“You’re overthinking this.”

Alan Weiss, NYT best-selling author and advisor to many of the world’s top consultants, has told me this more than once.

He’s right.

My tendencies lean toward what a friend of mine calls, “measure seven times—cut once.”
I don’t like to make mistakes.

Unfortunately, that whole tendency can be a mistake, especially in leadership or entrepreneurialism.

We can’t know everything. Windows of opportunity are real and finite. We lead and grow through ambiguity.

Most of my growth, and the best things in my life (especially my wife and kids), came from committing to decisions that I couldn’t possibly “know enough” about.

Maybe you identify.

On the flip side, many leaders prefer to ‘decide from the gut.’ Speed and action are their preference.

I often see this with clients who will show me their strategic plans before we do the strategic planning. Or they call the team together to make a decision, and then inform them that it’s already been decided and put into motion.

Jump first and look later. It’s true, they do get off the dime. But often struggle with follow-through or maintaining the buy-in of others.

There must be an approach that speeds up the overly analytical and cautious while providing a framework for the speedy and intuitive.

And here it is.

The Confidence Method™

Phase 1: Set Bearings (Align & Define)

1. Involve Who Matters (Not Those Who Don’t)

People who matter are:

• Decision Maker(s): Who has the power to decide or veto?
  • They must be part of the process. Otherwise, their default is usually “no.”
• Supporters: Who do you need to say yes?
  • Will they support a good decision, as long as they’ve been consulted? Then keep them in the loop.
  • Will they only support it if they help make the decision? Then find an appropriate role for them.
• Information Bearers: Subject matter experts and implementers who shape a good decision.

Not everyone needs to be involved in the same way or at the same time.

Rule: Only decision makers can make the decision. Supporters will maintain it. Information bearers ensure it’ll work.

2. The Strategic Gate (Your “Why” Filter)

Before making a decision, ask if the issue is even worth resolving:

• Does this decision align with our core values?
• Does it move us meaningfully toward our vision?

If the answer is no—why is this even on the table?

Rule: A “good” decision can still be the wrong decision if it doesn’t align or move you forward.

3. Define Criteria & Interests

Decision-making gets bogged down or stuck in conflict when no one agrees on what makes a good decision in the first place.

Before you generate options, define:

• Must-haves: Non-negotiables (e.g., must launch by Q3, must stay within budget)
• Want-to-haves: Ideal, but not essential. Use them as tie-breakers.

Rule: Shared criteria create a platform of agreement and clarify options.

Phase 2: The Options (Generate and Filter)

4. Generate Options

You need at least three options.

One option = no decision.
Two options = a dilemma or a deadlock.
Three or more = space to lead.

I often push clients to generate 20+ options. They usually hate it.

The first 8–10 come fast. The next 6–7 feel like a slog. Then something unlocks. Almost always, the gold is in the last few.

Rule: The best answers are often not what you are thinking right now.

5. Filter – Impact vs Cost

Is the juice worth the squeeze?

Rate each option:

Impact: 0 = no impact, 10 = completely addresses the issue

Cost (effort/resources): 0 = very costly, 10 = very easy

• High Impact / Low Cost: Good options.
• High Impact / High Cost: Estimate ROI. Especially if no easy wins exist.
• Low Impact (any cost): Why bother?

Rule: Avoid effort that doesn’t create impact.

Phase 3: Stress Test (Evaluate Quality)

6. Do We Know Enough?

Revisit your criteria from Step 3. For each remaining option —what do you know vs what are you guessing? According to General Colin Powell:

• < 40% confidence = You’re guessing. Get more data.
• >70% confidence = You’re probably overthinking it.
• 40–70% = Sweet spot. That’s when a leader needs to act.

Ask: Is this decision a one-way or two-way door?

• If it’s reversible (two-way), 40% is enough.
• If it’s not (one-way), push toward 70%.

Rule: Leadership is most valuable in uncertainty. It’s rarely needed elsewhere. Delay can often do more damage than imperfection.

7. Seek Disconfirmation

Especially for one-way decisions:

• Assign a devil’s advocate. Or recruit the naturally skeptical member of your team.
• Ask: What assumptions are we making? What could go wrong?
• Run a pre-mortem: “Let’s imagine this fails in a year. Looking back, what most likely caused the failure? What did we miss?”

Rule: Actively resist groupthink, confirmation bias, and shallow consensus.

Phase 4: Execution (Implement and Check-in)

8. Decide, Commit & Review

• Commit. Once the decision’s made, move.
• Communicate the ‘why’ and the criteria. For stakeholders who weren’t in the room, connect the dots for them.
• Set review dates. Separately evaluate execution and decision quality.

Explore:

• Was the decision good (enough)?
• How well is it being executed?
• Are we getting the results we expected?
• What do we know now that we didn’t know before?

Rule: Good decisions can be poorly executed. Poor decisions can be well executed. Don’t confuse execution quality with quality decision-making.

Don’t wait for perfect clarity. Create your own and act.

Most decisions don’t have a single right answer. But there are better and worse ways to decide. The framework above will reliably lead you to good decisions quickly.

Build that skill.

Take good care,

Christian