None of us will be shocked to hear, this goes way better for the men, 76% of them eventually get a promotion offered to them at some point in their career. But by and large, that still might be one promotion, could be many, but it could still only be one.

This is not really a viable strategy for building an entire career that will be full of many, many promotions, right? So, yikes, but the good news is amongst all this drama, that 68% of people who actually do ask for a promotion get one, so your chances that you ask are actually quite high.

Step #1: Actually Tell Your Boss You Want a Promotion

The first step is to actually tell your boss you want a promotion. Who could have seen this coming? What happens next? After you go and ask your boss for the promotion?

Well, you'd say, "Hey boss, I want a promotion." And they say, "Let's do it." Yay, amazing, confetti rains down from the ceiling, you're showered in not only confetti, but extra money because they give you a raise with it too, and life is grand, right?

Maybe.

The more likely scenario for most of us, because you wouldn't be here if that's how your conversation had gone, the more likely scenario is they go, "Uh, sorry, we don't have the budget right now."

Or maybe they go, "You know what, we've just finished a promotion cycle, why don't you try again a full year from now?" Or maybe they go, "Listen, I like you a lot, but the CTO is never going to say yes to this after the way we treated him last quarter, so I just don't see this going anywhere."

Or even worse, you go to your boss and say, "Hey boss, I want a promotion." They say, "Ha ha ha, you loser, you're barely doing your current job, there's no way I'm giving you a promotion." And then you crawl away in shame. So, terrifying, it's a lot of bad outcomes.

I spent all this time at the beginning hyping you up, telling you there was a 68% chance of success, and then I show you this, your boss laughing at you and telling you you're a failure? Holly, this is not very encouraging, is it?

So, what went wrong here? Why is it this festival of bad answers?

Stop: Step #1 is NOT Your First Step At All

Well, the reason why this is a festival of bad answers is because this actually is not step one at all.
Step one is not to tell your boss that you want a promotion, that's actually step five in the process.

This was a bit longer of a process than we expected, and there's a lot of work that we need to do upfront. So all of these examples I've just given you where the answer is, "Sorry, there's no budget," or "the CTO doesn't like you", or "you're out of cycle", or, "Hey, I don't think you're even performing in your current job," they fail because you didn't do two key things, which is to control the process and to anticipate the objections.

When you're getting answers like that, that means that either you didn't know what the process was going in, right? Things like, "Oh, we just missed the promotion cycle," or you didn't anticipate why they'd say no. CTO doesn't like you, your performance isn't quite there, there's no budget.

These two things are really crucial for you to get figured out before you even go and ask your boss for the promotion.

The Goal is to Trap Your Boss into Giving You a Promotion

Ultimately, the goal here of everything I'm going to teach you tonight is to trap your boss into being forced to give you a promotion.

We want that yes to be inevitable. I like to think of it sort of like playing a game of chess and getting the moves exactly right so there's no chance of them winning and every chance of you winning. But tonight, I'm going to teach you how to trap your boss into giving you a promotion and how to not fall into those pitfalls we talked about before.

There's a nine-step process. Now, I know some of you will be thinking, "Nine steps, Holly, I just want to make more money, I just want a better job," right? The nine steps will take some work. So, it's probably not going to be a promotion that's just handed to you.

But the good news is almost always they work, if not right away, eventually. And if you can't do the nine steps, you'll probably be really exhausted by doing the new job with the new responsibility. So get to work on the nine steps, friends.

NEW Step #1: Make Sure You’re Winning in Your Current Job

Step number one is actually to make sure that you're winning in your current job. This is to avoid the situation of your boss laughing in your face and saying, "There's no way because you're doing a bad job at what you're doing now."

This is something really, we could have called this step zero. We want you to do this well before you even get to the table. You want to make sure that when you're having your year-end review with your boss that you should be having everything come back as meets expectations or exceeds expectations.

You should make sure that your boss is consistently giving you good feedback, that you're really doing every part of your job, there's no part of it that's going undone. All of these things should be going well before you even consider asking for a promotion.

If you're not confident in this, do not pass go, do not collect $200, go and get this sorted out before you move on to the next steps.

Now, if you want some help doing this, we've got some amazing videos on the WIMDI YouTube channel that will help you sort that out about how to handle your performance reviews, there's a whole series of them. So go and take a look at those videos and those will help you.

We're also going to talk a little bit later today about some things that'll help you with this, but just make sure before you even approach the topic of a promotion, that you're already doing good at the job you already have.

We're 11% of the way there, one ninth of the way there, if we've done that, we're already doing good. What comes next?

Step #2: Research & Gossip – Holly’s Favourite Step (with Example & Script!)

Step number two is my favourite step, the research and gossip step. I want you to ask just so many questions, more questions than you ever thought were possible to really figure out the lay of the land, what's going on here? What is the process going to look like.

We talked earlier about your job being to manage the process and to make sure that you understand what the objections are. So that's what all these questions are about. That's what all this research and gossip is about.

I'll put some words in your mouth for you. Here are some examples of things you can ask at this stage.

Things like "What steps need to happen to make promotions happen at this company?" "Who needs to approve this particular promotion?" "What's the timeline for a promotion like this?" “What constraints are there?" So, things like budget, review cycles, stuff like that.

From there, you can say, okay, so, "Who was last promoted into this role?" And "How did it go for them? Was it easy or difficult?" What kind of process am I into?

Go get in contact with them directly and gossip with them about how they got it done. Just get them to give you the cheat sheet and the playbook. They've been there, done that.

You want to know, "What did they do to make their promotion happen?" And "How much experience your boss has doing promotions like this?"

So, you might have a boss who's gone through six or seven promotion cycles and gotten three or four people on their team promoted. You might have a boss that's brand new at this and who maybe even has never asked for a promotion for themselves.

Remember those stats from earlier? There's a lot of people who have never done this. And so, your boss might really be kind of going through it personally, trying to figure out how to do this for you when it's something they've always been afraid to ask.

Really start to understand how much experience do they have? And is this a process that they're going to be comfortable driving? Or is this a place where if you want to have it happen, you're going to have to jump in the driver's seat a little bit because they're just as new as you are.

Then I want you to look at "Where can you find an internal job description for this role?" Companies will sometimes have job descriptions literally written for every job that they use when they advertise for a role or just internal purposes.

And companies will also often have the sort of job laddering documents that are made for succession planning that will help you understand exactly what kind of skills you need to move into the next position up or the position that you're most interested in.

I want you to go looking for those on your internal company systems, talk to HR about it. You can kind of ask your boss about it, although I prefer you be a little more covert, at least at first, so you can kind of get this on the down low.

But see if you can find sort of any internal indicator of what they think is required around the job that you're looking for. Then I want you to do the exact same thing externally.

Part of the reason I want you to look both internally and externally is because the internal job description will tell you how they see the criteria. And then the external one, obviously, tells you how everyone else sees the criteria.

Sometimes we can leverage the external one to change the internal criteria. If the internal criteria is drastically different than what most companies are asking for or looking for, and that's in your favour, then you probably want to mention that and see if you can kind of negotiate around what the requirements look like.

The other good thing about the external job description is if you can't find an internal one at all, if one doesn't exist anywhere in the company, that's true for lots of companies that are a little bit younger, that just don't have strong processes, great, make your own.

Go assemble sort of three or four external job descriptions, combine them all together and go, okay, what's the common denominator? If I had to write one from scratch, what would be in it? I mean, involve ChatGPT if you want to, right?

But take a look at what that external job description is so you can craft kind of a to-do list for yourself almost if one doesn't exist internally. Then from there, and we're almost at the end of this festival of questions that we talked about, is to ask "What's the internal pay range for the role?"
So what's the pay band structure and how is this role levelled?

And therefore, what can you expect to be paid for it? And of course, we don't want to just start us down with the internal pay band is, we want to look at what kind of data you can find about external pay.

You might be able to find that in job postings, salary surveys, gossip from friends. If you knew somebody who had this job and left it two years ago, call them up, ask them what they made. Any piece of information you can find about the salary will be helpful.

You can use that to influence how you negotiate for your pay later on. And for all of you wondering whether you can leave that till later, there's a real reason why this pay question is as early in this process as it is.

That's because anytime throughout this process, somebody could ask you, what do you want to get paid for this? And I want you to have a strong answer. I want it to be the right answer, not an answer that's too low.

Make sure you go out and do some of that external benchmarking around what the pay looks like so that you've got an answer prepared before you get into the process. Again, the whole goal here is to give you the information you need to be able to control the process and to anticipate the objection.

If you kind of know what's required in terms of the job description, you know roughly what the pay is going to be, you know who needs to approve it, what the timeline usually looks like, what the steps are in the process, you'll be in a really good position to help guide your boss through that they need it.

Also just to know yourself how it's supposed to go so you can keep all the parts moving on time so that this promotion actually happens for you.

22% of the way there, friends, we're almost done. Not really, we've done, we've got three quarters of the way to go, but we're chugging along.

Step #3: Benchmark Your Performance (with Examples!)

Step number three is to benchmark your performance. But notice, we still haven't started talking to your boss yet. We're only on step three, right?

This step here is a step that you do on your own. And I want you to take one of those job descriptions that you found. Let's imagine you wanted to be a Director of Product Marketing.

Let's say that this director of product marketing, job description you found says, you need to have achieved consistent or consistent achievement of strategic goals and KPIs. You need to have done the successful execution of multiple product launches with positive market impact.

You need to have demonstrated the ability to lead and develop a high performing product marketing team. You need to have shown proactive involvement in cross-functional projects with measurable positive outcomes.

And finally, you want to see some recognition by peers and leadership for contributing to the overall success of the marketing function.

A real job description will be much longer, but we're going to go with this one for now as an example. What I want you to do once you've got this job description is to use a stoplight rating system.

Red, yellow, green, where red is things that you're not doing. Yellow is things that you're kind of doing. And green is things that you're definitely doing. You've really got them handled. You've done them lots. You can say yes to this requirement on the job description.

Then you're going to go to this job description and you're going to highlight, colour code in some way, each of these things. Let's imagine we do this and we go, okay, yeah, I'm consistently achieving these goals and KPIs. I've done a whole bunch of product launches and they've gone really well.

My team is performing great, so I don't see any problem there. I haven't really done a lot of cross-functional projects. I think I'll colour that red. It just really hasn't happened since I've been in this role.

I think my peers like me, but I don't know that that would be really clear to my boss. So, I'm going to mark this one as yellow. It might need to be shored up a bit.

Looking at this, we have a picture of, if this is how I stack up, how likely am I going to be to get a yes when I go and ask for this promotion, right?

Then I want you to ask yourself this step or this question, which is, “Which of these things on that list is essential to me being just ready to take on the job?"

Quite often, these job descriptions are like wish lists. They're everything and the kitchen sink that an employer would want for somebody who could do the job amazingly well.

Somebody who's been doing the job for 10 years with amazing experience, would be performing in the way they outlined in this document. And quite often for you to just be brand new to the role, you don't need to be performing at that level.

You need to be able to be performing at a level where you're not making mistakes and ruining lives and making everything complicated at work, but you don't have to have absolutely everything nailed down.

I want you to look at this list and go, okay, which of these things do I really need to be able to move into the role? And which of these things could I develop on the job?

Part of the reason I want you to ask this question is because it's really easy for all of us to go, it must be the whole list. And because of the way these are written, it usually isn't the whole list, but we have this internal bias about it.

Also, the world out there has an external bias that says women have to have, you know, 15 out of 10 items on the list. So, I really want you to think hard about this question, go, which ones do I really need?

Let's imagine we look back at our rating and we go, okay, you know, do I really need all of these, or can I develop some of these on the job?

And let's imagine we think, you know what, this cross-functional stuff, I think I can cross that out. That's something that if I developed it in the first six months of the role, I'd probably be okay.

If I didn't develop it exactly on time before that, it wouldn't hamper my ability to do the role. I've done it in the past and I'm sure I can do it again. So we cross that out.

Now looking at this, we've got almost everything green with this exception of this one yellow box that we'll need to shore up.

Decision Point – Are You Ready Now or Do You Need More Development?

33% of the way there, we've done our benchmark and we have an idea of where we stand against what we expect the criteria to be. So now we've got a decision point.

Are we ready now? And we can just say to our boss, "Hey, I'm ready for the promotion."

Or do we still need a little more development, a little more time, a little more experience so that we can make those boxes green?

If you're ready now, you get to go straight to step five and go and talk to your boss about it.

Step #4: Make a Green Light Plan (with Examples!)

If you still need a little more development, then we've got one more step to do, which is step four, just for us to make a green light plan.

A green light plan is a plan to take however your current benchmarking document looks like this one with a little bit of yellow and turn everything that's red or yellow into a green square.

What you're going to do is brainstorm all the actions that you need to take to turn that square from red or yellow or those squares from red or yellow into green squares. And then I want you to literally put those actions in your calendar, because this isn't something that's going to happen in theory.

You're going to do these before you talk to your boss because I want you to be able to go into that conversation with a document that is as green as something that's famously green, Kermit the Frog. Just really green, as green as you can possibly make it.

There might be some things that you'll need your boss's help to do. Maybe you need them to give you an introduction to a team or negotiate with executives to let you present at a certain meeting.

If you have things like that, that's fine. You can leave them until later, but everything that you can do on your own without your boss's help, put it in the calendar, get it done now.

Looking at your calendar, you might say, okay, I'm going to go and have this conversation with my boss about my promotion on the 27th. What am I going to do between now and then?

Well, on Tuesday, I'm going to go make an alliance with Susan. She's been trying to get a promotion. I'm trying to get a promotion. Let's she and I talk and go, "Hey, Susan, if you say really good things about me to my boss I'll go and say really good things about you to your boss. You tell me what skills you want me to play up and I'll tell you what skills I want you to play up and then we'll go and be each other's messengers."

So maybe I want to do that this week. And then next week, I'm going to go and have a conversation with the CTO. Remember the one earlier that we thought maybe might hate us and block our promotion? Let me go talk to him and see what's going on there.

What are his objections to me being promoted? How does he feel about me moving into that role to see what I need to shore up there because there might be some conversations needed.

He might need to know a little more about my experience. Maybe him and I have to work closely together, but I'm going to go and have that conversation and get that started.

Then on the 23rd, I'm going to get my bestie, Greg, who absolutely loves me. We've got a great working relationship to fly past my boss's office and sing my praises, tell him how great I am, tell him what an amazing influence I've had over the leadership of this company.

That way, when I show up to my boss's office on Friday, he'll have that conversation with Greg, fresh in his mind, and he'll go, “You know, it's funny, people really have been saying you're great, yeah, Greg was in here just a few days ago, absolutely raving about you”.

And you can go, “wow, what a coincidence. Isn't that nice?”

Almost halfway there. We've gone and done our benchmarking plan, we've made a green light plan to fill it, and we've gone and executed it as best we can without any help at all from our boss.

Step #5: Actually Tell Your Boss You Want a Promotion

Now, finally, that we've got our ducks in a row, we get to go and talk to our boss about wanting this promotion, because we kind of already know what the game of chess is going to look like, or at least we know as much as we can about what the game of chess is going to look like.

Here's a script for you that you can use. You can say, "Hey boss, I want to move into such and such role by blah, blah, blah timeline, and I'd like your help to do it."

That's it. A whole 'nother 11%, and we're more than halfway done now.

We've gone and told our boss that we want the promotion, amazing. What happens now?

You've said to your boss, "Hey, I want a promotion." And most likely they go, "well, okay, you're not quite there yet", right? You go, "All right, well, what skills do I need for the job then?"

Expect Vague Feedback from Your Boss

And they go, "Okay, well, improve your leadership skills a bit." And you're sitting there going like, what does that even mean, improve my leadership skills?

That's pretty vague. How am I supposed to do that? But of course, you take it in your stride and you try and do your best, right?

At the end of the day, bosses really love to give vague feedback. It's a challenge that quite a lot of bosses have. It won't surprise me if many of you in this room have a boss who really loves to give you vague feedback.

Part of the reason this happens a lot is one, because bosses are so busy, they don't really have time to sit there at night psychoanalysing and trying to figure out exactly what's going on.

A lot of them are just running as hard as they can and barely make time for that. The other one’s don't really know that it's supposed to be more specific than that. They haven't had good training.
As a result, they give vague feedback that's not that useful.

There's another category of bosses who give vague feedback because vague feedback has you exactly where they want you.

It gives you not very much information, doesn't let you anticipate objections and kind of lets them string you along for a long period of time because they've never really given you something that you can pin them down on. This is something that we're going to have to fix.

Let's imagine they go, "Okay, so you need to improve your leadership." And we go, "I guess I'll try." And six months later, we come back and go, "Great news, I've improved my leadership. I'm ready for my promotion, right boss? Right? Right?"

And your boss goes, "Well, not quite. There's one more thing I need you to do." By this point, you're flat on the floor dead, exhausted, because you've been working on this for six months, but your super vague boss, who's now come back and said, "You know what? You thought you'd be crossing the finish line, but actually I need a little more out of you."

This happens because bosses love to do the prove it again dance. Prove it again, is a dynamic that was illustrated in an amazing book I was talking earlier about a book that I love.

This is one of the other one of maybe two or three that I actually really, really love and think is useful. And it's called "What Works for Women at Work." And it's by Joan C. Williams and Rachel Dempsey.

The prove it again dynamic is where women have to consistently show again and again and again, that they not only are ready for the next challenge, but that they've actually already done it.

You have to show that you've done it one time, two times, three times, 10 times. You just have to keep showing it. There'll always be a slight tweak that they need. "Okay, yeah, you've done a pretty good campaign, but I want to see it with some email marketing", or "Oh, I want to see a little more collaboration with sales next time", or "Oh, I don't know if it was quite big enough", or "I want it to be international".

It will not be surprising if you come back, having done everything on the list, and your boss says, "Well, okay, one more thing." This is a little bit of a hazard that we're going to have to watch out for here when we go and ask our boss for a promotion, that they might come back with some prove it again nonsense.

This combo of really vague feedback and then prove it again later on is going to be pretty deadly to your ability to get a promotion. Between these two things, they can string you along forever and ever and ever.

The good news is I've got a couple of steps coming up that will help you make sure that you don't fall into these two traps, even though they are the absolute favourite traps of your boss. Remember, we're trapping the boss, not the boss is trapping us, right?

Step #6: Get Your Boss to Benchmark Your Performance (with Examples!)

Step number six is to get your boss now to benchmark your performance. We've already done one ourselves, but we're now going to get our boss to do it. There's two different ways that we can go about making this happen.

The first way is you can say to your boss, "Hey, I found our internal rubric for such and such role. Could you tell me how you'd rate me on each of these points?"

Then your boss is going to sit there and go, "Okay, well, how do I think this person's doing? Well, yeah, their goals and KPIs are on point. They're hitting those. Product launches, yeah, they've done one or two. I don't know if I'd call it multiple. I feel like I'd like to see a little more out of that before I really say that that's ready to go at the director level.

And in terms of leading and developing a high-performing team, the team performs well, but I want to see a little more out of her in terms of leadership before I'd say she's ready for the director level. And then cross-functional projects, no, none to speak of. They haven't done any of those in the last little while.

Recognition by peers and leadership for contributions to the success of the marketing function. Actually, yeah, there's a lot of that. I can't believe how many people have been in my office lately telling me how good she is. So that's going really well."

Of course, when that happens, you can sit there and smile to yourself and go, "I know because I trapped you. I sent Greg into your office to tell you how great I am."

You might, at the end of the day, be looking at a kind of rating that looks like this. And while I love that that last point was turned green by all of our benchmarking and green-light planning efforts, I do not love at all these two yellow boxes here because on our document, they were green.

On our boss', they are yellow. So what is going on with that? Why did these show up yellow on our boss' document and green on ours?

Part of the reason that these show up yellow is because of how we framed the question. I actually don't want you to do it the first way. The way I just told you to do it, cross that out.

We're not going to do it. We're going to come in with a slightly different approach that will end up with slightly different results from your boss.

Instead of saying, "Hey, can you rate me on each of these points?" You're going to say, "I found our internal rubric for this role, and I rated myself against it. Could you tell me if my ratings match your view?"

Then you're going to give your boss the one that you filled out. Now, why would I want you to do this? I want you to do this because of an effect in negotiation that we call anchoring.

In negotiation, this is the concept where if we're negotiating over the price of candy or a salary or something like that, whoever throws out the first number has the tendency of focusing the entire negotiation very close to that number. The initial offer really matters a lot because it's seen as the first initial reasonable place to start.

So, when you come in with your ratings that are all green, it's not magic. You know, if you just colour everything green even though you're not doing it, your boss isn't going to be brainwashed. Like, "I guess you are great."

But it gives you that slight edge in the moments where your boss is saying, "Uh, kind of, but maybe on my side, I'd kind of edge it over to yellow." You'll be able to flip some of those slight yellows to green just because they go, "Uh, I guess so, I guess so."

So here, what we might end up with is, you know, maybe that execution on multiple product launches, "Uh, you know, yeah, she has done several. Could it be more, I guess, but it's good enough, right? Good enough for me.

And, you know, the high-performing team thing, I still want to see better leadership on that. That one is, I'm not going to move. I disagree with her. I'm going to colour that one yellow. But everything else would basically agree on."

A little trick in how you frame it that can have your boss come over to your side on some of those a little more dicey calls, right?

I want you to use the same magic words we used before on your boss. Which of these things is essential to me being ready to just take on the job, not performing it like I've been doing it for 15 years?

I know lots of these job descriptions can be written like wishlists, and I want to make sure I do all of them. Well, what are the things that I need to be able to do to be ready to just start, to be just in the beginning?

From there, you might be able to make the argument with your boss that this thing that we talked about earlier, the proactive involvement in cross-functional projects is something you can take on in the job as opposed to ahead of time.

You might not convince them, you might, but it's worth a shot. Now, feel free, by the way, to take a page out of my book from earlier. You can ask this question really open, right?

"Which of these things is essential?" Or you can say, "You know, I've been thinking a lot about what I think is most essential for me being ready to take on this job. And I think that these cross-functional projects are something that I could do within the first six months, and that I probably don't need to do before I get into it because I have so much experience doing it before, and it feels a little bit like a box we need to check, but not something that is essential from a skill perspective before I'm ready."

So, you can, rather than just asking it as an open question, provide a point of view, and then test how your boss feels about it. That's another way of kind of putting your hands on the scale like we talked about earlier.

So, you're going to try to sell your boss on this idea that you don't really need to do those cross-functional things, and let's say, all right, you're successful. Now we're almost 2/3 of the way done.

Step #7: Get Useful & Detailed Feedback from Your Boss (with Examples & Script!)

The next step is to go get feedback on anything that is still outstanding. Any yellows or reds that are on your document, you're going to need to understand, okay, why does my boss think that that's yellow or red?

Because it's not just about what you think, what matters a lot is what they think and how you convince them to turn it green. Remember, we don't want the vague feedback that our boss is going to give us by default, most of us.

We want feedback that is detailed and actually useful. Useful feedback has three main elements. It needs to cover what the behaviour is and what it should be. It needs to cover what the impact is of whatever behaviour it is we're talking about. And it needs to cover the importance of that thing.

For any managers out here who want to get better feedback to your team, this is a helpful rubric to use to make sure that every time you give feedback, it contains information about all these three things.

If you're somebody who's trying to get good feedback out of your manager, what you're looking for is things across these three areas to help you really understand what it is they're looking for.

You're going to ask questions to help them be more specific in these three areas. And I'll give you words that to put in your mouth that you can steal directly from me.

In terms of behaviour, some questions that you could ask your boss are, "What specific actions do you observe me doing around such a skill that work and what doesn't work?" You could also say, "Hey, do you have any examples of whatever behaviour they're trying to describe?"

You could say, "If I was doing this at a 10 out of 10, what would it look like?" And you could say, "What behaviours or actions would you like to see out of me to be sure that this was addressed?"

Notice that some of these questions are questions around how it's going now, AKA kind of like what's not working or what makes us a yellow or a red.

Then some of these questions are around what good would look like. Make sure when you're talking about behaviour that you get information about both, and make sure you get information that is very specific.

Something like “improve your leadership” is not nearly specific enough. Asking for specific actions or examples or behaviours, those are some key words that you can pepper into your questions that will help them narrow in on it.

Now let's take a look at impact, the second thing on the list. You could ask, okay, what would happen if I was successful? "What effect would that have on the business or on our department" or on whatever it is you're trying to find?

And you could say, "What reaction would this behaviour that you're trying to get me to do elicit from the team or from senior management or from our stakeholders", whoever it is that you're trying to impress?

You could also say, "What do you think the impact of this behaviour is on my chances of moving into that role I want, that promotion I want by next year or by whatever your timeline is?" You could say, "Hey, what are the consequences if this doesn't change right now?" Not saying I'm not going to change it, but what would happen if it didn't get any better or any different than it is now?

All of these questions here help you nail down kind of the 'so what' of the behaviour. Is this behaviour that annoys your boss? Is this a behaviour that's going to cost you guys $30 million? Is this a behaviour that's going to endanger a key relationship?

Is this a behaviour that isn't harmful where you are, but is absolutely essential to you being able to function as a VP, and therefore it's crucial for you to develop it at this point in your career if you want to keep moving, like what's going on here? What's this about?

The third piece is around the importance. Questions you can ask here are, "How significant of an impact is that", right? AKA, hey boss, how important is this? Just a slightly less judgmental way of saying, "how important is this, really?"

You can also say, "Do you consider this a big priority for my development right now?" You could say, "Is this do or die?" Or you could say, "Hey, what makes this a priority over this other thing that we've talked about?"

Notice that some of these questions are about kind of quantifying the impact. Some of them are about deciding how big of a deal it is within the grander scheme of things of our own development.

There's a really black and white question, is this do or die? Or there's questions where you get them to sort of relativistically rate it in terms of priority with other things.

All of these questions are useful for informational purposes, but they can also be really useful if your boss is saying, "This is the most important thing ever", right? And you say, "Well, what makes this seemingly small thing from my point of view, what makes this a priority over this much larger thing that I think I should be focusing on?"

That's a good way of kind of getting your boss to calm down and refocus on what really matters without making it seem like you're arguing with them.

You could just say, "Hey, tell me about your prioritisation. Why this and not this?" And then they'll be forced to think it through. So, this is actually a strategy as well. All of these are strategies for helping your boss thoroughly explain the feedback, but also get it down to the right size so that they understand how much this should get in your way or not in their own words.

We're 78% of the way there. We've made our own ratings. Then we've gone and told our boss that we want a promotion. Then we've got our boss to rate us. Then we've gotten them to drill down into hopefully very useful, not at all vague detail about the places where we still have gaps.

Step #8: Make a Green Light Plan with Your Boss

And now we've got a few more steps. So just like we did for ourselves, we're going to make a green light plan with our boss because whatever we think the plan should be doesn't really matter. What matters is what we agree on with our boss.

A big part of what we're doing here and the process of going to get this promotion is we're building agreements. We're saying, I see it this way, you see it this way. How do we make that the same?

And then how do we agree on what an appropriate course of action is going forward? Because if you can agree on that now, that's one fight you don't have to have later on. And one objection you don't have to handle when it comes time for your conversation about your promotion.

From here, we're going to make a green light plan with our boss, which is, hey, here's how we're going to turn all these yellow and red squares into green squares. So just like before, you're going to brainstorm all the actions you need to take to turn it green.
These actions are actions both for you and for your boss. Probably you are not the only one coming out of this conversation with homework. There will be things that you need from your boss around this.

There will be conversations you need them to have. There will be specific mentoring requests that you'll have. You might need training or specific projects to give you the experience at doing things.

Your boss should probably not walk away from this conversation with no to-do list. You both should have things that you're going to do coming out of this conversation. Brainstorm everything that you need to be well-resourced and able to turn these yellow squares or red squares into green squares.

Then, just like before, literally put them on not only your calendar, but your boss' calendar. This might seem bold, but I actually really want you to help reinforce your boss getting this done and putting it in their calendar.

It's very easy for this stuff to slip off the calendar amongst the chaos and firefighting of running a day-to-day business. So, I want you to be pretty insistent with your boss and say, "Hey, when can we get this done? When's this going on the calendar?"

Setting the Boss Trap 😈

Then I want you to use my special closer. This is my favourite part of the process. This is the part where we really trap your boss. This is the peak trapping moment, trapping your boss into giving you a promotion.

The words you're going to say are, "So if I do these projects and behaviours that we've agreed on right now in our green light plan, then will you be willing to promote me to the role that I want by such and such timeline?"

This is a magic sentence. It does so many good things for you. Here are the things that it does. First of all, it's an acid test. Have I got all the feedback? And is it the right feedback?

Because if your boss says no, then you know there's something here you haven't uncovered. There's an objection that's coming that's outside of your performance. There's something that was left off the list.

The behaviours that you talked about are good, but they're maybe not the quite right ones or they're not detailed enough. Basically you're saying, "Okay, is this the whole list? If I do this, are you a yes?"

We're testing to find out if that's actually a no. That's one of the main functions of this. Because if it's a no, that's great. That just means we've got a little more homework to do.

We have to go, "Okay, great. What else would you need to see? What else would this need to be to be a yes? How else do we need to adjust this for these boxes to all be green and be ready to say yes to my promotion?"

So that's number one. And the other thing that I love about this magic little sentence is that it creates an agreement between you and your boss.

So that if you go and do these things and you come back six months later or however long the timeline you'd set is, and you say, "Hey boss, I've done it." It is just that much harder for them to say, "Sorry, tough beans, we're not doing it." Because they already said they would.

Why are they going to say no now? They are left with two choices. Either there's got to be a really good reason, or they were lying in the beginning. And most people don't love to sort of come up against that reality. "Sorry, I lied to you. Tough." right?

This is a helpful little bit of pressure, this agreement that will help them move towards yes as opposed to towards no. Magic sentence, love it. Special closer. Please, please use it. It's very, very helpful.

What Happens Now?

We're almost there, friends. 89% of the way. We're almost done. I can almost taste the promotion. We've set our plan. We're going to work on our plan. We got on our boss' calendar. Our boss said, "Yeah, if you do all those things, I'm in." So now what happens?

Obviously, we're going to do the green light plan. And then we say, "Hey boss, I did everything we talked about. I want the promotion now." And then your boss is going to go, "Amazing, let's do it."

And so then you wait, right? Time goes by, seasons pass, maybe you get a new haircut. Eventually you start to wonder, is this promotion even going to happen?

Do you say, "Hey boss, what's up with my promotion?" And your boss says, "Yeah, I'm still working on it." And you're like, "Hon, it's been three years. How much work does it take? I did everything we talked about. How could it possibly take this long?"

I've been here, I've seen many of my clients here. When you're sitting there, you've got wrinkles older than this conversation. How can it possibly take so long?

The organisational inertia will absolutely ruin your life. Like I mentioned earlier, there's everything on your boss's to-do list that is more urgent than this, that is easier to do than this. If you don't keep the pressure on, other things will pop up that inevitably are squeakier-wheeled than you.

It's really essential that you are not allowing this to slip off into the good night, never to be seen again.

Step #9: Make It Happen (with Examples & Script!)

Step number nine is for you to go and make it happen. And that step, I also like to call relentless follow-up. Your boss should be a little tired of you talking about this. We're not going to talk to your boss about it every five minutes, but we are going to talk to your boss more than your boss expected.

There's two key tools that I want you to use in this process. Number one, always have your next meeting set. You should never leave a meeting with your boss without a plan and a next meeting to check in.

You might say, "Okay, boss, we need to go and execute some cross-functional projects. I am going to go and talk to Steve in product.

You are going to go talk to his boss and make sure that we can get this project off the ground. And you and I are going to meet here next week. You're going to tell me how your conversation with your boss.

I'm going to tell you how that conversation went with Steve. And then we'll make a plan from there. Sound good? How's 1 pm?"

Always, always have your next meeting set so that you don't accidentally let three, four weeks, six months go by without ever bringing it up. Always have a due date and just set your next meeting.

This is an old sales tactic and it's an old sales tactic because it works. Keep your next meeting on the calendar.

Here's a little script for it, which I've already said. "I'm going to do this, you're going to do this. When should we next meet to discuss this?" Or, "How's Tuesday at four?" Feel free to just insert a time.

The second thing I want you to do is to be a relentless force for yes. Your job is to be the person that facilitates yes and makes it happen, makes it the default outcome, the easier choice.

The wonderful Darrell Farrow, who is in the room tonight here as I do the talk, often talks about the difference between "can I?" and "how can I?"

A lot of us come to these types of conversations, or even our entire career in general, by going, "Well, can I get a promotion? Can I go and do that project with Steve?" "How can I do this?"

And this is really the question that we should be asking rather than, "can I do this?" When we come at it from the place of "can I?", there's really only two options: yes or no.

We put all the control out there. We let other people decide what the rules are. When we start asking "how can I?", we become more able to produce possibility.

We become more able to produce ways to make a yes. It's not, "Okay, well, will my boss say yes to a promotion?" It's "How can I convince my boss to say yes to a promotion?"

Maybe then all I need to do is do this extra project, demonstrate this extra skill, go get another job offer so they think that I'm at risk of leaving and have the conversation with them and then I'll do it.

So "how can I?" is a really important perspective for you to stay in any time you're having the conversation with your boss because they won't always go there by default.

Remember for them, the easier thing is to be lazy and never have to go and promote you. Because they don't lose anybody on their team.

They don't have to train anybody else. They don't have to have endless conversations with HR and all the other people that they need to convince to say yes to this.

This is the no work option to have you not get promoted. So, you're going to have to constantly be advocating for the yes and looking for ways to make it happen.

A couple of key questions that you can steal from me are,

"How can I get experience doing such and such type of project in the next three months?" "The next time I do such and such skill, could you attend the meeting and give me feedback afterwards?"

"Who would you recommend I work with to help me achieve whatever thing we're talking about that will help me with my promotion?" Or "How else could we do this thing?"

Notice that that question at the end is a great question to deploy when it seems like there's no other answers, right? None of the answers we thought of works, must be a dead end.

Your job then is to sit there and think, okay, how else could we do this? What other ideas can we brainstorm? There must be a way around this.

People get promoted all the time. How do they do it? How do they get this type of experience? How do they overcome this roadblock? What else can we think of?

Your job is always to be the, "what else can we think of" person with your boss? Do all these things and do them enough and you will eventually reach 100%.

Now, let me be clear, friends. You might go through this whole process and the last phase in particular, the phase where you do the green light plan, and we communicate with that with your boss and then move the ball forward towards you getting your yes, this phase is probably the longest phase of most promotions.

And you may get this done in one promotion cycle or you may get this done over two promotion cycles. It's not entirely uncommon. Go for it once, get most of the way there, but don't quite get it and have it spill over into a second. That's no problem.

But if you keep at it, if you are persistent at coming back and having these conversations, re-benchmarking, remaking a plan, going out and doing the planning, saying, is this good? Now, what do we need to do? How else do we do this?

If you keep having those conversations with your boss, eventually the promotion will come. And if the promotion doesn't come, despite you doing all this, call me up, we need to find you a new job, because there's something wrong.

If you're doing all of this and you still can't make it happen, then either there's something about it that's not quite working, or there's something about your job that's not quite working. If you're doing these steps, you're really doing everything you need to do to move your life forward.

So promotions aren't done in a single conversation. As I was saying, this will take probably a lot of conversations with your boss and that doesn't mean the process is broken. Doesn't mean you're doing anything wrong. It doesn't mean there's anything wrong with you.

This is normal. And the more senior you get, the more true this will be. As you get more and more senior and especially if you're working in certain types of companies, you getting promoted might not just be about kind of ticking pre-defined boxes.

It might be about creating a brand new role for yourself that hasn't existed before. And that process is the same one we discussed here in a lot of ways, but a lot of people need to be involved. A lot of people need to get comfortable with the idea. There's a lot of details to work out.

So, this will always be more than one conversation unless your boss says yes instantly or no instantly and then that stops you. You're always going to have many conversations and that's totally normal and amazing.

Summarising the 9 Step Process

Here are the steps for all of you who want to have them all in one place.

Step one, make sure you're winning in your current role so your boss doesn't laugh in your face. It's very embarrassing. I hope it doesn't happen to you. Then research and gossip.

Find out everything you can about the process, about the requirements, about who's involved, about what the pay structures look like, about people who have done it before, about people who've done it before at other companies and how they did it.

Ask more people than you think is reasonable, questions about this because as you're going through your promotion conversation, it's really just a negotiation, right? You'll eventually be negotiating pay.

Right now, you're negotiating title and stuff like that. But information when it comes to negotiation is always your advantage, always helpful because it helps you do those two things that we talked about.

Control the process and anticipate what the objections are so that you can make sure the process moves forward and so you can make sure the objections don't get in the way. The research and gossip phase is crucial and you'll do it here up front but you'll also be doing it the entire way across.

Then benchmark your performance so you can get a sense of how you stack up versus what you think the requirements are.

Make a plan for yourself to stack up better than you do now and go and execute on that, get as much of it done as you possibly can.

And then when you're at your shiny best and you already think you know almost everything that's coming, go tell your boss that you want a promotion. Finally let the cat out of the bag and put the pressure on your boss. Amazing.

Then we're going to follow almost the exact same steps but now with your boss. We're going to get them to benchmark your performance so we can understand how they see your skills, then we're going to get feedback around any places where there's gaps and we're going to make with them a plan to turn everything into green highlighted sections on this job description.

We're going to go do that plan and then we're going to make it happen with our boss. We're going to follow up, we're going to set meetings, we're going to always ask the question, "how can I?, "how can we?", "what would it look like if?, "what if we did it this way?"

We are going to be relentlessly cheery, relentlessly there, always with a meeting on the calendar and eventually we'll get our promotion.

All right, the Promoti-O-Meter has gone all the way from 0% all the way up to 100, hooray! We've done it friends; we've achieved our promotion.

Finally, after many, many months of effort, we are here, and we can have a little celebration.