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The Midnight Coaching Email

software managementLet me take you back to the year 2011.  This was a big year for us, as Susco had made a big name for itself as one of the first movers in mobile app development studios in the State of Louisiana.

We were growing revenue at 50% per year and collecting awards like they were going out of style.

At the time I was a babe at 33, not a grey haired 39 year old –  so needless to say, the success started going to my head. I thought of myself as being very emotionally intelligent with how I dealt with people, but it’s very easy when growing a company to do a great job focusing on the way you treat your clients and referral sources but not apply the same effort with your staff.  This blind-spot almost cost me one of my best employees at the time.  In the interest of protecting the innocent, I’ll refer to them as “Bob”.  So, here we go…

You know exactly what I’m talking about.  You’ve put the kids to bed and are trying to relax but you just can’t stop thinking about the “stupid mistake” Bob made that afternoon.

Maybe it wasn’t done the “right” way, OR it was done “right” but not fast enough, OR it was done the right way, fast but not logged in Salesforce!?!  Regardless, you’ve designed a process to stop this problem, you’ve coached Bob on it, and you’ve still got the problem rearing its head again.

So what to do now, O Brilliant Leader?  You write a professional email to the “offender”, CC a peer of theirs, and fire it off. Ahh, doesn’t that feel good?  Now you can go back to relaxing because YOU have fixed the problem, cracked the code, and enlightened your well-intended co-worker on their poor decision-making skills.

Congratulations, Siddhartha!  You nailed it.  Immediately you get an email back from Bob letting you know he has seen the error of his ways and, thanks to you, will now be a much better professional.  He also lets you know that he really appreciated getting that email and will have a great night’s sleep knowing that he works with people who care enough about him to provide constructive criticism at 10’o’clock at night.

Wait, I’m sorry, you didn’t get that kind of response?  Of course not.  Either…

  • You got a defensive email that kicked off the most demoralizing game of email volleyball ever, or
  • You had to have an hour-long conversation the next day with Bob: 50 minutes to cool the two of you down, 10 minutes to address the legitimate issue you wanted to talk about, or
  • Bob quietly agrees via email while, in reality, what loyalty he had left to you and the Company just silently died, or
  • You and Bob talk, you misunderstood the situation, and it wasn’t even something that could be coached in the first place.


This scenario happens to all of us, and there are several to be learned here:

  • Individual vs. Systemic Efficiency
  • Synchronous vs Asynchronous Communication
  • Emotional Intelligence


Individual vs. Systemic Efficiency

Yes, 10 minutes to bang out an email is less than 30 minutes for a conversation with Bob.  Less time for YOU.  Bob, however, is likely to spend more than an hour reading your response, trying to understand it, be upset about it, and then drafting the PERFECT counter-email. Processes that look efficient from a narrow perspective can turn out to be disastrously inefficient when looked at from a wide-angle, and you don’t have to look far to find examples.

Synchronous vs Asynchronous Communication

I get it, it’s 2017, we love our asynchronous, always-on tools like talk and text because they let us feel like we’re also always-on, always-productive. At the same time, we never want to negotiate with a potential business partner over email because we know we have a higher chance of winning the work if we talk about the proposal live and synchronous. Well, every day, we’re winning or losing our employees’ loyalty with our actions, so let’s use that wisdom and make sure we’re winning it.

Emotional Intelligence

There are five components to Emotional Intelligence: Self-Awareness, Self-Regulation, Social Skill, Empathy, and Motivation.  These components are practicable skills, not defined traits.   Of the five, three could have prevented this email bomb issue:

  • Self-regulation – Practice this muscle and you won’t need to send that late night email to relax.
  • Social skill – Understand that the late night email isn’t the right social lever to use on Bob and you’ll be more likely to leave it in the toolbox for when it is appropriate.
  • Empathy – If you can put yourself in Bob’s position and understand how it feels to be on the receiving end of that charming note, you’ll be much more likely to understand the blowback it can cause.

I write this to encourage you (and me!) to keep growing your Emotional Intelligence (your EQ).  The correlation between EQ and success is much stronger than the correlation between IQ and success, and–now the good news– EQ can be grown through diligence and practice!

Now, while you’re in the trenches putting theory into practice, the next time “the spirit compels you” to write that love note, email it to yourself instead, and handle it the following day in person (if needed!) like one Abe Lincoln.

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