Winning Big

June 6, 2008

I had scheduled a meeting with David, our CEO, several times in the past weeks, but on Monday, after being stood up on all those occasions, I finally just walked in to his office and started talking, which worked out in an interesting way.

It turns out that many of the concerns that Walter had were echoes of David’s concerns. Also, as I thought, Walter had been under pressure to complete other tasks he had, so it was all a bit overwhelming to him.

The particular concerns he had are a topic for another post.

The interesting thing was that I got to explain, in my view, what was going on to David, and without prompting, David asked me if I wanted to take ownership of the project, which was one of my goals for the meeting anyway.

He asked me what the cost of the system would be, and how much time it would take. When I told him, he said, “Ken, I want you to win big on this, but I need to know that it will happen.” Then he asked me if I’d bet my paycheck on it — and he meant it.


Climb with Care and Confidence

To answer him, I looked him in the face and I told him I would, yes. Even though I know that nothing is certain, I also know that bosses prefer overconfident managers. Using that knowledge, I knew not to equivocate– “Well, sort of… I guess, if…”

I said, yes, I would. Given the choice between betting my paycheck on Slomo or AwesomeSoft, I choose to bet on AwesomeSoft.

In response, he gave me the responsibility for the project. What is the risk in telling him to fire me if the project doesn’t go as planned?

Let’s play a little game theory.

Take Responsibility Reject Responsibility
Project Fails I lose my job, and I get another one. I continue to suffer under the onerous burden of not having any infrastructure for my team.
Project Succeeds I “Win Big.” Nothing happens to me. I get the system I want, and I am in roughly the same political position.

Let’s explore what that matrix means

  • If I have utterly misstepped, and in my arrogance recommended a system and a vendor that are going to fail, I risk being fired. If that happens, I may not be able to find a job at my current salary level, but I will be able to find one at an acceptably high level, so the stakes are fairly low here.
  • If I do not take responsibility, the project will fail. The path that Walter is headed down is a dead end. He’s considering going with a scuzy, proprietary vendor to get mediocre software that will not fit the needs of all departments, and will not scale for the future. That means the scenario of my not taking responsibility for the project ends the same way every time: I still have my job, but it’s doomed. I will not have the tools to build a strong team, or to meet the regulatory requirements that the government has set for the software I’m tasked with building. If I let this project go by the wayside, I will lose my opportunity to become the technical leader at Ideal because I’ll be bogged down indefinitely.

So, what looked like a risky proposition — staking my career at Ideal on something that is uncertain — actually turns out to be the only reasonable alternative to beginning an active job search. If I didn’t take the risk, I’d be almost certain to fail at my job, that same way that taking the risk is almost sure to save it.


2 Responses to “Winning Big”

  1. JJAstor Says:

    It would have been interesting if you elaborated on the “win big” quadrant, and what that truly means so that your readers can assign a weight to that outcome.

    I never thought of the overconfidence issue that way, but it’s true. Even some of the best leaders I’ve worked with think this way. I guess the best scenario is to have calibrated confidence in your own decision making process, and overconfidence as a facade.

  2. Ken Says:

    You’re right, Win Big does seem vague. Someone carefully reading this whole blog might get the subtext, but it’s not clear at all. David and I have an understand that if I prove myself, I will be the CTO of Ideal. That, and options, will bring me closer to wealth and achieving my goals. Winning Big is a step toward that reality.

    I think you’re exactly right, though. Calibrate your real confidence, and put up a facade of calculated overconfidence.

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