The Boss Effect: Choose Your Boss Wisely

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Job seekers often take considerable time to research jobs and the companies while taking very little time to evaluate the bosses they’d be working for. But it’s important to be intentional about the people you choose as your bosses. Choosing the right (or wrong) boss can have a lasting impact on your happiness and career trajectory.

“You are in the driver’s seat; you have control over whom you do and don’t work for,” says marketing maven Nancy Richardson, who has held roles at Starbucks and Lululemon. “When you arrive at your existing job or when you are about to accept a new offer, you are choosing your boss. As long as you are showing up, you are choosing this person, so you might as well take advantage of the gifts your boss has to offer. I’ve had fifteen bosses and even the worst bosses taught me some powerful lessons when I looked beneath the surface. These gifts shaped me into the leader I am today.”

Richardson further discusses the how to choose your boss wisely and shares insight on the 4 kinds of bosses, what they have to offer and who is best for where you are in your career in the forthcoming book, Work Freely: Love Your Job. Love Your Life. [AsianDragonLady Productions, September 17, 2019], which she co-wrote with executive life coach Rochelle Davidson, CPCC, ACC.

Below, Richardson and Davidson offer some advice on how to choose your boss wisely.


How can job candidates go about choosing a boss wisely? (Rochelle)

Part one: Circle of knowing what you want

Before you start your next dialogue with a potential organization and/or leader, try the following exercise. The Power of Knowing What You Want, developed by my mentor and Lightyear Leadership founder Susanne Conrad (, is a simple, meaningful way to articulate and clarify what you desire—generally, in your life, or more specifically, in a boss. 

Step 1: Draw a circle on a piece of paper, the circle taking up 75 percent of the page. Step 2: Inside the circle, clearly and explicitly state everything you want in a boss. This may include qualities, skills, and behaviors, and it may also include how you want to feel when you work with this leader. This will be very personal to you. Some examples are “thought partner,” “champion,” “confident,” “humble,” “clear decision maker,” and “I feel empowered, seen, understood, and capable.” 

Step 3: Add color. Highlight or circle your non-negotiables—those qualities that you cannot live without— in one color and your “nice-to-haves” in a different color. 

Step 4: Outside the circle, write anything you don’t want in a boss, creating a clear boundary. It is important to take time to get clear on what you want and do not want. Again, this will be very personal, and some examples include “controlling,” “abusive,” and “not confident.” 

Part two: Interview Your Potential Boss

Once you know what you do and don’t want, you may interview your potential boss and be willing to make a choice based on their responses. Possible questions to ask your potential boss include the following: 

  • Who are you as a leader?
  • What are your current development goals as a leader?
  • What strengthens/energizes you as a leader? What weakens/exhausts you?
  • How do you deal with challenge/adversity/change?
  • When are you at your best?
  • When are you at your worst?
  • What would you count on me for?
  • What could I count on you for?
  • How would others describe you as a leader?
  • What significant failure have you experienced? What did you learn from it?
  • What has been the toughest yet most helpful feedback you’ve ever received?
  • What would happen if I disagreed with you?
  • Why would I want you as a boss?
  • Why would I not want you as a boss?
  • What can I learn from you?
  • What do you want to learn from me?
  • To what degree will I be able to influence change?
  • How much autonomy will I have? (Note: consider how much autonomy you want!)
  • What will my decision-making authority be?


What are the four kinds of bosses and what can each offer? (Nancy)

The New Boss: Weak Functional Expertise/Weak Leadership Experience

New Bosses tend to be over-promoted and placed in leadership positions before they’ve demonstrated the leadership acumen required for that role. They have an adequate level of intelligence, but they aren’t like a Smart Boss. They are less concerned about being the smartest and more focused on the status and power their title brings. However, they often don’t realize it is false power.  Lacking smarts and leadership, the New Boss tends to feel threatened and lacks the experience required to handle adverse situations, often leaning on Wise Bosses for advice. 

The Smart Boss: Strong Functional Expertise/Weak Leadership Experience

Smart Bosses exist in most organizations. They work very hard to be the smartest person in the room at all times, often trumping every idea and always having the last word. Smart Bosses can be the most abrasive type, yet they often don’t realize they come across this way.  

The Nice Boss: Weak Functional Expertise/Strong Leadership Experience

Nice Bosses are the best because they are, well, so nice. It feels good to work for them as they typically have extreme.  Had I chosen a Wise Boss in each of my roles, and never settled for anything less, it’s possible that my career could have gone further, faster.  However, because they have been in leadership positions for a very long time, they are often far removed from the work to the point where they have lost touch with the details of it.  I have fond memories of my favorite Nice Boss. 

The Wise Boss: Strong Functional Expertise/Strong Leadership Experience

Wise Bosses are calm, confident, and egoless. They have done the work themselves, earned their stripes, and grown into their leadership from the ground up. They have been guided and coached by the best and seek out a massive amount of leadership training wherever they can find it.  They are constantly learning and view feedback as a gift, welcoming it from every level of the organization. They view not only superiors as their coaches but also those who are subordinate to them. They lean into young talent and believe it is their role to coach and develop the next generation to be bigger, better, faster, and stronger than they were.  They are young at heart and have been around the block with decades of experience that gives them the wisdom to see the big picture and put even the greatest of challenges in perspective. They are vulnerable, compassionate, and generous,and they always make time for you.

I’ve learned from every single manager I’ve had: the Smart ones, the New ones, the Nice ones, and the Wise ones. Each has offered me tremendous gifts that I have taken to heart.  Remember that you always have a choice, and this choice can have a lasting impact on your career, so choose your boss wisely.


Can you offer some tips for dealing with a difficult boss? (Rochelle)

Get related. Get to know them as a human being. Understand what is important for them, what their motivations are. We are more likely to be able to work with someone, even if they are challenging, when we see them as human beings. And often, the more we do get to know someone, the less we actually experience this as difficult. 

Create boundaries. What are your non-negotiables that need to be in place in order for you to stay? What can you tolerate? What will you not tolerate? What are you willing to leave over? 

Know yourself. Be clear on what you are a stand for, who you want to be in the face of conflict and adversity, so that you don’t get knocked off your foundation in the presence of a challenging boss, colleague, human being. Even though someone may be challenging, you can still remain your best self.

Don’t take it personally. Someone’s difficult behaviour is not about you. Don’t make it about you.

Don’t let a ‘nice boss’ who won’t give you the coaching, feedback and direction you need derail your career. If you’re not having those conversations with your boss, despite your requests, find others who will support you. Mentors, team members, your boss’s boss. I know it’s not always easy to hear about the things you need to improve, however the impact of not knowing is that you won’t improve and it can have damaging consequences to your career.


What lessons have the worst bosses taught you? (Rochelle)

Nobody wakes up in the morning thinking “okay, how can I be a horrible boss/employee/human being today?” Yet a number of things – self-doubt, pressure, lack of self awareness, conflicting demands, not enough sleep to name just a few – can lead to behaviors that don’t serve. Know what those triggers are for you and how to recover from them so you are showing up in the way that you want. 


About the Authors

NANCY RICHARDSON began her career with a BA from the University of Washington and

MBA from Ohio State University. After more than twenty years of working in large, corporate environments, including Starbucks and Lululemon—where she put in insane hours and had little time with her family, and where others determined her worth—she decided to design her own life by tapping into the era of start-ups and passion projects, building meaningful brands, and working from home to spend more time with her family. She is the Founder & Principal Strategist of Dragon Lady and CEO of Mom ’n’ Pop Shop. Her mission is to embolden the workforce of the future. Nancy was born and raised in Honolulu, Hawaii, and currently lives in Vancouver, Canada. She can be reached at Mom ’n’ Pop Shop and WorkFreely.

ROCHELLE DAVIDSON, CPCC, ACC, is Chief Embolden Officer at Rochelle Davidson Coaching Her purpose is to embolden and equip people and organizations to create their unique impact in the world. With a BA in Business from the University of British Columbia and a MA in Applied Behavioral Sciences from Bastyr University, she is at her best when partnering with leaders to create healthy employees and workplaces, to get results that really matter. Rochelle is a proud cancer survivor and this experience has further fuelled her mission to see people and organizations thrive, not merely survive. She supports her clients in creating environments where their people are inspired, connect to each other in meaningful ways, and use their strengths to contribute to something bigger than themselves and has worked with companies including lululemon athletica, Accenture and University of British Columbia. Rochelle is a certified professional coach, credentialed through International Coach Federation and Coaches Training Institute. Rochelle lives a life she loves in Vancouver, Canada. She can be reached on LinkedIn, at and at

Their new book, Work Freely: Love Your Job. Love Your Life. is available on,  Amazon and other fine booksellers on September 17, 2019.