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How to Endear Yourself to Your Boss

Get assignments in early, clearly and concisely.

Growing your leadership skills includes learning how to support the leaders you work with. Dr. Ellen-Earle Chaffee gave tips on serving your boss in the closing keynote at the ACE/OWHE Summit for Women Presidents in Milwaukee in June.

She’s just retired as president of Valley City State University in North Dakota, which she led from 1993 to the end of June 2008. For most of that time (1993-2002) she was president of Mayville State University ND as well. She spearheaded the technology drive to make them both laptop communities, giving all faculty and students notebook computers and Internet access since 1996.

“I’m pulling out of a passionate and deep love affair. My only role is to help the new president, however he wants me to,” she said of her retirement. Giving back is a great way to pull out.

For women at earlier career stages who hope to rise in leadership, helping the president or other leaders is part of their job. It’s also a way to win notice, mentoring, plum assignments and nominations to leadership development programs.

It will help you learn to deal with both/and, as top administrators must. You need both a long-term and an immediate horizon, with attention to global trends and what’s happening close at hand. You have to communicate with impact to many different audiences. You need a broad span of interest and attention for both the abstract and the concrete.

Key leadership imperatives include:

  • Purpose—balancing both pride and change
  • Optimism—balancing both hope and realism
  • Communication—balancing talking and listening
  • Relationships—balancing people, tasks and ideas

Here’s how you can help your leader perform these balancing acts, and learn along the way.

Read her mind

“I’m not an open book,” Chaffee said. Reading your leader’s mind requires a new kind of perception. Seek out themes, clues, concerns and priorities in her meeting and conference agendas, the organizations she joins and her events, speeches and campaigns.

Getting inside her head helps you catch on faster, ask better questions, see connections and make wiser suggestions.

Understand her agendas Know what balancing acts your leader is dealing with and what dangerous waters she must navigate. Understand her strategic plan and the forces that drive her personally.

This will guide you to:

  • Synchronize your work priorities/timetable with hers.
  • Notice gaps and ways to remedy them.
  • Recognize key constituents; help her connect with them.
  • Surprise her pleasantly by identifying what might help.

Translate to different audiences

What worries or confuses her constituents? Understanding this can help you stay tuned to what people are really thinking.

Once you grasp what each audience needs, find ways to communicate in terms they’ll understand. Address rumors, misinformation and audience concerns. Sort out problems and solutions. Depending on the issue and the audience, you can help them make sense of developments, sort out cause and effect and grasp the implications.

 Understand the politics

Politics is the fine art of getting things done in communities of humans, each with her own agenda and priorities. Disdain it at your peril.

To promote your leader’s agenda and help her look good, consider:

  • Who needs input on a plan or decision?
  • Who needs to be recognized?
  • Who will oppose or resist? Why?
  • Who will help? Who stands to gain?
  • Who else needs to know?

Understanding politics will help you keep your leader out of the tar pit and guard against “death by insult.”

Import or invent solutions

“Never bring me a problem without some suggested solutions,” Chaffee said. No need to reinvent the wheel; find out what others are doing in similar problems. Would their solutions work here? How would they need tweaking?

Bringing a proposed solution along with the problem cuts to the chase and speeds the process. Note alternatives and be prepared to validate them or weed them out. The best thing you can bring to your leader is a proposal that she can endorse and then forget.

Make it quick

For presidents and many others in upper administration, work is 24/7. They’re constantly shifting focus. “You don’t have to be schizophrenic to do this job, but it helps!” Chaffee quipped.

Get assignments in early, clearly and concisely. “If it doesn’t fit on your hand, it’s too long,” she said. Start with a brief reorientation, setting the stage; your leader has had other concerns since she gave you the assignment. Be sure to include the “why” or “so what”—in brief, why this is worth even a minute of her time.

Do it before she needs it

Count on her to count on you; anticipate her needs. Proactively offer to be “the other person”—the source of information for upcoming presentations or controversies. For any key messages that come up again and again, give her 100 ways to make the point.

“The future is not some place we are going, but one we are creating. The paths to it are not found but made,” Chaffee quoted from political theorist Dr. John Schaar of the University of California, Santa Cruz. She is living her immediate future as the 2008–09 president-in-residence at the Harvard University’s Graduate School of Education.


Cook, Sarah Gibbard, Ph.D. (2008, October). How to endear yourself to your boss. Women in Higher Education, 17(10), p. 8.

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