Financial Poise
Overcome leadership doubt by wandering

Those Who Wander are Not Lost: Combating Leadership Doubt with New Perspective

How to Overcome Doubt with the Help of Your Team

Let’s face it. Even for the CEO of a closely held business, it’s not always apparent what the next steps should be or how to overcome doubt. But when you can find others who have been through the peaks and valleys, and who are willing to share their experiences, it should help you identify where you want to go and how to get there. Frankly, even if they have only been on part of the journey, they often still have useful insights.

There’s a lot that leaders struggle with internally and, hopefully, they don’t try to fix it all themselves. However, it’s very common for people to have doubts on what’s needed to continue on their leadership journey. Those who don’t have doubts are unlikely to make outstanding leaders.

So, as we’re transforming those doubts into motivation, there’s a great opportunity now for mentoring and elevating people who are emerging. Now would be an excellent time to establish coaching, ensuring that people who have goals can stay on track and not try to do it by themselves.

What About When The Leader Is The One With Doubts, Though?

As a leader, you may not open up to the person in the mailroom and ask him what he thinks. But for startups and entrepreneurs, leaders must lead by “wandering around.”

What does that mean? It means you need to go out there among your team and not only project the fact that you’re there to listen and encourage their success, but also to get a sense of the “real story” from those on the front lines. Unless you’re out wandering around in the office, conversing with other team members, you’re getting a filtered version of what’s happening instead of what’s real.

How to Overcome Doubt with One Simple Question

In one of my jobs, my unofficial title was: Director of “What Do You Think About That?”

For leaders, it is critical to ask “What do you think about that?” Why? Because, as you’re going up in an organization, your question-to-statement ratio also needs to go up. Being a leader can cause you to become more and more isolated from what’s actually going on, so you need to get out and talk to the people who are in the thick of things. That way, you can have a better sense of how to assess the situations and challenges your people and your organization are dealing with.

Now, you may have doubts yourself and the people who are on the frontline may have doubts, but that’s OK. It’s natural to have leadership doubts. However, as you talk through what the people on the front line are saying, know that they’re going to have a perspective that’s different than yours.

As a leader, you need to be comfortable enough to say, “You know what? You just brought up something that I hadn’t thought about.”

Catching Up with the Times

Here’s another X-Factor that you may not have considered: what if you get to a specific place as a company, in which you’ve reached Goals A, B and C…and times have completely changed? Perhaps they’re a bit more (or a lot more) irrelevant in today’s environment. With this in mind, you have the humility to admit you don’t know everything and are comfortable with saying, “What do you think?” far more often. It’s not limiting your influence, however. It becomes a very empowering and engaging way to interact with people.

OK, so you hadn’t thought about that idea of theirs. Is that really a bad thing or a weakness on your part? Of course not! It means you’ve got a strong team of creative, inventive and proactive thinkers who are encouraged to speak up. And that’s a credit back to you.

So go ahead. Take a walk out there. Wander. See what your team members and others are talking about in the work environment you’ve built. See what’s really on their minds. A natural conversation—not an inquisition or interrogation—is going to build trust and allow them to open up. It may take several times, but you’ll get there in building rapport. And in doing so, they’ll be more apt to volunteer new thoughts, ideas and information when you need it most.

[Editor’s Note: To learn more about this and related topics, you may want to attend the following webinars: What Every Founder/Entrepreneur Must Know and The Effective Director.]

©All Rights Reserved. July, 2020. DailyDAC™, LLC d/b/a/ Financial Poise™

About David Spitulnik

David Spitulnik is a successful executive with over 40 years of experience in both large technology companies and in consulting to and leadership of mid-market, closely held and family owned businesses across a variety of industries. In addition to serving as chair of the Private Directors Association’s Private and Family Business Center Outreach Committee, David…

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