How to think through complex situations and develop more thoughtful recommendations
One of the most common challenges I see when working with senior leaders isn’t a lack of experience or ability. It’s something a bit more subtle – a lack of confidence in their own thinking. This can lead to hesitation and second-guessing, especially in complex situations where there isn’t a clear right answer. Unfortunately, this can have a not-so-subtle impact on their executive presence, their decision-making authority, and, ultimately, the confidence others have in them.
Perhaps you’ve experienced second-guessing yourself. I know I have. When it happens, a familiar pattern emerges. You might find yourself:
· Reframing the issue over and over again, hoping more clarity will magically appear.
· Turning to others for ideas instead of trusting your gut.
· Deferring to your boss for “the answer” instead of proposing possible solutions, asking for input, and making a decision.
· Seeking consensus instead of setting direction.
· Coming across to clients or colleagues as reactive rather than strategic.
Second-guessing doesn't always look particularly dramatic. But the cost is real.
Second-guessing doesn’t always look particularly dramatic. It can appear pretty quietly, showing up in your hesitation or over-analysis instead of your conviction and decisiveness. And over time, this pattern can cause more than a little frustration for everyone… You start to feel dependent. Your boss resents getting pulled back into the weeds. And clients don’t feel like they’re being led as they should.
The truth is you probably already have much of what you need to navigate these situations. What’s missing might be a go-to process for thinking through complexity and developing sound recommendations that would help you feel more confident making the tough calls.
Start by Shifting Your Mindset
Before we get into the details of a process, I encourage you to take a minute to consider your mindset. The way you think about decisions often matters more than the steps you take to make decisions.
Ask yourself this: What am I most worried about when it comes to making big decisions? Not having all the answers? Getting it wrong? What makes me not trust myself?
Instead of focusing on certainty or perfection, it can be more helpful to focus on how you approach ambiguity, your determination to be a learning leader, and your ability to refine decisions as you go along.
Here are a few mindset shifts that might help:
From | To |
“I need more direction or input before I can confidently take action.” | “By asking the right questions, I can gather the information I need to develop viable options.” |
“I don’t want to get this wrong.” | “My job is to come up with a well-reasoned point of view, not the perfect solution.” |
“It needs to be correct right out of the gate.” | “I can make the best decision with what I know now and refine it as I learn more.” |
Second-guessing yourself | Drawing upon your knowledge, instincts, and experience |
Escalating quickly to reduce risk | Thinking first, then asking for help or additional input when it is truly needed |
Being valued primarily for what you do (good execution) | Being valued primarily for how you think (good judgment) |
Shifting your mindset can help you realize:
· You don’t need more clarity before you decide. You need more confidence in your instincts.
· Seeking input from others is a choice—not a thinking shortcut. You can determine when getting ideas or feedback is really needed.
· Your real value is not in execution alone. It is probably much more about developing thoughtful recommendations, setting clear direction, and finding solutions that can make a difference.
From the Problem to the Solution
With a new mindset, you might also find your focus shifting more quickly and naturally from the problem to the solution. It’s an important shift.
When you focus too much on the problem itself, the situation can loom larger than it really is. You can become fixated on diagnosing rather than resolving, talking rather than moving. And delayed action can lead to missed opportunities.
Delayed action can lead to missed opportunities.
I can recall times when I got stuck in this problem/worry loop. That was when the inner critic seemed to take over for me, too, and I began to wonder if I was even capable of coming up with a solution that would work. Then the second-guessing sort of took over and an answer seemed farther and farther away.
The key is not to sit too long with the problem. While you want to understand the dynamics of a situation and what’s at stake, you need to turn the corner at some point to focus on solutions-finding. This can help you see things as they really are, understand when you have enough information to make decisions, and start making progress, even if it’s just early steps.
Are You a Solutions-Finding Leader? A Quick Self-Assessment
We all want to see ourselves as a solutions-finder, especially when situations are complex and answers are hard to come by. So, how do you stack up? Here is a quick self-assessment that can help you evaluate your current thinking process. Be honest so you can see where your gaps are.
Instructions: Think about a recent decision or challenge and consider how often each statement is true for you.
Use this scale: Never | Sometimes | Frequently | Always
If a few of these statements give you pause, that’s okay. There’s no “right” score here. The value is in noticing patterns—where your current thinking process is serving you well and where you may be relying on escalation or caution more than necessary.
It’s Not About Personality
The good news is that solutions-oriented leadership isn’t about personality or instinct alone. It’s about honing a few skills that can be practiced and strengthened over time and having a simple way of thinking things through. Then you’ll feel more confident handling situations like this…
A key client calls late one afternoon with a particularly thorny situation. The timeline has shifted unexpectedly on a big project, their budget is tight, and you can tell there’s pressure building. They ask, “What do you recommend?”
As soon as you hang up, the second-guessing starts:
· Do I know enough?
· What if I get this wrong?
· Should I run this by someone else first?
Without a way of handling the pressure and uncertainty of the situation – and the inner-critic takeover that might be happening – this is where you can get stuck. Let’s take a look at a framework for thinking things through that might help you find solutions, no matter the complexity, and feel more confident moving forward.
The CORE Four-Step Model
I’ve created a simple four-step decision-making framework I call the CORE Model. It’s designed to help you set aside emotions and assumptions and get to some viable solutions as quickly as possible. It’s also practical, repeatable and usable in real time. I hope it can be helpful to you – or at least give you some ideas for a process you can develop for yourself.
Here’s an overview of the four steps with a few questions to ask yourself in each step.
Situation: You have a complex decision to make. Emotions are high. How do you think it through?
Step 1: C — Clarify
Establish the facts – what you know as well as what priority you should be giving this vs other things on your plate.
· What’s happening here—facts versus interpretations or assumptions?
· What is the real dilemma we’re trying to solve? “I (and my clients) want this, but here’s what is standing in our way.”
· How important is this to the client right now (on a scale of 1-10)? How can I hand off/pause/find the time to address this appropriately?
Step 2: O — Outcomes and Options
Define success and explore possible paths forward.
· What would a “win” look like in this situation?
· What constraints are we working within?
· What ideas do I have for solutions – a few options that might work?
· Who else, if anyone, could I consult for different perspectives, ideas or input?
Step 3: R — Recommendation
Form a reasoned point of view.
· What do I believe we should do and why?
· What risks or trade-offs are we accepting?
· What resources do we need to have in place – time, budget, talent?
· What priorities possibly need to shift so we can execute well?
· How should this be framed for the client to get their buy-in?
Step 4: E — Execution
Bring the plan to life – not just making things happen but continuing to lead with judgment as the plan unfolds.
· What are the first few steps we need to take to create some momentum?
· What ownership do we have to keep things going vs stopping to get the client’s approval?
· What checkpoints tell us we’re on the right track and allow us to adjust?
· What’s our Plan B if things go wrong?
Why This Matters With Clients
Clients, whether internal or external, don’t just want good execution. They want good judgment, which of course is something AI can’t provide nearly as well as you can. Clients want partners who can navigate the challenges, make reasonable trade-offs, and lead with well-thought-out recommendations, not simply waiting for direction.
Don't be afraid of being wrong. Be more concerned about not having a point of view.
A Few Things to Keep in Mind
Regardless of whether you go with the CORE Model or come up with your own, have a go-to process in place to help you navigate these types of situations. And keep in mind a few things…
· There are times to seek additional input, but do your homework first. Escalation and seeking input from others should be a leadership choice, not a thinking shortcut.
· You’ve done your job if you can clearly articulate:
o the situation
o the options
o the risks
o and a reasoned recommendation
· Don’t be afraid of being wrong. Be more concerned about not having a point of view.
· Value thoughtful attempts over perfection.
· Few decisions are truly final. Most can be adjusted as you go along and you have more information.
· Be a learning leader. A growth mindset will serve you far better than waiting for certainty.
A Final Thought
You don’t need certainty to lead well. You need clarity, judgment and the willingness to have a point of view. The CORE model offers a practical way to do that—without overcomplicating decisions or slowing things down. And in my experience, that confidence is often what separates reactive leaders from trusted advisors.
If this resonates and you’d like to explore how leaders in your organization can strengthen this capability, I’d love to continue the conversation with a 1:1 advisory session or a workshop for your team.
