How do I evaluate two completely different offers?

Question:
I’m a senior executive and left my previous position because it had become a role I did not want. Now I’m in the enviable position of having two offers—same money, etc—but completely different roles. One role is being created, the other already exists. I like different things about each and am not sure how to sort out my options. Any ideas?  A.M., New York, NY

Answer:
Congratulations! It’s rare that the timing works out so that you have two offers concurrently, especially at a senior level. This situation differs from other issues that require strategic thinking because it also involves emotional factors. It’s easier to start evaluating using less subjective aspects of the issue before you add in your feelings.

Which role will get you closer to your long-term goal? If you’re not sure what your long-term goal is, think about what you see yourself doing a few roles down the road. Even if you can’t name the role, you can probably identify the type of impact or situation you want, e.g., working globally, running a standalone division, etc. What are the gaps between what you do now and what you think you need to know for your future roles? What are those skills? It’s important to keep track of these because regardless of which job you take, looking at your list will let you know when it’s time to move on.

Since you left a situation that wasn’t working, check to make sure that it’s not affecting your thinking. For instance, if you left because you didn’t have autonomy and one of these new roles appears to have autotomy aplenty, you might give it more weight than it deserves.

Another consideration is the challenge that comes along with creating a role versus stepping into a role someone else has held. Depending upon how you define risk, either one could look risky. You might see creating a new role as risky because you’re introducing change into an organization and will have to sell your benefit consistently. Or you could see it as less risky because there is no benchmark and you can tailor the position to play to your strengths, assuming it meets business needs.

How you see the opportunity will affect how you experience the job. If you are still torn between the two offers after you’ve evaluated the rational attributes and made sure that you aren’t reacting to your most recent situation, then go with what you think is the least risky option. If you perceive the risk level as high, you will likely put additional pressure on yourself and that could easily get in the way of having a good experience. Good luck!