How to make decisions
Clarify your goals, values, and fears to decide with confidence.
For the past six-ish years, I’ve been doing one-on-one negotiation coaching and decision-making sessions. I’ve only done them with people I know personally, or through an organization we’re both part of. Now I’m getting ready to open them up to anyone.
In addition to learning about logistics like setting up billing and scheduling, I’ve been reflecting on my coaching practices.
Over the years, I’ve developed a framework for these conversations. You can book a session with me if you’d like, but you can also use this framework on your own, or with someone in your life who’s a good listener and willing to think through issues with you. You could even work with a friend who’s struggling with a dilemma of their own, and take turns listening and strategizing with each other.
First, some context: This is meant to be a one-time conversation or self-driven process, not an ongoing series. The goal is to move from confusion to clarity, while avoiding overthinking. It works especially well when you have a problem whirling around and around in your mind, and you could really use some outside perspective but don’t want to bore your friends with a million details. I like this framework for thinking through any type of life decision, although I limit my coaching sessions to work-related issues because that’s my expertise and I’m not a therapist.
Three steps to making a decision with confidence
1. Clarify the situation – and the story you’re telling about it.
I’ll start our coaching session by inviting you to describe the situation. What’s going on? What problem or issue do you want to resolve?
I need to know the facts, but I’m also listening for clues about how you perceive the situation. What story are you telling yourself, and me? Are there alternate plausible stories that might change how you are looking at the situation and your choices?
Here are some observations I might make, and ask followup questions about:
I hear you repeating [word or phrase] when you talk about this.
You started out by saying you want X, but when you talk about X you sound resigned and unhappy.
You sounded interested in Y, but then said it’s not a possibility. Why isn’t it?
You said you’re sure the response to your request will be Z. What makes you think that?
You said you and your coworker have a pattern of hostile interactions. To me, the examples you gave sounded neutral, and similar to interactions at work that I would normally have. So I feel like I’m missing something. Tell me more about what makes them hostile.
These questions are not meant to be “gotcha”s. They highlight areas where I want to dig deeper to understand the situation better. A key part of understanding the situation is to accurately separate objective facts from your interpretations and assumptions. Sometimes you’ll have a very clear answer. Sometimes the questions will lead to more questions from both of us.
2. Clarify what matters to you.
We have a good grasp of the situation. Now, what do you actually want?
I have a whole series of questions I’ll ask here, aimed at eliciting the following items. (I’ve tried to turn these into an acronym, so far without success.)
Your needs – what’s a necessity, and why?
Your wants – what would be nice to have, and why?
Your absolute nos – what’s something you definitely do not want, and why? (Essentially, a negative need.)
Your avoids – what would you prefer not to do, although it’s not dealbreaker, and why? (Essentially, a negative want.)
Your concerns and fears – what are you worried about, and why?
Your success stories and cautionary tales – is there some situation you’re looking to as an example, or conversely, a situation similar to yours that went wrong?
In my in-progress book, I call this your “what matters list.”
I find this exercise incredibly useful in general. Do this once or twice and you’ll have a much more solid grasp on your values and priorities. Be clear on your values and priorities, and just about every life decision becomes much easier.
Notice the “why”s attached to each question. It’s important to interrogate yourself. Go deeper than “this is what I want.” When you can figure out WHY you want it, and identify your underlying needs, you can unlock all kinds of possibilities that might meet the same need in different ways.
3. Strategize about next steps.
Finally, we’ll brainstorm and strategize about next steps. This is the stage that varies the most in each conversation, because it depends on what would be most helpful to you. For some people, it’s a concrete action plan with steps to take. For others, it’s noting some issues they want to reflect on more, or learn about, or talk to others about. For those who have arrived at a decision during the call, we may focus more on the implications of that decision – what will you encounter going forward?
If we’re preparing for a negotiation, this stage is when we’ll also develop possible scripts for you to use, and practice communicating clearly and directly in a way that feels comfortable and authentic to you.
This stage is collaborative, with both of us brainstorming together. I may make suggestions, but they will be framed as “How would you feel about this? Would you feel comfortable doing this, or is this something that wouldn’t feel right to you? Is this something you’d be excited about, or dread?” The specific ideas, in my opinion, matter less than learning about what matters to you. A knee-jerk “no way” to a suggestion is highly educational.
At the end – whether you’ve done this with me, with a friend, or with your journal – you’ll have a better handle on not only this problem, but how to solve future problems by clarifying the situation, your goals, and possible actions to take.
Happy decision-making!
If you’d like to book a coaching session with me, use code “newsletterfriend” for a 30% discount.

