Optimism is your worst enemy

You need to quit being so optimistic.

You heard me right. Quit being optimistic about your new hires. Your estimates. Your new clients. Your upcoming projects. Your team’s ability to deliver on-time. What your boss thinks of you.

See, that optimism is working against you. It’s blinding you to reality. It’s like the devil sitting on your shoulder, telling you “Don’t worry about it, it will be all right.”

In short, it’s making you do stooooopid things.

Successful companies aren’t optimistic about this stuff. Instead, they are risk-adverse and realistic.

Don’t believe me? Here are some examples…
1. Google asks programming candidates to do many technical interviews, do multiple rounds of interviews with various people and checks professional references. Why? Because they know that bad hires can perform very well in a single interview. They are NOT optimistic about candidates; they are careful and verify everything the interviewee says.

2. Box.com doesn’t assume new hires will just “figure it out” or “get along with the team.” Instead, they assign mentors, have training classes, have an onboarding plan, are direct about skill gaps, and invest heavily in their people in the first 90 days.

3. Thoughtbot isn’t optimistic that new clients and projects will go well. Instead, they publish a playbook which clearly lays how they do (and don’t!) work. This isn’t a sales activity; it’s a risk-mitigation strategy to make sure new clients understand what’s expected of them.

They don’t do these things because they are big, have fancy MBAs or just have money and time to burn. Instead, they overcome optimism bias and hindsight bias by adding rigor to their processes to improve their odds of success. They use the maxim “trust but verify” because there is too much on the line to be naturally optimistic.

The result of all your optimism is that you get let down by your programmers who “just don’t get it.” Your projects get delivered late. Your estimates get overrun. You lose the respect of your boss or client.

And those can kill your career or business.

So, what should you do when you find yourself being undeservedly optimistic about something that has a risk?
1. Stop rushing into action. It may seem easier to get a decision out of the way quickly, but if that decision has a significant impact or is hard to reverse, you need to slow down.

2. Measure how hard it is to reverse course, or much is at stake. Hiring a new contractor or programmer, promoting a new tech lead, or taking on a new client have multi-month consequences at the minimum.

3. Ask the question “What can (or has) gone wrong in the past?” Reflecting honestly on the past, trying to overcome hindsight bias and see clearly, will show you where an optimistic strategy has failed you. It will help you remember into the scenarios that you’d like to forget but need to learn lessons from.

4. Try a risk-mitigation activity. Checking references, mentoring activities, pair-programming, contract-to-hire arrangements, training programs, re-estimating, weekly developer meetings and monthly client meetings are all examples of activities which reduce risks. Google the phrase “How to great companies do X” to see what smart companies are doing instead of simply being optimistic.

Let me leave you with this gem: Hope is not a strategy.