How to lead when you are lost

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When I was in my late 30s, I was living a happy urban lifestyle.

I was lobbying in Washington, D.C. for a large private company. My husband was rising in his career with the federal government. And we had a new daughter.

Then a phone call came.

Not tragic news (thankfully), but a job offer in the Midwest.

As often happens with career moves, a single phone call separates you from your peaceful state of life to an unknown and disruptive, yet exciting new chapter.

In this case, the call was from a senior executive I knew well. We were at the same company and I was part of his team that was tasked with merging one of the company’s existing businesses with another publicly traded company. His ask? Join his management team once the new company was launched.

To be on the executive team of a soon-to-be new Fortune 500 company in my late 30s? How could I say no?

To be sure, the opportunity was certain to create disruption. My husband’s career would be derailed. We had a young daughter. And, I was in the middle of infertility treatments, hoping to conceive a second child.

Yet, I knew if I turned down the offer, I would regret the decision. I also knew that moving to the Midwest had other benefits, including living closer to our families and giving our daughter a chance to know her grandparents and cousins.

So I said yes.

Within a few months, we sold our house, packed up our belongings and made the 1,000 mile trek to Minnesota. By this time, I was a few weeks pregnant, in the midst of resettling our family and becoming acclimated in a rapidly changing company.

During those initial weeks and months, I had a pit in my stomach.

I had countless “holy crap” moments when I was trying to create and lead my new global team, but wasn’t exactly sure where I was going.

Quite frankly, I don’t think any of us executives on the management team knew exactly where we were going as we worked to combine two very different company cultures, make two former competitors work together and rapidly learn the ropes of public company life.

Years later when I left the company and shifted to the startup world, those holy crap “where am I going?” moments resurfaced. They also resurfaced when my father was diagnosed with Stage 4 cancer, my husband and I were changing jobs, and other obstacles were thrown in our life’s path.

What about you?

Think for a moment — whether in your personal or professional life — when you’ve had to lead.

It might have been a professional experience, such as starting a new job, managing a new project or even getting fired and being forced to find a new job.

It might have been a personal experience, such as helping your aging parents, navigating through a divorce or raising a child.

Did you always know where you were going?

Did you, too, have that pit in your stomach and feel completely lost?

The irony is that as I stumbled my way through various leadership roles, often in murky and uncharted territory, I accumulated valuable new skills and tools that better equipped me for the next time I was leading, but lacked clarity.

The tools I’ll share below are divided into two areas: the internal game and the external game. I learned that you have to look inside yourself first to gain strength and align your inner compass before tackling your external environment.

I’m confident these same tools will help you, too. Not just to guide you, but to give you confidence to navigate and even relish in the unknown.

The Internal Game

Know thyself

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Take a good hard look in the mirror.

Assess yourself first.

Ask, “What do I do well?”

Think about your passions, the experiences that make your heart skip and excite you.

Think about the compliments you’ve received. What have other people, whether your family members, spouse, friends or work colleagues remarked on that you’ve done well? Even think back to your childhood and what your teachers or parents told you.

Conversely, where do you struggle? What saps your energy or drains you? Where have you been coached? When you’ve been criticized, in what areas are you receiving the feedback?

The reason you need to assess these questions is that when you enter the unknown terrain, you need to understand the strengths you bring and where you are vulnerable.

When I started my new executive role, I knew I had the energy and vision for my new job and a strong passion for the industry. I also knew I was a hard driver.

But, I had gaps, too. I had little knowledge about serving on an executive team. And, I knew that my strong focus on execution also created a challenge for others because of my fast pace and quick decision making.

Your own personality and skills are not static. That’s why it’s important to periodically take stock of who you are and what you’re bringing to the role. And, it’s absolutely critical when you are thrust into a leadership position and don’t know where to go.

Go together

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There is an old African proverb that states, if “You want to go fast, go alone. But if you want to go far, go together.”

In other words, don’t fly solo.

Having others at your side or on your team helps you see things differently and gives you an opportunity for sharing ideas, tackling tough issues and even commiserating.

Look at your teammates or peers as your safety net. You have each other’s backs, even if you don’t always agree or see the path ahead differently.

If you don’t have the resources at work or home to “staff up,” form an informal team of advisors that can provide candid feedback and ideas. Find colleagues, friends or peers in your profession who can guide you or give you advice.

I’m a builder by nature so after several years at the Minnesota company, I left in pursuit of another early stage organization. I was recruited to serve as a CEO of a small penny stock startup.

Despite assurances from the founder that I could redesign the Board of Directors and have access to resources, I quickly learned there was neither the desire nor the funds to make good on the founder’s promise.

I knew leading the startup with only minimal resources and few teammates who had the skills to reshape and grow the company would only drive the company into worse shape. I left after six months and vowed never to lead alone again.

Uncover your inner moxie

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The topics of grit and resilience have been popular ones for recent years, especially for school-aged children. And all for good reason. Grit is the resolve or strength of character that gets us through tough situations.

But, when you’re not certain what’s around the corner and you’re in charge, I want you to think beyond just grit and resilience.

You need to uncover your inner moxie.

What is moxie?

Moxie is boldness in the face of uncertainty.

It’s facing an issue head on and not regretting your actions later. Moxie is the nerve to ask hard questions and make tough choices.

So often we hear that little voice inside of us giving us uncertainty and casting a seed of doubt or fear. Moxie is stepping beyond that fear and just doing what you think is right — and not second guessing yourself later.

I had to find my inner moxie when I decided to leave the Minnesota company I was so excited to join seven years earlier.

I felt, among many things, that the company’s evolving culture was no longer a good match for my leadership style. It would have been far easier to maintain the status quo and stay. But, I knew that wasn’t right, for me or the organization.

I resigned without a new job in hand, but learned that a bold move and bit of moxie can be life changing, even if I had fear and uncertainty about the future.

Not all who wander are lost

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This well-known phrase from J.R.R. Tolkien’s poem, “All That is Gold Does Not Glitter” (also known as the “Song of Aragorn”) in the Lord of the Rings reminds us to think about the importance of the journey.

When you don’t know exactly where you’re going, view the unknown and being forced to wander as an invitation to search and discover.

Lack of clarity forces you to look harder to find answers.

But, the key is to stay in motion and embrace “methodical wandering.” In other words, keep looking, searching and seeking. Do not be overcome by inertia.

As my business partners and I have developed our Midwest agriculture startup, we’ve had countless moments of wondering and wandering: how big is the market, what is the size of the plant, who should we partner with?
Those days of wandering and feeling uncertain have been excruciating. And there are times when we simply wanted to suspend the indecision and just decide.

The silver lining?

Our wandering forced us to seek input from all types of resources, including calling others in the industry, looking at our competitors’ strategies, seeking input from our investors, talking to marketing consultants and interviewing numerous global engineering companies to assess their capabilities.

In other words, methodical wandering — constantly searching and seeking answers — ultimately led us down the right path.

The External Game

Once you’ve bolstered your internal and mental strength, you need to look beyond yourself and assess the broader environment in which you are leading. These tools can help:

Take a wide angle lens view

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In 2017, after the tragic shootings at a Las Vegas country music festival that left 59 people dead, a security guard was asked by a national journalist how people could best be protected from such a tragedy occurring again.

The security guard acknowledged the impossibility of protecting every person.

Instead, he stressed the importance of constantly being aware of your own surroundings and being mindful of where you are, who is near you and whether you can safely exit your environment or situation.

In essence, he was saying, taking a wide angle lens view.

Looking far and wide, regardless of where you are at or who you are leading, requires you to to assess all of your external data and information about your environment.

There are so many times when you will find yourself in a new situation, ill equipped with adequate information, accurate facts, or even third party opinion.

From a personal perspective, when my daughter started high school a couple years ago, I felt like we had entered a new ecosystem.

Not enough parent orientations or information from the school could prepare my husband and me for the reality of the academics, social dynamics and substance abuse at her college prep high school.

Feeling like a (very) naïve new parent, I combed through the family directory, identified names of parents with older students who I knew would be candid, and asked them to give me feedback on their journey.

I then started searching blogs, online resources and contacted friends outside of our region to figure out the new landscape and what “normal” meant for these teenagers. Their feedback helped me ask smarter questions at parent meetings or conferences.

I’m sure there are days when I’m still naïve, but the view of what others experienced and what research has shown has helped me understand the reality of this new environment.

Keep your goals simple

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Rome was not built in a day, but as the saying goes, they were laying bricks every hour.

Little in life is accomplished overnight.

Whether starting a business, learning a new skill or developing a new habit, the process is often accomplished in small, iterative steps.

Don’t boil the ocean.

Set one goal and accomplish it. Then set the next goal. When you are leading in the unknown, remember accomplishing one small specific objective is better than a wildly audacious goal that you never reach.

When my business partners and I completed our first seed capital offering, raising nearly $5 million, we realized that without environmental permits, we wouldn’t have a project to launch.

While obtaining air and water permits for a $200 million project is no small feat, we made that our single goal, focusing on the mantra of “no permits, no project.” We worked relentlessly for months on the permitting process and managed to successfully secure our key permits.

We also wanted to plan for the worst. Should the project not proceed for any reason after the permits were obtained, at least a fully permitted site would have more value and could be monetized for the investors. But, regardless, we never deviated from the goal.

Growth is not a straight line

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Several years ago, I was listening to a competitor’s quarterly earnings call with investors. Analysts were challenging the CEO on the conference call about the performance of one of his businesses.

Finally having had enough, the CEO snapped back and said that while he had told the analysts his business would grow, he never promised it would grow in a straight line.

What a lesson on life, even if the CEO was only talking about his business.

Growth doesn’t happen in a straight line, and more importantly setbacks and dips in the line are actually when you learn the most.

When leading in the unknown, recognize that dips are inevitable. However, embrace the opportunity to learn from each setback.

From my own career perspective, I’ve learned that growth happened most during transitions and setbacks.

I’ve had periods of great stability: staying at two companies for over 17 years. And, I’ve had periods of instability: an 18-month consulting gig, leading a startup for a short six months and ultimately co-founding another startup.

When I walked out of the publicly traded company I helped launch, I felt like I hit rock bottom. Little did I know that my upcoming period of exploration would lead me to what I do best — starting new things from scratch.

When I dipped again at the small penny stock startup, walking out cemented my views that my next role would be all about finding the right leadership team.

And when I joined my two business partners to develop our Midwest startup, I learned that the dips had positioned me to find the right role — being part of a three-person leadership team that took risks and was willing to set bold goals.

Give gratitude, give back

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Leading through the unknown can be lonely and unsettling.

But, wallowing in your self pity doesn’t help. If you are tempted to go there, focus on someone else who might need more help than you do.

What has kept me grounded is finding time each day to give gratitude. Even after a day full of frustration, I try to find a few minutes to give thanks for what has gone well, whether a returned phone call from a prospective investor, a finished load of laundry, or even a sunny day.

The shift of thinking “what has gone right” versus “why did so much go wrong” sets me straight and ready for another day.

Giving back keeps you grounded.

I’m not talking about large philanthropic gifts to charitable organizations, though those are amazing too. Rather, I’m talking about the simple things like providing a good networking contact to a friend in need of a job, providing insight to someone who is experiencing their own business struggle, or volunteering an hour or two for a cause you care about.

Even if your leadership journey lacks clarity, I can assure you that you will always find clarity in saying thank you and helping others.

Leading when you are lost is not easy, nor is it impossible. Know that inside of you and with the help of others you have a good deal of tools that equip you to figure out the path ahead.

The journey may not be a straight or an even path, but I assure you there’s a lot to learn, relish and celebrate about being lost. Especially once you reach your destination.




Entrepreneur || Fortune 500 Executive

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Linda Thrasher

Linda Thrasher

Entrepreneur || Fortune 500 Executive

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