Here’s a great example of a question a boss should ask

I think we all kinda sorta know these things (hopefully):

This isn’t universally true, no. But I’d say it’s true in more cases than not. Most managers aren’t good at communicating, usually because they have their eye on whatever can benefit them (some KPI). Communication drops in the process, no one on the team knows what is expected of them, and work becomes overly challenging. What I just described is actually normative for a lot of people, unfortunately.

But managers aren’t getting better. 82 percent of them are the wrong hire. Globally, about 15 percent of people feel “engaged” in their job. You can argue with what “engagement” means, yes. But 15 percent is terrible. A lot of that is because their direct manager is terrible. This isn’t rocket science.

Why aren’t managers getting better? Lots of reasons, with No. 1 being “No one cares if a manager is people-effective so long as they’re product-effective.” Organizations don’t really care about people. They care about making money and the top people care about perks. That’s the basic deal. Managers are cogs in the middle. Some might rise up and get minted, but most don’t/won’t. That’s the game. If you pretend it isn’t the game, you’re just lying to yourself.

One of the other reasons is that training tends to be bad. We actually train people to be managers — train conductors and spreadsheet jockeys — instead of training them to be leaders. Fundamental flaw but “That’s how we’ve always done it!”

A lot of managers, I’d reckon, have never really been trained on how to have a conversation. You’d hope people don’t need to be trained on this, but many people do.

What if we could give managers some actionable advice on what to do?

Now we can!

The question to ask

Long, good article here about a lady who manages hundreds at NerdWallet. It’s mostly about asking better questions and rising up to meet challenges. Long, good, and detailed. Read it if that stuff interests you.

One of the main questions she asks is this simple but beautiful gem:

What’s currently harder than it should be?

She notes:

People will trust if they believe their managers genuinely care and want to help. “It’s our job to care. That’s how we help people do their best work and grow. That makes them more valuable to our company and in the job market. That’s a fair trade.”

Wow. I just openly wept.

Here’s what most managers do around this stress situation, for example:

  • “I know you’ve been stressed. Hang in there!” (no attempt to solve the problem)
  • “Are you feeling stressed?” (obvious yes and kinda trying to coax out a specific answer)
  • “We’ll get through the busy season! Keep grinding!” (then next season will get busy; also no attempt to help)
  • “What can I do to help?” (a good Q but often with no follow-through)

Now look above. If you ask “what’s currently harder than it should be,” here’s what you could learn:

  • Who is legitimately stressed
  • What processes are holding back productivity
  • A few things that could immediately change

Isn’t this better than vague bullshit about how “we’re all putting in the work together?”

Why don’t more managers do this, then?

Partial list:

  • Don’t know
  • Don’t care
  • Not tied to their incentives
  • Overwhelmed with their own responsibilities
  • Only got direct reports to make a higher salary and desperately try to avoid them
  • Just assume stress is a condition of work, so why should they try to make it better for others?
  • Their life is essentially just meetings/calls and nothing else

I’m sure there are other reasons, but those were the first ones that jumped out.

Could we make training better and incorporate these elements?

Probably not cookie-cutter HR training, no.

But we could certainly do this at the micro-level: have managers develop a toolkit of effective questions they ask to learn about direct reports. The toolkit is then shared. Pretty easy, right? If you’re stuck as a manager, look at the toolkit — or know who to approach and speak with.

I’d lead with this question above, though. Stress is pervasive and kills teams/productivity. Managers are often horrific at managing stress and constant change. But this one Q seems like it would go a decently long way.

Your take?

Ted Bauer


  1. I was just talking with my fiancee yesterday about the whole “that’s always the way we’ve done it!” canard. Unless that phrase is intended to shut down conversation (which I’d wager a good deal of the time it is), it is an opportunity to show people WHY abiding by a process is effective.

    Like, “this is always the way we’ve done it, because Mr. so-and-so will pee himself it we don’t”. Sure, that invites the possibility that the traditional process might be questioned and possibly improved, but it can ALSO impart the idea that managers care about

    a) passing along the tradition/process to the next generation of workers

    b) the intelligence and dignity of their staff (not rudely shutting down an opportunity for learning)

    c) helping their staff understand WHY something is the way it is and must stay that way (by presenting consequences).

    Failing that, it’s as I suggested—simply a condescending way to shut down a conversation and stunt the collective intelligence of an organization.

    • Canard…what a great word!

      I agree with you and also with Ted’s article. It seems that modern day management follows “the path of least resistance” anymore – every man for himself, which, if that’s the case, why would they (management) want to “rock the boat” and be questioned as to why the traditional process isn’t being followed? Sad, but true. I see it everyday at my place of employment. Has the world always been this way and we’re just now seeing it play out “more often” because we can communicate via the internet with people that we normally wouldn’t connect with?

      • Perhaps that’s so. It’s disconcerting to me as we are so often taught to believe that managers/those who found and run “successful” organizations (I put successful in quotes because I believe it to be far more subjective a position than we make it out to be) are well-educated, thoughtful, visionary leaders; in actuality, they’re often anything but. I’m actually OK with that, as long as it’s honestly presented! Taking the time to be vulnerable in situations like Ted describes can help humanize managers and build empathetic bonds that strengthen an individual’s loyalty to an organization. To me, “going the extra mile” to explain why something wouldn’t work indicates that a manager CARES about the people working for them and doesn’t view direct reports as annoying iPhone notifications come to life that have to be swatted away.

        Anyhow—to your point about people we wouldn’t normally connect with—if you wanna continue the conversation on these and similar topics—plopcornblog@gmail.com 🙂



        (I agree, isn’t “canard” great? I feel real smart when I use it :] )

  2. The most constructive article of yours that I’ve read. I love the recommendation, and I’m going to remember that.

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