How to ask for what you want...(with examples!)

Early in my coaching process, I work with clients on their non-negotiables.
​What are the five things they need to make this next role feel meaningful, successful and on their terms?

Defining the kind of organizational culture they’re seeking (ie. collaborative, casual, no assholery) or the level of flexibility they need (ie. hybrid, remote, or simply to be treated like a grownup) often come up on the list.

It’s helpful to have this criteria in your back pocket as you’re evaluating opportunities. And – it’s critical that you vet out for these things in your networking and interviewing.

The question I often get is - How do I ask for these things without sounding like an entitled jerk?

After I stare down our Capitalist, Patriarchal, Hustle Culture with an invitation to fight this round, I take a deep breath.

I understand.

We have been taught to be grateful for what we get and not ask for more. Even when what we are given is not working or not enough.

The good news is that we can be clever and play the game without ever using the words want or need. That marketing background never disappoints.

Here are a couple of phrases you can use that are positive, confident – and also matter of fact.

"I thrive…"

I thrive in organizational cultures where there’s downtime between meetings to do the deep work that is so important in my role. Is that how you would describe the culture here?

Or

I thrive when I can give and receive feedback often so that I can continue to learn quickly in my role. Is that how you would describe your leadership style?

"I am my most…"

I am my most creative when I can brainstorm in a room of colleagues and it feels safe to pull all ideas (even the out there ones) on the table. Is that how you would describe the culture on the team?

Or

I am my most focused and thoughtful when I can work hard during the day and then log off completely to recharge after 6:30. Is that the kind of work day that’s understood and respected here?

I love all of these examples because they imply –

I’ve had this before so I know it’s possible.
If you don’t have it here, I will keep looking until I find it.


Now, just because you have these lines written out doesn’t mean it’s easy to say them. I would practice so you remember hearing them in your voice and perhaps write an abridged version of your questions on a cheat sheet if you have a virtual interview.

You know I love an update so let me know how it goes!

Rachel GarrettComment
Listening and shifting in 2025

This coming March marks the 10 year anniversary of my business. What??? 

It’s truly hard to believe that I’ve been nurturing, imagining–and at times strong-arming this business into what I want it to be for a full decade. 

I continue to learn something new each year. 

I continue to be in awe of  the clients I get to serve. 

And one of my unexpected joys of running the biz is my weekly note to you. Whether you were one of the 100 OG’s who signed up in year one  or a more recent friend, I appreciate you, hang on your every reply and want to do my best to deliver ideas that shift your day, your week–or your career even just a little. 

But–that’s not how I felt at the beginning. 

When a business coach told me that I MUST start a newsletter back  in 2015–for marketing purposes–I had my first new entrepreneur tantrum. You may remember I was leaving a career in marketing, so more marketing was not top of my priority list. 

But–I listened. 

I wrote. From my heart. In my way.

It became my place to put all the pieces together. 

To create art out of work. 

Now, ten years in, I want to keep listening and learning and helping you imagine work that fits with the life you want to be living. 

You are the expert of you and how you want to grow. 

So, what might that be? I’d love to know! Feel free to reply with some career  topics that have resonated in past newsletters or  are of interest to you for your 2025 career moves. 

And speaking of your 2025 career moves, I’m excited to share that I’ll be introducing a couple of new ways we can work together this year. 

It’s clear–some of you have been job searching for a bit already (2025 is your year!) and are seeking shorter packages where we can troubleshoot the areas that are not working in this tricky market. Message received. More information on this to come! 

Thank you for being part of my ten year celebratory listening tour. 

Rachel GarrettComment
Proactive Job Search Series: Part 4

How to know your proactive approach is working…

How to know your proactive approach is working…

In this final part of our series, we’re discussing…how you know when your proactive approach is working. 

Finding a job is a long (typically 3-6 month), multi-step process. 

If we only celebrated the win of – getting the actual job, we would NOT make it through the entire process intact. 

There are small milestones (that are actually big milestones) we can check off our lists and small wins (again, truly transformational wins) we must honor along this journey. Are you picking up what I’m putting down here? 

No incremental step forward in this proactive approach should be underestimated as small. These are seismic shifts that lead you to a different kind of career and life–one that is on your terms and designed by you. 

Here are 10 of the hundreds of shifts along the way that I celebrate with clients…

  1. When you invest the time to think about and write down the work you enjoy doing and what you’d like to learn. 

  2. When you’re clear on your superpowers and the unique value you can bring to an organization and your work. 

  3. When you can talk about your superpowers. Out loud. With another human. 

  4. When you do the research on  salaries of employees with similar skillsets and expertise and you decide you will ask for AT LEAST that amount. 

  5. When you write an elevator pitch that feels so very you and when you share it with people they say…”Damn…you really know who you are and what you want!” This actually happened with a client on call the other day! 

  6. When your network is sending you the right kinds of roles and making very relevant introductions for you. You’ve been so clear with them that they know how to help! 

  7. When you have your first interview in 5 years and it wasn’t perfect, but you got a few solid answers in and…you didn’t die. 

  8. When you don’t get the role you were interviewing for, but they say they want you to apply for other roles at the company. I promise, they DO NOT need to say that and WOULD NOT if they didn’t believe it. 

  9. When you feel like you’re meeting interesting and talented people in the process with whom you want to continue to be in touch. 

  10. When you feel momentum. You’re getting the right kinds of meetings. You’re confident in how you’re telling your story and your intuition tells you, you’re getting close. In my experience, clients often want to be cautiously optimistic at this moment, but their intuition is usually correct. If it’s not the role in front of you, it’s on its way. 


Now, of course–for most of my goal-oriented clients–the new job is the SUPER WIN. And they get there, sometimes in the 3 months we’re working together and sometimes after. 

Yet with all of these micro wins (that are really macro) along the way, they feel changed by the time they get to the actual J-O-B. They’ve claimed their power. They feel agency in their decision. They are ready to expand into this change with courage, as they are.

Rachel GarrettComment
Proactive Job Search Series: Part 3

When your network is tiny or non-existent…

Welcome to part 3 of our Proactive Job Search Series! If you’re someone who considers your network to be teeny tiny or if you’re asking the question–what the f*ck is a network–you’re not alone and there is still time to build one so that you can be proactive about your job search or building a career on your terms. 


You may not have a network if you:

  • Are a recent graduate and early on  in your career. 

  • Have worked for a single company for your entire career. 

  • Have worked for companies and institutions that are more focused on jobs and tasks rather  than relationships

  • Haven’t had time for conversations outside of work and family relationships.

  • Recently moved to a new town or city. 

Wherever you are is a fine place to start. Self judgment or a focus on what you “should have done” is not helpful for moving forward. 

We start with compassion. 

So take yourself off the gazillion  job postings and let’s focus the time you DO have on building out your professional network. 

If you have a small network, here’s where to  start?:

  1. Connect with your alumna networks from the schools you’ve attended. Do they have local in-person or virtual events you can go to? Are there other alumni in your field who you can connect with on LinkedIn or for a coffee?

  2. If you have kids in school, get to know the other working parents. What do they do? Where do they work? Do they enjoy 

  3. Find a networking group or meetup that relates to an interest or part of your identity. For example, I have clients that belong to local working mother groups or groups for marketing professionals or teachers. Also, some of my Queer clients belong to LGBTQ+ professional groups like Out Professionals or Lesbians Who Tech

  4. Find one or two people who are connectors (like me!). There may be someone in your life who LOVES to bring people together, make introductions and play professional matchmaker. Have a chat with this person and see who else they may be able to introduce you to (people in your industry, at companies that interest you, who’ve made similar transitions). These are what I call high impact conversations because you walk away with 5 or 6 new introductions. FYI–this is part of what I offer clients when they’re working with me. I like to introduce them to people within my network who are often very generous with their time (Thank you, network!).

Once you have spent some time expanding your network, then I would begin applying to roles that are connected to these people within your new and growing community.  #team[NAME]

In our last part of the Proactive Job Search Series, we’re going to discuss small wins and how to know when you’re making progress–before you actually land the new job. 

Rachel GarrettComment
Proactive Job Search Series: Part 2

What to do when your timeline is yesterday/immediate…

Quick recap - proactive job search is…

When you define your terms and priorities, then you network to find companies and roles that align with those terms. You  build relationships at those companies–so when they have the right role that’s a fit for you–they think of you and consider you above other candidates. At a more senior level, it often looks like organizations creating the right role for you (yes!). 

In Part 1, I focused on the steps to take when you think your search will be at least 6-12 months away. That seems like a lot of time, but there are absolutely actions you can be taking and people you can be connecting with so that your search feels more (dare I say) leisurely and actually like making new friends. 

This week–we’re switching gears to talk triage mode. 

How do you navigate a proactive job search when you’re in an active and immediate search. Like, you need to find this new gig yesterday and the days are rolling on. 


When time is of the essence, I recommend you: 

  1. Stay close to your core skill set. Look for roles that are  closely connected to what you have done in the past and use this pivoting opportunity to focus on companies that have a culture that’s better aligned with your values or a leader that ranges from neutral (read not an asshole) to inspiring. Ideally, there would be a few new areas to learn that will keep you hungry and engaged in the role. It’s wise to think about a path that is an exciting bigger shift in your longer term future. Yet, it’s ok to say, “not now” to that path if you’re prioritizing speed. 

  2. Turn the volume WAY UP  on networking.  The low key, casual approach we discussed for a search that’s 6-12 months out no longer applies. Create a list of your ten target companies and network your ass off to get to know people at those organizations. Meet with the connectors in your life who can set you up for additional conversations at your target companies or companies like them. Drop your search and your elevator pitch into conversation AS MUCH as possible. I mean, when you see people, you talk about it.  Don’t miss out on those opportunities to network where you are. 

  3. Only apply to roles when you have a contact. While it will feel tempting and productive to apply to roles online where you don’t have a contact, your time is better prioritized networking or finding a connection for roles where you feel like you have a solid chance at breaking through. I often say, applying for the role cold, without a contact is a path to despair. And I don’t want that for you. 

Of course this all works when you have a network you’ve been cultivating and nurturing throughout your career. But, what if you don’t? I’ve had a few clients come to me recently in this predicament and we need to approach the proactive search with a different spin. 

Stay tuned for when I cover what you do when you don’t have a network in Part 3!

Rachel GarrettComment
Proactive Job Search Series: Part 1

What to do when your search is 6-12 months away…

I talk a lot about a “proactive job search.” So, what does that even mean?

Here’s what it’s not…

Applying cold to job postings where you don’t have a contact.

Only focusing on opportunities that come to you via recruiters, colleagues and your well meaning family who collectively have no idea what you do.

Instead, a proactive job search is…

When you define your terms and priorities, then you network to find companies and roles that align with those terms. You build relationships at those companies–so when they have the right role that’s a fit for you–they think of you and consider you above other candidates. At a more senior level, it often looks like organizations creating the right role for you (yes!).

Sounds simple and yes it’s an approach that takes time. Yet–it delivers results and careers that are on your terms, in your words, designed by you. Think meaning, fulfillment, agency.

In this set of four emails, I will be addressing:

  1. What to do when your search is 6-12 months away

  2. How to proactively search when your timeline is immediate

  3. What to do when you have a tiny network

  4. What does progress look like?

Ideally, you want to get ahead and start connecting with people when the transition is just a sparkle of an idea that seems far off in the future. Frankly, it’s never too early to start connecting with your network–and you should be doing it even when you’re content in your role.

So, that’s where we’re starting in our series.

If your job search feels at least 6 months to a year out, here are some of the questions you can ask yourself…

  • What do I want to learn in my career? (hint: what feels energizing to learn rather than what feels like a “should’ or “have to.”)

  • Who do I know who does some of what I want to learn in their past or current roles?

  • What companies do I want to learn more about?

  • Who do I know at these companies that I can connect with?

  • Who do I know who can connect me to people at these companies?

  • Who are my mentors and advocates who want to help me?

Now, do a brain download of all of the people who come to mind. First on a piece of paper and then, if you’re anything like me, you’ll feel discomfort until you wrangle these contacts into a spreadsheet.

Start reaching out to the folks on the list with a target of setting up 1-2 meetings a month. Always have a goal for your conversation and think about who these people might be able to introduce you to.

At this point, you’re looking to continue to expand your network and get closer to the answer to question number one. What do I want to learn?

I highly recommend finding an accountability partner who has a similar timeline. Set up monthly conversations where you can discuss the meetings you’ve had, what’s currently scheduled for the coming month, what’s coming out of these chats and what dots you’re connecting about what could be next for you.

In Part 2, I’ll talk more about the scenario of when you find yourself in an active job search and you’re looking to switch from a reactive to a proactive approach…at lightning speed!

Happy connecting!

Rachel GarrettComment
How to Tame your Impostor Syndrome

Sometimes when I’m prepping a client for an interview, it’s clear – they’ve done their homework..

Elevator pitch ✅
STAR  stories ✅

How many tennis balls fit into a limousine? Kidding – we don’t prep for that one anymore. 

They know their stuff and yet, it’s not landing when we do a mock interview. Or they’re sweating through a 2nd shirt. 

That’s when we take a step back and look at what’s truly getting in the way. 

It sounds like…

Why would they want me when there are so many other candidates? 

I don’t have every bullet in the job description. 


Am I even [INSERT ANY COMPANY NAME} material?


In these moments, I say with all the love and compassion, what’s holding you back here is not your expertise or your level of talent (which is typically off the charts).

It’s the dreaded impostor syndrome. 

It’s that part of you that doesn’t believe you’re worthy of this role. 

The eight-year old part who didn’t get every answer right on the worksheet and was scolded by a parent, a teacher or a competitive kid. 

She’s scared. She's stomping her feet to stop you from taking a chance on doing anything that is not perfection. With the sweat and racing heart, she’s trying to redirect you to safety. 

But you – you know that these are the moments you pull yourself out of the game. When you don’t go for the promotion or the public speaking opportunity. 

And you promised yourself that you’re ready to break this pattern. To step forward, even when it’s messy. Especially when it’s messy. 

So you sit this 8 year old you down in that chair that everyone fights over in your childhood home. 

And you give her a hot cocoa with as many marshmallows as she wants and you say – Little me, we’re ok. 


Somebody should have told you, you can do your best and you can get some answers wrong and you will still be smart and lovable and worthy of getting that VP of Marketing role. OK, that last part may not make too much sense, but trust me it will some day. 

You can say all the things you needed to hear then and are still hungry for now. You can breathe through whatever feelings come up and know you will have to say these things again and again to make them stick. 

But it’s worth it. You’re worth it, sweaty pits, imperfect answers and all. 

Rachel GarrettComment
A Love Letter to My Network

I’m filled with gratitude, because my network is generous, open, responsive – and cool AF.

I’m a connector to my core so I get an adrenaline hit when I curate pairs of humans I know will appreciate each other and learn from even a simple half hour conversation.

And my network shows up!

Whether it’s former clients talking to new clients about how the process worked for them.

Or former colleagues at my clients’ target companies – talking about culture, leadership and the day to day of a role.

The number of connections I’m able to make a week is one of my favorite parts of the job.

So thank you for your time.

Thank you for paying it forward if you’ve been helped in your career transition.

Thank you for normalizing that it’s ok and even exciting to want something new.

I appreciate you and all that you are offering to my clients who have no idea how they will find the right connection to what’s next in their career.

I often find that right connection with you and in you.

And if you’re still looking to meet some new people in the Brooklyn area this month – I’m having what will most likely be my last Career Walk and Talk of 2024 and this time we’re doing a lunch edition.

We’ll be meeting…

Wednesday, November 20th at 12pm ET at Prospect Park, 3rd street entrance
(We’re keeping it to 60 minutes this time.)

Rachel GarrettComment