How To Ask for the Truth

“I’m really sorry to hear you are leaving. I wish I would have known you were unhappy.”

Every leader who has been around long enough has probably had a conversation like this after one of their team members resigns.

In an ideal world, people are open about every problem they face in the workplace, but great leaders know that we don’t live in an ideal world. There are a lot of reasons you won’t always know what might be brewing inside your team. People can be shy. People can be afraid of confrontation or retribution. People can blindly obey power structures because that’s how they’ve been taught. People can feel like “telling on someone” is disloyal.

A trip to the dentist’s office (!) yesterday reminded me how important the concept of proactively asking for the truth is.

When I left Twitter and moved back up to Seattle last year, I had to find a new dentist because the one I’d gone to since I was 15 had retired. I chose my neighborhood dentist, mainly out of convenience. Yesterday was my second visit, and let’s just say that for the second (and final) time the hygienist carved up my gums like she was auditioning for a Tarantino movie. I have pretty good dental habits with the possible exception of being on #TeamNoFloss, so there was no reason my gums should have gotten destroyed in the dental chair like they did yesterday. Halfway through the bloodbath, I asked her to ease up, and she did, somewhat, and then proceeded to tell me my gums were really bleeding a lot.

Thanks. I know. You did that.

Anyway, the moment I left the dentist’s office, I realized I had three choices:

  1. Continue on like nothing happened.
  2. Tell the dentist that her hygienist was a monster.
  3. Say nothing and find a new dentist.

Those who know me well should have no trouble figuring out which option I chose.

I chose #3 for a few reasons. Firstly, I wasn’t about to get torn up again. Secondly, there are plenty of other dentists out there for me. And finally, I didn’t feel good about getting the hygienist in trouble.

But here’s the really important part that applies to management: if the dentist came up to me and actually asked me how the hygienist had done, I would have sang like a canary. Because she did not, I walked away non-confrontationally and this hygienist will now continue to drive people away from her clinic.

If you are managing people, chances are there are similarly troublesome things you should know that your team members will not feel comfortable volunteering without you specifically asking. I know this because I’ve experienced it simultaneously as a manager and an employee.

If my CEO sits me down for a 1:1 and says “how’s everything going?”, I am likely to rattle off a long line of accomplishments and things I think he or she would be excited about.

If instead he says “I’ve heard from others there are some challenges working with Jim Bob. Tell me what’s been difficult for you.” then that unlocks a level of candor that I may not have been comfortable volunteering on my own. In other words, I don’t think it’s my responsibility to proactively tell you every little negative thing across the entire organization, but if it’s important enough for you to ask me about it, I’m going to answer every question you have and give you as clear of a picture of the overall situation as I can.

There are three types of employees in the world when it comes to disclosing issues:

  1. Those who will always tell you about problems.
  2. Those who will never tell you about problems.
  3. Those who will tell you about problems when asked in the right way.

I love my ones and am frustrated by my twos, but I feel like at least 9 out of 10 people are actually threes. One of the most important things you can do as a manager is assume everyone is a three and act accordingly. Here are some examples and how to get to the truth with each.


You notice a team member withdrawing from discussions in meetings.

Wrong: In your next 1:1, ask them “how things are going”.

Right: In your next 1:1, tell them that you’ve noticed they’ve been especially quiet in meetings lately, and ask them why. If they don’t volunteer anything, suggest your own causes like “is it because no one lets each other finish sentences in there?” and let them correct you with real reasons.


You hear about a situation in another department across the company where a woman was sexually harassed.

Wrong: Stay as far away from it as possible and assume if it was happening in your department, your employees would tell you.

Right: Pull some women (and men) on your team aside individually and ask them if this sort of thing is common inside the company and if they have ever experienced it. Ask them if it did happen to them, would they feel comfortable telling you about it? Assure them you want to know and that it’s everyone’s job to protect against abusive behavior, inside and outside the department.


A new team member joins the company and you’ve heard nothing but positive about her during her first month.

Wrong: Assume everything is positive and stay out of the way.

Right: Have a 1:1 with her a month in and ask her “what are some of the things about this place that you find weird? What makes your job harder here than at the last place you worked at? What can I do to help you?”


A team presents their project to you and wants your approval for launch.

Wrong: Assume everything went swimmingly and ask them if they need anything.

Right: Ask “of all the things you thought would go smoothly in this project, what thing went the least smoothly?” I love that question because it gets to so many different potential things to fix, from team communication, to dev tools, to security procedures, to legal requirements. (I stole this one from Dick Costolo, as it’s one of my favorite questions he likes to ask.)

When things go wrong on a team I manage, one of the first things I always ask myself is “what questions could I have asked to find this out earlier?” and then I start asking those questions more regularly. You will never get to a point where you are always asking the right questions at the right time, but half the battle is simply knowing that that is perhaps the most important part of your job.

There are many reasons why problems simmer below the surface for so long inside of workplaces, but as case after case has shown us, it’s only a matter of time before the ground truth catches up to you.

Luckily, the only tool you need to know what’s really going on at your company is your own inquisitiveness.

Ask and ye shall receive.

(This post also available on Medium.)

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