in: Career, Career & Wealth, Podcast

• Last updated: May 30, 2023

Podcast #899: The Essential Guide to Getting Promoted

Have you been languishing in the same role at work, frustrated that you haven’t been promoted to a higher position with more pay and different responsibilities?

My guest can help you level up in your career. His name is Randy Ornstein, and he’s the author of Grow: The Essential Guide to Getting Promoted. Today on the show, Randy explains why getting promoted is more beneficial to your paycheck than getting a raise and his case for why you should stick with working for the same company for a long time. We then talk about the things you need to do so that management thinks of you the next time a higher position opens up. We discuss how promotable employees participate in meetings, execute their communication, study their work, and develop best practices. We also talk about when to bring up the idea of being promoted to your boss and a couple of the challenges that can come with advancing up the ranks.

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Read the Transcript

Brett McKay: Brett McKay here, and welcome to another edition of The Art of Manliness podcast. Have you been languishing in the same role at work, frustrated that you haven’t been promoted to a higher position with more pay and different responsibilities? My guest can help you level up in your career. His name is Randy Ornstein, and he’s the author of Grow: The Essential Guide to Getting Promoted. Today on the show, Randy explains why getting promoted is more beneficial to your paycheck than getting a raise, and his case for why you should stick with working for the same company for a long time. We then talk about the things you need to do so that management thinks of you the next time a higher position opens up. We discuss how promotable employees participate in meetings, execute their communication, study their work, and develop best practices. We also talk about when to bring up the idea of being promoted to your boss and a couple of the challenges that can come with advancing up the ranks. After the show’s over, check out show notes at

Alright, Randy Ornstein, welcome to the show.

Randy Ornstein: Thank you, Brett, appreciate it. Thanks for having me.

Brett McKay: So you got a new book out, it’s called Grow: The Essential Guide to Getting Promoted. What led you to write a book about getting promotions at work?

Randy Ornstein: Yeah, it’s been a very exciting, process writing this book, but throughout my career, mainly in beverages, I was promoted nine times over my career, and seven of those times at Anheuser-Busch within a 15-year period. And for me, after a few of those promotions when I was younger, it became a game to me of like how could I continue to grow up the corporate ladder and be successful at this amazing company, and earlier on in my career and when I was low 20s, I would see that the vice presidents had their own offices and even gold plates that had their names on it, and I was like, “Oh my God, how could I ever get to that level?” I didn’t think I had it in me, and I think I kept getting more confidence when I got promotions early on. I don’t think I was doing anything spectacular, but I guess I was doing enough to wow my boss and be the best person for the next position. And so as I’ve moved up the corporate ladder at Anheuser-Busch and people started to notice, I was periodically asked by this guy who led this program, where he hired roughly 30 college graduates every year to join Anheuser-Busch.

They would go through a six month training program, and at the end of the program there was a graduation, and I was asked to give the keynote speech to talk about how I moved up and got promoted at Anheuser-Busch and some tips to succeed, and I did this speech a few times throughout my career. I would usually have just five tips. I’d have one slide with like, “Here’s five tips I learned at Anheuser-Busch to get promoted,” and one would be, data is power, and I would talk about how I use data effectively with my time working with Walmart, or Kroger, or Target. And one would be, be persistent, and I talk about how I was very persistent with the people that I worked with. And years later, those individuals would come up to me at different meetings or happy hours and say, Randy, “I still remember those five tips that you gave me and they’ve really helped me throughout my career,” and it happened over and over again, and it just stuck, and it got me thinking I should formalize this much better and write a book about them and share them with the world.

Brett McKay: Yeah, no, I think it’s interesting, you point out at the beginning of your book, a lot of career books and business how-to books and articles they focus on how to get raises at work, which that’s good. But you make the case that there’s a benefit to thinking about how to get a promotion instead of just thinking about how to get a raise. So what are the benefits of thinking about and pursuing promotions within your company instead of just thinking about how can I get a raise?

Randy Ornstein: Yeah. Well, first of all, promotions are more monetarily valued at, so usually a promotion means that you get in the range of a 10%, 15%, 20% raise, versus your annual raise that you might get is usually between 2% and 4%. So think about it, if you were to just get a raise in your current job, it would take you like four, five years to get to the same value, had you moved up one level in your company. Plus, when you get a promotion and you move up you’re typically getting a bigger bonus and more equity in that company, as well, and so a promotion means moving up a level, getting more responsibility, potentially managing people, as well. And if money is one of those factors that you’re looking to do, you’re gonna make a lot more money in a promotion than just a regular annual raise.

Brett McKay: And I imagine too, it gives you new opportunities for growth, you get to do things you didn’t get to do at your previous level, and there’s value in that as well for some people.

Randy Ornstein: Exactly. You wanna understand more aspects of your business versus just maybe the niche that you’re in today and so typically as you are promoted more responsibility, maybe more hours but you’re also working with more leadership, and when you work with more leadership that are also not just in your department but different departments, that gives you more opportunities to grow as new jobs open up.

Brett McKay: So I’ve seen these articles, and I’m sure other people have seen these articles too, about how employees should switch employers more often because it’ll increase their chances of making more money. So the idea is if you switch employers, you’ll usually get a pay bump, but you highlight there are benefits of sticking with a single company and climbing up the corporate ladder. What are those benefits, do you think?

Randy Ornstein: Yeah, I definitely disagree with those articles that you should continue to move to different companies and get more money, and while maybe that’s true that you could get a bigger salary, you’re building no loyalty with the companies that you work with, and when you constantly switch companies every two three years, you’re not even getting enough knowledge in that current company to really deep dive and figure out everything you need to do to be successful. When I interview people for different jobs and I look at their resume, and I see that they had a job every two years, and maybe five jobs over 10 years with five different companies, I’m not gonna hire that person because why should I bring on a person for just two years knowing that after two years they’re gonna get bored and move somewhere else?

And one aspect is maybe they’re moving to different companies because they can’t get promoted in the current company, and their only way to grow is to switch companies, which is not what I look for in a team member or someone to join my team, so I’m looking for loyalty. When I’m looking to hire someone I’m thinking, in five, 10 years, could they eventually take my role? You’re always trying to find better talent, and you do build, in the end, long-term money, because the longer you stay with the existing company the more equity stock options that you would build within that company. If you left ever a few years most likely the equity that you potentially would have got would not be worth anything because they have not vested in time or worth anything, and so definitely value building your career, staying with one, two companies throughout.

Brett McKay: What would you say to the argument. I’ve seen, too, I’ve read of people like, “Well, I’m not gonna be loyal to a company because that company would just laid me off if they had to, so why should I have that?” What would you say to that? What Would you be a response to that?

Randy Ornstein: Yes, layoffs have been frequent, but I think it’s… Not everyone gets laid off, and there’s always strategies of… I’m not gonna be laying off my best talent, and so if you are a strong worker, you’re building good relationships, the chances of you getting laid off are gonna be much slimmer than others, and so if you believe in the company that you work for, which you need to do, and you think there’s a good career mobility for you, then I would stick it out. But if you’re joining a company and you’re just not excited then, yeah, maybe there’s an opportunity to move somewhere else, but to move to companies every two to three years, it’s just not a recipe for success.

Brett McKay: Yeah, I imagine it could take five, 10 years to really understand what the company is doing for you to actually have success. It’s like you see this with… I get really frustrated with sports teams, they’ll hire a coach, and then if the coach doesn’t produce results in a year, they fire them, and I’m like, man, you need two, three, maybe even more than that to establish a system, introduced the system through all of the levels, not just the players, but with the rest of the staff. It could take five years before you can turn a team around. I hate how it’s just like, “Well, you didn’t give us results right away, you’re done,” but it takes time to get results.

Randy Ornstein: Exactly, and it’s the same in business. I’m building a team right now at Gopuff where I work, and I brought in some really good talent back in the end of 2021, and it takes them six months plus to get used to the systems that we have and the changes versus their prior company. And so now the bulk of my team has been here a year, a year and a half, we’re just getting our groove, and now we’re having a really good year. And so in business it takes time too, you gotta build the team, you gotta train them. There’s always gonna be a little bit of turnover where you’re constantly training, but it takes time, but not everyone thinks that way, and they’re just reacting quicker than they want, and that just is not a recipe for success.

Brett McKay: Alright, so let’s talk about what someone can do to increase their chances of getting a promotion. You cite research that job performance is one of the factors most associated with moving up in a job. So in the first part of your book, you give tips on better performance, doing the everyday things of your job excellently. So let’s talk about some of the areas of work you can get better in, starting with meetings. A lot of people, they hate meetings, but they’re sometimes a necessary part of corporate life, so what can you do to get more out of your meetings, so you can get promotions?

Randy Ornstein: Yeah, I’m in meetings all day. It’s like straight. Sometimes I don’t even have a break to eat lunch, it’s the way we live, the world we live. We’re half virtual, half in person, and so I could be sitting on Zoom calls throughout the day, and it’s important that, number one, you speak up. You’re not just like another person on that Zoom call or in-person, that’s half listening, half working, and you’re adding no value. So it’s really important that if you’re in a meeting, you’re paying attention, you’re listening to the speaker, you’re asking questions, or giving comments, or providing feedback on how to improve. So the people know that you’re there, you’re adding value, you’re listening, you’re learning, you’re changing processes. I have many team meetings with my team, usually a Monday and Friday team meeting and then sporadic ones throughout the week, and I know which people speak up every time because they do it, and I also notice which people haven’t said a thing in six weeks, eight weeks. And that’s in my head as we do employee reviews in the next cycle, I’m asking why aren’t they speaking up, are they even listening to what I say? And so I think it’s a pretty easy thing.

You’ll get noticed as you add value in meetings, and so you gotta pay attention, you get off, stop working, think of questions to ask. Even if you can’t get a question out if you’re on Zoom, tap it into the chat, or even send a note to the organizer after the meeting, and same in person, raise your hand and speak up. Don’t be afraid and just do it.

Brett McKay: And of course, you wanna speak up and provide value, just don’t wanna speak up just to take up air space.

Randy Ornstein: Right.

Brett McKay: That can get annoyed if you do that, yeah.

Randy Ornstein: It could be, I think, do it once in a while, that’s fine. Even if you’re agreeing with something, but you also don’t need to agree every time to everything that people say. You could push back. I value the people that don’t agree with what I say, but they also then provide a better solution to what I said, and I appreciate that.

Brett McKay: Yeah, you talk about in the book, one of the frustrating things you have when you have a meeting where you’re looking for feedback, you’re looking for devil’s advocates saying, “What’s wrong with this thing?” And no one says anything. You’re like, “Oh jeez, this is not helpful guys, I need you to push back against me.”

Randy Ornstein: Yeah, I think it’s okay. I’m not all knowing nor is anyone all knowing. We all have diverse backgrounds, we all have unique experiences that we could add, I’m usually giving my perspective which could completely be wrong, and I own that, and I’m expecting the team to challenge me if I have something that I’m presenting that’s incorrect or inaccurate, or if they have a better way, like that’s the only way we’re gonna get better, is if the cross-functional or the diverse group comes together and builds together versus one person saying how it is and that’s it.

Brett McKay: I think a lot of people might be afraid of speaking up or being contradictory because, “Well, I don’t wanna cause a scene, or it might upset my boss,” but I think you just gotta kind of throw caution to the wind and just go for it. And you can do this in a collegial way you don’t have to be a jerk about it. Like you said, point out the issue and then propose a solution.

Randy Ornstein: I think the younger people are less apt to speaking up because usually they’re in lower roles and they might think that only the more senior people need to speak up. That’s 100% not true. I have different age groups, different genders on my team, different experiences, and I wanna hear from all types, because even the younger consumer or the younger person on our team has a completely different experience than someone that’s 20 years older with kids and a family and versus the single. When we deal with my line of business where I manage the alcohol business at Gopuff, our core consumers are lot younger than the average, and so it’s important to hear from anyone, no matter their level, no matter their age. And you just gotta do it. It’s just… Yeah, even if you’re shy, it’s important. If you truly wanna get noticed and move up the ladder, you can’t be a silent person, just sitting in meetings, half paying attention and not adding value.

Brett McKay: Okay, so meetings, you might hate them, but they’re a necessary part of your job, so get the most out of them. Another part of people’s job that they hate is communications, sort of like email, phone calls, Slack, texts, but you said you gotta excel at this stuff. So what’s your advice on managing work communication?

Randy Ornstein: I think it’s like staying on top of your messages. And we all get a lot of emails… I think we get less phone calls than ever, it’s now Tech, Slack and Email. I know Walmart had a rule of thumb called The Sundown Rule, where every buyer was requested to respond to their suppliers by the end of the day, so there was like a 24-hour rule. I’ve never operated with the rule, nor has any company I worked with. I think it’s common courtesy though, that when a supplier or an internal person is contacting you for something or asking you for something, even if it’s a no, you should respond back in 24 or 48 hours versus that person constantly re-emailing them every few days and you’re just deleting it or not responding. To me, it’s common courtesy. I would expect the same if I’m trying to sell to someone or sending an email to someone, I wanna make sure that I get a response back in a timely manner.

Certainly, there’s always issues where someone’s on vacation or someone’s really working on a busy project. But one way to get around this, if you do have a very busy schedule is schedule a meeting with yourself for 30 minutes a day or every two days where you’re literally focused on responding to the communications that you got. I think Slack is a little bit more instantaneous. We use Slack for internal, and so if you hadn’t respond to a Slack message from your boss in 24 hours, that would be a no-no. You’re expected to have Slack up on your screen and responding all the time. It doesn’t mean you need to respond within a minute, but you just gotta stay on top of it, and that’s how we get business done. If you’re not communicative and you’re not following up, it’s very hard, and so it’s gotta be part of the way that you work, and you have to manage that responsibly.

Brett McKay: And you give some advice on how to manage this stuff, so there’s tips on putting acronyms in the headlines, so that people know, “Well, this is just for information, you don’t have to respond.” You don’t wanna do the thing where it’s like a one-word response, “Thanks.” You just wasted everyone’s time with that and you’re wasting your time responding with things.

Randy Ornstein: I’m not a fan of someone responding thanks or one word as a response, and then like five other people then do it, and now you have like six emails that are just wasting your time. And so if you are gonna respond to an email where you’re writing, “Thank you for the information,” explain why you’re thanking them. Go a little bit more in depth. Or if you do have an important email that you’re sending to a client or your boss, make sure that in the header it says, “Action, I need a response,” and then highlight in the email exactly which question, just so you could cut through a little bit of the clutter, especially if you need something urgent. So definitely, the way you write your emails, don’t write a whole novel, bullet point them better, and if you need something urgently responded to put a note in the header.

Brett McKay: Yeah, the bullet points. I do that with emails and I keep the bullet points, if it’s like more than three, it’s probably, I need to get on the phone and discuss this. ‘Cause it’d solve the problem a lot faster just getting on the phone, and just hashing it out instead of having the person respond to like 10 different bullet points. And you’re a big proponent of the telephone too, if you need something right away or the problem is too complex for Slack or email, don’t be afraid of the telephone. And that might be hard for younger workers who aren’t, it’s not something they do a lot, but the phone can be really powerful.

Randy Ornstein: Yeah. You sort of just said it a minute ago, why would you need to waste time writing a long email, it’ll take you an hour to write it versus just picking up the phone and talking for five minutes. You just saved yourself a bunch of time. And in Slack, and we use it internally but we could quickly Zoom or huddle with internal people, external people a little tougher. You got to text or call. But yeah, definitely, I’ve noticed that over the years, the people that, at least from my suppliers that call me are on the older side because that’s like what they’re used to doing. And the younger suppliers, they’re more for email. So phone is not lost. It’s important, it’s important to build relationships and you just gotta do it.

Brett McKay: We’re gonna take a quick break for a word from our sponsors.

And now back to the show. So be good at communication, that will make your boss’s job easier. Staying on top of your communication will get you noticed. Another thing you talk about is studying, you have to study a lot. On the job studying. What do you mean by that and how will that help someone get a promotion?

Randy Ornstein: Yeah, definitely knowing your numbers is point number one. So if you’re in a sales role, let’s pretend I’m a supplier selling an ice tea brand. I wanna make sure that I know all of the numbers of my performance. So what are my weekly sales? Which metro is growing the most? Which of the retailers am I in have the best performance? If I’ve been selling for a few years how’s my performance versus last year? What is my distribution? What is my price point? How is it compared versus competition? And these are numbers that you should know. If you’re in an elevator with your boss and they’re like, how’s your performance or how’s your business? You should be able to recite that in 30 seconds a minute without saying, oh, let me get back to you. And if you say that, that’s like a telltale sign that you don’t know your business.

You should be an expert on what you sell or what you manage. In my work, as I mentioned, I manage the alcohol business at Gopuff, I need to understand how does beer perform versus wine versus spirits. And then every week, which of those three is growing faster than the others? And then if spirits is growing faster, is it coming from vodka or tequila? And then if vodka’s growing the most, then which brands is growing it? Is it Tito’s or SVEDKA? And then you keep going down and then which market? And so every company that I’ve been a part of has had like a weekly performance review where you’re usually reporting back to your management or boss about your performance, where are your gaps and how you can improve them. And it’s an, it’s really important that you understand the business that you work in.

And so by doing that, you need to study. You should have, depending on the systems that you have, we have a tool called Looker where we have all these automated reports that we could pull up and I could see all of my weekly sales. I could look at syndicated data like IRI or Nielsen to understand how my business is performing versus competition. And I set aside time every week to review those reports to make sure that I’m familiar because I’m constantly getting questions from management on what happened. And I wanna be able to answer them. And I’m also constantly asking my team what happened as they even get more into the weeds, the beer team’s gonna even get deeper into beer and they’re gonna provide me insights as well so that I could then be able to provide management if those questions are asked. So it’s a huge for me, number one, it’s knowing your business, but you gotta study to know your business and you just gotta take the time to do it.

Brett McKay: Okay, so this could apply if you’re in sales, if you’re a project manager, know the numbers, what’s the status of your project? If a boss asks what’s going on, you don’t wanna say, well, I don’t know, you gotta know that stuff. So study what’s going on inside your company. But then also you talk about, you mentioned study what’s going outside, what are trends that are happening in your area of expertise. And how can you utilize that for your division or what you’re in charge of.

Randy Ornstein: 100%. It’s not even just looking at data, but if I use the example of selling an iced tea brand, I gotta go to Whole Foods or Publix or Kroger or different grocery stores or convenience stores when I have time just to see what are they doing, what different brands are out there. I’m going on social media and seeing what people are drinking. The syndicated data helps you look at actual data to see which brands are growing faster than the average. And so it’s really important not just to know your own business, but then what are your competitors doing if you have competitors as well. Because in the end, we all wanna be the best. And so it’s important that you understand what they’re doing so you can beat them at their own game.

Brett McKay: So the second half of your book you talk about, going above and beyond the everyday stuff to get a promotion. And one of those ways you can go above and beyond is developing best practices for your company. So what do you mean by a best practice?

Randy Ornstein: Yeah, a best practice is something that saves you time, saves you money, or brings in more dollars. And it could be anything. It could be as simple as combining two Excel reports into one. It could be more complex as developing, working with your IT department to develop a new process that your suppliers use that makes things move faster. One example that I could think of on the team that I manage is a cost collection process that we have with our wholesalers for alcohol, where an individual on my team developed like this monthly cost collection process through this Jotform where suppliers now could go in monthly and update costs and it comes to us in the same manner every single time. Versus just telling our wholesalers to give us costs changes when something increases. And we have all these different formats and it takes time to put it all together.

And so we condensed the process and it was a free thing. You don’t have to add, you don’t have to create or put a budget together. It was just something that we put together and now it reduces the time that it takes to accept these costs in half. And so a best practice is not always given to you. I expect the team to come up with best practices that will help make their job easier. Sometimes it’s given to you, there could be a project given where we like, hey, we need to reduce our budget by a $1 million, but grow our sales by a $1 million how would you do that? And then that’s a session, but I expect that you’re constantly thinking of ways to make your job better, easier, smarter, so that you could work on new things to drive results. And I call that a best practice.

Brett McKay: So find problems within your company and solve them. Do you need a wait around, should you ask for permission to start or sometimes you just like, I see this issue, I’m just gonna solve it right now and create a best practice for it.

Randy Ornstein: Yeah, I think most of the times you don’t need permission assuming that it’s a no budget best practice. If the practice that you’re putting together requires a budget that definitely would need to get your management involved as that has to go through a budget review process and there needs to be checks and balances as well and checkpoints to ensure that you’re working through it and that money that you received, you’re actually putting to good use. But most of the times and what I appreciate the most, if I’m meeting with someone on my team, they’ve already showed me, they’re like, hey, I saw this issue. Here’s what I did and here’s the result. Versus even the reverse, they’re telling me of an issue but they’re not giving me a solution how to fix it. And so the person that was proactive they actually developed it, they already met with the team, they put it together and here’s the results. To me, that’s a person that is desired to moved up the ladder.

Brett McKay: You also talk about it’s important for employees to get better at asking for things in order to get a promotion. Why is that?

Randy Ornstein: Yeah, I think you need to constantly be open with your boss. I would recommend that you have a weekly touchpoint with them where you’re typically going over projects that you’re working on. That’s usually what you would do in that meeting. But then maybe once a month you’re talking more about your own individual performance and if there’s an issue, what do you need to fix that issue? And quite frankly, a lot of times it’s something that requires more funding. Maybe it’s more IT help, maybe it’s a headcount, if you don’t ask for those things, it’s hard for your management to know what you actually need and by asking and saying, here’s what I need to be successful, and yes it might cost money, but here’s what I need. It makes you think, okay, this person really is trying to improve this process and you need to ask for it.

Don’t just sit there, do your job and say, oh, I can’t do that project or initiative because I don’t have the resources. You need to speak up and ask for it. You might not get it every time. There’s always things going on in the company that is tougher. But if you’re vocal about it and you explain why you need it, the benefit from it, the ROI from it, I would say more than often you’ll get the yes to get those resources and you would expect the same when you’re in that same position as well from your people under you.

Brett McKay: You talk about the role of mentors can play in helping secure promotions. What does that look like?

Randy Ornstein: Yeah, I think mentors are very important and I think less and less companies today have a true mentorship program. So it’s really on you to find that mentor to help guide you. It’s definitely not your boss. It’s either someone that you’ve looked up to throughout your career or maybe it’s someone that’s moved to a different company but maybe was your boss at the time. I think they will help you, especially if the mentor’s in your own company, they could help open doors for you. So you could be probably a lot more open with them than your current line manager of like, this is what I really wanted to try and join the supply chain or operations team, but I’m on sales and it’s hard for me to make the shift. And maybe that person could help introduce you to people or find connections for you or introduce you to people outside of different organizations. I just think that they could open up a lot more doors assuming that they value the mentor/mentee relationship.

They’ve also most likely built very strong relationships with other people. And I’ve had three or four mentors throughout my career that nothing was a formal process where I would meet with them monthly. It was just like they were a mentor of mine when I needed anything I could call them or text them, hey, do you have 15 minutes to talk about this? And they would give me advice and I valued that advice and now I’m able to pay it back. And I have different mentees, you could call it, some in my current company but some throughout prior companies that I’ve worked for that do the same thing. They ask me questions, they’re like, hey I’m thinking of leaving my current company and here’s the jobs I’m looking at. Or I’ve been in my role for three years. I wanna get a promotion. What do I need to do to move up the ladder? And so I think it helps tone your skills, whether you’re a mentor or a mentee and then helps you in your career as now I manage people, I’m giving employer reviews, I’m able to use some of the skills I have of how I’m mentoring people in the same way.

Brett McKay: Okay, so you don’t want your boss to be your mentor, but how do you know or how do you figure out that someone could be a good mentor? Are there traits or characteristics you’re looking for in a potential mentor?

Randy Ornstein: Well, I think it’s gotta be someone that you have a good relationship with that is not someone that maybe you think could be a good mentor, but every time you try and talk to them, they have no time for you. They need to make the time, they need to value the mentor/mentee partnership. Who do you connect with? Maybe you’re at a team function out traveling and you just connect some with someone. Maybe you’re both runners and you happen to run together in the mornings before meetings when you’re traveling. It depends, you gotta build a connection and I think they should always be a level or two higher than you ’cause you wanna, certainly you’re trying to aspire to move up. You wanna have someone that’s got a little bit more experience that also knows more of the leadership because when you’re trying to get a new job or you’re applying for a new position within your company, that mentor could hopefully help you as well by talking to the hiring manager if they know them and putting in a good word for you, even though that person might not have directly worked with you every day.

Brett McKay: You also talk about the importance of being flexible about where you live to increase your chances of getting promotion. How can that help you get a promotion?

Randy Ornstein: Yeah, it certainly depends on your company. If your company only has one office and everyone lives in that one office, then usually relocating is not an option. But for a company like Anheuser-Busch that I worked for in the past where we sell Anheuser-Busch products basically throughout the world, you need to be able to move sometimes to move to get promoted. I had to move to Bentonville, Arkansas to work with Walmart, the largest retailer out there. I could not have worked with that retailer if I didn’t live in Arkansas. That was a demand by the retailer that their suppliers need to live there. And that was probably the best decision I’ve ever made on my career moving to a town I’d never been to, but working with this amazing retailer that while stressful at times is the leader and I gain so much experience from it.

And so you also gain a lot more experiences moving to different towns, whether they’re small or large. You’re building more relationships as well with different people. Yeah, it’s tough. I moved a lot more when I was younger. I think I’ve moved seven times now, but now I live outside of Philadelphia. I have two kids that are in elementary school and it would be tougher in my career right now to move for a job unless it really meant a significant increase in role, monetary value to make it worth it. It’s not for everyone but the companies that are national or global that have offices throughout the country, if you wanna gain new experiences, the one way to do that is to relocate where the office is.

Brett McKay: Okay. Let’s say you’ve been doing all this stuff. You’ve been making the everyday excellent going above and beyond by establishing best practices, getting the mentor, things like that. At what point do you bring up the idea of a promotion to your boss?

Randy Ornstein: Well, it’s definitely not after three months in that role. And quite frankly that happens all too often. The person thinks, oh, I’ve been in the role three months, I’m crushing it, I’m ready for the next step. But you have to be strategic. So, every company I’ve worked for has had an annual performance review. So certainly during that annual performance review you should be talking about what you need to do to move to the next level. But periodically during your one-on-ones with bosses, you should also be bringing that up because you don’t need to talk about this just once a year, but you also don’t need to be talking about it once a week. So depending on the style of your boss and how you work, every one, two months you should be gauging how am I doing? Am I doing all the right things?

And then if you’ve been in role two, three years and you see no signs that you’re gonna be promoted, you need to be vocal and what am I doing that is not causing me to move up or what should I be doing to help? Especially if you see other people moving up that have been in a role less than you. So you don’t wanna be that person that’s every week, when am I getting promoted? When I’m be getting promoted? ‘Cause then it gets annoying and then you get turned off. But it needs to be an ongoing discussion. But excel on your job first after three, six months is not the time. That’s too soon.

Brett McKay: Okay. And also be having these check-ins periodically throughout the year so your boss is aware of what you’re doing. Is there documentation that you should be keeping track of just on a daily basis so that when you go to that performance review you can say, well, here are the things that I’ve done.

Randy Ornstein: I think everyone does it differently. What I would advise is, and I just did this a month ago. We had our performance review process and you have to write down all of your accomplishments that you had. It’s very hard to think of everything you did in 2022. And so yes, if you wanna have your own document that you’re constantly updating with a best practice you implemented or a success that you had or something that you think would be valuable for that employee review, it would be helpful if you document it or saved an email where you had a very good response from your boss on, so that when you do write your employee review you’re basically copying, pasting the information versus trying to think and most likely you will forget things. And so I’ve never seen it as a formal process. It’s up to you depending on if you think you can remember or not. But I would definitely do that.

Brett McKay: I know you didn’t discuss this in the book, but I just thought about this. Let’s say you get the promotion, in your experience of getting promotions and then overseeing the promotions of employees that you oversaw, what are the biggest challenges you have when you first start off in your new position, in your new role in that promotion? What have you seen?

Randy Ornstein: One big challenge is the transition from old job to new job. Typically when you’re in the new job, you’re still doing work of the old job until they’ve hired a replacement and then when they’ve hired the replacement, it’s your responsibility to usually train that person and start moving your old work to that person. ‘Cause if you never do that then your workload’s just gonna continue to grow. And so you need to do that. You need to, again, depending on what type of role you’re moving into, you gotta shift and as you move up you gotta start delegating. So when I give workout to employees, especially my senior employees, I might give them a project but I’m not expecting them to do 100% of that project. I’m expecting them to then work with their team to do the project together. And I do see some people that have delegation issues where they like to take full ownership and not delegate and the people that delegate are the people that have more time to do other things. So it’s definitely making sure you transition properly your old job to hopefully the new person that got hired and then properly delegating work that you might get.

Brett McKay: Have you had any problems with, let’s say you were in a role and you had colleagues who were on equal footing. In the hierarchy, then you get the promotion and now you’re overseeing this person that was once your colleague and maybe you’re even friends. Was there any friction there? Does that dynamic can that throw you off?

Randy Ornstein: Yeah, it’s happened many times throughout my career for sure. And I would say it’s a little awkward in the beginning but once you get past the awkward phase, let it be known that yes we are friends but now this is a manager/employee relationship, you just gotta make it work and if that person can’t make it work, then they’ll find another job or they’ll leave the company. It doesn’t mean that you can’t still be friends with that person outside of work and do things, but you have to accept the role that now the two people are in and just live with it. And I’ve had a scenario where I used to be a direct report of my boss and then later on I then was the boss of that person and yeah, it’s awkward for a week or two but you get past it and you get down to business just like it really never existed. [chuckle]

Brett McKay: Right. You gotta be professional, keep it professional.

Randy Ornstein: You gotta be professional. Exactly.

Brett McKay: Well, Randy, this has been a great conversation. Where can people go to learn more about the book and your work?

Randy Ornstein: Yeah, well, definitely my wife, Hayley and I wrote, the book, Grow: The Essential Guide to Getting Promoted. It’s on Amazon, You can look at Walmart and, we have all three formats, so paperback, e-book and now audio version. So depending on how you like to read, we have a version for you. You could find me [email protected] or just LinkedIn. I don’t have a personal website but LinkedIn is usually where I share information. It’s been a long road to write this book but the feedback has been amazing and if any of the listeners out there wanna learn more, I’m happy to talk. I’ve done lunch and learns with suppliers to share more about the book. I’ll be talking to different universities in the fall, especially in the Philly area to students that are gonna graduate soon. So it’s a perfect book for those people that are about to enter the workforce. It’s a book for people that maybe they’re stuck in their current job, they haven’t been promoted and they need an extra edge or it’s managers that are trying to get their team stronger. And there’s a lot of insights in the book that will make you a better employee, which in and then will make your company a stronger company.

Brett McKay: Fantastic. Randy Ornstein, thanks for your time. It’s been a pleasure.

Randy Ornstein: Oh, it’s been great, Brett, thank you so much.

Brett McKay: My guest today was Randy Ornstein, he’s the co-author of the book Grow: The Essential Guide to Getting Promoted. It’s available on Make sure to check out our show notes at, where you find links to resources, where you can delve deeper into this topic.

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