A few years ago, an old manager reached out to me and asked if I would consider switching to his team at Amazon. I loved working with this manager but I was going up for promotion and didn’t want to take a risk by switching before that went through. He mentioned that the position may not be there when I was ready and to let him know when I decided.
I made a pro / con list and still couldn’t make a decision, so I mentioned my concerns to him. He recommended I take a piece of paper and divide it into quadrants. Then, use each quadrant to describe the best and worst cases for the short and long terms of making each decision.
For each quadrant, try to be specific about what that scenario actually looks like. Don’t write “things go well.” Describe what “well” means. What does the best case look like in six months? In three years? The more concrete you make each scenario, the easier the next step becomes.
Once you’ve written down the cases, score how happy you’d be if each scenario played out on a scale of 1-10. This is where the exercise earns its keep. The pro / con list had left me stuck because every factor felt equally weighted. Putting a number on each quadrant forced me to confront which outcomes I actually cared about and which ones I was overweighting out of fear. Here’s what a (partial) view of my decision then looked like:
Staying Put
Switching Teams
After I went through the exercise, I had a clear answer about what I should do. Taking an average between the best / worst cases for both paths, it seemed like I would be happier to make a change than to stay and potentially make it later.
Now that I’m a few years down the line from that decision, I’m glad I made it when I did. The quadrant predictions mostly held up. Working on that team was great until it wasn’t. The product eventually struggled and has since shut down. My long-term worst case came true. But the time I spent there was fulfilling, I learned a lot, and I don’t regret making the switch when I did. The exercise didn’t promise a perfect outcome. It helped me pick the path I could live with either way.
I shared this process with a colleague who was making a difficult decision and they asked for a reference. I couldn’t find one, so now there’s a reference! I hope you find this helpful if you need to make a difficult decision.