A Sales Lesson I Learned The Hard Way

I felt instantly sick when reading the email from my boss on an unassuming Wednesday afternoon.

“Tom, this is really bad but we’re going to learn from this. If you’re cool with it, I’m going to highlight this to the entire team as a message that we all need to strike while the iron is hot.”

“That’s cool”, I said, while using every bit of energy I had to force my ego aside.  

Things had been going so well before that. In 9 short months after starting work for the company, I got an opportunity to take on a larger territory and move across the country. There was a bright future ahead and I was fired up.

But the game was moving so quickly.  

You know how they say that the difference between professional and college sports is the “speed of the game” and that some kids just can’t handle it?  

That’s what it felt like. My quota had virtually tripled overnight and my personal organization was out of sorts. I was overwhelmed and not performing at a high level. I was out of sync.

So what spurred this email exchange?

My boss and I had gone on what we thought was a great meeting with a prospect.  We built a strong rapport, identified a need that we could capably help solve and had clearly defined next steps.  I was to follow-up with the action items that afternoon via email.

But I didn’t send the action items that afternoon.  Or the next day. Or the day after that.

It took me 5 business days.

As a proud salesperson, it makes me sick to even admit that.  

By the time that I got back in touch with the prospect, they said they were contacted by 11 other vendors in that time period. 11 vendors that were performing at a higher level than I was.


Spoiler alert: We didn’t win this deal.  Well, we eventually did but it took me another 18 months and many hours of hard work to finally get them on board.

Moral of the story:  Strike while the iron is freaking hot!

But what does that mean exactly?

In the literal sense, it means to strike a hot piece of iron, with a mallet or other tool before it cools.  You need to do so while it is still hot enough to be shaped.

In the figurative sense, it means to act on an opportunity promptly while favorable conditions exist; to avoid waiting.

In other words, it means to prioritize and execute.

Everyone has the same 24 hours but you need to get the most important tasks done first.

If there is a deal on the line or a problem with a customer, solve that first.

Updating Salesforce can wait.  Tweeting can wait.

Have a sense of urgency.

If you don’t know the answer or have all of the information, get back to them quickly and let them know that you’re working on the solution for them.

Give them a deadline for your follow-up and consistently beat that deadline every time.

I think you can pretty accurately tell the health of a deal based on 1) how clearly defined the next steps are and 2) how effectively you have been in the follow-up process.

Look, I’m not on my pedestal saying that I perfectly follow-up every single time – far from it.  I’m also not saying that you’ll win every deal that you follow-up quickly on.

But sales (and life) is all about stacking the deck in your favor and putting yourself in position to win.   

Sometimes it takes a little public negative recognition to really solidify a point. I’m so glad that my boss told this story to the whole team (with my permission) because it stuck in my mind so deep that I wouldn’t let that happen again.

It’s one of the best things that’s happened to me in sales.  

Prioritize what’s important and execute against it.  

Strike while the iron’s hot.

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