The “But” of Leadership

Success is harder to handle than failure.

Yesterday, I reconnected with the Chief Security Officer at Microsoft, Michael Howard. I’m freakishly interested in leadership so I asked him about his own leadership journey. He said, “Things are going smoothly.”

I wondered how he was handling smooth sailing. He said, “We don’t want to get comfortable.”

“It’s good to have a battle, it gives you a goal.”
Mike Howard

The “but” of success:

“We’re doing great but we’re not there yet.” Mike said,

“Be proud of success, BUT…”

Too much “not there yet” and you discourage the team. Too much celebrating success and everyone thinks you’ve arrived.

Creating the but:

The two-sided challenge of leadership is dissatisfaction during success and honoring progress when you fall short.

Mike brought up the term, “paranoid.”

During a workshop in New York City, Jim Collins said, “Hi performing leaders are “paranoid performers.” They’re always asking, ‘What if,’ and then preparing for it. They think about and anticipate the day of ‘bad things.’”

Mike said, “We’re asking ourselves, ‘What haven’t we thought of?’”

Positive environments:

Positive work environments are never an accident. They’re created by leaders who think and act with positivity.

Constant “buts” discourage. “We did great, but there’s more to do.”

The function of success is not comfort but fire.

Give it a break. Bring up your “but” tomorrow.

Don’t let your “but” diminish your success.

If you’re always saying “but” after forward movement, you’re a dark cloud, dissatisfied downer. You’re a dripping faucet. You discourage. You don’t motivate.

Help everyone enjoy hard earned successes; enjoy them yourself.

Pick your “buts” carefully.


I’m not suggesting Mike is constantly saying, “but.” However, when things are going well successful leaders always think what’s next; they always press forward.

Connect with Mike on twitter: @MikeHowardMSG

See the Facebook conversation: Success can be more challenging than failure because ______.

How do you navigate the tension between celebrating success and the need to reach higher?