Best Male Bosses: What Makes A Guy Great To Work For?

04adc0ce47935481d71f461f188b14bb-originaWomen Share Their Experiences

Photo courtesy of Benjamin Disinger.

By Raina Lipsitz. Cultivating trust between managers and those they supervise is essential to creating productive working relationships and improving an organization’s overall performance.

Yet women often see their relationships with their male bosses differently than their bosses do, and, according to Catalyst’s study, Building Trust Between Managers and Diverse Women Direct Reports, diverse women often experience even greater challenges than white women in forming trusting relationships with their managers.

The women we spoke with represent a range of industries, spanning the profit, nonprofit, and academic sectors, but several common themes emerged. Below we share a round-up of the most compelling stories we heard and a summary of what they taught us.


I have the best boss I've ever had right now and he's a man. I've actually had only positive experiences working for men!! What makes my boss so great? He is genuinely dedicated to my professional success and growth. He is interested in my opinion, and asks for it, and lets me know he appreciates it. He asks how I am doing and wants to know the answer. He regularly tells me that he appreciates my work (and because of this, I would probably be willing to sort a spreadsheet of 14,000 names if he asked me to, because he asks for things in such a good way). He is very direct—no BS. I never feel scared to ask for help because he encourages me to ask questions.
- Rachel M., Associate Director

My best boss-turned-mentor spoke to me like I was a professional well above my actual experience and years, at the very beginning of my career. He somehow made me feel like an equal while communicating with humor and good will what I lacked and where I needed to grow. He was always invested and committed to our work but never took the job so seriously that it compromised his treatment of me—even when I screwed up royally. Jeff always values taking care of yourself and others, by doing good work but keeping the work in its rightful place. This emphasis on what really matters gave me and his other employees the freedom to do a great job without fear. He continues to be a friend, colleague, and mentor and his presence in my life is invaluable.

- Stephanie W., PR consultant

I haven't had much experience working in Corporate America, and I've mainly worked for women, but a few of my bosses have been men. When I was a paid intern at the nonprofit Public Agenda, my male boss did a really great job of treating everyone the same. Male, female; old, young; black, white; intern, full-time employee—he clearly didn't play favorites, and it was refreshing. I know a lot of advice in this area is along the lines of "give women extra opportunities," but I think it's also important to treat people equally and not make women or minorities feel like they're in constant need of remediation.
- Rebecca T., Senior Associate

My boss, Raymond Happy of CCS (a fundraising consulting firm), is an outstanding example of what a male boss of a largely female staff should be. He knows that his heavily female and early-mid-30s consulting team will have a high incidence of life milestones, particularly getting married and starting families. Commensurately, Ray has worked with several talented women to provide as much time off as they need, with job security (albeit largely unpaid), and to give them high-level assignments which can be completed on a part-time basis when they return. Overall, Ray's approach to management is to invest in talent, by nurturing promising professionals and making sure they feel appreciated and valued. His respect for his team members' intelligence and work ethic is evident in his one-on-one and group interactions. All of this lends itself well to managing a high-performing team regardless of gender, though at the moment his approach benefits a much higher percentage of women than men.
- Amy S., fundraising consultant

What I appreciated most about my best male boss was that he was a good listener, first and foremost. He was also very fair and applied the same rules to everyone. He was smart and knew a lot about the company—the business and the culture—but he was still a humble guy. I really appreciated that as a leader, he demonstrated real humility and openness to learning from others, both young and old. Also, he didn’t make assumptions about me—he’d ask about my thoughts/feelings/experiences. Lastly, he gave me a lot of autonomy to do my work, and be creative about solving problems.
- Jane P., Vice President

The only male supervisor I’ve had was terrible, yet I think that was due not to gender differences but rather to his immaturity and insecurity. My advice would be: Support your female employee when she tells you a client relationship is not functional and allow her to help resolve the situation.

While working for this man, I was assigned to a male client in a heavily male-dominated field. The client and I disagreed on how best to complete our project, and he was openly hostile to me in person, on the phone, and over email. I kept my supervisor informed of this behavior. Ultimately, the solution my supervisor arrived at—without my input—was to phone the client outside of my presence, listen to his side of the story, remove me from the project, and replace me with a younger, less experienced male colleague. My supervisor called me into his office, after the fact and in the presence of my replacement, to explain his decision. After weeks of hostile treatment from the client, I was denied the opportunity to help resolve our dispute. This left me feeling as if I were the one at fault, incapable of resolving issues myself. And, of course, my replacement met with the client and immediately reported back about his hostile behavior, compounding the resentment I felt for not having been listened to in the first place.
- Lenore W., Executive Director

I worked for 11 years in a summer program designed to help underserved community college students transfer to and succeed at 4-year colleges. The challenges of the transition (academically, socially, etc.) were different for every student. The faculty and staff assembled once a week for a meeting to discuss each student's work. I valued these staff meetings a great deal for an unexpected reason: because it became clear that the director had assembled a staff composed of people who all had very different personal and intellectual styles, and he was committed to getting excellent work from everyone—not in spite of, but because of, our differences. I think it's important for a boss to value diverse (and sometimes even oppositional) professional styles and strengths—I learned that lesson the hard way in another situation by foolishly wishing my staff were more like me! What could have been frustrating about working with a group of such different people became professionally illuminating for me. The program’s director modeled his commitment to diversity with a light touch and a firm yet low-key way of handling difficult situations. In an amazing way, he modeled his staff's diversity on a principle similar to that which we applied to the students: by recognizing that each person succeeds in a different way, and that our individual strengths can be honed in a collaborative environment.
- Sarah B., Associate

To sum up, a great male boss should:
  • Treat his employees, male and female alike, with respect;
  • Trust the people who work for him and make sure they know he’s on their side; and
  • Ask for their feedback and include them in decision-making and problem-solving.
And, according to one interviewee who is a Senior Associate within her organization, he should not:
  • Go out of his way to act macho around women, especially those who hold higher/more powerful positions than he does. My male boss at my first job post graduate school did this: he always copped a "devil may care" attitude at work, especially around his female superiors. It made him seem like he had something to prove. It was strange and alienating and I could tell he was making an effort to act this way (vs. it just being who he was/how he normally behaved).
  • Treat everyone else like they are inferior and/or stupid. I had a HORRIBLE boss when I worked as a server at a restaurant after I first moved to NYC. He was in his 40s and clearly very intelligent, but I think he had a lot of deep-seated insecurities because he’d never graduated from college. Don’t take your personal insecurities out on your employees!
What strategies have you pursued to build productive working relationships with your female direct reports? What seems to work well (and what doesn’t)? Share your stories below!
Posted by Mike Otterman on Feb 22, 2013 11:07 AM America/New_York

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Thinking about the he should not section... Why do some guy leaders act macho around woman or treat them and others in an inferior manner? Perhaps this has less to do with woman and more to do with their own personal insecurities and/or simple lack of confidence? Confident leaders have nothing to prove. Those who lack confidence often try to hide behind exaggerated projections of what they wish they were or what they think they should be. This is no different than the 'personalities' often witnessed when out at the club or a social gathering. Macho guys, braggarts, and tough guys, who want everyone to know their someone other than who they are. Lot's of wasted energy on a facade that typically accomplishes the opposite of what was envisioned. Perhaps, in the workplace, when we see these types of leaders we should seek to help them work on or get help for their confidence issues? I'm definitely not suggesting we accept or excuse this kind of behavior, at the same time maybe if we try and look past the surface into the actual problem we can better understand what's happening. This could potentially lead to a win-win for everyone?
  • Posted Thu 18 Jul 2013 09:32 AM EDT
I'd like to see an article that highlights male-female conversational dynamics in the workplace. I have to be on conference calls a lot, and am in a male-dominated profession. Males traditionally allow themselves to 'have the floor' more and interrupt the females more often. I have asked my current lead to respect this and to partner with me when I get interrupted (which is very often), but he ignores my requests. Matter of fact, he is one of the chief interrupters. Often, when interrupted, I'll circle back after the interruption and say, 'as I was saying before I was interrupted . .' and finish my thought. But it's dicey.

There are peer-reviewed studies on the topic of conversational male-female dynamics.
  • Posted Sun 05 Feb 2017 12:47 AM EST
Great point, Jan Buitron‍. This is something that guys can work to be conscious of.

Check out this blog by Cliff Leek,‍ 3 Ways You Might Be Silencing Women (And A Checklist For Fixing That): 

Also related, Are You Manterrupting Your Female Coworkers? by terry howard‍:
  • Posted Fri 24 Feb 2017 08:49 AM EST



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