Hi Realists! 👋

Welcome to Cup of Ambition, Volume 10!

In this edition, you’ll get the scoop on:

‼️‼️ 9-to-5 Dilemma: PIP Nightmares.

📌 4 Interview Questions That Impress.

📚 Book Spotlight: Likeable Badass (Q1 Book Club!)

😫 Beyond Frustrated at Work? Ask Yourself These 2 Questions.

9-to-5 Dilemma.

“I’m embarrassed to even say this, but for the first time in my life, I’ve been put on a performance plan at work. I thought I was doing the right things, but what my boss wants is constantly changing and we have no resources to support what they ask for. One week I’ll be chasing a new campaign and the next week I’m told that the campaign is paused because of budget, but I’m dinged because I didn’t get the campaign out.

It feels like I can’t win. I’m so humiliated that I’m a 44 year old adult being chastised at work. When my boss gave me the performance improvement plan they asked, “have you ever been on a PIP?” When I responded “no” they said “well, now you have.” They went into a bunch of stories about my performance not being where they expect it to be, but offered no resources or support.

I feel sick. I’ve heard that it’s unlikely for people to successfully overcome a PIP. Am I doomed?”

-Performanced Out + Mortified.

_____________________________________________________

Dear Performanced Out + Mortified,

Repeat after me:

“My performance plan is more likely to be a reflection of poor internal communication and bad leadership than it is about my own abilities.”

Performance improvement plans (PIPs) can feel like a punch to the gut, especially when it feels like you’re doing everything you can in an environment that keeps shifting its expectations. But being on a PIP does not define your career, nor does it mean you’re doomed. What you’re experiencing is tough, but it’s a challenge that many professionals have faced, and many have overcome.

Let’s break this down.

1. You’re Not Alone—This Isn’t About You Being “Less Than”

Performance plans aren’t always fair, and they often aren’t a reflection of your abilities or work ethic. It sounds like you’re navigating a chaotic situation where expectations are constantly changing, and that’s exhausting. When your boss is inconsistent with priorities, it’s no wonder that it feels impossible to win. But remember: this speaks more to the system around you than it does to your competence.

2. Focus on What You Can Control

While your boss hasn’t given you clear resources or support, here’s what you can do:

• Document Everything: Start keeping a detailed record of the goals set for you, the shifting priorities, and the lack of support. This will help you manage conversations with your boss and could be helpful if you need to escalate the situation.

• Clarify Expectations: Don’t be afraid to advocate for yourself by asking for specifics. If the goals keep changing, request written clarification on what the priorities are week to week. This ensures there’s a mutual understanding and helps reduce the chance of being unfairly “dinged” again.

• Plan Your Next Steps: While you work through this PIP, start quietly preparing for other career options. Brush up your resume, update your LinkedIn, and lean into your network. You deserve an environment where your efforts are supported, not undermined.

3. Change Your Narrative—You’re Not “Doomed”

There’s a pervasive myth that being on a PIP means you’re on your way out. That’s not always true, but even if it’s the case, this can be the wake-up call to start advocating for yourself and your career more fiercely. Many professionals go on to thrive after leaving environments that didn’t serve them. Start thinking about what you want in your next role, and how you can use this experience as a catalyst for change.

4. Don’t Be Afraid to Ask for Help

It’s okay to feel upset or embarrassed, but don’t isolate yourself. Reach out to a trusted mentor or coach who can help you navigate this challenge. If you don’t feel supported at work, find support elsewhere. Your career isn’t over, and having an outside perspective will remind you that you still have the power to advocate for what’s next.

Being placed on a PIP can feel devastating, but it’s also a chance to reflect, regroup, and reclaim your career on your terms. Take this as an opportunity to push for clarity, advocate for yourself, and if needed, plan for your next chapter. You are not defined by this PIP, and there’s a path forward—one that’s focused on your goals, not someone else’s shifting expectations.

Stay strong.

4 Interview Questions That Impress.

We all know that part of any job interview is the Q&A. But far too often, people either skip it or ask generic questions that don’t really move the needle. I can’t tell you the number of times candidates went silent when I asked if they had any questions. The truth is, the questions you ask can be just as important as the ones you answer. This is your chance to advocate for yourself, demonstrate that you’re thoughtful about the role, and show that you’re thinking long-term. Here are four questions that will help you get deeper insight into the job, the company culture, and your potential future there:

1. "Looking ahead a year from now, what would this hire need to have accomplished to exceed your expectations?"

This question shows that you’re already thinking about what success looks like, and it signals that you’re results-driven. You want to be clear on what winning looks like in this role so you can plan accordingly. More importantly, it sets the stage for you to advocate for the support, resources, and clarity you’ll need to reach those goals.

You’re asking for specifics here—get clear on the metrics or milestones that matter most. It’ll give you a roadmap for how you can make an immediate impact.

2. “What barriers or challenges exist in this role?"

Understanding common challenges can give you insight of what you’re about to face. Often, you’ll find interviewers will share key information about outdated systems, inefficient processes, and lack of resources.is open can give you insight into the team’s dynamics and the company’s growth (or challenges).

You want to make sure you’re stepping into an environment where you can thrive—not one where you’ll be set up to struggle.

3. "Can you share a time when someone at this company was encouraged to step outside their role?"

This question helps you gauge whether the company fosters a culture of growth, flexibility, and initiative—or if people are expected to stay in their lane. Asking for an example will give you real insight into how the company approaches leadership development, empowerment, and creativity. Are they truly invested in your growth, or will you be stuck in a rigid box?

Use this question to determine how much the company values professional development. A strong culture will encourage you to stretch, grow, and contribute beyond your job description—without overstepping into burnout territory.

4. "How does this team handle feedback and performance reviews?"

Feedback and growth go hand in hand. You want to know how the company approaches performance development—do they invest in helping their people succeed, or do they focus solely on results without support? This is especially important if you value ongoing learning and self-advocacy. You should be looking for a culture where feedback is constructive and leads to actual development, not just criticism.

This question sets the stage for you to advocate for ongoing support in the role. It also gives you a sense of whether the company prioritizes your long-term growth or simply expects you to meet immediate metrics.

Bonus Tip: Choose Wisely

Most interviews only leave a few minutes at the end for your questions, so be strategic. Pick 2 or 3 of these that will give you the most insight into the company, its culture, and whether this role aligns with your career goals. Remember, asking smart questions isn't just about impressing the interviewer—it’s about making sure this job will work for you.

Book Spotlight: Likeable Badass.

In her new book, Likeable Badass, behavioral scientist Alison Fragale dives deep into the delicate balance women must navigate in the workplace—being both competent and likable. With a combination of rigorous research, practical strategies, and real-life stories, Fragale teaches us how to build our professional status without sacrificing our warmth or authenticity. This book offers actionable advice on self-promotion, navigating office politics, and driving career success by reshaping how others perceive us. It’s not just a guide for women—Likeable Badass is for anyone looking to advance their career with both grace and power.

How It Aligns with My Practice

Fragale’s work resonates with my core focus on self-advocacy and grit. Many of my clients struggle with finding their voice, presenting their achievements confidently, and navigating tricky workplace dynamics. Likeable Badass provides evidence-based strategies for exactly this. It’s about owning your story and crafting a personal brand that reflects both your strengths and aspirations—principles I work with clients to cultivate daily.

Bottomline: self-promotion isn’t a negative thing!

Interested in a Q1 Book Club?

Would you like to dive into this book with me? I’m thinking of hosting a book club in Q1 to explore Likeable Badass together and discuss how its lessons can transform our careers. If you’re interested, let me know, and we can build something amazing in the new year!

Dollyism.

Don’t Be a Stranger!

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