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How To Have A Difficult Work Conversation In 4 Easy Steps

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When you raise your voice, you raise your value.


Hi FairyGodMentor, 

How do you have difficult conversations with a supervisor who has not found their “why” and promotes a toxic culture? 

Yours Truly, Scared Silent

——

Dear Scared Silent,

First, I want to acknowledge and celebrate your courage for reaching out, showing your ASK, and requesting support while working in a toxic work culture.  It’s not easy and it’s evident that you desire to improve the quality of your work/life and others that may be negatively impacted.

To quote Mahatma Gandhi, “Be the change you wish to see in the world.” We have to power to make the positive change we’d like to see in the workplace by practicing self-advocacy.  Self-advocacy means speaking up for your needs, communicating your goals, and making boundaries. It also fuels career and leadership growth.

Having difficult conversations with a supervisor, especially one who is not aligned with their purpose or “why” can be very intimidating and even scary. I’ve created some survival tips to help guide you and others on RISE to higher heights using this type of assertive communication:

  1. Reflect: Gain clarity on your needs and limits. Understand what your limits are. Ask yourself: What do you need to do and feel your best at work?
  2. Identify: Discover a time that works best to talk to your supervisor. I know that you’d rather avoid having this tough conversation, but nothing is going to change until you speak up. You are a priority! Make your needs an agenda item for your next one-on-one conversation or set up a separate time to discuss.
  3. Strategize: Craft your conversation. It’s best to have a script prepared so that you can stay on topic, especially if emotions are running high.  Create a specific script of your talking points that you want to cover. Be clear and concise. I worked with an executive who liked things “right and tight.” Keep that in mind when communicating with people-leaders. No fluff. Stick to facts. If you’re asking for a behavior or workload change, focus on the why (impact to you, your team, and business) behind the what (the ask/the feedback/etc.). Focus on the impact and not the person. How is this behavior or action impacting you, the team, and the organization? Don’t forget to frame the conversation with empathy. You’ll want to open the conversation setting the intention of collaboration and support. You’re having this discussion out of concern for the success of your professional relationship (if you have one), the team, and the overall success of the organization. Use “I” statements to fully express how you’re feeling so you’re not putting the receiver of the feedback on the defensive. It may sound like “I think we can both agree that we have a shared desire to make sure the team and the business are successful. And you want us to be productive, right? I’d like to share some insights on some recent behaviors I’ve witnessed and their impact on me and the team. Then, I’d like to discuss some solutions on how we can create more harmony in the workplace together.”
  4. Execute: This is where the rubber meets the road. Prepare, speak, listen, and then clarify. Before you have this discussion, you’ll want to prepare to overcome any challenges you may face. Anticipate the questions that may be asked for clarity. Feedback is a gift. People may take it, use it, or throw it away.  Based on what you shared about this leader, prepare yourself for some resistance and deflection (throwing things back onto you) that may take place.

You’ll want to practice for this type of conversation. Make sure to role-play with a trusted colleague or mentor. Stick to your script. Once you’ve said what you need to share with your supervisor, pause and listen for a response. Remember, this conversation intends to come from a place of collaboration and support. As a leader, (remember you don’t have to be a people manager to be a leader), you’ll want to focus on solutions, not the problems at hand. You’ll want to actively listen to what your supervisor has to say and then work together to come up with a solution that will work best for both of you. Real talk, the solution may mean working with a different leader or finding a new place to work, if that’s an option. 

If you’ve tried to have this type of difficult conversation and the toxicity persists in the workplace, I would highly suggest you bubble this matter up to Human Resources. Ask to have them present to mediate future conversations, especially if you’ve tried to resolve this on your own.  

Keep your receipts and take notes. Send a copy of what was discussed to your supervisor and Human Resources. This protects you and the organization.

I say this all of the time, Scared Silent: when you raise your voice, you raise your value. You have value and it’s important to voice your concerns and be heard. By reflecting on your needs and limits, identifying the right time to discuss, strategizing your conversation talking points, and executing your discussion by being fully prepared to overcome challenges, you’re on your way to fostering meaningful change in the workplace. Be the change!

You got this!

With love and light,

Your FairyGodMentor®

Joyel Crawford is an award-winning career and leadership development professional and the founder of Crawford Leadership Strategies, a consultancy that develops empowered, results-driven leaders through engaging leadership development coaching, training, and facilitation. She is the author of the best-selling book and audiobook Show Your Ask: Using Your Voice to Advocate for Yourself and Your Career.

Have a question about handling a micromanager, are you having difficulty navigating spaces because of your hair, is work stressing you out, do you need support coaching poor performance, or are you wondering how to negotiate and get the job offer you desire effectively? Do you have any questions about career and leadership development? 

Ask Your FairyGodMentor® here.


Gen Z Workers Are Revolutionizing The Workplace

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Gen Z workers are changing the workplace as we know it through the use of more virtual workplace tools like Slack instead of lengthy emails.


Gen Z workers are revolutionizing the culture around work, especially regarding communication, Fast Company reports. They have swapped lengthy emails for short-form messaging, adding an emoji or two along the way. 

In a 2020 consulting firm Creative Strategies survey, Gmail ranked fourth on Gen Z’s list of collaboration tools, trailing platforms like iMessage, Google Docs, and Zoom. While these workers prefer faster forms of communication, they have also expressed fatigue from the number of emails cluttering their inboxes. 

Another survey helmed by Babbel, a language-learning platform, discovered that “Gen Z workers considered the volume of work emails they receive stressful.” Moreover, 36% of this group admit to having over 1,000 unread emails in their inbox.

When Gen Z workers respond to emails in the workplace, they put their twists on the messages to make things feel less strict. It is common for this generation of employees to include everything from memes to abbreviations, emojis, and even slang when communicating while on the clock. 

“Their response to this email just said, ‘Hey boss, let’s f’in go,’” Liz Giorgi, CEO of e-commerce content creation platform Soona, told Fast Company. “I would be lying if there wasn’t like a moment where I thought, ‘Oh God, should I have hired this person?’” she said. “But in retrospect now, I’ve come to realize [Gen Z] wears their emotions on my sleeve, and they were really excited in that moment.”

According to the Pew Research Center, anyone born after 1997 is considered to fall into the Gen Z category. In 2018, the company decided to use 1996, “the last birth year for Millennials, for our future work.”

Giorgi also blames their approach to communication on the influx of messages that Gen Z workers are subject to by way of virtual work tools like Microsoft Teams or Slack. 

“The Slack-ification of work, which is a much more informal kind of communication, has bled into our email style and reduced the intensity,” she explained.

What’s more, a current TikTok trend is exposing the way that Gen Z workers sign off on emails, which is almost just as informal as the way that they communicate via the aforementioned virtual workplace tools.

Young workers are ending emails with phrases like “Lukewarm regards,” “Bless up,” and “Another day, another slay,” according to the viral TikTok clips.

For HR consultant Kate Walker, the shortened messages and slang may be funny on social media, but there is still a duty to “effectively communicate” in a work setting. “Suppose there’s a legal issue and there’s a request for documents,” she told Fast Company. “You’re in the courtroom, and you see emojis and abbreviations. I don’t know if that’s going to be the best look.”

When people quickly had to adapt from working at home during the 2020 COVID-19 pandemic, the culture of the workplace shifted forever. In addition to Gen Z workers’ love of a shorter, wittier form of communication via email, many companies shifted the attire that employees must wear in the office. 

A Gallup poll confirms that only 3% of workers still wear business professional attire to the office, so it may only be a matter of time before the ways workers are expected to communicate via email could undergo some changes. 

RELATED CONTENT: A Fresh Approach To Gen Z Career Development


Former Southwest Air Supervisor Sues For Racial Discrimination

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Joseph Pitts, a former Southwest Airlines supervisor, filed a lawsuit against his former employer on July 29 in San Mateo County Superior Courts.


Joseph Pitts, a former Southwest Airlines supervisor, filed a lawsuit against his former employer on July 29 in San Mateo County Superior Courts, alleging that the airline engaged in racial discrimination, harassment, wrongful firing, and retaliation. 

“It makes me have this anxiety, it makes me feel, ‘Was it the right thing that I did?’ Because you’re jobless, you don’t have any income,” Pitts, 53, told The Mercury News.

Pitts said he was referred by other employees, including Black employees, as the n-word. He said he did not want to be addressed in that manner, but the behavior continued. “I didn’t want to come to work and hear that, ” he explained. “I knew it was going to stir up a pot, but these working conditions are not right. For a Fortune 500 company, I wouldn’t think they would have this going on.”

As a result of his repeated complaints to his supervisors, Pitts was informed that a ramp agent had allegedly threatened to lodge grievances against him in an attempt to get him fired.

According to the lawsuit, in October 2023, Pitts asked a Southwest Airlines administrator if he had heard about the frequent use of the n-word at the Southwest facility. After the administrator responded affirmatively, Pitts told him about three employees he alleged were targeting him.

Pitts also received threats from a manager to fire him over his attendance and threatened to fire or demote him, his lawsuit claims. In November, Pitts and another supervisor were talking in a supervisor’s office, next to the employee break room, and a ramp agent walked into the break room, where they allegedly loudly complained that workers were not allowed to “say the b-word and the n-word anymore,” then used profanity before saying the n-word.

According to the lawsuit, shortly after, when Pitts walked into the break room, he was glared at menacingly.

In December, Pitts was informed by a manager that he was fired after it had been determined that he failed to assist in the investigation. As a result, Pitts had to go into his retirement funds and has yet to find a job. His sick wife has puts off necessary medical expenses.

“Why would you do this to somebody who was trying to make changes, who was trying to tell you that these people are violating company policy?” Pitts told The Mercury News. “Why would you do this to me?”

RELATED CONTENT: Pepa Denton Claims Southwest Airlines Wrongfully Booted Her Off A Flight


Should Wearing Shorts To A Job Interview Be A Red Flag?

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A viral TikTok video has people asking if it’s appropriate to wear shorts to a job interview.

TikToker @mtyreshiadaily posted a video claiming she was dress coded by a recruiter when she came in for a job interview wearing a white blouse, sweater, and black shorts. The recruiter rescheduled for another day but asked the creator to change.

“I just got dress coded during an interview and then they decided to reschedule the interview with me for tomorrow,” she said. “But before they rescheduled, the lady was like, ‘Would you like to come back, like go change and then come back?’ And I was like, ‘No.’”

She then stood back from the camera to give viewers a good look at her interview attire, including the shorts.

The video has been flooded with comments—over 27,000 to be exact—from followers and critics questioning why she thought wearing shorts to a job interview would go over well. On both TikTok and X, social media users wondered what the job was for. One user asked if Tyreshia was applying for a camp counselor position.

Another user asked if the job was for a lifeguard. “Was it for a lifeguard position,” someone else asked in the TikTok comments.

Some commentators accused the creator of clickbaiting because most people know that it is inappropriate to wear shorts to an interview. Other viewers were surprised she was asked back for the opportunity to interview.

“Offering to reschedule was very generous of them,” @thawhole9 wrote.

Other sympathetic viewers said the issue was more of a teachable moment than an attack. Wearing shorts in the office will always be looked at as a huge no-no, and most people won’t wear them even if the job allows it,” acording to GQ.

A career-guided article by job search engine Indeed laid out some guidelines on how to properly dress for a job interview. It starts by researching the company’s dress code. Even if it’s listed as casual, dressing more professional than the employer may be beneficial. It is also recommended to wear clothes that match the season and climate and, lastly, be yourself. It’s OK to show some personality, but more so by wearing bold colors to show how you will conquer the role.

John Hope Bryant Promotes The 40-Year Mortgage Over 30 Years

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Some critics don’t agree with Hope Bryant’s ideology.


Operation Hope’s Founder John Hope Bryant wants homeowners to pay attention to the 40-year mortgage over the 30-year one, Fortune reports. 

In a new op-ed, Hope Bryant highlighted how the standard 30-year mortgage route for homeowners may no longer be feasible with the rising costs of living in the United States.

“The 30-year mortgage has been the American standard for decades, balancing affordable monthly payments with a reasonable repayment period,” Hope Bryant said. 

“However, as home prices soar and interest rates rise, particularly in urban areas, even 30-year mortgages can leave many families struggling with unaffordable payments.”

Once a former advisor in President Obama’s administration, the nonprofit founder touched on the 30-year mortgage being a product of the Great Depression when Americans lived shorter lives. In 2024, people are living longer, with life expectancy hitting 80 years, according to Macrotrends. However, in today’s world, mortgage rates have doubled in a short period of time, which has put homeowners in fixed debt for three decades, especially if there is a low interest rate. 

The result is accidental landlords and people pausing selling. Hope Bryant quoted real estate agency Redfin’s chief executive, Glenn Kelman, saying the 30-year mortgage has “the perverse effect of keeping home prices high” due to the rising interest rates of the Federal Reserve due to inflation.

“Critics may argue that a longer mortgage term increases the total interest paid, but the benefits of affordability and access outweigh this drawback. For many, the alternative is indefinite renting, which builds no equity and leaves families vulnerable to rising rents and economic displacement,” Hope Bryant said. 

“A 40-year mortgage allows more people to begin building equity sooner, offering a pathway to long-term financial stability and sustained human dignity—a key element of the American dream. A pathway up the repaired economic aspirational ladder in America.” 

The entrepreneur suggests the layout of the 40-year mortgage, using the Federal Home Loan Bank (FHLB) system and federal subsidies for first-time homebuyers who finish financial literacy training. The concept combines extended mortgage terms with financial education, making homeownership more accessible while achieving economic growth. 

Some critics don’t agree with Hope Bryant’s ideology, claiming a longer mortgage term would just increase the amount of paid interest, but there are longer benefits aligned with affordability and access. The 40-year mortgage gives homeowners room to build equity sooner. The financial literacy portion equips first-time buyers with the necessary skills needed to navigate through finances effectively and potentially avoid predatory lending. 

He also feels the new mortgage trend can address the growing wealth gap in America that is often talked about by Democratic leaders. During the 2024 Democratic National Convention (DNC), former Housing and Urban Development (HUD) secretary Marcia Fudge and Rep. Ted Lieu (D-Ca.) gave some insight into presidential nominee Kamala Harris’s housing proposals. 

According to ABC News, Harris pledged to give up to $25,000 for down-payment support for first-time homeowners and a layout for new construction of three million new housing units to combat the housing supply shortage.

RELATED CONTENT: Celebrating Juneteenth with John Hope Bryant


Lauryn Williams Becomes Financial Advisor Amid Olympic Career

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As a certified financial planner, the former Olympian supports and educates younger athletes as an advisor through her firm, Worth Winning.


After a 10-year athletic career, Olympic gold medalist track star Lauryn Williams went from making a $200,000 annual salary with Nike to a $12-an-hour internship to expand on her current passion as a financial advisor and educator for younger athletes and professionals.

After a decade-long career in sports, Williams may have been financially secure by age 30, but now, at 40, she recognizes that her athletic earnings won’t sustain her for life. In an interview with CNBC Make It, the former Olympian, who studied finance at the University of Miami, discussed how she now focuses on financial planning for athletes and young professionals through her firm, Worth Winning, and serves as an ambassador for the CFP Board Center for Financial Planning.

After passing her CFP exam in 2017, following two unsuccessful attempts in 2013 and 2015, Williams sought an internship through her coursework and was brought on by a CFP firm owner. “It was a perfect fit for me,” she said. In her CFP bio, she stated, “CFP certification is a worthwhile journey…Helping people is the best part of the work.”

Williams, also a motivational speaker, retired from track and field in 2013 following an injury. She completed her Olympic career after winning a silver medal in the bobsled in 2014. Navigating the ups and downs of managing her finances throughout her career as a professional athlete fueled her desire to further understand the intricacies of finances.

“What people don’t realize, even with a $200,000 income, is that your agent takes 20% of that. And then you have to pay taxes as well,” she said. “The money doesn’t go quite as far as people think it does.” Experiencing situations with her financial advisors that weren’t suitable during her career prompted her dedication to helping others make smarter financial decisions.

“Olympic sports, in general, are kind of like the world,” she said. “You have a 1% that is earning very, very well and has more money than they will ever need, you have the vast majority of people who are getting by, and you have the people who are struggling.” Olympic headliners who rake in more than enough to live off of after retirement must organize their finances properly if they desire to never work again. However, for several of Williams’ gold medal-winning clients, they weren’t even making $100,000 a year.

Williams shared that spending all of her 20s as a competitive athlete triggered insecurities. She said she lacked real work knowledge while her friends were already pursuing careers as doctors and lawyers. She advises everyone to prioritize themselves by automating their savings and opening a retirement account.

Check out Williams’ 2022 interview with Parity as she discusses generating income for student-athletes.

RELATED CONTENT: U.S. Olympic Teams Shine: Soccer’s ‘Triple Trouble,’ Basketball Victories, And A Controversial Gymnastics Medal


How To Stay Mindful And Demure In A Narcissistic Workplace

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Here are some success skills that will help you navigate narcissism in the workplace


Dear FairyGodMentor,

How do I deal with a narcissistic boss? I’m afraid I’ll lose my job because he always gaslights me and it gives me extreme anxiety. He is causing me mental health issues. What do I do?

Signed, Cindy

Dear Cindy,

Thank you for reaching out and asking for help. It’s a very daunting experience dealing with someone who makes it virtually impossible for you to focus on your performance because of their negative behaviors and treatment. I understand how this manager and their treatment may feel all too consuming but nothing is more important than your health and well-being.

Here are some success skills that will help you navigate narcissism in the workplace behavior:

1. Identify the behavior

WORKPLACE, Bullying, return to office
(Photo: Yan Krukau/Pexels)

What feeds a narcissistic boss is manipulation and control. A common tactic that you may have experienced is gaslighting.  Gaslighting is when you’re made to doubt your reality. It’s essential to realize this is “their stuff” and not “your stuff” to own.  Remember that your worth and value are not wrapped up in anything they may say or do.

2. Keep your receipts

follow up, email, contact, birthdays, small stuff, LinkedIn, message, conversation point
(Photo: Katleho Seisa/Getty Images)

I often suggest leaders document conversations and interactions to account for their direct reports’ behavior and performance. I share the same advice for direct reports. Keep detailed accounts of the treatment you’ve encountered, especially when you’ve felt gaslighted or manipulated. Documentation serves two purposes, it’s a record of what’s taken place should you need to escalate the matter to Human Resources (HR) or your compliance department, and it will ground you in reality if you start to doubt yourself.

3. No is a complete sentence

phone call, debt, collections, FTC, communicate, rights, federal trade commission, collections, debt, trips
(Photo: Anna Shvets/Pexels)

This may feel impossible at this time, but it’s critical to set clear boundaries. There’s still time to set them! You can set boundaries with this type of boss in several ways: removing yourself from any conversations that aren’t professional, restating or reframing what was said when you feel that manipulation or personal attacks are being made, and working your self-management skills by regulating how you respond to this type of behavior.

4. Get help

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Photo by FG Trade/Getty Images

Asking for help is not a sign of weakness. It’s a sign of strength! You’ve already flexed your “get help” muscles by sending this note over to me. Being treated this way can feel very isolating, but don’t be ashamed of asking for help from your support system. Your support system could look like your family, friends, a mentor, or a therapist. If you feel that this person is violating law, policy, or your physical and/or psychological safety, talk to HR – immediately. HR can step in, document your concerns, and take additional corrective action steps.

5. Don’t stop thinking about tomorrow

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(Photo: Getty Images)

You may want to take a pause for the cause and think about your future. Dust off that resume, keep in touch with your network, and maybe enlist the support of a career coach to keep you motivated on your path to career success. I know a great coach if you need one! (hint, hint).

6. Self-care isn’t selfish

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(Photo: Getty Images)

This whole workplace experience has taken a toll on you! It is not selfish to prioritize self-care.  Self-care isn’t always taking bubble baths and eating bonbons. Do what energizes you. Take on activities that decrease anxiety and keep you feeling grounded. Whether it’s taking a break to breathe a few deep breaths, exercise, or meditation. Take a deep breath right now. Do you feel that air in your lungs rushing in and escaping? That’s your body reminding you that there’s only one you in the world and you have a lot of magic to do while you’re here. You matter!


Cindy, your career is very important, but your mental and physical well-being are just as important. You can always make more money, but you can’t make more time. Protect your peace at all costs. Self-advocacy gives you your control back. When you raise your voice, you raise your value. You have the power to create the type of work environment that builds you up and doesn’t tear you down. You can decide to bloom where you’re planted or uproot yourself and plant yourself in another garden where you’re valued and respected. The choice is always yours to make.

Keep your head up, Cindy! You got this!

With love and light,

Your FairyGodMentor®

Have a question about handling a micromanager, are you having difficulty navigating spaces because of your hair, is work stressing you out, do you need support coaching poor performance or are you wondering how to negotiate and get the job offer you desire, effectively? Do you have any questions about career and leadership development? 

Ask Your FairyGodMentor® here.


Joyel Crawford, Fairygodmentor, Ask Your Fairygodmentor, Column
(Image courtesy of Kirsten White Photography)

Joyel Crawford is an award-winning career and leadership development professional and the founder of Crawford Leadership Strategies, a consultancy that develops empowered, results-driven leaders through engaging leadership development coaching, training, and facilitation. She is the author of the best-selling book and audiobook Show Your Ask: Using Your Voice to Advocate for Yourself and Your Career.