insight magazine

5 Traits of a ‘Best Boss’

Becoming a Best Boss should be the focus of every business leader. Here’s how to do it. By DUNCAN FERGUSON AND JAY SCHERER | Fall 2018


"You made me a better person... not just a better leader. You made me learn how much more people can do when they feel supported and appreciated. You taught me to take chances, celebrate success, and appreciate that if I don’t make mistakes, I’m not challenging myself enough! Thank you!”

Have you ever worked for someone who made you feel this way? If you’re lucky enough to have worked for a Best Boss, this relationship likely had a profound impact on your performance, your career, and your life. And if you are, or aspire to be, a Best Boss, you will have that same impact. We think everyone should plan to be a Best Boss. So, here’s how to do it.


Chicago-based consultancy Lead Well LLC, in partnership with Vantage Leadership Consulting, invited individuals across many demographics and working environments to answer seven open-ended questions about their perceived Best Boss. Survey respondents repeatedly highlighted five integrated behavioral traits:

Best Boss SystemLeads With a Higher Purpose – A Best Boss has a purpose beyond self-interest and profit that is put into action on behalf of the individual.

Activates Potential – A Best Boss observes, values, and takes steps to activate the present capability and future potential of the individual.

Grants Autonomy – A Best Boss imparts knowledge, business acumen, and big picture thinking, and establishes an autonomous space for the individual to perform.

Provides Pervasive Feedback – A Best Boss seamlessly uses frequent and diverse feedback to constructively shape, reinforce, and/or modify behavior.

Encourages Risk Taking to Accelerate Learning – A Best Boss fuels reasonable risk taking to assure learning and realizes that mistakes are a natural part of the growth process.

Behind these five Best Boss traits is a contemporary leadership philosophy — shared success. Being a great leader is not just about work and careers, it’s also about supporting an individual’s success by focusing on their personal needs. It’s about creating an energy in someone, so they achieve their aspirations, and therefore yours and your organization’s.

Leading from the point of view that the organization’s needs dominate simply doesn’t work anymore. At the same time, we also know that an individual’s needs cannot always be the top priority. Instead, great leadership today must be about building an energized balance between individual and organizational needs.


Unfortunately, all too often we tend to work for bad bosses. Our society loves to focus on bad boss experiences. In 2011, the movie “Horrible Bosses” was a comedic hit. is dedicated to helping people deal with difficult bosses. According to this website, half of us would fire our boss if we could. Research has increasingly focused on the impact of bad bosses. Gallup surveys regularly tell us the top reason people quit their jobs is because of their bosses. A 2008 study by Swedish scientists even found that males were 35 percent more likely to have a heart attack if they worked for a bad boss. On and on it goes.

We also know that the accounting and finance profession faces several challenges directly linked to the cultures within organizations and the business practices driving them. The Illinois CPA Society’s INSIGHT Special Feature, “The Culture Conflicts,” highlights many of those challenges and asks us what we can do about them. In many cases, change must come directly from leadership — aka the bosses.

Our goal here is to help you build the mindset that a great leader, a Best Boss, must focus on connecting, engaging, and retaining diverse talent. As the “war for talent” worsens, this type of focus is critical for your business to remain competitive in a tight labor market. Your ability to differentiate yourself as a great leader, and your organization as a great place to work, materially impacts your business because, done right, you’ll be better able to attract the best candidates, build diverse teams, and motivate each worker to reach their fullest potential.

In other words, as a Best Boss, you can help change firm and corporate cultures, drive solutions to the succession planning struggles so many organizations face, and truly drive the development and shared success of your staff.


To be clear, leading is more than connecting, engaging, and retaining. It’s also about aligning, executing, and achieving. A great leader must get results. It’s “the how” we’re talking about here. And the how matters now more than ever. Here are some steps you can take to become a Best Boss:

Lead With Your Values – A Best Boss is a values-based leader who consistently places the needs of individuals ahead of needs of themselves or the organization. Display a strong moral compass. Have compassion for your people and their lives outside the job and assure them that your performance expectations need not be at odds with integrity.

Learn How You’re Viewed as a Leader – Conduct your own survey or ask your organization to perform a 360 review. Also ask for candid feedback from trusted friends and employees. What are the facts regarding your leadership style?

Put a Plan in Place – Closing the biggest gaps between the type of leader you aspire to be and the type of leader you are today should be your primary focus. Start with one area for improvement. Get input on how to improve. Then solicit feedback on how you’re doing. Once you’ve improved, move on to the next area for improvement.

Aspire to Be Called a Best Boss – Best Bosses display a host of characteristics foundational to forming great relationships with their direct reports. Descriptions of Best Boss characteristics include humble, authentic, positive, optimistic, “can do” attitude, fair, ethical, has a sense of humor, thoughtful, thorough, and respectful. At the core of these traits is respect. It’s simple; treat people how you would like to be treated. Treat people like people and remember to explain why you need something when giving direction. Sell more, tell less.

Create a Feedback Expectation – Rather than always waiting for formal performance evaluations, a Best Boss makes real-time feedback a routine part of the supervisor-report relationship. Try to balance sharing constructive, respectful criticism with providing positive recognition for work well done.

Have More Consistent Discussions – Hold regular one-on-ones with your team members, and ask some of the tougher questions so many leaders try to sidestep:
• What is important to you? What are your needs? What gives you energy?
• What are you good at and like to do? What are you not as good at that you would like to improve?
• What is your view of what is needed for success in your role? How are you doing?
• What more can I do to support you? What more can the organization do to meet your needs?
• How can we work together to put a plan in place to create shared success for you and the organization?

Focus on Developing People – Today, more than ever, younger generations within the workforce want to quickly learn, grow, and develop as professionals. They know they must continually build their skills and capabilities if they’re going to stay competitive in a very dynamic marketplace. That said, it should be no surprise that the most common Best Boss behavioral trait was “activating potential.” To be a Best Boss, you must help people understand the potential they possess. Then make it your mission to actualize it by building real developmental plans, supportively pushing direct reports out of their comfort zones, providing them opportunities to grow their skills, and advocating for them to perform to their best potential.

Connect to the Whole Person – All people, but especially your young and diverse talent, want to be thought of not just as employees, but as the unique individuals that they are. You must connect with your people on a deeper level, understanding that work is only one part of a rich life.

Being a great leader and a Best Boss in today’s workplace requires a much more proactive and personally engaged approach than in the past. What that means for accounting and finance leaders today is that the focus must not only be on the numbers but also on the people. It’s within you to drive change, create energy, and overcome many of the cultural and leadership challenges the profession faces.

So, are you going to be a Best Boss or a Bad Boss?

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