It’s four answers to four questions. Here we go…

1. The founder’s nephew took over, and things are bad

For 10 years, I’ve been working for a small family-owned company (about 20 employees). We have always been 100% remote. I have two people working directly for me and I am happy with their work.

However, the company has not been doing well. The founder, now well into his 80’s, is semi-retired. Day-to-day management has fallen to his nephew, “Jack.” Jack and I get along but he doesn’t have much experience in our business, while I’ve been in it for nearly 40 years. Another nephew, “Eddie” (Jack’s cousin), is the sales manager and has ambitions wildly beyond what we can achieve, especially as we’ve had recent budget cuts. I think we can succeed if we lower our sights and close down unprofitable product lines, but Eddie keeps insisting he can make a go of them, despite years of terrible performance. I have experience in those product lines and I know we cannot come close to succeeding with our resources. Eddie has virtually no experience with those product lines, but doesn’t want to admit defeat. Jack is weak-willed and won’t make any tough decisions. He won’t even really learn the business: We’re a heavy IT-based company, but Jack asks me to send him PDFs of my work as he finds logging into our system “too complex.” It’s also clear that for family reasons, Jack and Eddie have a prickly relationship.

My staff and I haven’t had a raise in 18 months and not for several years before that. I had to make a small scene for the last raise, and now we’re doing even worse. Any suggestions for working this out?

This isn’t the company you’ve been working at for the last 10 years; for all intents and purposes, this is a new company, now that the management has changed. Unless you still have the ear of the founder and he’s willing to intervene with how Jack is running things, your best bet is to get out. (And really, even if the founder is willing to intervene, this is unlikely to get a whole lot better.) You gave it 10 years, it’s a whole different set-up now, and it’s time to go.

2. My coworker is obsessed with my horse

I ride and show an Arabian horse with my daughter. I have had pictures of my daughter and me with the horse at my desk, and coworkers are sometimes friendly-curious (what discipline, show them a pic, etc). But one coworker has gone too far. A few years ago, my coworker “Ed” worked with me on a project and asked to see a picture of the horse. No big deal. Then every interaction became about how pretty my horse was, and then regular unwanted texts about horses I ignored until I finally told him I was too busy to read them. The texts stopped and we resumed a cordial distant relationship for over a year and I was relieved.

Until a few days ago. He stopped at my desk and practically begged me to either send him or print him out a picture of my horse. I was creeped out, panicked, and said I would see what I could do. I have no intention of giving him a picture. That would be bad, right? I’ve taken all my horse pictures home and locked down or deactivated all social media that involves my horse and other pets (the animals had their own Instagram). Any advice on what to say to this guy would be great. Due to office politics I don’t want to escalate this; it would potentially make things worse for my boss, whom I adore and my department as a whole.

Reading this, my initial reaction is that your response is pretty intense. Ed sounds like he might be socially awkward and latched on to the horse as a topic to try to connect with you over, but did it badly. You told him to stop and he stopped, which is a good sign. His asking you for a photo a year later is weird, but not necessarily escalation-level weird (especially since last time you didn’t indicate he should never mention the horse again, just that you were too busy to read his texts).

But you’re the one interacting with him in person and you’re feeling creeped out enough to deactivate all your social media, so you might be picking up on something more. If he approaches you about your horse again, it’s fine to say, “The interest in the horse at work got too distracting, so I have a new no-horse talk rule, thanks for understanding.” If that doesn’t solve it, you’ll know you have a problem on your hands — but based on last time, there’s a decent chance that will take care of it.

3. Should I clarify my boss’s email to her boss and grandboss?

I’m a public librarian of over 20 years. My current manager leaves much to be desired in terms of communication and staff management, and it’s exemplified by the current issue I’m having.

My mother had a knee replacement in June, an operation that I informed my manager about via email and in person multiple times. I kept her informed through email of my leave plans and progress towards getting FMLA, as we weren’t working in the same building. It took me some extra time to get my FMLA paperwork completed and into HR for approval, and it wasn’t done by the date of my mother’s surgery.

On that day, my manager called me while I was at the hospital and, without asking how I was doing or how my mother was, she asked if my FMLA paperwork had been submitted. When I said no, she told me that my absence therefore was considered a “no-call, no-show” absence, and that if I didn’t report to work the next day, that absence would also be considered the same. I had planned to take the week off, even though it would be without pay (I had used up my paid leave for the year in part due to my caregiver responsibilities).

I was flustered and just wanted to get off the phone, so I acknowledged what she was saying, including her statement that she would send an email confirming our phone call. The email she sent was not just to me, but to her boss and her grandboss.

By that point, I was able to think and I replied to the email that I didn’t think my absence qualified as a no-call no-show and said I would be talking to HR, as well as asking that I might be extended some grace in this situation. I heard nothing from anyone in response, so after two days, I forwarded the email to HR.

Our chronically under-staffed HR department took three weeks to reply to me, indicating the absence did not count as a no-call no-show, since I had notified my manager in advance of my absence. They CC’ed my boss on the email, but they didn’t include her boss or grandboss.

Should I forward that email from HR to those bosses? Would this be seen as tattling? Given that my manager has been the subject of similar complaints from other staff previously, could I therefore frame this as more evidence of a manager who has not improved?

I’m dreading the end of the renovations to my branch, when I’ll have to start working with my manager again in person, so while I know sending the email might not be the smart thing to do, I kind of feel like I have to do it to keep my own self-respect and self-worth from going into the toilet.

(On the upside, my FMLA did get approved a few days after HR weighed in on the no-call no-show absence, so at least I’ve got that protection now. And with the start of a new fiscal year, my vacation time has been front-loaded, as is the practice in my library system, so I’m able to take paid leave now. So some of my stressors have been removed, at least!)

Forward it to them with a note like, “Just wanted to close the loop on this — HR confirmed this would not be considered a no-call no-show since I notified Jane in advance. (The FMLA also did get approved.)” It’s not tattling; it’s letting them know the resolution of something they were included on.

You asked about whether you could use this as additional evidence that your manager hasn’t improved. I wouldn’t spell that out when forwarding the email; it’s not the forum for it (unless you’ve had direct conversations with them about related problems with your boss in the past, in which can you could maybe say something like, “This is the sort of thing we were talking about”).

4. Changing my name after a divorce

I am waiting for a court to finalize my divorce after almost 20 years of marriage. For a variety of reasons, I have decided to switch back to my maiden name, which I haven’t used since I was 22 and barely starting out professionally.

My professional field involves state licensure and heavy regulation, so everything needs to match. I am fairly well known within my field, but I just switched companies into a director’s role. So I am meeting new people and onboarding with a name that’s going to change in about a month. In hindsight, I wish that the timing would have allowed me to do the name switch before I moved, but that’s not how it worked out.

I’m curious about the most efficient and least dramatic way to approach a name change under these circumstances. Because of the industry, I am going to have to update about three dozen or more licenses, system accounts, etc. It’s already a daunting administrative burden on top of the prospect of constantly explaining and dealing with people’s weird reactions to divorce news. Finally, my married name was far more unique than my maiden name, so I’m also worried that my professional reputation as Jane Snufflelupagus will get lost in the transition to Jane Doe. My divorce wasn’t dramatic, but it was draining and it took a long time. I’m ready to be done.

People will take their cues from you, so if you’re cheerful and matter-of-fact about it, they’re unlikely to have weird reactions. You can just say matter-of-factly, “I’m dropping my married name and switching back to Jane Doe.” Note that language doesn’t even mention divorce, just strips it down to the relevant facts, but it would also be fine to say, “I’ve switched back to my original name, Jane Doe, since my divorce.”

Since you’re worried about losing the reputation associated with your married name, one option is to include both for a while. For example, under your email signature you could include something like, “(Jane Snufflelupagus).”

You’re hiring for a new role at your company, your long-time friend happens to be in the market, you know the wonderful work they’re capable of, and boom. Great success can follow when you harness the power of a caring and supportive relationship to achieve your professional goals. But with unclear workplace dynamics and a power differential now entering the group chat, it’s also possible your once-steady friendship could be disrupted… or even destroyed.

Here’s how both your business and relationship can survive and thrive amid this major change.

Meg and Nicole: From best friends to boss and employee

Meg Behrens and Nicole Haisma first met at Lafayette High School’s freshman class orientation in summer 1998, striking up a solid friendship that continues to this day. When Behrens, founder and principal designer of Meg Behrens Design, was looking to bring on an additional designer this past year, Haisma and her functional life experience instantly came to mind.

Haisma designed the space and created the vision and aesthetics for In Bloom, a Paso Robles, CA restaurant she co-owns with her husband Chris. She also is a real estate broker who spent years staging homes and updating kitchens.

“I kept hiring junior designers who were great at drafting, but they needed a lot of direction,” Behrens says. “Running the business was already a full-time job, and I love the creative side too—but balancing both was overwhelming. I really needed someone with strong creative instincts and the ability to communicate well with clients.”

After collaborating on a test project, designing In Bloom’s tasting room Nix Cellars, Behrens officially hired Haisma to work for her firm on a per-project basis.

“With no risk, there’s no reward,” Haisma says. “We both kind of talked about how we could define the roles and delegate certain projects and we [thought], ‘Why would we not?’” 

Leadership consultant and psychologist Vincent Miles believes a key benefit of hiring someone you have a pre-existing relationship with is that you truly know that person and their quirks.

“You kind of know what you’re getting with that individual, where their strengths might lie and there’s less unknowns [than] if you’re hiring someone completely random.”

With previous new hires Behrens sometimes felt they were taking her comments personally, not as constructive criticism.

“It’s just completely opposite with Nicole, where I can tell her what’s up and the job gets done,” Behrens says. “We already have that comradery… [and] I’m not going to hurt her feelings over it…. sometimes I feel like you’re stepping on people’s toes, but at the end of the day [it’s] your vision [and] you need it done correctly.”

Arizona-based Behrens and California-based Haisma often collaborate over FaceTime and phone calls, addressing at the outset if the conversation will address a project or their personal lives. That’s helpful, Haisma says, in order to show up in the right role.

 “We kind of set those expectations,” Haisma says. “And so [we] can show up and just really be supportive depending on what we’re trying to have a conversation about.”

While someone else in the organization might feel apprehensive to float a new idea or voice a concern, given their lower position or limited tenure, Miles says that with a preexisting friendship, the subordinate position might be more comfortable speaking up.

Haisma is often able to take that approach with Behrens.

“[Nicole] might even say something to me like, ‘Oh, I don’t know, I kind of feel like we should go this way,’” Behrens says.

Given their relationship and the foundation of trust they already have, Behrens will then consider Haisma’s suggestions.

But be careful…

Miles thinks that the hiring person could easily fall into the trap of seeing their friend as an idealized version of an employee, or even a perfect one.

“We have to remember that they’re going to make errors and leave space for that so that we’re not frustrated,” he says. 

To maintain a peaceful environment, Miles says a boss should help set their friend up to be treated like any other employee.

“It’s really important that that individual is seen by their peers as an equal without preferential treatment, without any kind of favor.”

Haisma and Behrens believe salary should be discussed in advance, as finances often can be an uncomfortable topic.

“You need to be very direct and you need to set the expectations for the involvement and the amount of work that you’re doing and the compensation that you’re going to receive,” Haisma says.

To make sure you come to an agreement, Miles suggests navigating from a boss’s perspective rather than that of a friend’s, or bringing Human Resources into the negotiations. And if you’re unable to involve a third-party, Miles agrees with Haisma that communicating clearly is critical and will help take pressure off the relationship.

“For example, I’m not giving you a salary range or something specific because of how I feel about you. I’m effectively saying, ‘This is what the business can support. This is what would be fair and comparable.’”

Even if things appear to be going well, Behrens still advises that you have an exit strategy.

“Just have that clear definition of, ‘Hey, if it doesn’t work… it’s not going to ruin our friendship,’” she says. 

Still, that friendship will evolve. Miles says you might encounter a different version of your friend when they’re in boss mode.

“They might not be as soft or willing to hold your hand at times. And that relationship or that individual’s emotions might kind of ebb and flow based on how business is going.”

If like Behrens and Haisma you both are able to roll with the changes to your relationship hiring a friend will bring, you can also reap the many rewards.

“I can become a better designer because of the things I’m learning from Meg,” Haisma says. “And then some of the things that I’ve just been doing along the years, Meg is like, ‘That’s a cool idea….’ So we’re making each other better… owning our strengths, [and] pushing each other to keep expanding.”

Photo from fizkes/Shutterstock.com