Are Too Many What-Ifs Dragging You Down at Work?

When a new, radical solution to a problem surfaces, most people approach it one of two ways. Some feel wary: What if something goes wrong? What if someone doesn’t like it? Others feel optimistic: What if we exceed expectations? Consider Elon Musk when he asks, “What if humans could live on Mars?”

In both scenarios, there’s a what-if. But in the former, fear is the driver. It’s about playing it safe — keeping the status quo. Sometimes, that’s good! Sometimes, there are real reasons to say “no” to a solution or alter your course. Other times, however, it only inhibits growth.

When Fear Gets the Best of You

Once, I was working with a company’s owners to bring employees together as a team to boost engagement and profitability. The majority owner met every one of my ideas with a positive “why not?” This yielded stronger teamwork and a renewed commitment to the work among employees.

But the other owner was cautious about relinquishing control, which inhibited the teamwork we strived for. He tended to micromanage: refusing to follow new work processes designed by the employees, assuming lower-level employees didn’t have much to contribute, and keeping employees from taking charge of their roles. He was essentially asking: “What if I give up control and something goes wrong?”

In the end, I watched his what-ifs drain the enthusiasm — and ultimately the commitment to the culture change. He didn’t hold his employees accountable for implementing changes, and this sabotaged organizational improvements. Employees became disengaged once more. Acting from fear not only prevents you from thinking outside the box; it makes your box even smaller, and your business and employees suffer for it.

Gallup reports that leaders who lack confidence start to micromanage instead of delegate and coach. This is negative what-if thinking, which leads to less innovation and fewer problems solved. A leader who leans toward the why-nots or positive what-ifs, on the other hand, is more likely to create a culture of innovation.

Making Your What-Ifs Count

In my experience coaching women, I’ve found it’s not uncommon for us to take fewer risks in our decision-making because we allow fear of the unknown (i.e., all the things that could potentially go wrong) to get in our way. Though caution has its place, those fearful what-ifs can creep up and prevent your company from reaching its true potential.

Below are five strategies I use to help my clients ensure their what-ifs are constructive, not obstructive:

1. Check yourself and your mindset. When a negative what-if creeps up, there’s often an assumption lurking behind it. I once worked with a department leader who would automatically respond to any new idea with: “We can’t do that!” Why? He thought his boss wouldn’t like the idea. My response? “You’re the leader! Do you really need approval?” He didn’t. But he assumed he did and almost didn’t move forward because of it. Take a moment to think whether your so-called roadblocks are truly there.

2. Work on your fear factor. If you build up your confidence overall, facing the unknown with positivity will feel more natural. One time, I coached a woman who broke into tears when asked to speak during a break-out session at a conference. But after months of intentionally stepping out of her comfort zone, she met the next speaking request with a “why not?” Now, she’s set her sights on becoming a main speaker. If you feel stronger about yourself and practice facing what scares you, less will inhibit your growth.

3. Learn from your own history. When you let fear drive your decisions, you’re allowing things (that are unlikely to happen) to slow you down. I have clients write down the what-ifs holding them back on a decision. Later, we review them to see if those what-ifs actually played out — and it’s very rare that they have. Creating your personal history of successes (and the fears that never came true) is a powerful way to demonstrate how useless those negative what-ifs really are.

4. Prune your people. Trees bear fruit based on the nutrients they’re fed. As Dr. Greg Holliday — a psychologist and colleague of mine — says, “You want to surround yourself with facilitators.” Associate with people who ask the positive what-ifs (facilitators) and look for ways to dismantle barriers to action, rather than those who prefer to focus on the negative what-ifs without providing a solution.

5. Make positive what-if conversations the norm. The why-nots and positive what-ifs should become a habit. Set aside time regularly to think through suggestions for achieving your business’s strategy and the forward-thinking what-ifs associated with them. You’ll make positive, constructive thinking a part of your everyday work.

The unknown can seem intimidating, but don’t let fear destroy your company’s potential to succeed — too many negative what-ifs will only bog you down. Be mindful about how you treat new obstacles and solutions, and challenge yourself by wondering what could go right, not what could go wrong. You’ll find it’s a lot more productive (and fun!) to lead with a why-not mentality.

Loriana Sekarski is founder and president of BONSAI, a consulting company that transforms leaders (and businesses) into the best versions of themselves. As a leadership coach, Loriana teaches leaders how to hone soft skills, spur workplace engagement, and achieve untapped levels of potential. Outside of BONSAI, Loriana serves as an adjunct professor at Washington University in St. Louis’ graduate student program. Additionally, she’s fine-tuning her passion project, TakeFlight, a program that addresses domestic abuse within the Christian community.


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