Dealing With Critical Persuaders
June 2, 2016 11:16 AM   Subscribe

At work I regularly work under someone who is, I am sure, a decent, friendly person. But we often end up at loggerheads because I find him critical and aggressive. I'm looking for new ideas on how to deal with this.

Here's a recent example. My employers in the USA are organising a meeting for contractors and employees to get to know each other. Not my cup of tea, but I can see the good side, so OK, I am proactive and make travel plans (which involved asking if anyone wanted to share a car - noone answered, so I made plans including trains etc).

Now, weeks later, the boss in question calls me and says I should travel with employee X. What are my plans? Can I change them? Why did I book that hotel - was there nothing cheaper?

I start answering these things and am on the defensive. Truth is, there are some valid points, but I did the best I could at the time and am now happy and settled with my plans. And I don't really understand why I am being bossed around so much and so late in the day. So I explain as best I can and agree to look at how we can merge travel plans.

When the call ends I am frustrated and annoyed. What was so wrong with what I had? I collect my thoughts and write a friendly but assertive email saying that on reflection I'd rather just do things as I had planned, and hope that is OK. It's a good email and I get the result I want. Great.

But a reply from the boss is somewhat offended, saying that he was contacting me because I had asked to share cars. And really, if he'd said that at the start, and asked for my input, rather than being questioning and demanding, we could probably have worked something out.

So how do I get better at this? How do I take what seems to me to be an aggressive opening and, instead of defending and then counter-attacking (which worked), look for a more positive outcome? There are definite cultural factors here - we are different nationalities, and my boss's first language isn't even english (not a criticism - his english is way better than my spanish - just context).

Really, I like the guy. I just wish I could handle him better. For various reasons I think it's me that has to change. So how do I do this? I don't seem to have the time to think while on the phone. Afterwards I struggle to do better than a textbookish "friendly but assertive" (years ago I wouldn't even have managed that). Is there an assertiveness 102 that goes more into negotiating, or something? How do I welcome change rather than defending what I have already done?
posted by andrewcooke to Human Relations (13 answers total) 5 users marked this as a favorite
Remind yourself before going in - this guy is direct and detail oriented and maybe a little bit controlling and it kind of pushes my buttons. Sometimes just doing this in advance prevents feeling bowled over.

Own your in the moment reaction - wow boss, way to put me on the defensive! Let's see [stalling phrases while you recollect yourself] I did it this way because Reasons. I was trying to optimize for Constraints, given my Goals. But do you not agree with my Reasons and Constraints and Goals? Now you can start the real dialogue. Because if you don't agree on those three things, you will argue endlessly.

I think your feelings are totally normal - being micro-scrutinized can make anyone feel put on the spot. Just say to yourself over and over: although he outranks me in the office, humanly we are equals. Repeat it till you believe it.
posted by St. Peepsburg at 11:33 AM on June 2, 2016 [3 favorites]

I always found it helpful (to me) to look at these sort of situations as simply a boss/employee issue. When my boss was being seemingly random, I just said to myself, "Self, he is the boss. If he wants to do it this way, then we do it this way."

I also, based on your post, would have sent an email that went on record as no one replied so you were making your own plans. "Two days ago I sent an email asking if anyone wanted to make travel plans with me to x conference. No one responded. At the end of the day today, I am going to make my own plans." Then if the boss comes to you with suggestions, you can say you tried, you gave a deadline and the rest of the team did not respond."
posted by AugustWest at 11:35 AM on June 2, 2016 [13 favorites]

One strategy for this to to ask why they're asking.

"Gosh, you seem really concerned about my arrangements, why is that?"

Then the other person can explain what the issue is. "Oh, Larry was just getting his stuff sorted out and since you're close..."

Then you can say, "Oh! That would have been good. In fairness I did offer and got no response, so I went ahead and made my own arrangements."

Now you've let the boss know what he wants to know.

As for why I chose a particular thing for travel , "it was the best option at the time," covers things.

Don't get defensive. It ratchets up tension. Get inquisitive. "Boss, why is it that no information was provided regarding arrangements? I was surprised that we weren't given a specific hotel or ground transport options."

Because that's lunacy!
posted by Ruthless Bunny at 11:55 AM on June 2, 2016 [13 favorites]

Yeah I have this problem where some people's problem solving strategies just seem abrasive. But I know they are well meaning and certainly not personally attacking me (although in the moment it may feel that way).

Mindfulness helps me deal with this. I feel attacked! I notice the feeling, and try to set it aside.

Why did you book expensive room? (I hear what were you thinking?). But take a deep breath and try to answer the best interpretation of the question I can paint (Do you think this booking is cost effective?).

Trying to answer my interpretation of a supportive question gets me better results. So I'd answer, It's three blocks from the conference location and has breakfast so we're saving money (or whatever the answer may be....). Plus it helps me reduce the anger and frustration response from carrying over from minute to minute.
posted by Kalmya at 11:58 AM on June 2, 2016 [2 favorites]

This situation doesn't seem to me like a personality conflict, it seems like he's unhappy about your actions. It sounds like your proactiveness about booking rooms and travel arrangements may not have been appreciated as much as you thought. If the rooms and travel are being covered by your company, your boss is probably under pressure to keep costs as low as possible. If so, it's unclear whether you ever confirmed with your boss that you had permission to book any travel arrangements you want. Based on his reaction I suspect you didn't really discuss it beforehand, and he's a little unhappy that you didn't confirm things with him first and/or may not have chosen the most cost-effective arrangements. Asking whether anyone wants to ride-share (especially weeks in advance of the event) is different from going ahead and booking stuff. Next time I would definitely discuss travel arrangements with him beforehand, and make sure he's on board before you book anything (ideally in writing, like send him an email with your proposed hotel/travel arrangements).

This is all assuming the company is covering your expenses, though. If you're paying for it, it's none of his business how much you spent.
posted by randomnity at 12:09 PM on June 2, 2016 [8 favorites]

yes, i could have done a better job at communicating the discussion there was about pricing (the company is disorganised about who decides what, and this particular boss was not copied on everything). however, this is a consistent problem across many conversations on very different topics.
posted by andrewcooke at 12:47 PM on June 2, 2016

How about, "It will help me know how to answer if you'll explain why you're asking & what you want to do with the information.". Just add that extra step to the whole transaction, and you might find that you eventually get really good, complete understanding (maybe) -- there might be fewer missteps than with less inquisitive people.
posted by amtho at 1:11 PM on June 2, 2016 [2 favorites]

It will help me know how to answer if you'll explain why you're asking & what you want to do with the information

Hi, I'm a boss, but not your boss. If one of my subordinates asked this, it would be difficult for it not to come across as defensive and obstructive. I would likely become much more interested in your travel and be curious to find out what else was going on.

the company is disorganised about who decides what, and this particular boss was not copied on everything

That's incredibly annoying. But pick your battles: is travel arrangements the hill you want to make your stand on? Assuming it isn't, enlist him/her as an ally on this. How about a short email that says,

Hey BOSSNAME, Sorry for the confusion regarding my travel arrangements for TRIP. As we've discussed, I've already made all my arrangements for the upcoming travel. I could cancel or change some of these reservations, but it would take me approximately X hours that I would otherwise be working on PRIORITY PROJECT, and could cost COMPANY $Y in cancellation fees. Please let me know how you'd like me to proceed.

To avoid future confusion, how would you like me to plan future travel? If you identify a specific budget or expectations, I'll be happy to work within them. If you'd like, I could send you a draft itinerary prior to booking for your review. Alternately, if you'd prefer for the travel to be arranged directly by you, just let me know.


I guarantee you your boss doesn't want to review your travel details in advance (as long as this isn't an issue like you're making reservations at the St. Regis and the rest of the company typically stays at Holiday Inn Express for 1/3 of the cost), and I definitely guarantee your boss doesn't want to make your reservations for you - but by offering you're getting out of the way of this issue and giving yourself space to focus on more important issues.

Also, it sounds like you have two issues that are troublesome to both you and your boss- company policy is vague, and s/he's not always operating as your supervisor. To the degree possible, enlist your bossperson as an ally in trying to get these issues clarified, this also offers the two of you a chance to work collectively on a shared issue and build a better rapport for future projects.
posted by arnicae at 1:49 PM on June 2, 2016 [14 favorites]

To avoid future confusion, how would you like me to plan future travel? If you identify a specific budget or expectations, I'll be happy to work within them. If you'd like, I could send you a draft itinerary prior to booking for your review.

Yeah, this is perfect. The more clear you can make the protocol beforehand (especially if it's in writing), the less hassle you'll have later.
posted by randomnity at 1:56 PM on June 2, 2016 [1 favorite]

It can help to wonder why they are asking, stick to the facts, and avoid sounding blamey yourself.

Some people come from a deeply rooted mindset that if something went wrong, someone must be to blame. If you have reason to believe that, say, gravity or happenstance is at least partially responsible, it can help to try to ascertain the facts as neutrally as possible. Try really hard to not blame them, even for being unpleasant in their presentation. It only reinforces the problem because these folks are typically motivated by a desire to not get blamed themselves due to baggage. So, if you can model the idea that sometimes things are not how we would like them to be even without anyone being to blame, they may get easier to deal with.
posted by Michele in California at 2:16 PM on June 2, 2016 [2 favorites]

thanks, i can probably make "ok, whoa, slow down, what's this all about?" work (avoiding "you seem really concerned..." which sounds odd to me). and there's a bunch more things here to think about.

(some answers make sense in other contexts / companies. i have tried to change the culture and this meeting is, in fact, related to such changes. but at heart it remains a collaboration of academics who dislike hierarchy and i have to live with that. and they've been good to me.)
posted by andrewcooke at 3:58 PM on June 2, 2016

oh it's academics

ohhhhhh ha ha ha

ok well they are asking questions because they want to find the flaws in your plan and fix them. which is actually critical of them. but it's like a kneejerk response that some academic-types have to people asking for help. they can't just help. they have to figure out WHY you need help and OVERTHINK your situation and find the BEST POSSIBLE SOLUTION and they take every question or request for assistance as an invitation to do just that.

I mean it's a curiosity thing as much as it is a criticism thing. You could maybe think of it that way.

since he probably likes doing this it's going to be hard to slough him off. this is fun and satisfying for him and he thinks it's "helpful." so you have to just avoid each individual instance. maybe you can say something like:

"oh I don't want to change my plans, but if you're curious let me send all my plans to you via email."

you know he wants to change/fix/optimize so right out of the gate just say whether you are or are interested in changing/fixing/optimizing.

and if you are, then don't make him ask a bunch of questions b/c you'll both get annoyed by that. tell him what the problems are.

good luck
posted by internet fraud detective squad, station number 9 at 4:15 PM on June 2, 2016 [4 favorites]

I've worked with people like this. It was really frustrating until I took my skin out of the game; I managed to remove whatever personal stake I had. I got my own sense of purpose that wasn't impacted by the personal side of things. Each of us has to decide how much we're willing to flex here; I've found a lot to be gained by flexing. I gain cooperation and more pleasant interactions, and I haven't lost my autonomy.

More recently, I think I can sometimes be perceived the way you perceive your boss (especially if I forget that being nice is important and not just an add-on to a conversation). So I'll try to speak from both sides.

You said:
Truth is, there are some valid points, but I did the best I could at the time and am now happy and settled with my plans. And I don't really understand why I am being bossed around so much and so late in the day.

This sounds so personal to me. You are processing it not as a worker but as a person. It sounds like you would have liked some appreciation for your process and efforts, which is fine, but in this imperfect world, it might be something to bring up with your boss, get from somewhere else, or stop expecting. From a professional standpoint, it doesn't matter whether you did your best; there might be room for improvement in the process. It doesn't matter if you're happy or settled; that's not really relevant to the nuts and bolts of how things go down. And I don't read your boss' interactions as "bossing." He is just bringing up other options. It's up to you to say if they are not actually options. It's up to you to respect yourself enough to be able to affirm yourself and your process, and then possibly flex (or defend your points) as the situation calls for it.

And really, if he'd said that at the start, and asked for my input, rather than being questioning and demanding, we could probably have worked something out.

If the only reason things can't be worked out is the way he approached you, then (recognizing it sucks and doesn't feel good) you are the barrier.

I just, from my experience, would say that as much as you can get your personal attachments out of it, the better you will be feeling.

Here are some techniques:

- Think of the interaction not as something personal between you and the boss, but just a process you're going through to solve a problem together. "It's not personal -- it's just business." In this framework, you both help move forward by asking questions, providing the right information, and focusing on reaching the goal. Taking things personally is a distraction from solving the problem.

- Find a visualization to help separate the personal from the practical. Perhaps imagine that his words are coming toward you; the ones that help address this interesting work question/problem/puzzle travel straight to you and you take them in. Anything personal is really peripheral--you can let that take a route above your head or to the side; watch those words or ideas fly past you and disappear. Or, imagine that you are a smooth stone and water is pouring over you; his words are not soaking in, but simply washing over you and then going away.

- Frame personal jabs as weakness on his part. Only a weak person takes things to a personal level when there are other things to work on.

- Think appreciatively about his ability to communicate directly and get things done. Monitor your thoughts and welcome more positive thoughts. "He is asking this so he can save the company money." "He strives to do well in his job." "He is organized." I've found my thoughts influence my behavior in subtle ways. I try to build up patterns of appreciation to cover over the hard stuff.

- Assume he has good intent in what he does. If you feel confused, or think he did something wrong, assume he would have done differently had he known better; or assume he has a good reason for what he's saying or doing, whether that's a business reason or just because he learned that approach earlier in his career.

- Think of your role as helping, in a friendly way, to parse through your boss' wishes and thoughts, (again) in pursuit of this goal you have together.

- Release your sense of responsibility to make the "best" decisions, and accept that your boss' word carries the day. You are not paid to do just what you want to, but rather whatever the people in authority decide is best (in situations where they have oversight).

Some things you could say:

"Sorry about that. I can see how my decision to ____ could lead to ____. Next time I will ____."
"I'd like to be sure I'm getting this right. Just to confirm, what you're asking for is..."
"Oh, man, I tried to ____, but just couldn't because of ____ constraints. Hope it can work out better next time."

Consider something like, (regretfully) "No, that won't be possible." Don't say this as though you're the one making it impossible--make it clear that it's because of an external constraint. Let your boss know the limits of the constraint, so he can decide whether or not it's worth investing extra time or resources to get past it. You are not the barrier/problem here--you're willing and ready to sort out the question, given the constraints you're all dealing with.

In the situation you described:

"Can we carpool?"
"I'm afraid not; when I sent that request I hadn't made my reservations yet, but now I'm all set. Unless you can join me in my car after my flight gets in at 2 pm, we'll have to meet up at the hotel. Oh, your flight gets in at 3 and you'd like me to wait for you to be ready to leave at 4? I'd love to, but my hotel check-in is at 4, and I'd like to be sure to get there with plenty of time to spare--you never know what will come up. Oh, but you really want to ride together so we can discuss [x] project? In that case, I'm concerned I will lose my room. Let me call the hotel to see whether we can work that out so I know I'll have a place to stay."
posted by ramenopres at 9:16 PM on June 2, 2016 [2 favorites]

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