May 8th, 2008
Embracing your inner Good Boss: Becoming an employer without losing your nerve
Hello! This is Lauren, one of the authors of The Boss of You: Everything a Woman Needs to Know to Start, Run, and Maintain Her Own Business. This post is the third installment of a four-part blog book tour we’ve undertaken to support the book’s release. (To read the two previous blog tour posts, visit Anti9to5Guide.com and FeliciaSullivan.com.) We’re delighted to be guests here at All Things Girl!
Our theme this week is hiring help, and today I’m going to focus on the psychological side of transitioning from “boss of you” to “boss of them.” A lot of small business owners struggle with the question of how to stay true to their personality and values as an employer. We have first-hand experience with this, because we went through the same struggle ourselves.
When we started our web design company eight years ago, we had this notion we would never hire staff. We’d just stay a teeny-tiny, two-person company forever, because that felt nice and comfortable. Manageable. And egalitarian. Two partners, fifty-fifty, with equal say and equal pay. That worked well for quite a while, too. But then we got insanely, brutally busy — our friends stopped recognizing us, “spare time” became a nostalgic dream, and it became abundantly, painfully clear we had to hire someone to help with the workload.
Trouble was, we had no idea how to be bosses.
Okay, yeah, we’d both managed people before, in a sort of middle-management capacity. But we didn’t love it, and we didn’t relish the thought of doing that again: having to be in charge of someone else’s schedule and work flow, checking their work, holding them accountable… It all felt like an awful combination of drudgery and nagging, and we wanted no part of it.
Obviously we weren’t exactly looking at the shiny side of the coin.
What we’ve come to realize about being an employer is that it affords you a marvelous opportunity to be The Good Boss — you know, the one who paid you well, respected your strengths, kept her expectations reasonable, and gave you just the right mix of challenging work and projects you could ace blindfolded? Okay, that description may not ring bells for everyone, but either way, when you hire someone to work for you, you get a chance to make someone’s work life pleasant.
When we woke up to that reality, we understood that the dread we’d been feeling about becoming bosses was actually fear that we would be bad bosses. We hated the idea we might turn into versions of the employers we had most fervently disliked — the guy who announced to his staff their salaries were suspended indefinitely, then sent someone out to pick up the keys to his brand-new Porsche, for example. Even though we’d both had good bosses, too, it was the bad ones that stuck out and made us reluctant to claim boss-hood.
As with most things, though, awareness of our own shortsightedness was the first step to recovery. We looked each other squarely in the eye and decided we’d better get over our own hangups right quick if we were ever going to take a vacation again. And we sat down and figured out what steps we could take to be the best employers we could.
Obviously there’s way more to being a good boss than we could possibly cover in a single blog post, but here are a few fundamentals:
- Know thyself. To hire the right person, you need to have a pretty good idea of where your strengths and weaknesses lie. Maybe you’re an ideas person but you’re not so hot with the details — in that case, you’d probably be best to hire someone who can run things through with a fine-toothed comb for you, leaving you to bask in your happy creative play zone. On the other hand, you might be a person who excels at talking to clients and prospective customers, but whose mind wanders a little when doing repetitive tasks; in that case, look for someone who doesn’t mind a job that involves little social interaction and a fair amount of sameness from one day to the next.
- Personality matters. In a small business, it’s integral that everyone trusts each other (at a bare minimum) — and ideally, you want everyone to get along swimmingly. Make no mistake, this is a serious relationship commitment you’re making; you’ll be spending an enormous amount of your waking life together, and although you’re not advertising for a best friend, you ought to make sure that you share enough common ground that you’ll be able to interact comfortably and communicate well on a daily basis.
- Spell it out. If you know you’re looking for a details person, include keywords like “meticulous” and “detail-oriented” in your job posting, and ask candidates you interview for examples of work they’ve done that shows they embody those qualities. Take the time, in both job postings and interviews, to outline your vision for your company, and the values you hold dear. You’re much more likely to find good employees, and make a strong match, if you explain to them clearly how they’ll fit into your company’s future.
- Respect the power dynamic. Being the boss isn’t easy for everyone; some of us have trouble with the idea of having power over others. The good news is that you don’t need to be bossy to be the boss — but you do have to be the leader. It’s your job to establish clear expectations, set priorities, and follow up with your employees (or contractors) to ensure they’re holding up their end of the bargain. At the end of the day, you won’t be doing anyone any favours by being sheepish about the power you hold; it’s much easier for everyone if you can learn to be direct and unapologetic about the fact that you’re the one writing the paycheques.
We could go on and on, but let’s stop there for now and turn it over to you. What are your hiring challenges? Do you have questions or concerns about making your first hire? Share them with us in the comments and we’ll do our best to answer. To sweeten the deal, we’re offering a free copy of The Boss of You to one randomly-selected commenter, so pipe up!

















May 8th, 2008 at 10:38 pm
Hi - I searched tonight under ‘employer or friend’ - like you guys I am a capable and efficient individual , now my business is growing like a weed ( thank goodness !). I added an employee last summer, first part time and now full time with another part timer just started.
Problem:Employee #1/ we both have a lot to share,kids at the same school etc ….but employee is going through a tough ,marriage break up situation..bending my ear way too much during work time . I have kindly, with humor (and occasionally by snapping ) asked her not to talk to me about personal stuff during work time but it just does not sink in . My dilemma is that I really feel for her and her kids and my husband and I try to assist her by giving her playdate breaks etc..she has proven through her work to be smart, efficient, capable and trustworthy - therin lies the dilemma !!! anyone else have this experience ? I don’t want to be thinking of her issues all the time, I want to get on with the joy of small business with efficient and happy employees.I would love to hear responses from employeres and employees alike.
May 8th, 2008 at 11:00 pm
ps I just bought your book !
May 9th, 2008 at 10:06 am
Hi, Donna! Hmm, that *is* a dilemma. In a small office, the lines between professional and personal communication often blur, and part of your role as the employer is to establish and maintain boundaries of what’s appropriate in the office.
A couple of thoughts come to mind:
Set a time to meet with her privately, to talk about the issue. If it’s difficult to have a confidential conversation in the office, you might want to ask her to meet you elsewhere, though I would avoid “doing lunch” as it might confuse matters by implying it’s a social date. Set out your concerns as directly as you can, and be sure to lay out the business case.
She *is* going through a very difficult time, so rather than stating things in a personal way (e.g. “I find it annoying…”), keep things professional and explain to her that you are concerned that it’s affecting productivity in the office. You may want to ask her to consider that as a senior employee (I’m assuming by “Employee #1″ you mean she’s the first person you hired), you look to her to set an example for other staff, and that you need her to try and keep the personal conversation to a minimum.
It can be very effective to simply state the problem, and then ask your employees to help you solve it. You might say something like, “I wanted to talk to you about the stuff that’s going on in your personal life, because I’m concerned that your stress levels are affecting your work. I know this is a really hard time for you and I want to support you in any way I can as your employer, but I also need to balance that with the business needs, including making sure that we have clear boundaries in the office with respect to personal conversation. I have some ideas about how to resolve this, but I’d love to hear your thoughts, too.”
In my experience, good employees know there’s a problem as well, and are usually relieved to hear it stated in the open as a challenge to solve together.
A couple of other thoughts…
1) If you are indeed friends outside of work hours, you might suggest making a regular dinner or coffee date after work, to give her a chance to vent in an appropriate venue.
2) I might also suggest she take some time off, to deal with her breakup. You can decide whether this would be paid or unpaid time, but in my opinion, you could quite possibly justify a couple of paid days’ leave if it’s going to improve you and your other employee’s efficiency levels. In any case, you could ask her whether she needs time off to deal with it and see how she feels; it may be that when you suggest it, she’ll recognize the gravity of the situation.
3) Since it sounds like you two are quite close, use your knowledge of her personality to help figure out her motivations. To give you a personal example of what I mean, I’ll tell you a story that recently took place in our office. My maternal grandmother passed away a few weeks ago, on the last day of a week-long vacation I had taken. Because I’d been off work for a week, I went into the office the next day and buried myself in work. A day or two later, though, I found myself suddenly overwhelmed with grief while I was in the middle of a meeting with my business partner, and she gently suggested I take the rest of the day off. I resisted, telling her, “I just need to get this out of my system, but I’ll feel better if I can do something productive.” She tried two or three times to send me home, and each time I got more stubborn about staying. Finally, she sighed and said, “Lauren, I’m going to feel really bad if you don’t go home right now. You lost your grandma and it’s a big deal and you need to go home.” A smile broke across my face because I realized she’d played her trump card: She knew I’d only look after myself if I thought it was doing someone else good. So I sent off a couple of emails to clients letting them know I’d be responding to them in the morning, and went home to grieve privately.
I tell this story because when I was in that head space of being emotionally overwhelmed, I was consumed with the idea that I had a duty to fill at work and that looking after my personal needs was secondary. But I wasn’t paying attention to the fact that the presence of an emotionally overwhelmed person in the office is very disruptive. Emira found a way to send me home firmly without making me feel badly about it. If you can discern the thing that will give your employee permission to look after herself on her own time and take it out of the office, the problem may just take care of itself.
I hope this is helpful. If you have other thoughts, please post them.
Congratulations on your success — I hope your business continues to prosper!
And thanks for buying the book.
May 14th, 2008 at 9:28 am
[…] Don’t forget you can comment on our guest blog post from Lauren and Emira and be entered to win a free copy of The Boss of You. Worth it, trust me! These icons link to […]
May 16th, 2008 at 8:59 am
Wow, this sounds like a great book. I hope that the library has it so I can read it. I’ve thought about starting my own business for some time, but financial commitments are difficult when you can barely afford your normal bills.
I’m glad that so many women are out there starting their own businesses and filling niches successfully. I hope that one day I can do the same.
May 18th, 2008 at 9:49 am
Interesting article.
May 18th, 2008 at 10:17 pm
I think your book would even be good for me in dealing with a difficult boss. For the first time I find myself in a middle management position and I”m often lost on what to do with people under me. When I started this job I told myself it would be the last one I ever have working for someone else. After this, I”m going to be a business owner. I’m definitely going to have to find your book
June 13th, 2008 at 6:46 am
[…] and Maintain Her Own Business by Emira Mears and Lauren Bacon. Lauren guest blogged on ATG about Embracing your inner Good Boss. Every woman starting their own business, thinking about starting their own business or in their […]