What I learned as a 20-something executive in a startup

Being a mentor is challenging. It requires time, energy, and dedication. Not everybody is cut out for the gig. But here’s what no one told me: being a mentee is also challenging. Not everyone’s cut out for the role either.

Being a good mentee requires you to listen, watch, and learn even without always knowing why. That’s where patience and trust come in – attributes that don’t always come easily to young, ambitious people.

Let me give you an example.

When I was in my mid-20s, I joined a startup called SeeUthere, which went on to become Active Network’s StarCite. I was one of the three engineering managers in the company.

As with most startups, we experienced a lot of turmoil in the early days, and within a few months of joining the company, we lost a few co-founders. In the ensuing chaos, the surviving co-founder, John Chang, tapped me to run the engineering department.

I didn’t think I was ready. This was before Facebook was built and it was still uncommon for companies to have 20-something executives. Luckily, John didn’t ask me if I thought I was ready; he only asked what I would do to fix the mess.

Suddenly, I was an “executive,” expected to not only run my department but also contribute to the overall strategy of the company.

I distinctly remember one meeting, where the head of marketing was talking about lead generation. I was thinking, “What do I know about lead generation?” I knew code. I knew how to build things. But lead generation? Nada.

The marketing director had an MBA from Stanford. So did John. In fact, at one point, I was the only executive who didn’t have a Stanford MBA (or any MBA for that matter).

John didn’t ask me if I thought I was ready; he only asked what I would do to fix the mess.

Why did John even ask me to join that meeting? It wasn’t that I was bored, I just felt out of place and a little bit intimidated because there was pretty much nothing I could add to the conversation.

Wasn’t I wasting their time? Was I wasting mine? I had code to ship!

I felt bad – maybe even guilty. All that ran silently through my head. But because John had invited me, I sat and listened to the discussion. I paid close attention and I did my best to follow along.

I didn’t know it at the time, but there was a reason I was there.

First major crisis

John always had reasons. I just didn’t always understand them. I even wondered about his nightly calls to his team members.

Despite his insane hours, he would call each of us on his commute home. A whip-smart entrepreneur, he always knew the inner workings of his company, but he also wanted each of his executives to know them as well. He wanted to keep us in the loop.

Again, I didn’t quite understand why he was spending time with me – the head of engineering – discussing our pricing strategy or explaining our plan for beefing up account management. I didn’t have any sales experience.

It wasn’t until a few years later when, still head of engineering, I had the first major crisis of my career.

It was 2004. The company was growing again after the dotcom nuclear winter. Vowing to never have a bloated cost structure again, we decided that our company should outsource some of our engineering work. I analyzed the business case, interviewed vendors, did reference checks, and presented my recommendations to the executive team. It was a go – we decided to outsource some work to China.

Unfortunately, the decision turned out to be disastrous. The idea of putting a team in China was spot on, but we should have built our own team there instead of outsourcing the key parts of our products. The mistake easily cost the company a year of momentum – momentum that a startup like ours could not afford to lose.

There was a reason…

I led engineering, so I knew the buck stopped with me. I went into John’s office and told him that I had committed an impeachable offense, offering to resign.

John said no.

I was baffled, but relieved. I was also anxious. Even though I had John’s backing, I worried about how the rest of the company would react. Would they turn on me? Would this tear us apart?

My decision had impacted the entire company: sales couldn’t sell, marketing plans were put on hold, support was swamped. They had every reason to take it out on me.

But they didn’t. They supported me and we stuck together. I was too busy with work to think about how we were able to make it through.

But later, with the benefit of hindsight, it dawned on me. We survived because of John. He created a team. He brought us together. There was a reason we all sat together in those executive meetings. There was a reason he made all those calls on his way home.

He was creating an environment that would allow the company to survive adversity.

Even though I led engineering, we made the decisions together. No single person was to blame.

I was able to move on and more importantly, the company was able to move on – precisely because no one was throwing around blame. There were no whisper campaigns or secret meetings. We were in it together.

That’s saying a lot. So many startups fail not from a strategic error, but from the infighting that follows.

Honestly, it didn’t matter that I didn’t understand John’s magic at the time. But it did matter that I listened and learned.

Watch and learn

The lesson for those wanting to be mentored is this: you won’t always know why the person who is mentoring you does the things he or she does. In fact, you will probably be bewildered most of the time, just as I was.

But if you’ve chosen a good mentor, have a little faith. Actually, have a lot of faith.

So many startups fail not from a strategic error, but from the infighting that follows.

Your mentor will do things you don’t understand. He or she will have good reasons, but you probably won’t know those reasons until later.

That’s also why you should stick with your mentor as long as you can. You want to be there through the good times as well as the hard times. Anyone can manage during good times, but it takes a lot of finesse, smarts, and experience to do so in tough times.

How does your mentor handle adversity? Watch carefully and you’ll learn, just like I did.

So when your mentor suggests that you to go to a meeting, go. When he calls and tells you information you don’t think you need to know, listen.

Trust me, it will pay off.

This article was first published on Monk’s Hill Ventures.