3 Steps to Help You Stop Second-Guessing Your Leadership Decisions

How do I stop second-guessing myself? 

This was a question one of my clients, Sarah, came to coaching with. 

Sarah was an accomplished manager and executive. During her career, she had earned two PhDs and over the course of twenty years, worked her way from the legal department to director of business development at a luxury retail company. 

One year earlier, the CEO had tasked Sarah with starting a sub-division within the business development department to focus specifically on innovation. This meant her team was responsible for creating and implementing cutting-edge strategies to modernize the company’s marketing and distribution channels. 

As a Sensitive Striver, Sarah was thoughtful, empathetic, and skilled at spotting opportunities others missed – a combination of skill which made her a perfect fit to lead the team.  

But Sarah had started her career as a lawyer and operated under the false belief she had no idea what she was doing. The thought of building the innovation team filled her with imposter syndrome. She doubted whether she had what it took to get the job done and make their work a success. 

Soon, her insecurity started to hold her back in other ways, namely in terms of her ability to make decisions. Sarah often found herself overthinking choices – both big and small – which stressed her out and slowed the team’s progress. She had trouble trusting her own judgment, and instead sought excessive amounts of outside approval before making a call. 

Most of all, Sarah was constantly second-guessing herself. 

After she would eventually make a decision, she would find herself preoccupied by all the what if’s (What if we had chosen direction B? What if X wouldn’t have happened? etc). She would toss and turn at night (and feel distracted at her desk during the day) by thoughts of whether she could have made a better choice. 

In other words, Sarah couldn’t stop ruminating. 

What is Rumination?

Ruminating is a type of overthinking that involves obsessing over the same thoughts. Typically these are “dead-end” thoughts that aren’t productive, positive, or useful. It’s as if your mind is a record, stuck on the same track that keeps playing over and over – hence the second-guessing. 

When you’re ruminating, you’re dwelling and living in the past. You analyze and replay situations over and over. You may rehash conversations, dissect people’s body language, and stress about what you did or didn’t say. 

When it comes to decision-making, ruminating can look like: 

• Beating yourself up for making a decision too slowly
• Wondering if there were better options
• Replaying missteps or mistakes you made 
• Worrying about other people’s reactions and judgments 

Thinking about a decision can be helpful – especially if it leads to a resolution or provokes new solutions and insight. But rumination doesn’t do that. It simply causes distress and drains you of mental and emotional energy you need to do your job effectively. 

Why Rumination Affects Sensitive Strivers

Rumination to some extent is normal because we tend to believe that by ruminating, we’ll gain insight into a problem. 

The problem arises, however, when it becomes an ingrained mental habit that begins to hold you (and possibly those around you) back from your full potential – as it was for Sarah in the story above.  

Ruminating is also common in people who possess certain personality characteristics, like Sensitive Strivers. 

As driven, deep thinkers, Sensitive Strivers pride themselves on being conscientious and thorough. When well balanced, their thoughtfulness can be a strength – contributing to above-average self-awareness and giving them superpowers like intuition and creativity. 

However, when unbalanced, their Thoughtfulness can become a hindrance, which is exactly what was happening for Sarah. 

Sensitive Strivers also tend to be perfectionists. So while they deliver high work quality, they are often extremely hard on themselves and their own worst critic, which leads to rumination.

If this sounds like you, then fear not, because it is entirely possible to rebalance your Thoughtfulness. With new tools to channel your sensitivity and ambition, you can stop second-guessing yourself and learn to regain your confidence and trust your judgment. 

How to Stop Second-Guessing Yourself 

Here’s a three-step process to end rumination that I coached Sarah through, which will also serve you. 

1. Interrupt 

At its core, rumination operates on negative self-talk. These unhelpful thoughts can sound like: 

• I’m such an idiot. Why didn’t I think of that sooner? A smart person would have. 
• This is all going to turn out to be a disaster. 
• I bet everyone is thinking I’m a failure. 

Everyone’s inner critic is different, so your brand of negative self-talk sounds different. Regardless, your first step remains the same, and that is to interrupt the unhelpful thoughts. 

This works because rumination is like an automatic, knee jerk reaction. It may be so automatic that you’re not even aware it happens. But interrupting the thoughts helps you build internal strength and command to be more in control of your experience. 

You can interrupt your negative self-talk in a few ways, such as by silently saying STOP or “This isn’t helpful” or snapping a rubber band on your wrist. I also like to have my clients name their inner critic, so they can find emotional distance from their cruel inner voice when it arises. 

2. Accept

Rumination and second-guessing yourself are characterized by wishing you or a situation were different or beating yourself up for all the woulda-coulda-shoulda’s that exist in decision-making. In both cases, you are wasting valuable time and energy fighting against reality. 

A much more productive approach is radical acceptance. Radical acceptance is not the same as resignation or passivity. Rather it is about:

• Taking ownership and responsibility for yourself within a situation
• Adjusting your perspective to willingly and realistically take in the facts, realizing you can’t change them even if you’d like to
• Assertively moving forward without staying stuck in thoughts like “why me,” “this is unfair,” or “it wasn’t meant to be this way.”

Embrace radical acceptance by rooting into the present instead of fighting it. Sarah did this by reminding herself “this is where I am now” or “I don’t like the situation we’re in, but I can’t change how it unfolded” after making decisions. 

3. Redirect 

After you’ve interrupted rumination and accepted reality, you can approach the final step in the process: redirecting your thinking. 

By redirecting your thinking, I mean channeling your depth of thought and intelligence more constructively. Especially, you can do this through self-coaching – asking yourself open-ended, growth-oriented questions that open up new possibilities. 

Self-coaching questions to stop second-guessing yourself include: 

• How can I make the most of the circumstances in front of me? 
• How might someone who is confident respond?
• How would I advise my closest colleague to approach this?   
• What thought helps me feel energized and powerful? 
• What would I believe if I knew everything was going to work out?
• What’s the very best next step I need to take?  

Keep in mind that you can’t attempt this process once and expect rumination to magically dissolve. Changing any habit, especially a mental habit that’s as ingrained as second-guessing yourself, requires repetition and dedication. 

But if you follow the steps above, soon you’ll experience greater success without so much stress.

Check out the Ultimate Guide for Sensitive Strivers for free resources to outsmart imposter syndrome, stop second-guessing yourself, and much more.

Want to Learn More? Check Out My LinkedIn Learning Course

The sooner you take control of overthinking, the happier, more productive, and effective you’ll be at work. 

That’s where my new LinkedIn Learning course, Overcome Overthinking, comes in. 

This course will show you how to: 

• Stop worrying about things you can’t control
• Make better, faster decisions with less stress
• Build your confidence instead of dwelling on your shortcomings
• Conquer fear and take braver action in your career 

Let go of overthinking from Overcome Overthinking by Melody Wilding

When you sign up now, you get access to the course plus additional worksheets, templates, and more. 

Start the course now for free with LinkedIn Premium or sign up for just $24.99. 

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