The Hidden Mid-Career Answers: How to Impress Your Boss

The topic of today’s article is, I think something we can all relate to, which is how to impress your boss? What do I do to impress my manager? 

Imagine this Scene at Work

So let's set the scene here…

It's Monday, you're at work, sitting at your desk… 

For weeks, you have been working on this huge project; you know it inside and out. 

You've interfaced with leadership, and you've coordinated across departments to turn in the various milestones. You delivered your part of the project well, and you've gotten great feedback so far. It's feeling like another feather in your cap. You're confident in your expertise in this area of the project, and also you've got some notes. You've got a couple of great ideas about how to make the project work even better, and then…you get an email. 

You open it, and you find out there was a meeting about the project, about how to address the course of action, and how to get better results. And here you are staring at solutions that you were either about to pitch or that at least you could have contributed to. 

And oh, when that happens, it stings. 

Reality: it's probably not the only time that there's been a meeting, or an opportunity–a project, that could have really raised your visibility–and where you could have contributed a lot. If people had just known or thought about you. 

You should have been in that meeting. And then you wonder…

Did they forget about you? Does your manager not respect you? 

And more importantly:

  • How do you get into that meeting next time? 

  • How do you stick in the minds of your manager or your leadership, 

  • How to rise to that level so that it's a no-brainer for them next time. 



Moving beyond early-career ways to impress leadership

So in my work as a guide to over 600 mid-career women working at massive corporations (like Amazon, Wells Fargo, Nike) smaller boutique design firms, G firms, and media companies, across tons of different industries, I noticed that often really ambitious women over-indexed on certain hard skills, like managing P&L, or presenting skills they're sure they need to get that promotion. 

But in so doing, they are ignoring three key skills that matter just as much to your advancement, no matter what your industry. 

After years of working with women, and seeing that these skills just were remaining ignored or just undervalued…I took all the successes that I had in getting women hired, promoted, upgrading their leadership mindset, and I designed the Career Strategy GPS program. It's a six-month hybrid online course and group coaching program, where I guide women toward a strategic next role that sets them up for their long-term trajectory. Along with these three impactful skills that I will reveal in this conversation, that would help them break through to their managers and senior leaderships, and create that new role, and the compensation that fits their expertise, and grows their impact. 

And even when they get the job, these skills will keep raising their profile and really make them that much more effective in getting things done – which is the point of being in this new role, right?



The Before Times: What we used to do to impress leaders

But before we get to those skills, I want to talk about what we used to do – The BEFORE times. 

In our early career, it's a different time – we're spending a lot of energy just figuring out what we want to do, what industry we want to be in, and what role in that industry. 

And once we settle on something, we're just figuring out how to do that thing competently.

Over a couple of years, we even get good at some stuff. We start realizing where our skills are, where our passions lie, and what works for us at that moment. 

However, we're thinking about it also as an individual contributor. Just–what is going on with me, my career?

So that often means when it comes to our relationship with leadership, it looks like taking direction, implementing what someone else says, and then delivering. We get rewarded for that for a very long time. 

It makes it incredibly easy to simply continue that pattern.



Mid-Career Now

But the thing I want to impress on you is that mid-career, now, includes a different set of rules… 

In this phase, it's more about honing and deepening your expertise, that value proposition, and maybe even living your mission or purpose. It’s definitely knowing your value and getting compensated for all this impact that you've had. Realize, you know so much, and it's time to be rewarded for that. 

And it means a new skill set is starting to develop: growing in your leadership. That means upgrading your communication, having greater confidence in your achievements, and having a presence that backs up that confidence

The Biggest Mindset Shift

The biggest mindset shift is moving away from that “individual contributor” mindset into a “leadership mindset.”

So–moving from me (I just need the skills that I need to do the job to deliver) into we. 

From Me to We.

The we, being the organization, starting to take their considerations into your calculations. 

That means honing higher-order interpersonal skills. 

The 3 impactful skills you need to impress your boss

Unlike the skills we concentrate on–the ones we need to do the tactical part of our job–there is another set of skills that go ignored. These skills are true across every industry.

  • vision

  • influence

  • storytelling

Vision setting is the first of these three skills. Basically, being able to paint a happy ending, or amazing end result of what your project or what your department should be.

And then storytelling, being able to speak convincingly about that vision, giving the right examples, the right stories, to be able to bring people along. 

Thirdly, influence. This is knowing which stories to tell, in the right way to bring people along. 

Learning to practice and perfecting these skills–those are the ways to impress your manager and other senior leaders when it comes to promoting you, even if you're in an external job search. 


Skill number 1: Vision Setting

Let's get into these three skills that I'm talking about, beginning with vision. 

I talk a lot about taking control of your career by learning vision-setting and starting just with what you want. 

Being a visionary is for everyone. It's a skill that can be cultivated. 

In fact, in the first module of the Career Strategy GPS program, you can get perfect clarity, a 360-degree view of where you want to be in the next 5-10 years, and then what role you need to get, to get there. 

So you get massive clarity once you're starting to orient yourself in your organization, or a job search. 

But you also get a framework that you can use over and over and over again, throughout your career or for your organization. 

This is something that you can use to impress your boss. 

Because while having a vision for your career is very important just to establish that you know where you're going…having a vision for your organization, for your department, for your team, for whatever you're trying to change, is incredibly powerful in terms of sticking in the mind of your bosses. 

Let's go back to the scenario… 

You've been working on that project, you've got clarity on what could be better, take it a step further…

What if, before starting that project, you had an idea of what the department needed, and you would paint a picture of it for your manager? 

I'm going to give you an example of something that a client of mine came up with recently… 

Really, it's just about having an opinion about where things should go. For her, at a mid-stage startup, she recognized that her organization, her particular team, wasn't running as efficiently as it could. And it was bringing them behind in their organization. 

Her vision was about having repeated processes that are documented, and templates that are stored in this library, to make work go much more efficiently so the team could be a leader in making the org ambitious deadlines. She was tying it to something that the organization wanted–meeting and exceeding deadlines. 

And then she also realized that her team was very junior. The budgets that they had only allowed for people with less experience. So her vision was implementing monthly Learning Labs, which would have become a mentorship scheme where senior designers would train juniors to get them up to par, so that you were bringing these new mostly junior team members online and working at a senior capacity so that, again, they could be fulfilling those deadlines for the organization. 

If that is something that you're known for, having that vision, that big idea, then it begins to prove that no matter whether they agree with you or not, you're taking initiative to think about what would work better for the organization. 

That is truly a clear indicator that you are a team player. You're thinking about the good of the organization. 

And not only that, but you're trying to improve the organization's results in meaningful ways. 

Think about that from your manager's point of view… 

These people are beleaguered, they have all these demands from their bosses. 

Now you're not just another employee, you're not just somebody they can give information to. You'll implement it and deliver it, which is great. 

You're now turning more into a partner–somebody who is sharing in their struggles and doing what they can to make bigger changes that will increase the efficiency or revenu, whatever the organization is looking for. 

Somebody who sees the big picture, thinks ahead, and thinks strategically. 

If they don't go for your idea, that's okay. There's no denying you've got moxie. And that confidence that you have, it's contagious. You're going stand out in their mind–and that can lead to becoming someone who, over time, gets invited to more meetings. 

But that alone isn't going to do it. Because maybe you have this vision for your role for your department, you've got all these great ideas, and they've got tons of potential, but you're still wondering, “Okay, but why is my idea not landing well with leadership?” 



Skill number 2: Storytelling

Here's where storytelling and influence, the other two skills I mentioned, are key to making an impression. 

We've talked about having a vision. And that can be hard to get people to care about if you can't communicate it well.

Developing storytelling as a skill is the ability to get people to remember you and your ideas by tying them to a larger narrative. 

So why is this work? Why is this so important? 

Maybe if you're here, you know my background as a television writer. So of course, I care a ton about storytelling. It's one of the most fundamental human experiences. 

Humans tell stories all the time, from answering the question, “how was your day” to actually writing the great American novel. 

And the thing is, humans also remember things much better when you put them in the context of a story. 

So I'm going to tell you a story right now…

Why storytelling helps your case

There is a Princeton professor, Dr. Yuri Hassan, whose team ran an experiment. They had listeners find out about a bunch of facts. 

They delivered a bunch of facts to listeners. And then just orally, they just said, here are the facts, A, B, C, D. 

Later they asked the participants, “Okay, what do you remember?”

They only remembered a fraction of the details. 

So then they delivered the same facts in a story.

Today, I woke up, and then this happened, and that happened. 

And when they put the same facts into a story, then the listeners actually retained the information. 

And something else that is truly amazing happened… 

The listeners, when they were listening to the story, their brainwaves started to sync up with that of the storyteller. 

So what that means is: stories literally get people on your wavelength.

Isn't that incredible? That's so powerful. 

So the way to impress your manager or your boss is to choose the right stories that will get you on the same wavelength. 

This is also known as influencing or positioning. And there's an entire module in Career Strategy GPS on how to approach your one-on-ones to position yourself for promotion, and how to use each interaction to communicate effectively so that by review time, your vision and value are so clear. They've saturated your manager's mind, and every other senior leader that you need to advocate for your promotion. 

And in the meantime, you're also still top of mind, and perhaps brought into these meetings that you're hoping to get into.

Skill number 3: Influence

Swaying other people's opinions is influence. 

This is a skill that you're going to need as you move up because the bigger the impact, the bigger the decision affecting more people, which means more decision-makers. There's more buy-in, and you have to convince more people. 

Influencing is something that you're going to need in any industry. From big tech to big lion taming. You gotta get the senior lion tamers to agree with your vision of sticking a head into a lion's jaw. And that starts by telling the right stories. 

So going back to the example we had, you worked on that project, and you've got these great ideas about all the things you could see improved. (Maybe even the things that would match up to your own vision for how projects get done by your team, your own vision for the organization, for how the team can work more effectively.) 

So you can go in guns blazing and talk about everything you think could and should be changed for your benefit (like, how it's going to make your life easier, how it's going to just work for you as a person, as an individual contributor). Or you could go in and pitch that same story, and match that to the organization's goals. 

Take it out of your perspective and say, “Hey, the thing that I'm pitching right now, it's not just for this project; this actually gets us closer to Q3, Q4, whatever goals.”

Again, this makes makes you more of a partner to the person you're trying to impress, your boss.

Having them think, “Hey, I'm having a meeting, and we're coming up with strategy. You know who's great at that?” – You. And inviting you. 

How to be seen as the leader you know you are

I have a way more down-and-dirty teaching about being seen as the leader that you know you are by the leaders you hope to become. 

It's invite-only, and it's only accessible to folks who apply and are accepted to the Career Strategy GPS program. 

This is for folks who want to get results: 

  • to change how they're seen

  • upgrade their leadership skills

  • accelerate that promotion

  • cut through job search 

And it starts with three short questions. These are questions you have to ask yourself no matter what, anyway, if you're looking to figure out your career goals. If accepted, it gets you access to the training, and I cover more on storytelling, vision, and influence there. 

And throughout the program, there is mentorship from seasoned coaches, and a community back in the hallway. 

If applying to the program isn’t on your agenda at the moment, I encourage you to join our newsletter. We cover topics like this, weekly, so when you’re ready to make your move you’ve gained some of these skills we talked about today!




Alex Cooley