BAW Ep. 16: What if your boss is wrong?

What if you're right and your boss is wrong?

And this happens quite often, more often than bosses might like to agree. Bosses are good at being bosses, and the chance of their subordinates being better than them at the actual deliverables is high. In this case, the subordinate is you, and you're telling something that you know you're right and they're wrong.

But how would you handle the situation? The conversation? The possible onslaught that might happen if you misspoke?

Things to consider

You could be wrong

First, entertain the possibility that you could be wrong. If so, how would you say this? Would you be adamant and use words that indicate absolutes? Words that leave no room for discussion? Words that might bite you back if you're wrong? Even though you know you're probably right, the probability of you being wrong is there as well. "Only a Sith deals in absolutes", as Obi-Wan puts it; and we're no Sith (I'm sorry if you don't get the reference, I'm just a sucker for it).

Choose your battle wisely

Second, consider the merit of this 'battle'. Is it worth it to be right, or it is something that does not matter that much for you to be wrong? What is the good thing that would come out of this? What is the repercussion of not speaking up when you knew better? Some wars could only be won by losing a few select battles, and some wars could be catastrophically lost because of you refusing to fight a battle.

To quote Sun Tzu,

"He will win who knows when to fight and when not to fight"

Same meaning as what I've just explained, but sounds better from a War Expert whose been dead for more than 2 centuries ago, right?

Know thy 'enemy'

Third, make sure you know your boss's style, his personality, his preferences, his way. Some people like it when you present the argument complete with the facts and figures. Some people think dislike that because it shows how wrong they were. Some like to talk it over face to face. Some would like it to be written so they can go over it in their own time at their own pace. Some cannot be approached aggressively and towardly, but some prefers no holds barred prefer if you say it like it is.

Do you know your boss's style?

Like Sun Tzu in his Art of War (again),

"If you know the enemy and know yourself, you need not fear the result of a hundred battles"

Disclaimer; your boss is not your enemy, but you get the point (hopefully).

Then what?

Then you can start to formulate your words and sentences. Say, you think your boss is wrong on a marketing strategy. You have been doing this for years and you know what works, what doesn't. And you go into a meeting to discuss the next marketing strategy. The boss is adamant on the strategy he had in mind, but you think that it was unwise because of, you know, reasons.

What do you say?

Now, remember the third point above? Before you say anything, you might want to recollect your boss's style. I will try to give you some pointers for each of the styles I know of. An early disclaimer though; nobody fits perfectly into any bucket. You'd have to estimate that yourself. You should be a better judge of your boss's character given that you've been with them a lot.

The easy-to-talk to, chatterbox boss

You start with asking questions to discover where the thinking came from and what is the objective he's trying to achieve. A lot of times, asking the right questions makes them rethink their position if they answered some things that might be counter-intuitive to what they want to achieve.

Since they like it when a conversation is going back and forth, this style fits them well. They like when their ideas are being discussed and for you to show interest by asking all these questions. What kind of questions you could ask?

• What made you arrive at this conclusion?
• What is the goal we're trying to achieve with this?
• What similar method has been done elsewhere that made you inspired to go with this?
• How much resources you think is required for this?
• What do you think of our current capability to drive this?

Make sure that your tone does not insinuate pessimism towards the idea. And I have a simple tip for that; don't be pessimistic! Remember the first point in the previous section? Consider the possibility that he's right and you're wrong. Ask questions to unearth more information about this idea.

In some (maybe most) cases, you are not openly saying you are against it, but the questions you asked begin to make their dent by making the boss rethink the merit of the idea. Even better, sometimes, they would even ask you for your input and this is where you sweep in!

This tactic is not unique to this kind of boss, but the way you ask might be. It has to be face to face, or at least verbally, and preferably when there are the whole team in the discussion. The second part is not as important as the first.

So, do not have that discussion over a text message, call him on video, and the best way is to have it face to face!

Lots of spoken words and proper body language. Draining for an introvert, I know. But it has to be done.

The meticulous and fact-driven boss

This kind of a boss might be a stickler, you think, but there are merits to it. If you were to disagree with this kind, you cannot be vague and have that mindset of, "I just know it wouldn't work because of my past experience". They welcome discussions and they welcome to a fact more right than theirs, but they do not appreciate being pointed out that they are wrong; there is a subtle difference between the two.

You can ask the questions above, but I bet they would have an answer for each of them-- but ask anyway. In the event of they do not have an answer, they wouldn't proceed with it until they have a concrete one. They might find it themselves or ask you or your team to do it. Regardless, you've successfully implanted that reasonable doubt, and this is where you slip in.

When doing so, do not include words like, "based on my experience, based on the industry's practice, in my opinion", etc. If you want to say/write those words, make sure they are backed up by actual proof. Show them tables, charts, case studies, figures, and examples. if you did it verbally in a presentation, make sure you give them a copy afterwards with carefully tailored words.

If you would like to have a discussion with them, make sure you try to do it as discreetly as possible. Again, remember, they don't like to be wrong. So, if other people are there, they might be reluctant to have that discussion.

Then, give them time for them to deliberate it and don't push it too much. If you've done your part, and they could see the angle, they would be rethinking the strategy themselves.

Arduous, yes. Part of the job.

The easy-going, non-confrontational boss

The thing about easy-going, non-confrontational bosses is that they want the team to be in a harmony. They are not necessarily hippies living in their dreams, but it would be great if everybody gets along. In that case, anything that could disturb that harmony would not be welcome. And anybody who causes that, would not be welcome as well.

It's tricky because you have to 'confront' this idea, but you don't want to be confrontational. Disagreeing without being disagreeable. Arguing without being argumentative. Debating without being adversarial.

Tricky indeed.

But there is a way.

What you want to avoid is calling out the boss's idea in front of everybody, or even in front of him directly. You would have to start slow and ease your way in. Give merits to the idea, but not necessarily for your team to adopt it, it might be good generally speaking. And that you can see why he is proposing this. It was well-intentioned. And then you say your piece and let everybody knows that you only have this discourse so that the team wouldn't come across an issue later on.

Whatever you say, frame it as if you care about the team first. And it wouldn't hurt to have that mindset once in a while. You'd like to disagree on some points not because of you think that it wouldn't work, but because if it doesn't work, it would make the team demotivated having to start all over again, and you'd rather that 'we' do things that put everybody forward.

You can still ask the same questions, but you'd have to lead with the above nuances.

You can say,

"I can see how this is a great idea, and that you think it will greatly boast our lead acquisition. It worked for company X and it would be great if it does for us. To make sure we are doing the right things and reap the benefits together, I would like to ask some questions if you don't mind."

And ask away. but if you can soften the questions without losing the point, that would be even better.

Tricky. yep, I know.

The direct and driven boss

They are imposing I kid you not. Every suggestion sounds like a direction. You might convincingly think that the idea was an order even when it is actually a mere idea projection. But that's the thing, they project. They throw it to your face, they are (seemingly) menacing. They are fast, they are result-driven, they want things to get done.

It doesn't mean that their suggestions are worthless. Is just that once they've locked in, they just want it to be done quickly. Actions taken, balls rolling, gears turning. And that is the key thing; 'locked-in'.

As shaken as you were, make sure you get your words in and plant that doubt early on. Do not let your boss lock into anything. Do not wait until later to make your case because then, he does not expect any more resistance; just compliance. At that point, as no one disagreed before, this is deemed as a consensus and the time to strategize is no longer. Now is the time for action.

So, make sure you ask those questions and slip in your own opinions in between. Take that angle that you want good results too, so that's why you ask all these questions and offer your own thoughts. This kind of bosses are task-oriented; they want to get results and they dislike bad ones more than the others. So, if you successfully tackle that angle, you might be able to change the course.

The discussion might be heated. It might be loud, not necessarily on your side. it might be argumentative. But it is necessary. Time is of essence. Every discussion will be like this. It's not particularly bad if they don't have an overarching ego to be right all the time.

Racy, yes. But you'd learn a lot.

Regardless of which style of a boss you have, remember the possibility of you being wrong as well and avoid words that leave no room for questioning. And on the flip side, there is a possibility of the boss being right. So, open up to experimentation and be on board. You'd learn either way.

Again, remember what Sun Tzu said; you have to choose your battle. Sometimes, it is not worth it to through an exhaustive discussion just to score a small point. However, if you see a merit to it, and it's kind of your job to point out as well, then you have to say something. Good bosses see your contributions AND inactions too.

What's your boss's style? What's your challenge? Let me know and we can discuss it in the comment section.

As always, good luck.