Disagreeing with the Boss

Most leaders say they don’t want “Yes-men” and “Yes-women.” But from what I can tell from senior executives’ irritation when their people give them a hard time, I’m not so sure they wouldn’t rather have the “Yes-people” variety. Consider times when someone on your team strongly opposed your point of view on a big issue - it can be quite challenging to manage this situation effectively. So, when I’m advising leaders on how to share their dissenting points of view with the Board or with the CEO, the main principle I suggest is that you can disagree without being disagreeable.

There is plenty of literature detailing why it is our natural human reaction to be nervous and avoid these hard conversations (like this article or this research), but knowing these reactions are normal probably doesn’t change the dread you may feel leading up to airing a disagreement with your supervisor. However, even though you can’t control the reactions of your manager, if you lead the conversation strategically, the business and your team will be better off.

Next time you find yourself needing to disagree with the boss or any leader who outranks you in the company hierarchy, spend a few concentrated minutes thinking about the merits of your point as well as the one with which you disagree. If you decide to pursue the discussion, consider these five principles:

1. Reassure the boss that they are the boss. I suggest saying something like “When we are done with this conversation, I’ll actively support whatever direction you choose.” This can put your boss at ease and prepare them to listen, knowing they don’t have to think about how to convince you to do what they ask. It increases your chances of being heard.
2. Establish the common ground. Whether this is calling up the team’s objective, the company’s mission, or a specific team goal, anchor the conversation in your intent to pursue the best outcomes.
3. Validate the original point you disagree with. Articulately restating their position and it’s supporting case demonstrates your understanding of their perspective. It’s powerful when someone feels you can articulate their points as well as they do. Leave out any opinions or judgments of the point – try to remain fact-based and objective.
4. Offer your perspective and rationale. Deliver it as your opinion and provide your supporting arguments (again, based in fact not subjectivity). Do it succinctly with a clear what and why.
5. Invite the conversation. Ask for your boss’s take and even critique of your suggestion. The key here is to be accepting of their feedback and ultimately, their decision whether or not to go with (or even further consider) your idea.

Once you’ve considered the perspective of your boss and done all you can to be true to your point of view, then you’ve done your part and can feel good about it. These kinds of constructive conversations are crucial if a team is going to fully utilize its talent. But they can go awry if either party is overly concerned about their ego (baked into their idea) and isn’t interested in hearing the other perspectives.

If nothing else, consider the flipside perspective of this scenario: as leaders, evaluate whether your leadership style allows for your direct reports to have these kinds of conversations with you. And when one of your team members approaches you with a differing point of view, be open and hear them out! It might have taken them a lot of courage to broach the conversation.

After all, you don’t just want “Yes-men” and “Yes-women,” do you?

Use Email for Coordination, not Conversation

I continue to be surprised about how frequently poor communication takes place over email. When I talk with executives and other consultants about this, it becomes clear to me that while email has the allure of convenience, it’s lousy for most anything complex or deep. I’ve also observed that it has become an easy way to avoid more difficult conversations.

This week I advised a client that her mantra ought to be to “use email for coordination, not conversation.” My reason was that email seemed to be her default mode of communication with people, and in most cases, it seemed to be insufficient at conveying her intentions and ideas without becoming an essay no one wants to read. I’ve also worked with leaders who spend an inordinate amount of time drafting emails, doing all they can to strike the right tone, explain each of their points sufficiently, and simultaneously be sensitive to not upsetting anyone who is reading (even when there was something to be upset about).

The pandemic pushed us more toward videoconferencing for meetings, but email traffic increased as well. The thing is, unless your message is easy to communicate, email is an astonishingly poor medium. So, use it for what it’s good for: simple topics, sharing reference material, and coordinating time for the real discussions that make your business run. 

Current Read:

I’ve been less interested lately in any partisan political views, but very interested in the way people are expressing them. What is ok to say, what isn’t, and the lack of openness to listening to arguments on either side of the Red/Blue spectrum may be a bigger concern than any policy issue that exists. Bari Weiss’s article The Great Unraveling effectively describes the challenge we all face with the current media sources. As an aside, her resignation article from The NY Times struck me as one of the best (maybe only?) pieces of real journalism of 2020.

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