21 Tips for Leading and Managing

  1. Delegate projects, not tasks.
  2. Let go. Check in. Ask questions. If you don’t get the right answers, ask more questions. Offer help. If you do this gently, it’s not micromanagement.
  3. Administrative work is part of every job; you can’t delegate it all. It’s better to work alongside your team to get it done than to hand it off.
  4. People grow by taking ownership of increasingly big things. Your most important job as a leader is to facilitate that.
  5. Expect and encourage people to claim things. Let them choose what to claim.
  6. Have high standards, but hold them lightly.
  7. People watch what you do more than they listen to what you say.
  8. The big picture is probably obvious to you, but the story of your team bears constant telling. Why are we here? What are we doing together? Where are we going? Why does it matter?
  9. Be vulnerable. Let folks see what you’re struggling with. Don’t put up a false front of hyper-competence; nobody believes it anyway.
  10. Get excited about things. Bring people crazy ideas every once in a while so they’ll feel comfortable bringing theirs to you.

    Photo by Eugene Kim
  11. Cultivate ambient awareness – up, down and sideways.
  12. Budgets are stories about values. Make sure everyone knows how to read them.
  13. Deliver information updates as efficiently as possible, usually in writing; defend face time for questions, discussion and generative work.
  14. Eat lunch with your team as often as you can.
  15. Have opinions, but be willing to change them.
  16. With every hire, you should raise the average quality of your team.
  17. Your gut is probably right. Have the courage to listen.
  18. Do not act when triggered.
  19. Keep track of your commitments and follow through flawlessly or renegotiate proactively.
  20. Avoid self-inflicted fire drills. The world gives us enough real ones.
  21. It is OK to create some discomfort to drive change. Construct and regulate it carefully.

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Three dimensions of transformational leadership

I’ve been thinking a lot about what makes truly effective leaders in the social change sector. There are people who’ve devoted their entire careers to the question, and I don’t presume to their erudition. But lately, I’ve been reflecting on three key dimensions of organzational leadership that have really helped me understand organizations I’ve been involved with over the years.

External relations leadership

External relations is the classic, outward-facing dimension of leadership. It’s the one we often mistake for the whole ball of wax. External relations is about charisma, storytelling and selling the organization to the world at large. It’s a vitally important dimension of leadership, especially in the nonprofit sector, where donors and grantmakers often give based on emotion and relationships. Many nonprofits are founded by leaders who are strong on this dimension of leadership.

Management leadership

This is the internal-facing “make the trains run on time” function. Management leadership is what builds systems and processes; it allows organizations to execute consistently, with excellence and at scale. Few organizations can grow or be successful over the long term without developing strong management leadership. Leaders who are strong at management are often very different personalities than those who excel at external relations–they tend to be more introverted and detail-oriented. Many management oriented leaders are found in COO roles.

In many nonprofits, the top two people are a strong external relations leader and a strong management leader. This can be a pretty effective leadership model for some organizations, and is far preferable to a single CEO trying to perform both roles.

But if we stop with just these two leadership functions, we overlook something critical to the long term health and success of an organization: the leadership function that is focused on taking care of its people.

Nurturant leadership

Leadership is not just about strategy, sales and management, leadership is motivating and supporting people so they thrive and excel. It’s great to have a charismatic leader out front, and a management leader who can build and refine the internal processes. But someone has to be focused on taking care of the organization’s people as whole human beings. This is not an “HR” function; it’s a core leadership function.

Nurturant leadership is this dimension of leadership–and, unfortunately, it’s often overlooked–and consequently one of the biggest barriers to long-term organizational excellence.

Lots of organizations have a strong ED/COO combination providing external relations and management leadership. But these organizations sometimes have a tough time retaining talented staff over the long haul, because they are missing third leg of the leadership stool: a strong nurturant leader.

“But isn’t this the CEO’s job?” you ask. Well, it’s certainly the CEO’s responsibility to make sure the organization has sufficient nurturant leadership. But many CEOs struggle with this leadership function–particularly CEOs who are focused on external relations. External relations leaders are charismatic and visionary, but they are often ineffective at nurturant leadership for several reasons:

  1. Being outward-oriented means you’re out of the office lot. There are so many meetings to go to, donors and clients to pitch, speeches to give. External relations leaders are often on the road so much and in so many meetings with stakeholders that they don’t have the focused time it takes to nurture their teams.
  2. The more visionary and charismatic the leader, the more intimidating they often are. It’s hard to nurture people who are a little bit scared of you.
  3. A certain degree of narcissism often goes with the territory, and while it’s not unhealthy per se, it does tend to interfere with the empathetic demands of nurturant leadership.

Similarly, many management leaders struggle with this as well. When you are focused on building systems and processes, it is easy to slip over the line into caring more about “the system” than the people that must operate within it. Overall, though, I’ve seen a lot more people who are successful management/nurturant leaders than people who combine external relations and nurturant leadership.

The biggest lesson for organizations, though, is to explicitly attend to and elevate nurturant leadership as a discipline co-equal to external relations and management leadership. More on this in a future blog post.

Failures in Generalship and the Nonprofit Sector

The thing I am loving most about grad school so far is that it is exposing me to bodies of literature that my former life as a nonprofit sector consultant just didn’t.  (Whether it could have, that’s another story.)  Today, I read Lt. Col. Paul Yingling’s article “A Failure in Generalship,” which resonated for me in unexpected ways.

Yingling’s brief article is a tough look at the reasons why America’s military leaders failed in almost identical ways in both Vietnam and Iraq, despite the nearly thirty years they had to learn and adapt.  He concludes that the reasons are not about individual personalities, but in the systemic ways that we select our generals, and the ways those systems fail to produce generals that are capable of succeeding at important aspects of their jobs.

Here’s a long excerpt that you should read closely.  I’m blown away by how much this analysis is directly relevant to the failures of leadership in social change movements.  I’ve boldfaced some of the best bits.  Hint: every place he writes “generals” you can sub in “social change leaders” and every place he says “war” you can think “social change.”

I wish that the social change sector had the courage to examine itself so honestly and to ask tough systems questions like this.  Of course, it is also true that we lack the systems of accountability that are at least theoretically provided by Congress, so it may be that our challenge is even harder than the military’s.  Food for thought.

The Generals We Need

The most insightful examination of failed generalship comes from J.F.C. Fuller’s “Generalship: Its Diseases and Their Cure.”…  He found three common characteristics in great generals — courage, creative intelligence and physical fitness.

The need for intelligent, creative and courageous general officers is self-evident. An understanding of the larger aspects of war is essential to great generalship. However, a survey of Army three- and four-star generals shows that only 25 percent hold advanced degrees from civilian institutions in the social sciences or humanities. Counterinsurgency theory holds that proficiency in foreign languages is essential to success, yet only one in four of the Army’s senior generals speaks another language. While the physical courage of America’s generals is not in doubt, there is less certainty regarding their moral courage. In almost surreal language, professional military men blame their recent lack of candor on the intimidating management style of their civilian masters. Now that the public is immediately concerned with the crisis in Iraq, some of our generals are finding their voices. They may have waited too long.

Neither the executive branch nor the services themselves are likely to remedy the shortcomings in America’s general officer corps. Indeed, the tendency of the executive branch to seek out mild-mannered team players to serve as senior generals is part of the problem. The services themselves are equally to blame. The system that produces our generals does little to reward creativity and moral courage. Officers rise to flag rank by following remarkably similar career patterns. Senior generals, both active and retired, are the most important figures in determining an officer’s potential for flag rank. The views of subordinates and peers play no role in an officer’s advancement; to move up he must only please his superiors. In a system in which senior officers select for promotion those like themselves, there are powerful incentives for conformity. It is unreasonable to expect that an officer who spends 25 years conforming to institutional expectations will emerge as an innovator in his late forties.

If America desires creative intelligence and moral courage in its general officer corps, it must create a system that rewards these qualities. Congress can create such incentives by exercising its proper oversight function in three areas. First, Congress must change the system for selecting general officers. Second, oversight committees must apply increased scrutiny over generating the necessary means and pursuing appropriate ways for applying America’s military power. Third, the Senate must hold accountable through its confirmation powers those officers who fail to achieve the aims of policy at an acceptable cost in blood and treasure.

To improve the creative intelligence of our generals, Congress must change the officer promotion system in ways that reward adaptation and intellectual achievement. Congress should require the armed services to implement 360-degree evaluations for field-grade and flag officers. Junior officers and noncommissioned officers are often the first to adapt because they bear the brunt of failed tactics most directly. They are also less wed to organizational norms and less influenced by organizational taboos. Junior leaders have valuable insights regarding the effectiveness of their leaders, but the current promotion system excludes these judgments. Incorporating subordinate and peer reviews into promotion decisions for senior leaders would produce officers more willing to adapt to changing circumstances, and less likely to conform to outmoded practices.

Congress should also modify the officer promotion system in ways that reward intellectual achievement. The Senate should examine the education and professional writing of nominees for three- and four-star billets as part of the confirmation process. The Senate would never confirm to the Supreme Court a nominee who had neither been to law school nor written legal opinions. However, it routinely confirms four-star generals who possess neither graduate education in the social sciences or humanities nor the capability to speak a foreign language. Senior general officers must have a vision of what future conflicts will look like and what capabilities the U.S. requires to prevail in those conflicts. They must possess the capability to understand and interact with foreign cultures. A solid record of intellectual achievement and fluency in foreign languages are effective indicators of an officer’s potential for senior leadership.

To reward moral courage in our general officers, Congress must ask hard questions about the means and ways for war as part of its oversight responsibility. Some of the answers will be shocking, which is perhaps why Congress has not asked and the generals have not told. Congress must ask for a candid assessment of the money and manpower required over the next generation to prevail in the Long War. The money required to prevail may place fiscal constraints on popular domestic priorities. The quantity and quality of manpower required may call into question the viability of the all-volunteer military. Congress must re-examine the allocation of existing resources, and demand that procurement priorities reflect the most likely threats we will face. Congress must be equally rigorous in ensuring that the ways of war contribute to conflict termination consistent with the aims of national policy. If our operations produce more enemies than they defeat, no amount of force is sufficient to prevail. Current oversight efforts have proved inadequate, allowing the executive branch, the services and lobbyists to present information that is sometimes incomplete, inaccurate or self-serving. Exercising adequate oversight will require members of Congress to develop the expertise necessary to ask the right questions and display the courage to follow the truth wherever it leads them.

Finally, Congress must enhance accountability by exercising its little-used authority to confirm the retired rank of general officers. By law, Congress must confirm an officer who retires at three- or four-star rank. In the past this requirement has been pro forma in all but a few cases. A general who presides over a massive human rights scandal or a substantial deterioration in security ought to be retired at a lower rank than one who serves with distinction. A general who fails to provide Congress with an accurate and candid assessment of strategic probabilities ought to suffer the same penalty. As matters stand now, a private who loses a rifle suffers far greater consequences than a general who loses a war. By exercising its powers to confirm the retired ranks of general officers, Congress can restore accountability among senior military leaders.