Lessons from Churchill for team leads

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History will be kind to me for I intend to write it.” – Sir Winston Leonard Spencer-Churchill

And he did write a great account of himself in the journals of life before he passed away some decades ago.  His legacy would last forever.

I would love to draw upon a few tips and spice it with quotes all from the man himself. Leaders, entrepreneurs and startup co-founders today can learn a thing or two from the Greatest Briton of all time ( That is according to a poll done in 2002 )

He is also the one to have led the UK during one of its most turbulent times in history. Every nation needs someone like that. And when the moment came, he was the one called to the task.

1. Be uncompromising

In standing your ground, you’ll make enemies.

You have enemies? Good. It means you’ve stood up for something, sometime in your life.”– Sir Winston Churchill

Soldier on and do what you believe is best. Still be ready to take criticism and change if what you are trying to do does not work out.

Be strong. Sometimes you have to go with the better long term goal than the immediate short term gratifying one. It might have been easier to make certain compromises.

To build may have to be the slow and laborious task of years. To destroy can be the thoughtless act of a single day.” – Sir Winston Churchill

He built up not only the moral of the British people but also the resistance of the army in hard times.

And the reason they kept moving, was they had a leader of unshakable belief and conviction.

2. Keep adapting

He said it best.

To improve is to change, so to be perfect is to change often.” – Sir Winston Churchill

You might never reach the end of perfection, just like the Sire says. He, himself wasn’t all perfect. Its said he spoke with a stutter. One of the best public speakers ever spoke with a stutter. That is the irony of life.

Still he become one of the best speakers ever.

He is fondly remembered for the “I have nothing to offer but blood, toil, tears and sweat speech.

In inspiring the British, he also said these words which will forever live in memory of all Britons.

…we shall fight in France, we shall fight on the seas and oceans, we shall fight with growing confidence and growing strength in the air, we shall defend our island, whatever the cost may be, we shall fight on the beaches, we shall fight on the landing grounds, we shall fight in the fields and in the streets, we shall fight in the hills; we shall never surrender”

Anyone can talk when things are going well. Imagine being able to inspire your troops when things are tough, that’s hard.

Every day you may make progress. Every step may be fruitful. Yet there will stretch out before you an ever-lengthening, ever-ascending, ever-improving path. You know you will never get to the end of the journey. But this, so far from discouraging, only adds to the joy and glory of the climb.”-Sir Winston Churchill

3. You would fail

You would have failures in life and business. In short there would be times of crisis.

a. How you deal with it ?

b. Why you choose to put up with the situation ?

The second question, is an even greater question. If your why and how are good enough, you will do just fine.

Sir Winston Churchill’s intellect was hard-won wisdom. Its seen in the quote.

Success is the ability to go from one failure to another with no loss of enthusiasm.” – Sir Winston Churchill

He failed several several times in life.

1915- He was blamed for the disastrous effort to seize the Dardanelles straight during World War I, and was demoted and disgraced

1922 – He was again disgraced following the Chanak crisis and lost election

1936 – His support for Edward VIII during the abdication crisis greatly damaged his popularity

Sir Winston Churchill confessed to a friend, “My political career is finished.”

Building a successful startup is hard work. Its more probable you would fail than you would succeed.

You would have failures. Missed delayed. Dissatisfied clients. Co-founder troubles. That feels like startup hell.

If you’re going through hell, keep going.” – Sir Winston Churchill

Keep the faith. Things have to turn around soon. That parachute has to open. And it will.

When you fail and your enemies talk, remember this quote;

When the eagles are silent, the parrots begin to jabber.”– Sir Winston Churchill

Be the eagle. Take the higher ground. Let your work do the talking.

Failure can strengthen, rather than destroy, yourself and your team. So be happy when you have failed. And learn from it. ( unless you are dumb enough to make the mistake a second time )

4. Cut negativity out:

Every man should ask himself each day whether he is not too readily accepting negative solutions.”– Sir Winston Churchill

Look on the bright side of every circumstance. I am not saying be ignorant of the situation. Just don’t let them cripple you. Stand strong and pick up the best bits from every situation.

….then be ready to sell a dream:

Essentially, just be able to motivate your troops like no one else can. After all you know your team best. His speeches and radio broadcasts helped inspire British resistance, especially during the difficult days when the British Commonwealth and Empire stood almost alone in its active opposition to Adolf Hitler.

Startup success is not a one time thing. Its continuous deliberate effort. Just like victory for the Allied forces.

Continuous effort – not strength or intelligence – is the key to unlocking our potential.”-Sir Winston Churchill

5. Be ready to lead:

When he knew he was to be prime minister, he wrote:

I was conscious of a profound sense of relief. At last I had authority to give directions over the whole scene. I felt as if I were walking with destiny, and that all my past life had been but a preparation for this hour and for this trial. . . . I was sure I would not fail. Therefore, although impatient for the morning, I slept soundly and had not need for cheering dreams. Facts are better than dreams. – Sir Winston Churchill


Your team would look to you for answers, and for leadership. They don’t have it, else they won’t come to you. Be ready to lead, advice, and kick them in the behind if necessary.

Being a leader of a growing company is not easy. Be ready to take the hits from board members and go back to your team with a smile. Ever ready to lead them on.

6. Apply everything you know

Bring all your skills to bear. Sir Winston Churchill was a soldier, journalist, prolific author, politician and statesman. With all of these talents and experiences they were amplified and reflected in his leadership of the nation.

Startup entrepreneurs have experiences of their own. Bring this into your company. Whether through its culture or work ethic. Influence your team by the experiences you have personally been through. Don’t compartmentalize them.

I will leave you with one of his most inspiring quotes.

We shall not fail or falter. We shall not weaken or tire. Neither the sudden shock of battle nor the long-drawn trials of vigilance and exertion will wear us down. Give us the tools and we will finish the job.”-Sir Winston Churchill

By that sentence, I have finished my job here. That being to encourage you using the words of Sir Winston Leonard Spencer-Churchill.

Now go do yours.

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