How to manage a boss who always disagrees with you

We’ve all been there. I once had a boss who rarely gave me a thought-out quarterly plan or strategy, instead they left it (mostly) up to me to decide.

And then they’d nitpick all of my decisions after the quarter was over!

So why let me decide? They left it up to me because they didn’t know my job and therefore couldn’t tell me how to do it, but they still held an opinion on what I was doing.

Getting buy-in is one of the hardest things to do in normal circumstances, let alone when you’re trying to introduce an entirely new strategy or methodology across several teams.

There’s so many reasons why we can’t attain buy-in for our ideas in an organisation. It could be a lack of trust, a lack of understanding, a fear of being upstaged, a fear of being wrong, or discomfort with change.

What I’ve learned is that clear communication can solve the two pain points here: a lack of trust, a lack of understanding.

Back to my tussle with my old boss: My mistake there was not presenting them options and asking which ones they saw the most value in. Instead I was evaluating them with my experience guiding the way.

My boss didn’t have my experience, and came to different conclusions. That’s not to say one of us was right and one of us was wrong, it just meant we held different opinions but were each assuming we were on the same page.

It wasn’t until I was frustrated they kept questioning me, and they got frustrated that I was spending time on things they didn’t agree with, that we actually sat down and each gave our side. We came to understand each other’s perspectives and reached a middle ground, but that was after months, if not a year, of serious unhappiness on both sides.

Perhaps my biggest mistake was to not have this discussion sooner rather than later. I shouldn’t have avoided that friction, I needed to acknowledge it and talk it out.

Another mistake I made was to seek generic ”just let me do my job” approval. That trust needs to be built over time.

You should ask: Which area of my job is easiest to get buy-in for, that I know I’m almost guaranteed a success with? Aim for that, and formalise the buy-in with an explicit acknowledgement before moving on the next thing I want buy-in for.

Kayla Medica

Fear of being wrong and fear of being upstaged are not as easily overcome. You are not responsible for other peoples’ irrational fears and personal limitations. However, it really sucks to experience this when you work below them. To be completely honest, I haven’t personally been able to overcome this problem in a way I’d recommend.

But if a frank discussion isn’t working, I won’t leave you empty handed. Sometimes office politics are a bit dirty and it’s best to be at least aware of your options:

Find a way to change reporting lines, like asking to join a team responsible for change management or innovation (this is an option if the level above your boss has bought in to what you’re trying to do.)

Find a sponsor who is on the same level or above the person who’s blocking you, and ask them to go in to bat for you to change that person’s mind.

If getting out from under this person is truly not possible, it’s time to evaluate what you value in your role and whether staying in your job is worth the trade

If all else fails, become a secret squirrel

I have worked at a company where secret squirrels were not only encouraged, they were responsible for some of the biggest product releases and revenue. I have also worked at a company where “no secret squirrels” was an official company value (that had more secret squirrels than the company that encouraged them, ironically.)

If you’re unfamiliar with the term “secret squirrel”, it means to hide the project you’re working on, like a squirrel hides its nuts. This could mean you’re working on it over the weekend or after work hours, or you’re doing it during work hours and just not telling anyone what you’re doing. Essentially, you only reveal it when it’s finished.

Secret squirrels can work, and they can also be perceived as something that wouldn’t normally be done by a “team player”. It’s up to you if you want to run these exercises as a secret squirrel. If you have a really strong conviction that this is going to work, and have gotten an explicit “no” from leadership – this might be something you’re motivated to do in your own time and show them the results when it’s done.

The thing to watch out for here is your company culture.

Is the leader who told you “no” likely to turn around and admit they were wrong? If yes, this could be a way to get buy-in from them.

If they’re not the type to change their mind, I would advise against this. The risk is that it’ll go in the opposite direction and you’ll only find it harder to get buy-in.