4 mistakes, 4 lessons and how those made me into a better leader

Ilana Golan
Female Founders
Published in
5 min readSep 14, 2015

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“You should have done it differently”, I said with confidence.

“Lift the plane to 45 degrees and only then turn to make it to the target”

I was about 20 years old.

Proud of being chosen to be an F-16 flight instructor, I thought I knew everything.

No…

I was sure I knew everything.

I was giving a brief to an F-16 pilot twice my age after training him in the simulator on air-to-ground combat. When I finished the brief, the pilot looked at me calmly, smiled and said “Honey, do you know who I am?”

We all have stories about what we did well and where we failed.

Its important to take some time and analyze the good and the bad so we learn from each situation and improve as people and leaders.

Here are my 4 most memorable lessons.

1. Know your audience

I looked puzzled at the pilot sitting in front of me.

I knew his name but was I supposed to know more than that?

He was obviously somewhat annoyed I didn’t. Then he took a step forward and said “I destroyed the Iraqi nuclear plant in 1981 when you were about 6 years old.”

I knew exactly what he was talking about — the destruction of this plant was one of the most famous and dangerous long range attack mission in Israeli Air Force history.

How did I miss that???

Obviously this guy knew how to do air-to-ground attacks in his sleep.

Initially I was shocked and hurt by how he talked to and treated me, thinking to myself “even experts make mistakes and that’s why I am here… to remind and train them on the basics”.

It took me a few weeks to understand what I did so wrong.

I didn’t bother to take the time to learn who I was talking to and I thought one teaching approach could fit all.

Boy was I wrong.

That slap in the face is still one of the best lessons I’ve ever learned.

Always understand who you are talking to and always tailor your discussion to the person in front of you. The same message can be communicated in so many ways... which way is right for your audience?

Whether it’s a 1*1 or presentation in a large conference — learn your audience and choose your words and tone accordingly. If I started with a compliment, showing I knew a bit about the pilot, and then continued with some questions about what he would do different in this training — this conversation would have gone completely different… he’d have been much more receptive to feedback.

That’s true for every aspect of life and to everyone you’ll talk to, big and small.

2. Assumption is the mother of all fuckups

We just came back from a very important customer evaluation for our product. Business with this customer was extremely important for our startup and could really make things happen for us. We had to make it work.

Their requirements seemed totally simple and our demo clearly showed we are on top of it.

We cheered all the way back to the office, certainly we had won the business.

A week passed…

No news is good news, right?

WRONG!

No news may be horrible news in business.

I was worried.

Eventually we got a hold of them and found out they were actually evaluating another vendor and mentioned they like what they saw with our competitor. OH!

We immediately worked to win the account back but assumption almost killed this deal for us.

Don’t assume.

When you don’t hear from someone — find an excuse to ping them again.

In every aspect of business, think about what could go wrong and what’s your plan in each situation. Don’t let it scare you but just know that you have a plan and you won’t be caught off guard.

3. Trust your instincts

It had been four months and I was still interviewing candidates for the sales engineering role. How could it be so hard to find great people?

Pressure was high.

We were entering Q4 with less staff than we needed.

How could we make the numbers?

The sales team was stressed, the executives were stressed and I wasn’t delivering. I just couldn’t find good enough people for my growing technical team.

Eventually I interviewed someone… OK… not great but not a disaster either.

My gut feeling said that he is absolutely not the right person but… the pressure… I just can’t say another no just because my instincts say he isn’t right. After all, he did OK.

We hired him. We trained him and invested precious time to give him all the tools he needed to succeed. Swallowed our tongue when he was embarrassing us in-front of a customer and tried showing the much needed patience for our new hire.

After 6 months we knew it was a disaster and after a year got rid of him. These things always take longer than they should.

Trust your instincts.

Whether its in hiring, communication with customers or analyzing whats going on in your team.

Back it with data whenever possible but your instincts are very important input.

4. Ask Ask Ask

My manager hung up the conference phone.

“Wow I am glad you understood what they were saying, because I totally didn’t get it”. I said shamefully.

I was still a student in my internship trying to drink from a fire-hose of information. I felt too new to ask questions in that form and decided to ask my manager privately after.

“You did understand what they want, right? Because we need to deliver it next week”. I asked worried.

He didn’t.

Only then I realized that if I don’t understand, there is a good chance others don’t get it either but some simply don’t ask. Why are they afraid to ask?

Too many people think that if they ask a question they seem weak. They nod even when they have no clue what someone is saying. They don’t like admitting to their team that they need clarification.

It’s the opposite.

Ask so you become smarter and deliver better.

Sit with each person on your team to see what they are doing. Learn from them.

Sit with your customers to understand how they work and what they need.

Never be ashamed to ask “Why” or “Can you explain this again’?”

You don’t need to be the smartest in the room, but you need good understanding of the system to lead it well and make smart decisions.

What are your top lessons?

If you liked my story please recommend to others and share your experiences.

You can also read:

7 reasons why every woman should travel solo to become a better leader

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Ilana Golan
Female Founders

Serial Entrepreneur & Keynote Speaker. Engineer and F-16 flight instructor. Ironman, Mountaineer and world traveler. https://www.leapacademy.com/