Brad Brooks | Crain's

In this ongoing series, we ask executives, entrepreneurs and business leaders about mistakes that have shaped their business philosophy.

Brad Brooks

Background:  

DocuSign is a company that allows users to securely sign and manage documents online. 

The Mistake:

I was hired at AT&T — before it went through the divestitures — to help them with some issues they were having on the border with Mexico, losing massive amounts of money. They suspected business there was less efficient than other key competitors — Nortel, at the time. I was hired in New Jersey and the first thing I do is get on a plane to Texas. Because of my background, I figured out a lot of things they were doing wrong — overreporting costs, getting overcharged on import duties, a number of things. I explained my findings to the trade lawyers with AT&T after I had been there a few weeks.

Being very risk-averse, they said, "We've got to disclose everything. We've got to tell the government everything that's going on, talk about all our past sins, all the different things that we've done." I was in my mid-20s. This company with 300,000 employees had an old-school, East Coast culture. I knew [their solution] was wrong. But, being young, I said, “All right. Go ahead and disclose it."

So we went into the U.S. Customs service office in Texas. We started to disclose that we had found some discrepancies in our business practices on the border for at least three years. They picked up the phone as the conversation was going on and within 10 minutes, two special agents walked in and laid down a target letter — a notification that there is now a criminal investigation. At that point, the government can and will hold you liable for any type of disclosure of information.

[We should have gone] in there later and said, "We did something wrong. Here's what really happened. Here is how we are resolving the issue, here is how we think we should handle it going forward." Instead — without a plan — we were telling the law enforcement agency we might have done something wrong.

I knew it was the wrong approach, but I believed I didn’t have a voice because I was a junior person that was new to the role. All I could think was, "I'm fired. This is it."

Back in New Jersey, the senior vice president calls me into his office. He says, “Brad, you know why you are in this office?"

And I said, "Yeah, I think I've got a feeling why I am in this office."

And he said, "Guess what? I'm not going to fire you. I can't believe what went on down at the border. It sounds like we've got a real problem. We've got to figure it out as a company."

I said, "Yep. That's true."

And he said, “But, Brad, you had a different point of view on what should be done … but you didn’t make it known."

I said, "But I'm the low guy on the totem pole."

He said, "I don’t care what level you are … I specifically signed off on you going in there and doing this job. That means, you are the one in charge. … You’ve got to figure out what your voice is. Your leadership voice. And when these things rise, let me tell you how you are going to succeed in your career … by speaking up and being convicted and being passionate about your point of view. You get the one pass going forward. But I expect you to be a different leader as you progress in your career with this company."

I constantly push people to have and express conflict.

The Lesson:

I've never had an issue speaking truth to authority since that time. And it has probably been the single biggest differentiator in my career. I constantly push people to have and express conflict; [to] be able to contribute at any level. 

I thought I had poisoned my career right out of grad school. ... Things eventually worked out well. About nine months later, [the government] wrote us a check for more than $5 million. We transformed the operations.

Follow Brad Brooks on Twitter at @BradLBrooks.