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A
Welcome to Career Tools.
B
This is Sarah and I'm Mark.
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Today's podcast, how to Be an Effective Number two, Part two of two.
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As always, our content has been crafted by humans and we are now certified by the Proudly Human Corporation. The questions this cast answers are what does it mean to be my boss's number two? What do number twos do? And how can I be good at being number two?
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If you want answers to these questions and more, keep listening. Every episode of Career Tools is packed with guidance that could change the trajectory of your career, but only if you apply it. Career Tools licensees receive the full show notes for every new episode delivered straight to their inbox, making it easier to stay on top of the content, hold on to the insights that matter most, and take action before the moment passes. If if you're serious about your career, this is exactly the kind of advantage that adds up over time. Visit us at manager-tools.com memberships to find more about everything a license gets you. So it's not just about obviously running meetings, which we've talked about. You may also attend meetings for your boss and folks. Way too many managers complain about their packed schedules and then also attend every single meeting they're invited to. How many meetings have you been in where every single person invited was in that meeting? Yeah, like so few as to be
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almost people are making decisions about the priorities of the various things.
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Yeah, yeah. You don't have to be in every single meeting if you're invited to the meeting.
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Yeah, there are reasons to miss meetings, legitimate ones. But. But your boss won't have to miss meetings if she trusts you enough to attend some of them in her stead. Simple.
A
It's absolutely simple. And if your boss asks you to attend a meeting for her, ask questions about how she wants you to behave, find out what the topics will be in advance, get the agenda, and which topics are important enough to weigh in on. Be careful about going off the reservation because you personally feel strongly about something, and this will depend on the nature of your relationship with your boss. It's best when you're first asked to do this as a number two, to say nothing or do nothing without advanced expressed permission from your boss. And you know, Mark, when we talk about this, what what comes to my mind is do we have a podcast for learn who your friend, your manager's friends and enemies.
B
Oh yeah, know your boss's friends and enemies.
A
Yeah, yeah. It's things like that. Like you, you want to know what are their feelings on all the subjects, what are they thinking about them, what is, what kind of side are they coming in on on all of those topics. And again, whether or not your boss wants that shared or communicated, or you should just stay silent, all of these things are important. And if you don't know, just be quiet. That's the best stance.
B
Yeah. And look at a minimum, the basis here is you are serving in your manager's dead and you want to be able to brief him or her about what happened. And even if something happened that he might have been able to prohibit or prevent, that's okay. At worst case, you're going to take exceptionally good notes and brief your boss afterwards. And this is still quite a good role for you and saves your boss the time she needs for whatever the different priority is that conflicts with it. If something seems urgent in the meeting, text or call her immediately afterwards and let her know what's coming or what's up or what's different or what changed.
A
So another thing that you are very likely, if you're a number two to, to take care of in a way is handling reporting. And folks, effective managers don't create the reports they owe to the organization. Yes, of course they're responsible for the reports they owe the organization.
B
Some of the people listening don't understand what you just said. You said effective managers don't create the reports they owe the organization. What we're saying, folks, is the vast majority of managers do create the reports that they are the organization because managers have many managers, particularly junior managers, less experienced managers have not separated responsibility from action. The whole point in the transition is to learn the distinction between being responsible for something and doing it yourself. And managers think that everything reporting has to be kind of secret or whatever. But effective managers have learned the lesson that they don't need to actually create the reports. Yes, they're responsible for the action outputs in the reports, for whatever it says about the organization, about your, your boss's team, then that certainly is a reflection on your boss. But they don't actually have to create the report in Excel or PowerPoint or whatever.
A
And I mean, Mark, I. When you, when you start saying that, I think to myself about delegation and the need for it, folks. Also, simultaneously, if you are a manager and you are creating your own reports and you're thinking to yourself, but I need to create these reports because my folks can't do them well, then your role is to have them create the reports and hold them accountable for creating them well, not just doing them yourself. So all that to say if you are the number two, your Boss may ask you to start handling or taking care of the reporting again that they are responsible for, but certainly not going to run themselves. Who hopefully, yeah.
B
Now look, just to be clear, reporting is something that bosses pay special attention to because they haven't yet done the mental arithmetic to realize creating the report and the actual data and the report are two different things. But it's probably going to irritate your boss a little in the beginning. If he asks you as his number two to take on reporting, he's going to have to train you on how the reports are created. So step lightly about doing all of his reporting. Okay? If. If you're asked to pick up some of the reporting, that's a very good sign. You should be pleased and you should jump at the opportunity. Absolutely, boss. But you're not jumping an opportunity like, oh, this is going to get reformoted. What you should say is, when your boss says he'd like you to handle some reporting, what I would say is, whatever you need, boss. You know, whatever you need, I'm here to help you. You're not sucking up, you're just saying, I recognize there's a lot of work going around, and if I can help you, I will. Some of the reporting may be confidential in some way, although that is actually pretty rare. Usually we're not talking about salaries or compensation changes, anything like that. Don't confuse your boss wanting to hold on to one or two reports with a lack of trust. It may simply be that those reports are more radioactive than others, and he has in some ways, mistakenly used the creation of the report as an opportunity to learn about what's in the report so he can be prepared to defend himself. If there are numbers in there that aren't that good, perhaps those reporting the delegation of reporting to you will come with time. When you prove you can create those reports, he does delegate to you, and you do it accurately and on time.
A
And folks, whatever you do, don't miss reporting deadlines. If you're creating a report for your boss, you've got to hit the deadlines again. This is why some bosses don't delegate reporting. It's a mistake. But folks, the reason managers don't delegate items to their directs is because they feel they've been burned in the past by directs taking things on like reporting and then missing important deadlines. So if you think a report paints your boss's team in a bad light, ask your boss about how they want to handle it. It's not as easy as just creating the report, folks. You've Got to read it. Make sure that this is.
B
Understand it.
A
Yeah, understand it exactly. Make sure that you're not just throwing it out there. Because my job is to create this report and I just put it out there and I don't absorb the information at all and I just get egg all over everybody's faces. You want to talk to your boss. If there's something in there that you think might need them, they may need to know it, might need a liaising in some way. Your boss may want you to create the report and then send it to them so that they can send it on with some special note to their boss or, or whomever the target audience is. So it's more than just create the report and just like throw it out there into the world. There's more than that at this level of the organization.
B
Now another point about that you, you mentioned about meeting deadlines. So I'm going to give you a perfect example of how you're first, but still among equals. If you have two responsibilities due at a certain time and you can only get one of them done, you always get the things that your boss wanted done in your number two role done before you get your job that would be yours whether you were number two or not. So let's say you're a logistics person and you're the number two. You owe some information to a logistics coordinator at noon. And you also have to meet a deadline of getting your boss's report on X, Y or Z to the boss by noon. What you do, you take the number two responsibilities more seriously. You meet that deadline so that your boss doesn't look bad because that report is going to be seen at higher levels and you take the heat for the thing that you missed. And you don't tell your boss or anybody else, let alone your peers, well, I missed my deadline because I was doing your stuff. Because a delegation means it's now your stuff. But there's greater risk associated with missing a deadline or, or any other quality standard or any other standard at all on a number two duty rather than your standard duties. Now, you may not like that. That may expose you to a little bit of political back and forth. Yeah. And it's actually kind of good that you do because sooner or later, if you get promoted a couple of times, your life is going to be entirely political back and forth.
A
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B
Okay, next you're going to run major projects. We've already alluded to this, but too many managers think that they and they alone are responsible for all planning. Managers actually say to us, planning is in my job description. You know, I'm supposed to plan stuff. But again, that's a misreading of his or her job description. Your job description describes not what a manager must do, but what she is responsible for seeing done.
A
Yeah. And folks, if your boss delegates a major project plan to you, accept it. Just accept it. One of the unwritten rules of being a number two is that you're no longer one of the people in the team who gets to pick and choose what they want to work on. Being a number two means you no longer have that same ability to push back. Not that I would argue anyone on the team really has, but nonetheless, you're the number two. So you take it. That's what you do.
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Yeah. Even if you're not an experienced planner, you can learn with help from your boss. It's not hard once you embrace the iterative approach, knowing that your original plan will A, be changed because it should be only seen as a draft, and B, no plan survives first contact with the enemy, the actual work that has to be done. As the saying goes, planning is everything, but plans are nothing. Probably if your boss delegates planning some major project to you, he or she just wants a first draft so he can get a rough idea. And if he doesn't like it, he'll say, okay, these two things are wrong. I want you to switch around. I want you to do this and this. But. But he doesn't have to do it. He doesn't have to spend the two hours on a Tuesday coming up with a rough idea of the plan.
A
Yeah, we were literally on a call earlier today. Mark and Maggie said something to the effect of she was using Claude, in this case, to create a project plan for her. And she said it got me 60% of the way there. And I'd rather adjust something that takes me an hour to adjust than spend three hours creating. And it's the exact same idea. Your boss would rather spend an hour adjusting something you've created than four hours creating something from complete scratch.
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And you shouldn't try to do this without AI.
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Yeah, exactly. Plug for Claude. You start there. Your project plan will definitely be better than 50% by the time it gets to your boss, it'll be much better than that. Much better. And folks, don't burden yourself with stupid idea that your plan must be perfect right away. All planning is iterative. Ask your boss for some general guidance. And when you have their general guidance, get busy. Just start doing it. Turn around a first draft quickly. The reason your boss has asked you to do the first draft is because they don't want themselves to get in the weeds. Don't make them get in the weeds to feed you crumbs until you got what you need. Exactly. Get it out of your boss. Whatever you need to get yourself started. Ask for some general guidance. Don't be afraid of having to do several drafts to get it right. That's normal. Especially if you're not a planner by trade in this case. And if your boss has asked you to do something you don't have a lot of experience with, they don't expect you to get it right the first time or even the tenth time. This is going back to the AI analogy. They expect to get back something that they need to read and make sure it is correct and accurate. It's not like they're expecting production quality stuff, especially on something you've never done before. Even if you've done it 10 times, they're not expecting it to be perfect. And just turn it around immediately.
B
Yeah. So stop worrying about asking your boss to review it multiple times. In fact, you don't even ask him or her to review it. You just submit it and they're going to review it. You don't have to ask for a favor because they know ultimately it's their work product that it's going to affect. You're saving her the time of having to sit down and draft something. Being number two is a learning proposition. That's what the position is there for to help you learn, to give you the skills so that there is continuity among the team when the boss is out. The way you learn as an adult is you do things and you learn by your mistakes how to get better at them. Just trust yourself.
A
Yeah.
B
Okay. And if you're a high C, if you're a perfectionist, this is going to be very hard for you.
A
Yeah, it is.
B
Yes. And that's why we pay people to come to work, because sometimes things are going to be very hard.
A
Yeah, folks, I gotta tell you, and I hear this a lot, Mark, at our effective communicator conferences, this hesitation for more reserved people to take what amounts to not as clear as high Cs want it. Guidance and putting it into practice with very little information. But again, folks, part of the reason managers become hesitant to delegate things is because of this dynamic. Because if I was going to explain it to you in grave detail, dude, I would have done it myself. And in this case specifically, you have been granted the ability to be number two. What that means is there is implicit trust that exists. It just does. If your manager trusts you to that degree, trust yourself to that degree at least. And above all else, when it comes to being delegated a major project, don't get your feelings hurt when your boss points out flaws and mistakes. It's how we learn. Remember, it takes your boss less time to correct your work than it does to do it from scratch themself. And it's so much better to learn now when you still have air cover from your boss, than having to learn how to do it all after you get promoted to be manager. And that's the thing of it, right? Think of number two like being a manager, but with training wheels. You've got another person there to take the brunt of it. Like you have got another individual there providing you air cover for all of those mistakes. Being your second set of eyes, getting all of the things that you need to do done. But to that higher level. Don't see it as a, as. As critical to yourself as a person. It's not. But you're not going to be perfect at everything the first time you do it. No one is embrace reality.
B
Yeah. And the biggest step in the world is from 0 to 1. 1 to 2 is only a doubling. 2 to 3 is only 50% more. 3 to 4 is only 25% more. 0 to 1, you put 1 over 0 as a fraction and it's infinity. What you want to do is get your boss from 0 to 1 so he or she can look at it and then get it more easily to 2 and 3 and 4. Next on the list, you're going to present for your boss as well. Typically, again, not all these are perfect. And we're not saying every single boss uses exactly this way. But after 35 years of watching managers manage, we've seen what bosses who have number twos ask them to do. Your boss doesn't have to give all the presentations they're asked for. Your boss may ask you to step in when her calendar is intractable. It happens.
A
Absolutely. What your boss might do first is you have you create presentations which they will deliver. That's kind of the first step for some. They might work with you on the drafts. It's probably Best not to put them in PowerPoint or Keynote just yet. First, start by creating an outline. Just to make sure that you've got kind of the rough idea of what you want, like your story arc before. You spend a ton of time in PowerPoint. Because far too many presentations are started in PowerPoint and all of the time is spent on colors and logo and spacing and heading and subheadings, footers and fonts and all of the things that are so time consuming and so detail oriented. I mean, I don't know, Mark, how many times have you helped me with PowerPoint animations? Yeah, I mean, the things that you could waste your time on trying to figure out. And if, if you're boss and you aren't in alignment at the outline stage, you want to do that before you spend three hours trying to figure out animations. And folks, we've said it before, it's not about the presentation, it's about you. Your presentations are just a supporting document for you, the presenter. Which again, only solidifies or adds to the fact that if this isn't about the PowerPoint presentation, don't start at finished, start at the first step, which is an outline.
B
Right? Now, look, once you've prepared some of your boss's presentations, he will probably have you attend some of their briefings, okay? They want you to learn how others outside and above your team or his team, respond and ask questions and fight back against issues they disagree with. Your boss is trying to help you learn which issues you will not give ground on, and those you potentially could. They should also help you learn which people you will not be able to give ground to, and those you will your boss's friends and your boss's enemies. And after those two steps, at that point, your boss will likely delegate a complete presentation, draft, approval, rehearsal, and then finally the presenting itself. And this might take six to nine months. And if you show any lack of eagerness, the boss will say, fine, it's okay, I'll do it. And when the boss has to say about his number two or her number two, that's fine, I'll do it. You're going to start getting less and less to do, and you may still think you're the number two, but your boss probably won't treat you that way because you probably aren't.
A
Yeah, that's exactly it. And then ultimately, folks, one of the other things that we think you may be asked to do is act while your manager is out. So when your boss is out or unavailable, the general rule is that you, in this Case, the number two speaks for your manager. And yes, there are some things that are gonna stay with your boss even while they're out, especially at the beginning of your being a number two. But as you develop, as you've got practice in these different areas, the list of things that your boss has to do while they are out is gonna generally get whittled down because you'll be able to take on more and more of it as you've got some of that experience.
B
Yeah. When an effective boss is out sick, they will probably in many cases, but not always, ask you to run things. They'll ask you to make decisions and keep track of what you do and what you decide. And you're definitely going to have to brief your boss when she comes back. So keep a log of stuff that happens that you felt like you did relative to standing in for her.
A
And folks, when your boss is traveling, she's gonna let you and the rest of the team know that you, the number two, are in charge for most, if not all things.
B
Yeah, but please folks, hear us now. Do not get a big head about this stuff. The acting manager thing is what people get a big head about. It always reminds me of Dwight telling Michael Scott on the office, I'm the assistant regional manager. And Michael Scott always says, no, you're the assistant to the regional manager. Right? It's like, like Dwight always wanted more power. He's very power hungry guy. Stay humble. Don't get upset when one of your peers doesn't like your guidance and tells you in a huff they're going to wait for the boss to return. Let it go, okay? Your boss will correct them later or give you guidance on how to handle that situation. Don't try to pull rank because you don't have any. You have trust, but you can burn that trust down really quickly if you start acting like a martinet or a little junior boss. And oh no, you can't make that decision without me. You know, the, the manager's gone, so now I'm the boss. Don't do that. Don't move into your boss's office. If you're in an office. Holy Toledo, don't do that.
A
Yeah. And folks, if you want to endear yourself to your boss when they're on vacation, help them be on vacation.
B
Yes.
A
I mean, before they leave, which you'll know certainly when your boss is going to be out. Talk to them about which meetings that you should attend for them. Send them a meeting debrief after the meeting itself. If you get asked why you're there and your boss isn't here. Tell them, oh, my boss is on vacation and she asked for me to attend this meeting for her. And if someone tries to make you feel small and folks, they might just say, well, you don't speak for her. Don't argue. Don't push back. Just say, I'm sorry, I don't speak for her. Take notes. Contribute when you can. Do all you can to help your boss have a good vacation.
B
Yeah. Because, folks, if you think bosses, when you get promoted, one of the reasons you don't want to be a manager is, Is because it seems like when managers are on vacation, they dial into all kinds of calls. That's an ineffective manager. That's one that doesn't have a number two. That's one who doesn't know how to get all their stuff done and then assigns, delegate some responsibilities, people on the team and go, truly on vacation. Your company does not intend you to dial in. Now, if you're saying, oh, no, Mark, our culture is, if you're on vacation, it doesn't matter if you know you have to dial in. I'm not talking about crises. There are crises that happen where every manager has dial in one whether they're on vacation or not. But in terms of normal, routine operations, your company expects you to be gone. If your company doesn't and you think that's crazy, you might want to think about finding a different company. Okay. And by the way, managers want to have it both ways. They want to dial into the meeting to show everybody that they're, yeah, I'm on vacation. Sorry. If you can hear the seagulls in the background, Right. And they want the credit for being all in, all the time, 24 7. I'm on top of it. No problem. And then they want to whine to their family about how difficult it is that they make him go to all these meetings. If you really believe in family first, and we do, when you're on vacation, you should be on vacation. If you're number two, your role is to make it possible for your manager to truly be on vacation. Will it go perfectly? No. But whatever does nothing. So speed, meaning you being there rather than finding out much later about what happens. Speed is important, and so are vacations.
A
And, folks, it's not outside the realm of possibility that your boss is going to come back from vacation and mention that a couple of things could have gone better. Yeah, fair enough. Absolutely. I'm sure that that's true.
B
Yeah.
A
Learn from that. Get better, improve. Don't be defensive about it. Imagine, on the contrary, your boss giving you the feedback when you stand in for me while I'm on vacation. My family and I appreciate your hard work. There's no better praise they can come from a manager than you being here helped me go on vacation.
B
Yeah, I. I wrote that line. Of course. And when I heard you say it, I got choked up again. Just like I wrote when I wrote it the first time. Yeah, I appreciate your hard work. We can think of no higher praise. All right, can I summarize?
A
Yeah, do it.
B
Good. Okay, folks, being a number two is a great career enhancer. Not every boss is smart enough to have one. But if you are asked, we encourage you to take advantage of it with a learning attitude. Far better to learn about your boss's job before you have it. Many new bosses have failed because their boss didn't teach them about how to be a manager through delegation. And number two, before they got to be a manager, it was the boss's mistake. But it will be the new unprepared manager who will be punished. That is what is known as a moral hazard, which is unacceptable for those of us who consider ourselves true professionals.
A
Thanks, Mark.
B
Yeah, that was fun.
A
Thanks, folks. We hope this helped you. Now, help us help others. And tell your friends. And of course, follow rate and review our podcast. And remember, five stars only, please.
B
Five stars only, please. Sam.
Hosts: Sarah (A) & Mark (B)
Date: April 16, 2026
This episode is the second part of a deep dive into what it truly means—and takes—to be an effective "number two" (a manager's right-hand person) in an organization. Sarah and Mark break down the key responsibilities, pitfalls, and mindset shifts essential to excelling in this pivotal supporting role. The cast is packed with practical advice, best practices, and candid real-world examples to guide listeners who want to unlock the potential and career opportunity that comes with being trusted as a "number two."
Timestamps: 00:28 – 03:06
Timestamps: 03:46 – 08:41
Timestamps: 08:41 – 10:42
Timestamps: 10:42 – 14:24
Timestamps: 14:24 – 17:07
Timestamps: 17:07 – 20:33
Timestamps: 20:33 – 25:27
Timestamps: 25:27 – 26:14
"Far better to learn about your boss's job before you have it... Many new bosses have failed because their boss didn't teach them about how to be a manager through delegation and number two before they got to be a manager." (B, 26:15)
This episode is recommended for anyone aspiring to step into managerial roles, support senior leaders, or simply advance their career through demonstrated reliability and trustworthiness.