Dear President Obama: Sir, Please Don't Screw It Up

Dear Mr. President:

A year ago I (with my colleague John Larrere) wrote a piece for this Web site offering suggestions for how you should approach your new job. Like most pundits, I offered advice without really understanding your role or the challenges you face.

I knew better. As someone who counsels business leaders, I learned long ago that before I can provide insight, I need context: I have to understand the person, the role, the situation. In your case, that's difficult. All I really know is what I see in the media, which are growing more shrill, shallow, and suspect by the day.

So when asked to take a look back on your first year, I hesitated, not wanting to repeat my mistake. But then I realized that with a fourth of your term already gone, you have very little time left to refine your approach and achieve your goals. And, if your party's stunning Senate loss in Massachusetts Tuesday is any indication, the road forward is only going to become more challenging. So I thought it might be useful to reflect—apolitically—on where you are and where you're going. But as I do with new clients I coach, instead of giving advice, I want to proffer a few questions for you to ponder as you take our nation forward:

1. Have you gotten your head around the role of the Presidency?

You may be a smart, successful, confident, experienced leader, but nothing can really prepare you for the job of President of the United States. A year into it, how have your perceptions of the role and yourself changed? (I'd love to know who you see when you look into the mirror each morning.) I hope you've come to terms emotionally and intellectually with the incredibly powerful position you hold, but if you're struggling with that, don't feel bad. It's a major challenge every new CEO or enterprise leader with a modicum of emotional intelligence struggles with. No matter how confident, few feel they are ready for such a role, and many often wonder if they are doing the best they can.

2. How's your senior team working out?

You've put together a team of bright, hard-working leaders. As part of the group who planned your leadership retreat last summer, I was pleasantly surprised how well they appeared to work together—an earnest, engaged, seemingly ego-free group. But how well are they really working together to drive your agenda? Are they all on board? Are they collaborating? As a team, are they taking accountability?

Frankly, they didn't appear too eager to step forward and share responsibility for dropping the ball after the Christmas Day attempted terrorist attack. Is it time you changed the lineup a bit or held them accountable to a higher standard? Many new CEOs don't spend enough time really building and shaping their teams. Nor are they decisive in making changes. I know these folks are your friends, confidants, and supporters who helped get you where you are. But if they're screwing up, they need to go—and sooner rather than later.

3. Are you delegating effectively or are you still doing too much yourself?

Early on, the rap on you was that you were personally involved in too many things, like running all over the world instead of letting Secretary of State Clinton do what you appointed her to do. That seems to have improved. But I worry. You're a high achiever who likes things done right. Leaders like you often get sucked into the details and micro-tactics. Be careful. It's an inviting but dangerous trap that leaves little time for truly leading and focusing on what's critical.

4. How well is your organization executing on your agenda?

I'm not talking about your Cabinet or staff, but those professionals who do the day-to-day work of running our government. Elected officials alone do not make good government. The best policy, Democratic or Republican, will fail if it isn't executed effectively. We've seen it time and again from FEMA's blunders in the aftermath of Hurricane Katrina to the botched situation that allowed would-be bomber Umar Farouk Abdulmutallab to board a plane for the U.S.

As in the private sector, the key to success for any strategy is implementation, which requires effective accountability and collaboration, not just at the top but throughout the organization. Are you focusing enough effort on creating such a culture within our civil service?

5. Are you getting the feedback you need?

Most leaders at your level don't. The higher leaders rise in organizations, the less feedback they receive and the bigger the gap between how they see themselves and how others see them. It's not only lonely at the top, it can also be very surreal, especially if most of your feedback comes only from pandering supporters and obstinate opponents. You need to make sure you continue to challenge your current advisers, while at the same time seeking fresh perspectives. And remember, in your position you have to ask for feedback. Otherwise you will not get it.

6. Are you being assertive enough?

Your critics say no. Personally I don't know, although you do seem to take your time in making decisions. What I do know is that too many senior leaders assume that those around them have the smarts and sense to do what's right, and that as the top dog they shouldn't have to be directive or coercive. Not so. Don't be afraid to bring the hammer down fast and hard. You won't regret it.

7. What's your vision?

Or should I ask, where's your vision? Your game was really on a year ago. It got you to the Big Show. But you seem to be losing it. I know you have a lot on your plate, what with the economy, the war on terrorism, and health care. But, like any good executive, if you're going to be successful you and your team have to keep the vision top-of-mind and continually refine and articulate it.

8. Are you effectively connecting with all your constituencies, especially those of us in the middle?

Given the Massachusetts upset, I'd say probably not. One of the big problems top business leaders face is the multitude of constituencies they must deal with. Too often they try to either be all things to all people or, in order to appease one, ignore another. Given the insular nature of Washington and the variety of voices crying for their piece of the action—from the plethora of special interests to the chorus of political and policy critics—I'm concerned that you may be falling into a similar trap. I especially worry that those of us in the middle—the less vocal majority—will be overlooked and excluded from the debate.

9. Are you being transparent and honest—both with yourself and your constituencies?

My gut tells me you are. (Personally I find it refreshing when you admit a mistake or cut through the BS and get to the point, like when you called Kanye West a jackass.) But my gut's not that accurate, especially after Mark McGwire and Tiger Woods. Please don't disappoint us like the past two Presidents, one who appeared blissfully amoral, the other blindly arrogant. A lack of honesty and forthrightness in both the public and private sectors helped dig the economic hole we're now trying to climb out of. Unless we regain much-needed trust both in business and politics we'll be hard-pressed to regain our position in the world. So please, sir, don't screw it up.

10. What are you doing to have fun?

George W. played rancher and rode his bike. We all know what Bill Clinton did. How about you? What are you doing to relax? We hear about the hoop games. We see you on the golf course, with the family, going to Broadway. But are you really relaxing? Are you doing those little things that are not part of the job, but that give you intrinsic satisfaction and fulfillment? All good executives, no matter how hard-working, need a bit of balance in their lives. Face it, all work and no play makes even Barack a dull and cranky boy.

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