How many decisions did you second-guess this week that you’d already, technically, made?

Not just the big ones– what about the myriad small ones? 

• Which version of the email to send. 
• Whether to move the 2pm meeting. 
• Whether to say yes to the request that landed in your inbox at 8am. 
• Which competing meeting was the priority to attend.

You made the call, then you reopened it in your head three more times before lunch.

If that sounds familiar, you’re not alone, and you’re not indecisive by nature. 

You’re overthinking because nothing in your day has taught you which decisions deserve that much energy and which ones don’t.

This month, I want to talk about confident decision-making as a skill built on clarity, values, and speed, because the leaders who move fast and well aren’t smarter or less careful. Rather, they’ve just stopped treating every decision like it’s the same size and requires the same energy..

The Leadership Problem: Death by a Thousand Small Decisions

Here’s what’s breaking managers and business owners right now: decision fatigue disguised as thoroughness.

You tell yourself you’re being careful, thoughtful, and responsible. But what’s actually happening is you’re spending the same amount of mental energy on “should I switch this meeting to Thursday” as you are on “should I restructure this role.” 

Our brain doesn’t naturally sort decisions by stakes. Left unmanaged, it treats them all as worthy of full deliberation.

The result:

• Small decisions take longer than they should, which delays everything downstream of them.
• You arrive at the genuinely hard decisions already depleted, because you burned your clarity on the easy ones.
• Your team waits on you, which slows them down too, and indecision at the top quietly trains a team to hesitate as well.
• You replay decisions after they’re made, which costs you twice the energy for the same call.

This is a systems problem, and systems problems have systems solutions.

The Traditional Strategy That Still Works: Sort by Weight, Not by Worry

The leaders who decide well aren’t running every choice through the same process. Instead, they’re sorting decisions by weight before they ever start deliberating.

Two categories matter most:

1. Reversible, low-stakes decisions. These are the types of decisions where if you’re wrong, the cost of fixing it is small. Think along the lines of: which template to use; whether to take the call now or in twenty minutes; any item to order less than $XX [Enter your comfortable threshold. For mine this is $200.] Most of what crosses your desk in a day lives here.
2. Irreversible or high-stakes decisions. These deserve real time: a hire, a policy change, a client/patient relationship, anything hard to undo, anything more than $XX [Enter your comfortable amount as a default.]

The strategy is simple to say and hard to practice: match your deliberation time to the actual stakes of the decision– not to how it feels in the moment.

Practical tips:

• Before you start weighing a decision, ask: “If I’m wrong, how hard is this to undo?” If the answer is “not very,” decide now.
• From a financial perspective- and remember that time is money- ask: “If I made the wrong decision, how much will this cost to undo?” Put a dollar value on it, and decide what you’re comfortable with.
• Give yourself a real time cap for low-stakes decisions. For example: two minutes; the length of one cup of coffee; decide during one lap around the block…whatever forces momentum.
• Reserve your slow, careful thinking for the decisions that are actually hard to reverse. Protect that energy instead of spending it everywhere equally.
• When you notice you’re re-deciding something you already decided, name it out loud: “I already made this call.” That alone often stops the loop.

This is the part most leaders already know intellectually. The next part is why knowing it isn’t quite enough.

Why This Strategy Fails Without Support

Sorting decisions by weight sounds simple; however, in practice it falls apart for a few very human reasons.

• Mental load. in the middle of a very packed day, you’re not pausing to ask “how reversible is this?” You’re just reacting, and reacting under load defaults to overthinking– not clarity.
• Inconsistency. You might apply the framework brilliantly on Monday when you’re well-rested from the weekend and abandon it entirely by Friday when you’re tired. A framework you only use when you have spare bandwidth isn’t a dependable framework.
• No time to pause. The whole premise requires a moment of reflection before you decide, and most calendars don’t have these moments built in anywhere.
• Values aren’t always visible in the moment. Knowing a decision is low-stakes is one thing. Knowing what you actually value- so the decision is easy once you see it clearly- is a separate problem entirely. Most overthinking is about not having sorted out your own priorities and values ahead of time.

This is exactly where AI becomes useful.

How AI Strengthens This Strategy

AI doesn’t make your decisions. 

Let me say that again: AI doesn’t make your decisions.

What AI does well is hold up a mirror and ask the questions that help you see your own thinking clearly and faster than you’d surface it alone.

The mechanic is simple: instead of asking AI “What should I do?” you describe the decision and let it ask you clarifying questions. 

That single shift of questions instead of answers is what keeps AI in the mirror role instead of the decision-maker role.

What this looks like in practice:

• You give AI the decision and the context. It asks you what outcome you’re actually optimizing for, what you would regret more, or what’s non-negotiable for you within that context.
• Answering those questions out loud (or in writing) does the real work. The clarity comes from you– surfaced faster than it would in your own head alone.
• You walk away in minutes with the thing that was actually missing: a clear view of your own priorities and values.

This works because the questions are doing what a trusted colleague or coach would do: helping you hear yourself think, but not providing the answer to you.

Real-Life Situation

Let me share a real story where I actually didn’t follow my own advice and it turned out, well…fine. 

I needed a new Oura ring and couldn’t choose a color.

Such a simple decision but I treated it like my life depended on it. My previous Oura ring- which was shiny black- had run its course over 4+ years and the battery wouldn’t hold a charge for an entire day, so it was time to upgrade.

Over the previous 4 years, Oura had come out with many more colorful and finish options. I thought I would just replace like for like, but then I started looking at all the options and found myself spending way too much mental effort and energy on making a decision.

So one night I turned to Jack for assistance, the name of my ChatGPT. Jack walked me through about 7 thoughtful questions- what are my favorite colors, what does my wardrobe color scheme typically include, and what activities fill my day. In less than 10 minutes it had made a decision and I agreed. I ordered the ring and called it a day.

When the ring arrived 5 days later, the color turned out to be perfect.

So, yes, I did in fact let AI make a decision for me during a week when decision fatigue was so strong and real for me that I knew this simple ordering task would otherwise get pushed off until the next month. 

Sometimes it can be ok to let AI choose for us. But my example was very low-stakes, and technically, I was the one making the final decision to pull the trigger and order that color.

Real-Life Use Cases for Managers & Owners

Let’s pivot and look at some more common use cases as managers and business owners:

Calendar: Are you torn between two ways to restructure your week? Describe both options to AI and ask it to reflect back what each option seems to prioritize, then ask yourself which priority actually matches your goals and values right now.

Delegation: Are you unsure whether to hand off a task or keep it? Ask AI to walk you through what you’d be optimizing for in each scenario– capacity, development of your team, or control– so you can see which one you’re actually choosing for and can make an appropriate decision that aligns with team and/or company goals.

Communication: Are you drafting a hard message and second-guessing the tone? Ask AI to ask you what outcome you want from the conversation before you write a word. The message gets easier to write once the goal is clear.

Planning: Are you weighing two strategic directions for the back half of the year? Use AI to lay out the tradeoffs of each as you’ve described them, then decide based on what you see- not on which option AI seems to favor.

Guardrails: What AI Should Never Do for You

This is the part that matters most, because the line is easy to blur once a tool starts feeling helpful.

• AI should never make the final call. It can inform, question, and clarify. The decision, along with the responsibility and accountability for it, stays with you.
• AI should never be used for people decisions. Hiring, firing, discipline, and anything that affects a real person’s livelihood requires human judgment, context, and accountability that AI cannot carry.
• AI should never replace your gut instinct on values-based calls. If a decision is fundamentally about what you believe is right, no amount of AI reflection should override what you already know in your gut.

AI’s job is to help you think clearly and quickly, but your job is still to decide.

Action Step

One human change: This week, before you decide anything that feels hard, ask yourself one question first: “If I’m wrong, how hard is this to undo?” Let the answer set your pace.

One AI integration: The next time you catch yourself circling a decision, open a chat and describe it. Then ask AI to question you, not answer you, until your own priorities are clear.

Start with one decision. Notice how much faster clarity comes when you stop treating every choice like it’s the biggest one you’ll make today.

If you want to take a deeper dive into a guided step-by-step process using key AI platforms, be sure to sign up for my weekly emails and special webinar offers only for my subscribers and followers: https://erinclemens.com/email-sign-up/