Step 2: Hunt for Possible Fits

Feb 5, 2026

Step 2: Hunt for Possible Fits

Once you’ve sorted out your wish list — the criteria you’ll use to determine whether a given opportunity is a fit or not — what next?

We’ve got to find some roles that might match your priorities.  This is the “H” in the 5 Step CHART framework.  It stands for “Hunt” (or “Hypothesis”, if you like it better).  Where might you find the things on your wish list?

There are a couple of approaches to identifying alternatives. The one I like best starts with the ideas you’ve already had.

Now, this can feel silly.

If you had thought of a GOOD idea, one you thought would get you what you wanted and you knew how to attain, you wouldn’t need a career coach. So most people come to me convinced they have NO GOOD IDEAS and the only things they have thought about are VERY BAD IDEAS.

Sometimes that’s the case, and sometimes it isn’t. My job as a coach is to test the rigor of your thinking, and to help you recognize where you might have made an unfounded assumption.

I start by challenging clients to identify as many options as they can. I have a simple spreadsheet exercise prompting clients to list possibilities. The most obvious. The most lucrative. The most inspiring. The scariest. The most prestigious. The things that would create the most learning or growth.

Filling out these lists is hard, but the categories help.  You’re not trying to find the perfect role.  Instead, you’re making a list of imperfect possibilities.  If you were only optimizing for this one characteristic, what might you consider?

By definition, anything that you’re not already doing will have some risks and require some new skills.  So I make sure to tell them that the options on the list will probably all have something wrong with them.  We want to list them anyway.  They’ll have a chance to tell me about the obstacles.

It turns out that assessing the magnitude of the risks and the difficulty of conquering them is often a place where my clients haven’t been rigorous or disciplined.

When we start to talk about options, I ask them to describe the possible benefits and the drawbacks they associate with each idea. As we sift through their assumptions, we look at which ones are backed by evidence or information, and which are simply guesses. The spreadsheet has hidden columns where clients can examine their objections and identify which ideas might be worthy of some more research.

In the video below, I talk about how I use this resource with clients.

There are other possibilities for finding opportunities and developing a target list of roles, industries, or organizations — but this is how I begin with most clients.

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