Gaining Perspective: A Crash Course on Dealing With Your Boss from your Bosses

By Catherine Kent, ProInspire Intern

In August, ProInspire’s 2014 Spring Managing For Success cohort in Washington DC had their last workshop focused on managing in organizations. As part of the program’s focus on “managing up”, ProInspire brought together a panel of nonprofit CEOs to share advice for the Management Fellows. The panel included:

• Michael Hill, President & CEO, Youth for Understanding
• Jack McCarthy, President & CEO, AppleTree Institute
• Pandit Wright, President & CEO, Boys & Girls Clubs of Greater Washington

During the discussion, the CEOs shared what they wish they knew earlier in their careers, common issues managers face, and dealing with style differences. The following are some of the key lessons learned:

1. Be an employee that leadership can trust

A consensus among all three panelists was that the most valuable employees are those they can trust – they are reliable, accountable, and know when to bring issues to leadership.

2. “You are not delegating up, you are managing up.” – Jake McCarthy

A common challenge faced among managers is getting time with their bosses. The panel discussed how there are a lot of things the CEO is managing that are not visible to people. Leaders are constantly getting pulled in all different directions. The panelists said the most effective way to approach your boss is to be solution focused, take initiative and be judicious. Do not just come with a problem, but also propose potential solutions.

3. “Take ownership to deal with a situation instead of just reacting. You have choices.” – Pandit Wright.

A common mistake among managers is that they use frustration and say something that damages a relationship. Instead of reacting negatively to a situation, take ownership and make choices to deal with that situation. Additionally, understand that the work you are doing is pivotal, but you are also part of a bigger picture.

4.  “Do not try to change the individuals you manage, but recognize who is showing up and how they are doing so.” – Michael Hill

Everyone has different styles in handling situations. The best way to deal with the versatility of personality differences is to have good communication. You need to be explicit about your expectations and what success looks like. Additionally, you should not try to change the individuals you manage. Everybody has differences – set clear goals and build trust in the organization, so people can show up as their best.

5. “Encourage everyone that getting resources for your organization is everyone’s business.” – Jack McCarthy

Jack emphasized that it is common for people to complain that resources aren’t coming in, but they don’t have initiative to take action. It is important to make it clear that the business of acquiring more resources is the business of everyone. This will allow for more success for the organization, and for individuals to feel empowered that they contributed to the success.

6. “My managers are absolutely essential if we are going to succeed.” – Michael Hill

The panelists discussed how important managers are for them. Managers are able to pay attention to details that leadership doed not have time to focus on. There is a symbiotic relationship between managers and the leadership. Random acts of thoughtfulness and engagement will go a long way.

7. “Let’s not admire the problems.” Pandit Wright

When dealing with a tough decision, which normally tends to deal with staff, the panelists highlighted the importance of dealing with the problems versus “admiring” them. Leaders can spend alot of time looking at problems, but really need to focus on taking action.

8.  “I always advise that there are two types of people, organizational people and enterprising people. Really understand yourself.” – Jack McCarthy

Fellows asked the panel about knowing when you are ready to move up. The advice from the panelists was to know yourself well, what work you like to do, and know how you perceive things. It is also important to be surrounded by honest mentors who have walked the path before you.

The panel was very informative in helping Management Fellows understand perspectives from CEOs, and thinking about how to be more effective in their own roles.  Thank you to all the panelists for taking time to speak with us!