I thought Rand Fishkin’s recent blog post on “Cynical Optimism” was a nice read. He talks about how while there are plenty of things to be cynical about when it comes to humanity and our tedencies towards negative things, there is plenty to be optimistic about with regards to our progress as a whole. The phrase “Cynical Optimism” is one that I really like to use when describing how to attack business plans, budgets, technical roadmaps, or other kinds of planning.
First, Be Optimistic
When setting goals, you definitely want to be an optimist. Aim high, don’t limit yourself, and always strive for accomplishments that are meaningful and aligned with your values. This is the classic “CEO” way of looking at the world and deciding where to go – strategy, vision, and confidence are huge assets here. When goal setting, make sure you show your work! Define goals in the form of “We’d like to do X because of A, B, and C”. This provides important context and you’ll find that there are often other cheaper better routes that could be had which your haven’t considered.
Second, Become a Pessimist
Once you’d laid out your goals, make sure you switch hats and cast an incredibly cynical eye over your plans. You want to identify everything that can, will, or should go wrong. This is the perspective that a “COO” or “CTO” would take, as they’re the ones seated more firmly in the trenches. The important thing here is to engage your team and let them know it’s OK to second guess goals in the context of determining how they’ll be achieved. By critically assesing what it will take to arrive at your destination, you’re ensuring you don’t run off the rails enroute.
Now You’ve Got a Plan
Forcing yourself to wear both hats is hard – it’s often difficult to pull yourself across the chasm if you’re naturally predisposed to one outlook or the other, but if provides the following:
- Builds a culture of intellectual honesty. It’s always easier in a team environment to just go along with the flow and feel like you don’t have any skin in the game. If your team feels they can object or hone objectives, they’ll perform better.
- It can reduce the risk of making major mistakes. By critically attacking your objectives you’ll anticipate problems and avoid major pitfalls that could have been forseen. You’ll never know what you don’t know, but often teams drift into problem areas they could have avoided.
- In dysfunctional organisations, it’s amazing how almost everyone involved will know (and be able to point out good reasons) how goals won’t be achieved, well ahead of time. You’ll prevent this kind of “death by politics” syndrome which affects a lot of companies.
- Bottom up planning is always the best way to meet top down objectives. In other words, the high level goals can be set by the product owner, CEO, or visionary, but they’re on the worst vantage point to actually see how to go about achieving these things. A tip on how to encourage realistic plans – don’t confer time estimates of any kind when setting strategic goals. Just say “We’d like to do X” and see what comes back!
Lastly, Remain Engaged
Plans sometimes need to change. You’ll need to react to new things. As your team engages with the problem the goal-owner will need to remain intimately engaged with the team. Fine tuning your goals is a necessary part of any meaningful project or endeavor – not fine tuning will just ensure failure.