Category: Leadership

Your Late-Night Work Emails Suck!

Maura Thomas may have said it more eloquently in her Harvard Business Review article, but the fact remains that your late-night work emails suck!

Of course it’s not just email – texts, instant messages, and the zillion other communication technologies can also be harmful.

It’s not necessarily “wrong” for someone to do work on a Saturday. Maybe a person has a flexible work schedule and Saturday happens to suits them, or maybe he or she is working to make up for personal time taken during regular work hours, or maybe something popped into their head and they want to address it.

Also, there are some circumstances where late-night, weekend or vacation communications demanding an immediate response are necessary, but ideally these are rare and truly necessary.

Be clear about expectations

It’s crucial that recipients of off-hours messages understand what the sender’s expectations are, especially if that person is their boss, or the CEO.

When the boss is working, the team feels like they should be working.

~Maura Thomas

If a quick response to an off-hours email you’re sending is needed, consider adding “RESPONSE NEEDED TODAY BY NOON” to the subject line.

If no response is required until the next regular workday morning, consider either delaying the email* until that time, or at least adding “NO RESPONSE NEEDED UNTIL MONDAY MORNING – ENJOY YOUR WEEKEND” to the subject line.

* Maura Thomas highlights a company that strongly discourages email between 10pm and 7am during the week, and all day on weekends:

If employees choose to work during off-hours, (the firm’s email system) discourages them from putting their habits onto others by sending emails during this time; they simply save the messages as drafts to be manually sent later, or they program their email client to automatically send the messages during work hours. This policy creates alignment between the stated belief that downtime is important, and the behaviors of the staff that contribute to the culture.


Off-hour communication is such an important aspect of work-life balance that at Enlightened Jobs, we ask companies posting jobs the (optional) question:

If the hiring manager sends a non-emergency email at 8am on Saturday morning and it would take 10 – 15 minutes to craft a response, what is the latest point in time it would be perfectly acceptable for the person in this role to respond?

We believe this gets right to the heart of a company’s culture.

Jason Fried, founder of the beloved web-based project management tool BaseCamp, announced a terrific feature built into their upcoming redesign called Work Can Wait:

“Each person in Basecamp 3 can set up their own work schedule with their own hours. You can of course choose to to receive notifications all the time, 24/7/365, no matter what..

screenshot from Basecamp's work can wait feature

Or, you can say Work Can Wait — only send me notifications during my work hours. Then you can set the start time and end time and also mark off which days you work…”

In closing, here are four more gems from Maura Thomas’s terrific article, “Your Late-Night Emails Are Hurting Your Team” (definitely worth a read):

Chaining your employees to the office 24/7 (via email, texting, instant messages, Slack, and on and on) isn’t good for you, your employees, or your company culture.


Being connected in off-hours during busy times is the sign of a high-performer. Never disconnecting is a sign of a workaholic.


The (often unconscious) belief that more work equals more success is difficult to overcome, but the truth is that this is neither beneficial nor sustainable. Long work hours actually decrease both productivity and engagement.


To deliver our best at work, we require downtime … But your employees can never disconnect when they’re always reaching for their devices to see if you’ve emailed.


Have a great day!

The Power of Loyalty

1-Sentence Summary: Money matters, but make sure to invest in becoming the kind of organization that will attract great talent.

Union Square Ventures‘ Fred Wilson is one of the best technology venture capitalist investors in the world, which means he pours millions of dollars into companies that (he hopes) are poised to take off like a rocket and grow and grow and grow.

He’s not seeking opportunities with a 10% annual return, or even 20%.

More like 5,000%.

That’s not a misprint – they were early investors in Twitter, back in 2007, when it was worth $35 million. Today it’s a public company worth almost $20 billion.

Venture capital is a risky, hit-driven business. The vast majority of firms he invests in will fail or flounder, resulting in a total loss of Wilson’s investment.

But the top one or two will (hopefully) be so wildly profitable that they overwhelm all the losing bets and deliver returns the vast majority of other investors* can only dream of.

*Most venture capital firms perform poorly, with the vast majority of profits flowing to a very tiny number of firms.

Great talent is rare and (with venture capital flowing freely), someone else is always willing to pay more. Talent is difficult and expensive to recruit, and right after they’re hired they have the luxury of switching companies for even more money.

Given this landscape, one might assume Wilson would advocate that firms he invests in hire mercenaries – pay top dollar for top people and drive them relentlessly, at all costs, in order to grow, grow, grow!

Instead, in his “Loyalists vs Mercenaries” blog post, he advocates that startup founders must build loyal teams.

This does not mean paying people less than their market value.

It means paying market value and creating a culture, mission and set of core values they believe in, and living up to them every single day (especially when it’s inconvenient).

In his words:

So what can you do to build a company full of loyalists instead of a company full of mercenaries?

First you must lead. If you think you are a good leader, get better. If you think you are a great leader, you can get better. Get coaching and focus on becoming the best leader you can be.

Second, build a mission driven company. Make sure you are doing something that matters. If all you are doing is trying to make money for yourself, then all your employees will try to do is make money for themselves.

Third, invest in values and culture. Matt Blumberg’s post is a good starting place for some tips on how to do that…

More of Wilson’s words on leadership: “At the end of the day, people are loyal to a leader they believe in. Leading is not managing… It is charisma, it is strength, it is communication, it is vision, it is listening, it is being there, it is calm, it is connecting, it is trust, faith, and belief. The best founders are great leaders.”

More of Wilson’s words on mission: “People are loyal to a mission (where) they believe in what they are working on and think it will make a difference in their lives and the lives of others. This is why investing in mission driven companies can produce great financial returns. Mission driven companies have something most companies don’t have. They have “why” that keeps the team together through difficult times…”

1-Sentence Summary: Money matters, but make sure to invest in becoming the kind of organization that will attract great talent.

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