your experience as a fractional CXO and executive advisor, really what separates someone who simply executes a task or is a doer from somebody who is a more strategic thought partner?

Andrea

(6:13) The first part of being a strategic thought partner is asking the right questions and having the right information. (6:21) Because if the first answer you have to anything anybody says is yes, and you try to run off to do it without really thinking through the why and the context and the objectives and the parties involved, you’re not going to do a great job at it. (6:41) You’ll be checking things off your to-do list, but you won’t actually be moving the ball forward and being able to see around corners and proactively come up with the right approach if all you have are the basic facts.

(6:55) So starting out at the gate by asking those questions, the importance of that really can’t be overestimated.

Melissa

(7:03) Yeah, I love that. (7:04) I think being an ambitious self-starter and going out and doing whatever task is assigned is great, but it can also backfire if, like you said, you’re not clear about what you’re doing or how you’re doing it. (7:17) If things have been done one way forever, does it need to still be done the same way that in the new age, digital age, AI world we’re living in?

(7:29) So how can leaders or rising leaders show initiative and build influence internally without being seen as stepping on others’ toes or overstepping their manager to maybe talk to a senior executive? (7:44) Is there different tips you can share with our listeners?

Andrea

(7:49) Of course, nobody wants to be seen as stepping on toes or going around anybody on the organizational chart, and this is where communication is key. (7:59) What you’re doing and who you’re trying to talk to doesn’t need to be a secret and shouldn’t be a secret, but having a conversation with your boss and actually letting them know that you are taking the initiative to update their peers on something can actually be highly valued. (8:16) Now, of course, it depends on the personality and on the relationship that you have and on the dynamics between that person and other senior leaders, but actually taking those types of updates off your boss’s plate and saying, I’ll make sure to socialize this.

(8:32) Do you have any concerns? (8:33) Or I’ll make sure to socialize this. (8:35) Are there certain points of it that you think I should be highlighting?

(8:39) That can actually be really appreciated because it’s a time saver and it can be some political help.

Melissa

(8:46) And you’re collaborating and you’re being transparent and clear, which clear is kind, right? (8:52) And I love that. (8:54) I know I’ve had this happen in my career where a new leader was brought in that I reported to, and I had been at the organization for a while, and he was adamant that nobody was allowed to talk past his level.

(9:08) And so if I needed to talk to our CEO or another business leader, everything had to be through his words, his voice. (9:17) And I felt like no matter how hard I tried to get around that, it just became something so difficult to do that at some point, I just stopped doing it. (9:27) So can you share with those listeners who are in a similar situation, who have a boss that they give the information to and he presents and gets the credit?

(9:38) And what should they do in these kinds of situations?

Andrea

(9:42) Those situations where you have a boss sitting above you who just will not let you through are incredibly frustrating and really challenging because certainly a recipe for success is not going around a boss who has been clear that you should not do that. (9:57) And so I do not advise that. (10:01) I will tell you that I have a client right now who is looking for a new job because she has a boss like that.

(10:07) And so let this be a warning to leaders not to be that kind of blocker in an organization. (10:14) But in terms of what somebody can do who is not necessarily looking for a new job or doesn’t want to do that right away, think about who else in the organization you can naturally build relationships with. (10:26) In some cases, there may be peers who are really valuable to you.

(10:31) And so as much as we’re talking about managing up, I also don’t want us to gloss over the fact that pure relationships can be, first of all, just fun and collaborative and a great way to get your work done, but also can be useful in what’s channeled up to their bosses. (10:47) And so if you can’t get through to other people through yours, there are sometimes other ways of deftly doing that. (10:55) And don’t make it about you.

(10:57) Make it about the business and what various stakeholders need to know and what has to happen in order to best serve your customer, whether that’s a consumer or a business. (11:07) Because really that’s what’s valuable to people at the end of the day. (11:11) And so the more that you can depersonalize it from the relationships that you want to build in a company and really think about what’s best for your team, what’s best for your business, and I’ll say it again, what’s best for the customer, the more credit you will naturally get for being one business minded and thinking like a team player.

(11:32) The other point I’ll make on that in terms of what you can do just quickly is play the long game. (11:37) You may not be able to develop all of the relationships that you want, especially at senior levels in an organization today. (11:44) But even when you’re not in the room, often people know who really did the work.

(11:50) So yes, it’s disappointing and upsetting to be left out of rooms where your work is being presented. (11:56) But everybody is in that situation at some point. (12:00) And I would advise patience in most situations.

Melissa

(12:04) You literally took the words right out of my mouth. (12:06) I was going to say, take the emotion out of it because oftentimes you’re spot on. (12:11) It’s not you.

(12:12) What’s best for the company and stepping out of the emotion of it and really stepping into finding opportunities where you can be in the same room with your boss with some of the other executives and work through the dynamics face-to-face. (12:28) I know that’s helped me quite a bit working in face-to-face situations or putting myself in face-to-face situations has been really helpful as well. (12:38) I want to pivot a little bit and talk about maybe top three career accelerators for top players.

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Andrea

(13:50) One top accelerator is actually a great segue from what we’ve been talking about today, which is this notion of leading through influence and not just looking at the organizational chart and saying, these are the people who report to me and those are the only people I need to lead. (14:06) It’s really about thinking through what are all of the partnerships that I need in this company and how can I show that I’m a leader even potentially without the title today? (14:17) What are the ways that I can establish trust and relationships and align on goals and objectives and work with all of these people in ways that benefit my business and theirs.

(14:29) So that’s the first one. (14:31) The first accelerator is leading through influence. (14:33) The second is recognizing that perception is reality.

(14:38) What does that mean? (14:39) It means that you may be with your head down doing the right work all the time, but if you are not communicating it in the right way, nobody will really understand what you’re doing. (14:51) And so you may be a strategic thinker, but if you walk into a room and dive right into the weeds that the level of leader you’re talking to doesn’t care about, they will think that you’re not strategic, that you’re just an executor.

(15:05) So that’s one example. (15:07) Another is that you may be working on projects that are high priority for the organization, but if you bump into somebody in the elevator and you choose to headline something that is of a lesser priority, they are going to think that you’re not prioritizing the right things. (15:23) So again, that goes back to that statement, perception is reality, and that is the second accelerator.

(15:30) And the third that I would highlight is that it is never enough to just do your job. (15:35) So that should be a big takeaway for people. (15:38) The takeaway being it is never enough to just do your job.

(15:42) You really need to be thinking about what else can I do to add value here? (15:47) How can I get involved in projects without stepping on toes that are slightly outside my scope? (15:53) How can I raise my hand when there’s a new initiative that needs a leader?

(15:58) Those are the ways that you really start to build visibility in appropriate ways within an organization and accelerate your career forward.

Melissa

(16:06) Ooh, that’s so good. (16:08) I absolutely agree. (16:09) I think that is such…

(16:11) I got to re-echo what you just said. (16:12) I think showing up to just do marketing, if that’s your job, or sales, or engineering, or whatever your role is, and you’ve spot something within an organization that could be fixed or done better. (16:23) Maybe it’s cross vertical from where you’re working.

(16:27) You’re spot on. (16:27) Bring it up. (16:28) Try to execute it on your own and bring it to the company.

(16:33) I think that’s such a good piece of advice, Andrea, because I do think by doing that enough times, you’re seen as the person who can solve problems, break through different barriers, and really help the business move forward. (16:47) I absolutely agree. (16:48) I think that’s a great piece of advice.

(16:51) Now, I’m going to switch because we always talk about what works. (16:54) Tell me what doesn’t work. (16:56) What are areas, maybe blind spots, leaders have in today’s workforce that they should be paying attention to?

Andrea

(17:04) One is the importance of timing. (17:08) I have helped many people get raises and promotions over the years. (17:12) Certainly, I’ve sought my own.

(17:15) The biggest thing people need to know about asking how they can get ahead in the organization is that timing is everything. (17:23) If you are going to your boss and asking for a promotion when you just got one last quarter, it’s probably a bad time. (17:30) If you are raising your hand for a raise when the business is underperforming and specific pockets of responsibility that you have are underperforming, it’s probably a bad time.

(17:40) If you are asking for a raise or a promotion in just a really challenging business environment when your boss is under fire in a million ways, also a bad time. (17:51) And so that idea of timing is really where so many things can go wrong because you may have all of the right messages, but if you don’t choose your moment wisely, they are not going to land on friendly ears.

Melissa

(18:07) Exactly. (18:08) Building strategies and plans. (18:10) You don’t just want to execute without having a plan and understanding where the business is because, yeah, it’s spot on.

(18:17) It won’t happen. (18:19) They won’t be able to, and you’ll probably just get more irritated the more you keep asking. (18:24) So I love that.

(18:26) Now tell me about a time where you helped a fellow executive rise, like a success story. (18:34) Could you share with us a success story, maybe a mid-level leader who you helped support and they’re now thriving in executive leadership. (18:43) Do you have any success stories that you can share with us?

Andrea

(18:46) Yes. (18:47) One of my favorite ones is a fantastic employee who, like you suggested, was at a mid-level and more senior leaders really had this perception of her as being a junior player. (19:01) She had always put her head down, like I said, done the work, done a solid job at it, but first of all, had gotten caught up in some organizational politics that really weren’t her fault, but didn’t reflect well on her.

(19:14) And second, she was never in the right room, really presenting as an executive. (19:20) So she wasn’t seen as one. (19:22) And going back to what I said earlier in our conversation about every organization having these secret combination locks that need to be solved for, there were a couple in her company that related to who the personalities were at senior levels that really had become her blockers because they didn’t see her in that light.

(19:43) And also some of these lateral tensions with her peers. (19:48) And so resetting things from a relationship standpoint, both laterally and at more senior levels and helping give her the reasons to be in the right rooms and then give her the confidence and the executive presence skills to be speaking up appropriately in those rooms, positioned her finally for the promotion that she had been after for years.

Melissa

(20:12) Yeah. (20:12) I love that you brought that up because I think there is a certain finesse that’s required. (20:18) I hear a lot from other executive women leaders that they feel either they’re too soft or they’re too strong and they can’t really find that middle ground on how to drive whatever they’re driving.

(20:30) Yet be empathetic to their employees and also position themselves in a place of ability to do the role, ability to grow within the organization. (20:42) Oh, mind you, technology advances, technology changes, political changes. (20:47) So I hear a lot.

(20:48) I don’t know if you have any thoughts on how specific for women, how leaders can be all in with these initiatives while being empathetic to their people, while having their eye to the future. (21:04) It’s kind of like three different hats I feel like they’re wearing. (21:07) And like you said, the combinations change depending on the time of the year, the seasons, the verticals they’re in.

(21:14) So is there some specific framework that you share with leaders to follow or processes to follow? (21:22) So kind of going back to what you were saying originally, this leader that maybe couldn’t get a promotion because they just got one last quarter or they couldn’t get one because the business wasn’t doing great. (21:34) When is that right time to ask if you’ve been waiting a year goes by, two years, three years, when is the right time to kind of execute on that?

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Andrea

(22:14) So I hear a couple of questions in there and want to address both of them. (22:19) First, I love how you pointed out the internal tension between wanting to be nice and friendly and collaborative and also wanting to appear as the executive that you know you are. (22:31) And I think you had said, how do I recommend that people deal with that?

(22:34) One of my favorite terms that I use all the time is style flexing. (22:40) Some people have heard of this. (22:41) Some people haven’t.

(22:42) I’ll explain it. (22:43) What it means is that without being inauthentic to yourself, you can show up in different ways for different people. (22:52) And what this really requires is an understanding of who they are, what they’re expecting from you, and what their general personalities are.

(23:01) So for some people, you do want to come off as warm and fuzzy and they’re going to enjoy chatting with you for a while at the beginning of a meeting and sharing pictures of what they did over the weekend. (23:13) And for other people, it’s down to business right away. (23:17) And so if you approach somebody who is all business all the time in a chit-chatty way, that’s not going to go over well and they may see you as not being serious.

(23:26) And likewise, if you’re trying to establish a relationship with somebody who wants more of a connection with you and you completely skip over that and go right to the latest data, that’s not going to go very far with them. (23:42) And so really thinking about the different sides of yourself and how you can bring that out at different conference room tables in different ways is critical for making sure that you’re seen and perceived in the ways that you want to be. (23:58) And I do want to emphasize, it’s not about completely changing your personality depending on the audience.

(24:03) It is just choosing which components of your personality you want to be sharing with different people.

Melissa

(24:11) Oh, I love that. (24:13) Now, are there specific emotional intelligent tools that you suggest? (24:18) I know I hear a lot from my male colleagues who are leading engineering teams or they’re more the doers, the technical.

(24:28) They struggle sometimes being more empathetic to their teams and they get, just like you were saying, they get right in, they do the work, they talk about what’s broken, what needs to be fixed. (24:38) And so I do know some of those colleagues are working on increasing their emotional intelligence. (24:46) So do you have a specific framework or a specific place that those people can go that are trying to be more aware that maybe they show up too aggressively or maybe they show up and they’re really high energy and they’re maybe too abrasive and their staff is more introverted and quiet.

(25:05) Is there a specific place that you would recommend them going to learn how to be a better leader in this capacity?

Andrea

(25:12) There are a couple of books on emotional intelligence, literally with that title, that are really solid if people want to take an academic span and read up on it. (25:22) But I think for anybody who doesn’t want to do that, my best advice is to observe. (25:29) Observe absolutely everything, body language, tone of voice, speed.

(25:35) And notice if you’re new, for example, to working with certain people or to managing a new team, pay attention to the way that they react to you in different settings. (25:46) If you’re engaging by sharing what you did last night and asking them a personal, a more personal or social question, and they’re not really into it, you can tell that pretty quickly and you can move on to business. (26:01) And the opposite is true as well.

(26:03) So that’s an easy way to just remind yourself to be attuned in those conversations. (26:09) Another is just to ask. (26:11) I am known for, when I start managing new teams, really asking people how they want to work, what’s important to them, what has been productive and enjoyable for them with leaders in the past, and what hasn’t been.

(26:25) And people will be honest. (26:26) They’ll tell you if they just want to be efficient and want to get in and out of their meetings with you, or you’ll notice that they are more likely to hang around and want to get to know you a little bit more.

Melissa

(26:37) Yeah, I love that. (26:39) Something as basic as asking people how they want to be treated, it’s so rudimentary, but it’s like we don’t do it, right? (26:48) We’re so busy on doing the job or doing the task that we just, you know, the world’s becoming more transactional, right?

(26:54) So we, we show up doing the transaction, not meaning to be malicious or non-empathetic or not hardworking, just that’s how we’re trained and ingrained to show up is, you know, this is my role. (27:07) This is what I do. (27:08) But I love that you said that just asking as simple as that is such, such a rewarding and great suggestion.

(27:18) I want to get any other final thoughts or anything that you want to leave with our listeners as it relates to managing up that we didn’t talk about today.

Andrea

(27:28) In terms of managing up, I really just want to reiterate to be open-minded about who you’re trying to influence, how you’re doing it, and making sure that you’re seeking feedback too. (27:41) It’s not a one-way street.

Melissa

(27:45) I love it. (27:45) Now tell me, okay, so I’ve been doing this lately. (27:48) Tell me if you could tell Andrea, your younger self, or leave her with one piece of advice you knew you had when you first started your career, what would that piece of advice be?

Andrea

(28:00) A piece of advice for my younger self would be don’t try to plan out every step of your career because many of the roles that you may have probably don’t even exist today.

Melissa

(28:12) So true. (28:13) Such a great piece of advice. (28:15) Andrea, tell our listeners, what is the best way to connect with you and learn more about how they can manage up and turning their career strategy into a gold mine?

(28:28) Where should they connect with you on?

Andrea

(28:30) They can visit my website, theexecutiveexpress.com. (28:34) I offer free consultations there. (28:36) They can follow me on LinkedIn at Andrea Wasserman or on Instagram and TikTok at The Executive Express, and I’m on YouTube too.

(28:46) I love it.

Melissa

(28:47) Thank you so much for being here today, Andrea, and sharing your time and knowledge with our listeners. (28:54) That’s The Executive Connect Podcast.