In The Ring: Problems, Problems Everywhere

Seth Sternberg is the CEO and Co-founder of Meebo. He writes this guest column, In The Ring, from a CEO’s perspective.

When you decide you’re going to start, or run, a startup, you’re signing up for problems. Lots of problems. They’re everywhere. New competitors. A key employee leaving. You didn’t hit your numbers. A market shift rendering your service useless in a year or two.

When you first start, they’re almost fun. “Oh, how am I gonna solve that one?” Or better yet, “All these VCs want to get into my deal!” Of course, they also have the tendency to seem existential. You don’t have much at the beginning, so the good feels like it can make you—“We just landed an awesome partnership. We just became millionaires!”—and the bad feels like it can destroy you—“Holy shit, Facebook’s launching what?? We’re dead.”

As you scale, more problems seem to crop up—hourly. A system that was working super well, like how your engineers choose projects, may all of the sudden break once you tip past 12 engineers. Who knew it’d happen then? It did, and it felt like it happened out of the blue. Before you know it, your engineers are feeling unmotivated, the system seems broken, and it’s no longer fun

For the CEO, this can get overwhelming fast. If you have a great team, most problems get solved before you ever hear about them. But there are enough big problems that you will hear about, at least one a day. And it’s not the easy problems that make it your way. Those already got solved. Rather, they’re the hardest problems that people bring to your attention. Day after day. That, my friends, can be tiring.

Have you caught the setup yet? The huge, massive, you could lose your job kind of risk lurking in this story yet? It’s all too easy to become the CEO who telegraphs “don’t bring me every damn problem—you’re smart—solve your own problems. That’s why I hired you!” This, in fact, can seem particularly effective. Adopt this position and problems will apparently take care of themselves…until all those lurking problems that never made it to you, for fear of you not wanting to hear them, result in a declining company. Buh-bye.

So what to do? First, obviously, resist the temptation to become that CEO who no one wants to tell what’s really going on. Just don’t be that guy or gal. That means you need to listen to the problems that come your way and, as much as you can, play traffic director. Help them figure out who to work with to solve their problems. It’s incredibly empowering if you can help others learn how to solve their problems, rather than solving the problems for them.

Second, it’s all about education. You need to teach people how to identify and solve problems when they’re nascent, rather than letting them fester and become a big deal. Catching problems early (eg: our system for deciding what engineers work on broke) often keeps larger problems from ever occurring (eg: our star engineer wants to leave). Teaching this, it turns out, is surprisingly complex

Once I began to realize that I needed to actively talk to the folks at Meebo about identifying and solving problems, I thought it would clearly be enough to say, “Guys, don’t let problems fester. If you notice a problem, fix it or bring it to someone who can!” It wasn’t—somehow problems still festered without being solved. So I began to telegraph the process of solving a problem.

1. Identify that a problem exists.

2. Identify the cause of the problem.

3. Hypothesize a solution.

4. Implement the solution.

Thinking about problems in a structured way, such as this, turned out to help my own thinking on problem solving. In fact, it led to two pretty interesting discoveries: a) people often don’t realize they’re facing a problem. Rather, they just feel frustration. b) problem solving, and particularly the ability to shepherd a problem through the four stages listed above, is highly correlated with seniority.

It turns out that many folks, particularly junior folks, don’t realize when they’ve run into a solvable problem. Rather, they’ll tend to just feel frustration. I’ve had this same thing happen to me. You know that feeling you get in your gut when something doesn’t feel right? It bums you out, but you can’t quite put your finger on it. That’s it. There’s a problem, but you haven’t yet consciously realized it. Thus, junior folks are particularly susceptible to becoming frustrated, confiding in their peers about their frustration, and not beginning the process of solving the problem. You tend to see it manifest in the form of complaints, rants, and general lack of motivation. Things then snowball.

This is where education comes in. Teaching folks to realize they’re frustrated and that that’s a sign they need to think about why they’re frustrated is the first step in ensuring that problems get caught and solved early. As long as the problem gets identified (step 1), if that person can’t get to step 2 on their own, at least they can bring it to someone who can.

I’m not certain why seniority and problem solving capability are correlated. It’s tempting to chalk it up to experience, but it’s more likely information or influence asymmetry—more senior folks are more likely to know who can help them solve a problem, where the cause may be coming from within the organization, and certainly are more likely to have the influence to help implement a solution. That is, it’s likely less tied to experience and more tied to information flow, which is often tied to place within a given hierarchy. This is why information transparency within an organization is so crucial (topic for a future post). But knowing this relationship exists can help you both empower your more junior folks, and ensure that your more senior folks understand how important it is to help the folks they manage identify and solve problems with them before they mushroom.

The other half of this is, once the problem is identified, being transparent about solving the problem. It’s an equal partnership between you and your employees. It’s too easy to disappear into the management black box, secure in the knowledge that you’re working to solve the problem, but leaving everyone else hanging. To instill a sense of trust and empowerment, establishing a pattern of good, collaborative problem solving can be the difference between a motivated team working with you to solve problems and a dysfunctional organization.

Net: don’t run from your problems, but do everything you can to empower your people to solve them early and often.

Seth Sternberg
Meebo, IBM, SpeakerText

Seth Sternberg co-founded Meebo. Seth, a Connecticut native, worked in IBM’s mergers and acquisitions department, while also working on corporate strategy and venture capital initiatives prior to starting Meebo.

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Launch Date:
January 2, 2005

Meebo is a social platform connecting users with their friends across the web. It began in 2005 as a browser based instant messaging program which supported multiple IM services, including Yahoo! Messenger, Windows Live Messenger, AIM, ICQ, MySpaceIM, Facebook Chat, Google Talk and others.

Meebo expanded its offering with the introduction of Meebo Rooms, and most significantly, the Meebo Bar. The Meebo bar allows users to connect with their friends and share content on hundreds of content sites across the…

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