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Tuesday 2¢: Sometimes When You Lose, You Really Win

Despite the Word Cup, the title is not a reference to football, but a monologue from Rosie Perez in White Man Can’t Jump, when she says: “Sometimes when you lose, you really win”, as I recieve a good outreach email.


Sometimes when you win, you really lose, and sometimes when you lose, you really win, and sometimes when you win or lose, you actually tie, and sometimes when you tie, you actually win or lose. Winning or losing is all one organic mechanism, from which one extracts what one needs.

Gloria Clemente (Rosie Perez) / White Men Can’t Jump

Like you, I get a fair number of unsolicited emails, maybe you call it junk or spam, but the stuff from folks that are interested in flogging me something.

I’m not going to use this post to highlight some of the obvious stuff we all see in these emails. I or {firstname} rarely need the service or product being hawked, and I’ve even had emails so far off that they are written in languages I don’t speak (recently Dutch or French).

However, from time to time, when it’s clear someone has made an effort, or if I feel that I can help someone by pointing out where their email has gone wrong, I reply to these emails. After all, I am a B2B marketer, so I am in the same game.

Maybe shockingly, for a bunch of folks that normally love to fill up my inbox, I only sometimes get a reply. However, this Tuesday 2¢ is inspired by one of these interactions, when I did get a response.

So, I get an email from someone at a vendor offering me something.

I’m not the right person, and I wrote back and explained why I was not the prospect they were looking for.

Do you know how hard it was not to write “droid” in that sentence?

If you are wondering, of all the unsolicited emails I get, I replied to this one because the email was well-researched. He referred to something in my podcast, something that you’d need to have listened to know, not just some reference in the title or show notes. 

So, I guess the “give to get” psychology kicked in; something in my deep brain felt indebted to this poor chap that had given his time to listen to, whatever it is you’d describe my f’in’ podcast as, and… well… the least I could do was to give something back and reply.

Once he understood I was the wrong person, he didn’t just move on to someone else and ignore my feedback but replied. He appreciated my reply, but explained he was a new account manager, new to the market, was seeing a slowdown in his pipeline and asked for my advice. 

He asked:

  • What trends do I see that might be causing his pipeline slowdown?
  • What would make me (as a CMO) buy something?

BTW – that second question was not what would make me buy the thing he was selling, but I read it as a a more general and, I think, more interesting question of what is motivating CMOs to purchase today.

I intended this 2¢ to be my reply, answering his questions as I think this is an interesting topic. I’ll explore this another day, but it is so easy for us to lambast bad sales emails (like in this post that I wrote recently), so I thought I’d share a positive story.

Sure, the targeting was a tiny bit off, I’m not the buyer, but he put in the work, and his miss was more down to the specific nature of my role in the organisation than his research, and there is nothing that could have told him that before he reached out – it was an easy mistake.

Perhaps, if one is super cynical, this is all some kind of Jedi mind trick, the last tom foolery in the business development arsenal, but to me, he came across as a genuine, someone who had done some research and was interested in doing better.

(Unlike the email from someone that thinks I speak French, another who thinks that I am in a role that hires developers or that as a “cyber security vendor, we need to stand out” (not one of those)- a simple glance at LinkedIn would have solved this.)

His email stood out, with its “give to get”, it earned trust as he demonstrated authenticity.

It also got me to act, I replied (oh and I also alerted the right person in the team to the offer)

At the very least, at this point, he has garnered awareness and engagement, even if not a deal. 

And maybe you’d be less inclined to engage more once you’d shared a polite no and would find his follow-up questions annoying, maybe on a different day I would.

But, from his perspective, imagine if this chap asked these questions every time someone replied with a “no”, and 10% of people replied, or maybe just 2 or 3 people.

  • What trends are you seeing?
  • What would make you buy something?

What insight would he gain? 

He would win something from a “no thanks” and the rejection. He’d get some insight into his market, sharpen his approach and maybe his improved email game would get a meeting and maybe a deal.

Then imagine if gathering this type of inteligence, maybe not these exact questions were part of your front line sales peoples remit.

As Gloria/Rosie said:

Winning or losing is all one organic mechanism from which one extracts what one needs.

(If you are reading this, Monty – nice work, I will reply)


This artwork was created using A.I. through NightCafe Creator I thought it would make a change from pictures of me 🙂