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Hiring Your Next Boss


Whether you are looking for a new role in your current organization or looking to move to a different company, you should make sure you are prepared to interview your future boss and organization to make sure it’s the right fit. There are few things in life that get under my skin more than bad leadership. Unfortunately, you will see in this article that this seems to be the norm, not the exception. Maybe if we all do a better job picking (and leaving) bad managers, they will all be fired (wishful thinking I know!).

The way in which you evaluate your next position, company, and especially your boss, will determine how happy you are in your new role and the future success you will have in your career trajectory. Carefully crafted questions and astute observations during the interview process can help shed light on what the workplace culture and leadership style of an organization will feel like, and ultimately, how successful you will be in your new role. Let’s dive into how you can hire your next boss, and what steps you’ll have to take to get there.

Why it’s important to evaluate your next boss

As you seek your next job opportunity, be sure to research your prospective future boss as much as your possible future role and company. Evaluating your next boss is important because finding the perfect fit can benefit you in several ways. There is a great saying: “People do not quit their company. They quit their boss.” You can choose the right industry, a great and growing company, and even have your dream role, but if you have the wrong boss, your life could be miserable. You are not alone if you would rather have a new boss than a pay increase—65 percent of employees share the same sentiment. There is no question that having the right manager will improve your quality of life.

Finding the ideal boss is also better for your professional growth, especially if you’re at the beginning of your managing career. A recent Deloitte study found that 87 percent of companies say they don’t do an excellent job developing leaders at all levels, probably because they haven’t figured out the “secret sauce” to developing managers. Having a boss that’s an ideal fit is better for the greater good because, as sad as it is, 75 percent of employees report that their boss is the worst and most stressful part of their job.

How to get started – look inside and out

Before you start boss (or job) hunting, set aside some time to assess what you want in your career – long term. Start by envisioning your career goals 10 or 20 years out and the quality of life you desire along the way. Then you should take a realistic look at your capabilities and your current needs for professional growth. Identify your skills and what gaps you need to fill to help you determine what skills your future boss should have to help you excel in your career. Ideally your boss will help you grow beyond your role, but you have to make sure they’re capable of doing so.

Start by writing a “job description” that outlines the skills and qualities you want your prospective boss to have. This will help you evaluate what you want in a boss, similar to how they assess what they want in an employee. Take a moment to reflect on past positions and how your experiences with previous employers may have shaped your current needs. Evaluate what gave you energy and motivation to do your job and what took your energy – what best-selling author Daniel Pink refers to as “intrinsic motivators.” Think about what you liked about your past bosses and what you disliked about them.

During the interview process, observe and evaluate the prospective boss’s interview style. Assess how she or he delivers feedback on your answers. Note whether the manager delivers formal reviews or informal check-ins for employees. Have they outlined clear key performance indicators (KPIs) for the role, and do they appreciate the value of 360 evaluations? Also, keep an eye out for red flags and characteristics of a bad boss during the interview, such as: inappropriate behavior, unnecessary inquiries, lack of interest or disengagement, signs of disorganization, an unwillingness to answer questions about pay, lack of transparency, inability to provide a roadmap for success, tardiness, and a sense of disconnect from employees, especially lower level staff. You should also ask them why they are not hiring someone that has worked for them in the past for this role.

Besides conducting a “deep dive” interview with your possible future boss, also spend time to really understand the culture of the company and evaluate what will make you happy there. If you’re a philanthropic person, you’ll want to confirm that your prospective company frequently gives back to the community and allows employees time off to volunteer. If you want to work remotely from time-to-time, you’ll want to make sure your future employer allows you to take time off to help others. You can find a slew of information on most companies online, via websites like LinkedIn and Glassdoor. Feel free to ask the managers about any bad reviews. You will be able to tell a lot about them from their answer. As a manager and leader, they should not only be aware and understanding of bad reviews, but learn from them.

Informational interviews are a highly effective way to get your foot in the door. Whether it is in-person over a cup of coffee or over the phone, informal interviews give you an opportunity to introduce yourself to the hiring manager and ask more questions before securing a formal interview. Informal meetings can also help you and your potential employer understand one another’s unique skillsets and added value. If there isn’t an open position for your dream job at the moment, an informational interview can help you stay top of mind for the next available position. A good hiring manager always “builds a bench” and knows who the next two or three people are in line for a job—you want to make sure you’re in the queue. I know this is basic, but also make sure to follow up with the person who interviewed you and thank them for taking the time to help you learn more about the job – email follow ups are fine, but a hand-written thank-you note will really make you stand out with your potential future boss. You can continue to stay in touch by sharing articles in the future about topic that are important to them.

When assessing your next employer, leave no rock unturned, and no conversation unexplored. Know what you’re signing up for beyond reviewing the offer letter. Thoroughly vetting your future employer is the best way to understand what success will look like, so that you, your next boss and the company you’re supporting can effectively chart a course for the future that sets you on the path to success.

You are the only one that controls your future!

Onward and upward!

Russell P. Reeder

Written by Russell P. Reeder

A veteran technologist and chief executive to software and cloud businesses with more than 25 years of experience, Russell P. Reeder is the president and CEO of OVH US, a global, hyper-scale cloud provider that offers businesses industry-leading performance and value. Reeder specializes in leading high-growth, disruptive businesses that marry a customer-centric vision and strong technology innovation -- ranging from his enterprise software experience at Oracle to ebooks, IPTV, and web hosting. His breadth of experience, including sales and branding, enables Reeder to build teams that execute market-impacting business plans, consistently generating value for customers and shareholders. Throughout his career, Reeder has tried to constantly improve his leadership philosophy, which is directly inspired by his family as well as his own experiences as a dad, a triathlete and a human being trying to be a better person and help others live happier, more productive lives.

Read more posts by Russell P. Reeder

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