my boss’s boss asked me a fantastic question

by Alison Green on November 12, 2020

A reader writes:

I wanted to share this amazing question I got from my boss’ boss not too long ago because it stopped me in my tracks, it was so good and helpful.

Setting the scene: My boss Perfuma was enjoying some much-deserved time off for a few days, and we ran into a tricky situation with a handful of customers in a public setting who were upset about how we were advertising our, let’s say, unicorn grooming. I let Perfuma’s boss Glimmer know, and after a little back and forth with some other teams, Glimmer sent me this message:

“About the messy unicorn responses, I don’t want to be prescriptive toward you and the Unicorn Response Team, because I believe you know best in many instances like this. So before moving forward with a plan, I’d like your perspective on two things:
• What do you think Perfuma would recommend in this situation?
• Do you have a different or additional recommendation?”

I have a really great relationship with Perfuma, but we do have dissimilar communication styles and tend to word things differently, given free rein. This is well-known and something of a running joke on the team. So I had to consider how Perfuma would soften the language and touch on broader ideas, as well as how I would focus on facts and transparency.

Anyhow, maybe this isn’t rocket science, but it really impressed me in the moment and helped me organize my thinking a lot. (I think it would have worked if Perfuma and I were peers and Glimmer was our supervisor as well.) I know you get a lot of letters about awful management, I just wanted to share this example where someone really nailed it. Maybe it’ll be helpful to someone in a similar spot!

Yes, this is excellent! In addition to what you noted, it also does all of the following:

* expresses confidence in your and your team’s expertise, rather than being heavy-handed

* bakes in respect for Perfuma’s role as the team’s leader

* makes it clear that she knows your perspective may be different than your management’s and she wants to hear that if so (which is not always clear to people several layers down, and is a signal that can meaningfully affect things beyond this one interaction)

* is perfectly calibrated to make you feel respected and valued

It’s a great approach.

You may also like:
{ 68 comments }

{ 68 comments… read them below }

  2. Emeemay*

    1) this is neat, and nice that it continued to give your boss some time off, especially in a case where it sounds like you + boss’s boss had things well in hand

    2) 100% here for the She-Ra references :’D

    3. Three Flowers*

      Yeah, I really just skimmed the question to get the She-Ra references. I vote She-Ra replaces GoT as the default source of names around here. :)

        1. The Beignet Incident*

          I love Shadow Weaver too much to see her in that role!
          IMO, the toxic bosses should henceforth be Hordak. :)

          1. Brisvegan*

            Nah, Horde Prime!

            I liked the resolution of Hordak’s story, but Horde Prime was just an arsehole.

    4. fluffy*

      I enjoy the She-Ra references but they had the unfortunate effect that I was just imagining this as a weird episode of She-Ra and completely could not comprehend what the actual workplace/management aspect was about. I’m going to have to do a search-and-replace on the text to something way more mundane so that I can actually understand it, I think.

    5. Txag18*

      Also +1 for the She-Ra references!

      I love when letter writers use clever or unique names for the characters in their stories. I think it’s easier to follow than when there’s generic names.

    6. Elizabeth West*

      It’s a great question indeed. Heh, I didn’t get that they were references from She-Ra, but I loved the unicorn theme.

      1. AnotherAlison*

        I’m a child of the 80s and didn’t know they were She-Ra references. : (
        The child me preferred crap like the Care Bears.

        1. Brisvegan*

          I was a 70’s baby and barely remember original She-Ra. My daughter persuaded me to watch the new one. It’s amazing! It has some of the best queer representation in media that I have ever seen. It also has a wonderful non-neurotypical main character. Plus it’s a lot of fun.

  3. Jellyfish*

    The question also respects Perfuma’s time off by not pushing for a response from her while she’s on PTO.

  5. 867-5309*

    I am frequently butting heads with my CEO and how we approach different things and I love this to be able to communicate more effectively with him. If I can start my thinking with “here’s what he would do” and then think about what I would do, it will help me to approach my recommendations to him in a more productive way. Thanks!

  6. Sola Lingua Bona Lingua Mortua Est*

    I’m glad it worked out, but if Grandboss doesn’t really have a good grip on the situation and know all the parties well, I feel like this strategery is ripe for abuse.

    I would, however, be infinitely amused to hear what others think I would say.

      1. Sola Lingua Bona Lingua Mortua Est*

        In short, conveniently forgetting or failing to predict something the boss might insist on or prioritize that the employee doesn’t value.

        E.g. (& vice versa)
        Boss has a table/database fetish and a non-database alternative is live before boss returns.
        Agile employee skips planning when traditional boss is on vacation.

        If I were in a supervisory role and my supervisor pulled a stunt like that instead of touching base with me while on vacation, I’d be job-hunting the moment I return.

        1. Keener*

          @sola true time off with no work thought is so important to our mental health and our well-being. If you feel that you can’t trust your boss and subordinate to collectively resolve a situation in your absence it is speaking to much greater issues in your workplace. I’d be getting out of there ASAP and not waiting for the situation of a problem while your on vacation to arise and then quit.

        2. Square Root of Minus One*

          I’m not sure. It doesn’t seem to me that the timeline here would allow for the implementation of new systems. It’s more crisis immediate management, which may or may not be cast in stone later.
          If the employee accurately represents Perfuma’s view on the matter, great. If not, it can be corrected reasonably early and probably with limited damage, and Perfuma and Glimmer get useful info on the LW.

          If you can’t trust your team to navigate a crisis to a point you can’t even take a week off… it’s… not good?

          One could compare this letter to the one where the LW, as a new employee, used her boss’s absence to implement new systems with her n+2 and was blindsided to get fired. I bet this LW would probably have eluded question 1 and droned on question 2, which would show that LW didn’t know/understand/care for her supervisor’s opinion.

          1. Ask a Manager* Post author

            Yep — honestly, one mark of a good manager is that you can leave for a week and trust that things will be fine because you’ve built a team with good judgment and good training.

          2. Sola Lingua Bona Lingua Mortua Est*

            It doesn’t seem to me that the timeline here would allow for the implementation of new systems.

            There are projects and stages of projects that can be completed inside a week. In a lot of places, once something working has been wrought, it’s doubly hard to replace it.

            If you can’t trust your team to navigate a crisis to a point you can’t even take a week off… it’s… not good?

            I’m more disturbed that grandboss can’t make and own a decision and is resorting to imagining what boss would say instead. Come to think of it, why does grandboss even need boss if grandboss and OP’s team can just imagine what boss might have thought?

            1. Ask a Manager* Post author

              What on earth?! It’s very normal and not problematic for a manager two levels up to not be as familiar with the work as the people doing it one and two levels below her. That’s not a sign of a problem. A good manager *would* ask for their input in this situation; that’s how you empower and respect people.

            2. Eleanor Shellstrop*

              Surely though ”So before moving forward with a plan” indicates that grandboss will be confirming and agreeing the final plan – and therefore will own accountability (and that is the point of grandboss).
              I think this shows a far more supportive management style on grandboss’ part, and indicates that grandboss is aware that OP is more than competant to bring Grandboss all the best information to make that final decision. It’s more than likely that OP and boss are closer to the detail, which you see in this quote ”because I believe you know best in many instances like this”, so grandboss just making a complete decision first hand may not make sense.

            3. Jane*

              As someone who is frequently the “grandboss” in scenarios like this, I wouldn’t be avoiding the ownership of the decision when asking these questions. Rather, I would be coaching my team through considering multiple perspectives and raising their thinking up to a higher level, while subtly reminding them to keep the priorities their manager has set in mind. And if after that, I want to go in a different direction, at least the team will know their opinions were respectfully considered. Plus, a benefit of having a team is getting more brains and broader experiences working on problems. They might have a better idea than mine, and I don’t want to ruin it by throwing my thoughts out first.

              1. Sola Lingua Bona Lingua Mortua Est*

                As you’re normally grandboss, are you normally asking your employees for their absent boss’ opinion because you do not know it, because you want to hear how their representation of it differs with yours, or to test their adherence to the opinion that you already know?

                1. JSPA*

                  Uh, sure, when it’s about a sub-detail or quirky facet of a project that they’ve likely given thought to.

                  Or perhaps nobody’s considered that particular wrinkle so far as the lower level employee knows, and…that’s fine. They can say so. You can then decide to cross check with the person who’s on leave, or make the call yourself.

                  But before you run roughshod over someone’s partially-charted plan or considered opinion when you know you’re just shooting from the hip, you (obviously!) ask if a partially-charted plan or considered opinion exists, and what the other alternatives might be.

                  Otherwise, in some essential functional sense, you don’t really have employees (good or otherwise). You have robotic extensions of your will, who merely happen to be human beings.

                2. Sola Lingua Bona Lingua Mortua Est*

                  But before you run roughshod over someone’s partially-charted plan or considered opinion when you know you’re just shooting from the hip, you (obviously!) ask if a partially-charted plan or considered opinion exists, and what the other alternatives might be.

                  I’ve never been in a situation where that information has been more readily accessible from below than from above. It certainly sounds novel.

                  The only part of what the grandboss did above that I object to is trusting the team to speak for boss. Getting information from the team is logical.

                3. fhqwhgads*

                  You’re sort of making it sound this type of scenario is automatically some sort of “gotcha”. Believe it or not, there are some very functional, considerate workplaces where that is not going to be a thing 99.5% of the time.

                5. Jane*

                  Sola Lingua Bona Lingua Mortua Est – I haven’t asked in this exact way before, but I do like it. I say something like, “If you were [their boss’s *level,* not name], how would you want the team to handle this?” If I used the wording from the letter, I would be asking the question for the same reason, and it’s not any of your 3 choices (especially the last one). People have specific, detailed knowledge about their work/situations/customers that I do not and should not have. I want them to use that expertise to solve the problem while considering the problem from a bigger-picture perspective – how might the implications of your decision affect the rest of the team or department or organization? If they say something that surprises or concerns me, we explore that. If I feel that their approach is different from maybe the way I (or their boss) would handle it, but not for any red-flag reasons, I typically tell them, “okay, thanks for looping me in. Sounds like you have a plan.” Not every thing has to be done my way. If there are red-flags (violates policy, doesn’t align with our values or strategy), I would make a different decision and then deal with the red flag as appropriate.
                  (Note: I would ask these questions with someone inexperienced/new. That would shift my approach.)

                  Also, to your later comment about not being in a situation where information is more readily available below, I must say that I’m a little stumped by that! There are times where I might know something relevant, and I’ll lead with that. But otherwise, in situations like letter writer’s, I, as grandboss, would likely have more questions than answers.

                6. Jane*

                  would *NOT ask these questions with someone inexperienced/new

                  (can’t figure out how to edit. apologies)

                7. Sola Lingua Bona Lingua Mortua Est*

                  @Jane

                  above & below

                  My boss reports to you; my boss doesn’t report to me. I’m on a need-to-know basis; you’re not. Just as I explain myself to my boss, I would expect my boss to have explained him or herself to you.

            4. Square Root of Minus One*

              Grandboss isn’t imagining. That’s pretty much the point. She’s asking the people she has on hand for data about a most likely scenario. She’s gathering data to avoid “might have thought” and steer toward “is most likely to have thought” or even “would have thought”.
              What would be “taking ownership”? Interrupting Boss’s vacation? Sounds like the opposite of decisive. Wait for Boss’s return? Worse. Not ask anyone? That increases the risk for a bad decision. What’s left?
              As I see it, taking ownership isn’t about not consulting anyone. It’s accepting the consequences, good or bad, of the decision you made.
              For your question… I suppose Grandboss needs boss because she can’t handle managing LW’s whole team day after day on top of her own work.

            5. Reed*

              I’m very proud of the fact my GrandBoss trusts me to get on with my job. On several occasions she has cheerfully said she defers to my judgement as I know the system I manage inside out and backwards and she does not, specifically because she is GrandBoss and needs to be concentrating on the bigger picture and not on every detail of procedure and protocol. When Boss is on leave I do sometimes run queries past GrandBoss and she usually says ‘you know what Boss would do, you know how the system works, I trust you to manage this.’

        3. MCMonkeyBean*

          See for me if my supervisor bothered me with these questions while I was on vacation instead of relying on the perfectly capable people who were there and available, then I’d be job-hunting…

    2. JSPA*

      That’s mitigated because, given the format, it’s all on record. And, secondarily, because boss is only out for a brief while, so this is a question of “which route do we start working on,” not “this’ll be done before they’re back in the office.”

      If employee dramatically misrepresents boss’s default preferences or stances on something major, employee gets fired, either for machinations or for over-reaching or for simple incompetence.

      1. Sola Lingua Bona Lingua Mortua Est*

        If employee dramatically misrepresents boss’s default preferences or stances on something major, employee gets fired, either for machinations or for over-reaching or for simple incompetence.

        But, unfortunately, I’ve never witnessed redoing the work right be part of that plan.

        1. Empress Matilda*

          But how often have you seen this situation actually happen? The first part, I mean, where Middle Manager goes away for a period of time and Worker Bee colludes with Big Manager to deliberately sabotage them? I’m not saying it never happens, just that I can’t imagine it being so common that it becomes a default assumption. For the most part, I would hope we could assume that we’re working with competent professionals who we trust.

          If I’m away and somebody has to handle an issue on my behalf, I would expect the following:
          *They’re acting in the best interests of the organization
          *They’re acting to the best of their abilities
          *They know when something is truly outside their range of expertise or skill, and they know what to do if this happens (including calling me on vacation if necessary, but also asking someone else for help, or just doing nothing until I come back)

          I’m not clear on the scale of the situation the OP is describing. But it sounds to me like Grandboss is going about it the right way, by asking questions and finding out more information. Sure, OP could lie about her boss’ intentions, but presumably she could do that at any time. At some point, you have to trust people, you know?

          1. Ask a Manager* Post author

            Yep — and frankly if that happens, you have a major problem on your staff, which is good to know, and you deal with that accordingly when you return.

            If you’re a manager whose first reaction to this is that you don’t trust your people, that’s a flag that there’s a big piece of your job you’ve been neglecting.

          2. Sola Lingua Bona Lingua Mortua Est*

            The first part, I mean, where Middle Manager goes away for a period of time and Worker Bee colludes with Big Manager to deliberately sabotage them?

            I haven’t seen the collusion scenario, but I have seen Worker Bee use strategic omissions and vagueness and Big Manager’s lack of detail to circumvent Middle Manager, and the team be saddled long-term with a bizarre enclave. Worker Bee isn’t responsible for it because Big Manager signed off on it, Big Manager isn’t responsible for it because Worker Bee’s advice was substituted for context, and Middle Manager is liable for it because it’s a mine in Middle Manager’s field.

            1. Nassan*

              That’s just bad management (shifting blame to others, not taking responsibility, not fixing stuff, not managing a lying employee). Of course good questions can be manipulated to bad results in a bad culture. LW didn’t suggest how to fix bad culture but a good approach that works in a reasonable workplace.

  8. Aepyornis*

    It’s perfect indeed, and I am definitely filing it for later :).

    On thing my fabulous dad taught me (an unapologetically feminist nurse who tirelessly promoted women for 40 years and starting giving me professional advice when I was 8) was to ask his reports to add their own opinion/reserves/recommendations on topics they are experienced in rather than just passing documents/reports along. For instance: Report: “Here are the latest recommendations from the Infectious Diseases Board for Lama Feet Infections” > Nurse Father “Are they overlooking something and do you feel they would be implementable as such?”. It was crucial to make people feel validated and confident to express themselves in a field that tends to be highly hierarchised and to overlook the experience and expertise of people lower in the ladder (not to mention the gender aspect).

  9. Peter Piper Picked a Peck of Pickled Peppers*

    This really is amazing. So many managers / companies have the mindset that There Is Only One Way To Do This (And The Senior Person Is Always Right). Your boss’s boss obviously thinks way less prescriptively and the communication style is also fantastic – clear and respectful of both you and Perfuma.

    “maybe this isn’t rocket science” – it kinda is, based on how many people get it wrong.

    ‘helped me organize my thinking a lot” – this is another rarity – so often these requests for information are ambiguous and confusing, and we end up being wishy-washy in our responses because we just aren’t clear on what is needed.

  10. I'm just here for the cats*

    This is great and I’m glad you have such a great boss.

    It makes me think of a time at a previous call center job. the place was so toxic but there was great things. I had a Kudos call (when a customer wants to talk to a supervisor because you did a great job). My direct supervisor was gone at the time and I was having problems finding someone. So the director of the entire center comes over and takes the call. The customer remembers something that they want to ask about product. He says something about how I’m he expert, and know more information than he does as the director (which was TOTALLY true). Hands the customer back to me and I finish up. It was the one time i felt truly appreciated in that job.

  11. I'm just here for the cats*

    This is great and I’m glad you have such a great boss.
    It makes me think of a time at a previous call center job. the place was so toxic but there was great things. I had a Kudos call (when a customer wants to talk to a supervisor because you did a great job). My direct supervisor was gone at the time and I was having problems finding someone. So the director of the entire center comes over and takes the call. The customer remembers something that they want to ask about product. He says something about how I’m he expert, and know more information than he does as the director (which was TOTALLY true). Hands the customer back to me and I finish up. It was the one time i felt truly appreciated in that job.

  12. TimeTravlR*

    Being in a support role of some type or another most of my career, I have always thought this way. How does my boss talk? think? write?
    I had a newish but much more senior person express amazement to me that his work was always pencil-whipped by the boss while mine came back with minor edits if any. I told him, learn the boss’s style and then communicate like that.
    Works every time!

    1. rita*

      I had a boss that I *knew* needed to correct something on every. single. thing. we gave her (she was not great), so I knew if I left one or two obvious things to correct, she could do that and feel useful. But if I didn’t leave something obvious for her to correct, she’d start dismantling things just for the sake of feeling like she was needed.

      School can operate in a similar way, particularly college—if you can figure out what is important to the teacher and serve that, it can go a long way toward helping your grade.

      1. Penny Hartz*

        I had an internal communications job where I did a lot of “ghostwriting” for senior executives. The CEO of the company and I got along really well, and we had a similar style of writing and speaking, so whenever I wrote something for him, he’d have one or two changes or corrections and that would be it (except for a “Looks great! Thanks Penny!”). Most of the other C-suite execs were the same. But if I had to write something for a VP–oy. Changes for the sake of changes, questioning insignificant details without offering suggestions (“Should we say ‘really’ here? Different word choice?”), changes to the font and type size (!). And heaven forbid they actually track the changes in Word, so I’d have to visually compare docs.

        My boss–who was terrible in pretty much every other way–said, “They think they have to prove their paycheck. Just make the changes you think are reasonable. They won’t even notice.” And they never did.

    2. Miss Muffet*

      pencil-whipped…what a great term! I have been on the flip side of reviewing things that are written and have to catch myself from over-editing sometimes. I try to remember that this person has their own voice and unless the stuff is really factually wrong or unclear, I need to leave it in their voice. It also super helps people want to learn how to get better when their stuff doesn’t come back bleeding from red pen (at which point they’ll just throw in the towel and say why bother).

  14. TootsNYC*

    It also kind of forces you to train yourself in “understanding your boss’s standards and preferred approaches.”

    I typically spend a lot of mental energy on trying to calibrate myself to my boss. I think through solutions before I bring problems, and sometimes I try to predict what my boss will choose. I think of the pros and cons and ramifications of the possible decisions, and I sometimes ask for explanations of why they chose one over the other.
    I test to see if my basic assumptions are like theirs, and to see if I can identify what their core approach is like.

    I like to be able to say, “I think our boss is going to want X; let’s get her ruling,” and then have the ruling be, “X, please.”

    I don’t ever completely discount my own approach, but I do find that I adjust it if I have a lot of respect for the boss, and if I see the wisdom of their approach.
    It’s been a very powerful self-training exercise.

    1. Lord Peter Wimsey*

      Yes to all of this! I had a grandboss who was like one of those demanding teachers in school — her expectations were quite high, but (mostly) needfully and fairly so. We learned to think through what we brought to her and anticipate her response — for example, what additional questions was she likely to ask, so we could have the answers for her ahead of time.

  15. Banana Naan*

    Can there be an article about great questions to ask? I keep a list of questions to ask myself when I write, but I would like to start one for work too!

  16. Captain dddd-cccc-ddWdd (ENTP)*

    Wow! I had an instantly different response to this, based on my experience in a similar situation where my manager (between me and the actual decision maker) was unexpectedly out. [“Yet again” in my case.]

    “What do you think Perfuma’s response would be?” … Oh I think they’d deliberate a little bit and then throw the decision on to me to make. And then I’d say “do X” and if it turned out to be right they’d claim it but if it turned out to be wrong they’d throw me under the bus!

    “Do you have different or additional recommendations?” … Yeah, I’d do/suggest X and/or Y as I’ve been advocating for since last Easter anniversary.

  19. My Name's Not Amy*

    My last boss, who was an absolute terror to work for, insisted that we be in lockstep, with me parroting her communication style and opinions at all times. She considered it disrespectful to her if I didn’t (it wasn’t) and claimed we were ruining our credibility with the executive team if we had different views (it didn’t). I am so happy to be out of that environment and working for a leader who appreciates different points of view now. OP’s grandboss gets it. I wish every manager could read this!

Comments are closed.